HOMOVANILLIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10O4
Molecular Weight	182.1733
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(O)C=CC(CC(O)=O)=C1

InChI

InChIKey=QRMZSPFSDQBLIX-UHFFFAOYSA-N

InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)

HIDE SMILES / InChI

Molecular Formula	C9H10O4
Molecular Weight	182.1733
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Peroxidase C1A 3 Target ID: P00433 Gene ID: NA Gene Symbol: PRXC1A Target Organism: Armoracia rusticana (Horseradish) (Armoracia laphatifolia) Sources: https://www.ncbi.nlm.nih.gov/pubmed/5634544	Substrate 661
Flucose oxidase, fungal 1 Target ID: Flucose oxidase, fungal Sources: https://www.ncbi.nlm.nih.gov/pubmed/5634544	Substrate 661
Xanthine dehydrogenase 33 Target ID: CHEMBL3649 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5634544	Substrate 661

PubMed

Title	Date	PubMed
Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment.	1979 Aug 8	115032
CSF studies in violent offenders. I. 5-HIAA as a negative and HVA as a positive predictor of psychopathy.	2001	11515752
Decreased densities of dopamine and serotonin transporters and of vesicular monoamine transporter 2 in severely kainic acid lesioned subregions of the striatum.	2001	11475010
Opposite genotype-dependent mesocorticolimbic dopamine response to stress.	2001	11440796
Site-specific activation of dopamine and serotonin transmission by aniracetam in the mesocorticolimbic pathway of rats.	2001 Apr 6	11282361
Effect of intracerebral 6-nitronoradrenaline, an endogenous catechol-O-methyltransferase (COMT) inhibitor, on striatal dopamine metabolism in anaesthetised rats.	2001 Aug 15	11489299
CSF dopamine, serotonin, and biopterin metabolites in patients with restless legs syndrome.	2001 Jan	11215576
Monoamine compounds in cerebrospinal fluid of healthy subjects punctured without preceding strict bed rest: a pilot study.	2001 Jan	11150891
The effects of water-odor preference conditioning in the preadolescent nucleus accumbens septi.	2001 Jan	11150060
Involvement of D2 dopamine receptors in the opposing effects of two CCK-B agonists in a spatial recognition memory task: role of the anterior nucleus accumbens.	2001 Jan 1	11205416
Characterization of extracellular dopamine clearance in the medial prefrontal cortex: role of monoamine uptake and monoamine oxidase inhibition.	2001 Jan 1	11150317
Significance of glutamate and dopamine neurons in the ventral pallidum in the expression of behavioral sensitization to amphetamine.	2001 Jan 19	11212872
A novel neurodevelopmental syndrome responsive to 5-hydroxytryptophan and carbidopa.	2001 Jun	11386854
Dopaminergic changes in human brain following acute exposure to gamma-hydroxybutyrate.	2001 Jun 12	11402130
Effects of intrastriatal infusion of D2 and D3 dopamine receptor preferring antagonists on dopamine release in rat dorsal striatum (in vivo microdialysis study).	2001 Mar	11401421
In vivo effects of inorganic mercury (HgCl(2)) on striatal dopaminergic system.	2001 Mar	11222035
Biogenic amine metabolites and thiamine in cerebrospinal fluid in heredo-degenerative ataxias.	2001 May	11383938
Striatal dopaminergic and serotonergic markers in human heroin users.	2001 May	11282256
Nomifensine reveals age-related changes in K(+)-evoked striatal DA overflow in F344 rats.	2001 May-Jun	11378257
Effect of chronic protein restriction on motor co-ordination and brain neurotransmitters in albino rats.	2001 Oct	11524142
In-use stability of monoamine metabolites in human cerebrospinal fluid.	2001 Sep 5	11530989

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:13:24 GMT 2025` Edited by `admin` on `Mon Mar 31 19:13:24 GMT 2025`
Record UNII	X77S6GMS36
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HMDB00118

Preferred Name

English

HOMOVANILLIC ACID

Systematic Name

English

HVA

Common Name

English

4-HYDROXY-3-METHOXY-.ALPHA.-TOLUIC ACID

Systematic Name

English

VANILACETIC ACID

Common Name

English

HOMOVANILLIC ACID [MI]

Common Name

English

NSC-16682

Code

English

(4-HYDROXY-3-METHOXYPHENYL)ACETIC ACID

Systematic Name

English

3-METHOXY-4-HYDROXYPHENYLACETIC ACID

Systematic Name

English

4-HYDROXY-3-METHOXYBENZENEACETIC ACID

Systematic Name

English

Code System Code Type Description

FDA UNII

X77S6GMS36