Standard Article

Chiral Synthons by Ester Hydrolysis Catalyzed by Pig Liver Esterase

  1. Masaji Ohno,
  2. Masami Otsuka

Published Online: 15 OCT 2004

DOI: 10.1002/0471264180.or037.01

Organic Reactions

Organic Reactions

How to Cite

Ohno, M. and Otsuka, M. 2004. Chiral Synthons by Ester Hydrolysis Catalyzed by Pig Liver Esterase. Organic Reactions. 37:1:1–55.

Author Information

  1. University of Tokyo, Faculty of Pharmaceutical Sciences, Bunkyo-ku, Tokyo, Japan

Publication History

  1. Published Online: 15 OCT 2004

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Abstract

Development of efficient methodology to produce an optically pure enantiomer is of fundamental importance, particularly for the synthesis of biologically active natural products. Optically active compounds can be obtained by three different approaches, that is, resolution of racemates, use of a chiral pool or “chiron” (which are enantiomerically pure synthons), or asymmetric synthesis. Of these, one of the more challenging tasks involves asymmetric synthesis, which may be carried out either enzymatically or nonenzymatically. Whereas the nonenzymatic method enables us to introduce a chiral center with either a stoichiometric or catalytic amount of a chiral compound, the enzymatic method uses biological systems, such as microorganisms or isolated enzymes, to create the center of asymmetry. The purpose of this chapter is to survey asymmetric synthesis via the production of enantiomerically pure or enriched organic molecules by the enzymatic method focusing on the use of a hydrolytic enzyme, pig liver esterase (PLE; Enzyme Commission classification number, E.C. 3.1.1.1).

Enzymes are classified into the following six groups based on the reactions they catalyze:

  1. Oxidoreductase (oxidation–reduction reactions);

  2. Transferase (transfer of functional groups);

  3. Hydrolase (hydrolysis reactions);

  4. Lyase (addition to double bonds or the reverse);

  5. Isomerase (isomerization reaction); and

  6. Ligase (formation of bonds coupled with pyrophosphate bond cleavage of ATP).

Virtually all biochemical transformations are catalyzed in vivo by these six groups, and the biochemical aspects of these enzymes have been studied in detail. However, the practical utility of these enzymes in organic synthesis remains to be further exploited and refined. The ability of a substrate to associate with an enzyme is also one of the most significant problems. In some cases, these problems have been overcome and several enzyme reactions have been successfully used on a large scale.

An enzyme reaction generally takes place when an intimate interaction between the reactant and the chiral catalyst (enzyme protein) is realized. This enzyme–substrate complex is designated as the Michaelis complex. Certain amino acid residues of the enzyme form a three-dimensional structure as the active site. This site often contains reactive groups of the amino acids such as amino, mercapto, hydroxyl, carbonyl, carboxyl, guanidino, or imidazolyl. When the substrate is bound to the active site in a specific orientation, enantiotopic groups or faces of the substrate molecule are discriminated by the chiral enzyme. This discrimination is sufficiently sensitive to differentiate between the two hydrogen atoms in a methylene group. Thus the reaction proceeds stereospecifically. The enzyme can also distinguish among several substrates competing for an active site. Such substrate specificity is sometimes strict and sometimes broad. Synthetically useful enzymes should accept a wide range of substrates and exhibit high stereospecificity. Many enzymes meet these criteria, and PLE is one of them.

Keywords:

  • chiral synthons;
  • pig liver esterase;
  • hydrolysis;
  • prochiral diesters;
  • enantioselective hydrolysis;
  • kinetic resolution;
  • glutarate derivatives;
  • bicycloheptene derivatives;
  • cyclohexene dicarboxylates;
  • hydrolytic enzymes;
  • oxidoreductases;
  • nonenzymatic methods;
  • diesters;
  • scope;
  • limitations;
  • experimental procedures;
  • diols;
  • prochiral malonates;
  • cyclopropanecarboxylates;
  • dicarboxylates;
  • esters

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  1. 1 - 250
Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:UKPIBFMHHUEUQR-DTORHVGOSA-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:0
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:LNIQYJXNDLAPKL-WHFBIAKZSA-N
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Compound Information
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:BOVPVRGRPPYECC-RQJHMYQMSA-N
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:FVUHGTQDOMGZOT-NTSWFWBYSA-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:170.2057
Molecular Formula:C9H14O3
InChIKey:NLFMWTUWKKWNIG-JGVFFNPUSA-N
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Compound Information
Molecular Weight:176.1672
Molecular Formula:C7H12O5
InChIKey:UNHGPASVFNKZNR-ZETCQYMHSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:155.1943
Molecular Formula:C8H13NO2
InChIKey:PIPIDLZHXZUHIZ-NKWVEPMBSA-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:84.1164
Molecular Formula:C5H8O
InChIKey:ICMWSAALRSINTC-UHFFFAOYSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:245.2292
Molecular Formula:C10H15NO6
InChIKey:KWSPJRXIPVXYGD-MYJAWHEDSA-N
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Compound Information
Molecular Weight:368.4263
Molecular Formula:C21H24N2O4
InChIKey:XMIDKFZMIIYMSR-VQTJNVASSA-N
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Compound Information
Molecular Weight:354.481
Molecular Formula:C20H34O5
InChIKey:GMVPRGQOIOIIMI-DWKJAMRDSA-N
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Compound Information
Molecular Weight:180.179
Molecular Formula:C5H8O5S
InChIKey:LKOZEGJLDIXKIU-NSHDSACASA-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:382.4098
Molecular Formula:C21H22N2O5
InChIKey:BBTUUSONTSSVJB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:134.1736
Molecular Formula:C6H14O3
InChIKey:AHHQDHCTHYTBSV-UHFFFAOYSA-N
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Compound Information
Molecular Weight:106.42
Molecular Formula:Pd
InChIKey:KDLHZDBZIXYQEI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:SQFQEQDRLAZVJQ-KNVOCYPGSA-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:368.5075
Molecular Formula:C21H36O5
InChIKey:QLPYHQHJKMTHED-KHBONWNZSA-N
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Compound Information
Molecular Weight:316.201
Molecular Formula:C21H21BO2
InChIKey:CDHSXQNARNMZRD-NRFANRHFSA-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:156.1791
Molecular Formula:C8H12O3
InChIKey:HCYYWWWVLDNESR-NKWVEPMBSA-N
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Compound Information
Molecular Weight:143.1406
Molecular Formula:C6H9NO3
InChIKey:RXHXPUPRSNKIGG-BYPYZUCNSA-N
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Compound Information
Molecular Weight:255.3101
Molecular Formula:C13H21NO4
InChIKey:LYRHVVUOSWUYOL-ZJUUUORDSA-N
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:KYGFHAUBFNTXFK-RITPCOANSA-N
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Compound Information
Molecular Weight:343.6522
Molecular Formula:C17H37NO2Si2
InChIKey:FCUTZTNNGGQITI-CQSZACIVSA-N
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Compound Information
Molecular Weight:212.1993
Molecular Formula:C10H12O5
InChIKey:JYJBURATEMWQOS-KVFPUHGPSA-N
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Compound Information
Molecular Weight:226.1828
Molecular Formula:C10H10O6
InChIKey:ZQMBDVYNNZGSNY-KVFPUHGPSA-N
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:WEPHXFVXUXMCLE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:168.2328
Molecular Formula:C10H16O2
InChIKey:XLOPRKKSAJMMEW-SFYZADRCSA-N
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Compound Information
Molecular Weight:41.0519
Molecular Formula:C2H3N
InChIKey:WEVYAHXRMPXWCK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:174.1513
Molecular Formula:C7H10O5
InChIKey:SHSCEGGPAKMDDE-CRCLSJGQSA-N
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Compound Information
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:XFLSEYYPOYRKKC-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:114.1424
Molecular Formula:C6H10O2
InChIKey:YHTLGFCVBKENTE-YFKPBYRVSA-N
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Compound Information
Molecular Weight:272.321
Molecular Formula:C11H16N2O4S
InChIKey:WKDDRNSBRWANNC-ATRFCDNQSA-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:107.123
Molecular Formula:C6H14LiN
InChIKey:ZCSHNCUQKCANBX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:184.1892
Molecular Formula:C9H12O4
InChIKey:Not Available
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Compound Information
Molecular Weight:123.1525
Molecular Formula:C7H9NO
InChIKey:IHROAFZNBVGGFN-NTSWFWBYSA-N
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Compound Information
Molecular Weight:160.1678
Molecular Formula:C7H12O4
InChIKey:YGNOTSXXQFFAFO-CRCLSJGQSA-N
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Compound Information
Molecular Weight:264.14
Molecular Formula:C8H11NO4Se
InChIKey:DHVFVZFXGFBFMR-JCGDXUMPSA-N
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Compound Information
Molecular Weight:282.2891
Molecular Formula:C14H18O6
InChIKey:XMOOKAONUQUBNL-BJPCUFFRSA-N
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Compound Information
Molecular Weight:253.80894
Molecular Formula:I2
InChIKey:PNDPGZBMCMUPRI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:284.215
Molecular Formula:C12H28O4Ti
InChIKey:VXUYXOFXAQZZMF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:206.1932
Molecular Formula:C8H14O6
InChIKey:YSAVZVORKRDODB-PHDIDXHHSA-N
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Compound Information
Molecular Weight:198.2158
Molecular Formula:C10H14O4
InChIKey:DVVAGRMJGUQHLI-OCAPTIKFSA-N
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Compound Information
Molecular Weight:664.4325
Molecular Formula:C21H28N7O14P2
InChIKey:BAWFJGJZGIEFAR-NNYOXOHSSA-O
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Compound Information
Molecular Weight:270.2354
Molecular Formula:C12H14O7
InChIKey:GDUYDEZMEPGLDX-UYXSQOIJSA-N
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Compound Information
Molecular Weight:258.3538
Molecular Formula:C14H26O4
InChIKey:NWFOXUHSGKNDMV-CQSZACIVSA-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:186.162
Molecular Formula:C8H10O5
InChIKey:SOSNFEHKRDJYIS-WDSKDSINSA-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:263.2526
Molecular Formula:C11H13N5O3
InChIKey:XUGWUUDOWNZAGW-VDAHYXPESA-N
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Compound Information
Molecular Weight:203.1925
Molecular Formula:C8H13NO5
InChIKey:CIVMRRCEEWJXAY-CSMHCCOUSA-N
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Compound Information
Molecular Weight:214.2152
Molecular Formula:C10H14O5
InChIKey:POTNFJDLTHITRH-RQJHMYQMSA-N
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Compound Information
Molecular Weight:239.2279
Molecular Formula:C10H13N3O4
InChIKey:DUJGMZAICVPCBJ-VDAHYXPESA-N
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Compound Information
Molecular Weight:144.1253
Molecular Formula:C6H8O4
InChIKey:IRRAJLZEAOBJIV-IUYQGCFVSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:274.2671
Molecular Formula:C12H18O7
InChIKey:DSOYGARCIUGVBU-MGYJEQJYSA-N
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Compound Information
Molecular Weight:257.4014
Molecular Formula:C12H23NO3Si
InChIKey:SMTDMUZNKKWFDF-VIFPVBQESA-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:387.7047
Molecular Formula:C19H41NO3Si2
InChIKey:XJEZTAALYIGUHX-ANGDWKNPSA-N
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Compound Information
Molecular Weight:200.1886
Molecular Formula:C9H12O5
InChIKey:GMKJWKXCHOWVDN-BQBZGAKWSA-N
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Compound Information
Molecular Weight:248.94
Molecular Formula:C8H18OSn
InChIKey:JGFBRKRYDCGYKD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:248.2795
Molecular Formula:C9H20N4O4
InChIKey:IKHFJPZQZVMLRH-RNFRBKRXSA-N
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Compound Information
Molecular Weight:184.2322
Molecular Formula:C10H16O3
InChIKey:NHFLCQGAZJUTFN-VHSXEESVSA-N
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Compound Information
Molecular Weight:224.253
Molecular Formula:C12H16O4
InChIKey:AFSHMUUJMODEQX-LBPRGKRZSA-N
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Compound Information
Molecular Weight:263.2891
Molecular Formula:C14H17NO4
InChIKey:PPRLCASKVDQSEK-NWDGAFQWSA-N
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Compound Information
Molecular Weight:148.1571
Molecular Formula:C6H12O4
InChIKey:KJTLQQUUPVSXIM-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:183.2044
Molecular Formula:C9H13NO3
InChIKey:NEJBWENICROWTO-JGVFFNPUSA-N
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Compound Information
Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:TXVYGBGEKZBRST-NTSWFWBYSA-N
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Compound Information
Molecular Weight:229.1867
Molecular Formula:C9H11NO6
InChIKey:FFLUMYXAPXARJP-JBBNEOJLSA-N
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Compound Information
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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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:204.243
Molecular Formula:C8H12O4S
InChIKey:UBSQOGXCPUUNJW-OLQVQODUSA-N
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Compound Information
Molecular Weight:202.2475
Molecular Formula:C10H18O4
InChIKey:MYBLGPBPMJJRAB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:102.0886
Molecular Formula:C4H6O3
InChIKey:ZVNYKZKUBKIIAH-VKHMYHEASA-N
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Compound Information
Molecular Weight:116.1152
Molecular Formula:C5H8O3
InChIKey:DQHYBNWZWWGNQB-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:118.1742
Molecular Formula:C6H14O2
InChIKey:SXFJDZNJHVPHPH-UHFFFAOYSA-N
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Compound Information
Molecular Weight:142.1525
Molecular Formula:C7H10O3
InChIKey:IJDYOKVVRXZCFD-NKWVEPMBSA-N
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Compound Information
Molecular Weight:228.2417
Molecular Formula:C11H16O5
InChIKey:WMZIMDPTSNILLM-OCAPTIKFSA-N
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Compound Information
Molecular Weight:194.206
Molecular Formula:C6H10O5S
InChIKey:WXSZTIDGDMKUHQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:220.314
Molecular Formula:C10H8N2S2
InChIKey:HAXFWIACAGNFHA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:268.2625
Molecular Formula:C13H16O6
InChIKey:ATMXYIGZOXNJIT-FTEGDLIOSA-N
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Compound Information
Molecular Weight:188.2209
Molecular Formula:C9H16O4
InChIKey:MPZVITRUKTWADX-VIFPVBQESA-N
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Compound Information
Molecular Weight:146.1858
Molecular Formula:C10H10O
InChIKey:BWHOZHOGCMHOBV-BQYQJAHWSA-N
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Compound Information
Molecular Weight:214.2152
Molecular Formula:C10H14O5
InChIKey:HGUPYDNRFPCLSC-KVFPUHGPSA-N
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Compound Information
Molecular Weight:185.2203
Molecular Formula:C9H15NO3
InChIKey:MULFOTZDRHUZLB-UHFFFAOYSA-N
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Compound Information
Molecular Weight:368.3832
Molecular Formula:C20H20N2O5
InChIKey:BSWUHWZVMBPALP-DLBZAZTESA-N
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Compound Information
Molecular Weight:200.1886
Molecular Formula:C9H12O5
InChIKey:RTYHOZSKZMLUKB-UCROKIRRSA-N
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Compound Information
Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:YIJLMTNDXYVGPQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:324.352
Molecular Formula:C14H16N2O5S
InChIKey:OXRGPSLVPTUXTM-SBPHBMPXSA-N
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Compound Information
Molecular Weight:22.98976928
Molecular Formula:Na
InChIKey:MPMYQQHEHYDOCL-UHFFFAOYSA-N
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Compound Information
Molecular Weight:278.97
Molecular Formula:C12H16Sn
InChIKey:UHDACKUVWSAVMD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:90.121
Molecular Formula:C4H10O2
InChIKey:CIHOLLKRGTVIJN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:240.2955
Molecular Formula:C13H20O4
InChIKey:FJKRNFUCYXXENY-PHIMTYICSA-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:100.1158
Molecular Formula:C5H8O2
InChIKey:OZYHLCOUAISLLG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:154.1632
Molecular Formula:C8H10O3
InChIKey:MUTGBJKUEZFXGO-OLQVQODUSA-N
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Compound Information
Molecular Weight:250.11
Molecular Formula:C7H9NO4Se
InChIKey:IJVOQSSXRKAOBC-ALEPSDHESA-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:192.2542
Molecular Formula:C12H16O2
InChIKey:HPLHNHIWNLNAEZ-NSHDSACASA-N
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Compound Information
Molecular Weight:226.2689
Molecular Formula:C12H18O4
InChIKey:UXTXISBRNRVIED-TXEJJXNPSA-N
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Compound Information
Molecular Weight:158.1519
Molecular Formula:C7H10O4
InChIKey:JBVOSZYUSFDYIN-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:157.1671
Molecular Formula:C7H11NO3
InChIKey:FQOWJGGXNSRNJS-YFKPBYRVSA-N
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Compound Information
Molecular Weight:158.1519
Molecular Formula:C7H10O4
InChIKey:DLSMGFKPSMYVFW-CRCLSJGQSA-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:134.197
Molecular Formula:C5H10O2S
InChIKey:HOIOPKDVXGTVDY-UHFFFAOYSA-N
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Compound Information
Molecular Weight:1839.55
Molecular Formula:C93H96Cl4O6P6Ru2
InChIKey:MDWOSAZADBEUQE-FNJWYWORSA-J
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Compound Information
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:JVZYMEXLQMHFCI-WDSKDSINSA-N
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Compound Information
Molecular Weight:56.1063
Molecular Formula:C4H8
InChIKey:VQTUBCCKSQIDNK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:164.1134
Molecular Formula:C5H8O6
InChIKey:GBJFSZCDZHSAOP-GBXIJSLDSA-N
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Compound Information
Molecular Weight:188.1779
Molecular Formula:C8H12O5
InChIKey:BWLYYAVHHIIVJW-PHDIDXHHSA-N
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Compound Information
Molecular Weight:459.834
Molecular Formula:C22H45NO3SSi2
InChIKey:FFKOQKWSQVVMBT-SELCWUDQSA-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:262.2855
Molecular Formula:C18H15P
InChIKey:RIOQSEWOXXDEQQ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:58.0791
Molecular Formula:C3H6O
InChIKey:YOXHCYXIAVIFCZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:251.2419
Molecular Formula:C10H13N5O3
InChIKey:OFEZSBMBBKLLBJ-BAJZRUMYSA-N
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Compound Information
Molecular Weight:243.3748
Molecular Formula:C11H21NO3Si
InChIKey:SJKOWWRLDMKGHW-QMMMGPOBSA-N
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Compound Information
Molecular Weight:190.217
Molecular Formula:C7H10O4S
InChIKey:XKYSZEYBYRIVIM-CRCLSJGQSA-N
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Compound Information
Molecular Weight:282.2891
Molecular Formula:C14H18O6
InChIKey:DXRIQNINKGQASV-HLQDMEJYSA-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:116.1583
Molecular Formula:C6H12O2
InChIKey:SMFZAIRMNYPZLI-ZBHICJROSA-N
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Compound Information
Molecular Weight:174.1944
Molecular Formula:C8H14O4
InChIKey:MWWSWNCJAAQPLW-OLQVQODUSA-N
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Compound Information
Molecular Weight:184.2786
Molecular Formula:C10H20N2O
InChIKey:ZGSICHPLDHANQB-JTQLQIEISA-N
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Compound Information
Molecular Weight:42.04
Molecular Formula:CH2N2
InChIKey:YXHKONLOYHBTNS-UHFFFAOYSA-N
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Compound Information
Molecular Weight:226.2689
Molecular Formula:C12H18O4
InChIKey:MNNDHWWDUFABCI-AOOOYVTPSA-N
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Compound Information
Molecular Weight:355.1694
Molecular Formula:C11H18INO4
InChIKey:FURHRYHBRBULPM-HTQZYQBOSA-N
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Compound Information
Molecular Weight:295.2879
Molecular Formula:C14H17NO6
InChIKey:RBOKYBCBRQCEHG-NSHDSACASA-N
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Compound Information
Molecular Weight:307.3416
Molecular Formula:C16H21NO5
InChIKey:YTQBZGHFYIDQON-OLZOCXBDSA-N
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Compound Information
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:AIACXWOETVLBIA-UHFFFAOYSA-N
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Compound Information
Molecular Weight:272.3804
Molecular Formula:C15H28O4
InChIKey:RNGPLCVYJRTJOF-UHFFFAOYSA-N
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Compound Information
Molecular Weight:217.2191
Molecular Formula:C9H15NO5
InChIKey:BLSQTPNEINXHIQ-SSDOTTSWSA-N
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Compound Information
Molecular Weight:178.14
Molecular Formula:C6H10O6
InChIKey:PVRATXCXJDHJJN-ZXZARUISSA-N
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Compound Information
Molecular Weight:385.6889
Molecular Formula:C19H39NO3Si2
InChIKey:CCPHQKRTCHVOAW-HZPDHXFCSA-N
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Compound Information
Molecular Weight:326.3417
Molecular Formula:C16H22O7
InChIKey:OKQMJJMTIOYRGU-KXNHARMFSA-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:310.3423
Molecular Formula:C16H22O6
InChIKey:OEVDRIQUWGDHBD-KGOITJQVSA-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:266.2897
Molecular Formula:C14H18O5
InChIKey:IXOWJPODGHAALN-UHFFFAOYSA-N
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Compound Information
Molecular Weight:108.642
Molecular Formula:C3H9ClSi
InChIKey:IJOOHPMOJXWVHK-UHFFFAOYSA-N
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Compound Information
Molecular Weight:320.3802
Molecular Formula:C18H24O5
InChIKey:POVUBSNFLSMKQG-PMPSAXMXSA-N
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Compound Information
Molecular Weight:21.784
Molecular Formula:BH4Li
InChIKey:UUKMSDRCXNLYOO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:YYUNQECXARGEAQ-CRCLSJGQSA-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:58.0791
Molecular Formula:C3H6O
InChIKey:CSCPPACGZOOCGX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:409.5179
Molecular Formula:C25H31NO4
InChIKey:OSCYXQFRRASKIW-JOCHJYFZSA-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:249.2625
Molecular Formula:C13H15NO4
InChIKey:WGNIWBQMXGJLSC-LLVKDONJSA-N
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Compound Information
Molecular Weight:204.2203
Molecular Formula:C9H16O5
InChIKey:DXBHDBLZPXQALN-XAMCCFCMSA-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:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Information
Molecular Weight:258.2677
Molecular Formula:C12H18O6
InChIKey:ZSZSGMFEOWARCA-DTWKUNHWSA-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:116.1583
Molecular Formula:C6H12O2
InChIKey:OELRMAJYFPFOPY-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:272.2943
Molecular Formula:C13H20O6
InChIKey:SCLLBQYOQNOJAU-AOOOYVTPSA-N
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Compound Information
Molecular Weight:208.2106
Molecular Formula:C11H12O4
InChIKey:WFKWXJMEUOLYOS-KNVOCYPGSA-N
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Compound Information
Molecular Weight:314.088
Molecular Formula:C13H10BF3O3S
InChIKey:RIQHFVSUHYHHKG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:198.1727
Molecular Formula:C9H10O5
InChIKey:FQFNYXKATGMXCK-UCROKIRRSA-N
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Compound Information
Molecular Weight:245.1894
Molecular Formula:C8H11N3O6
InChIKey:GLROOHDFRPQSIO-OGCOERNTSA-N
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Compound Information
Molecular Weight:312.3151
Molecular Formula:C15H20O7
InChIKey:JEHNDZFUIBNVKB-YTWAJWBKSA-N
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Compound Information
Molecular Weight:245.2723
Molecular Formula:C11H19NO5
InChIKey:LUTOGWKCFUKNRU-UHFFFAOYSA-N
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Compound Information
Molecular Weight:277.3157
Molecular Formula:C15H19NO4
InChIKey:VOUOTBJQQLQSCY-BETUJISGSA-N
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Compound Information
Molecular Weight:169.1778
Molecular Formula:C8H11NO3
InChIKey:WYYGPJLHJBZKEX-RQJHMYQMSA-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:188.1779
Molecular Formula:C8H12O5
InChIKey:LPLJNEHCXHAFLB-OLQVQODUSA-N
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Compound Information
Molecular Weight:284.2619
Molecular Formula:C13H16O7
InChIKey:AFBXOZZDIZUARR-YNFQOJQRSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:JYVXNLLUYHCIIH-LURJTMIESA-N
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Compound Information
Molecular Weight:212.2423
Molecular Formula:C11H16O4
InChIKey:JPCXBIVQPMASSR-BDAKNGLRSA-N
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Compound Information
Molecular Weight:194.184
Molecular Formula:C10H10O4
InChIKey:WPPRQTOKYRDUCP-NTSWFWBYSA-N
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Compound Information
Molecular Weight:342.368
Molecular Formula:C14H18N2O6S
InChIKey:FWWJFXYMDLTDNO-BBCPMLLOSA-N
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Compound Information
Molecular Weight:47.9982
Molecular Formula:O3
InChIKey:CBENFWSGALASAD-UHFFFAOYSA-N
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Compound Information
Molecular Weight:222.26
Molecular Formula:C12H28BK
InChIKey:NHEDTYWJTOUTDG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:260.2405
Molecular Formula:C11H16O7
InChIKey:MXBLWWSZXKZEJF-WCMLQCRESA-N
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Compound Information
Molecular Weight:212.2423
Molecular Formula:C11H16O4
InChIKey:HFBPCLWCHWYRIN-DTORHVGOSA-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:259.3742
Molecular Formula:C11H21NO4Si
InChIKey:GYQGXYJCESWTPC-APPZFPTMSA-N
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Compound Information
Molecular Weight:410.4629
Molecular Formula:C23H26N2O5
InChIKey:MRLHYSSQMIEBTI-UHFFFAOYSA-N
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Compound Information
Molecular Weight:190.1938
Molecular Formula:C8H14O5
InChIKey:ANEMYUYZEOZEJW-UHFFFAOYSA-N
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Compound Information
Molecular Weight:182.2594
Molecular Formula:C11H18O2
InChIKey:ITNHSNMLIFFVQC-BDAKNGLRSA-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:355.1694
Molecular Formula:C11H18INO4
InChIKey:FURHRYHBRBULPM-SFYZADRCSA-N
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Compound Information
Molecular Weight:355.1694
Molecular Formula:C11H18INO4
InChIKey:FURHRYHBRBULPM-GVHYBUMESA-N
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Compound Information
Molecular Weight:212.1562
Molecular Formula:C9H8O6
InChIKey:MSLROMSWYHOAMN-BNHYGAARSA-N
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Compound Information
Molecular Weight:265.2685
Molecular Formula:C11H15N5O3
InChIKey:UGRNVLGKAGREKS-GCXDCGAKSA-N
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Compound Information
Molecular Weight:224.253
Molecular Formula:C12H16O4
InChIKey:AFSHMUUJMODEQX-GFCCVEGCSA-N
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Compound Information
Molecular Weight:188.2209
Molecular Formula:C9H16O4
InChIKey:LQLYZPTVIYLWPB-KNVOCYPGSA-N
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Compound Information
Molecular Weight:214.2152
Molecular Formula:C10H14O5
InChIKey:HGUPYDNRFPCLSC-SOSBWXJGSA-N
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Compound Information
Molecular Weight:200.1886
Molecular Formula:C9H12O5
InChIKey:RTYHOZSKZMLUKB-JRTVQGFMSA-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:182.2594
Molecular Formula:C11H18O2
InChIKey:ITNHSNMLIFFVQC-DTWKUNHWSA-N
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Compound Information
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:JVZYMEXLQMHFCI-PHDIDXHHSA-N
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Compound Information
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:AIACXWOETVLBIA-HTQZYQBOSA-N
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Compound Information
Molecular Weight:186.2051
Molecular Formula:C9H14O4
InChIKey:BOVPVRGRPPYECC-RNFRBKRXSA-N
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Compound Information
Molecular Weight:200.2316
Molecular Formula:C10H16O4
InChIKey:AIACXWOETVLBIA-YUMQZZPRSA-N
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Compound Information
Molecular Weight:200.1886
Molecular Formula:C9H12O5
InChIKey:GMKJWKXCHOWVDN-RNFRBKRXSA-N
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Compound Information
Molecular Weight:174.1513
Molecular Formula:C7H10O5
InChIKey:KUESDWMRXPKNPW-WHFBIAKZSA-N
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Compound Information
Molecular Weight:116.1152
Molecular Formula:C5H8O3
InChIKey:DQHYBNWZWWGNQB-SCSAIBSYSA-N
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Compound Information
Molecular Weight:185.2203
Molecular Formula:C9H15NO3
InChIKey:MULFOTZDRHUZLB-SSDOTTSWSA-N
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Compound Information
Molecular Weight:142.1525
Molecular Formula:C7H10O3
InChIKey:IJDYOKVVRXZCFD-RQJHMYQMSA-N
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Compound Information
Molecular Weight:130.1418
Molecular Formula:C6H10O3
InChIKey:JYVXNLLUYHCIIH-ZCFIWIBFSA-N
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Compound Information
Molecular Weight:204.2203
Molecular Formula:C9H16O5
InChIKey:DXBHDBLZPXQALN-WCTZXXKLSA-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:222.2372
Molecular Formula:C12H14O4
InChIKey:PZKVSGUZRFZFAP-LBPRGKRZSA-N
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Compound Information
Molecular Weight:172.1785
Molecular Formula:C8H12O4
InChIKey:LNIQYJXNDLAPKL-CRCLSJGQSA-N
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Compound Information
Molecular Weight:138.1638
Molecular Formula:C8H10O2
InChIKey:Not Available
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Compound Information
Molecular Weight:227.257
Molecular Formula:C11H17NO4
InChIKey:WCJVQIMRZWCGIU-SECBINFHSA-N
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Compound Information
Molecular Weight:236.2637
Molecular Formula:C13H16O4
InChIKey:NKCLMVJSYCXQLT-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:188.2209
Molecular Formula:C9H16O4
InChIKey:IMRWVSSSILYGAW-VIFPVBQESA-N
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Compound Information
Molecular Weight:260.3713
Molecular Formula:C17H24O2
InChIKey:XXADHJZMVHIGLS-HZPDHXFCSA-N
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Compound Information
Molecular Weight:300.3475
Molecular Formula:C15H24O6
InChIKey:ZKJNJTLJUYJFOI-JDGPPOGSSA-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:282.2891
Molecular Formula:C14H18O6
InChIKey:JLHPXBVNNYHQLO-CQSZACIVSA-N
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Compound Information
Molecular Weight:396.4364
Molecular Formula:C22H24N2O5
InChIKey:NFQQKLXLAFETNH-RBUKOAKNSA-N
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Compound Information
Molecular Weight:148.114
Molecular Formula:C5H8O5
InChIKey:BAYPZOAENQTQBK-YFKPBYRVSA-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:254.3221
Molecular Formula:C14H22O4
InChIKey:HYVFXKUAIQVWFZ-TXEJJXNPSA-N
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Compound Information
Molecular Weight:216.2741
Molecular Formula:C11H20O4
InChIKey:DTHLCPJSRSNVLX-UHFFFAOYSA-N
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Compound Information
Molecular Weight:279.2885
Molecular Formula:C14H17NO5
InChIKey:JTEUADNFPJTOPZ-UHFFFAOYSA-N
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Compound Information
Molecular Weight:100.1158
Molecular Formula:C5H8O2
InChIKey:IGRLIBJHDBWKNA-SYDPRGILSA-N
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Compound Information
Molecular Weight:188.264
Molecular Formula:C10H20O3
InChIKey:UBBZVQPPGAGCNC-SNVBAGLBSA-N
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Compound Information
Molecular Weight:250.2903
Molecular Formula:C14H18O4
InChIKey:KGUIOHXCGVQYEG-UHFFFAOYSA-N
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Compound Information
Molecular Weight:296.3157
Molecular Formula:C15H20O6
InChIKey:OTUSIBNNNQOPFN-IZLWQMGWSA-N
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Compound Information
Molecular Weight:99.9943
Molecular Formula:CrO3
InChIKey:WGLPBDUCMAPZCE-UHFFFAOYSA-N
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Compound Information
Molecular Weight:172.2215
Molecular Formula:C9H16O3
InChIKey:YBIXBLXWQMESSO-UHFFFAOYSA-N
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Compound Information
Molecular Weight:350.4923
Molecular Formula:C21H34O4
InChIKey:XZFRIPGNUQRGPI-WBQKLGIQSA-N
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Compound Information
Molecular Weight:214.2582
Molecular Formula:C11H18O4
InChIKey:CJBVAIGVDOVFMK-RKDXNWHRSA-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:206.2362
Molecular Formula:C9H18O5
InChIKey:MRPMDQXJTYDDLM-UHFFFAOYSA-N
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Compound Information
Molecular Weight:382.4098
Molecular Formula:C21H22N2O5
InChIKey:BBTUUSONTSSVJB-HDICACEKSA-N
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Compound Information
Molecular Weight:276.2845
Molecular Formula:C15H16O5
InChIKey:NUPNVWUYFVEAIT-UJJBCWTCSA-N
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Compound Information
Molecular Weight:296.3157
Molecular Formula:C15H20O6
InChIKey:MAFOWEJWYJTBLN-UHFFFAOYSA-N
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