Standard Article

Glycosylation with Sulfoxides and Sulfinates as Donors or Promoters

  1. David Crich1,
  2. Linda B. L. Lim2

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or064.02

Organic Reactions

Organic Reactions

How to Cite

Crich, D. and Lim, L. B. L. 2004. Glycosylation with Sulfoxides and Sulfinates as Donors or Promoters. Organic Reactions. 64:2:115–251.

Author Information

  1. 1

    University of Illinois at Chicago, Department of Chemistry, Chicago, Illinois, USA

  2. 2

    University of Brunei Darussalam, Department of Chemistry, Negara Brunei Darussalam

Publication History

  1. Published Online: 15 OCT 2004

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Abstract

The efficient, stereocontrolled formation of glycosidic bonds is arguably the most fundamental reaction in glycoscience. This chapter surveys four recent distinct glycosylation methods united by the common theme of employing sulfoxides, or closely related sulfinates, either in the glycosyl donor itself or as an integral part of the promoter. In the first method (the sulfoxide method), a glycosyl sulfoxide, the donor, is coupled to an acceptor alcohol by means of an activating agent to give the glycosidic bond. The activating agent is typically triflic anhydride, but other compounds have been used.

In the second method (the thiogylcoside method) the donor is thioglycoside. It is activated by means of a promoter derived from the reaction of trifluoromethanesulfonic anhydride and thiosulfinate, a sulfinaminde, or diphenylsulfoxide before coupling to an acceptor alcohol. The third method is dehydrative coupling. This chapter is concerned only with the recent variations in which dehydration is achieved by means of a combination of diaryl sulfoxides and trifluoromethanesulfonic acid. The last method (the oxidative method), involves the direct oxidative glycosylation of glycals. This method differs significantly from the other methods since it does not employ a traditional anomeric derivative as glycosly donor, but derives one from the formal oxidation of glycal.

At some time in the activation process, all four methods typically involve the reaction of a sulfoxide, or sulfinate with trifluoromethanesulfonic anhydride. All four methods possess the distinct advantage of using readily prepared, stable gylcosyl donors. Three of them are metal-free and two of them are capable of coupling to enable the most hindered unreactive alcohols in a matter of minutes at low temperature. These methods are some of the most powerful available for the formation of glycosidic linkages.

Keywords:

  • glycoslyation;
  • mechanisms;
  • oxidative method;
  • sulfoxide method;
  • dehydrative method;
  • thioglycoside/sulfinate method;
  • scope;
  • limitations;
  • donors;
  • acceptors;
  • N-Glycosides;
  • nucleosides;
  • C-Glycosides;
  • sulfoxides;
  • promoters;
  • bond formation;
  • synthesis applications;
  • method comparisons;
  • solvents;
  • functional group compatibility;
  • pyranoside;
  • furnanosides;
  • experimental procedures

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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:119.378
Molecular Formula:CHCl3
InChIKey:HEDRZPFGACZZDS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:394.14
Molecular Formula:C15H33NO3Sn
InChIKey:JDSJUGNNRWABFW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:362.3292
Molecular Formula:C15H22O10
InChIKey:AUVGRVGPAIFPSA-KYFQHEKYSA-N
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Compound Information
Molecular Weight:829.9326
Molecular Formula:C48H51N3O10
InChIKey:PGAGLSIXAWCMBA-SEMVFMAASA-N
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Compound Information
Molecular Weight:282.139
Molecular Formula:C2F6O5S2
InChIKey:WJKHJLXJJJATHN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:440.5287
Molecular Formula:C26H32O6
InChIKey:KJPPJTYINPOAOQ-XCEYXQIPSA-N
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Compound Information
Molecular Weight:1412.6569
Molecular Formula:C82H97N3O18
InChIKey:CXJACXVGCXYIDH-ORANWDJRSA-N
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Compound Information
Molecular Weight:524.667
Molecular Formula:C27H40O8S
InChIKey:CBMBSEMEBALHLX-ADAARDCZSA-N
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Compound Information
Molecular Weight:330.441
Molecular Formula:C19H22O3S
InChIKey:SWGPMCWYRWNFLL-XVVUIKCHSA-N
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Compound Information
Molecular Weight:650.8397
Molecular Formula:C36H58O10
InChIKey:IETBHZFRRKZXKG-WGMWNUKXSA-N
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Compound Information
Molecular Weight:456.5281
Molecular Formula:C26H32O7
InChIKey:PCJQRJVMTCZFBW-JOUFPCHASA-N
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Compound Information
Molecular Weight:456.464
Molecular Formula:C20H24O10S
InChIKey:ASSTVYHCAZVPCR-HIESPICJSA-N
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Molecular Weight:548.56
Molecular Formula:C29H24O9S
InChIKey:IGFFVHREDNZTOZ-AYPTXYQFSA-N
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Compound Information
Molecular Weight:209.308
Molecular Formula:C11H15NOS
InChIKey:LBRJCAJLGAXDKP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1163.2
Molecular Formula:C67H54O17S
InChIKey:RLRQYCJHVNSYQM-IJUUQZCJSA-N
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Compound Information
Molecular Weight:664.651
Molecular Formula:C32H40O15
InChIKey:YAQJHNFAJUTKRJ-IQLKFJAHSA-N
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Compound Information
Molecular Weight:570.609
Molecular Formula:C32H26O8S
InChIKey:OOTMZMSQXWPUTM-OJWAFDQYSA-N
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Compound Information
Molecular Weight:884.043
Molecular Formula:C45H61N3O13S
InChIKey:HGDCLFUSVCJXGW-GMWZZYCESA-N
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Compound Information
Molecular Weight:505.585
Molecular Formula:C27H27N3O5S
InChIKey:IUWCOBQCJOHGSQ-BLQNYSDHSA-N
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Compound Information
Molecular Weight:113.545
Molecular Formula:C5H4ClN
InChIKey:OKDGRDCXVWSXDC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:358.408
Molecular Formula:C19H18O5S
InChIKey:FCMWOBURMWZPOC-QEGXYTCLSA-N
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Compound Information
Molecular Weight:448.7845
Molecular Formula:C22H48O5Si2
InChIKey:WRBHJEVUZODUSX-XNTOXWQXSA-N
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Compound Information
Molecular Weight:1505.2951
Molecular Formula:C82H125NO15Si5
InChIKey:JRLYKUBYTNKZKG-NXPCLYBWSA-N
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Compound Information
Molecular Weight:848.8328
Molecular Formula:C40H53IO10Si
InChIKey:GNPQTUWGIPRZPK-LWOISQMQSA-N
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Compound Information
Molecular Weight:949.1282
Molecular Formula:C50H76O17
InChIKey:YWBRIERTEFOOEW-HVTWTHCGSA-N
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Compound Information
Molecular Weight:594.629
Molecular Formula:C31H30O10S
InChIKey:PHYKLHMGXNOOKS-MVRPCCFLSA-N
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Compound Information
Molecular Weight:759.387
Molecular Formula:C37H74O6SSi4
InChIKey:LJIRPUUHZGWCLF-OCRVYOHJSA-N
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Compound Information
Molecular Weight:386.3
Molecular Formula:C15H21N3O4Se
InChIKey:RSBCEYAMJGTQII-XLWJZTARSA-N
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Compound Information
Molecular Weight:440.464
Molecular Formula:C20H24O9S
InChIKey:JCKOUAWEMPKIAT-OBKDMQGPSA-N
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Compound Information
Molecular Weight:449.0646
Molecular Formula:C8F17NO
InChIKey:RDGJBZXVLOXHPC-DGXCBMPPSA-N
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Compound Information
Molecular Weight:410.643
Molecular Formula:C21H34O4SSi
InChIKey:LWTTUTFPDXRLAA-NLNMYJFZSA-N
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Compound Information
Molecular Weight:1086.163
Molecular Formula:C55H63N3O18S
InChIKey:QYZSHGLNSNXNNA-QVAWCUOESA-N
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Compound Information
Molecular Weight:844.9837
Molecular Formula:C51H56O11
InChIKey:LALBPFXBCGSZGY-KRCRLAFXSA-N
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Compound Information
Molecular Weight:429.357
Molecular Formula:C20H22Cl2O4S
InChIKey:YFWAACBYOXDIAK-OZOSWLFCSA-N
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Compound Information
Molecular Weight:443.21
Molecular Formula:C20H36O3Sn
InChIKey:ORLKDSRVPJZUMY-UHFFFAOYSA-M
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Compound Information
Molecular Weight:358.3453
Molecular Formula:C18H18N2O6
InChIKey:NFLAFZYYOJVGGS-PMUMKWKESA-N
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Compound Information
Molecular Weight:600.721
Molecular Formula:C35H36O7S
InChIKey:SQNSRVBYMCPUAM-KYDRTLKZSA-N
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Compound Information
Molecular Weight:129.061
Molecular Formula:C2H6Cl2Si
InChIKey:Not Available
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Compound Information
Molecular Weight:218.2469
Molecular Formula:C10H18O5
InChIKey:TVKKWQAJQZHTDN-OFPUPOEVSA-N
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Compound Information
Molecular Weight:554.6296
Molecular Formula:C34H34O7
InChIKey:FRHKLSCGNMWMMT-HPQQSSMTSA-N
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Compound Information
Molecular Weight:1158.6255
Molecular Formula:C72H95N3O8Si
InChIKey:CRJDPNIHHZODOD-MMBUFVNYSA-N
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Compound Information
Molecular Weight:845.9718
Molecular Formula:C50H55NO11
InChIKey:ZECVCQLXTMKRKT-CDQDAYCYSA-N
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Compound Information
Molecular Weight:1000.201
Molecular Formula:C51H73N3O15S
InChIKey:PJIDBLASQOGIHA-NZQYOXTJSA-N
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Compound Information
Molecular Weight:492.626
Molecular Formula:C29H32O5S
InChIKey:JDBLGLZAAWCNMD-ULFZGVROSA-N
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Compound Information
Molecular Weight:484.612
Molecular Formula:C23H36O9Si
InChIKey:INDWGBBQIQSBTJ-JXDTVZCFSA-N
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Compound Information
Molecular Weight:459.512
Molecular Formula:C23H25NO7S
InChIKey:ZXWMLGNJXPXHTR-XFWGSAIBSA-N
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Compound Information
Molecular Weight:851.56
Molecular Formula:C38H57IO4SiSn
InChIKey:NHYYSUNXAATWSK-UHFFFAOYSA-M
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Compound Information
Molecular Weight:218.338
Molecular Formula:C12H10S2
InChIKey:Not Available
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Compound Information
Molecular Weight:1033.422
Molecular Formula:C58H72O11SSi2
InChIKey:NLTKWTPKKAQNCP-GZUGMAMWSA-N
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Compound Information
Molecular Weight:515.46
Molecular Formula:C21H20F3N3O7S
InChIKey:DUYDPQCDHQOERF-DNDRQTMDSA-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:1272.2672
Molecular Formula:C57H77N9O24
InChIKey:HINYHIWWZNSZNE-RQNHHPERSA-N
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Compound Information
Molecular Weight:432.5082
Molecular Formula:C27H28O5
InChIKey:ZRLDYWSQTIAJDQ-IURCNINISA-N
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Compound Information
Molecular Weight:529.5788
Molecular Formula:C28H35NO9
InChIKey:ARSJJCNIBCQDJG-YGRHAXQVSA-N
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Compound Information
Molecular Weight:60.0843
Molecular Formula:O2Si
InChIKey:VYPSYNLAJGMNEJ-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:1041.096
Molecular Formula:C56H64O19
InChIKey:KYAGFLQULZNREM-RCOCXLFXSA-N
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Compound Information
Molecular Weight:1043.1149
Molecular Formula:C62H58O15
InChIKey:KGGQKUPKURALRO-STQDLUFUSA-N
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Compound Information
Molecular Weight:416.5088
Molecular Formula:C27H28O4
InChIKey:MXYLLYBWXIUMIT-PFBJBMPXSA-N
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Compound Information
Molecular Weight:1557.982
Molecular Formula:C100H116O15
InChIKey:NXGPFILEKWQBDP-KYTVTRQDSA-N
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Compound Information
Molecular Weight:593.806
Molecular Formula:C32H39NO6SSi
InChIKey:ZXNUMMWQFITBPV-FQYQUSJJSA-N
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Compound Information
Molecular Weight:766.85
Molecular Formula:C40H46O13S
InChIKey:ABYQTVXOAJUGIR-GCVMFESXSA-N
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Compound Information
Molecular Weight:1209.1599
Molecular Formula:C61H64N2O24
InChIKey:ZZCGBRKSELIEPP-RBGSNVJHSA-N
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Compound Information
Molecular Weight:564.689
Molecular Formula:C32H36O7S
InChIKey:NMUCADLAAMNGAW-YUCFEETJSA-N
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Compound Information
Molecular Weight:318.4058
Molecular Formula:C16H30O6
InChIKey:KBMAHMXTIVYWOQ-IBEHDNSVSA-N
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Compound Information
Molecular Weight:711.734
Molecular Formula:C31H41N3O14S
InChIKey:MLUPJQKINJTKKO-DYXQMVLRSA-N
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Compound Information
Molecular Weight:551.7168
Molecular Formula:C32H45N3O5
InChIKey:PEBTWCRTAOQAAA-JBOQNHBVSA-N
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Compound Information
Molecular Weight:223.58
Molecular Formula:HgNa
InChIKey:ZFTWYSPLZZVANZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:692.8333
Molecular Formula:C37H56O12
InChIKey:VHQVPEPCPPVYRC-LJNCTHMASA-N
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Compound Information
Molecular Weight:344.423
Molecular Formula:C16H24O6S
InChIKey:CUXONSWRUQIMMI-LYYZXLFJSA-N
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Compound Information
Molecular Weight:149.2328
Molecular Formula:C10H15N
InChIKey:GGSUCNLOZRCGPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:462.4481
Molecular Formula:C26H22O8
InChIKey:OLJXZMADUXHNCS-CHJIAWOGSA-N
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Compound Information
Molecular Weight:818.9434
Molecular Formula:C43H62O15
InChIKey:QRENTWOSGMPAHU-SQNMUPFJSA-N
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Compound Information
Molecular Weight:136.315
Molecular Formula:Cl2Zn
InChIKey:Not Available
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Compound Information
Molecular Weight:2880.05
Molecular Formula:H3O40PW12
InChIKey:IYDGMDWEHDFVQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:448.648
Molecular Formula:C23H32O5SSi
InChIKey:RXKLNCZOGQURNJ-FWTDUKKUSA-N
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Compound Information
Molecular Weight:503.4985
Molecular Formula:C25H29NO10
InChIKey:ZAPHKLVGFBSDHU-NSEXGNSCSA-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:222.258
Molecular Formula:C4H9F3O3SSi
InChIKey:FTVLMFQEYACZNP-UHFFFAOYSA-N
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Compound Information
Molecular Weight:39.9971
Molecular Formula:HNaO
InChIKey:HEMHJVSKTPXQMS-UHFFFAOYSA-M
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Compound Information
Molecular Weight:34.0147
Molecular Formula:H2O2
InChIKey:MHAJPDPJQMAIIY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:456.464
Molecular Formula:C20H24O10S
InChIKey:BHFXDDNMCLGAAN-QXRUFTLNSA-N
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Compound Information
Molecular Weight:897.0583
Molecular Formula:C55H60O11
InChIKey:CNWCJQVLRGGEFN-GDPVUEBWSA-N
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Compound Information
Molecular Weight:1627.7689
Molecular Formula:C94H98O25
InChIKey:QHEHPNIXFCYOHT-PMEVTEAKSA-N
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Compound Information
Molecular Weight:132.1577
Molecular Formula:C6H12O3
InChIKey:RNVYQYLELCKWAN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:320.2925
Molecular Formula:C13H20O9
InChIKey:OBVFJYUDIWPVKD-LBELIVKGSA-N
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Compound Information
Molecular Weight:494.599
Molecular Formula:C28H30O6S
InChIKey:LIJAZAVJRADHBV-YTZCDUBRSA-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:386.418
Molecular Formula:C20H18O6S
InChIKey:SEVDUIWHFBFJIY-RCFCFVIZSA-N
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Compound Information
Molecular Weight:622.887
Molecular Formula:C35H46O6SSi
InChIKey:MAGHITKDBJSSAE-GZLVETBOSA-N
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Compound Information
Molecular Weight:85.1475
Molecular Formula:C5H11N
InChIKey:Not Available
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Compound Information
Molecular Weight:105.0926
Molecular Formula:C3H7NO3
InChIKey:VGEWEGHHYWGXGG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:977.2675
Molecular Formula:C54H88O15
InChIKey:ZWLANZFHMYGJLK-BNDQAWDMSA-N
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Compound Information
Molecular Weight:292.316
Molecular Formula:C10H10Cl2Zr
InChIKey:QGNRHWVXMACQOC-UHFFFAOYSA-L
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Compound Information
Molecular Weight:108.1378
Molecular Formula:C7H8O
InChIKey:WVDDGKGOMKODPV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:670.811
Molecular Formula:C39H42O8S
InChIKey:XGQOFROEKWMRED-RIQASFFASA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:RTZKZFJDLAIYFH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:369.3682
Molecular Formula:C16H36IN
InChIKey:DPKBAXPHAYBPRL-UHFFFAOYSA-M
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Compound Information
Molecular Weight:568.662
Molecular Formula:C32H30N3O5S
InChIKey:DZDGACYCKZWLME-YJROXGMRSA-N
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Compound Information
Molecular Weight:401.436
Molecular Formula:C19H19N3O5S
InChIKey:FDDYPUNCOQAKCC-WGNPIITISA-N
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Compound Information
Molecular Weight:494.6606
Molecular Formula:C28H46O7
InChIKey:KIRFLCKWEBLZMD-XIXNWCAMSA-N
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Compound Information
Molecular Weight:764.7253
Molecular Formula:C39H40O16
InChIKey:GEFNUOJZXRDFIG-UQWKJJIUSA-N
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Compound Information
Molecular Weight:492.6032
Molecular Formula:C30H36O6
InChIKey:CTEMNFRCFHGESM-CMPUJJQDSA-N
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Compound Information
Molecular Weight:1079.373
Molecular Formula:C63H70O12SSi
InChIKey:ZUWYBSNJSCGABV-DGGHZZJYSA-N
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Compound Information
Molecular Weight:336.358
Molecular Formula:C13H20O8S
InChIKey:NUHNOSTYGCZQAG-KVSVUVNWSA-N
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Compound Information
Molecular Weight:534.662
Molecular Formula:C28H38O8S
InChIKey:SZPRXQBZOWLFQT-ZUEGJGKGSA-N
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Compound Information
Molecular Weight:554.61
Molecular Formula:C32H26O7S
InChIKey:HJSVHTQFGAHJNM-IDSQFFPFSA-N
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Compound Information
Molecular Weight:501.595
Molecular Formula:C25H31N3O6S
InChIKey:BDIXRXRLONOXGD-GNJRFXKQSA-N
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Compound Information
Molecular Weight:475.5363
Molecular Formula:C27H29N3O5
InChIKey:QDBCDZSWKHVHAB-SEFGFODJSA-N
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Compound Information
Molecular Weight:1495.785
Molecular Formula:C95H98O16
InChIKey:BMXZFCUKWNMDEC-JQUSBBTASA-N
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Compound Information
Molecular Weight:610.833
Molecular Formula:C33H42O7SSi
InChIKey:KAVQNOYDJIHZSW-HCQIWOKWSA-N
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Compound Information
Molecular Weight:813.955
Molecular Formula:C44H51N3O10S
InChIKey:BDUXNLWANXBRSW-VREBTVLMSA-N
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Compound Information
Molecular Weight:131.2483
Molecular Formula:C5H13NOSi
InChIKey:LWFWUJCJKPUZLV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:475.559
Molecular Formula:C26H25N3O4S
InChIKey:GYANYTDSBUXYFW-XCEYXQIPSA-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:154.1632
Molecular Formula:C8H10O3
InChIKey:KLIDCXVFHGNTTM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:224.275
Molecular Formula:C8H16O5S
InChIKey:CHAHFVCHPSPXOE-JAJWTYFOSA-N
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Compound Information
Molecular Weight:570.695
Molecular Formula:C34H34O6S
InChIKey:YEAMEHHMSHCNQJ-PBNHZRHQSA-N
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Compound Information
Molecular Weight:494.598
Molecular Formula:C25H34O8S
InChIKey:BAXPCHNYZQDSQR-BNTQGOHGSA-N
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Compound Information
Molecular Weight:431.588
Molecular Formula:C22H29O6S
InChIKey:Not Available
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Compound Information
Molecular Weight:832.7646
Molecular Formula:C36H44N6O17
InChIKey:MNZJKFMVWPEHKL-UQXGWIIUSA-N
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Compound Information
Molecular Weight:1492.8723
Molecular Formula:C93H109N3O14
InChIKey:CQXJEEJQTWIDIR-BSOXXXCHSA-N
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Compound Information
Molecular Weight:442.4138
Molecular Formula:C20H26O11
InChIKey:NUTOOKKKLKYWGZ-BDUQCRIQSA-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:509.45
Molecular Formula:C20H22F3NO9S
InChIKey:NIXSFPHTOXTPOW-QBMGXIFZSA-N
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Compound Information
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:Not Available
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Compound Information
Molecular Weight:439.44
Molecular Formula:C18H21N3O8S
InChIKey:QZAPEKNXCMBZGF-FCHITHBASA-N
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Compound Information
Molecular Weight:1047.297
Molecular Formula:C61H74O13S
InChIKey:BCLWQEYGDBRGLS-XMFQCKQGSA-N
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Compound Information
Molecular Weight:418.503
Molecular Formula:C22H26O6S
InChIKey:UGQVKEFTDVLTBX-UKOYBOBQSA-N
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:MSHFRERJPWKJFX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1191.3581
Molecular Formula:C70H78O17
InChIKey:BONZRURNSQFOQK-NKDOOVSUSA-N
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Compound Information
Molecular Weight:508.626
Molecular Formula:C29H32O6S
InChIKey:HOPJJYXGUGPOFD-KWPJUXILSA-N
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Compound Information
Molecular Weight:329.2696
Molecular Formula:C12H18F3NO6
InChIKey:XOSAVNHBDGZOFQ-ZEBDFXRSSA-N
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Compound Information
Molecular Weight:100.1589
Molecular Formula:C6H12O
InChIKey:Not Available
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Compound Information
Molecular Weight:508.583
Molecular Formula:C28H28O7S
InChIKey:KREMPEPMTULIKX-JSWHLCMFSA-N
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Compound Information
Molecular Weight:152.2334
Molecular Formula:C10H16O
InChIKey:VLLNJDMHDJRNFK-CHIWXEEVSA-N
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Compound Information
Molecular Weight:129.2432
Molecular Formula:C8H19N
InChIKey:JGFZNNIVVJXRND-UHFFFAOYSA-N
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Compound Information
Molecular Weight:705.769
Molecular Formula:C34H43NO13S
InChIKey:QMUHCDUDVMNJLW-BBMFVHLNSA-N
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Compound Information
Molecular Weight:453.5307
Molecular Formula:C25H31N3O5
InChIKey:GMFDGYQLGDQXDQ-FXEFVXDJSA-N
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Compound Information
Molecular Weight:685.033
Molecular Formula:C36H36Cl3NO6
InChIKey:LMICALCPRSCSMO-BGSSSCFASA-N
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Compound Information
Molecular Weight:914.0491
Molecular Formula:C53H59N3O11
InChIKey:MCNSMQGTKCDVGK-GFBQXBDPSA-N
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Compound Information
Molecular Weight:426.62
Molecular Formula:C4F6HgO4
InChIKey:Not Available
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Compound Information
Molecular Weight:464.5501
Molecular Formula:C28H32O6
InChIKey:Not Available
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Compound Information
Molecular Weight:322.3514
Molecular Formula:C14H26O8
InChIKey:CCAVTOKCJUCGIM-OJMFKOBASA-N
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Compound Information
Molecular Weight:629.633
Molecular Formula:C33H27NO10S
InChIKey:DQGPEFOBMAXYJC-OCOQZWCCSA-N
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Compound Information
Molecular Weight:476.6038
Molecular Formula:C30H36O5
InChIKey:JGOHAMQPLGGOLX-XAZDILKDSA-N
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Compound Information
Molecular Weight:652.7695
Molecular Formula:C34H52O12
InChIKey:MIDYUSLOPNUFTA-ZGLCYIBRSA-N
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Compound Information
Molecular Weight:351.3511
Molecular Formula:C17H21NO7
InChIKey:ZSAKUEWNPLLEBD-QCODTGAPSA-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:886.1111
Molecular Formula:C52H59NO10Si
InChIKey:COILOZMAILLHRT-UVKGIYGOSA-N
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Compound Information
Molecular Weight:130.2279
Molecular Formula:C8H18O
InChIKey:KBPLFHHGFOOTCA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:764.7253
Molecular Formula:C39H40O16
InChIKey:DIAXIAALSWTMAH-WMVOTRCESA-N
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Compound Information
Molecular Weight:608.817
Molecular Formula:C33H40O7SSi
InChIKey:AOWXRZZWENKUKS-BJXSZEKMSA-N
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Compound Information
Molecular Weight:408.421
Molecular Formula:C16H24O10S
InChIKey:OAMDASJUUKVAHG-RKFKRFPCSA-N
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Compound Information
Molecular Weight:1174.6249
Molecular Formula:C72H95N3O9Si
InChIKey:QCSXEIARPSDUPX-WGRXPSKXSA-N
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Compound Information
Molecular Weight:648.7393
Molecular Formula:C37H44O10
InChIKey:NMYWFBKYXBSXCB-APPFDUHZSA-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:755.808
Molecular Formula:C38H49N3O13
InChIKey:DDFYVFTXTZYDJX-GFBPWCMOSA-N
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Compound Information
Molecular Weight:430.4462
Molecular Formula:C20H30O10
InChIKey:JUNKMUAPKFNXQJ-WENZLKBRSA-N
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Compound Information
Molecular Weight:973.1543
Molecular Formula:C61H64O11
InChIKey:UHYRNNZUUNTTTE-ZMBNZCPTSA-N
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Compound Information
Molecular Weight:260.2836
Molecular Formula:C12H20O6
InChIKey:Not Available
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Compound Information
Molecular Weight:84.933
Molecular Formula:CH2Cl2
InChIKey:YMWUJEATGCHHMB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:862.2296
Molecular Formula:C56H79NO6
InChIKey:VGQDEZWBNAHYNG-YGDURPQOSA-N
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Compound Information
Molecular Weight:326.3847
Molecular Formula:C17H26O6
InChIKey:MAPJXBYFJAQRMN-UUAJXVIYSA-N
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Compound Information
Molecular Weight:232.321
Molecular Formula:C12H8OS2
InChIKey:NYVGTLXTOJKHJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:146.2273
Molecular Formula:C8H18O2
InChIKey:Not Available
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Compound Information
Molecular Weight:348.3026
Molecular Formula:C14H20O10
InChIKey:FEQXFAYSNRWXDW-RKQHYHRCSA-N
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Compound Information
Molecular Weight:919.0607
Molecular Formula:C51H66O15
InChIKey:CNSYUFFMPJIPKE-YXFLXFAMSA-N
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Compound Information
Molecular Weight:584.636
Molecular Formula:C33H28O8S
InChIKey:NEFOOVSJKFYXPY-OCOQZWCCSA-N
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Compound Information
Molecular Weight:1499.6
Molecular Formula:C78H82O26S2
InChIKey:MXDCQPBLTCXXKT-QTBMEJQKSA-N
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Compound Information
Molecular Weight:782.981
Molecular Formula:C46H54O9S
InChIKey:ZWMHKTGAPUASEU-FXSNOCCASA-N
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Compound Information
Molecular Weight:1001.292
Molecular Formula:C62H80O11
InChIKey:ULFCCWULIXNCTP-BFNPBNRDSA-N
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Compound Information
Molecular Weight:873.9819
Molecular Formula:C51H55NO12
InChIKey:JBUHBQVOBMOGRX-LUWHRSMISA-N
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Compound Information
Molecular Weight:1003.1772
Molecular Formula:C56H74O16
InChIKey:CRAXOBLVCOTSDV-GYJNMVCQSA-N
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Compound Information
Molecular Weight:74.1216
Molecular Formula:C4H10O
InChIKey:DKGAVHZHDRPRBM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:542.685
Molecular Formula:C33H34O5S
InChIKey:LCXKCJJIRDBXPD-MRRLEEDCSA-N
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Compound Information
Molecular Weight:264.363
Molecular Formula:C13H12O2S2
InChIKey:AUBYFXQFOLVHFE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:512.7205
Molecular Formula:C32H48O5
InChIKey:QPZKHDKCCNQMHX-XSDGYPEXSA-N
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Compound Information
Molecular Weight:587.56
Molecular Formula:C33H32O5Se
InChIKey:HQMKPOWFMJBNAX-NMVLBWOISA-N
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Compound Information
Molecular Weight:388.6694
Molecular Formula:C27H48O
InChIKey:QYIXCDOBOSTCEI-QCYZZNICSA-N
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Compound Information
Molecular Weight:1844.0446
Molecular Formula:C108H114O27
InChIKey:LBYNKELOTMFCLG-AZNUEXMJSA-N
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Compound Information
Molecular Weight:525.529
Molecular Formula:C22H27N3O10S
InChIKey:XDZLMFDLWVCZMA-FOFUSGEMSA-N
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Compound Information
Molecular Weight:907.8345
Molecular Formula:C46H44F3NO15
InChIKey:KUGLUHKCPIERIE-NPAWNNFHSA-N
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Compound Information
Molecular Weight:247.4189
Molecular Formula:C17H29N
InChIKey:IDOFMGSESVXXQI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.2077
Molecular Formula:C8H12N4
InChIKey:OZAIFHULBGXAKX-VAWYXSNFSA-N
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Compound Information
Molecular Weight:678.831
Molecular Formula:C38H46O9S
InChIKey:MFIQDSHOHNZNTJ-ZLSKIIIKSA-N
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Compound Information
Molecular Weight:560.6326
Molecular Formula:C30H40O10
InChIKey:CLILWTXUSCZVRZ-PHQFLWEHSA-N
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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:897.0583
Molecular Formula:C55H60O11
InChIKey:BBWPMUKQLZXTPI-TTWHMWBKSA-N
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Compound Information
Molecular Weight:934.0354
Molecular Formula:C56H55NO12
InChIKey:YXNVQVYODXHUEW-GHEAFEOBSA-N
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Compound Information
Molecular Weight:500.5806
Molecular Formula:C28H36O8
InChIKey:WQVDUIVWPOQIOB-RSFKBIFASA-N
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Compound Information
Molecular Weight:79.0999
Molecular Formula:C5H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:938.86
Molecular Formula:C46H51IO11S
InChIKey:BYDTWKKKLGHJRH-OVNSXCNGSA-N
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Compound Information
Molecular Weight:431.4804
Molecular Formula:C26H25NO5
InChIKey:WQYIETDVEJEHCP-UCSBTNPJSA-N
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Compound Information
Molecular Weight:755.8493
Molecular Formula:C43H49NO11
InChIKey:FZKZIZWNWZQYTH-GINISLAKSA-N
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Compound Information
Molecular Weight:458.567
Molecular Formula:C25H30O6S
InChIKey:MRQCYFSWHAWNPZ-RWAVZYIXSA-N
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Compound Information
Molecular Weight:791.774
Molecular Formula:C40H48Cl2O10S
InChIKey:VJBIQYIIGSXYFF-BWJACHKYSA-N
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Compound Information
Molecular Weight:168.0378
Molecular Formula:C3H2F6O
InChIKey:BYEAHWXPCBROCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:55.0785
Molecular Formula:C3H5N
InChIKey:Not Available
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Compound Information
Molecular Weight:307.3019
Molecular Formula:C14H17N3O5
InChIKey:WCSBCLMCXJSBOJ-FAYOZSNISA-N
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Compound Information
Molecular Weight:781.8435
Molecular Formula:C44H47NO12
InChIKey:LHNJGCFBENAVDL-GINISLAKSA-N
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Compound Information
Molecular Weight:558.684
Molecular Formula:C33H34O6S
InChIKey:NITIAVWSKDBMKZ-WWHGLGARSA-N
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Compound Information
Molecular Weight:450.522
Molecular Formula:C24H34O8
InChIKey:YYKJZEHIWWDNCX-CDJZJNNCSA-N
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Compound Information
Molecular Weight:542.685
Molecular Formula:C33H34O5S
InChIKey:FGXZOIOFEDCCKA-CEDPUOIZSA-N
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Compound Information
Molecular Weight:614.889
Molecular Formula:C35H38O4S2Si
InChIKey:HIVIWBZWHOGOSZ-YVQLPJAOSA-N
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Compound Information
Molecular Weight:362.3292
Molecular Formula:C15H22O10
InChIKey:UYWUMFGDPBMNCA-UXXRCYHCSA-N
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Compound Information
Molecular Weight:556.622
Molecular Formula:C26H36O11S
InChIKey:XQBXTWLFGWLJBC-KVKIQERZSA-N
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Compound Information
Molecular Weight:358.408
Molecular Formula:C19H18O5S
InChIKey:CYQOZUYUJVAQPS-KIVCEEGUSA-N
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Compound Information
Molecular Weight:715.7839
Molecular Formula:C37H49NO13
InChIKey:RCGAIHLETXIDEH-HBNYWQCRSA-N
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Compound Information
Molecular Weight:1351.3983
Molecular Formula:C77H74O22
InChIKey:IODRSQLJOTXZAK-WWBTWSLTSA-N
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Compound Information
Molecular Weight:600.721
Molecular Formula:C35H36O7S
InChIKey:STWMYSLJNXSGMP-ZFERNWMGSA-N
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Compound Information
Molecular Weight:494.642
Molecular Formula:C29H34O5S
InChIKey:AZQPSLVUJGSMNT-RQKPWJHBSA-N
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Compound Information
Molecular Weight:238.303
Molecular Formula:C12H14O3S
InChIKey:IVYXBTJSQASMFP-GKMMUAHYSA-N
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Compound Information
Molecular Weight:632.763
Molecular Formula:C36H40O8S
InChIKey:POEWNNMPXAVNJT-OCULRSJVSA-N
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Compound Information
Molecular Weight:721.684
Molecular Formula:C36H42Cl2O9S
InChIKey:APPWRDYVBBVDLD-JKBFEQALSA-N
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Compound Information
Molecular Weight:385.437
Molecular Formula:C19H19N3O4S
InChIKey:HQUROUFKKPKZML-RWLNFDPSSA-N
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Compound Information
Molecular Weight:658.704
Molecular Formula:C33H29F3O7S2
InChIKey:AQWCHTORLANVHE-OEZYNDFSSA-N
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Compound Information
Molecular Weight:404.477
Molecular Formula:C21H24O6S
InChIKey:ANYFVFWLIAUUAL-ZCFSCSEQSA-N
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Compound Information
Molecular Weight:768.911
Molecular Formula:C44H48O10S
InChIKey:LMJCFQJPQXENNY-YDKNCYAVSA-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:166.1553
Molecular Formula:C6H15O3P
InChIKey:BDZBKCUKTQZUTL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:334.3637
Molecular Formula:C18H22O6
InChIKey:ZSNYQENLWQYSRK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:698.7979
Molecular Formula:C41H46O10
InChIKey:CBQZNJZABIWUCK-RZJQWKCISA-N
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Compound Information
Molecular Weight:1121.25
Molecular Formula:C67H60O14S
InChIKey:REFKLBBWKJUQNO-LSOIYURESA-N
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Compound Information
Molecular Weight:540.669
Molecular Formula:C33H32O5S
InChIKey:KDTRYCJSIFGZHI-NMVLBWOISA-N
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Compound Information
Molecular Weight:642.801
Molecular Formula:C38H42O7S
InChIKey:UDUBXMQUUWNPOR-APQALGDJSA-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:415.4795
Molecular Formula:C23H29NO6
InChIKey:POXMMSHWVBSCKK-JLMDMGSGSA-N
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Compound Information
Molecular Weight:1646.972
Molecular Formula:C98H107N3O18S
InChIKey:PGLWEUSRMXHPLF-LOPFYSHZSA-N
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Compound Information
Molecular Weight:542.685
Molecular Formula:C33H34O5S
InChIKey:IMFQDHOUWBKNSN-PRYJAXSFSA-N
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Compound Information
Molecular Weight:506.524
Molecular Formula:C27H22O8S
InChIKey:KNAFDGPTMBATIC-QZTJDOEJSA-N
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Compound Information
Molecular Weight:690.8205
Molecular Formula:C43H46O8
InChIKey:SJAKRXPSUHPLHS-HVJQSLJKSA-N
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Compound Information
Molecular Weight:669.654
Molecular Formula:C28H35N3O14S
InChIKey:FITZTFJUZKAYAM-PQTXMOTQSA-N
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Compound Information
Molecular Weight:68.0773
Molecular Formula:C3H4N2
InChIKey:RAXXELZNTBOGNW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:480.596
Molecular Formula:C26H24O5S2
InChIKey:XOENQONCCVFCQL-NBSKPMDHSA-N
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Compound Information
Molecular Weight:1118.1833
Molecular Formula:C60H67N3O18
InChIKey:ZJGVTDGOKTZSBW-PCHDKAPDSA-N
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Compound Information
Molecular Weight:462.5342
Molecular Formula:C28H30O6
InChIKey:CVHUOBYFXKHVJR-XXDTVXIHSA-N
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Compound Information
Molecular Weight:134.97
Molecular Formula:Cl2O2S
InChIKey:YBBRCQOCSYXUOC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:207.319
Molecular Formula:AgClO4
InChIKey:YDHABVNRCBNRNZ-UHFFFAOYSA-M
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Compound Information
Molecular Weight:816.9736
Molecular Formula:C50H56O10
InChIKey:NFTFVJNTGIFXNH-MTVICHNHSA-N
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Compound Information
Molecular Weight:612.8272
Molecular Formula:C37H44O6Si
InChIKey:PTUOHXMVVREBBG-YGMGGQQPSA-N
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Compound Information
Molecular Weight:632.808
Molecular Formula:C40H40O5S
InChIKey:IKCMSYGNAFDJNX-PLLMGOPLSA-N
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Compound Information
Molecular Weight:664.651
Molecular Formula:C32H40O15
InChIKey:ZRETTXQFRLXTDF-IQLKFJAHSA-N
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Compound Information
Molecular Weight:624.783
Molecular Formula:C32H48O10S
InChIKey:VBHQHJWENQBJRF-MZULQBAQSA-N
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Compound Information
Molecular Weight:548.222
Molecular Formula:CeH8N8O18
InChIKey:XMPZTFVPEKAKFH-UHFFFAOYSA-P
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Compound Information
Molecular Weight:344.423
Molecular Formula:C16H24O6S
InChIKey:QOSRDJGTZGPDCZ-LMLPIDESSA-N
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Compound Information
Molecular Weight:586.6714
Molecular Formula:C35H38O8
InChIKey:JEGWIULCAXMOSP-VLCQNZNESA-N
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Compound Information
Molecular Weight:195.2151
Molecular Formula:C10H13NO3
InChIKey:MFYJBAQONVFIFC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:550.781
Molecular Formula:C31H38O5SSi
InChIKey:WELODGFNYGCHSE-LLQHYSMESA-N
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