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Showing metabocard for (Z)-p-Methoxycinnamic acid (HMDB0246971)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:59:30 UTC
Update Date2021-09-26 22:56:23 UTC
HMDB IDHMDB0246971
Secondary Accession NumbersNone
Metabolite Identification
Common Name(Z)-p-Methoxycinnamic acid
Description4-methoxycinnamic acid belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. Based on a literature review a significant number of articles have been published on 4-methoxycinnamic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). (z)-p-methoxycinnamic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically (Z)-p-Methoxycinnamic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0246971 ((Z)-p-Methoxycinnamic acid)

  Mrv1652308231913562D          

 13 13  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
  7 10  1  4  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  1  1  0  0  0  0
 13  9  1  0  0  0  0
M  END
Download

3D MOL for HMDB0246971 ((Z)-p-Methoxycinnamic acid)

HMDB0246971
     RDKit          3D
(Z)-p-Methoxycinnamic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -4.3458    0.6240   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5975   -0.5405    0.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006   -0.5172    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -1.6375    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873   -1.5549    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191   -0.3839    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732   -0.3882    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7869    0.6832   -0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2445    0.6457   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    1.6591   -0.3734 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8543   -0.5615    0.1835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498    0.7231   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301    0.6513   -0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    1.0263   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4046    0.4296   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    1.4380    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9446   -2.5823    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5336   -2.4311    0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5918   -1.2989    0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    1.6256   -0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6734   -0.8161   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194    1.6660   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328    1.5401   -0.3323 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
  6 12  1  0
 12 13  2  0
 13  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for HMDB0246971 ((Z)-p-Methoxycinnamic acid)

  Mrv1652308231913562D          

 13 13  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  4  2  0  0  0  0
  8  2  2  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
  7 10  1  4  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  1  1  0  0  0  0
 13  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246971

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)

> <INCHI_KEY>
AFDXODALSZRGIH-UHFFFAOYSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.187

> <EXACT_MASS>
178.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.50677719280457

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-methoxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.978414994333333

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.309550178483235

> <JCHEM_PKA_STRONGEST_BASIC>
-4.823943866687228

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
49.523100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxycinnamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0246971 ((Z)-p-Methoxycinnamic acid)

HMDB0246971
     RDKit          3D
(Z)-p-Methoxycinnamic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -4.3458    0.6240   -0.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5975   -0.5405    0.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2006   -0.5172    0.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4508   -1.6375    0.4634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0873   -1.5549    0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6191   -0.3839    0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0732   -0.3882    0.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7869    0.6832   -0.1254 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2445    0.6457   -0.1182 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9429    1.6591   -0.3734 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8543   -0.5615    0.1835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1498    0.7231   -0.1307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5301    0.6513   -0.1105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9579    1.0263   -1.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4046    0.4296   -0.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1563    1.4380    0.6377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9446   -2.5823    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5336   -2.4311    0.6592 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5918   -1.2989    0.3720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193    1.6256   -0.3609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6734   -0.8161   -0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3194    1.6660   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1328    1.5401   -0.3323 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
  6 12  1  0
 12 13  2  0
 13  3  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  4 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 11 21  1  0
 12 22  1  0
 13 23  1  0
M  END
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PDB for HMDB0246971 ((Z)-p-Methoxycinnamic acid)

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2    5    8                                                       
CONECT    3    6    8                                                       
CONECT    4    7    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10                                                       
CONECT    8    2    3    4                                                  
CONECT    9    5    6   13                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0246971 ((Z)-p-Methoxycinnamic acid)

COMPND    HMDB0246971
HETATM    1  C1  UNL     1      -4.346   0.624  -0.099  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.598  -0.540   0.192  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.201  -0.517   0.184  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.451  -1.637   0.463  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.087  -1.555   0.440  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.619  -0.384   0.146  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.073  -0.388   0.144  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.787   0.683  -0.125  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.244   0.646  -0.118  1.00  0.00           C  
HETATM   10  O2  UNL     1       4.943   1.659  -0.373  1.00  0.00           O  
HETATM   11  O3  UNL     1       4.854  -0.561   0.183  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.150   0.723  -0.131  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.530   0.651  -0.111  1.00  0.00           C  
HETATM   14  H1  UNL     1      -3.958   1.026  -1.081  1.00  0.00           H  
HETATM   15  H2  UNL     1      -5.405   0.430  -0.257  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.156   1.438   0.638  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.945  -2.582   0.701  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.534  -2.431   0.659  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.592  -1.299   0.372  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.319   1.626  -0.361  1.00  0.00           H  
HETATM   21  H8  UNL     1       5.673  -0.816  -0.351  1.00  0.00           H  
HETATM   22  H9  UNL     1       0.319   1.666  -0.368  1.00  0.00           H  
HETATM   23  H10 UNL     1      -2.133   1.540  -0.332  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3
CONECT    3    4    4   13
CONECT    4    5   17
CONECT    5    6    6   18
CONECT    6    7   12
CONECT    7    8    8   19
CONECT    8    9   20
CONECT    9   10   10   11
CONECT   11   21
CONECT   12   13   13   22
CONECT   13   23
END
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SMILES for HMDB0246971 ((Z)-p-Methoxycinnamic acid)

COC1=CC=C(C=CC(O)=O)C=C1
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INCHI for HMDB0246971 ((Z)-p-Methoxycinnamic acid)

InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
3-(4-Methoxyphenyl)-2-propenoic acidChEBI
3-(4-Methoxyphenyl)acrylic acidChEBI
p-Methoxycinnamic acidChEBI
3-(4-Methoxyphenyl)-2-propenoateGenerator
3-(4-Methoxyphenyl)acrylateGenerator
p-MethoxycinnamateGenerator
4-MethoxycinnamateGenerator
3-(4-Methoxyphenyl)prop-2-enoateGenerator
4-Methoxy cinnamic acidMeSH
Chemical FormulaC10H10O3
Average Molecular Weight178.187
Monoisotopic Molecular Weight178.062994182
IUPAC Name3-(4-methoxyphenyl)prop-2-enoic acid
Traditional Name4-methoxycinnamic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=CC(O)=O)C=C1
InChI Identifier
InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)
InChI KeyAFDXODALSZRGIH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB092616
KNApSAcK IDC00051715
Chemspider ID12689
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID48541
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1204511
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]