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Showing metabocard for Isovanillic acid (HMDB0060003)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2013-04-09 21:19:03 UTC
Update Date2023-02-21 17:29:40 UTC
HMDB IDHMDB0060003
Secondary Accession Numbers
  • HMDB60003
Metabolite Identification
Common NameIsovanillic acid
DescriptionIsovanillic acid, also known as acide isovanillique or 3-hydroxy-p-anisate, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. Isovanillic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a selective inhibitor of aldehyde oxidase. Isovanillic acid is a metabolite of isovanillin. Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid.
Structure
Data?1677000579
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0060003 (Isovanillic acid)

  Mrv0541 04091314192D          

 12 12  0  0  0  0            999 V2000
    6.2464    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    3.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    3.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6754    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    2.1804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    1.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6754    4.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898    3.4179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    1.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
M  END
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3D MOL for HMDB0060003 (Isovanillic acid)

HMDB0060003
     RDKit          3D
Isovanillic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.2251    0.9597    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3894   -0.0531   -0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311   -0.1324   -0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551    0.8196    0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984    0.7589    0.7527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837   -0.3132    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115   -0.4001    0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465   -1.3546   -0.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7807    0.5475    1.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988   -1.2765   -0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3558   -1.2017   -0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -2.1806   -1.4818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2350    0.4990    0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719    1.8504   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    1.2236    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8844    1.6727    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980    1.5172    1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3416    1.2952    0.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -2.1110   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -2.1206   -1.6306 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  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  9 18  1  0
 10 19  1  0
 12 20  1  0
M  END
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3D SDF for HMDB0060003 (Isovanillic acid)

  Mrv0541 04091314192D          

 12 12  0  0  0  0            999 V2000
    6.2464    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    3.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5320    2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    2.1803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    2.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9609    3.4179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6754    3.8304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    2.1804    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2464    1.3553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6754    4.6554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3898    3.4179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8175    1.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  7 10  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060003

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)

> <INCHI_KEY>
LBKFGYZQBSGRHY-UHFFFAOYSA-N

> <FORMULA>
C8H8O4

> <MOLECULAR_WEIGHT>
168.1467

> <EXACT_MASS>
168.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
15.894359785080015

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-4-methoxybenzoic acid

> <ALOGPS_LOGP>
1.81

> <JCHEM_LOGP>
1.1695921366666666

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.958072873488197

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.147477192001137

> <JCHEM_PKA_STRONGEST_BASIC>
-4.911668652620585

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
41.758300000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovanillic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0060003 (Isovanillic acid)

HMDB0060003
     RDKit          3D
Isovanillic acid
 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.2251    0.9597    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3894   -0.0531   -0.3925 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0311   -0.1324   -0.1887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3551    0.8196    0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984    0.7589    0.7527 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6837   -0.3132    0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1115   -0.4001    0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465   -1.3546   -0.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7807    0.5475    1.1395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988   -1.2765   -0.5307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3558   -1.2017   -0.7367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396   -2.1806   -1.4818 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2350    0.4990    0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2719    1.8504   -0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8691    1.2236    1.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8844    1.6727    0.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4980    1.5172    1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3416    1.2952    0.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352   -2.1110   -0.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0380   -2.1206   -1.6306 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  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
 11 12  1  0
 11  3  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  4 16  1  0
  5 17  1  0
  9 18  1  0
 10 19  1  0
 12 20  1  0
M  END
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PDB for HMDB0060003 (Isovanillic acid)

HEADER    PROTEIN                                 09-APR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-APR-13         0                                  
HETATM    1  C   UNK     0      11.660   7.150   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.326   6.380   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.326   4.840   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.660   4.070   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.994   4.840   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.994   6.380   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.327   7.150   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.993   4.070   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      11.660   2.530   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      14.327   8.690   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      15.661   6.380   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.993   2.530   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6   10   11                                                  
CONECT    8    3   12                                                       
CONECT    9    4                                                            
CONECT   10    7                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END
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3D PDB for HMDB0060003 (Isovanillic acid)

COMPND    HMDB0060003
HETATM    1  C1  UNL     1      -3.225   0.960   0.090  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.389  -0.053  -0.393  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.031  -0.132  -0.189  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.355   0.820   0.538  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.998   0.759   0.753  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.684  -0.313   0.205  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.111  -0.400   0.417  1.00  0.00           C  
HETATM    8  O2  UNL     1       3.746  -1.355  -0.066  1.00  0.00           O  
HETATM    9  O3  UNL     1       3.781   0.548   1.139  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.999  -1.276  -0.531  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.356  -1.202  -0.737  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.040  -2.181  -1.482  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.235   0.499   0.247  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.272   1.850  -0.575  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.869   1.224   1.120  1.00  0.00           H  
HETATM   16  H4  UNL     1      -0.884   1.673   0.977  1.00  0.00           H  
HETATM   17  H5  UNL     1       1.498   1.517   1.324  1.00  0.00           H  
HETATM   18  H6  UNL     1       4.342   1.295   0.766  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.535  -2.111  -0.957  1.00  0.00           H  
HETATM   20  H8  UNL     1      -2.038  -2.121  -1.631  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   16
CONECT    5    6    6   17
CONECT    6    7   10
CONECT    7    8    8    9
CONECT    9   18
CONECT   10   11   11   19
CONECT   11   12
CONECT   12   20
END
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SMILES for HMDB0060003 (Isovanillic acid)

COC1=CC=C(C=C1O)C(O)=O
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INCHI for HMDB0060003 (Isovanillic acid)

InChI=1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-Hydroxy-p-anisic acidChEBI
3-Hydroxyanisic acidChEBI
Acide isovanilliqueChEBI
3-Hydroxy-p-anisateGenerator
3-HydroxyanisateGenerator
IsovanillateGenerator
3-Hydroxy-4-methoxybenzoateHMDB
Isovanillic acidChEBI
3-Hydroxy-4-methoxybenzoic acidHMDB
Chemical FormulaC8H8O4
Average Molecular Weight168.1467
Monoisotopic Molecular Weight168.042258744
IUPAC Name3-hydroxy-4-methoxybenzoic acid
Traditional Nameisovanillic acid
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C=C1O)C(O)=O
InChI Identifier
InChI=1S/C8H8O4/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,9H,1H3,(H,10,11)
InChI KeyLBKFGYZQBSGRHY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentP-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • P-methoxybenzoic acid or derivatives
  • Hydroxybenzoic acid
  • Methoxyphenol
  • Benzoic acid
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.328 +/- 0.093 umol/mmol creatinineAdult (>18 years old)MaleNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12575
PDB IDNot Available
ChEBI ID63798
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Loke WM, Jenner AM, Proudfoot JM, McKinley AJ, Hodgson JM, Halliwell B, Croft KD: A metabolite profiling approach to identify biomarkers of flavonoid intake in humans. J Nutr. 2009 Dec;139(12):2309-14. doi: 10.3945/jn.109.113613. Epub 2009 Oct 7. [PubMed:19812218 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Isovanillic acid → 6-(5-carboxy-2-methoxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Isovanillic acid → 3,4,5-trihydroxy-6-(3-hydroxy-4-methoxybenzoyloxy)oxane-2-carboxylic aciddetails
Enzyme Details
2. Glycine N-acyltransferase
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
Isovanillic acid → 2-{[hydroxy(3-hydroxy-4-methoxyphenyl)methylidene]amino}acetic aciddetails
Enzyme Details
3. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Isovanillic acid → 4-methoxy-3-(sulfooxy)benzoic aciddetails