Protoporphyrinogen IX (BioDeep_00000004563)

 

Secondary id: BioDeep_00001869234

human metabolite PANOMIX_OTCML-2023 Endogenous


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 (568.3049)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(natural_products) 6.63%

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。

亚细胞结构定位 关联基因列表
Cytoplasm 5 ALB, CAT, CPOX, HPGDS, IDH1
Peripheral membrane protein 3 CYP1B1, HSD17B6, PPOX
Endoplasmic reticulum membrane 2 CYP1B1, HMOX1
Mitochondrion membrane 3 ABCG2, TMEM14C, TSPO
Nucleus 2 ALB, HMOX1
cytosol 9 ALB, CAT, CPOX, HMOX1, HPGDS, IDH1, IDH2, TSPO, UROD
mitochondrial membrane 4 ABCG2, PPOX, TMEM14C, TSPO
centrosome 1 ALB
nucleoplasm 4 ABCG2, HMOX1, HPGDS, UROD
Cell membrane 5 ABCG2, ITGAM, SLCO1A2, SLCO1B3, SLCO1C1
Cytoplasmic side 1 HMOX1
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 7 ABCC3, ABCG2, SLCO1A2, SLCO1B3, SLCO1C1, TMEM14C, TSPO
Synapse 1 PPOX
cell surface 1 ITGAM
Golgi apparatus 1 ALB
mitochondrial inner membrane 3 FECH, PPOX, TMEM14C
postsynapse 1 PPOX
synaptic vesicle 1 PPOX
Cytoplasm, cytosol 1 IDH1
plasma membrane 6 ABCC3, ABCG2, ITGAM, SLCO1A2, SLCO1B3, SLCO1C1
Membrane 10 ABCC3, ABCG2, CAT, CPOX, CYP1B1, HMOX1, ITGAM, SLCO1A2, SLCO1B3, TSPO
apical plasma membrane 2 ABCG2, SLCO1A2
basolateral plasma membrane 4 ABCC3, SLCO1A2, SLCO1B3, SLCO1C1
extracellular exosome 6 ALB, CAT, IDH1, IDH2, ITGAM, TSPO
Lumenal side 1 HSD17B6
endoplasmic reticulum 4 ALB, HMOX1, HSD17B6, TSPO
extracellular space 3 ALB, HMOX1, ITGAM
perinuclear region of cytoplasm 2 HMOX1, PPOX
mitochondrion 9 CAT, CPOX, CYP1B1, FECH, IDH1, IDH2, PPOX, TMEM14C, TSPO
protein-containing complex 2 ALB, CAT
intracellular membrane-bounded organelle 5 CAT, CYP1B1, HPGDS, HSD17B6, TSPO
Microsome membrane 2 CYP1B1, HSD17B6
Single-pass type I membrane protein 1 ITGAM
Secreted 1 ALB
extracellular region 4 ALB, CAT, IDH1, PPOX
mitochondrial outer membrane 2 HMOX1, TSPO
mitochondrial matrix 3 CAT, FECH, IDH2
anchoring junction 1 ALB
external side of plasma membrane 1 ITGAM
neuronal dense core vesicle lumen 1 PPOX
cytoplasmic vesicle 1 PPOX
Apical cell membrane 1 ABCG2
Mitochondrion inner membrane 2 FECH, PPOX
Membrane raft 2 ABCG2, ITGAM
focal adhesion 1 CAT
Peroxisome 3 CAT, IDH1, IDH2
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, IDH1
peroxisomal membrane 1 CAT
mitochondrial intermembrane space 2 CPOX, PPOX
ciliary basal body 1 ALB
centriole 1 ALB
brush border membrane 1 ABCG2
spindle pole 1 ALB
blood microparticle 1 ALB
Basolateral cell membrane 2 ABCC3, SLCO1B3
specific granule membrane 1 ITGAM
tertiary granule membrane 1 ITGAM
basal plasma membrane 3 ABCC3, SLCO1A2, SLCO1B3
plasma membrane raft 1 ITGAM
ficolin-1-rich granule lumen 2 CAT, IDH1
secretory granule lumen 2 CAT, IDH1
endoplasmic reticulum lumen 1 ALB
platelet alpha granule lumen 1 ALB
tertiary granule lumen 1 IDH1
Single-pass type IV membrane protein 1 HMOX1
Basal cell membrane 3 ABCC3, SLCO1A2, SLCO1B3
external side of apical plasma membrane 1 ABCG2
Rough endoplasmic reticulum 1 PPOX
Intermembrane side 1 PPOX
integrin complex 1 ITGAM
catalase complex 1 CAT
integrin alphaM-beta2 complex 1 ITGAM
ciliary transition fiber 1 ALB


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]
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  • 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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  • Cristiana Gomes de Oliveira Dal'Molin, Lake-Ee Quek, Robin William Palfreyman, Stevens Michael Brumbley, Lars Keld Nielsen. C4GEM, a genome-scale metabolic model to study C4 plant metabolism. Plant physiology. 2010 Dec; 154(4):1871-85. doi: 10.1104/pp.110.166488. [PMID: 20974891]
  • Andreas Richter, Enrico Peter, Yvonne Pörs, Stephan Lorenzen, Bernhard Grimm, Olaf Czarnecki. Rapid dark repression of 5-aminolevulinic acid synthesis in green barley leaves. Plant & cell physiology. 2010 May; 51(5):670-81. doi: 10.1093/pcp/pcq047. [PMID: 20375109]
  • M Reiser, S Eickmann, T Haverkamp, U Finckh. Variegate porphyria in a 46-year-old patient taking sibutramine for weight loss. Obesity reviews : an official journal of the International Association for the Study of Obesity. 2010 Apr; 11(4):329-31. doi: 10.1111/j.1467-789x.2009.00670.x. [PMID: 19845869]
  • Takeaki Goto, Rina Aoki, Kei Minamizaki, Yuichi Fujita. Functional differentiation of two analogous coproporphyrinogen III oxidases for heme and chlorophyll biosynthesis pathways in the cyanobacterium Synechocystis sp. PCC 6803. Plant & cell physiology. 2010 Apr; 51(4):650-63. doi: 10.1093/pcp/pcq023. [PMID: 20194361]
  • 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]
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  • 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]
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  • 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]
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