(3,4-dihydroxyphenyl)acetic acid (CHEBI:41941)

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CHEBI:41941 - (3,4-dihydroxyphenyl)acetic acid

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ChEBI Name	(3,4-dihydroxyphenyl)acetic acid

ChEBI ID	CHEBI:41941

Definition	A dihydroxyphenylacetic acid having the two hydroxy substituents located at the 3- and 4-positions. It is a metabolite of dopamine.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:1386, CHEBI:41936

Supplier Information	No supplier information found for this compound.

Download	Molfile XML SDF

more structures >>

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0.8904 -0.2008 0.5427 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7147 0.6284 -0.2428 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.5164 -0.0626 0.5227 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.0860 0.9302 -0.3065 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.2711 1.7656 -1.0901 C 0 0 0 0 0 0 0 0 0 0 0 0

1.1299 1.6187 -1.0605 C 0 0 0 0 0 0 0 0 0 0 0 0

-1.7146 -2.1536 0.5551 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.8753 -2.4285 0.2909 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.8520 -2.9187 0.1352 O 0 0 0 0 0 0 0 0 0 0 0 0

-1.3742 -0.9731 1.3215 C 0 0 0 0 0 0 0 0 0 0 0 0

1.8392 2.3759 -1.7692 O 0 0 0 0 0 0 0 0 0 0 0 0

2.9609 0.4643 -0.2022 O 0 0 0 0 0 0 0 0 0 0 0 0

1.3235 -0.9216 1.1280 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1011 1.0503 -0.3534 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7074 2.4767 -1.6826 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0015 -2.7532 0.2793 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2716 -0.4446 1.6580 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8673 -1.2841 2.2392 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4649 2.9925 -2.2746 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3122 -0.1619 0.3093 H 0 0 0 0 0 0 0 0 0 0 0 0

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4 14 1 0 0 0 0

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10 17 1 0 0 0 0

10 18 1 0 0 0 0

11 19 1 0 0 0 0

12 20 1 0 0 0 0

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Wikipedia	License
3,4-Dihydroxyphenylacetic acid (DOPAC) is a metabolite of the neurotransmitter dopamine. Dopamine can be metabolized into one of three substances. One such substance is DOPAC. Another is 3-methoxytyramine (3-MT). Both of these substances are degraded to form homovanillic acid (HVA). Both degradations involve the enzymes monoamine oxidase (MAO) and catechol-O-methyl transferase (COMT), albeit in reverse order: MAO catalyzes dopamine to DOPAC, and COMT catalyzes DOPAC to HVA; whereas COMT catalyzes dopamine to 3-MT and MAO catalyzes 3-MT to HVA. The third metabolic end-product of dopamine is norepinephrine (noradrenaline). It can also be found in the bark of Eucalyptus globulus. This product has been synthesized (52% yield) from 4-hydroxyphenylacetic acid via aerobic biotransformation using whole cell cultures of Arthrobacter protophormiae.
Read full article at Wikipedia

Formula

C8H8O4

Net Charge

Average Mass

168.14672

Monoisotopic Mass

168.04226

InChI

InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)

InChIKey

CFFZDZCDUFSOFZ-UHFFFAOYSA-N

SMILES

OC(=O)Cc1ccc(O)c(O)c1

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	(3,4-dihydroxyphenyl)acetic acid (CHEBI:41941) has functional parent phenylacetic acid (CHEBI:30745) (3,4-dihydroxyphenyl)acetic acid (CHEBI:41941) has role human metabolite (CHEBI:77746) (3,4-dihydroxyphenyl)acetic acid (CHEBI:41941) is a catechols (CHEBI:33566) (3,4-dihydroxyphenyl)acetic acid (CHEBI:41941) is a dihydroxyphenylacetic acid (CHEBI:61409) (3,4-dihydroxyphenyl)acetic acid (CHEBI:41941) is conjugate acid of (3,4-dihydroxyphenyl)acetate (CHEBI:17612)

Incoming	homovanillic acid (CHEBI:545959) has functional parent (3,4-dihydroxyphenyl)acetic acid (CHEBI:41941) isohomovanillic acid (CHEBI:70818) has functional parent (3,4-dihydroxyphenyl)acetic acid (CHEBI:41941) (3,4-dihydroxyphenyl)acetate (CHEBI:17612) is conjugate base of (3,4-dihydroxyphenyl)acetic acid (CHEBI:41941)

IUPAC Name

(3,4-dihydroxyphenyl)acetic acid

Synonyms	Sources
2-(3,4-DIHYDROXYPHENYL)ACETIC ACID	PDBeChem
3,4-Dihydroxyphenyl acetic acid	KEGG COMPOUND
3,4-Dihydroxyphenylacetic acid	KEGG COMPOUND
dopacetic acid	NIST Chemistry WebBook
homoprotocatechuic acid	NIST Chemistry WebBook

Manual Xrefs	Databases
C01161	KEGG COMPOUND
DB01702	DrugBank
DHY	PDBeChem
DOPAC	Wikipedia
HMDB0001336	HMDB
View more database links

Registry Numbers	Types	Sources
102-32-9	CAS Registry Number	NIST Chemistry WebBook
102-32-9	CAS Registry Number	ChemIDplus
2211017	Beilstein Registry Number	Beilstein
2211017	Reaxys Registry Number	Reaxys
874810	Gmelin Registry Number	Gmelin

Citations

Lee JJ, Chang CK, Liu IM, Chi TC, Yu HJ, Cheng JT (2001)
Changes in endogenous monoamines in aged rats.
Clinical and experimental pharmacology & physiology 28, 285-289 [PubMed:11251641]
[show Abstract]

Eldrup E, Clausen N, Scherling B, Schmiegelow K (2001)
Evaluation of plasma 3,4-dihydroxyphenylacetic acid (DOPAC) and plasma 3,4-dihydroxyphenylalanine (DOPA) as tumor markers in children with neuroblastoma.
Scandinavian journal of clinical and laboratory investigation 61, 479-490 [PubMed:11681538]
[show Abstract]

Ferreira A, Bettencourt P, Pimenta J, Friões F, Pestana M, Soares-da-Silva P, Cerqueira-Gomes M (2002)
The renal dopaminergic system, neurohumoral activation, and sodium handling in heart failure.
American heart journal 143, 391-397 [PubMed:11868042]
[show Abstract]

Background

Dopamine of renal origin exerts natriuretic and diuretic actions by activating specific receptors located in the renal proximal tubular epithelial cells. Heart failure (HF) is accompanied by activation of several neurohumoral systems. The interaction of these systems with the renal dopaminergic system and its effect on sodium handling in HF are not clarified.

Methods and results

We studied 13 patients with decompensated New York Heart Association class III/IV HF and 17 sex- and age-matched patients with mild to moderate stable class I/II HF. We measured plasma catecholamines, aldosterone, type B natriuretic peptide (BNP), sodium, creatinine (UCr), and 24-hour urinary excretion of sodium, UCr, levo-3,4-dihydroxyphenylalanine (L-DOPA), 3-o -methyldopa, dopamine and its metabolites, 3,4-dihydroxyphenylacetic acid and homovallinic acid, and norepinephrine. All patients had HF of ischemic etiology. No statistically significant differences were found between the groups with respect to urine volume (1.79 +/- 0.23 L x d(-1) vs 2.20 +/- 0.18 L x d(-1), P =.18) and urinary sodium (161.3 +/- 27.5 mmol x d(-1) vs 232.9 +/- 28.8 mmol x d(-1), P =.12). Urinary L-DOPA was significantly lower in patients with decompensated class III/IV HF than in the other group (79.0 +/- 13.8 nmol x g UCr(-1) vs 108.4 +/- 10.3 nmol x g UCr(-1), P =.04). Urinary dopamine showed a nonstatistically significant trend to be slightly higher (1294.3 +/- 188.5 nmol x g UCr(-1) vs 953.2 +/- 107.4 nmol x g UCr(-1), P =.14). Consequently, urinary dopamine/L-DOPA ratios were markedly higher in patients with decompensated class III/IV HF than in the other patients (20.6 +/- 3.4 vs 9.0 +/- 0.9, P <.001). Plasma L-DOPA (38.1 +/- 4.4 pmol x mL(-1) vs 40.0 +/- 3.0 pmol x mL(-1), P =.48), dopamine (37.0 +/- 6.3 pmol x mL(-1) vs 41.1 +/- 2.6 pmol x mL(-1), P =.53), 3,4-dihydroxyphenylacetic acid (51.7 +/- 11.7 pmol x mL(-1) vs 56.5 +/- 5.4 pmol x mL(-1), P =.09), and norepinephrine (9.5 +/- 2.4 pmol x mL(-1) vs 5.6 +/- 1.0 pmol x mL(-1), P =.12) did not differ between groups. Plasma aldosterone (180.2 +/- 28.0 pg x mL(-1) vs 69.9 +/- 13.3 pg x mL(-1), P <.001) and BNP (677.5 +/- 133.9 pg x mL(-1) vs 389.4 +/- 88.4 pg x mL(-1), P <.04) levels were higher in the decompensated class III/IV HF group than in the other group, whereas serum sodium was lower (137.3 +/- 1.2 mmol x L(-1) vs 143.2 +/- 1.0 mmol x L(-1), P =.001).

Conclusions

These results suggest that, in patients with HF, the increased renal utilization of L-DOPA may constitute a compensatory mechanism, activated in response to stimuli leading to sodium reabsorption.

Last Modified

09 December 2024

CHEBI:41941 - (3,4-dihydroxyphenyl)acetic acid

Background

Methods and results

Conclusions

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