3,4-Dihydroxyphenylglycol (BioDeep_00000001226)
Secondary id: BioDeep_00000405241
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019
Metabolite Card
Formula: C8H10O4 (170.057906)
Chinese Names: 3,4-二羟基苯基乙二醇
Spectrum Hits:
Top Source Homo sapiens(blood) 8.08%
Molecular Structure
SMILES: C1=CC(=C(C=C1C(CO)O)O)O
InChI: InChI=1S/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2
Description
3,4-Dihydroxyphenylglycol, also known as DHPG or DOPEG, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxyphenylglycol is an extremely weak basic (essentially neutral) compound. 3,4-Dihydroxyphenylglycol exists in all living organisms, ranging from bacteria to plants to humans. It is a potent antioxidant (PMID: 30007612). In mammals, 3,4-Dihydroxyphenylglycol is the primary metabolite of norepinephrine and is generated through the action of the enzyme monoamine oxidase (MAO). DHPG is then further metabolized by the enzyme Catechol-O-methyltransferase (COMT) to 3-methoxy-4-hydroxyphenylglycol (MHPG). Within humans, 3,4-dihydroxyphenylglycol participates in a number of enzymatic reactions. In particular, 3,4-dihydroxyphenylglycol can be biosynthesized from 3,4-dihydroxymandelaldehyde; which is mediated by the enzyme alcohol dehydrogenase 1A. In addition, 3,4-dihydroxyphenylglycol and guaiacol can be converted into vanylglycol and pyrocatechol through its interaction with the enzyme catechol O-methyltransferase. Outside of the human body, 3,4-dihydroxyphenylglycol is found, on average, in the highest concentration in olives. High levels of DHPG (up to 368 mg/kg of dry weight) have been found in the pulp of natural black olives. This could make 3,4-dihydroxyphenylglycol a potential biomarker for the consumption of olives and olive oil. 3,4-Dihydroxyphenylglycol has been linked to Menkes disease (PMID: 19234788). DHPG level are lower in Menkes patients (3.57 ± 0.40 nM) than healthy infants 8.91 ± 0.77 nM). Menkes disease (also called “kinky hair disease”) is an X-linked recessive neurodevelopmental disorder caused by defects in a gene that encodes a copper-transporting ATPase (ATP7A). Affected infants typically appear healthy at birth and show normal neurodevelopment for 2-3 months. Subsequently there is loss of milestones (e.g., smiling, visual tracking, head control) and death in late infancy or childhood (PMID: 19234788).
3,4-Dihydroxyphenylglycol (DOPEG) is a normal norepinephrine metabolite present in CSF, plasma and urine in humans (PMID 6875564). In healthy individuals there is a tendency for free DOPEG to increase and for conjugated DOPEG to decrease with age; plasmatic DOPEG levels are significantly lower in depressed patients as compared to healthy controls (PMID 6671452). DL-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol is found in olive.
4-(1,2-Dihydroxyethyl)benzene-1,2-diol, a normal norepinephrine metabolite, is found to be associated with Menkes syndrome.
Synonyms
24 synonym names
DL-α,β,3,4-Tetrahydroxyphenethyl alcohol; Dihydroxyphenylethylene glycol, (+-)-isomer; Dihydroxyphenylethylene glycol, (S)-isomer; DL-1-(3,4-Dihydroxyphenyl)-1,2-ethanediol; DL-β,3,4-Trihydroxyphenethyl alcohol; 2-Hydroxy-2-(3,4-dihydroxy)phenylethanol; 4-(1,2-Dihydroxyethyl)-1,2-benzenediol; 1-(3,4-Dihydroxyphenyl)-1,2-ethanediol; 4-(1,2-dihydroxyethyl)benzene-1,2-diol; beta,3,4-Trihydroxy phenethyl alcohol; (3,4-Dihydroxyphenyl)ethylene glycol; b,3,4-Trihydroxy phenethyl alcohol; Β,3,4-trihydroxy phenethyl alcohol; 3,4-Dihydroxyphenylethyleneglycol; 3,4-Dihydroxyphenylethyl glycol; Dihydroxyphenylethylene glycol; 3,4-Dihydroxyphenethyl glycol; DL-3,4-Dihydroxyphenyl glycol; DL-3,4-Dihydroxyphenylglycol; 3,4-Dihydroxyphenylglycol; Dihydroxyphenylglycine; DOPEG; DHPG; 3,4-Dihydroxyphenylglycol
Cross Reference
17 cross reference id
- ChEBI: CHEBI:1387
- KEGG: C05576
- PubChem: 91528
- HMDB: HMDB0000318
- Metlin: METLIN3788
- MetaCyc: CPD-11878
- foodb: FDB020084
- chemspider: 82648
- CAS: 28822-73-3
- CAS: 3343-19-9
- PMhub: MS000000166
- PubChem: 7902
- 3DMET: B05073
- NIKKAJI: J45.947J
- RefMet: 3,4-Dihydroxyphenylglycol
- medchemexpress: HY-W010066
- BioNovoGene_Lab2019: BioNovoGene_Lab2019-353
Classification Terms
Related Pathways
Reactome(0)
BioCyc(0)
PlantCyc(0)
Biological Process
27 related biological process reactions.
Reactome(0)
BioCyc(1)
- noradrenaline and adrenaline degradation:
H2O + O2 + noradrenaline ⟶ 3,4-dihydroxyphenylglycolaldehyde + H+ + ammonia + hydrogen peroxide
WikiPathways(0)
Plant Reactome(0)
INOH(2)
- Tyrosine metabolism ( Tyrosine metabolism ):
4-Hydroxy-phenyl-acetaldehyde + H2O + NAD+ ⟶ 4-Hydroxy-phenyl-acetic acid + NADH
- NAD+ + 3,4-Dihydroxy-phenyl-ethyleneglycol = NADH + 3,4-Dihydroxy-mandelaldehyde ( Tyrosine metabolism ):
3,4-Dihydroxy-phenyl-ethyleneglycol + NAD+ ⟶ 3,4-Dihydroxy-mandelaldehyde + NADH
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(24)
- Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Alkaptonuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Hawkinsinuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosinemia Type I:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Disulfiram Action Pathway:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosinemia, Transient, of the Newborn:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Dopamine beta-Hydroxylase Deficiency:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Monoamine Oxidase-A Deficiency (MAO-A):
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Alkaptonuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Hawkinsinuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosinemia Type I:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosinemia, Transient, of the Newborn:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Dopamine beta-Hydroxylase Deficiency:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Monoamine Oxidase-A Deficiency (MAO-A):
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosine Metabolism:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Alkaptonuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Hawkinsinuria:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosinemia Type I:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Tyrosinemia, Transient, of the Newborn:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Dopamine beta-Hydroxylase Deficiency:
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
- Monoamine Oxidase-A Deficiency (MAO-A):
Homovanillin + NADP + Water ⟶ NADPH + p-Hydroxyphenylacetic acid
PharmGKB(0)
3 organism taxonomy source information
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1007/S11306-016-1051-4
- 4146 - Olea europaea:
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有:
- PubMed: 来源于PubMed文献库中的文献信息,我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表,这个列表按照代谢物同时出现的文献数量降序排序,取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘,得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序,取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中,存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称,可以跳转到相关代谢物的信息页面。
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