Protoporphyrinogen IX (BioDeep_00000004563)

 

Secondary id: BioDeep_00001869234

human metabolite PANOMIX_OTCML-2023 Endogenous Volatile Flavor Compounds


代谢物信息卡片


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

化学式: C34H40N4O4 (568.30494)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(blood) 0.12%

分子结构信息

SMILES: C=Cc1c(C)c2Cc3c(C)c(CCC(=O)O)c(Cc4c(CCC(=O)O)c(C)c(Cc5c(C=C)c(C)c(Cc1[nH]2)[nH]5)[nH]4)[nH]3
InChI: InChI=1S/C34H40N4O4/c1-7-21-17(3)25-13-26-19(5)23(9-11-33(39)40)31(37-26)16-32-24(10-12-34(41)42)20(6)28(38-32)15-30-22(8-2)18(4)27(36-30)14-29(21)35-25/h7-8,35-38H,1-2,9-16H2,3-6H3,(H,39,40)(H,41,42)

描述信息

Protoporphyrinogen IX is an intermediate in heme biosynthesis. It is a porphyrinogen in which two pyrrole rings each have one methyl and one propionate side chain, and the other two pyrrole rings each have one methyl and one vinyl side chain. Fifteen isomers are possible but only one, type IX, occurs naturally. Protoporphyrinogen is produced by oxidative decarboxylation of coproporphyrinogen. Under certain conditions, protoporphyrinogen IX 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, and hereditary coproporphyria (HCP). In particular, protoporphyrinogen IX is accumulated and excreted excessively in the feces in acute intermittent porphyria, protoporphyria, and variegate porphyria. 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).
Protoporphyrinogen IX is an intermediate in heme biosynthesis. It is a porphyrinogen in which 2 pyrrole rings each have one methyl and one propionate side chain and the other two pyrrole rings each have one methyl and one vinyl side chain. 15 isomers are possible but only one, type IX, occurs naturally. Protoporphyrinogen is produced by oxidative decarboxylation of coproporphyrinogen. [HMDB]. Protoporphyrinogen IX is found in many foods, some of which are elderberry, grapefruit, green vegetables, and pepper (c. annuum).
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同义名列表

10 个代谢物同义名

3-[20-(2-carboxyethyl)-9,14-diethenyl-5,10,15,19-tetramethyl-21,22,23,24-tetraazapentacyclo[16.2.1.1^{3,6}.1^{8,11}.1^{13,16}]tetracosa-1(20),3,5,8,10,13,15,18-octaen-4-yl]propanoic acid; 7,12-Diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoic acid; 7,12-Diethenyl-5,10,15,20,22,24-hexahydro-3,8,13,17-tetramethyl-21H,23H-porphine-2,18-dipropanoate; 7,12-Diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoic acid; 7,12-Diethenyl-3,8,13,17-tetramethyl-5,10,15,20,22,24-hexahydroporphyrin-2,18-dipropanoate; 5,10,15,20,22,24-Hexahydro protoporphyrin IX deriv.; Protoporphyrinogen IX; Protoporphyrinogen-IX; protoporphyrinogen; Protoporphyrinogen IX



数据库引用编号

17 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(1)

PlantCyc(0)

代谢反应

81 个相关的代谢反应过程信息。

Reactome(54)

BioCyc(3)

WikiPathways(2)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(20)

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。



文献列表

  • Pawel Brzezowski, Brigitte Ksas, Michel Havaux, Bernhard Grimm, Marie Chazaux, Gilles Peltier, Xenie Johnson, Jean Alric. The function of PROTOPORPHYRINOGEN IX OXIDASE in chlorophyll biosynthesis requires oxidised plastoquinone in Chlamydomonas reinhardtii. Communications biology. 2019; 2(?):159. doi: 10.1038/s42003-019-0395-5. [PMID: 31069268]
  • Dieter Hackenberg, Ulrich Keetman, Bernhard Grimm. Homologous NF-YC2 subunit from Arabidopsis and tobacco is activated by photooxidative stress and induces flowering. International journal of molecular sciences. 2012; 13(3):3458-3477. doi: 10.3390/ijms13033458. [PMID: 22489162]
  • Irene Russo Krauss, Filomena Sica, Carlo Andrea Mattia, Antonello Merlino. Increasing the X-ray diffraction power of protein crystals by dehydration: the case of bovine serum albumin and a survey of literature data. International journal of molecular sciences. 2012; 13(3):3782-800. doi: 10.3390/ijms13033782. [PMID: 22489183]
  • Tom A Mendum, Jane Newcombe, Ahmad A Mannan, Andrzej M Kierzek, Johnjoe McFadden. Interrogation of global mutagenesis data with a genome scale model of Neisseria meningitidis to assess gene fitness in vitro and in sera. Genome biology. 2011 Dec; 12(12):R127. doi: 10.1186/gb-2011-12-12-r127. [PMID: 22208880]
  • Haibo Yu, Huibin Yang, Dongliang Cui, Liang Lv, Bin Li. Synthesis and herbicidal activity of diphenyl ether derivatives containing unsaturated carboxylates. Journal of agricultural and food chemistry. 2011 Nov; 59(21):11718-26. doi: 10.1021/jf2039444. [PMID: 21958315]
  • Zhiwei Huang, Kaifu Chen, Tao Xu, Jianhuai Zhang, Yongxiang Li, Wei Li, Ameeta K Agarwal, Alice M Clark, John D Phillips, Xuewen Pan. Sampangine inhibits heme biosynthesis in both yeast and human. Eukaryotic cell. 2011 Nov; 10(11):1536-44. doi: 10.1128/ec.05170-11. [PMID: 21908598]
  • Emilia Balsemão-Pires, Yvon Jaillais, Bradley J S C Olson, Leonardo R Andrade, James G Umen, Joanne Chory, Gilberto Sachetto-Martins. The Arabidopsis translocator protein (AtTSPO) is regulated at multiple levels in response to salt stress and perturbations in tetrapyrrole metabolism. BMC plant biology. 2011 Jun; 11(?):108. doi: 10.1186/1471-2229-11-108. [PMID: 21689410]
  • Jerry M Green, Micheal D K Owen. Herbicide-resistant crops: utilities and limitations for herbicide-resistant weed management. Journal of agricultural and food chemistry. 2011 Jun; 59(11):5819-29. doi: 10.1021/jf101286h. [PMID: 20586458]
  • Li-Li Jiang, Yang Zuo, Zhi-Fang Wang, Yin Tan, Qiong-You Wu, Zhen Xi, Guang-Fu Yang. Design and syntheses of novel N-(benzothiazol-5-yl)-4,5,6,7-tetrahydro-1H-isoindole-1,3(2H)-dione and N-(benzothiazol-5-yl)isoindoline-1,3-dione as potent protoporphyrinogen oxidase inhibitors. Journal of agricultural and food chemistry. 2011 Jun; 59(11):6172-9. doi: 10.1021/jf200616y. [PMID: 21517076]
  • Patrick J Tranel, Chance W Riggins, Michael S Bell, Aaron G Hager. Herbicide resistances in Amaranthus tuberculatus: a call for new options. Journal of agricultural and food chemistry. 2011 Jun; 59(11):5808-12. doi: 10.1021/jf103797n. [PMID: 21073196]
  • Roman Sobotka, Martin Tichy, Annegret Wilde, C Neil Hunter. Functional assignments for the carboxyl-terminal domains of the ferrochelatase from Synechocystis PCC 6803: the CAB domain plays a regulatory role, and region II is essential for catalysis. Plant physiology. 2011 Apr; 155(4):1735-47. doi: 10.1104/pp.110.167528. [PMID: 21081693]
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  • Qiongyou Wu, Guodong Wang, Shaowei Huang, Long Lin, Guangfu Yang. Synthesis and biological activity of novel phenyltriazolinone derivatives. Molecules (Basel, Switzerland). 2010 Dec; 15(12):9024-34. doi: 10.3390/molecules15129024. [PMID: 21150822]
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  • Ralph Kissen, Per Winge, Diem Hong Thi Tran, Tommy S Jørstad, Trond R Størseth, Tone Christensen, Atle M Bones. Transcriptional profiling of an Fd-GOGAT1/GLU1 mutant in Arabidopsis thaliana reveals a multiple stress response and extensive reprogramming of the transcriptome. BMC genomics. 2010 Mar; 11(?):190. doi: 10.1186/1471-2164-11-190. [PMID: 20307264]
  • Liting Lim, Geoffrey Ian McFadden. The evolution, metabolism and functions of the apicoplast. Philosophical transactions of the Royal Society of London. Series B, Biological sciences. 2010 Mar; 365(1541):749-63. doi: 10.1098/rstb.2009.0273. [PMID: 20124342]
  • Beilei Lei, Jiazhong Li, Jing Lu, Juan Du, Huanxiang Liu, Xiaojun Yao. Rational prediction of the herbicidal activities of novel protoporphyrinogen oxidase inhibitors by quantitative structure-activity relationship model based on docking-guided active conformation. Journal of agricultural and food chemistry. 2009 Oct; 57(20):9593-8. doi: 10.1021/jf902010g. [PMID: 19780536]
  • C Kochs, E Mühlenstädt, N J Neumann, S Hanneken. [Solarium-induced pseudoporphyria and variegate porphyria as rare differential diagnoses of porphyria cutanea tarda]. Der Hautarzt; Zeitschrift fur Dermatologie, Venerologie, und verwandte Gebiete. 2009 Oct; 60(10):790-3. doi: 10.1007/s00105-009-1846-6. [PMID: 19756434]
  • Neil D Adhikari, Robert Orler, Joanne Chory, John E Froehlich, Robert M Larkin. Porphyrins promote the association of GENOMES UNCOUPLED 4 and a Mg-chelatase subunit with chloroplast membranes. The Journal of biological chemistry. 2009 Sep; 284(37):24783-96. doi: 10.1074/jbc.m109.025205. [PMID: 19605356]
  • A V Corrigall, J A H Campbell, K Siziba, R E Kirsch, P N Meissner. The expression of protoporphyrinogen oxidase in human tissues. Cellular and molecular biology (Noisy-le-Grand, France). 2009 Jul; 55(2):89-95. doi: NULL. [PMID: 19656456]
  • Sharon D Whatley, Nicola G Mason, Jacqueline R Woolf, Robert G Newcombe, George H Elder, Michael N Badminton. Diagnostic strategies for autosomal dominant acute porphyrias: retrospective analysis of 467 unrelated patients referred for mutational analysis of the HMBS, CPOX, or PPOX gene. Clinical chemistry. 2009 Jul; 55(7):1406-14. doi: 10.1373/clinchem.2008.122564. [PMID: 19460837]
  • John W Whitaker, Glenn A McConkey, David R Westhead. The transferome of metabolic genes explored: analysis of the horizontal transfer of enzyme encoding genes in unicellular eukaryotes. Genome biology. 2009; 10(4):R36. doi: 10.1186/gb-2009-10-4-r36. [PMID: 19368726]
  • Franck E Dayan, J'Lynn Howell, Jeffrey D Weidenhamer. Dynamic root exudation of sorgoleone and its in planta mechanism of action. Journal of experimental botany. 2009; 60(7):2107-17. doi: 10.1093/jxb/erp082. [PMID: 19357432]
  • Hua-bin Li, You-quan Zhu, Xiao-wei Song, Fang-zhong Hu, Bin Liu, Yong-hong Li, Zi-xia Niu, Pei Liu, Zhi-hong Wang, Hai-bin Song, Xiao-mao Zou, Hua-zheng Yang. Novel protoporphyrinogen oxidase inhibitors: 3H-pyrazolo[3,4-d][1,2,3]triazin-4-one derivatives. Journal of agricultural and food chemistry. 2008 Oct; 56(20):9535-42. doi: 10.1021/jf801774k. [PMID: 18808144]
  • David P Dixon, Adrian Lapthorn, Panagiotis Madesis, Elisabeth A Mudd, Anil Day, Robert Edwards. Binding and glutathione conjugation of porphyrinogens by plant glutathione transferases. The Journal of biological chemistry. 2008 Jul; 283(29):20268-76. doi: 10.1074/jbc.m802026200. [PMID: 18492666]
  • Franck E Dayan, Daneel Ferreira, Yan-Hong Wang, Ikhlas A Khan, John A McInroy, Zhiqiang Pan. A pathogenic fungi diphenyl ether phytotoxin targets plant enoyl (acyl carrier protein) reductase. Plant physiology. 2008 Jul; 147(3):1062-71. doi: 10.1104/pp.108.118372. [PMID: 18467464]
  • Sunyo Jung, Hye-Jung Lee, Yonghyuk Lee, Kiyoon Kang, Young Soon Kim, Bernhard Grimm, Kyoungwhan Back. Toxic tetrapyrrole accumulation in protoporphyrinogen IX oxidase-overexpressing transgenic rice plants. Plant molecular biology. 2008 Jul; 67(5):535-46. doi: 10.1007/s11103-008-9338-0. [PMID: 18437505]
  • B Mayo, D van Sinderen, M Ventura. Genome analysis of food grade lactic Acid-producing bacteria: from basics to applications. Current genomics. 2008 May; 9(3):169-83. doi: 10.2174/138920208784340731. [PMID: 19440514]
  • Yuhua Zhang, Yifei Wang, Kostya Kanyuka, Martin A J Parry, Stephen J Powers, Nigel G Halford. GCN2-dependent phosphorylation of eukaryotic translation initiation factor-2alpha in Arabidopsis. Journal of experimental botany. 2008; 59(11):3131-41. doi: 10.1093/jxb/ern169. [PMID: 18603615]
  • Marine Froissard, Naïma Belgareh-Touzé, Marylène Dias, Nicole Buisson, Jean-Michel Camadro, Rosine Haguenauer-Tsapis, Emmanuel Lesuisse. Trafficking of siderophore transporters in Saccharomyces cerevisiae and intracellular fate of ferrioxamine B conjugates. Traffic (Copenhagen, Denmark). 2007 Nov; 8(11):1601-16. doi: 10.1111/j.1600-0854.2007.00627.x. [PMID: 17714436]
  • Hazel R Corradi, Anne V Corrigall, Ester Boix, C Gopi Mohan, Edward D Sturrock, Peter N Meissner, K Ravi Acharya. Crystal structure of protoporphyrinogen oxidase from Myxococcus xanthus and its complex with the inhibitor acifluorfen. The Journal of biological chemistry. 2006 Dec; 281(50):38625-33. doi: 10.1074/jbc.m606640200. [PMID: 17046834]
  • Inna Lermontova, Bernhard Grimm. Reduced activity of plastid protoporphyrinogen oxidase causes attenuated photodynamic damage during high-light compared to low-light exposure. The Plant journal : for cell and molecular biology. 2006 Nov; 48(4):499-510. doi: 10.1111/j.1365-313x.2006.02894.x. [PMID: 17059408]
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  • Konstantinos A Aliferis, Maria Chrysayi-Tokousbalides. Metabonomic strategy for the investigation of the mode of action of the phytotoxin (5S,8R,13S,16R)-(-)-pyrenophorol using 1H nuclear magnetic resonance fingerprinting. Journal of agricultural and food chemistry. 2006 Mar; 54(5):1687-92. doi: 10.1021/jf0527798. [PMID: 16506820]
  • Masaki Endo, Keishi Osakabe, Hiroaki Ichikawa, Seiichi Toki. Molecular characterization of true and ectopic gene targeting events at the acetolactate synthase gene in Arabidopsis. Plant & cell physiology. 2006 Mar; 47(3):372-9. doi: 10.1093/pcp/pcj003. [PMID: 16418231]
  • Jianyi Ma, Shufeng Wang, Pinwei Wang, Liangjin Ma, Xiling Chen, Ruifu Xu. Toxicity assessment of 40 herbicides to the green alga Raphidocelis subcapitata. Ecotoxicology and environmental safety. 2006 Mar; 63(3):456-62. doi: 10.1016/j.ecoenv.2004.12.001. [PMID: 16406601]
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