Homovanillic acid (HVA) (BioDeep_00000017338)

 

Secondary id: BioDeep_00000000455, BioDeep_00000402954

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


4-Hydroxy-3-methoxyphenylacetic acid;Vanillacetic acid;2-(4-Hydroxy-3-methoxyphenyl)acetic acid

化学式: C9H10O4 (182.0579)
中文名称: 高香草酸(HVA), 4-羟基-3-甲氧基苯乙酸, 高香草酸
谱图信息: 最多检出来源 Viridiplantae(plant) 10.57%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Homovanillic acid (HVA). BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/homovanillic_acid_(hva) (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000017338). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c1c(c(cc(c1)CC(=O)O)OC)O
InChI: InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)

描述信息

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).
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 human metabolite and a mouse 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.
Homovanillic acid is a natural product found in Aloe africana, Ginkgo biloba, and other organisms with data available.
Homovanillic Acid is a monocarboxylic acid that is a catecholamine metabolite. Homovanillic acid may be used a marker for metabolic stress, tobacco usage or the presence of a catecholamine secreting tumor, such as neuroblastoma or pheochromocytoma.
Homovanillic acid is a metabolite found in or produced by Saccharomyces cerevisiae.
A 3-O-methyl ETHER of (3,4-dihydroxyphenyl)acetic acid.
See also: Ipomoea aquatica leaf (part of).
Homovanillic acid is a major catecholamine metabolite. 3-Methoxy-4-hydroxyphenylacetic acid is found in beer, olive, and avocado.
A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.
Homovanillic acid is a dopamine metabolite found to be associated with aromatic L-amino acid decarboxylase deficiency, celiac disease, growth hormone deficiency, and sepiapterin reductase deficiency.
Homovanillic acid is a dopamine metabolite found to be associated with aromatic L-amino acid decarboxylase deficiency, celiac disease, growth hormone deficiency, and sepiapterin reductase deficiency.

同义名列表

60 个代谢物同义名

4-Hydroxy-3-methoxyphenylacetic acid;Vanillacetic acid;2-(4-Hydroxy-3-methoxyphenyl)acetic acid; 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); 4-HYDROXY-3-METHOXYPHENYLACETIC ACID (2,5,6-D3,ALPHA,ALPHA-D2); 4-Hydroxy-3-methoxyphenylacetic acid Homovanillic acid; Acetic acid, (4-hydroxy-3-methoxyphenyl)- (8CI); 2-(3-Methoxy-4-Oxidanyl-Phenyl)ethanoic Acid; 4-HYDROXY-3-METHOXYPHENYLACETIC-2,2-D2 ACID; Acetic acid, (4-hydroxy-3-methoxyphenyl)-; (4-hydroxy-3-methyoxy-phenyl)-acetic acid; (4-Hydroxy-3-methoxy-phenyl)-acetic acid; 2-(4-Hydroxy-3-methoxyphenyl)acetic acid; Benzeneacetic acid, 4-hydroxy-3-methoxy-; 4-HYDROXY-3-METHOXY-.ALPHA.-TOLUIC ACID; Homovanillic acid, Fluorimetric reagent; (4-HYDROXY-3-METHOXYPHENYL)ACETIC ACID; 4-hydroxy-3-methoxy-benzeneacetic acid; 3’-methoxy-4’-hydroxyphenylacetic acid; Homovanillic acid, analytical standard; 4-hydroxy-3-methoxy-phenylacetic acid; Acid, 3-Methoxy-4-Hydroxyphenylacetic; 4-HYDROXY-3-METHOXY-alpha-TOLUIC ACID; 4-hydroxy-3-methoxyphenyl-acetic acid; Acid, 4-Hydroxy-3-Methoxyphenylacetic; 4-Hydroxy-3-methoxy-phenylacetic acid; 4-Hydroxy-3-methoxybenzeneacetic acid; 3-methoxy-4-hydroxy-phenylacetic acid; 3 Methoxy 4 Hydroxyphenylacetic Acid; 4-hydroxy 3-methoxyphenylacetic acid; 3-Methoxy-4-hydroxyphenylacetic acid; 4-Hydroxy-3-methoxyphenylacetic acid; 4 Hydroxy 3 Methoxyphenylacetic Acid; 4-hydroxy-3-methoxyphenyacetic acid; (4-Hydroxy-3-methoxyphenyl)acetate; 4-Hydroxy-3-methoxybenzeneacetate; 3-Methoxy-4-hydroxyphenylacetate; QRMZSPFSDQBLIX-UHFFFAOYSA-; Homovanillic acid, 98\\%; HOMOVANILLIC ACID [MI]; Homovanillic acid; HVA; Homovanillinic acid; Acid, Homovanillic; Vanillacetic acid; homovanillic-acid; Homovanillic Acid; Homovaniuic acid; Vanilacetic acid; Homovanilic acid; UNII-X77S6GMS36; Oprea1_505423; Homovanillate; Vanillacetate; Lopac0_000632; Vanilacetate; Tox21_500632; Homovanilate; X77S6GMS36; YTX; HVA; Homovanillic acid; Homovanillate



数据库引用编号

23 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(6)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

9 个相关的物种来源信息

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。

亚细胞结构定位 关联基因列表
Cytoplasm 11 BDNF, CAT, DBH, DDC, ENO2, GFAP, HTT, POMC, PRL, SLC6A3, TH
Peripheral membrane protein 1 ACHE
Endosome membrane 1 HTT
Mitochondrion membrane 1 MAOA
Nucleus 4 ACHE, HTT, PRL, TH
autophagosome 1 HTT
cytosol 8 CAT, COMT, DDC, ENO2, GFAP, HTT, MAOA, TH
dendrite 6 BDNF, COMT, DRD2, HTT, MAOB, TH
nucleoplasm 2 HTT, PRL
RNA polymerase II transcription regulator complex 1 PRL
Cell membrane 6 ACHE, COMT, DRD2, ENO2, HTT, SLC6A3
Cytoplasmic side 2 MAOA, MAOB
Cell projection, axon 2 SLC6A3, TH
Multi-pass membrane protein 4 DRD2, HTT, SLC22A8, SLC6A3
Golgi apparatus membrane 1 DRD2
Synapse 6 ACHE, COMT, CRH, DBH, DRD2, HTT
cell surface 2 ACHE, SLC6A3
glutamatergic synapse 1 DRD2
Golgi apparatus 2 ACHE, HTT
Golgi membrane 2 DRD2, INS
neuromuscular junction 1 ACHE
neuronal cell body 2 MAOB, SLC6A3
presynaptic membrane 3 DRD2, HTT, SLC6A3
smooth endoplasmic reticulum 1 TH
synaptic vesicle 2 BDNF, TH
acrosomal vesicle 1 DRD2
plasma membrane 7 ACHE, COMT, DRD2, ENO2, HTT, SLC22A8, SLC6A3
synaptic vesicle membrane 1 DRD2
terminal bouton 1 TH
Membrane 8 ACHE, BDNF, CAT, COMT, DBH, ENO2, MAOA, SLC6A3
apical plasma membrane 1 SLC22A8
axon 6 BDNF, COMT, DRD2, HTT, SLC6A3, TH
basolateral plasma membrane 1 SLC22A8
extracellular exosome 5 CAT, COMT, DDC, ENO2, SLC22A8
endoplasmic reticulum 2 DBH, HTT
extracellular space 9 ACHE, BDNF, CRH, DBH, ENO2, IL6, INS, POMC, PRL
perinuclear region of cytoplasm 4 ACHE, BDNF, HTT, TH
mitochondrion 4 CAT, MAOA, MAOB, TH
protein-containing complex 2 CAT, HTT
intracellular membrane-bounded organelle 3 CAT, COMT, DBH
Secreted 8 ACHE, BDNF, CRH, DBH, IL6, INS, POMC, PRL
extracellular region 9 ACHE, BDNF, CAT, CRH, DBH, IL6, INS, POMC, PRL
cytoplasmic side of plasma membrane 1 TH
Mitochondrion outer membrane 2 MAOA, MAOB
Single-pass membrane protein 1 MAOA
mitochondrial outer membrane 2 MAOA, MAOB
astrocyte end-foot 1 GFAP
neuronal cell body membrane 1 SLC6A3
mitochondrial matrix 1 CAT
Extracellular side 2 ACHE, COMT
centriolar satellite 1 DBH
ciliary membrane 1 DRD2
photoreceptor inner segment 1 ENO2
varicosity 1 CRH
dendritic spine 1 DRD2
neuronal dense core vesicle lumen 1 CRH
perikaryon 4 CRH, DRD2, ENO2, TH
cytoplasmic vesicle 1 TH
Melanosome membrane 1 TH
Early endosome 1 HTT
Single-pass type II membrane protein 2 COMT, DBH
postsynaptic membrane 3 DRD2, HTT, SLC6A3
Cytoplasm, perinuclear region 1 TH
Membrane raft 2 HTT, SLC6A3
Cell junction, focal adhesion 1 HTT
focal adhesion 2 CAT, HTT
GABA-ergic synapse 1 DRD2
flotillin complex 1 SLC6A3
Peroxisome 1 CAT
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
secretory granule 1 POMC
intermediate filament 1 GFAP
lateral plasma membrane 2 DRD2, SLC22A8
Late endosome 1 HTT
Cell projection, neuron projection 2 HTT, SLC6A3
neuron projection 3 HTT, SLC6A3, TH
cilium 1 DRD2
chromatin 1 PRL
cell projection 1 GFAP
centriole 1 HTT
non-motile cilium 1 DRD2
Basolateral cell membrane 1 SLC22A8
Lipid-anchor, GPI-anchor 1 ACHE
sperm flagellum 1 DRD2
Endomembrane system 1 HTT
endosome lumen 2 INS, PRL
Cytoplasmic vesicle membrane 1 HTT
cell body 1 GFAP
side of membrane 1 ACHE
intermediate filament cytoskeleton 1 GFAP
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 4 CAT, DBH, INS, POMC
secretory granule membrane 1 DBH
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 BDNF, IL6, INS
axon terminus 2 DRD2, SLC6A3
endocytic vesicle 1 DRD2
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
mitochondrial envelope 1 MAOB
Single-pass type IV membrane protein 2 MAOA, MAOB
synaptic cleft 1 ACHE
dopaminergic synapse 2 DRD2, SLC6A3
Cytoplasmic vesicle, secretory vesicle membrane 1 DBH
postsynaptic cytosol 1 HTT
presynaptic cytosol 1 HTT
cytoplasmic side of lysosomal membrane 1 GFAP
Cytoplasmic vesicle, secretory vesicle, chromaffin granule lumen 1 DBH
chromaffin granule lumen 1 DBH
transport vesicle membrane 1 DBH
catalase complex 1 CAT
inclusion body 1 HTT
interleukin-6 receptor complex 1 IL6
phosphopyruvate hydratase complex 1 ENO2
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
[Soluble dopamine beta-hydroxylase]: Cytoplasmic vesicle, secretory vesicle lumen 1 DBH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule membrane 1 DBH
chromaffin granule membrane 1 DBH
G protein-coupled receptor complex 1 DRD2
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
[Isoform H]: Cell membrane 1 ACHE
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
serotonergic synapse 1 HTT
[Huntingtin]: Cytoplasm 1 HTT
[Huntingtin, myristoylated N-terminal fragment]: Cytoplasmic vesicle, autophagosome 1 HTT


文献列表

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