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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 18:36:27 UTC

Update Date

2021-09-23 18:36:27 UTC

HMDB ID

HMDB0302546

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-trans-O-Feruloylglucaric acid

Description

2-trans-o-feruloylglucaric acid belongs to glucuronic acid derivatives class of compounds. Those are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. 2-trans-o-feruloylglucaric acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-trans-o-feruloylglucaric acid can be found in sweet orange, which makes 2-trans-o-feruloylglucaric acid a potential biomarker for the consumption of this food product.

Structure

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

  Mrv0541 02241212532D          

 27 27  0  0  0  0            999 V2000
    3.4367   -0.9398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7222   -0.5273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7222    0.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -0.9398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0078   -1.7648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933   -0.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788   -0.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933    0.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512   -0.5273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8656   -0.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801   -0.5273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656   -1.7648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367   -1.7648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512    5.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512    4.4227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    4.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    4.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2946    4.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2946    3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    2.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    1.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    1.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    0.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    0.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512    0.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    5.2477    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  1  9  1  0  0  0  0
  9 26  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  1 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 22 20  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 17 27  1  0  0  0  0
M  END

HMDB0302546
     RDKit          3D
2-trans-O-Feruloylglucaric acid
 45 45  0  0  0  0  0  0  0  0999 V2000
    6.1162   -1.8945   -3.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2408   -0.7287   -2.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2502   -0.1707   -1.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9972   -0.7181   -1.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9968   -0.1509   -0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -0.7725   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877   -0.3378    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5973   -1.0714    0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410   -2.1266   -0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6732   -0.6335    0.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957   -1.3327    0.9087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1533   -1.7990    2.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1866   -2.4523    2.5751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372   -1.5079    3.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -0.5333    0.4328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1994   -1.3966    0.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067    0.6669    1.2432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5767    1.2318    0.6755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3583    1.7344    1.2909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8804    2.7762    2.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172    2.3223   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    3.5358   -0.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5949    1.5600   -1.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635    1.0067   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387    1.5878   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938    0.9936   -0.9361 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7584    1.5699   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -2.6056   -2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1444   -2.3561   -3.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315   -1.7141   -4.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7594   -1.6134   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5413   -1.7046   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8152    0.5681    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100   -2.2350    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -2.1892    3.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.2639   -0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9560   -1.0117    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225    0.3331    2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821    1.5758    1.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821    1.3998    1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9341    2.4699    3.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    1.5452   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393    1.5113    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7507    2.5131    0.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9887    2.4185   -0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 11 34  1  6
 14 35  1  0
 15 36  1  6
 16 37  1  0
 17 38  1  1
 18 39  1  0
 19 40  1  1
 20 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  1  0
 27 45  1  0
M  END

  Mrv0541 02241212532D          

 27 27  0  0  0  0            999 V2000
    3.4367   -0.9398    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7222   -0.5273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7222    0.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -0.9398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0078   -1.7648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933   -0.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5788   -0.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2933    0.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512   -0.5273    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8656   -0.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801   -0.5273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656   -1.7648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367   -1.7648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512    5.2477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512    4.4227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    4.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    4.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2946    4.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2946    3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    2.7727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    3.1852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    1.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    1.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8656    0.7102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    0.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512    0.2977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5801    5.2477    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  1  0  0  0
  2  4  1  0  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  1  9  1  0  0  0  0
  9 26  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  1 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 22 20  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 17 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302546

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)O[C@H]([C@@H](O)[C@H](O)[C@H](O)C(O)=O)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O11/c1-26-9-6-7(2-4-8(9)17)3-5-10(18)27-14(16(24)25)12(20)11(19)13(21)15(22)23/h2-6,11-14,17,19-21H,1H3,(H,22,23)(H,24,25)/b5-3+/t11-,12-,13-,14+/m0/s1

> <INCHI_KEY>
JZRAOXRUPYISEN-GLJYKRHASA-N

> <FORMULA>
C16H18O11

> <MOLECULAR_WEIGHT>
386.3075

> <EXACT_MASS>
386.084911418

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
35.611338445641906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R)-2,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}hexanedioic acid

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
-0.5168156420000002

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.482487246102858

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.790498100310532

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7314400175836715

> <JCHEM_POLAR_SURFACE_AREA>
191.04999999999995

> <JCHEM_REFRACTIVITY>
86.1502

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.78e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R)-2,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}hexanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302546
     RDKit          3D
2-trans-O-Feruloylglucaric acid
 45 45  0  0  0  0  0  0  0  0999 V2000
    6.1162   -1.8945   -3.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2408   -0.7287   -2.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2502   -0.1707   -1.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9972   -0.7181   -1.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9968   -0.1509   -0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -0.7725   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877   -0.3378    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5973   -1.0714    0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410   -2.1266   -0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6732   -0.6335    0.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957   -1.3327    0.9087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1533   -1.7990    2.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1866   -2.4523    2.5751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372   -1.5079    3.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -0.5333    0.4328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1994   -1.3966    0.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067    0.6669    1.2432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5767    1.2318    0.6755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3583    1.7344    1.2909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8804    2.7762    2.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172    2.3223   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    3.5358   -0.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5949    1.5600   -1.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635    1.0067   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387    1.5878   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938    0.9936   -0.9361 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7584    1.5699   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -2.6056   -2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1444   -2.3561   -3.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315   -1.7141   -4.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7594   -1.6134   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5413   -1.7046   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8152    0.5681    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100   -2.2350    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -2.1892    3.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.2639   -0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9560   -1.0117    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225    0.3331    2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821    1.5758    1.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821    1.3998    1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9341    2.4699    3.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    1.5452   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393    1.5113    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7507    2.5131    0.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9887    2.4185   -0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 11 34  1  6
 14 35  1  0
 15 36  1  6
 16 37  1  0
 17 38  1  1
 18 39  1  0
 19 40  1  1
 20 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  1  0
 27 45  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       6.415  -1.754   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.081  -0.984   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.081   0.556   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.748  -1.754   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       3.748  -3.294   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.414  -0.984   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.080  -1.754   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       2.414   0.556   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.749  -0.984   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.082  -1.754   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.416  -0.984   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       9.082  -3.294   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       6.415  -3.294   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.749   9.796   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.749   8.256   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.082   7.486   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.416   8.256   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.750   7.486   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.750   5.946   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.416   5.176   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.082   5.946   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.416   3.636   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.082   2.866   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.082   1.326   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      10.416   0.556   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       7.749   0.556   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      10.416   9.796   0.000  0.00  0.00           O+0
CONECT    1    2    9   13                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1   26   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1                                                            
CONECT   14   15                                                            
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   16                                                       
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26    9   24                                                       
CONECT   27   17                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

COMPND    HMDB0302546
HETATM    1  C1  UNL     1       6.116  -1.895  -3.168  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.241  -0.729  -2.421  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.250  -0.171  -1.634  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.997  -0.718  -1.496  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.997  -0.151  -0.698  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.694  -0.772  -0.590  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.688  -0.338   0.121  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.597  -1.071   0.145  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.741  -2.127  -0.522  1.00  0.00           O  
HETATM   10  O3  UNL     1      -1.673  -0.634   0.887  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.896  -1.333   0.909  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.153  -1.799   2.290  1.00  0.00           C  
HETATM   13  O4  UNL     1      -4.187  -2.452   2.575  1.00  0.00           O  
HETATM   14  O5  UNL     1      -2.237  -1.508   3.281  1.00  0.00           O  
HETATM   15  C10 UNL     1      -4.080  -0.533   0.433  1.00  0.00           C  
HETATM   16  O6  UNL     1      -5.199  -1.397   0.512  1.00  0.00           O  
HETATM   17  C11 UNL     1      -4.407   0.667   1.243  1.00  0.00           C  
HETATM   18  O7  UNL     1      -5.577   1.232   0.675  1.00  0.00           O  
HETATM   19  C12 UNL     1      -3.358   1.734   1.291  1.00  0.00           C  
HETATM   20  O8  UNL     1      -3.880   2.776   2.105  1.00  0.00           O  
HETATM   21  C13 UNL     1      -3.117   2.322  -0.050  1.00  0.00           C  
HETATM   22  O9  UNL     1      -3.373   3.536  -0.318  1.00  0.00           O  
HETATM   23  O10 UNL     1      -2.595   1.560  -1.080  1.00  0.00           O  
HETATM   24  C14 UNL     1       3.263   1.007  -0.014  1.00  0.00           C  
HETATM   25  C15 UNL     1       4.539   1.588  -0.138  1.00  0.00           C  
HETATM   26  C16 UNL     1       5.494   0.994  -0.936  1.00  0.00           C  
HETATM   27  O11 UNL     1       6.758   1.570  -1.059  1.00  0.00           O  
HETATM   28  H1  UNL     1       5.386  -2.606  -2.736  1.00  0.00           H  
HETATM   29  H2  UNL     1       7.144  -2.356  -3.224  1.00  0.00           H  
HETATM   30  H3  UNL     1       5.832  -1.714  -4.224  1.00  0.00           H  
HETATM   31  H4  UNL     1       3.759  -1.613  -2.012  1.00  0.00           H  
HETATM   32  H5  UNL     1       1.541  -1.705  -1.167  1.00  0.00           H  
HETATM   33  H6  UNL     1       0.815   0.568   0.691  1.00  0.00           H  
HETATM   34  H7  UNL     1      -2.810  -2.235   0.252  1.00  0.00           H  
HETATM   35  H8  UNL     1      -1.781  -2.189   3.861  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.958  -0.264  -0.615  1.00  0.00           H  
HETATM   37  H10 UNL     1      -5.956  -1.012   0.008  1.00  0.00           H  
HETATM   38  H11 UNL     1      -4.722   0.333   2.251  1.00  0.00           H  
HETATM   39  H12 UNL     1      -6.182   1.576   1.394  1.00  0.00           H  
HETATM   40  H13 UNL     1      -2.382   1.400   1.688  1.00  0.00           H  
HETATM   41  H14 UNL     1      -3.934   2.470   3.037  1.00  0.00           H  
HETATM   42  H15 UNL     1      -2.998   1.545  -2.014  1.00  0.00           H  
HETATM   43  H16 UNL     1       2.539   1.511   0.628  1.00  0.00           H  
HETATM   44  H17 UNL     1       4.751   2.513   0.409  1.00  0.00           H  
HETATM   45  H18 UNL     1       6.989   2.418  -0.573  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3
CONECT    3    4    4   26
CONECT    4    5   31
CONECT    5    6   24   24
CONECT    6    7    7   32
CONECT    7    8   33
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   15   34
CONECT   12   13   13   14
CONECT   14   35
CONECT   15   16   17   36
CONECT   16   37
CONECT   17   18   19   38
CONECT   18   39
CONECT   19   20   21   40
CONECT   20   41
CONECT   21   22   22   23
CONECT   23   42
CONECT   24   25   43
CONECT   25   26   26   44
CONECT   26   27
CONECT   27   45
END

HMDB0302546
     RDKit          3D
2-trans-O-Feruloylglucaric acid
 45 45  0  0  0  0  0  0  0  0999 V2000
    6.1162   -1.8945   -3.1680 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2408   -0.7287   -2.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2502   -0.1707   -1.6338 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9972   -0.7181   -1.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9968   -0.1509   -0.6977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -0.7725   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877   -0.3378    0.1211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5973   -1.0714    0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7410   -2.1266   -0.5217 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6732   -0.6335    0.8872 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8957   -1.3327    0.9087 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1533   -1.7990    2.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1866   -2.4523    2.5751 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2372   -1.5079    3.2809 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -0.5333    0.4328 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1994   -1.3966    0.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067    0.6669    1.2432 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5767    1.2318    0.6755 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3583    1.7344    1.2909 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8804    2.7762    2.1054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1172    2.3223   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729    3.5358   -0.3175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5949    1.5600   -1.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2635    1.0067   -0.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5387    1.5878   -0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4938    0.9936   -0.9361 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7584    1.5699   -1.0591 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3859   -2.6056   -2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1444   -2.3561   -3.2236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8315   -1.7141   -4.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7594   -1.6134   -2.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5413   -1.7046   -1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8152    0.5681    0.6911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100   -2.2350    0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -2.1892    3.8614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9575   -0.2639   -0.6150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9560   -1.0117    0.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7225    0.3331    2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1821    1.5758    1.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3821    1.3998    1.6876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9341    2.4699    3.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9984    1.5452   -2.0142 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393    1.5113    0.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7507    2.5131    0.4087 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9887    2.4185   -0.5727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
  5 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 26  3  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
  7 33  1  0
 11 34  1  6
 14 35  1  0
 15 36  1  6
 16 37  1  0
 17 38  1  1
 18 39  1  0
 19 40  1  1
 20 41  1  0
 23 42  1  0
 24 43  1  0
 25 44  1  0
 27 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3S,4S,5R)-2,3,4-Trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}hexanedioate	Generator
2-trans-O-Feruloylglucarate	Generator

Chemical Formula

C₁₆H₁₈O₁₁

Average Molecular Weight

386.3075

Monoisotopic Molecular Weight

386.084911418

IUPAC Name

(2S,3S,4S,5R)-2,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}hexanedioic acid

Traditional Name

(2S,3S,4S,5R)-2,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}hexanedioic acid

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(\C=C\C(=O)O[C@H]([C@@H](O)[C@H](O)[C@H](O)C(O)=O)C(O)=O)=C1

InChI Identifier

InChI=1S/C16H18O11/c1-26-9-6-7(2-4-8(9)17)3-5-10(18)27-14(16(24)25)12(20)11(19)13(21)15(22)23/h2-6,11-14,17,19-21H,1H3,(H,22,23)(H,24,25)/b5-3+/t11-,12-,13-,14+/m0/s1

InChI Key

JZRAOXRUPYISEN-GLJYKRHASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents

Substituents

Glucuronic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Tricarboxylic acid or derivatives
Phenoxy compound
Phenol ether
Methoxybenzene
Styrene
Anisole
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Fatty acid ester
Alkyl aryl ether
Monosaccharide
Alpha-hydroxy acid
Hydroxy acid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Polyol
Ether
Carbonyl group
Organic oxide
Alcohol
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302546)

Food

Fruit

Citrus

Sweet orange (FooDB: FOOD00057)

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	0.71	ALOGPS
logP	-0.52	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.79	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	191.05 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	86.15 m³·mol⁻¹	ChemAxon
Polarizability	35.61 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	186.435	32859911
AllCCS	[M+H-H2O]+	183.942	32859911
AllCCS	[M+Na]+	189.384	32859911
AllCCS	[M+NH4]+	188.728	32859911
AllCCS	[M-H]-	183.052	32859911
AllCCS	[M+Na-2H]-	183.387	32859911
AllCCS	[M+HCOO]-	183.891	32859911
DeepCCS	[M+H]+	185.335	30932474
DeepCCS	[M-H]-	182.939	30932474
DeepCCS	[M-2H]-	215.822	30932474
DeepCCS	[M+Na]+	191.247	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 - 2-trans-O-Feruloylglucaric acid 10V, Positive-QTOF	splash10-00p0-1928000000-753b41cdf7f939bf995d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 20V, Positive-QTOF	splash10-056r-4931000000-61686ad42e4674009058	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 40V, Positive-QTOF	splash10-056r-7910000000-f10ff0fed8e80932624d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 10V, Negative-QTOF	splash10-0fb9-7965000000-74a8a3f6fbaf63d9096c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 20V, Negative-QTOF	splash10-0a73-7931000000-93322e06147e55919f55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 40V, Negative-QTOF	splash10-004i-3920000000-4494c3eeac8ae803f844	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 10V, Positive-QTOF	splash10-00vr-2988000000-3e348681135def6e94b8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 20V, Positive-QTOF	splash10-000b-6940000000-67141ba51c3ec55b5d86	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 40V, Positive-QTOF	splash10-03ds-5910000000-6e34bf6dc33335ea0af1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 10V, Negative-QTOF	splash10-01tl-3495000000-116b3f7bd9738d1eafc4	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 20V, Negative-QTOF	splash10-0a4s-6981000000-648d2f60e6f24d6e0c2d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-trans-O-Feruloylglucaric acid 40V, Negative-QTOF	splash10-0a5a-5901000000-4ec32db7d765e94248b4	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

FDB005075

KNApSAcK ID

Not Available

Chemspider ID

59696348

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for 2-trans-O-Feruloylglucaric acid (HMDB0302546)

MOL for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

3D MOL for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

3D SDF for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

3D-SDF for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

PDB for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

3D PDB for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

SMILES for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

INCHI for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

Structure for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

3D Structure for HMDB0302546 (2-trans-O-Feruloylglucaric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra