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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-01 02:26:10 UTC

Update Date

2021-09-26 22:48:59 UTC

HMDB ID

HMDB0242519

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid

Description

2,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. Based on a literature review very few articles have been published on 2,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (2r,3r)-2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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


  Mrv1533004201504302D          

 34 35  0  0  0  0            999 V2000
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   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
    2.1434   -6.1875    0.0000 O   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
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    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
    0.0000   -4.1250    0.0000 C   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
    5.0013   -5.3625    0.0000 O   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
    5.7158   -4.1250    0.0000 O   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
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   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
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END

HMDB0242519
     RDKit          3D
(2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid
 52 53  0  0  0  0  0  0  0  0999 V2000
   -3.7520    2.8954   -2.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3720    1.7504   -1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1326    0.5944   -2.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -0.6230   -1.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3100   -1.4984   -1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335   -2.8786   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -3.7707   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9258   -3.3799    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562   -4.3293    1.2187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5881   -2.0678    0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5326   -1.6860    1.3052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.1519   -0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761    1.9199   -1.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5979    3.1128   -0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5362    3.5109    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927    2.7766    1.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    4.6543    0.8611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2198    3.1126   -1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5852    2.0885   -1.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028    1.1203   -1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330    1.1463   -3.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171    0.1189   -1.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    0.1299    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617   -0.8287    0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6476   -1.8690    0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -2.7472    0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4749   -2.6441    2.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2188   -3.5353    3.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7726   -1.5829    2.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -1.4348    4.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0373   -0.7000    2.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    4.4161   -1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1759    5.4684   -1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    4.4667   -0.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0265    0.8126   -3.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9869   -1.1955   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4455   -3.2278   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2461   -4.8127   -0.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4970   -4.0110    1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2974   -0.7081    1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642   -0.1362   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1547    3.9217   -1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    5.2045    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244    3.0718   -2.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968   -0.6339   -1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6618    0.9205    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5934   -1.9735   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9211   -3.5676    0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2808   -3.4491    4.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3503   -0.6923    4.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066    0.1103    2.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6863    3.8118    0.1687 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
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  3
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 18 32  1  0
 32 33  2  0
 32 34  1  0
 12  5  1  0
 31 24  1  0
  3 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 17 43  1  0
 18 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
 26 48  1  0
 28 49  1  0
 30 50  1  0
 31 51  1  0
 34 52  1  0
M  END


  Mrv1533004201504302D          

 34 35  0  0  0  0            999 V2000
    4.2868   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   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
    2.1434   -6.1875    0.0000 O   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
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    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
    0.0000   -4.1250    0.0000 C   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
    5.0013   -5.3625    0.0000 O   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
    5.7158   -4.1250    0.0000 O   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
    8.5737   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -7.4250    0.0000 O   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
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  6  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 10 17  1  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 24 31  1  0  0  0  0
 18 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0242519

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)

> <INCHI_KEY>
YDDGKXBLOXEEMN-UHFFFAOYSA-N

> <FORMULA>
C22H18O12

> <MOLECULAR_WEIGHT>
474.374

> <EXACT_MASS>
474.07982602

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
44.77490905636988

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.0247202606666663

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.684576453831155

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7169409199418117

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283762525890698

> <JCHEM_POLAR_SURFACE_AREA>
208.11999999999998

> <JCHEM_REFRACTIVITY>
113.27239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0242519
     RDKit          3D
(2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid
 52 53  0  0  0  0  0  0  0  0999 V2000
   -3.7520    2.8954   -2.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3720    1.7504   -1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1326    0.5944   -2.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -0.6230   -1.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3100   -1.4984   -1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335   -2.8786   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -3.7707   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9258   -3.3799    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562   -4.3293    1.2187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5881   -2.0678    0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5326   -1.6860    1.3052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.1519   -0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761    1.9199   -1.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5979    3.1128   -0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5362    3.5109    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927    2.7766    1.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    4.6543    0.8611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2198    3.1126   -1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5852    2.0885   -1.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028    1.1203   -1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330    1.1463   -3.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171    0.1189   -1.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    0.1299    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617   -0.8287    0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6476   -1.8690    0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -2.7472    0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4749   -2.6441    2.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2188   -3.5353    3.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7726   -1.5829    2.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -1.4348    4.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0373   -0.7000    2.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    4.4161   -1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1759    5.4684   -1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    4.4667   -0.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0265    0.8126   -3.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9869   -1.1955   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4455   -3.2278   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2461   -4.8127   -0.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4970   -4.0110    1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2974   -0.7081    1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642   -0.1362   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1547    3.9217   -1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    5.2045    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244    3.0718   -2.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968   -0.6339   -1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6618    0.9205    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5934   -1.9735   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9211   -3.5676    0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2808   -3.4491    4.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3503   -0.6923    4.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066    0.1103    2.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6863    3.8118    0.1687 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
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  3
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 18 32  1  0
 32 33  2  0
 32 34  1  0
 12  5  1  0
 31 24  1  0
  3 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 17 43  1  0
 18 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
 26 48  1  0
 28 49  1  0
 30 50  1  0
 31 51  1  0
 34 52  1  0
M  END

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  O   UNK     0       8.002 -12.320   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336 -10.010   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.670 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.004  -9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.338 -10.010   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      17.338 -11.550   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.672 -12.320   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      16.004 -12.320   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      14.670 -11.550   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10                                                       
CONECT   18    4   19   32                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   24                                                       
CONECT   32   18   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

COMPND    HMDB0242519
HETATM    1  O1  UNL     1      -3.752   2.895  -2.545  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.372   1.750  -1.991  1.00  0.00           C  
HETATM    3  C2  UNL     1      -4.133   0.594  -2.282  1.00  0.00           C  
HETATM    4  C3  UNL     1      -4.099  -0.623  -1.948  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.310  -1.498  -1.120  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.634  -2.879  -1.117  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.949  -3.771  -0.348  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.926  -3.380   0.451  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.256  -4.329   1.219  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.588  -2.068   0.475  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.533  -1.686   1.305  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.279  -1.152  -0.304  1.00  0.00           C  
HETATM   13  O4  UNL     1      -2.276   1.920  -1.219  1.00  0.00           O  
HETATM   14  C10 UNL     1      -1.598   3.113  -0.991  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.536   3.511   0.416  1.00  0.00           C  
HETATM   16  O5  UNL     1      -2.093   2.777   1.268  1.00  0.00           O  
HETATM   17  O6  UNL     1      -0.897   4.654   0.861  1.00  0.00           O  
HETATM   18  C12 UNL     1      -0.220   3.113  -1.645  1.00  0.00           C  
HETATM   19  O7  UNL     1       0.585   2.089  -1.149  1.00  0.00           O  
HETATM   20  C13 UNL     1       1.203   1.120  -1.904  1.00  0.00           C  
HETATM   21  O8  UNL     1       1.033   1.146  -3.150  1.00  0.00           O  
HETATM   22  C14 UNL     1       2.017   0.119  -1.240  1.00  0.00           C  
HETATM   23  C15 UNL     1       2.169   0.130   0.064  1.00  0.00           C  
HETATM   24  C16 UNL     1       2.962  -0.829   0.816  1.00  0.00           C  
HETATM   25  C17 UNL     1       3.648  -1.869   0.222  1.00  0.00           C  
HETATM   26  C18 UNL     1       4.382  -2.747   0.988  1.00  0.00           C  
HETATM   27  C19 UNL     1       4.475  -2.644   2.354  1.00  0.00           C  
HETATM   28  O9  UNL     1       5.219  -3.535   3.112  1.00  0.00           O  
HETATM   29  C20 UNL     1       3.773  -1.583   2.935  1.00  0.00           C  
HETATM   30  O10 UNL     1       3.834  -1.435   4.315  1.00  0.00           O  
HETATM   31  C21 UNL     1       3.037  -0.700   2.194  1.00  0.00           C  
HETATM   32  C22 UNL     1       0.387   4.416  -1.314  1.00  0.00           C  
HETATM   33  O11 UNL     1      -0.176   5.468  -1.666  1.00  0.00           O  
HETATM   34  O12 UNL     1       1.571   4.467  -0.619  1.00  0.00           O  
HETATM   35  H1  UNL     1      -5.026   0.813  -3.024  1.00  0.00           H  
HETATM   36  H2  UNL     1      -4.987  -1.195  -2.481  1.00  0.00           H  
HETATM   37  H3  UNL     1      -4.446  -3.228  -1.747  1.00  0.00           H  
HETATM   38  H4  UNL     1      -3.246  -4.813  -0.391  1.00  0.00           H  
HETATM   39  H5  UNL     1      -0.497  -4.011   1.807  1.00  0.00           H  
HETATM   40  H6  UNL     1      -0.297  -0.708   1.314  1.00  0.00           H  
HETATM   41  H7  UNL     1      -1.964  -0.136  -0.228  1.00  0.00           H  
HETATM   42  H8  UNL     1      -2.155   3.922  -1.554  1.00  0.00           H  
HETATM   43  H9  UNL     1      -1.223   5.205   1.649  1.00  0.00           H  
HETATM   44  H10 UNL     1      -0.324   3.072  -2.758  1.00  0.00           H  
HETATM   45  H11 UNL     1       2.497  -0.634  -1.834  1.00  0.00           H  
HETATM   46  H12 UNL     1       1.662   0.920   0.644  1.00  0.00           H  
HETATM   47  H13 UNL     1       3.593  -1.974  -0.848  1.00  0.00           H  
HETATM   48  H14 UNL     1       4.921  -3.568   0.515  1.00  0.00           H  
HETATM   49  H15 UNL     1       5.281  -3.449   4.111  1.00  0.00           H  
HETATM   50  H16 UNL     1       3.350  -0.692   4.775  1.00  0.00           H  
HETATM   51  H17 UNL     1       2.507   0.110   2.684  1.00  0.00           H  
HETATM   52  H18 UNL     1       1.686   3.812   0.169  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   35
CONECT    4    5   36
CONECT    5    6    6   12
CONECT    6    7   37
CONECT    7    8    8   38
CONECT    8    9   10
CONECT    9   39
CONECT   10   11   12   12
CONECT   11   40
CONECT   12   41
CONECT   13   14
CONECT   14   15   18   42
CONECT   15   16   16   17
CONECT   17   43
CONECT   18   19   32   44
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23   23   45
CONECT   23   24   46
CONECT   24   25   25   31
CONECT   25   26   47
CONECT   26   27   27   48
CONECT   27   28   29
CONECT   28   49
CONECT   29   30   31   31
CONECT   30   50
CONECT   31   51
CONECT   32   33   33   34
CONECT   34   52
END

HMDB0242519
     RDKit          3D
(2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid
 52 53  0  0  0  0  0  0  0  0999 V2000
   -3.7520    2.8954   -2.5446 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3720    1.7504   -1.9906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1326    0.5944   -2.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0988   -0.6230   -1.9485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3100   -1.4984   -1.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335   -2.8786   -1.1175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -3.7707   -0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9258   -3.3799    0.4513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2562   -4.3293    1.2187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5881   -2.0678    0.4754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5326   -1.6860    1.3052 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.1519   -0.3038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2761    1.9199   -1.2188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5979    3.1128   -0.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5362    3.5109    0.4155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0927    2.7766    1.2682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    4.6543    0.8611 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2198    3.1126   -1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5852    2.0885   -1.1489 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2028    1.1203   -1.9038 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0330    1.1463   -3.1504 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171    0.1189   -1.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    0.1299    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9617   -0.8287    0.8159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6476   -1.8690    0.2222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3820   -2.7472    0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4749   -2.6441    2.3544 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2188   -3.5353    3.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7726   -1.5829    2.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8341   -1.4348    4.3150 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0373   -0.7000    2.1936 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3873    4.4161   -1.3138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1759    5.4684   -1.6664 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5706    4.4667   -0.6186 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0265    0.8126   -3.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9869   -1.1955   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4455   -3.2278   -1.7469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2461   -4.8127   -0.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4970   -4.0110    1.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2974   -0.7081    1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642   -0.1362   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1547    3.9217   -1.5541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    5.2045    1.6492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3244    3.0718   -2.7585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4968   -0.6339   -1.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6618    0.9205    0.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5934   -1.9735   -0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9211   -3.5676    0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2808   -3.4491    4.1106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3503   -0.6923    4.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5066    0.1103    2.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6863    3.8118    0.1687 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
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  3
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 18 32  1  0
 32 33  2  0
 32 34  1  0
 12  5  1  0
 31 24  1  0
  3 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  0
 17 43  1  0
 18 44  1  0
 22 45  1  0
 23 46  1  0
 25 47  1  0
 26 48  1  0
 28 49  1  0
 30 50  1  0
 31 51  1  0
 34 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-Bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioate	Generator
Chicate	Generator, HMDB
Chicic acid	Generator, HMDB
(-)-L-Chicoric acid	MeSH, HMDB
L-Chicoric acid	MeSH, HMDB
Dicaffeoyltartaric acid	MeSH, HMDB
(-)-Chicoric acid	MeSH, HMDB
2,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid	MeSH, HMDB
Cichoric acid	MeSH, HMDB
(2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioate	Generator

Chemical Formula

C₂₂H₁₈O₁₂

Average Molecular Weight

474.374

Monoisotopic Molecular Weight

474.07982602

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)

InChI Key

YDDGKXBLOXEEMN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monosaccharide
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen 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)

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	3.48	ALOGPS
logP	3.02	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	208.12 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	113.27 m³·mol⁻¹	ChemAxon
Polarizability	44.77 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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]+	194.233	30932474
DeepCCS	[M-H]-	191.838	30932474
DeepCCS	[M-2H]-	224.72	30932474
DeepCCS	[M+Na]+	200.146	30932474
AllCCS	[M+H]+	204.3	32859911
AllCCS	[M+H-H2O]+	202.4	32859911
AllCCS	[M+NH4]+	206.1	32859911
AllCCS	[M+Na]+	206.6	32859911
AllCCS	[M-H]-	199.2	32859911
AllCCS	[M+Na-2H]-	199.6	32859911
AllCCS	[M+HCOO]-	200.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid	OC(=O)C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O	7799.3	Standard polar	33892256
(2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid	OC(=O)C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O	4160.9	Standard non polar	33892256
(2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid	OC(=O)C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(OC(=O)C=CC1=CC=C(O)C(O)=C1)C(O)=O	4509.2	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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0900000000-e4e626822c0d793f1148	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid GC-MS (TMS_3_8) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid GC-MS (TMS_3_9) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid GC-MS (TMS_3_10) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid GC-MS (TMS_4_1) - 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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid 10V, Positive-QTOF	splash10-03fr-0901700000-f4d1776487e047aa09ec	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid 20V, Positive-QTOF	splash10-03di-0900000000-7e0b5ff11e3e8af6c32a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid 40V, Positive-QTOF	splash10-0239-0900000000-ebbea0b5a3285dfafc92	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid 10V, Negative-QTOF	splash10-03di-0941300000-1f4166c12a6d4d660ac6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid 20V, Negative-QTOF	splash10-00l2-0970000000-937eef34bd2f95661490	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid 40V, Negative-QTOF	splash10-000i-0910000000-000e7d8964966a58f859	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

4308294

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5134221

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-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid (HMDB0242519)

MOL for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

3D MOL for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

3D SDF for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

3D-SDF for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

PDB for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

3D PDB for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

SMILES for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

INCHI for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

Structure for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

3D Structure for HMDB0242519 ((2R,3R)-2,3-Bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra