3,4-Dihydroxyphenylacetate (BioCAD00000003878)
Metabolite Card
Formula: C8H8O4 (168.0423)
SMILES: OC(=O)CC1=CC(O)=C(O)C=C1
Synonyms [en]
3,4-Dihydroxyphenylacetic acid; 3,4-dihydroxyphenylacetate; 3,4-dihydroxyphenyl acetic acid; Dihydroxyphenylacetic acid; Homoprotocatechuate; Dopacetic acid
Last reviewed on 2024-06-28.
Cite this Page
3,4-Dihydroxyphenylacetate. 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: BioCAD00000003878). Licensed
under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Note
3,4-Dihydroxyphenylacetic acid (DOPAC) is a phenolic acid. DOPAC is a neuronal metabolite of dopamine (DA). DA undergoes monoamine oxidase-catalyzed oxidative deamination to 3,4-dihydroxyphenylacetaldehyde (DOPAL), which is metabolized primarily into DOPAC via aldehyde dehydrogenase (ALDH2). The biotransformation of DOPAL is critical as previous studies have demonstrated this DA-derived aldehyde to be a reactive electrophile and toxic to dopaminergic cells. Known inhibitors of mitochondrial ALDH2, such as 4-hydroxy-2-nonenal (4HNE) inhibit ALDH2-mediated oxidation of the endogenous neurotoxin DOPAL. 4HNE is one of the resulting products of oxidative stress, thus linking oxidative stress to the uncontrolled production of an endogenous neurotoxin relevant to Parkinson's disease. In early-onset Parkinson disease, there is markedly reduced activities of both monoamine oxidase (MAO) A and B. The amount of DOPAC, which is produced during dopamine oxidation by MAO, is greatly reduced as a result of increased parkin overexpression. Administration of methamphetamine to animals causes loss of DA terminals in the brain and significant decreases in dopamine and dihydroxyphenylacetic acid (DOPAC) in the striatum. Renal dopamine produced in the residual tubular units may be enhanced during a sodium challenge, thus behaving appropriately as a compensatory natriuretic hormone; however, the renal dopaminergic system in patients afflicted with renal parenchymal disorders should address parameters other than free urinary dopamine, namely the urinary excretion of L-DOPA and metabolites. DOPAC is one of the major phenolic acids formed during human microbial fermentation of tea, citrus, and soy flavonoid supplements. DOPAC exhibits a considerable antiproliferative effect in LNCaP prostate cancer and HCT116 colon cancer cells. The antiproliferative activity of DOPAC may be due to its catechol structure. A similar association of the catechol moiety in the B-ring with antiproliferative activity was demonstrated for flavanones (PMID:16956664, 16455660, 8561959, 11369822, 10443478, 16365058). DOPAC can be found in Gram-positive bacteria (PMID:24752840).
DBLinks
- CAS Registry Number: 102-32-9
- PubChem CID: 547
- ChEBI: 17612
- HMDB: HMDB0001336
- LipidMaps:
- KEGG: C01161
- BioCyc:
- NCBI MeSH: 3,4-Dihydroxyphenylacetic Acid
- Wikipedia: DOPAC
Other DBLinks
- CAS Registry Number: 102-32-9
- PubChem: 4388
- PubChem: 547
- ChEBI: ChEBI:1386
- ChEBI: ChEBI:17612
- ChEBI: ChEBI:41941
- HMDB: HMDB0001336
- KEGG: C01161
- NCBI MeSH: 3,4-Dihydroxyphenylacetic Acid
- Wikipedia: 3,4-Dihydroxyphenylacetic_acid
- Wikipedia: DOPAC
- DrugBank: DB01702
- RefMet: RM0136062
- MoNA: BAF_UVA_POS001230
- MoNA: BAF_UVA_POS001231
- MoNA: BAF_UVA_POS001399
- MoNA: EMBL-MCF_spec75335
- MoNA: EMBL-MCF_spec75984
- MoNA: FiehnHILIC000942
- MoNA: FiehnHILIC002487
- MoNA: FiehnLib000189
- MoNA: HMDB0001336_c_ms_1498
- MoNA: HMDB0001336_ms_ms_1519
- MoNA: HMDB0001336_ms_ms_1520
- MoNA: HMDB0001336_ms_ms_1521
- MoNA: KZ000174
- MoNA: MoNA034404
- MoNA: MoNA034406
- MoNA: MoNA034407
- MoNA: MoNA038001
- MoNA: OUF00044
- MoNA: PM002309
- MoNA: PM015331
- MoNA: PR010219
- MoNA: PS046607
- MoNA: PS046608
- Metlin: METLIN_968
- Coconut NaturalProduct: CNP0276169.0
Class / Ontology
- WishartLab ClassyFire: [Benzenediols] Benzenediols
- RefMet: [Hydroxybenzoic acids] Hydroxybenzoic acids
- ChEBI: [CHEBI:41941] (3,4-dihydroxyphenyl)acetic acid
- Coconut NaturalProduct: [Simple phenolic acids] Simple phenolic acids
| ID | EC Number | Name |
|---|---|---|
| KEGG:R02698 | 1.14.14.9 | 4-hydroxyphenylacetate,NADH:oxygen oxidoreductase (3-hydroxylating) |
| KEGG:R03299 | 1.14.14.9 | 3-hydroxyphenylacetate,NADH:oxygen oxidoreductase (3-hydroxylating) |
| KEGG:R03300 | 1.2.1.5 | 3,4-dihydroxyphenylacetaldehyde:NAD+ oxidoreductase |
| KEGG:R03302 | 1.2.1.5 | 3,4-dihydroxyphenylacetaldehyde:NADP+ oxidoreductase |
| KEGG:R03303 | 1.13.11.15 | 3,4-dihydroxyphenylacetate:oxygen 2,3-oxidoreductase (decyclizing) |
| KEGG:R03304 | 2.1.1.6 | S-adenosyl-L-methionine:catechol O-methyltransferase |
| KEGG:R03306 | 1.14.12.9 | 4-chlorophenylacetate,NADH:oxygen oxidoreductase (3,4-hydroxylating, dechlorinating) |
| KEGG:R13085 | C22552 + 2 C00001<=>C01161 + C02183 + C00011 + 2 C00080 | |
| Rhea:RHEA:14690 | 1.14.12.9 | 4-chlorophenylacetate + NADH + O2 => 3,4-dihydroxyphenylacetate + chloride + NAD+ |
| Rhea:RHEA:14691 | 1.14.12.9 | 3,4-dihydroxyphenylacetate + chloride + NAD+ => 4-chlorophenylacetate + NADH + O2 |
| Rhea:RHEA:14692 | 1.14.12.9 | 4-chlorophenylacetate + NADH + O2 <=> 3,4-dihydroxyphenylacetate + chloride + NAD+ |
| Rhea:RHEA:15634 | 1.13.11.15 | 3,4-dihydroxyphenylacetate + O2 => 2-hydroxy-5-carboxymethylmuconate semialdehyde + H+ |
| Rhea:RHEA:15635 | 1.13.11.15 | 2-hydroxy-5-carboxymethylmuconate semialdehyde + H+ => 3,4-dihydroxyphenylacetate + O2 |
| Rhea:RHEA:15636 | 1.13.11.15 | 3,4-dihydroxyphenylacetate + O2 <=> 2-hydroxy-5-carboxymethylmuconate semialdehyde + H+ |
| Rhea:RHEA:30596 | 1.14.14.9 | 4-hydroxyphenylacetate + FADH2 + O2 => 3,4-dihydroxyphenylacetate + FAD + H2O + H+ |
| Rhea:RHEA:30597 | 1.14.14.9 | 3,4-dihydroxyphenylacetate + FAD + H2O + H+ => 4-hydroxyphenylacetate + FADH2 + O2 |
| Rhea:RHEA:30598 | 1.14.14.9 | 4-hydroxyphenylacetate + FADH2 + O2 <=> 3,4-dihydroxyphenylacetate + FAD + H2O + H+ |
| Rhea:RHEA:54089 | 3,4-dihydroxyphenylacetate + NADH + O2 + H+ => 2,4,5-trihydroxyphenylacetate + NAD+ + H2O | |
| Rhea:RHEA:54090 | 2,4,5-trihydroxyphenylacetate + NAD+ + H2O => 3,4-dihydroxyphenylacetate + NADH + O2 + H+ | |
| Rhea:RHEA:54091 | 3,4-dihydroxyphenylacetate + NADH + O2 + H+ <=> 2,4,5-trihydroxyphenylacetate + NAD+ + H2O |
Taxonomy Source
- Aloe africana [ncbi taxid: 1080010]
- Aloe ferox [ncbi taxid: 117798]
- Aloe spicata [ncbi taxid: 992642]
- Aloe vera [ncbi taxid: 34199]
- Ania angustifolia [ncbi taxid: 1525812]
- Antonia ovata [ncbi taxid: 60095]
- Aria globosa [ncbi taxid: ]
- Artemisia baldshuanica [ncbi taxid: 1287601]
- Arthrospira platensis [ncbi taxid: ]
- Aspergillus flavus [ncbi taxid: 5059]
- Celastrus angulatus [ncbi taxid: 489977]
- Conyza welwitschii [ncbi taxid: ]
- Fusarium verticillioides [ncbi taxid: 117187]
- Homo sapiens [ncbi taxid: 9606]
- Olea europaea [ncbi taxid: 4146]
- Ophthalmoblapton macrophyllum [ncbi taxid: ]
- Phellinus tremulus [ncbi taxid: ]
- Pythium irregulare [ncbi taxid: ]
- Symphytum officinale [ncbi taxid: 278672]
- Taxus baccata [ncbi taxid: 25629]
- Tecoma radicans [ncbi taxid: ]
- Valeriana flaccidissima [ncbi taxid: 300905]
Pathway Synthetic
| pathway id | name |
|---|---|
| WikiPathways:WP4657 | 22q11.2 copy number variation syndrome |
| WikiPathways:WP4238 | Flavan-3-ol metabolic pathway |
| WikiPathways:WP3155 | Dopamine metabolism |
| WikiPathways:WP4220 | Neurotransmitter disorders |
| WikiPathways:WP2436 | Dopamine metabolism |
| PathBank:SMP0120674 | Alkaptonuria |
| PathBank:SMP0120782 | Dopamine beta-Hydroxylase Deficiency |
| PathBank:SMP0000190 | Hawkinsinuria |
| PathBank:SMP0087450 | Tyrosine Metabolism |
| PathBank:SMP0120729 | Tyrosinemia Type I |
| PathBank:SMP0120817 | Monoamine Oxidase-A Deficiency (MAO-A) |
| PathBank:SMP0120491 | Hawkinsinuria |
| PathBank:SMP0000169 | Alkaptonuria |
| PathBank:SMP0000429 | Disulfiram Action Pathway |
| PathBank:SMP0063684 | Tyrosine Metabolism |
| PathBank:SMP0120453 | Alkaptonuria |
| PathBank:SMP0120509 | Tyrosinemia Type I |
| PathBank:SMP0120598 | Monoamine Oxidase-A Deficiency (MAO-A) |
| PathBank:SMP0000218 | Tyrosinemia Type I |
| PathBank:SMP0000533 | Monoamine Oxidase-A Deficiency (MAO-A) |