| Common Name |
Isohomovanillic acid
| Description |
Isohomovanillic acid is a deaminated metabolite of catecholamines formed by the enzyme catechol-O-methyltransferase (COMT; EC 2.1.1.6) which catalyzes the transfer of a methyl group from S-adenosylmethionine to catecholamines, including the neurotransmitters dopamine, epinephrine, and norepinephrine. This O-methylation reslits in one of the major degradative pathways of the catecholamine transmitters. (OMIM 116790 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
Homoisovanillic acidChEBI
HomoisovanillateGenerator
IsohomovanillateGenerator
3-Hydroxy-4-methoxyphenylacetateHMDB
3-Hydroxy-4-methoxyphenylacetic acidHMDB
4-Methoxy-3-hydroxyphenylacetateHMDB
4-Methoxy-3-hydroxyphenylacetic acidHMDB
homo-iso-Vanillic acidMeSH
| Chemical Formlia |
C9H10O4
| Average Molecliar Weight |
182.1733
| Monoisotopic Molecliar Weight |
182.057908808
| IUPAC Name |
2-(3-hydroxy-4-methoxyphenyl)acetic acid
| Traditional Name |
isohomovanillic acid
| CAS Registry Number |
1131-94-8
| SMILES |
COC1=CC=C(CC(O)=O)C=C1O
| InChI Identifier |
InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)
| InChI Key |
BWXLCOBSWMQCGP-UHFFFAOYSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Benzenoids
| Sub Class |
Phenols
| Direct Parent |
Methoxyphenols
| Alternative Parents |
Phenoxy compounds
Methoxybenzenes
Anisoles
Alkyl aryl ethers
1-hydroxy-4-unsubstituted benzenoids
1-hydroxy-2-unsubstituted benzenoids
Monocarboxylic acids and derivatives
Carboxylic acids
Organic oxides
Hydrocarbon derivatives
Carbonyl compounds
| Substituents |
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound
| Molecliar Framework |
Aromatic homomonocyclic compounds
| External Descriptors |
aromatic ether (CHEBI:70818 )
monocarboxylic acid (CHEBI:70818 )
phenols (CHEBI:70818 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Cytoplasm (predicted from logP)
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility2.64 mg/mLALOGPS
logP0.88ALOGPS
logP1.15ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.74ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.81 m3·mol-1ChemAxon
Polarizability17.72 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
Not Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm (predicted from logP)
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB021958
| KNApSAcK ID |
Not Available
| Chemspider ID |
141092
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00333
| Metagene Link |
HMDB00333
| METLIN ID |
5322
| PubChem Compound |
160562
| PDB ID |
Not Available
| ChEBI ID |
823536
Product: (R)-(-)-Phenylephrine
References |
| Synthesis Reference |
Harlay, Victor. Synthesis of homoisovanillic acid. New method for the preparation of homoveratric acid. Compt. rend. (1946), 223 675-7. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Muskiet FA, Fremouw-Ottevangers DC, Nagel GT, Wolthers BG: Determination of 4-O-methylated catecholamine metabolites in urine by mass fragmentography. Clin Chem. 1979 Oct;25(10):1708-13. [PubMed:476919 ]
|
Enzymes
- General function:
- Involved in magnesium ion binding
- Specific function:
- Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
- Gene Name:
- COMT
- Uniprot ID:
- P21964
- Molecular weight:
- 30036.77
PMID: 7476923