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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:08:02 UTC

Update Date

2022-03-07 02:56:38 UTC

HMDB ID

HMDB0040571

Secondary Accession Numbers

HMDB40571

Metabolite Identification

Common Name

2-O-Feruloylhydroxycitric acid

Description

2-O-Feruloylhydroxycitric acid belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. 2-O-Feruloylhydroxycitric acid has been detected, but not quantified in, several different foods, such as breakfast cereal, cereals and cereal products, corns (Zea mays), and fats and oils. This could make 2-O-feruloylhydroxycitric acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 2-O-Feruloylhydroxycitric acid.

Structure

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


  Mrv0541 05061311572D          

 27 27  0  0  0  0            999 V2000
   -0.6487   -1.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529   -0.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8831    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394   -1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    1.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727   -0.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    0.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2425   -1.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6591   -0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    5.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    2.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9403    3.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600    4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    6.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1330    5.8896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101    2.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237    3.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538    4.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    2.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798    3.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    4.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623   -1.0688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    2.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  8  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 14 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  2  0  0  0  0
 19 11  1  0  0  0  0
 20 12  2  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26  1  1  0  0  0  0
 26 10  1  0  0  0  0
 27 12  1  0  0  0  0
 27 13  1  0  0  0  0
M  END

HMDB0040571
     RDKit          3D
2-O-Feruloylhydroxycitric acid
 43 43  0  0  0  0  0  0  0  0999 V2000
    5.8415   -0.4975    1.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315    0.8429    1.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839    1.5467    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5593    0.8886    0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980    1.5291    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1162    0.8830    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9357   -0.3427    0.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014   -0.9342    0.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5926   -2.1129    1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336   -0.2320    0.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8318   -0.7196    0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7269   -0.0377    1.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3036    0.8838    2.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -0.3654    1.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4713   -0.7459   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4627    0.6164   -1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7818   -1.5510   -1.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6189   -2.9673   -1.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885   -3.5674   -0.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881   -3.7722   -2.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9029   -1.1140   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2195   -2.2721   -0.3992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9406   -0.2526   -1.0990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5184    2.8572    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154    3.5122   -0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615    2.8419    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    3.4490    0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8153   -0.9103    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -1.1044    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1109   -0.5242    2.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5591   -0.1524    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337    1.4626    0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582   -0.9522    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745   -1.7699    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3507   -1.0336    2.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7083    0.5685   -2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038   -1.1449   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4219   -1.4788   -2.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747   -3.3965   -3.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8259   -0.2377   -0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    3.3619   -0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7948    4.5490   -0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2210    4.3967    0.0221 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
 18 19  2  0
 18 20  1  0
 15 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  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 20 39  1  0
 23 40  1  0
 24 41  1  0
 25 42  1  0
 27 43  1  0
M  END


  Mrv0541 05061311572D          

 27 27  0  0  0  0            999 V2000
   -0.6487   -1.8657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2529   -0.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8831    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0394   -1.2251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2997    1.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727   -0.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6696    0.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2425   -1.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6591   -0.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    5.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    2.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9403    3.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5600    4.2959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0290   -2.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5133    6.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1330    5.8896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3101    2.5458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237    3.3427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1538    4.7229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1902    2.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1798    3.9260    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9767    4.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8623   -1.0688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9299    2.9156    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  8  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 14 13  1  0  0  0  0
 16  7  1  0  0  0  0
 16 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  2  0  0  0  0
 19 11  1  0  0  0  0
 20 12  2  0  0  0  0
 21 14  2  0  0  0  0
 22 14  1  0  0  0  0
 23 15  2  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26  1  1  0  0  0  0
 26 10  1  0  0  0  0
 27 12  1  0  0  0  0
 27 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040571

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)(CC(O)=O)C(O)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O11/c1-26-10-6-8(2-4-9(10)17)3-5-12(20)27-13(14(21)22)16(25,15(23)24)7-11(18)19/h2-6,13,17,25H,7H2,1H3,(H,18,19)(H,21,22)(H,23,24)/b5-3+

> <INCHI_KEY>
QAEWENIBBUMYIB-HWKANZROSA-N

> <FORMULA>
C16H16O11

> <MOLECULAR_WEIGHT>
384.2916

> <EXACT_MASS>
384.069261354

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
34.65433523443106

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
0.5348082180000003

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.303190612133933

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.86266134569989

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5894545120764745

> <JCHEM_POLAR_SURFACE_AREA>
187.88999999999996

> <JCHEM_REFRACTIVITY>
84.9739

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-1-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0040571
     RDKit          3D
2-O-Feruloylhydroxycitric acid
 43 43  0  0  0  0  0  0  0  0999 V2000
    5.8415   -0.4975    1.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315    0.8429    1.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839    1.5467    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5593    0.8886    0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980    1.5291    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1162    0.8830    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9357   -0.3427    0.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014   -0.9342    0.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5926   -2.1129    1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336   -0.2320    0.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8318   -0.7196    0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7269   -0.0377    1.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3036    0.8838    2.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -0.3654    1.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4713   -0.7459   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4627    0.6164   -1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7818   -1.5510   -1.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6189   -2.9673   -1.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885   -3.5674   -0.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881   -3.7722   -2.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9029   -1.1140   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2195   -2.2721   -0.3992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9406   -0.2526   -1.0990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5184    2.8572    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154    3.5122   -0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615    2.8419    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    3.4490    0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8153   -0.9103    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -1.1044    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1109   -0.5242    2.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5591   -0.1524    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337    1.4626    0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582   -0.9522    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745   -1.7699    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3507   -1.0336    2.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7083    0.5685   -2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038   -1.1449   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4219   -1.4788   -2.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747   -3.3965   -3.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8259   -0.2377   -0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    3.3619   -0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7948    4.5490   -0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2210    4.3967    0.0221 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
 18 19  2  0
 18 20  1  0
 15 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  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 20 39  1  0
 23 40  1  0
 24 41  1  0
 25 42  1  0
 27 43  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.211  -3.483   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.072  -0.799   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.382   1.777   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.674  -2.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.293   2.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.496  -0.109   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001   9.108   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.983   0.290   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.186  -2.686   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.097  -1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.602  10.595   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.691   4.353   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.489   7.329   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.823   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.912   8.019   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.787  -4.173   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -4.691  11.684   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.115  10.994   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -6.179   4.752   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.578   6.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -5.887   8.816   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.222   5.442   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.336   7.329   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -1.823   9.108   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.610  -1.995   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.602   5.442   0.000  0.00  0.00           O+0
CONECT    1   26                                                            
CONECT    2    4    8                                                       
CONECT    3    5    8                                                       
CONECT    4    2    9                                                       
CONECT    5    3   12                                                       
CONECT    6    8   10                                                       
CONECT    7   11   16                                                       
CONECT    8    2    3    6                                                  
CONECT    9    4   10   17                                                  
CONECT   10    6    9   26                                                  
CONECT   11    7   18   19                                                  
CONECT   12    5   20   27                                                  
CONECT   13   14   16   27                                                  
CONECT   14   13   21   22                                                  
CONECT   15   16   23   24                                                  
CONECT   16    7   13   15   25                                             
CONECT   17    9                                                            
CONECT   18   11                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   14                                                            
CONECT   22   14                                                            
CONECT   23   15                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26    1   10                                                       
CONECT   27   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

COMPND    HMDB0040571
HETATM    1  C1  UNL     1       5.842  -0.498   1.595  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.932   0.843   1.163  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.784   1.547   0.782  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.559   0.889   0.842  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.398   1.529   0.481  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.116   0.883   0.530  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.936  -0.343   0.912  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.401  -0.934   0.936  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.593  -2.113   1.301  1.00  0.00           O  
HETATM   10  O3  UNL     1      -1.534  -0.232   0.558  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.832  -0.720   0.553  1.00  0.00           C  
HETATM   12  C9  UNL     1      -3.727  -0.038   1.534  1.00  0.00           C  
HETATM   13  O4  UNL     1      -3.304   0.884   2.273  1.00  0.00           O  
HETATM   14  O5  UNL     1      -5.064  -0.365   1.696  1.00  0.00           O  
HETATM   15  C10 UNL     1      -3.471  -0.746  -0.811  1.00  0.00           C  
HETATM   16  O6  UNL     1      -3.463   0.616  -1.232  1.00  0.00           O  
HETATM   17  C11 UNL     1      -2.782  -1.551  -1.838  1.00  0.00           C  
HETATM   18  C12 UNL     1      -2.619  -2.967  -1.552  1.00  0.00           C  
HETATM   19  O7  UNL     1      -2.988  -3.567  -0.516  1.00  0.00           O  
HETATM   20  O8  UNL     1      -1.988  -3.772  -2.512  1.00  0.00           O  
HETATM   21  C13 UNL     1      -4.903  -1.114  -0.763  1.00  0.00           C  
HETATM   22  O9  UNL     1      -5.219  -2.272  -0.399  1.00  0.00           O  
HETATM   23  O10 UNL     1      -5.941  -0.253  -1.099  1.00  0.00           O  
HETATM   24  C14 UNL     1       2.518   2.857   0.056  1.00  0.00           C  
HETATM   25  C15 UNL     1       3.715   3.512  -0.007  1.00  0.00           C  
HETATM   26  C16 UNL     1       4.862   2.842   0.363  1.00  0.00           C  
HETATM   27  O11 UNL     1       6.125   3.449   0.324  1.00  0.00           O  
HETATM   28  H1  UNL     1       6.815  -0.910   1.903  1.00  0.00           H  
HETATM   29  H2  UNL     1       5.413  -1.104   0.787  1.00  0.00           H  
HETATM   30  H3  UNL     1       5.111  -0.524   2.457  1.00  0.00           H  
HETATM   31  H4  UNL     1       3.559  -0.152   1.187  1.00  0.00           H  
HETATM   32  H5  UNL     1       0.234   1.463   0.225  1.00  0.00           H  
HETATM   33  H6  UNL     1       1.758  -0.952   1.219  1.00  0.00           H  
HETATM   34  H7  UNL     1      -2.775  -1.770   0.907  1.00  0.00           H  
HETATM   35  H8  UNL     1      -5.351  -1.034   2.412  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.708   0.568  -2.205  1.00  0.00           H  
HETATM   37  H10 UNL     1      -1.804  -1.145  -2.169  1.00  0.00           H  
HETATM   38  H11 UNL     1      -3.422  -1.479  -2.771  1.00  0.00           H  
HETATM   39  H12 UNL     1      -1.575  -3.397  -3.353  1.00  0.00           H  
HETATM   40  H13 UNL     1      -6.826  -0.238  -0.578  1.00  0.00           H  
HETATM   41  H14 UNL     1       1.596   3.362  -0.230  1.00  0.00           H  
HETATM   42  H15 UNL     1       3.795   4.549  -0.341  1.00  0.00           H  
HETATM   43  H16 UNL     1       6.221   4.397   0.022  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   21
CONECT   16   36
CONECT   17   18   37   38
CONECT   18   19   19   20
CONECT   20   39
CONECT   21   22   22   23
CONECT   23   40
CONECT   24   25   41
CONECT   25   26   26   42
CONECT   26   27
CONECT   27   43
END

HMDB0040571
     RDKit          3D
2-O-Feruloylhydroxycitric acid
 43 43  0  0  0  0  0  0  0  0999 V2000
    5.8415   -0.4975    1.5955 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9315    0.8429    1.1628 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7839    1.5467    0.7818 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5593    0.8886    0.8423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980    1.5291    0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1162    0.8830    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9357   -0.3427    0.9118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4014   -0.9342    0.9357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5926   -2.1129    1.3008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5336   -0.2320    0.5581 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8318   -0.7196    0.5526 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7269   -0.0377    1.5336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3036    0.8838    2.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -0.3654    1.6963 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4713   -0.7459   -0.8113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4627    0.6164   -1.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7818   -1.5510   -1.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6189   -2.9673   -1.5520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885   -3.5674   -0.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9881   -3.7722   -2.5116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9029   -1.1140   -0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2195   -2.2721   -0.3992 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9406   -0.2526   -1.0990 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5184    2.8572    0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7154    3.5122   -0.0072 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8615    2.8419    0.3625 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1246    3.4490    0.3238 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8153   -0.9103    1.9030 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4128   -1.1044    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1109   -0.5242    2.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5591   -0.1524    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337    1.4626    0.2245 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7582   -0.9522    1.2191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7745   -1.7699    0.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3507   -1.0336    2.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7083    0.5685   -2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8038   -1.1449   -2.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4219   -1.4788   -2.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5747   -3.3965   -3.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8259   -0.2377   -0.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5958    3.3619   -0.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7948    4.5490   -0.3407 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2210    4.3967    0.0221 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
 18 19  2  0
 18 20  1  0
 15 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  0
 14 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 20 39  1  0
 23 40  1  0
 24 41  1  0
 25 42  1  0
 27 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-O-Feruloylhydroxycitrate	Generator
2-Hydroxy-1-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylate	HMDB

Chemical Formula

C₁₆H₁₆O₁₁

Average Molecular Weight

384.2916

Monoisotopic Molecular Weight

384.069261354

IUPAC Name

2-hydroxy-1-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

Traditional Name

2-hydroxy-1-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}propane-1,2,3-tricarboxylic acid

CAS Registry Number

62345-86-2

SMILES

COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)(CC(O)=O)C(O)=O)=C1

InChI Identifier

InChI=1S/C16H16O11/c1-26-10-6-8(2-4-9(10)17)3-5-12(20)27-13(14(21)22)16(25,15(23)24)7-11(18)19/h2-6,13,17,25H,7H2,1H3,(H,18,19)(H,21,22)(H,23,24)/b5-3+

InChI Key

QAEWENIBBUMYIB-HWKANZROSA-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
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Styrene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Fatty acid ester
Phenol
Alpha-hydroxy acid
Fatty acyl
Benzenoid
Hydroxy acid
Monocyclic benzene moiety
Monosaccharide
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Carboxylic acid ester
Ether
Carboxylic acid
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040571)
Cytoplasm (HMDB: HMDB0040571)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040571)

Source

Exogenous

Food

Food (HMDB: HMDB0040571)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Corn (FooDB: FOOD00205)

Cereals and cereal products (FooDB: FOOD00858)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Poaceae (HMDB: HMDB0040571)

Not Available

Nutrient (HMDB: HMDB0040571)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	154 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	11010 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.75 g/L	ALOGPS
logP	0.97	ALOGPS
logP	0.53	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	2.86	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	187.89 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	84.97 m³·mol⁻¹	ChemAxon
Polarizability	34.65 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]+	185.782	30932474
DeepCCS	[M-H]-	183.424	30932474
DeepCCS	[M-2H]-	216.762	30932474
DeepCCS	[M+Na]+	191.991	30932474
AllCCS	[M+H]+	184.0	32859911
AllCCS	[M+H-H2O]+	181.4	32859911
AllCCS	[M+NH4]+	186.3	32859911
AllCCS	[M+Na]+	187.0	32859911
AllCCS	[M-H]-	182.1	32859911
AllCCS	[M+Na-2H]-	182.4	32859911
AllCCS	[M+HCOO]-	182.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-O-Feruloylhydroxycitric acid	COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)(CC(O)=O)C(O)=O)=C1	5679.8	Standard polar	33892256
2-O-Feruloylhydroxycitric acid	COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)(CC(O)=O)C(O)=O)=C1	2816.4	Standard non polar	33892256
2-O-Feruloylhydroxycitric acid	COC1=C(O)C=CC(\C=C\C(=O)OC(C(O)=O)C(O)(CC(O)=O)C(O)=O)=C1	3266.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-O-Feruloylhydroxycitric acid,1TMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O)C(=O)O)=CC=C1O[Si](C)(C)C	3298.1	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,1TMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O)=CC=C1O	3248.7	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,1TMS,isomer #3	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O)=CC=C1O	3307.0	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,1TMS,isomer #4	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O)=CC=C1O	3251.2	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,1TMS,isomer #5	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C)=CC=C1O	3208.5	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O)=CC=C1O[Si](C)(C)C	3183.3	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #10	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	3113.5	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	3275.7	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #3	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	3184.6	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #4	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3178.2	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #5	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O)=CC=C1O	3188.3	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #6	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O)=CC=C1O	3124.1	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #7	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C)=CC=C1O	3107.3	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #8	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O)=CC=C1O	3175.1	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TMS,isomer #9	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	3170.0	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	3180.6	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #10	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	3115.4	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	3117.6	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #3	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3109.9	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #4	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	3171.3	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #5	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3173.3	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #6	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3120.2	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #7	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O)=CC=C1O	3110.2	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #8	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	3116.0	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TMS,isomer #9	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	3092.0	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C	3148.1	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(CC(=O)O)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3133.5	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TMS,isomer #3	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(O)(CC(=O)O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3123.2	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TMS,isomer #4	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3135.1	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TMS,isomer #5	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O	3099.7	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,5TMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C)C(CC(=O)O[Si](C)(C)C)(O[Si](C)(C)C)C(=O)O[Si](C)(C)C)=CC=C1O[Si](C)(C)C	3146.1	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,1TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3565.6	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,1TBDMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O)C(=O)O)=CC=C1O	3527.7	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,1TBDMS,isomer #3	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	3559.9	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,1TBDMS,isomer #4	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	3544.0	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,1TBDMS,isomer #5	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3534.1	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3710.5	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #10	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3672.4	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3741.8	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #3	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3723.5	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #4	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3717.0	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #5	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	3686.0	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #6	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	3672.2	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #7	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3662.3	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #8	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	3693.2	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,2TBDMS,isomer #9	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3683.9	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3875.3	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #10	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3840.5	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3861.0	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #3	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3850.1	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #4	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	3891.8	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #5	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3877.5	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #6	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	3874.4	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #7	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O	3835.4	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #8	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3825.3	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,3TBDMS,isomer #9	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3807.9	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TBDMS,isomer #1	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O)=CC=C1O[Si](C)(C)C(C)(C)C	4031.6	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TBDMS,isomer #2	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4008.0	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TBDMS,isomer #3	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(O)(CC(=O)O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4016.5	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TBDMS,isomer #4	COC1=CC(/C=C/C(=O)OC(C(=O)O)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	4029.4	Semi standard non polar	33892256
2-O-Feruloylhydroxycitric acid,4TBDMS,isomer #5	COC1=CC(/C=C/C(=O)OC(C(=O)O[Si](C)(C)C(C)(C)C)C(CC(=O)O[Si](C)(C)C(C)(C)C)(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C)=CC=C1O	3974.3	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 - 2-O-Feruloylhydroxycitric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-5903000000-44984e0ea4c5bea5031d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-Feruloylhydroxycitric acid GC-MS (4 TMS) - 70eV, Positive	splash10-0adi-9180037000-b64c656c3acb8d6601c7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-Feruloylhydroxycitric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-O-Feruloylhydroxycitric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	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 - 2-O-Feruloylhydroxycitric acid 10V, Positive-QTOF	splash10-0170-0409000000-34018e0cc96fa870df50	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 20V, Positive-QTOF	splash10-0a4i-7925000000-c3f6f9253b4bcaa39f39	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 40V, Positive-QTOF	splash10-052n-2900000000-04e7bfe8a1c38c296d10	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 10V, Negative-QTOF	splash10-001r-2938000000-e52f39c9f3f4d22bdb6d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 20V, Negative-QTOF	splash10-05a9-7976000000-86c68bc162b4280e9f95	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 40V, Negative-QTOF	splash10-052r-9770000000-db7b26b925840eec7753	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 10V, Negative-QTOF	splash10-006x-1098000000-54ac7eced5eb0df3eeb9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 20V, Negative-QTOF	splash10-03dj-0901000000-afc66e98a37afbc690b8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 40V, Negative-QTOF	splash10-000i-9401000000-fcd5cc69f5c30e25f59b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 10V, Positive-QTOF	splash10-00rj-0109000000-1784f880a6bba61be9f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 20V, Positive-QTOF	splash10-0005-6930000000-4c621c1a3b05180dcd85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-O-Feruloylhydroxycitric acid 40V, Positive-QTOF	splash10-0006-9100000000-0cb63aa4cccf8f0a1353	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020349

KNApSAcK ID

Not Available

Chemspider ID

35014964

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752859

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1884501

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-O-Feruloylhydroxycitric acid (HMDB0040571)

MOL for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

3D MOL for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

3D SDF for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

3D-SDF for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

PDB for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

3D PDB for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

SMILES for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

INCHI for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

Structure for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

3D Structure for HMDB0040571 (2-O-Feruloylhydroxycitric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra