ACD/Labs10051214052D

 25 26  0  0  1  0  0  0  0  0  1 V2000
   15.3894  -14.3326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5413  -14.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5413  -16.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3894  -16.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2374  -16.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2374  -14.9969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6933  -16.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8452  -16.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   21.1313  -16.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8452  -14.9969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2833  -16.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4352  -16.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2833  -18.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5872  -16.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4352  -18.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5872  -18.3108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7396  -16.3170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7396  -18.9756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0541  -13.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3894  -18.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0851  -16.9817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7246  -13.1802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3894  -12.0283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3955  -13.1802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  1  0  0  0  0
  1 20  1  6  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  3  7  1  1  0  0  0
  5  4  1  0  0  0  0
  4 21  1  6  0  0  0
  6  5  1  0  0  0  0
  5 22  1  6  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 11  8  2  0  0  0  0
 10  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  2  0  0  0  0
 18 15  1  0  0  0  0
 17 16  1  0  0  0  0
 19 17  1  0  0  0  0
  1 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <ID>
CHEBI:16112

> <NAME>
chlorogenic acid

> <DEFINITION>
A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:3625; CHEBI:13972; CHEBI:23145

> <SYNONYM>
trans-5-O-Caffeoyl-D-quinate; Chlorogenic acid; Chlorogenate; Caffeoyl quinic acid; [1S-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid; 5-O-(3,4-Dihydroxycinnamoyl)-L-quinic acid; 3-O-Caffeoylquinic acid; 3-Caffeoylquinic acid; 3-(3,4-Dihydroxycinnamoyl)quinic acid

> <IUPAC_NAME>
edit(1S,3R,4R,5R)-3-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

> <FORMULA>
C16H18O9

> <MASS>
354.30870

> <MONOISOTOPIC_MASS>
354.09508

> <CHARGE>
0

> <SMILES>
O[C@@H]1C[C@](O)(C[C@@H](OC(=O)\C=C\c2ccc(O)c(O)c2)[C@@H]1O)C(O)=O

> <INCHI>
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1

> <INCHIKEY>
CWVRJTMFETXNAD-JUHZACGLSA-N

> <CAS_REGISTRY_NUMBER>
327-97-9

> <REAXYS_REGISTRY_NUMBER>
2017157

> <KEGG_COMPOUND_ACCESSION>
C00852

> <KNAPSACK_ACCESSION>
C00002724

> <METACYC_ACCESSION>
CAFFEOYLQUINATE

> <WIKIPEDIA_ACCESSION>
Chlorogenic_acid

> <PUBMED_CITATION>
16507475; 22770225

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