Dopamine 3-O-sulfate (BioDeep_00000009510)

 

Secondary id: BioDeep_00001872241

human metabolite Endogenous blood metabolite Volatile Flavor Compounds


代谢物信息卡片


4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulphuric acid)

化学式: C8H11NO5S (233.0357916)
中文名称: 多巴胺3-O-硫酸盐
谱图信息: 最多检出来源 Homo sapiens(blood) 5.53%

Reviewed

Last reviewed on 2024-09-13.

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Dopamine 3-O-sulfate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/dopamine_3-o-sulfate (retrieved 2024-11-22) (BioDeep RN: BioDeep_00000009510). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC(=C(C=C1CCN)OS(=O)(=O)O)O
InChI: InChI=1S/C8H11NO5S/c9-4-3-6-1-2-7(10)8(5-6)14-15(11,12)13/h1-2,5,10H,3-4,9H2,(H,11,12,13)

描述信息

Dopamine 3-O-sulfate is a sulfonated form of dopamine. In human blood circulation endogenous dopamine exists predominantly in the sulfated form and dopamine sulfate accounts for more than 90\\% of all dopamine. Dopamine-3-O-sulfate predominates in human plasma, with concentrations about 10-fold higher than those of the regioisomer dopamine-4-O-sulfate. Sulfonation is the most important metabolic pathway that interferes with the binding of dopamine to its receptors. The origins of this preponderance for Dopamine-3-O-sulfate have not been determined, although there has been speculation about the contribution of the specificity of transport proteins and/or arylsulfatases. It has also been proposed to depend on the regiospecificity of the metabolizing enzyme(s) for the 3-hydroxy group of dopamine. It is believed that the vast majority of circulating dopamine sulfate originates in the upper gastrointestinal tract, and indeed that is the main site of expression of the enzyme responsible for its formation. Aryl sulfotransferase (SULT1A3, EC 2.8.2.1) is an enzyme that catalyzes the sulfonation of many endogenous and exogenous phenols and catechols; the most important endogenous substrate is dopamine. SULT1A3 strongly favors the 3-hydroxy group of dopamine over the 4-hydroxy group and may indeed be primarily responsible for the difference between the circulating levels of dopamine sulfates in human blood. (PMID: 17548063) [HMDB]
Dopamine 3-O-sulfate is a sulfonated form of dopamine. In human blood circulation endogenous dopamine exists predominantly in the sulfated form and dopamine sulfate accounts for more than 90\\% of all dopamine. Dopamine-3-O-sulfate predominates in human plasma, with concentrations about 10-fold higher than those of the regioisomer dopamine-4-O-sulfate. Sulfonation is the most important metabolic pathway that interferes with the binding of dopamine to its receptors. The origins of this preponderance for Dopamine-3-O-sulfate have not been determined, although there has been speculation about the contribution of the specificity of transport proteins and/or arylsulfatases. It has also been proposed to depend on the regiospecificity of the metabolizing enzyme(s) for the 3-hydroxy group of dopamine. It is believed that the vast majority of circulating dopamine sulfate originates in the upper gastrointestinal tract, and indeed that is the main site of expression of the enzyme responsible for its formation. Aryl sulfotransferase (SULT1A3, EC 2.8.2.1) is an enzyme that catalyzes the sulfonation of many endogenous and exogenous phenols and catechols; the most important endogenous substrate is dopamine. SULT1A3 strongly favors the 3-hydroxy group of dopamine over the 4-hydroxy group and may indeed be primarily responsible for the difference between the circulating levels of dopamine sulfates in human blood. (PMID: 17548063).

同义名列表

21 个代谢物同义名

4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulphuric acid); 4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulfuric acid); [5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulphonic acid; [5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulfonic acid; 4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulphate); 4-(2-Aminoethyl)-1,2-benzenediol 2-(hydrogen sulfate); [5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulphonate; [5-(2-Aminoethyl)-2-hydroxyphenyl]oxidanesulfonate; Dopamine 3-monosulphuric acid; Dopamine 3-monosulfuric acid; Dopamine 3-O-sulphuric acid; Dopamine 3-O-sulfuric acid; Dopamine 3-sulphuric acid; Dopamine 3-sulfuric acid; Dopamine 3-monosulphate; Dopamine 3-monosulfate; Dopamine 3-O-sulphate; dopamine 3-O-sulfate; Dopamine 3-sulphate; Dopamine 3-sulfate; Dopamine 3-O-sulfate



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(0)

PlantCyc(0)

代谢反应

40 个相关的代谢反应过程信息。

Reactome(40)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

1 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。



文献列表

  • Ebbe Eldrup. Significance and origin of DOPA, DOPAC, and dopamine-sulphate in plasma, tissues and cerebrospinal fluid. Danish medical bulletin. 2004 Feb; 51(1):34-62. doi: NULL. [PMID: 16009071]
  • D S Goldstein, K J Swoboda, J M Miles, S W Coppack, A Aneman, C Holmes, I Lamensdorf, G Eisenhofer. Sources and physiological significance of plasma dopamine sulfate. The Journal of clinical endocrinology and metabolism. 1999 Jul; 84(7):2523-31. doi: 10.1210/jcem.84.7.5864. [PMID: 10404831]
  • E Eldrup, S E Møller, J Andreasen, N J Christensen. Effects of ordinary meals on plasma concentrations of 3,4-dihydroxyphenylalanine, dopamine sulphate and 3,4-dihydroxyphenylacetic acid. Clinical science (London, England : 1979). 1997 Apr; 92(4):423-30. doi: 10.1042/cs0920423. [PMID: 9176043]
  • M Yoshizumi, T Kitagawa, T Hori, I Katoh, H Houchi, T Ohuchi, M Oka. Physiological significance of plasma sulfoconjugated dopamine in patients with hypertension--clinical and experimental studies. Life sciences. 1996; 59(4):324-30. doi: 10.1016/0024-3205(96)00301-3. [PMID: 8761004]
  • Y Mizutani, Y Okada, M Ogawa, T Hasegawa, T Nabeshima. Pharmacokinetic model of oral levodopa and role of carbidopa in parkinsonian patients. Biological & pharmaceutical bulletin. 1995 Dec; 18(12):1729-37. doi: 10.1248/bpb.18.1729. [PMID: 8787797]
  • D Ratge, K P Kohse, U Steegmüller, H Wisser. Distribution of free and conjugated catecholamines between plasma, platelets and erythrocytes: different effects of intravenous and oral catecholamine administrations. The Journal of pharmacology and experimental therapeutics. 1991 Apr; 257(1):232-8. doi: NULL. [PMID: 2019988]
  • G Strobel, H Weicker. Catecholamine sulfates as internal standards in HPLC determinations of sulfoconjugated catecholamines in plasma and urine. Clinical chemistry. 1991 Feb; 37(2):196-9. doi: 10.1093/clinchem/37.2.196. [PMID: 1993323]
  • K Murata, K Noda, K Kohno, M Samejima. Pharmacokinetic analysis of absorption and metabolism of dopamine and a dopamine prodrug in dogs. Biopharmaceutics & drug disposition. 1990 Mar; 11(2):149-56. doi: 10.1002/bdd.2510110207. [PMID: 2328300]
  • M S Sothmann, J Blaney, T Woulfe, S Donahue-Fuhrman, K Lefever, A B Gustafson, V S Murthy. Plasma free and sulfoconjugated catecholamines during sustained exercise. Journal of applied physiology (Bethesda, Md. : 1985). 1990 Feb; 68(2):452-6. doi: 10.1152/jappl.1990.68.2.452. [PMID: 2318755]
  • E Kienzl, K Eichinger, E Sofic, K Jellinger, P Riederer, W Kuhn, G Fuchs, G Laux. Urinary dopamine sulfate: regulations and significance in neurological disorders. Journal of neural transmission. Supplementum. 1990; 32(?):471-9. doi: 10.1007/978-3-7091-9113-2_64. [PMID: 2089110]
  • K Hashizume, A Yamatodani, T Yamamoto, H Wada, T Ogihara. Contents of dopamine sulfoconjugate isomers and their desulfation in dog arteries. Biochemical pharmacology. 1989 Jun; 38(12):1891-5. doi: 10.1016/0006-2952(89)90486-3. [PMID: 2742597]
  • E Kienzl, K Eichinger. Preparation of dopamine 3-O-sulphate and dopamine 4-O-sulphate as reference substances and high-performance liquid chromatographic trace determination. Journal of chromatography. 1988 Sep; 430(2):263-9. doi: 10.1016/s0378-4347(00)83161-8. [PMID: 3235502]
  • K Hashizume, T Ogihara, A Yamatodani, T Yamamoto, H Wada, Y Kumahara. Plasma levels and renal clearance of two isomers of dopamine sulfate in patients with essential hypertension. Clinical and experimental hypertension. Part A, Theory and practice. 1988; 10(4):561-74. doi: 10.3109/10641968809033909. [PMID: 3390960]
  • K Hashizume, A Yamatodani, T Yamamoto, T Ogihara, Y Kumahara, H Wada. Effects of oral and intravenous administrations of dopamine and L-dopa on plasma levels of two isomers of dopamine sulfate in man. Life sciences. 1987 Dec; 41(25):2697-704. doi: 10.1016/0024-3205(87)90462-0. [PMID: 3695802]
  • M Oka, Y Ishimura, T Tsunematsu, K Minakuchi, T Ohuchi, K Matsumoto. Effects of administration of dopamine and L-DOPA to dogs on their plasma level of dopamine sulfate. Biochemical pharmacology. 1987 Oct; 36(19):3205-8. doi: 10.1016/0006-2952(87)90634-4. [PMID: 3663235]
  • M C Scott, M A Elchisak. Direct measurement of dopamine O-sulfate in plasma and cerebrospinal fluid. Journal of chromatography. 1987 Jan; 413(?):17-23. doi: 10.1016/0378-4347(87)80209-8. [PMID: 3558665]
  • G M Tyce, J M Messick, T L Yaksh, D E Byer, D R Danielson, D K Rorie. Amine sulfate formation in the central nervous system. Federation proceedings. 1986 Jul; 45(8):2247-53. doi: NULL. [PMID: 3459671]
  • T Yamamoto, A Yamatodani, M Nishimura, H Wada. Determination of dopamine-3- and 4-O-sulphate in human plasma and urine by anion-exchange high-performance liquid chromatography with fluorimetric detection. Journal of chromatography. 1985 Aug; 342(2):261-7. doi: 10.1016/s0378-4347(00)84516-8. [PMID: 4055948]
  • T Tsunematsu. Formation of dopamine sulfate from L-dopa by perfusion of dog kidney. The Tokushima journal of experimental medicine. 1985 Jun; 32(1-2):23-9. doi: NULL. [PMID: 3938080]
  • K Rácz, N T Buu, O Kuchel, A De Léan. Dopamine 3-sulfate inhibits aldosterone secretion in cultured bovine adrenal cells. The American journal of physiology. 1984 Oct; 247(4 Pt 1):E431-5. doi: 10.1152/ajpendo.1984.247.4.e431. [PMID: 6496664]
  • M A Elchisak. Determination of dopamine-O-sulfate and norepinephrine-O-sulfate isomers and serotonin-O-sulfate by high-performance liquid chromatography using dual-electrode electrochemical detection. Journal of chromatography. 1983 Jul; 264(1):119-27. doi: 10.1016/s0021-9673(01)95011-3. [PMID: 6688426]
  • M A Elchisak, J H Carlson. Method for analysis of dopamine sulfate isomers by high performance liquid chromatography. Life sciences. 1982 Jun; 30(26):2325-36. doi: 10.1016/0024-3205(82)90260-0. [PMID: 7109849]
  • N T Buu, G Nair, O Kuchel, J Genest. The extra-adrenal synthesis of epinephrine in rats. Possible involvement of dopamine sulfate. The Journal of laboratory and clinical medicine. 1981 Oct; 98(4):527-35. doi: NULL. [PMID: 6793680]
  • G A Johnson, C A Baker, R T Smith. Radioenzymatic assay of sulfate conjugates of catecholamines and DOPA in plasma. Life sciences. 1980 May; 26(19):1591-8. doi: 10.1016/0024-3205(80)90362-8. [PMID: 6770210]