Standard Article

Hydrocyanation of Conjugated Carbonyl Compounds

  1. Wataru Nagata,
  2. Mitsuru Yoshioka*,*

Published Online: 15 JUL 2005

DOI: 10.1002/0471264180.or025.03

Organic Reactions

Organic Reactions

How to Cite

Nagata, W. and Yoshioka, M. 2005. Hydrocyanation of Conjugated Carbonyl Compounds. Organic Reactions. 25:3:255–476.

Author Information

  1. Shionogi Research Laboratory, Shionogi & Co., Ltd., Fukushima-ku, Osaka, Japan

  1. *

    We gratefully thank Mrs. Carolyn F. Sidor of E. I. du Pont de Nemours and Company for a literature search which unveiled several papers we had overlooked. We acknowledge Miss Michiko Katayama of Shionogi Research Laboratory for typing the manuscript with skill and forbearance. We would like to express our appreciation to Professor Dwight S. Fullerton, Oregon State University, who read a major part of this manuscript and made many helpful suggestions.

Publication History

  1. Published Online: 15 JUL 2005

Chemistry Terms

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Abstract

Hydrogen cyanide adds to a multiple bond in the presence of an appropriate catalyst. The process is called hydrocyanation. The addition to an α,β-unsaturated carbonyl compound gives a 1,2 adduct, α-cyanohydrin, and a 1,4 adduct, β-cyano ketone. Both 1,2 and 1,4 additions are reversible in principle, but in the presence of a base the reverse 1,2 addition is much faster than the reverse 1,4 reaction, leading to the 1,4 adduct as a major (usually sole) product.

In this sense conjugate hydrocyanation is a special case of the Michael reaction. Predominance of 1,2 or 1,4 addition depends on the substrate structure, the reagent, and the reaction conditions. In this chapter 1,2 addition is discussed only when necessary. This chapter deals chiefly with the 1,4 addition and, more generally, with conjugate addition including that on conjugated polyethylenic compounds giving 1,6 or more extended conjugated adducts. Carbonyl substrates include ketones, aldehydes, carboxylic acid derivatives, carbonitriles, and carboimines. Also included are β-functionalized carbonyl compounds, and π-allylpalladium complexes, that generate α,β-unsaturated carbonyl compounds, under hydrocyanation conditions. Although hydrogen cyanide adds to α,β-unsaturated compounds activated by other groups such as nitro and sulfone, these reactions are not considered in this chapter.

The first example of 1,4 addition of hydrogen cyanide to α,β-unsaturated carbonyl derivatives appeared more than a century ago, in 1873, when Claus prepared tricarballylic acid (1,2,3-propanetricarboxylic acid) by heating an ethanolic solution of 2,3-dichloropropene and potassium cyanide in a sealed tube.

The discovery in 1903 that the reactive species in hydrocyanation is the cyanide anion, CN, and that the rate of the reaction is proportional to the concentration of CN−8, formed the foundation for active study of hydrocyanation chemistry. A fundamental procedure for conjugate hydrocyanation was developed which used 2 molar equivalents of potassium cyanide and 1 molar equivalent of acetic acid in aqueous alcohol. The reaction mode was clarified by Ingold and Michael in the 1930s. Many chemists began extensive application of the reaction to organic syntheses, and attempts were made to explore improved procedures with higher efficiency and fewer side reactions. Detailed reviews cover developments of conjugate hydrocyanations up to the 1950s.

In recent years conjugate hydrocyanation has been used in total syntheses of complex natural products such as terpenes, steroids, and alkaloids. However, conventional procedures using hydrogen cyanide in the presence of a base or an alkali or alkaline-earth metal cyanide were not efficient. Furthermore, the efficiency could not be improved without increasing side reactions. The difficulty was overcome in 1962 when methods using organoaluminum compounds were discovered by Nagata and co-workers. They developed two new hydrocyanation methods, one involving a combination of hydrogen cyanide and an alkylaluminum and the other an alkylaluminum cyanide, both in an aprotic solvent. Applications of the new methods have led to total syntheses of complex natural products having a methyl, a functionalized methyl, or a carbon bridge at an angular position.

Keywords:

  • hydrocyanation;
  • conjugated carbonyl compounds;
  • mechanism;
  • hydrogen cyanide;
  • acetone cyanohydrin;
  • metal cyanides;
  • organoaluminum cyanides;
  • side reactions;
  • incompatible groups;
  • structure-reactivity relationships;
  • stereochemistry;
  • synthetic utility;
  • ethylenic carboxylic acid derivatives;
  • ethylenic dicarbonyl derivatives;
  • ethylenic ketones;
  • polyenic carbonyls;
  • acetylenic carbonyls;
  • scope;
  • limitations;
  • experimental procedures

Featured Compounds

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  1. 1 - 250
Compound Information
Molecular Weight:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:441.5598
Molecular Formula:C26H35NO5
InChIKey:ZQXJSAXOOHCPOJ-SUVCMDHSSA-N
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Compound Information
Molecular Weight:80.088
Molecular Formula:C4H4N2
InChIKey:IAHFWCOBPZCAEA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:HJOVHMDZYOCNQW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:87.1202
Molecular Formula:C4H12Al
InChIKey:YXFUXWCPNKUBCB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:53.491
Molecular Formula:ClH4N
InChIKey:NLXLAEXVIDQMFP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:127.1412
Molecular Formula:C6H9NO2
InChIKey:OPJCVJWGOWBMJU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.2588
Molecular Formula:C11H18O3
InChIKey:DHFJFUUWWXDDBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:255.3117
Molecular Formula:C16H17NO2
InChIKey:NLEMPVBHHZNKBB-HOCLYGCPSA-N
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Compound Information
Molecular Weight:288.3431
Molecular Formula:C19H16N2O
InChIKey:JFKRCNRGASISDY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:413.6789
Molecular Formula:C28H47NO
InChIKey:YCYIHNGNYLITHE-XYEOXEDVSA-N
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Compound Information
Molecular Weight:85.1045
Molecular Formula:C4H7NO
InChIKey:MWFMGBPGAXYFAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:270.3215
Molecular Formula:C14H22O5
InChIKey:GWJWJDLPXYCVTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:105.9884
Molecular Formula:CNa2O3
InChIKey:CDBYLPFSWZWCQE-UHFFFAOYSA-L
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Compound Information
Molecular Weight:108.0948
Molecular Formula:C6H4O2
InChIKey:AZQWKYJCGOJGHM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:203.2371
Molecular Formula:C12H13NO2
InChIKey:HJKJXWMIISKYGB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1803
Molecular Formula:C8H12O
InChIKey:FRJKTQQNQDTORT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:263.3337
Molecular Formula:C18H17NO
InChIKey:LUUXHUSXQOAOHW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.1125
Molecular Formula:C8H2N2O4
InChIKey:DWUFVOJMPJBOFS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.1525
Molecular Formula:C7H9NO
InChIKey:SMGQYTZYDJJFBP-WAYWQWQTSA-N
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Compound Information
Molecular Weight:261.3178
Molecular Formula:C18H15NO
InChIKey:WWMCIZHQDCEYDI-VAWYXSNFSA-N
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Compound Information
Molecular Weight:323.4718
Molecular Formula:C22H29NO
InChIKey:UGGITRGZAGKKAO-XUKYRZAPSA-N
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Compound Information
Molecular Weight:138.2069
Molecular Formula:C9H14O
InChIKey:VJGBUQITVKFOCM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:411.663
Molecular Formula:C28H45NO
InChIKey:FRTDELUZYNLPSK-HIDDAMQYSA-N
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Compound Information
Molecular Weight:101.19
Molecular Formula:C6H15N
InChIKey:ZMANZCXQSJIPKH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:384.6377
Molecular Formula:C27H44O
InChIKey:GPXIDAWDPZQTOS-CZRUWHASSA-N
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Compound Information
Molecular Weight:214.2152
Molecular Formula:C10H14O5
InChIKey:XHEJMECWFMVLMV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:400.6371
Molecular Formula:C27H44O2
InChIKey:YIKKMWSQVKJCOP-ABXCMAEBSA-N
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Compound Information
Molecular Weight:288.4244
Molecular Formula:C19H28O2
InChIKey:MUMGGOZAMZWBJJ-DYKIIFRCSA-N
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Compound Information
Molecular Weight:235.2805
Molecular Formula:C16H13NO
InChIKey:JRWUFQJVJGKCCT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:245.875
Molecular Formula:C6Cl4O2
InChIKey:UGNWTBMOAKPKBL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:WMOLBHJYSOSVCV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.212
Molecular Formula:C8H16O
InChIKey:RAQLTZBGPDCFJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:65.1157
Molecular Formula:CKN
InChIKey:NNFCIKHAZHQZJG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:73.0938
Molecular Formula:C3H7NO
InChIKey:ZMXDDKWLCZADIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:236.3083
Molecular Formula:C17H16O
InChIKey:DTEBZGKINVACPT-FMIVXFBMSA-N
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Compound Information
Molecular Weight:124.1609
Molecular Formula:C7H11NO
InChIKey:DTWPIGBAVKLPMD-XQRVVYSFSA-M
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Compound Information
Molecular Weight:296.4464
Molecular Formula:C21H28O
InChIKey:CPTBJMDUTZPRHG-STRKUORWSA-N
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Compound Information
Molecular Weight:454.6844
Molecular Formula:C30H46O3
InChIKey:GJEMQHMPRKOXFA-GBBOPNSLSA-N
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Compound Information
Molecular Weight:197.094
Molecular Formula:C10H5ArO2
InChIKey:JGPZFOBZPORVKL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:175.184
Molecular Formula:C10H9NO2
InChIKey:GMPNSKPTQXVWAF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:56.1056
Molecular Formula:HKO
InChIKey:KWYUFKZDYYNOTN-UHFFFAOYSA-M
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Compound Information
Molecular Weight:138.1875
Molecular Formula:C8H13NO
InChIKey:WYJGWNXECKRJRG-SREVYHEPSA-M
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Compound Information
Molecular Weight:265.305
Molecular Formula:C14H19NO4
InChIKey:NZVWRWHGAYUPQS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:87.1204
Molecular Formula:C4H9NO
InChIKey:FXHOOIRPVKKKFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:341.487
Molecular Formula:C22H31NO2
InChIKey:VQPNTLGVTIETEO-WPRIBAHSSA-N
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Compound Information
Molecular Weight:192.2112
Molecular Formula:C11H12O3
InChIKey:Not Available
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Compound Information
Molecular Weight:193.2423
Molecular Formula:C11H15NO2
InChIKey:JFXPHTQLVHEYGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:71.0779
Molecular Formula:C3H5NO
InChIKey:WOFDVDFSGLBFAC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:442.6737
Molecular Formula:C29H46O3
InChIKey:PMBSWZWCNKVWLV-OLVLZXMISA-N
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Compound Information
Molecular Weight:539.7459
Molecular Formula:C33H49NO5
InChIKey:OOHKZIRBGLVXAB-AVOCQMFOSA-N
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Compound Information
Molecular Weight:273.4131
Molecular Formula:C18H27NO
InChIKey:MBYPFETVTASJFA-HZSIZEEPSA-N
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Compound Information
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:QGEQXPHYEPMKKG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:83.068
Molecular Formula:C3H6AlN
InChIKey:XEANXLGOTCOYPM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:16.0425
Molecular Formula:CH4
InChIKey:VNWKTOKETHGBQD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:86.0892
Molecular Formula:C4H6O2
InChIKey:BAPJBEWLBFYGME-UHFFFAOYSA-N
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Compound Information
Molecular Weight:314.4617
Molecular Formula:C21H30O2
InChIKey:RJKFOVLPORLFTN-LEKSSAKUSA-N
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Compound Information
Molecular Weight:127.1412
Molecular Formula:C6H9NO2
InChIKey:IEMPSQXUZSEHEN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.3071
Molecular Formula:C17H16O3
InChIKey:HDXVSZWKIHQDES-LFYBBSHMSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:60.052
Molecular Formula:C2H4O2
InChIKey:QTBSBXVTEAMEQO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:18.0153
Molecular Formula:H2O
InChIKey:XLYOFNOQVPJJNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:44.0526
Molecular Formula:C2H4O
InChIKey:IKHGUXGNUITLKF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:26.0174
Molecular Formula:CHN
InChIKey:XFXPMWWXUTWYJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:317.4226
Molecular Formula:C19H27NO3
InChIKey:GKLTWHIQEIIKQO-TVGHHNFTSA-N
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Compound Information
Molecular Weight:411.663
Molecular Formula:C28H45NO
InChIKey:LQXDEIFCAJLJSU-JZAVPWCRSA-N
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Compound Information
Molecular Weight:112.1696
Molecular Formula:C7H12O
InChIKey:IZHBYIAZXCYIMS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:299.4504
Molecular Formula:C20H29NO
InChIKey:JRNRPSNBDLUQJX-ZVGJRIKWSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:70.0898
Molecular Formula:C4H6O
InChIKey:FUSUHKVFWTUUBE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:469.6991
Molecular Formula:C30H47NO3
InChIKey:PEZCWHAZFAQELV-OZWRSFNLSA-N
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Compound Information
Molecular Weight:481.7098
Molecular Formula:C31H47NO3
InChIKey:PNQQYPVZYFVGQB-YIGYMSAKSA-N
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Compound Information
Molecular Weight:273.2839
Molecular Formula:C15H15NO4
InChIKey:MJTZILRYFDWTMU-CMDGGOBGSA-N
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Compound Information
Molecular Weight:83.068
Molecular Formula:C3H6AlN
InChIKey:OZQKIUFSEGROHA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:319.218
Molecular Formula:I2Zn
InChIKey:UAYWVJHJZHQCIE-UHFFFAOYSA-L
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Compound Information
Molecular Weight:357.4864
Molecular Formula:C22H31NO3
InChIKey:GBYUXDSWPLTJIC-GOSCHSDWSA-N
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Compound Information
Molecular Weight:154.2063
Molecular Formula:C9H14O2
InChIKey:DKDLDGOTQWQHJP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:470.6838
Molecular Formula:C30H46O4
InChIKey:USNHWQPSGXJUQD-LZWMVOOTSA-N
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Compound Information
Molecular Weight:169.2209
Molecular Formula:C9H15NO2
InChIKey:VRHNOUQNYMQNOE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:RFGMVLSXWVHPBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.3225
Molecular Formula:C12H27AlO3
InChIKey:MDDPTCUZZASZIQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:247.3327
Molecular Formula:C15H21NO2
InChIKey:CHUIXEDKQGHIRC-YLFBSAQFSA-N
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Compound Information
Molecular Weight:295.3325
Molecular Formula:C18H17NO3
InChIKey:SOTWSEPIXMUMOY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:427.6624
Molecular Formula:C28H45NO2
InChIKey:DCIFXNAGBCWOEO-NOGRQRSOSA-N
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Compound Information
Molecular Weight:95.0993
Molecular Formula:C5H5NO
InChIKey:QUQMVLVTMRZEML-NSCUHMNNSA-N
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Compound Information
Molecular Weight:139.1519
Molecular Formula:C7H9NO2
InChIKey:VQGQPGJOHSMPQV-ONEGZZNKSA-N
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Compound Information
Molecular Weight:97.1152
Molecular Formula:C5H7NO
InChIKey:JFVBCXHSPKJLRP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.2417
Molecular Formula:C11H16O5
InChIKey:SDIINFMXNBNNFV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:275.2998
Molecular Formula:C15H17NO4
InChIKey:OCBLUPJLUUEJLO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.0851
Molecular Formula:C3H9Al
InChIKey:Not Available
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Compound Information
Molecular Weight:94.1145
Molecular Formula:C5H6N2
InChIKey:WEOKHGKSYLOTPP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:138.2055
Molecular Formula:CK2O3
InChIKey:BWHMMNNQKKPAPP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:139.1519
Molecular Formula:C7H9NO2
InChIKey:YBGPNPOLPMUQHG-HWKANZROSA-N
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Compound Information
Molecular Weight:97.1152
Molecular Formula:C5H7NO
InChIKey:LSPINEDXJRUDKO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1525
Molecular Formula:C7H10O3
InChIKey:CQWBLRNHKGEIJD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:57.05
Molecular Formula:C2H6Al
InChIKey:FZGVKIAGKYIXNA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.105
Molecular Formula:C6H11ArNO
InChIKey:FNXTZLKVBFGSMI-SNAWJCMRSA-N
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Compound Information
Molecular Weight:207.3012
Molecular Formula:C10H13NO2Si
InChIKey:KNCXOSGBFRYFAB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:62.0678
Molecular Formula:C2H6O2
InChIKey:Not Available
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Compound Information
Molecular Weight:481.7098
Molecular Formula:C31H47NO3
InChIKey:UZLZLSLFIHMSCZ-GQIIBTJASA-N
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Compound Information
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:UOLCFSMIUFFZPF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:204.2428
Molecular Formula:C9H21AlO3
InChIKey:SMZOGRDCAXLAAR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:NKEJRIVBBYFOPK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:497.7092
Molecular Formula:C31H47NO4
InChIKey:NAUPTNIQHYKIRB-RCCZQDMQSA-N
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Compound Information
Molecular Weight:294.3908
Molecular Formula:C19H22N2O
InChIKey:YFMNMPLJIWVXER-VGOFMYFVSA-N
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Compound Information
Molecular Weight:60.1182
Molecular Formula:C3H9N
InChIKey:GETQZCLCWQTVFV-UHFFFAOYSA-O
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Compound Information
Molecular Weight:315.4498
Molecular Formula:C20H29NO2
InChIKey:FYXFHBLBSLNOGN-KKCKYBGUSA-N
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Compound Information
Molecular Weight:114.1648
Molecular Formula:C6H15Al
InChIKey:VOITXYVAKOUIBA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:228.2863
Molecular Formula:C15H16O2
InChIKey:FQSUSXXSHPWBMR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:246.3877
Molecular Formula:C17H26O
InChIKey:ZQKGWPOFOVJYTD-YQQAZPJKSA-N
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Compound Information
Molecular Weight:411.663
Molecular Formula:C28H45NO
InChIKey:ZUYALGIWBYZIFI-YUMNVOTQSA-N
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Compound Information
Molecular Weight:92.113
Molecular Formula:C2CaN2
InChIKey:OEYMAKISKGNYAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:OHERZLWVBJCXOF-NSHDSACASA-N
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Compound Information
Molecular Weight:149.1897
Molecular Formula:C9H11NO
InChIKey:OMMMPVYVGOFREA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:321.4161
Molecular Formula:C20H23N3O
InChIKey:SEAPUCZREPKOFF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:124.1609
Molecular Formula:C7H11NO
InChIKey:DTWPIGBAVKLPMD-XQRVVYSFSA-M
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Compound Information
Molecular Weight:137.136
Molecular Formula:C7H7NO2
InChIKey:PEPYGRMHYSHYSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:225.082
Molecular Formula:C10H9BrO
InChIKey:JBABXKFMMMDQNC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:72.1057
Molecular Formula:C4H8O
InChIKey:WYURNTSHIVDZCO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:290.3972
Molecular Formula:C18H26O3
InChIKey:WZGGFEZQPHBWAI-JSGCGXOISA-N
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Compound Information
Molecular Weight:111.1211
Molecular Formula:C5H10AlN
InChIKey:KWMUAEYVIFJZEB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:182.2164
Molecular Formula:C10H14O3
InChIKey:PNVAFVJGHQDUPA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0419
Molecular Formula:CH4O
InChIKey:OKKJLVBELUTLKV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:414.5345
Molecular Formula:C25H34O5
InChIKey:UGTGGLOTLSAFLH-FYVXYBBASA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:138.1875
Molecular Formula:C8H13NO
InChIKey:WYJGWNXECKRJRG-SREVYHEPSA-M
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:VDTIJFRUZIAMNB-RYUDHWBXSA-N
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Compound Information
Molecular Weight:166.1772
Molecular Formula:C8H10N2O2
InChIKey:IXBFNZIDOVAPNV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:88.1051
Molecular Formula:C4H8O2
InChIKey:RYHBNJHYFVUHQT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:110.1537
Molecular Formula:C7H10O
InChIKey:LKTNAAYQZJAXCJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:101.1232
Molecular Formula:C5H8O2
InChIKey:MCVVUJPXSBQTRZ-UHFFFAOYSA-O
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:165.2322
Molecular Formula:C10H15NO
InChIKey:JJDFVIDVSCYKDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.0987
Molecular Formula:C5H8O4
InChIKey:WXUAQHNMJWJLTG-UHFFFAOYSA-L
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Compound Information
Molecular Weight:224.119
Molecular Formula:C11H6ArNO2
InChIKey:NRFCQUUOSGEGSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.1891
Molecular Formula:C9H11NO2
InChIKey:VPBYQYFCHCJWHB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:274.3581
Molecular Formula:C16H22N2O2
InChIKey:ZBIHVUCPAGDNMR-JPHNVSBRSA-N
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Compound Information
Molecular Weight:129.448
Molecular Formula:C3H2ArClO
InChIKey:SMTHJKCHHKYZKY-OWOJBTEDSA-N
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Compound Information
Molecular Weight:53.0626
Molecular Formula:C3H3N
InChIKey:NLHHRLWOUZZQLW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:46.0684
Molecular Formula:C2H6O
InChIKey:LFQSCWFLJHTTHZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:78.1118
Molecular Formula:C6H6
InChIKey:UHOVQNZJYSORNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:454.6844
Molecular Formula:C30H46O3
InChIKey:CZMSMYXJNVSLRU-AQBQUVEZSA-N
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Compound Information
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:GYCMBHHDWRMZGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:272.425
Molecular Formula:C19H28O
InChIKey:MSEZLHAVPJYYIQ-VMXHOPILSA-N
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Compound Information
Molecular Weight:113.1146
Molecular Formula:C5H7NO2
InChIKey:BPSKURPOKFSLHJ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:99.1311
Molecular Formula:C5H9NO
InChIKey:SECXISVLQFMRJM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:252.107
Molecular Formula:C11H10BrNO
InChIKey:CZFMVNRMLPEAHV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:218.2485
Molecular Formula:C13H14O3
InChIKey:AYZGINZXVVKWKV-XFXZXTDPSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:VVQNEPGJFQJSBK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:384.6377
Molecular Formula:C27H44O
InChIKey:NYOXRYYXRWJDKP-GYKMGIIDSA-N
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Compound Information
Molecular Weight:122.1246
Molecular Formula:C6H6N2O
InChIKey:UISCCMNMQMKTAQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:36.461
Molecular Formula:ClH
InChIKey:VEXZGXHMUGYJMC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:98.143
Molecular Formula:C6H10O
InChIKey:SHOJXDKTYKFBRD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:120.013
Molecular Formula:C4H2ArNO
InChIKey:IECLERKVAPBHME-OWOJBTEDSA-N
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Compound Information
Molecular Weight:234.2925
Molecular Formula:C17H14O
InChIKey:WMKGGPCROCCUDY-HEEUSZRZSA-N
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Compound Information
Molecular Weight:512.7205
Molecular Formula:C32H48O5
InChIKey:KGIAYGKZKWKTGY-ROIDOBTBSA-N
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Compound Information
Molecular Weight:248.2744
Molecular Formula:C14H16O4
InChIKey:VUWPIBNKJSEYIN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.1898
Molecular Formula:C9H12O3
InChIKey:DEQTYMUZSHEIHH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:99.2065
Molecular Formula:C4H9NSi
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:171.342
Molecular Formula:BaH2O2
InChIKey:RQPZNWPYLFFXCP-UHFFFAOYSA-L
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Compound Information
Molecular Weight:98.103
Molecular Formula:C4H9AlN
InChIKey:PQMXDWQKTXESAY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:26.0174
Molecular Formula:CHN
InChIKey:XFXPMWWXUTWYJX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:112.1265
Molecular Formula:C6H8O2
InChIKey:IYNRVIKPUTZSOR-HWKANZROSA-N
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Compound Information
Molecular Weight:246.2586
Molecular Formula:C14H14O4
InChIKey:QKATZXQTAXGSBB-RMKNXTFCSA-N
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Compound Information
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:SJNALLRHIVGIBI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:208.2552
Molecular Formula:C15H12O
InChIKey:DQFBYFPFKXHELB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:114.1424
Molecular Formula:C6H10O2
InChIKey:ZFDIRQKJPRINOQ-HWKANZROSA-N
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Compound Information
Molecular Weight:138.1875
Molecular Formula:C8H13NO
InChIKey:WYJGWNXECKRJRG-SREVYHEPSA-M
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:VDTIJFRUZIAMNB-NWDGAFQWSA-N
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Compound Information
Molecular Weight:124.1609
Molecular Formula:C7H11NO
InChIKey:DTWPIGBAVKLPMD-XQRVVYSFSA-M
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Compound Information
Molecular Weight:255.3117
Molecular Formula:C16H17NO2
InChIKey:NLEMPVBHHZNKBB-ZBFHGGJFSA-N
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Compound Information
Molecular Weight:514.7412
Molecular Formula:C34H46N2O2
InChIKey:FEKYPGBXHXDAFK-PPNRDHFASA-N
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Compound Information
Molecular Weight:98.1861
Molecular Formula:C7H14
InChIKey:UAEPNZWRGJTJPN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:128.169
Molecular Formula:C7H12O2
InChIKey:CQEYYJKEWSMYFG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:183.2044
Molecular Formula:C9H13NO3
InChIKey:NWEUVBNCYAHVNV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:170.2057
Molecular Formula:C9H14O3
InChIKey:CLQJWPPYTJZVNK-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:96.1271
Molecular Formula:C6H8O
InChIKey:FWFSEYBSWVRWGL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.055
Molecular Formula:C5H6ArNO2
InChIKey:MFQJROBQRXKEOV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:160.1247
Molecular Formula:C6H8O5
InChIKey:YIXSKDRXJTZCHT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:319.1562
Molecular Formula:C4K4N4Ni
InChIKey:DLTYVLCKTDLXPT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:118.088
Molecular Formula:C4H6O4
InChIKey:KDYFGRWQOYBRFD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:130.943
Molecular Formula:C3HAr2N
InChIKey:KJUHVRYYPQOJRE-IWQZZHSRSA-N
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Compound Information
Molecular Weight:97.1152
Molecular Formula:C5H7NO
InChIKey:YGBHRJCYEZIPDN-GORDUTHDSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:BEEXXCVMIQVOBZ-IJLUTSLNSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:SKCQLERPBSCSMA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:165.2322
Molecular Formula:C10H15NO
InChIKey:URWILODWYJZMCC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:233.031
Molecular Formula:C7H7Ar2NO3
InChIKey:KGIINHOOHKGWPW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:169.148
Molecular Formula:C7H15ArNO
InChIKey:HFXFTUAIYFDCNE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:140.1797
Molecular Formula:C8H12O2
InChIKey:DZDLRYVBEAOWDV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.2038
Molecular Formula:C9H13NO4
InChIKey:YYSVDCIWMHWVRN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:137.179
Molecular Formula:C8H11NO
InChIKey:YSPFDNJAOZYKLD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:327.4605
Molecular Formula:C21H29NO2
InChIKey:URLUEOQNSPQNBR-JMBFZUFFSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:KMEDIOVHRDQREA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:487.7159
Molecular Formula:C33H45NO2
InChIKey:AOVUHFFTWGDLMR-CHXOVHLMSA-N
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Compound Information
Molecular Weight:111.0987
Molecular Formula:C5H5NO2
InChIKey:MWCLLHOVUTZFKS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:152.055
Molecular Formula:C5H6ArNO2
InChIKey:CFJLFIHPYKWTAV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:151.2056
Molecular Formula:C9H13NO
InChIKey:GAALUGSXOYIKSP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:367.4813
Molecular Formula:C23H29NO3
InChIKey:MYDYMFGBXMAPLX-VYAQIDIUSA-N
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Compound Information
Molecular Weight:131.216
Molecular Formula:C7H17NO
InChIKey:HURLLCJYGATXPR-UHFFFAOYSA-N
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Compound Information
Molecular Weight:152.1937
Molecular Formula:C8H12N2O
InChIKey:AQYVRESAOPMHJQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2441
Molecular Formula:C11H16O
InChIKey:SHJURGBKFRIEAS-SECBINFHSA-N
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Compound Information
Molecular Weight:160.077
Molecular Formula:C7H6ArNO
InChIKey:RTQOHLZLAWVPTK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:17.0305
Molecular Formula:H3N
InChIKey:QGZKDVFQNNGYKY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:316.4345
Molecular Formula:C20H28O3
InChIKey:TTWYUPSVWLOIRF-GUZBNGIKSA-N
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Compound Information
Molecular Weight:180.2866
Molecular Formula:C12H20O
InChIKey:CUUZZZQYSLHVPL-NWDGAFQWSA-N
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Compound Information
Molecular Weight:342.4751
Molecular Formula:C21H30N2O2
InChIKey:OHLPDSIEKROYBZ-DKNDPHALSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:NZGWDASTMWDZIW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.055
Molecular Formula:C5H6ArNO
InChIKey:QKPRYIRFBZEWGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:PPBNRZWRDONNJO-ONGXEEELSA-N
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Compound Information
Molecular Weight:95.0993
Molecular Formula:C5H5NO
InChIKey:KRTNCALJETZRGN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:157.968
Molecular Formula:C4H2Ar2N2
InChIKey:AMDIIJDTLRDSPB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:378.933
Molecular Formula:C22H31ClO3
InChIKey:BSMPVUNPKIEXPX-LCDGHNAASA-N
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Compound Information
Molecular Weight:114.1855
Molecular Formula:C7H14O
InChIKey:AZASWMGVGQEVCS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:47.0134
Molecular Formula:HNO2
InChIKey:IOVCWXUNBOPUCH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:143.1836
Molecular Formula:C7H13NO2
InChIKey:UINUXFJCLDZRHO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:123.1525
Molecular Formula:C7H9NO
InChIKey:LKDIPHAFHPYCOL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:125.1253
Molecular Formula:C6H7NO2
InChIKey:MKCRHZAATLTPAO-HWKANZROSA-N
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Compound Information
Molecular Weight:138.124
Molecular Formula:C6H6N2O2
InChIKey:UIRLWVNHZJRFMW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:97.1582
Molecular Formula:C6H11N
InChIKey:DFOQDORWNLHNCK-FNORWQNLSA-N
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Compound Information
Molecular Weight:106.029
Molecular Formula:C4H4ArN
InChIKey:NMOKSNWVBAJZDX-RQOWECAXSA-N
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Compound Information
Molecular Weight:217.3068
Molecular Formula:C14H19NO
InChIKey:DTNLGTPXOSXKOK-UONOGXRCSA-N
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Compound Information
Molecular Weight:37.833
Molecular Formula:BH4Na
InChIKey:YOQDYZUWIQVZSF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:371.5991
Molecular Formula:C25H41NO
InChIKey:MZMQYTHUMFGYQI-AKDPOQJMSA-N
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Compound Information
Molecular Weight:256.2949
Molecular Formula:C13H20O5
InChIKey:UZFCLGIGDOLULP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:254.7221
Molecular Formula:C4N4Na4Ni
InChIKey:SUDBLDWOGKAOMQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:136.191
Molecular Formula:C9H12O
InChIKey:VJESNDWIKWQBSV-QMMMGPOBSA-N
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Compound Information
Molecular Weight:286.4085
Molecular Formula:C19H26O2
InChIKey:GYXFOOCGIVDNFH-UODWBKHISA-N
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Compound Information
Molecular Weight:385.4965
Molecular Formula:C23H31NO4
InChIKey:CYLMIXJBCBHFPE-GESJEARISA-N
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Compound Information
Molecular Weight:121.1366
Molecular Formula:C7H7NO
InChIKey:COTIABIUMVVFRH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:107.11
Molecular Formula:C6H5NO
InChIKey:FPQQNWAYKBBBLC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:95.003
Molecular Formula:C3H3ArO
InChIKey:YXOBSQWXDYEDRT-UHFFFAOYSA-N
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Compound Information
Molecular Weight:150.2176
Molecular Formula:C10H14O
InChIKey:HJDKCIOQDUHLEF-JTQLQIEISA-N
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Compound Information
Molecular Weight:157.028
Molecular Formula:C4H5ArO4
InChIKey:FBNJDCJVKDWGMZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.006
Molecular Formula:C6H6Ar2O3
InChIKey:FFJHENXHSYRISU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:153.1784
Molecular Formula:C8H11NO2
InChIKey:IIWRFGNQSYWUFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:111.1418
Molecular Formula:C6H9NO
InChIKey:KTCGZVXFIGQRNB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:32.0452
Molecular Formula:H4N2
InChIKey:OAKJQQAXSVQMHS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:85.1238
Molecular Formula:C5H8O
InChIKey:LABTWGUMFABVFG-UHFFFAOYSA-O
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Compound Information
Molecular Weight:188.1779
Molecular Formula:C8H12O5
InChIKey:UYKGGYVGYSHLDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:199.649
Molecular Formula:C4H8CuO5
InChIKey:NWFNSTOSIVLCJA-UHFFFAOYSA-L
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