MiMeDB: Showing metabocard for Coutaric acid (MMDBc0033611)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:55:48 UTC

Update Date

2022-08-31 22:37:01 UTC

Metabolite ID

MMDBc0033611

Metabolite Identification

Common Name

Coutaric acid

Description

Coutaric acid is a the ester of tartaric acid and the phenolic acid coumaric acid, a type of polyphenol. Polyphenol are secondary plant metabolites and components of grapes, wines and beers. They contribute to the sensory characteristics of wine. Yeast can influence the polyphenolic wine composition by adsorbing them throught its cell wall during wine making. [Caridi 2004]

Structure

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

HMDB0029225
     RDKit          3D
Coutaric acid
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.0431   -2.1976    1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -1.8605    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050   -0.3661    0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1268   -0.1822   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607   -1.0317   -1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -0.0910    0.7692 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3955    1.1795    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    2.3594    0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    3.5956    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3252    4.8207    0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377    5.9216    0.2790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7058    4.7968    0.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8404    3.6414    0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    2.4847    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    1.2385    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7797    0.0823    0.5519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9847   -0.6801    1.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828   -0.2517    2.9394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -2.0432    1.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1840   -1.7666    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5240   -0.5686   -0.5074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5487   -0.9945   -1.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1915   -1.6608   -2.6798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291    0.3010   -1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541   -0.4610   -2.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -3.0925    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6001   -1.3763    1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5057   -2.4897    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317   -2.0747    2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014   -2.4749    0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.1818    1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2830    0.8625   -0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695   -0.5820   -0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393   -2.0985   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735   -0.8869   -1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0801   -0.6905   -2.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423   -0.9140    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2037    2.3467    0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    4.3355    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2911    4.6270    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439    2.5772    0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045   -2.7238    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298   -2.4453    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2609   -1.5358    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274   -2.6498   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463   -0.1160   -1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344   -1.7031   -1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2881   -2.6873   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5213   -1.6424   -3.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120    0.4756   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2585    1.2059   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1734   -0.6945   -1.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21 24  1  0
 24 25  1  0
 15  7  1  0
 21 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  8 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
M  END


  Mrv1652304062013032D          

 25 26  0  0  1  0            999 V2000
    1.6261   -3.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0130   -3.0096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1845   -2.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9691   -1.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1406   -1.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714   -1.6506    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429   -0.8436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298   -0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    0.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860    0.7703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    0.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275   -0.5887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837    0.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0968   -0.0788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6552    1.2802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548   -0.5465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248   -1.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222   -0.0616    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7272    0.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522    0.6658    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9172    0.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0923    0.6658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  8 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  1  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033611

> <DATABASE_NAME>
MIME

> <SMILES>
CCC(CC)NC1=C(C=CC(=C1)C(O)=O)N1C(=O)CC[C@@]1(CN)CO

> <INCHI_IDENTIFIER>
InChI=1S/C18H27N3O4/c1-3-13(4-2)20-14-9-12(17(24)25)5-6-15(14)21-16(23)7-8-18(21,10-19)11-22/h5-6,9,13,20,22H,3-4,7-8,10-11,19H2,1-2H3,(H,24,25)/t18-/m1/s1

> <INCHI_KEY>
ZEZFFRWWHKSMEB-GOSISDBHSA-N

> <FORMULA>
C18H27N3O4

> <MOLECULAR_WEIGHT>
349.4247

> <EXACT_MASS>
349.200156367

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.06676867371703

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2R)-2-(aminomethyl)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-3-[(pentan-3-yl)amino]benzoic acid

> <ALOGPS_LOGP>
0.05

> <JCHEM_LOGP>
-1.5161384023972506

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.701095498728336

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.939634144592443

> <JCHEM_PKA_STRONGEST_BASIC>
8.682735991017744

> <JCHEM_POLAR_SURFACE_AREA>
115.89

> <JCHEM_REFRACTIVITY>
96.39949999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2R)-2-(aminomethyl)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-3-(pentan-3-ylamino)benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029225
     RDKit          3D
Coutaric acid
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.0431   -2.1976    1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -1.8605    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050   -0.3661    0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1268   -0.1822   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607   -1.0317   -1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -0.0910    0.7692 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3955    1.1795    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    2.3594    0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    3.5956    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3252    4.8207    0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377    5.9216    0.2790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7058    4.7968    0.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8404    3.6414    0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    2.4847    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    1.2385    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7797    0.0823    0.5519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9847   -0.6801    1.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828   -0.2517    2.9394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -2.0432    1.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1840   -1.7666    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5240   -0.5686   -0.5074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5487   -0.9945   -1.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1915   -1.6608   -2.6798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291    0.3010   -1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541   -0.4610   -2.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -3.0925    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6001   -1.3763    1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5057   -2.4897    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317   -2.0747    2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014   -2.4749    0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.1818    1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2830    0.8625   -0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695   -0.5820   -0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393   -2.0985   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735   -0.8869   -1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0801   -0.6905   -2.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423   -0.9140    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2037    2.3467    0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    4.3355    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2911    4.6270    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439    2.5772    0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045   -2.7238    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298   -2.4453    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2609   -1.5358    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274   -2.6498   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463   -0.1160   -1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344   -1.7031   -1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2881   -2.6873   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5213   -1.6424   -3.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120    0.4756   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2585    1.2059   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1734   -0.6945   -1.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21 24  1  0
 24 25  1  0
 15  7  1  0
 21 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  8 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  C   UNK     0       3.035  -6.648   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.891  -5.618   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.211  -4.112   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.676  -3.636   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.996  -2.129   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.067  -3.081   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       1.387  -1.575   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.242  -0.544   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.563   0.962   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.027   1.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.172   0.407   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.851  -1.099   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.636   0.883   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.781  -0.147   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.956   2.390   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      -1.222  -1.020   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -1.698  -2.485   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.793  -3.731   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.238  -2.485   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.714  -1.020   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.468  -0.115   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.224   1.227   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -4.764   1.243   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -1.712   1.227   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.172   1.243   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11    7                                                       
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    8   17   21                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16   22   24                                             
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

COMPND    HMDB0029225
HETATM    1  C1  UNL     1       4.043  -2.198   1.269  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.579  -1.861   1.153  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.405  -0.366   0.825  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.127  -0.182  -0.495  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.561  -1.032  -1.606  1.00  0.00           C  
HETATM    6  N1  UNL     1       1.003  -0.091   0.769  1.00  0.00           N  
HETATM    7  C6  UNL     1       0.395   1.179   0.617  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.138   2.359   0.580  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.531   3.596   0.441  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.325   4.821   0.405  1.00  0.00           C  
HETATM   11  O1  UNL     1       0.738   5.922   0.279  1.00  0.00           O  
HETATM   12  O2  UNL     1       2.706   4.797   0.507  1.00  0.00           O  
HETATM   13  C10 UNL     1      -0.840   3.641   0.340  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.586   2.485   0.375  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.979   1.238   0.514  1.00  0.00           C  
HETATM   16  N2  UNL     1      -1.780   0.082   0.552  1.00  0.00           N  
HETATM   17  C13 UNL     1      -1.985  -0.680   1.764  1.00  0.00           C  
HETATM   18  O3  UNL     1      -1.783  -0.252   2.939  1.00  0.00           O  
HETATM   19  C14 UNL     1      -2.468  -2.043   1.419  1.00  0.00           C  
HETATM   20  C15 UNL     1      -3.184  -1.767   0.123  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.524  -0.569  -0.507  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.549  -0.995  -1.569  1.00  0.00           C  
HETATM   23  N3  UNL     1      -2.191  -1.661  -2.680  1.00  0.00           N  
HETATM   24  C18 UNL     1      -3.629   0.301  -1.071  1.00  0.00           C  
HETATM   25  O4  UNL     1      -4.254  -0.461  -2.080  1.00  0.00           O  
HETATM   26  H1  UNL     1       4.097  -3.093   1.941  1.00  0.00           H  
HETATM   27  H2  UNL     1       4.600  -1.376   1.790  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.506  -2.490   0.305  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.032  -2.075   2.097  1.00  0.00           H  
HETATM   30  H5  UNL     1       2.101  -2.475   0.364  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.968   0.182   1.581  1.00  0.00           H  
HETATM   32  H7  UNL     1       3.283   0.862  -0.786  1.00  0.00           H  
HETATM   33  H8  UNL     1       4.169  -0.582  -0.312  1.00  0.00           H  
HETATM   34  H9  UNL     1       2.839  -2.099  -1.499  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.474  -0.887  -1.765  1.00  0.00           H  
HETATM   36  H11 UNL     1       3.080  -0.690  -2.543  1.00  0.00           H  
HETATM   37  H12 UNL     1       0.342  -0.914   0.850  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.204   2.347   0.666  1.00  0.00           H  
HETATM   39  H14 UNL     1       3.096   4.336   1.345  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.291   4.627   0.232  1.00  0.00           H  
HETATM   41  H16 UNL     1      -2.644   2.577   0.293  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.604  -2.724   1.210  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.130  -2.445   2.211  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.261  -1.536   0.375  1.00  0.00           H  
HETATM   45  H20 UNL     1      -3.227  -2.650  -0.555  1.00  0.00           H  
HETATM   46  H21 UNL     1      -0.946  -0.116  -1.903  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.834  -1.703  -1.106  1.00  0.00           H  
HETATM   48  H23 UNL     1      -2.288  -2.687  -2.415  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.521  -1.642  -3.480  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.412   0.476  -0.307  1.00  0.00           H  
HETATM   51  H26 UNL     1      -3.258   1.206  -1.573  1.00  0.00           H  
HETATM   52  H27 UNL     1      -5.173  -0.695  -1.880  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    6   31
CONECT    4    5   32   33
CONECT    5   34   35   36
CONECT    6    7   37
CONECT    7    8    8   15
CONECT    8    9   38
CONECT    9   10   13   13
CONECT   10   11   11   12
CONECT   12   39
CONECT   13   14   40
CONECT   14   15   15   41
CONECT   15   16
CONECT   16   17   21
CONECT   17   18   18   19
CONECT   19   20   42   43
CONECT   20   21   44   45
CONECT   21   22   24
CONECT   22   23   46   47
CONECT   23   48   49
CONECT   24   25   50   51
CONECT   25   52
END

HMDB0029225
     RDKit          3D
Coutaric acid
 52 53  0  0  0  0  0  0  0  0999 V2000
    4.0431   -2.1976    1.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5794   -1.8605    1.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4050   -0.3661    0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1268   -0.1822   -0.4954 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5607   -1.0317   -1.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0032   -0.0910    0.7692 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3955    1.1795    0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1383    2.3594    0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    3.5956    0.4412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3252    4.8207    0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377    5.9216    0.2790 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7058    4.7968    0.5073 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8404    3.6414    0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864    2.4847    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9790    1.2385    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7797    0.0823    0.5519 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9847   -0.6801    1.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7828   -0.2517    2.9394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4685   -2.0432    1.4188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1840   -1.7666    0.1235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5240   -0.5686   -0.5074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5487   -0.9945   -1.5693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1915   -1.6608   -2.6798 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6291    0.3010   -1.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2541   -0.4610   -2.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0974   -3.0925    1.9414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6001   -1.3763    1.7898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5057   -2.4897    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0317   -2.0747    2.0968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1014   -2.4749    0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.1818    1.5809 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2830    0.8625   -0.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1695   -0.5820   -0.3123 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393   -2.0985   -1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4735   -0.8869   -1.7649 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0801   -0.6905   -2.5429 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3423   -0.9140    0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2037    2.3467    0.6659 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    4.3355    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2911    4.6270    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6439    2.5772    0.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045   -2.7238    1.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1298   -2.4453    2.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2609   -1.5358    0.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2274   -2.6498   -0.5552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9463   -0.1160   -1.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344   -1.7031   -1.1060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2881   -2.6873   -2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5213   -1.6424   -3.4805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4120    0.4756   -0.3067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2585    1.2059   -1.5731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1734   -0.6945   -1.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  6
 22 23  1  0
 21 24  1  0
 24 25  1  0
 15  7  1  0
 21 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  5 34  1  0
  5 35  1  0
  5 36  1  0
  6 37  1  0
  8 38  1  0
 12 39  1  0
 13 40  1  0
 14 41  1  0
 19 42  1  0
 19 43  1  0
 20 44  1  0
 20 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
M  END

Synonyms

Value	Source
Coutarate	Generator
4-[(2R)-2-(Aminomethyl)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-3-[(pentan-3-yl)amino]benzoate	Generator, HMDB

Molecular Formula

C₁₈H₂₇N₃O₄

Average Mass

349.4247

Monoisotopic Mass

349.200156367

IUPAC Name

4-[(2R)-2-(aminomethyl)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-3-[(pentan-3-yl)amino]benzoic acid

Traditional Name

4-[(2R)-2-(aminomethyl)-2-(hydroxymethyl)-5-oxopyrrolidin-1-yl]-3-(pentan-3-ylamino)benzoic acid

CAS Registry Number

Not Available

SMILES

CCC(CC)NC1=C(C=CC(=C1)C(O)=O)N1C(=O)CC[C@@]1(CN)CO

InChI Identifier

InChI=1S/C18H27N3O4/c1-3-13(4-2)20-14-9-12(17(24)25)5-6-15(14)21-16(23)7-8-18(21,10-19)11-22/h5-6,9,13,20,22H,3-4,7-8,10-11,19H2,1-2H3,(H,24,25)/t18-/m1/s1

InChI Key

ZEZFFRWWHKSMEB-GOSISDBHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acid esters

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.33 g/L	ALOGPS
logP	0.05	ALOGPS
logP	-1.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.94	ChemAxon
pKa (Strongest Basic)	8.68	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.89 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	96.4 m³·mol⁻¹	ChemAxon
Polarizability	37.07 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00lr-9088000000-6372e71701b9007ec7c8	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0fir-6102900000-295dcb9e8b2e373a1dac	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-0049000000-f2c616cabf8ba29465a5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052b-0194000000-0ce8911ddc48851774bd	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08mi-2690000000-60760e5819a0a0dc671a	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0019000000-a9163591a823db5b6c99	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fz1-0069000000-bf9f79070c99619d797e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0230-2291000000-a2b767641461d5e2da1c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0009000000-c2779d527ca2008ce75c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0049000000-0999bb90f616209f38d8	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00bc-2972000000-5075f89a3b79a7906772	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0049000000-54683d07706271fc56a1	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0029000000-5de9b533cd87b1c12cb3	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0296-3896000000-bd1ef977bdb1621179bc	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-16	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00053055

Chemspider ID

26325199

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Coutaric acid

METLIN ID

Not Available

PubChem Compound

57517924

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Ramirez-Gaona M, Marcu A, Pon A, Guo AC, Sajed T, Wishart NA, Karu N, Djoumbou Feunang Y, Arndt D, Wishart DS: YMDB 2.0: a significantly expanded version of the yeast metabolome database. Nucleic Acids Res. 2017 Jan 4;45(D1):D440-D445. doi: 10.1093/nar/gkw1058. Epub 2016 Nov 28. [PubMed:27899612 ]

Showing metabocard for Coutaric acid (MMDBc0033611)

MOL for #<Metabolite:0x00007fdb3400f110>

3D MOL for #<Metabolite:0x00007fdb3400f110>

3D SDF for #<Metabolite:0x00007fdb3400f110>

3D-SDF for #<Metabolite:0x00007fdb3400f110>

PDB for #<Metabolite:0x00007fdb3400f110>

3D PDB for #<Metabolite:0x00007fdb3400f110>

SMILES for #<Metabolite:0x00007fdb3400f110>

INCHI for #<Metabolite:0x00007fdb3400f110>

Structure for #<Metabolite:0x00007fdb3400f110>

3D Structure for #<Metabolite:0x00007fdb3400f110>