HOMOVANILLIC ACID

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H10O4
Molecular Weight	182.1737
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COc1cc(ccc1O)CC(=O)O

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	182.1737
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 2 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 609
Target ID: Flucose oxidase, fungal Sources: https://www.ncbi.nlm.nih.gov/pubmed/5634544	Substrate 609
Xanthine dehydrogenase 29 Target ID: CHEMBL3649 Sources: https://www.ncbi.nlm.nih.gov/pubmed/5634544	Substrate 609

PubMed

Title	Date	PubMed
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.	1999 May 7	10224140
CSF studies in violent offenders. I. 5-HIAA as a negative and HVA as a positive predictor of psychopathy.	2001	11515752
Opposite genotype-dependent mesocorticolimbic dopamine response to stress.	2001	11440796
Effect of GBR 12909 and fluoxetine on the acute and long term changes induced by MDMA ('ecstasy') on the 5-HT and dopamine concentrations in mouse brain.	2001	11077072
The differential effect of angiotensin II and angiotensin 1-7 on norepinephrine, epinephrine, and dopamine concentrations in rat hypothalamus: the involvement of angiotensin receptors.	2001 Apr	11403997
Nitric oxide synthase inhibitors cause motor deficits in mice.	2001 Apr	11313158
Oxalic acid stabilizes dopamine, serotonin, and their metabolites in automated liquid chromatography with electrochemical detection.	2001 Apr 5	11334358
Site-specific activation of dopamine and serotonin transmission by aniracetam in the mesocorticolimbic pathway of rats.	2001 Apr 6	11282361
[Value of 123I-MIBG scanning, neuron-specific enolase and serum ferritin in the diagnosis and follow-up of patients with neuroblastoma].	2001 Aug	11470071
Gender-dependent enhanced adult neurotoxic response to methamphetamine following fetal exposure to the drug.	2001 Aug	11454941
A simple method to measure baseline occupancy of neostriatal dopamine D2 receptors by dopamine in vivo in healthy subjects.	2001 Aug	11425505
Continuous phencyclidine treatment induces schizophrenia-like hyperreactivity of striatal dopamine release.	2001 Aug	11425499
The cannabinoid CB(1) receptor antagonist SR141716A increases norepinephrine outflow in the rat anterior hypothalamus.	2001 Aug 31	11527547
Developmental changes in cerebrospinal fluid concentrations of monoamine-related substances in patients with dentatorubral-pallidoluysian atrophy.	2001 Feb	11292229
Differentiation of disulfiram effects on central catecholamines and hepatic ethanol metabolism.	2001 Feb	11169169
Evaluation of catecholamine metabolites, mIBG scan, and bone marrow cytology as response markers in stage 4 neuroblastoma.	2001 Jan	11464889
Observation of untreated patients with neuroblastoma detected by mass screening: a "wait and see" pilot study.	2001 Jan	11464874
Biphasic effects of selegiline on striatal dopamine: lack of effect on methamphetamine-induced dopamine depletion.	2001 Jan	11358284
Striatal dopamine sensitization to D-amphetamine in periadolescent but not in adult rats.	2001 Jan	11274716
CSF dopamine, serotonin, and biopterin metabolites in patients with restless legs syndrome.	2001 Jan	11215576
The effects of water-odor preference conditioning in the preadolescent nucleus accumbens septi.	2001 Jan	11150060
The central aromatic amino acid DOPA decarboxylase inhibitor, NSD-1015, does not inhibit L-DOPA-induced circling in unilateral 6-OHDA-lesioned-rats.	2001 Jan	11135014
Significance of glutamate and dopamine neurons in the ventral pallidum in the expression of behavioral sensitization to amphetamine.	2001 Jan 19	11212872
Distal infantile neuroaxonal dystrophy--a new familial variant with perineuronal argyrophilic bodies.	2001 Jul	11547955
Different action on dopamine catabolic pathways of two endogenous 1,2,3,4-tetrahydroisoquinolines with similar antidopaminergic properties.	2001 Jul	11432977
Biochemical and pathological study of endogenous 1-benzyl-1,2,3,4-tetrahydroisoquinoline-induced parkinsonism in the mouse.	2001 Jul 13	11430895
Motoric behavior in aged rats treated with GM1.	2001 Jul 6	11430865
Effects of repeated morphine treatment on metabolism of cerebral dopamine and serotonin in alcohol-preferring AA and alcohol-avoiding ANA rats.	2001 Jul-Aug	11468126
Long term effects of Toki-shakuyaku-san on brain dopamine and nerve growth factor in olfactory-bulb-lesioned mice.	2001 Jun	11459120
Long-term administration of N-acetylcysteine decreases hydrogen peroxide exhalation in subjects with chronic obstructive pulmonary disease.	2001 Jun	11421501
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
Inhibition of cytochrome P450 2E1 induces an increase in extracellular dopamine in rat substantia nigra: a new metabolic pathway?	2001 Jun 15	11309845
Oxygen inhalation enhances striatal dopamine metabolism and monoamineoxidase enzyme inhibition prevents it: a microdialysis study.	2001 Jun 22	11430914
Effect of embryonic knock-down of GABAA receptors on the levels of monoamines and their metabolites in the CNS of the mouse.	2001 Jun 22	11406127
Differential abnormalities in plasma 5-HIAA and platelet serotonin concentrations in violent suicide attempters: relationships with impulsivity and depression.	2001 Jun 29	11476186
3,4-Methylenedioxymethamphetamine induces monoamine release, but not toxicity, when administered centrally at a concentration occurring following a peripherally injected neurotoxic dose.	2001 Mar	11351932
Increased extracellular DA and normal evoked DA release in the rat striatum after a partial lesion of the substantia nigra.	2001 Mar 2	11223005
[Involvement of dopaminergic systems in the functional specialization of brain areas during formation of aggressive and submissive behavior in mice].	2001 Mar-Apr	11548601
Chronic estrogen treatment replaces striatal dopaminergic function in ovariectomized rats.	2001 May 11	11334794
BIA 3-202, a novel catechol-O-methyltransferase inhibitor, enhances the availability of L-DOPA to the brain and reduces its O-methylation.	2001 May 18	11412836
Nomifensine reveals age-related changes in K(+)-evoked striatal DA overflow in F344 rats.	2001 May-Jun	11378257
Effect of clonazepam treatment on antipsychotic drug-induced Meige syndrome and changes in plasma levels of GABA, HVA, and MHPG during treatment.	2001 Oct	11555353
Effect of chronic protein restriction on motor co-ordination and brain neurotransmitters in albino rats.	2001 Oct	11524142
Aging increases the susceptiblity to methamphetamine-induced dopaminergic neurotoxicity in rats: correlation with peroxynitrite production and hyperthermia.	2001 Sep	11553669
Heart failure, aging, and renal synthesis of dopamine.	2001 Sep	11532681

Patents

Substance Class	Chemical Created by `admin` on `Sat Jun 26 04:44:49 UTC 2021` Edited by `admin` on `Sat Jun 26 04:44:49 UTC 2021`
Record UNII	X77S6GMS36
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

HMDB00118

Code

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