Compound: Homovanillic acid
SMILES: O=C(O)Cc1cc(OC)c(O)cc1
InChIKey: QRMZSPFSDQBLIX-UHFFFAOYSA-N
Synonyms: Homovanillic acid, 306-08-1, 4-Hydroxy-3-methoxyphenylacetic acid, 2-(4-hydroxy-3-methoxyphenyl)acetic acid, Benzeneacetic acid, 4-hydroxy-3-methoxy-, Vanillacetic acid, 3-Methoxy-4-hydroxyphenylacetic acid, 4-Hydroxy-3-methoxybenzeneacetic acid, (4-HYDROXY-3-METHOXYPHENYL)ACETIC ACID, Acetic acid, (4-hydroxy-3-methoxyphenyl)-, X77S6GMS36, DTXSID5059791, NSC-16682, HMDB00118, CHEBI:545959, Acid, Homovanillic, 3 Methoxy 4 Hydroxyphenylacetic Acid, 4 Hydroxy 3 Methoxyphenylacetic Acid, Acid, 3-Methoxy-4-Hydroxyphenylacetic, Acid, 4-Hydroxy-3-Methoxyphenylacetic, RefChem:38960, DTXCID4038219, 206-176-7, Homovanillate, Vanilacetic acid, HVA, MFCD00004350, Homovanilic acid, Homovanillinic acid, 3-Methoxy-4-hydroxyphenylacetate, 2-(4-hydroxy-3-methoxy-phenyl)acetic acid, NSC 16682, Homovaniuic acid, 2-(3-Methoxy-4-Oxidanyl-Phenyl)ethanoic Acid, UNII-X77S6GMS36, Homovanilate, Vanilacetate, homovanillic-acid, 4-HYDROXY-3-METHOXYPHENYLACETIC ACID (2,5,6-D3,ALPHA,ALPHA-D2), YTX, EINECS 206-176-7, 4-hydroxy-3-methoxy-benzeneacetic acid, Homovanillic acid; HVA, Homovanillic acid, 98%, Lopac-H-1252, bmse000132, SCHEMBL8792, 4-HYDROXY-3-(METHOXY)BENZENEACETIC ACID, CHEMBL1562, Homovanillic acid (Standard), Lopac0_000632, Oprea1_505423, MLS001056771, HOMOVANILLIC ACID [MI], orb1303423, orb3141111, SCHEMBL14764104, SCHEMBL27773950, HY-N0384R, QRMZSPFSDQBLIX-UHFFFAOYSA-, 4-Hydroxy-3-methoxybenzeneacetate, HMS2233B24, HMS3261P06, HMS3886C14, 4-hydroxy-3-methoxyphenyacetic acid, HY-N0384, MSK40053, NSC16682, STR09131, Homovanillic acidFluorimetric reagent, Tox21_500632, 4-hydroxy 3-methoxyphenylacetic acid, BBL100126, HB1902, s5642, SBB063413, STK372679, Homovanillic acid, analytical standard, 3-methoxy-4-hydroxy-phenylacetic acid, 4-hydroxy-3-methoxy-phenylacetic acid, 4-hydroxy-3-methoxyphenyl-acetic acid, AKOS005447065, CCG-204720, EBC-153075, FH23860, Homovanillic acid, Fluorimetric reagent, LP00632, PS-3625, SDCCGSBI-0050613.P002, 3-(Methoxy)-4-hydroxyphenylacetic acid, 4-Hydroxy-3-(methoxy)phenylacetic acid, NCGC00015497-01, NCGC00015497-02, NCGC00015497-03, NCGC00015497-04, NCGC00015497-05, NCGC00015497-08, NCGC00093999-01, NCGC00093999-02, NCGC00093999-03, NCGC00261317-01, 4-HYDROXY-3-METHOXY BENZENEACETIC, SMR000326729, ST097245, SY017698, (4-Hydroxy-3-methoxy-phenyl)-acetic acid, (4-hydroxy-3-methyoxy-phenyl)-acetic acid, CS-0008924, EU-0100632, H0339, NS00015133, acetic acid, 2-(4-hydroxy-3-methoxyphenyl)-, C05582, EN300-179380, H 1252, 4-HYDROXY-3-METHOXY-.ALPHA.-TOLUIC ACID, F002580, Q903566, SR-01000075364, Acetic acid, (4-hydroxy-3-methoxyphenyl)- (8CI), SR-01000075364-1, 4-Hydroxy-3-methoxyphenylacetic acid;Homovanillic acid, 562F45C3-F314-46F6-8FC2-74D84EBB9CBC, Z1203162033, InChI=1/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
Theoretical properties:
molecular_formula: C9H10O4
molecular_weight: 182.17 g/mol
exact_mass: 182.05790880 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 3
heavy_atom_count: 13
topological_polar_surface_area: 66.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 138 - 140 °C
solubility: 17 mg/mL
vapor_pressure: 0.00000823 [mmHg]
Descriptions:
pubchem: Homovanillic acid is a monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite. It has a role as a mouse metabolite and a human metabolite. It is a member of guaiacols and a monocarboxylic acid. It is functionally related to a (3,4-dihydroxyphenyl)acetic acid. It is a conjugate acid of a homovanillate.
chebi: A monocarboxylic acid that is the 3-<em>O</em>-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.
chembl: HOMOVANILLIC ACID is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Homovanillic acid (HVA) is a major catecholamine metabolite that is produced by a consecutive action of monoamine oxidase and catechol-O-methyltransferase on dopamine. Homovanillic acid is used as a reagent to detect oxidative enzymes, and is associated with dopamine levels in the brain.
In psychiatry and neuroscience, brain and cerebrospinal fluid levels of HVA are measured as a marker of metabolic stress caused by 2-deoxy-D-glucose.  HVA presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma.
Fasting plasma levels of HVA are known to be higher in females than in males. This does not seem to be influenced by adult hormonal changes, as the pattern is retained in the elderly and post-menopausal as well as transgender people according to their genetic sex, both before and during cross-sex hormone administration.  Differences in HVA have also been correlated to tobacco usage, with smokers showing significantly lower amounts of plasma HVA.