Pyrrole-2-carboxylic acid (BioDeep_00000001421)

 

Secondary id: BioDeep_00000334833, BioDeep_00000869344

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Marine Natural Products BioNovoGene_Lab2019 natural product


代谢物信息卡片


1H-Pyrrole-2-carboxylic acid

化学式: C5H5NO2 (111.032)
中文名称: 吡咯-2-甲酸, 吡咯-2-羧酸
谱图信息: 最多检出来源 Homo sapiens(blood) 43.85%

Reviewed

Last reviewed on 2024-07-29.

Cite this Page

Pyrrole-2-carboxylic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/pyrrole-2-carboxylic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001421). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CNC(=C1)C(=O)O
InChI: InChI=1S/C5H5NO2/c7-5(8)4-2-1-3-6-4/h1-3,6H,(H,7,8)

描述信息

Pyrrole-2-carboxylic acid was synthesized over a century ago, but its history as a compound of biological origin is rather recent. It was first identified as a degradation product of sialic acids, then as a derivative of the oxidation of the D-hydroxyproline isomers by mammalian D-amino acid oxidase. The latter relationship results from the lability of the direct oxidation product, A-pyrroline-4-hydroxy-2-carboxylic acid, which loses water spontaneously to form the pyrrole. A similar reaction is catalyzed by the more specific allohydroxy-D-proline oxidase of Pseudomonas. In whole animal observations, pyrrole-2-carboxylate (PCA) was identified in rat or human urine after administration of the D-isomers of hydroxyproline, a finding ascribable to the action of D-amino acid oxidase. (PMID:4430715). Urinary excretion of N-(pyrrole-2-carboxyl) glycine has been reported in a 5-year-old affected with type II hyperprolinemia; The child has mild developmental delay, recurrent seizures of the grand mal type and EEG alterations. The urinary excretion of the conjugate is stressed, since it appears that only one previous report in the literature described this compound in the urine of two patients affected by this disturbance (PMID 2383933).
Pyrrole-2-carboxylic acid was synthesized over a century ago, but its history as a compound of biological origin is rather recent. It was first identified as a degradation product of sialic acids, then as a derivative of the oxidation of the D-hydroxyproline isomers by mammalian D-amino acid oxidase. The latter relationship results from the lability of the direct oxidation product, A-pyrroline-4-hydroxy-2-carboxylic acid, which loses water spontaneously to form the pyrrole. A similar reaction is catalyzed by the more specific allohydroxy-D-proline oxidase of Pseudomonas. In whole animal observations, pyrrole-2-carboxylate (PCA) was identified in rat or human urine after administration of the D-isomers of hydroxyproline, a finding ascribable to the action of D-amino acid oxidase. (PMID: 4430715)
KEIO_ID P112
Pyrrole-2-carboxylic acid is a natural alkaloid from the marine bacterium Pelomonas puraquae sp. Nov.
Pyrrole-2-carboxylic acid is a natural alkaloid from the marine bacterium Pelomonas puraquae sp. Nov.

同义名列表

16 个代谢物同义名

2-Pyrrolecarboxylic acid, monosodium salt; 1H-Pyrrole-2-carboxylic acid (9ci); 1-H-Pyrrole-2-carboxylic acid; 1H-Pyrrole-2-carboxylic acid; PYRROLE-2-CARBOXYLIC ACID; 2-Pyrrolecarboxylic acid; Pyrrole-2-carboxylate; Pyrrole 2-carboxylate; 2-Pyrrolecarboxylate; 2-Minaline; Minaline; Minalin; PCA; PYC; Pyrrole-2-carboxylic acid; Pyrrole-2-carboxylic acid



数据库引用编号

25 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

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

53 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 11 ALDH3A2, ARG1, DLK1, ELANE, IDO1, IL15, MTOR, PMP2, PTEN, TYR, VEGFA
Peripheral membrane protein 1 MTOR
Endosome membrane 1 STEAP1
Endoplasmic reticulum membrane 2 ALDH3A2, MTOR
Mitochondrion membrane 1 MAOA
Nucleus 6 ARG1, MTOR, PMP2, PTEN, RBMS1, VEGFA
cytosol 11 ALDH3A2, ARG1, CNDP1, ELANE, IDO1, IL15, MAOA, MTOR, PMP2, PTEN, RBMS1
dendrite 1 MTOR
phagocytic vesicle 2 ELANE, MTOR
nucleoplasm 4 IL15, MTOR, PRODH, PTEN
Cell membrane 1 STEAP1
Cytoplasmic side 3 ALDH3A2, MAOA, MTOR
Cytoplasmic granule 1 ARG1
Multi-pass membrane protein 1 STEAP1
Golgi apparatus membrane 1 MTOR
cell surface 2 ELANE, VEGFA
Golgi apparatus 2 IL15, VEGFA
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
mitochondrial inner membrane 2 CKMT2, PRODH
Cytoplasm, cytosol 1 IDO1
Lysosome 3 IL4I1, MTOR, TYR
acrosomal vesicle 1 IL4I1
endosome 2 IL15, STEAP1
plasma membrane 2 PTEN, STEAP1
Membrane 6 ALDH3A2, DLK1, MAOA, MTOR, STEAP1, VEGFA
apical plasma membrane 1 PTEN
extracellular exosome 3 ALDH2, ELANE, PMP2
Lysosome membrane 1 MTOR
endoplasmic reticulum 1 VEGFA
extracellular space 6 ARG1, DLK1, ELANE, IL15, PRSS29P, VEGFA
perinuclear region of cytoplasm 1 TYR
adherens junction 1 VEGFA
mitochondrion 4 ALDH2, CKMT2, MAOA, PRODH
intracellular membrane-bounded organelle 3 ALDH3A2, PRODH, TYR
Microsome membrane 2 ALDH3A2, MTOR
postsynaptic density 1 PTEN
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 TYR
Secreted 4 CNDP1, IL4I1, PRSS29P, VEGFA
extracellular region 7 ARG1, CNDP1, ELANE, IL15, IL4I1, PTEN, VEGFA
cytoplasmic side of plasma membrane 1 PTEN
Mitochondrion outer membrane 2 MAOA, MTOR
Single-pass membrane protein 3 ALDH3A2, DLK1, MAOA
mitochondrial outer membrane 2 MAOA, MTOR
Mitochondrion matrix 1 ALDH2
mitochondrial matrix 2 ALDH2, PRODH
Secreted, extracellular space, extracellular matrix 1 VEGFA
dendritic spine 1 PTEN
Melanosome membrane 1 TYR
cell-cell junction 1 STEAP1
Golgi-associated vesicle 1 TYR
extracellular matrix 1 VEGFA
Peroxisome 1 ALDH3A2
peroxisomal membrane 1 ALDH3A2
Cell projection, dendritic spine 1 PTEN
Nucleus, PML body 2 MTOR, PTEN
PML body 2 MTOR, PTEN
collagen-containing extracellular matrix 1 ELANE
secretory granule 2 ELANE, VEGFA
nuclear speck 1 IL15
Cell projection, neuron projection 1 PTEN
neuron projection 1 PTEN
stereocilium bundle 1 IDO1
cell projection 1 PTEN
Cytoplasmic vesicle, secretory vesicle, acrosome 1 IL4I1
sperm midpiece 1 IL4I1
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
Melanosome 1 TYR
myelin sheath 1 PMP2
transcription repressor complex 1 ELANE
platelet alpha granule lumen 1 VEGFA
specific granule lumen 2 ARG1, ELANE
Schmidt-Lanterman incisure 1 PTEN
azurophil granule lumen 2 ARG1, ELANE
immunological synapse 1 IL4I1
Single-pass type IV membrane protein 1 MAOA
ribonucleoprotein complex 1 RBMS1
Cytoplasmic vesicle, phagosome 2 ELANE, MTOR
myelin sheath adaxonal region 1 PTEN
[Isoform alpha]: Secreted 1 PTEN
smooth muscle contractile fiber 1 IDO1
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA


文献列表

  • Dorottya Nagy-Szakal, Dinesh K Barupal, Bohyun Lee, Xiaoyu Che, Brent L Williams, Ellie J R Kahn, Joy E Ukaigwe, Lucinda Bateman, Nancy G Klimas, Anthony L Komaroff, Susan Levine, Jose G Montoya, Daniel L Peterson, Bruce Levin, Mady Hornig, Oliver Fiehn, W Ian Lipkin. Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics. Scientific reports. 2018 07; 8(1):10056. doi: 10.1038/s41598-018-28477-9. [PMID: 29968805]
  • Yeo Ul Cho, Deokjong Lee, Jung-Eun Lee, Kyoung Heon Kim, Do Yup Lee, Young-Chul Jung. Exploratory metabolomics of biomarker identification for the internet gaming disorder in young Korean males. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2017 Jul; 1057(?):24-31. doi: 10.1016/j.jchromb.2017.04.046. [PMID: 28482325]
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  • Guidong Liu, Xiaochang Dong, Leichao Liu, Lishu Wu, Shu'ang Peng, Cuncang Jiang. Metabolic profiling reveals altered pattern of central metabolism in navel orange plants as a result of boron deficiency. Physiologia plantarum. 2015 Apr; 153(4):513-24. doi: 10.1111/ppl.12279. [PMID: 25212059]
  • Evagelia C Laiakis, Gerard A J Morris, Albert J Fornace, Stephen R C Howie. Metabolomic analysis in severe childhood pneumonia in the Gambia, West Africa: findings from a pilot study. PloS one. 2010 Sep; 5(9):. doi: 10.1371/journal.pone.0012655. [PMID: 20844590]
  • Atanu Biswas, Brajendra K Sharma, Kenneth M Doll, Sevim Z Erhan, Julious L Willett, H N Cheng. Synthesis of an amine-oleate derivative using an ionic liquid catalyst. Journal of agricultural and food chemistry. 2009 Sep; 57(18):8136-41. doi: 10.1021/jf901401s. [PMID: 19719124]
  • Keisuke Kagami, Kenji Onda, Kitaro Oka, Toshihiko Hirano. Suppression of blood lipid concentrations by volatile Maillard reaction products. Nutrition (Burbank, Los Angeles County, Calif.). 2008 Nov; 24(11-12):1159-66. doi: 10.1016/j.nut.2008.05.010. [PMID: 18586457]
  • Zhen-Jian Lin, Xiao-Ming Lu, Tian-Jiao Zhu, Yu-Chun Fang, Qian-Qun Gu, Weiming Zhu. GPR12 selections of the metabolites from an endophytic Streptomyces sp. associated with Cistanches deserticola. Archives of pharmacal research. 2008 Sep; 31(9):1108-14. doi: 10.1007/s12272-001-1276-4. [PMID: 18806952]
  • Tim Sparey, Pravien Abeywickrema, Sarah Almond, Nick Brandon, Noel Byrne, Alister Campbell, Pete H Hutson, Marlene Jacobson, Brian Jones, Sanjeev Munshi, Danette Pascarella, Andrew Pike, G Sridhar Prasad, Nancy Sachs, Melanie Sakatis, Vinod Sardana, Shankar Venkatraman, Mary Beth Young. The discovery of fused pyrrole carboxylic acids as novel, potent D-amino acid oxidase (DAO) inhibitors. Bioorganic & medicinal chemistry letters. 2008 Jun; 18(11):3386-91. doi: 10.1016/j.bmcl.2008.04.020. [PMID: 18455394]
  • M O Lederer, M Baumann. Formation of a phospholipid-linked pyrrolecarbaldehyde from model reactions of D-glucose and 3-deoxyglucosone with phosphatidyl ethanolamine. Bioorganic & medicinal chemistry. 2000 Jan; 8(1):115-21. doi: 10.1016/s0968-0896(99)00264-3. [PMID: 10968270]
  • M Wajner, C M Wannmacher, P Purkiss. High urinary excretion of N-(pyrrole-2-carboxyl) glycine in type II hyperprolinemia. Clinical genetics. 1990 Jun; 37(6):485-9. doi: 10.1111/j.1399-0004.1990.tb03535.x. [PMID: 2383933]
  • J H Dreisbach, A Veca. Rapid method for the analysis of urinary pyrrole-2-carboxylic acid using reversed-phase high-performance liquid chromatography. Journal of chromatography. 1986 Oct; 382(?):280-3. doi: 10.1016/s0378-4347(00)83530-6. [PMID: 3782395]
  • E Svojtková, Z Deyl, J Andrlíková. Decrease in pyrrole-2-carboxylic acid excretion during lung cancer disease. Neoplasma. 1982; 29(5):625-9. doi: . [PMID: 7177252]
  • G B GERBER, K R TRAELNES, D WOOD, K I ALTMAN. THE QUANTITATIVE DETERMINATION OF PYRROLE-2-CARBOXYLIC ACID IN URINE. Clinica chimica acta; international journal of clinical chemistry. 1964 Feb; 9(?):185-7. doi: 10.1016/0009-8981(64)90015-4. [PMID: 14122509]
  • K KONNO, K R TRAELNES, K I ALTMAN. THE EFFECT OF WHOLE- AND PARTIAL-BODY X-IRRADIATION ON THE METABOLISM OF COLLAGEN IN POLYETHYLENE SPONGES AND THE URINARY EXCRETION OF PYRROLE-2-CARBOXYLIC ACID. International journal of radiation biology and related studies in physics, chemistry, and medicine. 1964; 8(?):367-72. doi: 10.1080/09553006414550431. [PMID: 14274308]