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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-01 21:22:50 UTC

Update Date

2021-09-26 22:49:00 UTC

HMDB ID

HMDB0242590

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid

Description

(2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid, also known as trans-caftarate, 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 (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2r,3r)-2-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0242590
     RDKit          3D
(2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
    0.6775   -0.0423   -0.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -0.5652    0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -0.6674    1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -0.3338    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893    0.3234   -0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518    0.6390   -1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9580    1.3399   -2.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2470    1.7397   -2.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9795    2.4313   -3.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382    1.4496   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1594    1.8650   -0.7748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220    0.7679   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -1.1217    1.3614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7145   -1.0291    0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2690   -2.3897    0.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022   -3.3745    1.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350   -2.5478    0.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -0.1798    1.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -0.6798    2.9762 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9289    0.0348    1.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9636   -0.2582    1.7499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319    0.5378   -0.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564   -1.2029    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -0.6522    1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618    0.3124   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4525    1.5420   -3.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5485    2.6460   -4.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5666    1.6366    0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6107    0.5536    0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7161   -0.5034   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3512   -2.8071    0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117    0.8131    1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287   -1.0874    3.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1904    0.8098   -0.6905 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  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  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END

  Mrv1533004171504512D          

 22 22  0  0  0  0            999 V2000
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 O   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   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    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   -2.0625    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
   -2.1434   -2.0625    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
   -2.8579   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    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
  7  5  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
  3 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  2 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242590

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=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)

> <INCHI_KEY>
SWGKAHCIOQPKFW-UHFFFAOYSA-N

> <FORMULA>
C13H12O9

> <MOLECULAR_WEIGHT>
312.23

> <EXACT_MASS>
312.048131966

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.108849045141756

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242590
     RDKit          3D
(2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
    0.6775   -0.0423   -0.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -0.5652    0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -0.6674    1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -0.3338    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893    0.3234   -0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518    0.6390   -1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9580    1.3399   -2.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2470    1.7397   -2.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9795    2.4313   -3.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382    1.4496   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1594    1.8650   -0.7748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220    0.7679   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -1.1217    1.3614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7145   -1.0291    0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2690   -2.3897    0.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022   -3.3745    1.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350   -2.5478    0.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -0.1798    1.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -0.6798    2.9762 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9289    0.0348    1.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9636   -0.2582    1.7499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319    0.5378   -0.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564   -1.2029    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -0.6522    1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618    0.3124   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4525    1.5420   -3.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5485    2.6460   -4.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5666    1.6366    0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6107    0.5536    0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7161   -0.5034   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3512   -2.8071    0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117    0.8131    1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287   -1.0874    3.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1904    0.8098   -0.6905 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  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  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.335  -1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336  -3.850   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.002  -6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
CONECT   17    3   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    2   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0242590
HETATM    1  O1  UNL     1       0.677  -0.042  -0.443  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.316  -0.565   0.638  1.00  0.00           C  
HETATM    3  C2  UNL     1      -0.984  -0.667   1.202  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.143  -0.334   0.882  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.789   0.323  -0.220  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.252   0.639  -1.441  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.958   1.340  -2.434  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.247   1.740  -2.202  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.980   2.431  -3.149  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.838   1.450  -0.996  1.00  0.00           C  
HETATM   11  O3  UNL     1      -6.159   1.865  -0.775  1.00  0.00           O  
HETATM   12  C9  UNL     1      -4.122   0.768  -0.055  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.418  -1.122   1.361  1.00  0.00           O  
HETATM   14  C10 UNL     1       2.714  -1.029   0.816  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.269  -2.390   0.688  1.00  0.00           C  
HETATM   16  O5  UNL     1       2.602  -3.374   1.039  1.00  0.00           O  
HETATM   17  O6  UNL     1       4.535  -2.548   0.174  1.00  0.00           O  
HETATM   18  C12 UNL     1       3.606  -0.180   1.709  1.00  0.00           C  
HETATM   19  O7  UNL     1       3.742  -0.680   2.976  1.00  0.00           O  
HETATM   20  C13 UNL     1       4.929   0.035   1.071  1.00  0.00           C  
HETATM   21  O8  UNL     1       5.964  -0.258   1.750  1.00  0.00           O  
HETATM   22  O9  UNL     1       5.032   0.538  -0.222  1.00  0.00           O  
HETATM   23  H1  UNL     1      -0.956  -1.203   2.236  1.00  0.00           H  
HETATM   24  H2  UNL     1      -2.934  -0.652   1.683  1.00  0.00           H  
HETATM   25  H3  UNL     1      -1.262   0.312  -1.661  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.452   1.542  -3.358  1.00  0.00           H  
HETATM   27  H5  UNL     1      -4.548   2.646  -4.036  1.00  0.00           H  
HETATM   28  H6  UNL     1      -6.567   1.637   0.123  1.00  0.00           H  
HETATM   29  H7  UNL     1      -4.611   0.554   0.890  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.716  -0.503  -0.167  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.351  -2.807   0.727  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.112   0.813   1.777  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.629  -1.087   3.163  1.00  0.00           H  
HETATM   34  H12 UNL     1       4.190   0.810  -0.690  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

HMDB0242590
     RDKit          3D
(2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid
 34 34  0  0  0  0  0  0  0  0999 V2000
    0.6775   -0.0423   -0.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3163   -0.5652    0.6380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9845   -0.6674    1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428   -0.3338    0.8820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7893    0.3234   -0.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2518    0.6390   -1.4411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9580    1.3399   -2.4336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2470    1.7397   -2.2022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9795    2.4313   -3.1495 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8382    1.4496   -0.9964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1594    1.8650   -0.7748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1220    0.7679   -0.0554 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -1.1217    1.3614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7145   -1.0291    0.8161 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2690   -2.3897    0.6878 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6022   -3.3745    1.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5350   -2.5478    0.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6062   -0.1798    1.7093 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7416   -0.6798    2.9762 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9289    0.0348    1.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9636   -0.2582    1.7499 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319    0.5378   -0.2218 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9564   -1.2029    2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9341   -0.6522    1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2618    0.3124   -1.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4525    1.5420   -3.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5485    2.6460   -4.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5666    1.6366    0.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6107    0.5536    0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7161   -0.5034   -0.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3512   -2.8071    0.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1117    0.8131    1.7771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6287   -1.0874    3.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1904    0.8098   -0.6905 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  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  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioate	Generator
trans-Caftarate	HMDB
2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioate	HMDB

Chemical Formula

C₁₃H₁₂O₉

Average Molecular Weight

312.23

Monoisotopic Molecular Weight

312.048131966

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC(C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=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)

InChI Key

SWGKAHCIOQPKFW-UHFFFAOYSA-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

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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	28.11 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
DeepCCS	[M+H]+	165.32	30932474
DeepCCS	[M-H]-	162.962	30932474
DeepCCS	[M-2H]-	195.848	30932474
DeepCCS	[M+Na]+	171.413	30932474
AllCCS	[M+H]+	167.3	32859911
AllCCS	[M+H-H2O]+	164.3	32859911
AllCCS	[M+NH4]+	170.0	32859911
AllCCS	[M+Na]+	170.8	32859911
AllCCS	[M-H]-	165.6	32859911
AllCCS	[M+Na-2H]-	165.5	32859911
AllCCS	[M+HCOO]-	165.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid	OC(C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O)C(O)=O	5083.3	Standard polar	33892256
(2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid	OC(C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O)C(O)=O	2680.1	Standard non polar	33892256
(2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid	OC(C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O)C(O)=O	2898.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-4910000000-8ead661f3e371747bc39	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_3_5) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_3_6) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_3_7) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid GC-MS (TMS_3_8) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid 10V, Positive-QTOF	splash10-03di-0941000000-dffcec2519e8e8c3f95f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid 20V, Positive-QTOF	splash10-03di-0900000000-c4455e5be5330e3a63f5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid 40V, Positive-QTOF	splash10-01p9-0900000000-7ecc2ca7f29b2b87c59c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid 10V, Negative-QTOF	splash10-03di-2922000000-26fb657c11ea5cd25385	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid 20V, Negative-QTOF	splash10-000i-4910000000-e35a7c46ed1ac711f639	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid 40V, Negative-QTOF	splash10-000i-3900000000-289dbaa5e055c4d8dc97	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26463578

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Caftaric acid

METLIN ID

Not Available

PubChem Compound

53398694

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for (2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid (HMDB0242590)

MOL for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

3D MOL for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

3D SDF for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

3D-SDF for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

PDB for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

3D PDB for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

SMILES for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

INCHI for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

Structure for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

3D Structure for HMDB0242590 ((2R,3R)-2-[3-(3,4-Dihydroxyphenyl)prop-2-enoyloxy]-3-hydroxybutanedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra