3,4-Dihydroxymandelic acid (BioDeep_00000003079)

 

Secondary id: BioDeep_00000400356, BioDeep_00000413325

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid

化学式: C8H8O5 (184.0372)
中文名称: DL-3,4-二羟基扁桃酸, DL-3,4-二羟基杏仁酸, 3,4-二羟苯乙酸, 3,4-二羟基扁桃酸
谱图信息: 最多检出来源 Homo sapiens(blood) 9.82%

分子结构信息

SMILES: C1=CC(=C(C=C1C(C(=O)O)O)O)O
InChI: InChI=1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)

描述信息

3,4-Dihydroxymandelic acid, also known as DOMA or 3,4-dihydroxyphenylglycolate, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-Dihydroxymandelic acid exists in all living organisms, ranging from bacteria to humans. Within humans, 3,4-dihydroxymandelic acid participates in a number of enzymatic reactions. In particular, 3,4-dihydroxymandelic acid can be biosynthesized from 3,4-dihydroxymandelaldehyde through its interaction with the enzyme aldehyde dehydrogenase, dimeric nadp-preferring. In addition, 3,4-dihydroxymandelic acid and guaiacol can be converted into vanillylmandelic acid and pyrocatechol through the action of the enzyme catechol O-methyltransferase. In humans, 3,4-dihydroxymandelic acid is involved in the metabolic disorder called tyrosinemia type I. Outside of the human body, 3,4-Dihydroxymandelic acid has been detected, but not quantified in several different foods, such as yellow wax beans, soy beans, pomegranates, cucurbita (gourd), and daikon radish.
3,4-dihydroxymandelic acid, also known as 3,4-dihydroxyphenylglycolate or (3,4-dihydroxyphenyl)(hydroxy)acetic acid, is a member of the class of compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3,4-dihydroxymandelic acid is soluble (in water) and a moderately acidic compound (based on its pKa). 3,4-dihydroxymandelic acid can be found in a number of food items such as lime, pitanga, sapodilla, and persimmon, which makes 3,4-dihydroxymandelic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxymandelic acid can be found primarily in blood and urine, as well as in human nerve cells tissue. In humans, 3,4-dihydroxymandelic acid is involved in a couple of metabolic pathways, which include disulfiram action pathway and tyrosine metabolism. 3,4-dihydroxymandelic acid is also involved in several metabolic disorders, some of which include hawkinsinuria, alkaptonuria, dopamine beta-hydroxylase deficiency, and tyrosinemia, transient, of the newborn.
D000890 - Anti-Infective Agents > D000892 - Anti-Infective Agents, Urinary > D008333 - Mandelic Acids
Acquisition and generation of the data is financially supported in part by CREST/JST.
KEIO_ID D066
3,4-Dihydroxymandelic acid is a metabolite of norepinephrine.

同义名列表

22 个代谢物同义名

2-(3,4-dihydroxyphenyl)-2-hydroxyacetic acid; 3,4-Dihydroxymandelic acid, monosodium salt; (3,4-Dihydroxyphenyl)(hydroxy)acetic acid; 3,4-Dihydroxymandelic acid, (+-)-isomer; 3,4-Dihydroxymandelic acid, (S)-isomer; (3,4-Dihydroxyphenyl)(hydroxy)acetate; 3,4-Dihydroxymandelic acid, ion(1-); 3,4-Dihydroxyphenylglycolic acid; dl-3,4-dihydroxymandelic acid; 3,4-Dihydroxyphenylglycolate; 3,4 Dihydroxymandelic acid; 3,4-Dihydroxymandelic acid; 3,4 Dihydroxymandelate; Dihydroxymandelic acid; 3,4-Dihydroxymandelate; Dihydroxymandelate; DOMA; DHMA; 3,4-Dihydroxymandelic acid; 3,4-Dihydroxymandelate; 3,4-Dihydroxymandelic acid; 3,4-Dihydroxymandelic acid



数据库引用编号

27 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

27 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(24)

PharmGKB(0)

2 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 10 ADA, AKR1B1, ANG, DBH, GNAQ, GRP, PLA2G12A, PRKAA2, PTP4A2, TYR
Peripheral membrane protein 1 ADA
Mitochondrion membrane 1 MAOA
Nucleus 4 ANG, GNAQ, PRKAA2, PTP4A2
cytosol 10 ADA, AKR1A1, AKR1B1, ANG, COMT, MAOA, PRKAA2, PTP4A2, SST, SSTR2
dendrite 2 COMT, PRKAA2
nucleoplasm 2 AKR1B1, PRKAA2
Cell membrane 5 ADA, ADRB3, COMT, GNAQ, TSHR
Lipid-anchor 1 GNAQ
Cytoplasmic side 1 MAOA
Multi-pass membrane protein 2 ADRB3, TSHR
Synapse 4 AKR1A1, COMT, DBH, GNAQ
cell junction 1 ADA
cell surface 3 ADA, ADIPOQ, TSHR
Golgi apparatus 2 GNAQ, PRKAA2
growth cone 1 ANG
lysosomal membrane 2 CP, GNAQ
neuronal cell body 3 ANG, PRKAA2, SST
Cytoplasm, cytosol 1 AKR1A1
Lysosome 2 ADA, TYR
plasma membrane 8 ADA, ADRB3, COMT, CP, GNAQ, PTP4A2, SSTR2, TSHR
Membrane 7 ADA, COMT, DBH, GNAQ, MAOA, PRKAA2, TSHR
apical plasma membrane 1 AKR1A1
axon 2 COMT, PRKAA2
basolateral plasma membrane 1 TSHR
extracellular exosome 5 AKR1A1, AKR1B1, COMT, CP, GNAQ
endoplasmic reticulum 2 ADIPOQ, DBH
extracellular space 9 ADIPOQ, AKR1A1, AKR1B1, ANG, CP, DBH, GAST, GRP, SST
perinuclear region of cytoplasm 1 TYR
mitochondrion 2 AKR1B1, MAOA
intracellular membrane-bounded organelle 3 COMT, DBH, TYR
Single-pass type I membrane protein 1 TYR
Secreted 8 ADIPOQ, ANG, CP, DBH, GAST, GRP, PLA2G12A, SST
extracellular region 8 ADIPOQ, ANG, CP, DBH, GAST, GRP, PLA2G12A, SST
Mitochondrion outer membrane 1 MAOA
Single-pass membrane protein 1 MAOA
mitochondrial outer membrane 1 MAOA
Extracellular side 2 ADA, COMT
Cytoplasmic vesicle lumen 1 ADA
anchoring junction 1 ADA
centriolar satellite 1 DBH
photoreceptor outer segment 1 GNAQ
Nucleus membrane 1 GNAQ
nuclear membrane 1 GNAQ
external side of plasma membrane 1 ADA
Secreted, extracellular space, extracellular matrix 1 GRP
actin cytoskeleton 1 ANG
nucleolus 1 ANG
Melanosome membrane 1 TYR
Early endosome 1 PTP4A2
Golgi-associated vesicle 1 TYR
Single-pass type II membrane protein 2 COMT, DBH
Apical cell membrane 1 AKR1A1
GABA-ergic synapse 1 SST
extracellular matrix 1 GRP
basement membrane 1 ANG
collagen trimer 1 ADIPOQ
collagen-containing extracellular matrix 1 ADIPOQ
lateral plasma membrane 1 TSHR
nuclear speck 1 PRKAA2
receptor complex 2 ADRB3, TSHR
Cell projection, neuron projection 1 GRP
neuron projection 2 GRP, SSTR2
Chromosome 1 ANG
Nucleus, nucleolus 1 ANG
blood microparticle 1 CP
Basolateral cell membrane 1 TSHR
heterotrimeric G-protein complex 1 GNAQ
Melanosome 1 TYR
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 2 ANG, PRKAA2
secretory granule lumen 2 DBH, GRP
secretory granule membrane 1 DBH
endoplasmic reticulum lumen 1 CP
endocytic vesicle 1 ANG
neuronal dense core vesicle 2 GRP, SST
Single-pass type IV membrane protein 1 MAOA
Cytoplasmic vesicle, secretory vesicle membrane 1 DBH
nucleotide-activated protein kinase complex 1 PRKAA2
Cytoplasmic vesicle, secretory vesicle, chromaffin granule lumen 1 DBH
chromaffin granule lumen 1 DBH
transport vesicle membrane 1 DBH
angiogenin-PRI complex 1 ANG
Cytoplasmic vesicle, secretory vesicle lumen 1 GRP
[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
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT


文献列表

  • Nitesh Sule, Sasi Pasupuleti, Nandita Kohli, Rani Menon, Lawrence J Dangott, Michael D Manson, Arul Jayaraman. The Norepinephrine Metabolite 3,4-Dihydroxymandelic Acid Is Produced by the Commensal Microbiota and Promotes Chemotaxis and Virulence Gene Expression in Enterohemorrhagic Escherichia coli. Infection and immunity. 2017 10; 85(10):. doi: 10.1128/iai.00431-17. [PMID: 28717028]
  • Vanajothi Ramar, Srinivasan Pappu. Exploring the inhibitory potential of bioactive compound from Luffa acutangula against NF-κB-A molecular docking and dynamics approach. Computational biology and chemistry. 2016 06; 62(?):29-35. doi: 10.1016/j.compbiolchem.2016.03.006. [PMID: 27061144]
  • Andrea E Schwaninger, Markus R Meyer, Josef Zapp, Hans H Maurer. Sulfation of the 3,4-methylenedioxymethamphetamine (MDMA) metabolites 3,4-dihydroxymethamphetamine (DHMA) and 4-hydroxy-3-methoxymethamphetamine (HMMA) and their capability to inhibit human sulfotransferases. Toxicology letters. 2011 Apr; 202(2):120-8. doi: 10.1016/j.toxlet.2011.01.026. [PMID: 21295122]
  • Kenji Ishihara, Naruo Katsutani, Toyohiko Aoki. A metabonomics study of the hepatotoxicants galactosamine, methylene dianiline and clofibrate in rats. Basic & clinical pharmacology & toxicology. 2006 Sep; 99(3):251-60. doi: 10.1111/j.1742-7843.2006.pto_455.x. [PMID: 16930299]
  • Jakob Peter Ley, Karin Engelhart, Jürgen Bernhardt, Heinz-Jürgen Bertram. 3,4-Dihydroxymandelic acid, a noradrenalin metabolite with powerful antioxidative potential. Journal of agricultural and food chemistry. 2002 Oct; 50(21):5897-902. doi: 10.1021/jf025667e. [PMID: 12358456]
  • Wen-Xin Dong, Xiang-Lian Ni. Norepinephrine metabolism in neuron: dissociation between 3,4-dihydroxyphenylglycol and 3,4-dihydroxymandelic acid pathways. Acta pharmacologica Sinica. 2002 Jan; 23(1):59-65. doi: . [PMID: 11860739]
  • H Kusuhara, T Sekine, N Utsunomiya-Tate, M Tsuda, R Kojima, S H Cha, Y Sugiyama, Y Kanai, H Endou. Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. The Journal of biological chemistry. 1999 May; 274(19):13675-80. doi: 10.1074/jbc.274.19.13675. [PMID: 10224140]
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  • M Kawamura, I J Kopin, P F Kador, S Sato, O Tjurmina, G Eisenhofer. Effects of aldehyde/aldose reductase inhibition on neuronal metabolism of norepinephrine. Journal of the autonomic nervous system. 1997 Oct; 66(3):145-8. doi: 10.1016/s0165-1838(97)00086-6. [PMID: 9406118]
  • S J Ley, A E Waterman, A Livingston. Measurement of mechanical thresholds, plasma cortisol and catecholamines in control and lame cattle: a preliminary study. Research in veterinary science. 1996 Sep; 61(2):172-3. doi: 10.1016/s0034-5288(96)90096-x. [PMID: 8880991]
  • W X Dong, J Schneider, P Lacolley, A M Brisac, M Safar, J L Cuche. Neuronal metabolism of catecholamines: plasma DHPG, DOMA and DOPAC. Journal of the autonomic nervous system. 1993 Aug; 44(2-3):109-17. doi: 10.1016/0165-1838(93)90023-n. [PMID: 8227950]
  • T Lenz, E Werle, G Strobel, H Weicker. O-Methylated and sulfoconjugated catecholamines: differential activities at human platelet alpha 2-adrenoceptors. Canadian journal of physiology and pharmacology. 1991 Jul; 69(7):929-37. doi: 10.1139/y91-141. [PMID: 1683267]
  • E Schömig, J Babin-Ebell, M Gliese, H Russ. Extraneuronal inactivation of noradrenaline in tissue culture. Journal of neural transmission. Supplementum. 1991; 34(?):43-9. doi: 10.1007/978-3-7091-9175-0_6. [PMID: 1817163]
  • A J McCance, J C Forfar. Plasma [3H]noradrenaline kinetics in man: is separation of alumina extracts by high performance liquid chromatography necessary?. Clinical science (London, England : 1979). 1988 Feb; 74(2):151-4. doi: 10.1042/cs0740151. [PMID: 3338259]
  • B M Eriksson, B A Persson. Liquid chromatographic method for the determination of 3,4-dihydroxyphenylethylene glycol and 3,4-dihydroxymandelic acid in plasma. Journal of chromatography. 1987 Jan; 386(?):1-9. doi: 10.1016/s0021-9673(01)94578-9. [PMID: 3104378]
  • L G Howes, A MacGilchrist, C Hawksby, D Sumner, J L Reid. An improved approach for the determination of plasma [3H]noradrenaline kinetics using high-performance liquid chromatography. Clinical science (London, England : 1979). 1986 Aug; 71(2):211-5. doi: 10.1042/cs0710211. [PMID: 3720197]
  • M Mizukoshi, T Hano, M Kuchii, I Nishio, Y Masuyama. Plasma noradrenaline and its deaminated metabolites in essential hypertension and pheochromocytoma. Japanese circulation journal. 1985 Sep; 49(9):1035-42. doi: 10.1253/jcj.49.1035. [PMID: 4068201]
  • S Ito, T Kato, K Maruta, K Jimbow, K Fujita. 'Total' acidic metabolites of catecholamines in urine as determined by hydrolysis with hydriodic acid and liquid chromatography: application to patients with neuroblastoma and melanoma. Clinical chemistry. 1985 Jul; 31(7):1185-8. doi: 10.1093/clinchem/31.7.1185. [PMID: 4006189]
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  • T Nishihata, H Takahagi, M Yamamoto, H Tomida, J H Rytting, T Higuchi. Enhanced rectal absorption of cefmetazole and cefoxitin in the presence of epinephrine metabolites in rats and a high-performance liquid chromatographic assay for cephamycin antibiotics. Journal of pharmaceutical sciences. 1984 Jan; 73(1):109-12. doi: 10.1002/jps.2600730129. [PMID: 6582265]
  • J L Izzo, D Greulich. Radioenzymatic assay for plasma dihydroxyphenylglycol (DHPG), dihydroxymandelic acid (DOMA) and dihydroxyphenylacetic acid (DOPAC). Life sciences. 1983 Aug; 33(5):483-8. doi: 10.1016/0024-3205(83)90798-1. [PMID: 6877032]
  • N D Vlachakis, C Lampano, N Alexander, R F Maronde. Catecholamines and their major metabolites in plasma and cerebrospinal fluid of man. Brain research. 1981 Dec; 229(1):67-74. doi: 10.1016/0006-8993(81)90746-0. [PMID: 7306812]
  • M Nagel-Hiemke, H J Schümann. A sensitive radioenzymatic assay for dihydroxymandelic acid, dihydroxypenylglycol and dihydroxyphenylacetic acid. Journal of biochemical and biophysical methods. 1981 Jun; 4(5-6):261-70. doi: 10.1016/0165-022x(81)90066-x. [PMID: 7019296]
  • Y WADA, N WATANABE. URINARY EXCRETION OF 3,4-DIHYDROXYMANDELIC ACID (DOMA) IN PATIENTS WITH HYPERTENSION AND WITH HYPERTHYROIDISM. The Tohoku journal of experimental medicine. 1964 Nov; 84(?):161-5. doi: 10.1620/tjem.84.161. [PMID: 14235825]
  • V DEQUATTRO, D WYBENGA, VON STUDNITZ, S BRUNJES. DETERMINATION OF URINARY 3,4-DIHYDROXYMANDELIC ACID. The Journal of laboratory and clinical medicine. 1964 May; 63(?):864-78. doi: NULL. [PMID: 14158069]
  • Y WADA. QUANTITATIVE DETERMINATION OF 3,4-DIHYDROXYMANDELIC ACID (DOMA) IN HUMAN URINE. The Tohoku journal of experimental medicine. 1963 May; 79(?):389-400. doi: 10.1620/tjem.79.389. [PMID: 14043397]