3-Hydroxymandelic acid (BioDeep_00000017768)

 

Secondary id: BioDeep_00000398353, BioDeep_00000606742

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


2-Hydroxy-2-(3-hydroxyphenyl)acetic acid

化学式: C8H8O4 (168.0423)
中文名称: 3-羟基扁桃酸
谱图信息: 最多检出来源 Viridiplantae(plant) 19.56%

分子结构信息

SMILES: C1=CC(=CC(=C1)O)C(C(=O)O)O
InChI: InChI=1S/C8H8O4/c9-6-3-1-2-5(4-6)7(10)8(11)12/h1-4,7,9-10H,(H,11,12)

描述信息

3-Hydroxymandelic acid, also known as m-hydroxymandelate or MHMA, is a 2-hydroxy monocarboxylic acid. 3-Hydroxymandelic acid is the dehydroxylated (positions 2 and 3’) derivative of phenylacetic acid. It is a white crystalline solid that is soluble in water and polar organic solvents. It derives from a mandelic acid. Mandelic acid is a substrate or product of several biochemical processes called the mandelate pathway. Mandelate racemase interconverts the two enantiomers via a pathway that involves cleavage of the alpha-CH bond. Mandelate dehydrogenase is yet another enzyme on this pathway. Mandelate also arises from trans-cinnamate via phenylacetic acid, which is hydroxylated. Derivatives of mandelic acid, such as 3-hydroxymandelic acid, are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase.
m-hydroxymandelic acid or 3-hyrodxymandelic acid is a metabolic breakdown product of m-octopamine, m-synephrine (phenylephrine) and m-tyrosine. It is a naturally occuring catecholamine metabolite. Concentrations of m-hydroxymandelic acid can be elevated 20- to 30-fold in neuroblastoma patients. [HMDB]
D000890 - Anti-Infective Agents > D000892 - Anti-Infective Agents, Urinary > D008333 - Mandelic Acids
3-Hydroxymandelic Acid, a metabolite of Phenylephrine, Phenylephrine is a α-receptor agonist.

同义名列表

18 个代谢物同义名

2-Hydroxy-2-(3-hydroxyphenyl)acetic acid; 2-Hydroxy-2-(3-hydroxyphenyl)ethanoate; DL-Hydroxy(m-hydroxyphenyl)acetic acid; 2-Hydroxy-2-(3-hydroxyphenyl)acetate; m-Hydroxy-(6ci,7ci,8ci)mandelic acid; alpha,3-Dihydroxybenzeneacetic acid; Hydroxy(3-hydroxyphenyl)acetic acid; m-Hydroxy-(6ci,7ci,8ci)mandelate; 3-Hydroxyphenylglycolic acid; DL-3-Hydroxymandelic acid; Meta-hydroxymandelic acid; m-Hydroxymandelic acid; 3-Hydroxymandelic acid; DL-3-Hydroxymandelate; 3-Hydroxymandelate; m-Hydroxymandelate; MHMA; 3-Hydroxymandelic acid



数据库引用编号

11 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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)

11 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


文献列表

  • K Gumbhir, W D Mason. Determination of m-hydroxymandelic acid, m-hydroxyphenylglycol and their conjugates in human plasma using liquid chromatography with electrochemical detection. Journal of pharmaceutical and biomedical analysis. 1994 Jul; 12(7):943-9. doi: 10.1016/0731-7085(94)e0010-x. [PMID: 7981325]
  • J M Midgley, R Andrew, D G Watson, N MacDonald, J L Reid, D A Williams. Dichlorotetrafluoroacetone as a derivatisation reagent in the analysis of mandelic acids in human urine. Journal of chromatography. 1990 May; 527(2):259-65. doi: 10.1016/s0378-4347(00)82110-6. [PMID: 2387876]
  • M W Couch, D M Greer, C M Williams. Excretion of octopamine metabolites in neuroblastoma. Clinica chimica acta; international journal of clinical chemistry. 1986 Jul; 158(1):109-14. doi: 10.1016/0009-8981(86)90121-x. [PMID: 3091293]
  • J A Hoskins, A M Greenway. The metabolism of L-m-tyrosine: the use of a putative precursor to investigate the increased production of m-hydroxymandelic acid in phenylketonuria. Clinica chimica acta; international journal of clinical chemistry. 1983 Jun; 130(3):329-38. doi: 10.1016/0009-8981(83)90307-8. [PMID: 6872265]
  • K E Ibrahim, J M Midgley, J R Crowley, C M Williams. The mammalian metabolism of R-(-)-m-synephrine. The Journal of pharmacy and pharmacology. 1983 Mar; 35(3):144-7. doi: 10.1111/j.2042-7158.1983.tb04293.x. [PMID: 6132969]
  • J R Crowley, M W Couch, C M Williams, M I James, K E Ibrahim, J M Midgley. Identification and quantitative determination of m-hydroxyphenylglycol in mammalian urine. Biomedical mass spectrometry. 1982 Apr; 9(4):146-52. doi: 10.1002/bms.1200090404. [PMID: 7093439]
  • B A Davis, A A Boulton. Excretion of m-hydroxymandelic acid in human urine. Journal of chromatography. 1981 Feb; 222(2):271-5. doi: 10.1016/s0378-4347(00)81060-9. [PMID: 6788786]
  • J R Crowley, M W Couch, C M Williams, R M Threatte, M J Fregly. Normal excretion of m-hydroxymandelic acid in hypertensive patients. Clinica chimica acta; international journal of clinical chemistry. 1981 Jan; 109(2):125-31. doi: 10.1016/0009-8981(81)90326-0. [PMID: 7471493]