Uroporphyrin III (BioDeep_00000004928)

 

Secondary id: BioDeep_00001869218

human metabolite Endogenous


代谢物信息卡片


3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid

化学式: C40H38N4O16 (830.2282708)
中文名称:
谱图信息: 最多检出来源 Macaca mulatta(otcml) 27.08%

分子结构信息

SMILES: C1=C2C(=C(C(=CC3=NC(=CC4=NC(=CC5=C(C(=C1N5)CCC(=O)O)CC(=O)O)C(=C4CCC(=O)O)CC(=O)O)C(=C3CCC(=O)O)CC(=O)O)N2)CC(=O)O)CCC(=O)O
InChI: InChI=1S/C40H38N4O16/c45-33(46)5-1-17-21(9-37(53)54)29-14-27-19(3-7-35(49)50)22(10-38(55)56)30(43-27)15-28-20(4-8-36(51)52)24(12-40(59)60)32(44-28)16-31-23(11-39(57)58)18(2-6-34(47)48)26(42-31)13-25(17)41-29/h13-16,41-42H,1-12H2,(H,45,46)(H,47,48)(H,49,50)(H,51,52)(H,53,54)(H,55,56)(H,57,58)(H,59,60)

描述信息

Uroporphyrin is the porphyrin produced by oxidation of the methylene bridges in uroporphyrinogen. Uroporphyrins have four acetic acid and four propionic acid side chains attached to their pyrrole rings. The enzyme uroporphyrinogen I synthase catalyzes the formation of hydroxymethylbilane from four molecules of porphobilinogen. Uroporphyrinogen III cosynthase then catalyzes the conversion of hydroxymethylbilane into uroporphyrinogen III. Otherwise, hydroxymethylbilane cyclizes nonenzymatically to form uroporphyrinogen I. Uroporphyrinogen I and III yield their respective uroporphyrins via autooxidation or their respective coproporphyrinogens via decarboxylation. Excessive amounts of uroporphyrin I are excreted in congenital erythropoietic porphyria, and both uroporphyrin I and uroporphyrin III are excreted in porphyria cutanea tarda. Uroporphyrin I and III are the most common isomers. Under certain conditions, uroporphyrin III can act as a phototoxin, a neurotoxin, and a metabotoxin. A phototoxin leads to cell damage upon exposure to light. A neurotoxin causes damage to nerve cells and nerve tissues. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of porphyrins are associated with porphyrias such as porphyria variegate, acute intermittent porphyria, porphyria cutanea tarda, and hereditary coproporphyria (HCP). There are several types of porphyrias (most are inherited). Hepatic porphyrias are characterized by acute neurological attacks (seizures, psychosis, extreme back and abdominal pain, and an acute polyneuropathy), while the erythropoietic forms present with skin problems (usually a light-sensitive blistering rash and increased hair growth). The neurotoxicity of porphyrins may be due to their selective interactions with tubulin, which disrupt microtubule formation and cause neural malformations (PMID: 3441503).
Occurs in urine in small amounts as by-product of haem biosynthesis, also in Rhodopseudomonas spheroides (CCD). Uroporphyrin III is found in soy bean.

同义名列表

12 个代谢物同义名

3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1,3,5,7,9,11(23),12,14,16,18(21),19-undecaen-4-yl]propanoic acid; 3-[9,14,20-tris(2-carboxyethyl)-5,10,15,19-tetrakis(carboxymethyl)-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(21),2,4,6,8(23),9,11,13,15,17,19-undecaen-4-yl]propanoic acid; 3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropionic acid; 3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoic acid; 3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropionate; 3,8,13,17-Tetrakis(carboxymethyl)porphyrin-2,7,12,18-tetrapropanoate; 3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionic acid; 3,8,13,17-Tetramethyl-2,7,12,18-porphinetetrapropionate; Coproporphyrin III; uroporphyrin III; Uroporphyrin 3; Uroporphyrin III



数据库引用编号

14 个数据库交叉引用编号

分类词条

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代谢反应

0 个相关的代谢反应过程信息。

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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。
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文献列表

  • Makiko Yasuda, Angelika L Erwin, Lawrence U Liu, Manisha Balwani, Brenden Chen, Senkottuvelan Kadirvel, Lin Gan, M Isabel Fiel, Ronald E Gordon, Chunli Yu, Sonia Clavero, Antonios Arvelakis, Hetanshi Naik, L David Martin, John D Phillips, Karl E Anderson, Vaithamanithi M Sadagoparamanujam, Sander S Florman, Robert J Desnick. Liver Transplantation for Acute Intermittent Porphyria: Biochemical and Pathologic Studies of the Explanted Liver. Molecular medicine (Cambridge, Mass.). 2015 Jun; 21(?):487-95. doi: 10.2119/molmed.2015.00099. [PMID: 26062020]
  • Wei Huang, Qian Liu, Er-Yi Zhu, Ali Abbas Falih Shindi, Yao-Qun Li. Rapid simultaneous determination of protoporphyrin IX, uroporphyrin III and coproporphyrin III in human whole blood by non-linear variable-angle synchronous fluorescence technique coupled with partial least squares. Talanta. 2010 Sep; 82(4):1516-20. doi: 10.1016/j.talanta.2010.07.034. [PMID: 20801366]
  • Guo-dong Deng, Bao-shan Zheng, Cheng Zhai, Jian-ping Wang, Jack C Ng. [Porphyrins as the early biomarkers for arsenic exposure of human]. Huan jing ke xue= Huanjing kexue. 2007 May; 28(5):1147-52. doi: NULL. [PMID: 17633194]
  • Ricardo Negroni, Alicia Arechavala, Elena Maiolo. [Clinical cases in medical mycology. Case no. 20]. Revista iberoamericana de micologia. 2006 Jun; 23(2):116-8. doi: 10.1016/s1130-1406(06)70028-6. [PMID: 16854192]
  • Peter Bozek, Milan Hutta, Barbora Hrivnáková. Rapid analysis of porphyrins at low ng/l and microg/l levels in human urine by a gradient liquid chromatography method using octadecylsilica monolithic columns. Journal of chromatography. A. 2005 Aug; 1084(1-2):24-32. doi: 10.1016/j.chroma.2005.06.007. [PMID: 16114232]
  • Jordi To-Figueras, Dolores Ozalla, Carmen Herrero Mateu. Long-standing changes in the urinary profile of porphyrin isomers after clinical remission of porphyria cutanea tarda. Annals of clinical and laboratory science. 2003; 33(3):251-6. doi: . [PMID: 12956438]
  • S W Ryter, R M Tyrrell. The heme synthesis and degradation pathways: role in oxidant sensitivity. Heme oxygenase has both pro- and antioxidant properties. Free radical biology & medicine. 2000 Jan; 28(2):289-309. doi: 10.1016/s0891-5849(99)00223-3. [PMID: 11281297]
  • E Mylchreest, M Charbonneau. Studies on the mechanism of uroporphyrinogen decarboxylase inhibition in hexachlorobenzene-induced porphyria in the female rat. Toxicology and applied pharmacology. 1997 Jul; 145(1):23-33. doi: 10.1006/taap.1997.8157. [PMID: 9221820]
  • M A El-Far, N R Pimstone. Tumour localization of uroporphyrin isomers I and III and their correlation to albumin and serum protein binding. Cell biochemistry and function. 1983 Oct; 1(3):156-60. doi: 10.1002/cbf.290010307. [PMID: 6678621]
  • S Sandberg, J Glette, G Hopen, C O Solberg, I Romslo. Porphyrin-induced photodamage to isolated human neutrophils. Photochemistry and photobiology. 1981 Oct; 34(4):471-5. doi: NULL. [PMID: 7312953]
  • R S Day, L Eales. Porphyrins in chronic renal failure. Nephron. 1980; 26(2):90-5. doi: 10.1159/000181958. [PMID: 6997766]
  • R GARCIN, A ESCALIER, A GAJDOS, GASDOS-TOROK, S GODLEWSKI, J LAPRESLE. [Acute porphyria with porphyrins with 3, 5 and 7 carboxyls in urine in addition to uroporphyrin III; a clinical and biochemical study]. La Presse medicale. 1953 Jul; 61(46):959-60. doi: . [PMID: 13088776]