Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 03:30:12 UTC

Update Date

2021-09-26 22:59:37 UTC

HMDB ID

HMDB0249020

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-

Description

Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-, also known as tranilast hydrate or 2-((3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid, belongs to the class of organic compounds known as n-cinnamoylanthranilic acids. These are aromatic compounds containing a cinnamic acid conjugated to an anthranilic acid. Based on a literature review very few articles have been published on Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-. This compound has been identified in human blood as reported by (PMID: 31557052 ). Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0249020
     RDKit          3D
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-
 41 42  0  0  0  0  0  0  0  0999 V2000
   -6.7441   -1.4299    1.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0083   -0.7650    0.6080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208   -0.6736    0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8644   -1.2243    1.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -1.1164    1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978   -0.4587    0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230   -0.3169    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4525   -0.8077    1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -0.6801    1.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5291   -1.2228    2.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334    0.0048    0.4360 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    0.1834    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557   -0.2404    1.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2285   -0.0515    1.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7310    0.5952    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8564    1.0324   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4651    0.8434   -0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355    1.3417   -1.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4109    1.2973   -2.0023 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2956    1.9994   -2.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669    0.0967   -0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9381   -0.0163   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7231    0.5377   -1.3820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    1.2179   -2.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5960   -2.5249    1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3755   -1.1775    2.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8154   -1.1962    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615   -1.7512    2.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9237   -1.5661    2.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0710    0.2242   -0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.3502    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089    0.3994   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5020   -0.7570    2.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8707   -0.4267    1.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8100    0.7489   -0.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2615    1.5427   -1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8025    2.8495   -2.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    0.6245   -1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7394    2.2423   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2443    0.6047   -2.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8253    1.3673   -3.2458 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  2  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  6 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 17 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 20 37  1  0
 21 38  1  0
 24 39  1  0
 24 40  1  0
 24 41  1  0
M  END

  Mrv1652309112105302D          

 24 25  0  0  0  0            999 V2000
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  9  6  1  4  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  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
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
  4 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249020

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C(C=CC(=O)NC2=CC=CC=C2C(O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)

> <INCHI_KEY>
NZHGWWWHIYHZNX-UHFFFAOYSA-N

> <FORMULA>
C18H17NO5

> <MOLECULAR_WEIGHT>
327.336

> <EXACT_MASS>
327.110672651

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.26124968197476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
3.5626285343333333

> <ALOGPS_LOGS>
-4.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.359298815013268

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5528402162392942

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0491071535256444

> <JCHEM_POLAR_SURFACE_AREA>
84.86

> <JCHEM_REFRACTIVITY>
91.5198

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.40e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tranilast

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0249020
     RDKit          3D
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-
 41 42  0  0  0  0  0  0  0  0999 V2000
   -6.7441   -1.4299    1.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0083   -0.7650    0.6080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208   -0.6736    0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8644   -1.2243    1.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -1.1164    1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978   -0.4587    0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230   -0.3169    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4525   -0.8077    1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -0.6801    1.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5291   -1.2228    2.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334    0.0048    0.4360 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    0.1834    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557   -0.2404    1.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2285   -0.0515    1.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7310    0.5952    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8564    1.0324   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4651    0.8434   -0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355    1.3417   -1.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4109    1.2973   -2.0023 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2956    1.9994   -2.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669    0.0967   -0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9381   -0.0163   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7231    0.5377   -1.3820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    1.2179   -2.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5960   -2.5249    1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3755   -1.1775    2.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8154   -1.1962    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615   -1.7512    2.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9237   -1.5661    2.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0710    0.2242   -0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.3502    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089    0.3994   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5020   -0.7570    2.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8707   -0.4267    1.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8100    0.7489   -0.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2615    1.5427   -1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8025    2.8495   -2.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    0.6245   -1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7394    2.2423   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2443    0.6047   -2.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8253    1.3673   -3.2458 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  2  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  6 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 17 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 20 37  1  0
 21 38  1  0
 24 39  1  0
 24 40  1  0
 24 41  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   13  N   UNK     0      -4.001 -14.630   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.668 -16.170   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -8.002 -16.940   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    4   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0249020
HETATM    1  C1  UNL     1      -6.744  -1.430   1.613  1.00  0.00           C  
HETATM    2  O1  UNL     1      -6.008  -0.765   0.608  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.621  -0.674   0.635  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.864  -1.224   1.644  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.466  -1.116   1.646  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.798  -0.459   0.644  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.323  -0.317   0.599  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.453  -0.808   1.511  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.898  -0.680   1.486  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.529  -1.223   2.464  1.00  0.00           O  
HETATM   11  N1  UNL     1       2.533   0.005   0.436  1.00  0.00           N  
HETATM   12  C9  UNL     1       3.930   0.183   0.324  1.00  0.00           C  
HETATM   13  C10 UNL     1       4.856  -0.240   1.254  1.00  0.00           C  
HETATM   14  C11 UNL     1       6.229  -0.051   1.143  1.00  0.00           C  
HETATM   15  C12 UNL     1       6.731   0.595   0.051  1.00  0.00           C  
HETATM   16  C13 UNL     1       5.856   1.032  -0.894  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.465   0.843  -0.787  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.636   1.342  -1.854  1.00  0.00           C  
HETATM   19  O3  UNL     1       2.411   1.297  -2.002  1.00  0.00           O  
HETATM   20  O4  UNL     1       4.296   1.999  -2.934  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.567   0.097  -0.375  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.938  -0.016  -0.364  1.00  0.00           C  
HETATM   23  O5  UNL     1      -4.723   0.538  -1.382  1.00  0.00           O  
HETATM   24  C18 UNL     1      -4.074   1.218  -2.424  1.00  0.00           C  
HETATM   25  H1  UNL     1      -6.596  -2.525   1.445  1.00  0.00           H  
HETATM   26  H2  UNL     1      -6.375  -1.177   2.632  1.00  0.00           H  
HETATM   27  H3  UNL     1      -7.815  -1.196   1.468  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.362  -1.751   2.452  1.00  0.00           H  
HETATM   29  H5  UNL     1      -1.924  -1.566   2.460  1.00  0.00           H  
HETATM   30  H6  UNL     1       0.071   0.224  -0.245  1.00  0.00           H  
HETATM   31  H7  UNL     1       0.012  -1.350   2.351  1.00  0.00           H  
HETATM   32  H8  UNL     1       1.909   0.399  -0.288  1.00  0.00           H  
HETATM   33  H9  UNL     1       4.502  -0.757   2.140  1.00  0.00           H  
HETATM   34  H10 UNL     1       6.871  -0.427   1.936  1.00  0.00           H  
HETATM   35  H11 UNL     1       7.810   0.749  -0.044  1.00  0.00           H  
HETATM   36  H12 UNL     1       6.262   1.543  -1.754  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.802   2.849  -2.778  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.053   0.625  -1.182  1.00  0.00           H  
HETATM   39  H15 UNL     1      -3.739   2.242  -2.134  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.244   0.605  -2.838  1.00  0.00           H  
HETATM   41  H17 UNL     1      -4.825   1.367  -3.246  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3
CONECT    3    4    4   22
CONECT    4    5   28
CONECT    5    6    6   29
CONECT    6    7   21
CONECT    7    8    8   30
CONECT    8    9   31
CONECT    9   10   10   11
CONECT   11   12   32
CONECT   12   13   13   17
CONECT   13   14   33
CONECT   14   15   15   34
CONECT   15   16   35
CONECT   16   17   17   36
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   37
CONECT   21   22   22   38
CONECT   22   23
CONECT   23   24
CONECT   24   39   40   41
END

HMDB0249020
     RDKit          3D
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-
 41 42  0  0  0  0  0  0  0  0999 V2000
   -6.7441   -1.4299    1.6133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0083   -0.7650    0.6080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6208   -0.6736    0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8644   -1.2243    1.6443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4660   -1.1164    1.6459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7978   -0.4587    0.6438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3230   -0.3169    0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4525   -0.8077    1.5105 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8981   -0.6801    1.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5291   -1.2228    2.4637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5334    0.0048    0.4360 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9299    0.1834    0.3238 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8557   -0.2404    1.2536 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2285   -0.0515    1.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7310    0.5952    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8564    1.0324   -0.8941 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4651    0.8434   -0.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6355    1.3417   -1.8542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4109    1.2973   -2.0023 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2956    1.9994   -2.9336 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5669    0.0967   -0.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9381   -0.0163   -0.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7231    0.5377   -1.3820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0741    1.2179   -2.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5960   -2.5249    1.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3755   -1.1775    2.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8154   -1.1962    1.4676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3615   -1.7512    2.4521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9237   -1.5661    2.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0710    0.2242   -0.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124   -1.3502    2.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9089    0.3994   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5020   -0.7570    2.1400 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8707   -0.4267    1.9363 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8100    0.7489   -0.0443 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2615    1.5427   -1.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8025    2.8495   -2.7781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0532    0.6245   -1.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7394    2.2423   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2443    0.6047   -2.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8253    1.3673   -3.2458 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  2  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
  6 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 22  3  1  0
 17 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 20 37  1  0
 21 38  1  0
 24 39  1  0
 24 40  1  0
 24 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1 N-(3'-4'-Dimethoxycinnamoyl) anthranilic acid (N-5'), N(3',4'-dimethoxycinnamoyl) anthranilic acid (N-5')	MeSH
2-((3-(3,4-Dimethoxyphenyl)-1-oxo-2-propenyl)amino)benzoic acid	MeSH
Tranilast hydrate	MeSH
N (3', 4'-Dimethoxycinnamoyl) anthranilic acid (N-5')	MeSH
N-(3',4'-Dimethoxycinnamoyl)anthranilic acid	MeSH
Tranilast	MeSH
Rizaben	MeSH
Tranilast sodium salt	MeSH

Chemical Formula

C₁₈H₁₇NO₅

Average Molecular Weight

327.336

Monoisotopic Molecular Weight

327.110672651

IUPAC Name

2-[3-(3,4-dimethoxyphenyl)prop-2-enamido]benzoic acid

Traditional Name

tranilast

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C(C=CC(=O)NC2=CC=CC=C2C(O)=O)C=C1

InChI Identifier

InChI=1S/C18H17NO5/c1-23-15-9-7-12(11-16(15)24-2)8-10-17(20)19-14-6-4-3-5-13(14)18(21)22/h3-11H,1-2H3,(H,19,20)(H,21,22)

InChI Key

NZHGWWWHIYHZNX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-cinnamoylanthranilic acids. These are aromatic compounds containing a cinnamic acid conjugated to an anthranilic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid amides

Direct Parent

N-cinnamoylanthranilic acids

Alternative Parents

Substituents

N-cinnamoylanthranilic acid
Acylaminobenzoic acid or derivatives
O-dimethoxybenzene
Dimethoxybenzene
Benzoic acid or derivatives
Benzoic acid
Anilide
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Benzoyl
Styrene
N-arylamide
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous amide
Secondary carboxylic acid amide
Carboxamide group
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.89	ALOGPS
logP	3.56	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.86 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	91.52 m³·mol⁻¹	ChemAxon
Polarizability	34.26 Å³	ChemAxon
Number of Rings	2	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]+	174.565	30932474
DeepCCS	[M-H]-	172.207	30932474
DeepCCS	[M-2H]-	206.109	30932474
DeepCCS	[M+Na]+	181.909	30932474
AllCCS	[M+H]+	177.6	32859911
AllCCS	[M+H-H2O]+	174.4	32859911
AllCCS	[M+NH4]+	180.7	32859911
AllCCS	[M+Na]+	181.6	32859911
AllCCS	[M-H]-	178.9	32859911
AllCCS	[M+Na-2H]-	178.6	32859911
AllCCS	[M+HCOO]-	178.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-	COC1=C(OC)C=C(C=CC(=O)NC2=CC=CC=C2C(O)=O)C=C1	4708.3	Standard polar	33892256
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-	COC1=C(OC)C=C(C=CC(=O)NC2=CC=CC=C2C(O)=O)C=C1	3066.5	Standard non polar	33892256
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-	COC1=C(OC)C=C(C=CC(=O)NC2=CC=CC=C2C(O)=O)C=C1	3239.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-,2TMS,isomer #1	COC1=CC=C(C=CC(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C1OC	2916.7	Semi standard non polar	33892256
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-,2TMS,isomer #1	COC1=CC=C(C=CC(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C1OC	2976.1	Standard non polar	33892256
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-,2TMS,isomer #1	COC1=CC=C(C=CC(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C)[Si](C)(C)C)C=C1OC	3557.9	Standard polar	33892256
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-,2TBDMS,isomer #1	COC1=CC=C(C=CC(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	3400.1	Semi standard non polar	33892256
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-,2TBDMS,isomer #1	COC1=CC=C(C=CC(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	3352.8	Standard non polar	33892256
Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-,2TBDMS,isomer #1	COC1=CC=C(C=CC(=O)N(C2=CC=CC=C2C(=O)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1OC	3677.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-0956000000-76667488af9ce4be0287	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- 10V, Positive-QTOF	splash10-0006-0900000000-b9cd47e83309e8c31f5f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- 20V, Positive-QTOF	splash10-01ox-0900000000-bd19728246069b7a10dd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- 40V, Positive-QTOF	splash10-01x0-0920000000-34079cc2ac90e1a5628f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- 10V, Negative-QTOF	splash10-004i-0239000000-ab769a1db4100b7b83db	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- 20V, Negative-QTOF	splash10-0uxr-0290000000-fb85428e5ad08c98a6d9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- 40V, Negative-QTOF	splash10-0gbd-1590000000-be486d414eb47dc06ded	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5326

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5527

PDB ID

Not Available

ChEBI ID

92320

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]- (HMDB0249020)

MOL for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

3D MOL for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

3D SDF for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

3D-SDF for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

PDB for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

3D PDB for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

SMILES for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

INCHI for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

Structure for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

3D Structure for HMDB0249020 (Benzoic acid, 2-[[3-(3,4-dimethoxyphenyl)-1-oxo-2-propenyl]amino]-)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra