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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 22:59:36 UTC

Update Date

2021-09-23 22:59:37 UTC

HMDB ID

HMDB0303060

Secondary Accession Numbers

None

Metabolite Identification

Common Name

cis-Caftaric acid

Description

Cis-caftaric acid, also known as (2s,3r)-cis-caffeoyl tartaric acid or cis-caftarate, belongs to coumaric acids and derivatives class of compounds. Those 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. Cis-caftaric acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Cis-caftaric acid can be found in common grape, which makes cis-caftaric acid a potential biomarker for the consumption of this food product.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1533007131513492D          

 26 26  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 10 17  1  6  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 22  9  1  0  0  0  0
 11 22  1  1  0  0  0
 23  2  1  0  0  0  0
 24  4  1  0  0  0  0
 10 25  1  6  0  0  0
 11 26  1  6  0  0  0
M  END

HMDB0303060
     RDKit          3D
cis-Caftaric acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.0459    2.1702   -2.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576    1.3282   -1.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8983    0.9766   -2.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445    0.1470   -2.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9551   -0.6683   -1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9586   -1.1955   -0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1982   -1.8742    0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646   -2.0338    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6705   -2.7102    2.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5062   -1.5146    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8211   -1.6625    1.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -0.8592   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7225    0.9904   -0.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    1.3981    0.1535 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5930    2.1556    1.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5113    2.6036    2.1301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2850    2.3780    1.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8503    0.3166    0.4767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9220    0.9265    1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4053   -0.2789   -0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -0.9124   -1.5928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7447   -0.1921   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920    1.5165   -3.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6470    0.0832   -3.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0620   -1.1917   -0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504   -2.2630    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438   -2.8843    3.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0893   -2.1237    1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568   -0.4423   -1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    2.1228   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960    1.8421    2.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586   -0.4445    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3161    1.6174    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2475    0.6787   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  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  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 12  5  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  6
 17 31  1  0
 18 32  1  1
 19 33  1  0
 22 34  1  0
M  END


  Mrv1533007131513492D          

 26 26  0  0  1  0            999 V2000
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  1  0  0  0  0
  6  5  2  0  0  0  0
  7  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  1  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  2  0  0  0  0
 10 17  1  6  0  0  0
 18 12  2  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21 13  1  0  0  0  0
 22  9  1  0  0  0  0
 11 22  1  1  0  0  0
 23  2  1  0  0  0  0
 24  4  1  0  0  0  0
 10 25  1  6  0  0  0
 11 26  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0303060

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(/[H])C1=CC(O)=C(O)C=C1)C(=O)O[C@]([H])(C(O)=O)[C@@]([H])(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2-/t10-,11+/m1/s1

> <INCHI_KEY>
SWGKAHCIOQPKFW-ADAMHKFESA-N

> <FORMULA>
C13H12O9

> <MOLECULAR_WEIGHT>
312.23

> <EXACT_MASS>
312.048131966

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.400632642045238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

> <ALOGPS_LOGP>
1.68

> <JCHEM_LOGP>
0.5979601859999999

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.484001795143949

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9580286110976193

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3456129955412335

> <JCHEM_POLAR_SURFACE_AREA>
161.59

> <JCHEM_REFRACTIVITY>
69.7429

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303060
     RDKit          3D
cis-Caftaric acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.0459    2.1702   -2.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576    1.3282   -1.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8983    0.9766   -2.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445    0.1470   -2.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9551   -0.6683   -1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9586   -1.1955   -0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1982   -1.8742    0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646   -2.0338    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6705   -2.7102    2.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5062   -1.5146    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8211   -1.6625    1.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -0.8592   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7225    0.9904   -0.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    1.3981    0.1535 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5930    2.1556    1.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5113    2.6036    2.1301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2850    2.3780    1.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8503    0.3166    0.4767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9220    0.9265    1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4053   -0.2789   -0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -0.9124   -1.5928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7447   -0.1921   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920    1.5165   -3.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6470    0.0832   -3.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0620   -1.1917   -0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504   -2.2630    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438   -2.8843    3.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0893   -2.1237    1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568   -0.4423   -1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    2.1228   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960    1.8421    2.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586   -0.4445    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3161    1.6174    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2475    0.6787   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  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  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 12  5  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  6
 17 31  1  0
 18 32  1  1
 19 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -5.335   3.080   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.335   0.000   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       1.334  -0.770   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -1.334  -0.770   0.000  0.00  0.00           H+0
CONECT    1    3    6                                                       
CONECT    2    4    6   23                                                  
CONECT    3    1    7                                                       
CONECT    4    2    9   24                                                  
CONECT    5    6    8                                                       
CONECT    6    1    2    5                                                  
CONECT    7    3    8   14                                                  
CONECT    8    5    7   15                                                  
CONECT    9    4   16   22                                                  
CONECT   10   11   12   17   25                                             
CONECT   11   10   13   22   26                                             
CONECT   12   10   18   19                                                  
CONECT   13   11   20   21                                                  
CONECT   14    7                                                            
CONECT   15    8                                                            
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22    9   11                                                       
CONECT   23    2                                                            
CONECT   24    4                                                            
CONECT   25   10                                                            
CONECT   26   11                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

COMPND    HMDB0303060
HETATM    1  O1  UNL     1      -1.046   2.170  -2.313  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.258   1.328  -1.721  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.898   0.977  -2.486  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.844   0.147  -2.219  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.955  -0.668  -1.049  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.959  -1.196  -0.297  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.198  -1.874   0.910  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.465  -2.034   1.378  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.670  -2.710   2.577  1.00  0.00           O  
HETATM   10  C8  UNL     1       3.506  -1.515   0.639  1.00  0.00           C  
HETATM   11  O3  UNL     1       4.821  -1.663   1.089  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.259  -0.859  -0.527  1.00  0.00           C  
HETATM   13  O4  UNL     1      -0.723   0.990  -0.506  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.860   1.398   0.153  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.593   2.156   1.402  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.511   2.604   2.130  1.00  0.00           O  
HETATM   17  O6  UNL     1      -0.285   2.378   1.781  1.00  0.00           O  
HETATM   18  C12 UNL     1      -2.850   0.317   0.477  1.00  0.00           C  
HETATM   19  O7  UNL     1      -3.922   0.926   1.137  1.00  0.00           O  
HETATM   20  C13 UNL     1      -3.405  -0.279  -0.767  1.00  0.00           C  
HETATM   21  O8  UNL     1      -2.664  -0.912  -1.593  1.00  0.00           O  
HETATM   22  O9  UNL     1      -4.745  -0.192  -1.117  1.00  0.00           O  
HETATM   23  H1  UNL     1       0.992   1.516  -3.482  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.647   0.083  -3.009  1.00  0.00           H  
HETATM   25  H3  UNL     1      -0.062  -1.192  -0.632  1.00  0.00           H  
HETATM   26  H4  UNL     1       0.350  -2.263   1.453  1.00  0.00           H  
HETATM   27  H5  UNL     1       3.544  -2.884   3.009  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.089  -2.124   1.923  1.00  0.00           H  
HETATM   29  H7  UNL     1       4.057  -0.442  -1.127  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.405   2.123  -0.523  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.096   1.842   2.562  1.00  0.00           H  
HETATM   32  H10 UNL     1      -2.459  -0.444   1.170  1.00  0.00           H  
HETATM   33  H11 UNL     1      -4.316   1.617   0.552  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.247   0.679  -1.185  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   23
CONECT    4    5   24
CONECT    5    6    6   12
CONECT    6    7   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   27
CONECT   10   11   12   12
CONECT   11   28
CONECT   12   29
CONECT   13   14
CONECT   14   15   18   30
CONECT   15   16   16   17
CONECT   17   31
CONECT   18   19   20   32
CONECT   19   33
CONECT   20   21   21   22
CONECT   22   34
END

HMDB0303060
     RDKit          3D
cis-Caftaric acid
 34 34  0  0  0  0  0  0  0  0999 V2000
   -1.0459    2.1702   -2.3130 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2576    1.3282   -1.7208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8983    0.9766   -2.4858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8445    0.1470   -2.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9551   -0.6683   -1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9586   -1.1955   -0.2974 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1982   -1.8742    0.9104 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4646   -2.0338    1.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6705   -2.7102    2.5766 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5062   -1.5146    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8211   -1.6625    1.0891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2592   -0.8592   -0.5265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7225    0.9904   -0.5058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    1.3981    0.1535 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5930    2.1556    1.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5113    2.6036    2.1301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2850    2.3780    1.7810 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8503    0.3166    0.4767 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9220    0.9265    1.1370 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4053   -0.2789   -0.7673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6643   -0.9124   -1.5928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7447   -0.1921   -1.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9920    1.5165   -3.4815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6470    0.0832   -3.0090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0620   -1.1917   -0.6325 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3504   -2.2630    1.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5438   -2.8843    3.0094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0893   -2.1237    1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0568   -0.4423   -1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4053    2.1228   -0.5231 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0960    1.8421    2.5619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586   -0.4445    1.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3161    1.6174    0.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2475    0.6787   -1.1848 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  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  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 20 22  1  0
 12  5  1  0
  3 23  1  0
  4 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 14 30  1  6
 17 31  1  0
 18 32  1  1
 19 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3R)-cis-Caffeoyl tartaric acid	ChEBI
cis-Caftaric acid	ChEBI
(2S,3R)-cis-Caffeoyl tartarate	Generator
cis-Caftarate	Generator
(2S,3R)-cis-Caftarate	Generator

Chemical Formula

C₁₃H₁₂O₉

Average Molecular Weight

312.23

Monoisotopic Molecular Weight

312.048131966

IUPAC Name

(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

Traditional Name

(2S,3R)-2-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/[H])C1=CC(O)=C(O)C=C1)C(=O)O[C@]([H])(C(O)=O)[C@@]([H])(O)C(O)=O

InChI Identifier

InChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2-/t10-,11+/m1/s1

InChI Key

SWGKAHCIOQPKFW-ADAMHKFESA-N

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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid ester
Coumaric acid or derivatives
Tricarboxylic acid or derivatives
Styrene
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Sugar acid
Fatty acid ester
Phenol
Beta-hydroxy acid
Fatty acyl
Benzenoid
Hydroxy acid
Alpha-hydroxy acid
Monosaccharide
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

catechols (CHEBI:76082 )
cinnamate ester (CHEBI:76082 )
dicarboxylic acid (CHEBI:76082 )
tetraric acid derivative (CHEBI:76082 )

Ontology

Not Available

Common grape (FooDB: FOOD00204)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.68	ALOGPS
logP	0.6	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	2.96	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.59 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	69.74 m³·mol⁻¹	ChemAxon
Polarizability	27.4 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	167.672	32859911
AllCCS	[M+H-H2O]+	164.607	32859911
AllCCS	[M+Na]+	171.32	32859911
AllCCS	[M+NH4]+	170.507	32859911
AllCCS	[M-H]-	165.674	32859911
AllCCS	[M+Na-2H]-	165.601	32859911
AllCCS	[M+HCOO]-	165.643	32859911
DeepCCS	[M+H]+	169.385	30932474
DeepCCS	[M-H]-	166.99	30932474
DeepCCS	[M-2H]-	199.924	30932474
DeepCCS	[M+Na]+	176.286	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 10V, Positive-QTOF	splash10-03dj-0973000000-1a96d8a708695d13762e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 20V, Positive-QTOF	splash10-03gr-2940000000-a24c1bc2573e378ccd7e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 40V, Positive-QTOF	splash10-0540-4900000000-55b90a17ab1875f9bb88	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 10V, Negative-QTOF	splash10-0409-3982000000-aabe941096f73c4a6cd1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 20V, Negative-QTOF	splash10-02dr-3940000000-9757ec14c725e63e898e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 40V, Negative-QTOF	splash10-03mi-3910000000-aec72816b3809d559efe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 10V, Positive-QTOF	splash10-03di-0953000000-73e8456dc90c46f75a48	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 20V, Positive-QTOF	splash10-03di-0910000000-f57e0a85c0c0b23de9d5	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 40V, Positive-QTOF	splash10-01qi-0900000000-c2b1f17714cf93428742	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 10V, Negative-QTOF	splash10-01t9-9845000000-8fac8da9308f88f4517f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 20V, Negative-QTOF	splash10-000i-4920000000-674af8a072e4e7b09d49	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - cis-Caftaric acid 40V, Negative-QTOF	splash10-0f80-3900000000-a422c010a9d9a7346f8f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB007549

KNApSAcK ID

Not Available

Chemspider ID

30785782

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72551521

PDB ID

Not Available

ChEBI ID

76082

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for cis-Caftaric acid (HMDB0303060)

MOL for HMDB0303060 (cis-Caftaric acid)

3D MOL for HMDB0303060 (cis-Caftaric acid)

3D SDF for HMDB0303060 (cis-Caftaric acid)

3D-SDF for HMDB0303060 (cis-Caftaric acid)

PDB for HMDB0303060 (cis-Caftaric acid)

3D PDB for HMDB0303060 (cis-Caftaric acid)

SMILES for HMDB0303060 (cis-Caftaric acid)

INCHI for HMDB0303060 (cis-Caftaric acid)

Structure for HMDB0303060 (cis-Caftaric acid)

3D Structure for HMDB0303060 (cis-Caftaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra