Metabolite Card

Formula: C9H10O4 (182.0579)
SMILES: COC1=C(O)C=CC(CC(O)=O)=C1

Synonyms [en]

Homovanillic acid; Homovanillate; 3-Methoxy-4-hydroxyphenylacetate; Vanillacetic acid; 3-Methoxy-4-hydroxyphenylacetic acid; (4-HYDROXY-3-METHOXYPHENYL)ACETIC ACID

Reviewed

Last reviewed on 2024-06-28.

Cite this Page

Homovanillate. 数据之源,洞见之始. SMRUCC genomics institute, a synthetic life researcher from China. https://biocad_registry.innovation.ac.cn/s/(-)-arctiin (retrieved 2026-01-03) (CAD Registry RN: BioCAD00000012176). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Note

Homovanillic acid (HVA), also known as homovanillate, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. HVA is also classified as a catechol. HVA is a major catecholamine metabolite that is produced by a consecutive action of monoamine oxidase and catechol-O-methyltransferase on dopamine. HVA is typically elevated in patients with catecholamine-secreting tumors (such as neuroblastoma, pheochromocytoma, and other neural crest tumors). HVA levels are also used in monitoring patients who have been treated for these kinds tumors. HVA levels may also be altered in disorders of catecholamine metabolism such as monoamine oxidase-A (MOA) deficiency. MOA deficiency can cause decreased urinary HVA values, while a deficiency of dopamine beta-hydrolase (the enzyme that converts dopamine to norepinephrine) can cause elevated urinary HVA values. Within humans, HVA participates in a number of enzymatic reactions. In particular, HVA and pyrocatechol can be biosynthesized from 3,4-dihydroxybenzeneacetic acid and guaiacol. This reaction is catalyzed by the enzyme known as catechol O-methyltransferase. In addition, HVA can be biosynthesized from homovanillin through the action of the enzyme known aldehyde dehydrogenase. HVA has recently been found in a number of beers and appears to arise from the fermentation process (https://doi.org/10.1006/fstl.1999.0593). HVA is also a metabolite of Bifidobacterium (PMID: 24958563) and the bacterial breakdown of dietary flavonoids. Dietary flavonols commonly found in tomatoes, onions, and tea, can lead to significantly elevated levels of urinary HVA (PMID: 20933512). Likewise, the microbial digestion of hydroxytyrosol (found in olive oil) can also lead to elevated levels of HVA in humans (PMID: 11929304).

Entity Information

DBLinks

Other DBLinks
  • CAS Registry Number: 20503-09-7
  • CAS Registry Number: 306-08-1
  • CAS Registry Number: 53587-33-0
  • PubChem: 1738
  • PubChem: 7908
  • ChEBI: ChEBI:545959
  • HMDB: HMDB0000118
  • KEGG: C05582
  • BioCyc: CPD-7651
  • NCBI MeSH: Homovanillic Acid
  • Wikipedia: Homovanillic_acid
  • RefMet: RM0042979
  • MoNA: BAF_UVA_POS000496
  • MoNA: BAF_UVA_POS000692
  • MoNA: BAF_UVA_POS000693
  • MoNA: BAF_UVA_POS000694
  • MoNA: Bruker_HCD_library000371
  • MoNA: CCMSLIB00000578354
  • MoNA: CCMSLIB00005720846
  • MoNA: FiehnHILIC001251
  • MoNA: FiehnHILIC002752
  • MoNA: FiehnLib000971
  • MoNA: GLS00077
  • MoNA: HMDB0000118_c_ms_1439
  • MoNA: HMDB0000118_ms_ms_168
  • MoNA: HMDB0000118_ms_ms_169
  • MoNA: HMDB0000118_ms_ms_170
  • MoNA: JP004522
  • MoNA: KO001071
  • MoNA: KO001072
  • MoNA: KO001073
  • MoNA: KO001074
  • MoNA: KO001075
  • MoNA: MoNA003260
  • MoNA: MoNA016882
  • MoNA: MoNA032473
  • MoNA: MoNA032474
  • MoNA: MoNA032475
  • MoNA: MoNA033552
  • MoNA: MoNA033553
  • MoNA: MoNA033555
  • MoNA: MoNA034550
  • MoNA: MoNA034551
  • MoNA: MoNA034552
  • MoNA: MoNA035665
  • MoNA: MoNA035666
  • MoNA: MoNA035668
  • MoNA: MoNA036932
  • MoNA: MoNA036933
  • MoNA: MoNA036935
  • MoNA: MoNA037313
  • MoNA: MoNA037674
  • MoNA: MoNA038052
  • MoNA: MoNA038408
  • MoNA: OUF00354
  • MoNA: PM002310
  • MoNA: PS098801
  • MoNA: PS098803
  • MoNA: PS098807
  • MoNA: RP018201
  • MoNA: RP018202
  • MoNA: RP018203
  • MoNA: RP018211
  • MoNA: RP018212
  • MoNA: VF-NPL-LTQ000293
  • MoNA: VF-NPL-LTQ000294
  • MoNA: VF-NPL-QEHF000622
  • MoNA: VF-NPL-QEHF000623
  • MoNA: VF-NPL-QEHF000624
  • MoNA: VF-NPL-QEHF000625
  • MoNA: VF-NPL-QEHF000626
  • MoNA: VF-NPL-QEHF000627
  • Metlin: METLIN_971
  • Coconut NaturalProduct: CNP0188137.0
  • Coconut NaturalProduct: CNP0239375.0
  • Coconut NaturalProduct: CNP0605619.0

Class / Ontology

Metabolic Network
ID EC Number Name
KEGG:R03304 2.1.1.6 S-adenosyl-L-methionine:catechol O-methyltransferase
KEGG:R04888 1.2.1.5 3-methoxy-4-hydroxyphenylacetaldehyde:NAD+ oxidoreductase
KEGG:R04889 1.2.1.5 3-methoxy-4-hydroxyphenylacetaldehyde:NADP+ oxidoreductase
BioCyc:RXN-10877 homovanillate synthase
BioCyc:RXN6666-6 2.1.1.6 S-ADENOSYLMETHIONINE + CPD-782 --> PROTON + CPD-7651 + ADENOSYL-HOMO-CYS
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Organism Source

Taxonomy Source

  1. Aloe africana [ncbi taxid: 1080010]
  2. Aloe ferox [ncbi taxid: 117798]
  3. Aloe spicata [ncbi taxid: 992642]
  4. Aloe vera [ncbi taxid: 34199]
  5. Homo sapiens [ncbi taxid: 9606]
  6. Jatropha curcas [ncbi taxid: 180498]
  7. Mus musculus [ncbi taxid: 10090]
  8. Olea europaea [ncbi taxid: 4146]
  9. Persea americana [ncbi taxid: 3435]
  10. Thymus quinquecostatus [ncbi taxid: 228974]
  11. Thymus vulgaris [ncbi taxid: 49992]

Pathway Synthetic

pathway id name
Reactome:R-BTA-379397 Enzymatic degradation of dopamine by COMT
Reactome:R-CFA-112315 Transmission across Chemical Synapses
Reactome:R-CFA-112311 Neurotransmitter clearance
Reactome:R-DRE-112315 Transmission across Chemical Synapses
Reactome:R-DRE-112311 Neurotransmitter clearance
Reactome:R-DDI-112311 Neurotransmitter clearance
Reactome:R-GGA-379398 Enzymatic degradation of Dopamine by monoamine oxidase
Reactome:R-HSA-112315 Transmission across Chemical Synapses
Reactome:R-HSA-112311 Neurotransmitter clearance
Reactome:R-MMU-379398 Enzymatic degradation of Dopamine by monoamine oxidase
Reactome:R-RNO-112316 Neuronal System
Reactome:R-RNO-379401 Clearance of dopamine
Reactome:R-SPO-112316 Neuronal System
Reactome:R-SPO-379398 Enzymatic degradation of Dopamine by monoamine oxidase
Reactome:R-SSC-112315 Transmission across Chemical Synapses
Reactome:R-SSC-112311 Neurotransmitter clearance
Reactome:R-XTR-379398 Enzymatic degradation of Dopamine by monoamine oxidase
Reactome:R-BTA-112316 Neuronal System
Reactome:R-BTA-379401 Clearance of dopamine
Reactome:R-CFA-379398 Enzymatic degradation of Dopamine by monoamine oxidase
View All Pathways