Hmdb loader

Showing metabocard for caffeoylshikimate (HMDB0304282)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 08:36:16 UTC
Update Date2021-09-24 08:36:16 UTC
HMDB IDHMDB0304282
Secondary Accession NumbersNone
Metabolite Identification
Common Namecaffeoylshikimate
Description4-{3-[(3-carboxy-5,6-dihydroxycyclohex-3-en-1-yl)oxy]-3-oxoprop-1-en-1-yl}-2-hydroxybenzen-1-olate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Based on a literature review very few articles have been published on 4-{3-[(3-carboxy-5,6-dihydroxycyclohex-3-en-1-yl)oxy]-3-oxoprop-1-en-1-yl}-2-hydroxybenzen-1-olate.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0304282 (caffeoylshikimate)

  Mrv1533004241518572D          

 24 25  0  0  0  0            999 V2000
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
  3 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
M  CHG  1   9  -1
M  END
Download

3D MOL for HMDB0304282 (caffeoylshikimate)

HMDB0304282
     RDKit          3D
caffeoylshikimate
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.5109    0.8619    2.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0705    0.4788    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3805    0.3008    1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8327   -0.1044    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2383   -0.2782   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238   -0.7142   -1.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9486   -0.9044   -1.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9346   -0.6693   -0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2762   -0.8559   -0.9485 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5391   -0.2331    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5470   -0.0005    1.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188   -0.0434    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247    0.2028    0.6187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3297    0.3187    0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8256    1.3808   -0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3098    1.3919   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278    2.6458   -0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2941    2.6602   -0.2558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3349    3.8299   -0.1217 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.9104    0.2253   -0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173   -1.0132   -0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9037   -2.1566   -0.3645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9192   -1.0302    0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8889   -1.8346   -0.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0496    0.5182    2.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304   -0.3239   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9029   -0.9217   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468   -1.2430   -2.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5211   -1.1721   -1.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3270    0.3200    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9693    0.2919    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549    0.6686    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896    1.2206   -1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937    2.3766    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9836    0.1695   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7250   -1.0523   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8206   -1.9059   -0.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600   -1.4612    1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9919   -1.9441   -1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 23 38  1  0
 24 39  1  0
M  CHG  1  19  -1
M  END
Download

3D SDF for HMDB0304282 (caffeoylshikimate)

  Mrv1533004241518572D          

 24 25  0  0  0  0            999 V2000
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  4 10  1  0  0  0  0
  3 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 13  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
 19 24  1  0  0  0  0
M  CHG  1   9  -1
M  END
> <DATABASE_ID>
HMDB0304282

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C=C(CC(OC(=O)C=CC2=CC(O)=C(O)C=C2)C1O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/p-1

> <INCHI_KEY>
QMPHZIPNNJOWQI-UHFFFAOYSA-M

> <FORMULA>
C16H15O8

> <MOLECULAR_WEIGHT>
335.289

> <EXACT_MASS>
335.077241023

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
31.796585685282942

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylate

> <ALOGPS_LOGP>
0.99

> <JCHEM_LOGP>
0.7866859976666667

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.208550231347209

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.937063432609867

> <JCHEM_PKA_STRONGEST_BASIC>
-3.378175780771425

> <JCHEM_POLAR_SURFACE_AREA>
147.35000000000002

> <JCHEM_REFRACTIVITY>
93.3269

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0304282 (caffeoylshikimate)

HMDB0304282
     RDKit          3D
caffeoylshikimate
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.5109    0.8619    2.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0705    0.4788    1.6449 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3805    0.3008    1.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8327   -0.1044    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2383   -0.2782   -0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238   -0.7142   -1.2656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9486   -0.9044   -1.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9346   -0.6693   -0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2762   -0.8559   -0.9485 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5391   -0.2331    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5470   -0.0005    1.5342 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188   -0.0434    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247    0.2028    0.6187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3297    0.3187    0.6854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8256    1.3808   -0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3098    1.3919   -0.3177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278    2.6458   -0.2312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2941    2.6602   -0.2558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3349    3.8299   -0.1217 O   0  0  0  0  0  1  0  0  0  0  0  0
   -4.9104    0.2253   -0.4239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173   -1.0132   -0.5093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9037   -2.1566   -0.3645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9192   -1.0302    0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8889   -1.8346   -0.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0496    0.5182    2.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1304   -0.3239   -0.5789 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9029   -0.9217   -2.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2468   -1.2430   -2.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5211   -1.1721   -1.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3270    0.3200    2.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9693    0.2919    1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6549    0.6686    1.6960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3896    1.2206   -1.3050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4937    2.3766    0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9836    0.1695   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7250   -1.0523   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8206   -1.9059   -0.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2600   -1.4612    1.3581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9919   -1.9441   -1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 20 35  1  0
 21 36  1  0
 22 37  1  0
 23 38  1  0
 24 39  1  0
M  CHG  1  19  -1
M  END
Download

PDB for HMDB0304282 (caffeoylshikimate)

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O-1
HETATM   10  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.003 -11.550   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      16.004 -12.320   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      16.004  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    4                                                            
CONECT   11    3                                                            
CONECT   12    2   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20                                                            
CONECT   24   19                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END
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3D PDB for HMDB0304282 (caffeoylshikimate)

COMPND    HMDB0304282
HETATM    1  O1  UNL     1      -0.511   0.862   2.734  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.070   0.479   1.645  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.381   0.301   1.396  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.833  -0.104   0.242  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.238  -0.278  -0.003  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.624  -0.714  -1.266  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.949  -0.904  -1.578  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.935  -0.669  -0.651  1.00  0.00           C  
HETATM    9  O2  UNL     1       7.276  -0.856  -0.948  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.539  -0.233   0.610  1.00  0.00           C  
HETATM   11  O3  UNL     1       6.547  -0.001   1.534  1.00  0.00           O  
HETATM   12  C9  UNL     1       4.219  -0.043   0.922  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.925   0.203   0.619  1.00  0.00           O  
HETATM   14  C10 UNL     1      -2.330   0.319   0.685  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.826   1.381  -0.289  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.310   1.392  -0.318  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.028   2.646  -0.231  1.00  0.00           C  
HETATM   18  O5  UNL     1      -6.294   2.660  -0.256  1.00  0.00           O  
HETATM   19  O6  UNL     1      -4.335   3.830  -0.122  1.00  0.00           O1-
HETATM   20  C14 UNL     1      -4.910   0.225  -0.424  1.00  0.00           C  
HETATM   21  C15 UNL     1      -4.117  -1.013  -0.509  1.00  0.00           C  
HETATM   22  O7  UNL     1      -4.904  -2.157  -0.365  1.00  0.00           O  
HETATM   23  C16 UNL     1      -2.919  -1.030   0.381  1.00  0.00           C  
HETATM   24  O8  UNL     1      -1.889  -1.835  -0.155  1.00  0.00           O  
HETATM   25  H1  UNL     1       2.050   0.518   2.204  1.00  0.00           H  
HETATM   26  H2  UNL     1       1.130  -0.324  -0.579  1.00  0.00           H  
HETATM   27  H3  UNL     1       2.903  -0.922  -2.053  1.00  0.00           H  
HETATM   28  H4  UNL     1       5.247  -1.243  -2.559  1.00  0.00           H  
HETATM   29  H5  UNL     1       7.521  -1.172  -1.871  1.00  0.00           H  
HETATM   30  H6  UNL     1       6.327   0.320   2.475  1.00  0.00           H  
HETATM   31  H7  UNL     1       3.969   0.292   1.903  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.655   0.669   1.696  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.390   1.221  -1.305  1.00  0.00           H  
HETATM   34  H10 UNL     1      -2.494   2.377   0.064  1.00  0.00           H  
HETATM   35  H11 UNL     1      -5.984   0.169  -0.449  1.00  0.00           H  
HETATM   36  H12 UNL     1      -3.725  -1.052  -1.569  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.821  -1.906  -0.051  1.00  0.00           H  
HETATM   38  H14 UNL     1      -3.260  -1.461   1.358  1.00  0.00           H  
HETATM   39  H15 UNL     1      -1.992  -1.944  -1.134  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   12
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   10
CONECT    9   29
CONECT   10   11   12   12
CONECT   11   30
CONECT   12   31
CONECT   13   14
CONECT   14   15   23   32
CONECT   15   16   33   34
CONECT   16   17   20   20
CONECT   17   18   18   19
CONECT   20   21   35
CONECT   21   22   23   36
CONECT   22   37
CONECT   23   24   38
CONECT   24   39
END
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SMILES for HMDB0304282 (caffeoylshikimate)

OC1C=C(CC(OC(=O)C=CC2=CC(O)=C(O)C=C2)C1O)C([O-])=O
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INCHI for HMDB0304282 (caffeoylshikimate)

InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/p-1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
4-{3-[(3-carboxy-5,6-dihydroxycyclohex-3-en-1-yl)oxy]-3-oxoprop-1-en-1-yl}-2-hydroxybenzen-1-olic acidGenerator
Caffeoylshikimic acidGenerator
Chemical FormulaC16H15O8
Average Molecular Weight335.289
Monoisotopic Molecular Weight335.077241023
IUPAC Name5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylate
Traditional Name5-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylate
CAS Registry NumberNot Available
SMILES
OC1C=C(CC(OC(=O)C=CC2=CC(O)=C(O)C=C2)C1O)C([O-])=O
InChI Identifier
InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/p-1
InChI KeyQMPHZIPNNJOWQI-UHFFFAOYSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Catechol
  • Styrene
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Cyclitol or derivatives
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Benzenoid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - caffeoylshikimate 10V, Negative-QTOFsplash10-00ku-0449000000-c36daf3ca4914b7cb4e22019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - caffeoylshikimate 20V, Negative-QTOFsplash10-08mi-0921000000-5cfe4605ef580dcc3bd12019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - caffeoylshikimate 40V, Negative-QTOFsplash10-004i-0900000000-181d1a719ec173ff16402019-02-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030709
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74413285
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available