Glyceric acid 1,3-biphosphate (BioDeep_00000004399)

 

Secondary id: BioDeep_00001869112

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoic acid

化学式: C3H8O10P2 (265.9593)
中文名称: 4-氨基-N,N-二丙基苯磺酰胺
谱图信息: 最多检出来源 Homo sapiens(blood) 27.6%

分子结构信息

SMILES: C(C(C(=O)OP(=O)(O)O)O)OP(=O)(O)O
InChI: InChI=1S/C3H8O10P2/c4-2(1-12-14(6,7)8)3(5)13-15(9,10)11/h2,4H,1H2,(H2,6,7,8)(H2,9,10,11)

描述信息

Glyceric acid 1,3-biphosphate (CAS: 1981-49-3), also known as 1,3-bisphosphoglycerate (1,3BPG) or PGAP, is a 3-carbon organic molecule present in most, if not all living creatures. It primarily exists as a metabolic intermediate in glycolysis during respiration. 1,3BPG has been recognized as regulatory signal implicated in the control of metabolism, oxygen affinity of red cells, and other cellular functions. 1,3BPG concentration in erythrocytes changes in a number of pathological conditions, such as inherited phosphoglycerate kinase deficiency in erythrocytes (involved in the synthesis and breakdown of 1,3BPG) (PMID: 3555887). Glyceric acid 1,3-biphosphate is phosphorylated at the number 1 and 3 carbons. The result of this phosphorylation gives 1,3BPG important biological properties such as the ability to phosphorylate ADP to form the energy storage molecule ATP (Wikipedia).
3-phospho-d-glyceroyl phosphate, also known as 1,3-bisphospho-D-glycerate or D-glycerate 1,3-diphosphate, is a member of the class of compounds known as acyl monophosphates. Acyl monophosphates are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl. 3-phospho-d-glyceroyl phosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 3-phospho-d-glyceroyl phosphate can be found in a number of food items such as tamarind, narrowleaf cattail, mustard spinach, and cereals and cereal products, which makes 3-phospho-d-glyceroyl phosphate a potential biomarker for the consumption of these food products. 3-phospho-d-glyceroyl phosphate exists in E.coli (prokaryote) and yeast (eukaryote).

同义名列表

39 个代谢物同义名

(R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoic acid; (R)-2-Hydroxy-3-(phosphonooxy)-1-monoanhydride with phosphoric propanoate; {[(2R)-2-hydroxy-3-(phosphonooxy)propanoyl]oxy}phosphonic acid; 3-Phospho-D-glyceroyl dihydrogen phosphoric acid; 3-phospho-D-glyceroyl dihydrogen phosphate; 3-Phospho-D-glyceroyl phosphoric acid; D-Glyceric acid 1,3-diphosphoric acid; Glyceric acid 1,3-biphosphoric acid; 3-Phosphonato-D-glyceroyl phosphate; D-Glyceric acid 1,3-bisphosphate; 3-Phosphonatoglyceroyl phosphate; 3-Phospho-D-glyceroyl phosphate; D-Glyceric acid 1,3-biphosphate; D-Glyceric acid 1,3-diphosphate; 3-Phospho-D-glyceroyl-phosphate; 1,3-Bisphospho-D-glyceric acid; Glyceric acid 1,3-bisphosphate; glyceric acid 1,3-biphosphate; Glyceric acid 1,3-diphosphate; 3-Phosphoglyceroyl phosphate; 3-Phosphoglyceroyl-phosphate; D-Glycerate 1,3-bisphosphate; D-Glycerate 1,3-biphosphate; D-Glycerate 1,3-diphosphate; 1,3-Bisphosphoglyceric acid; 1,3-Bisphospho-D-glycerate; Glycerate 1,3-bisphosphate; 1,3-Diphosphoglyceric acid; Glycerate 1,3-biphosphate; Glycerate 1,3-diphosphate; 1,3-Bisphosphoglycerate; 1,3-Diphosphoglycerate; 1,3-Biphosphoglycerate; 3-Phosphoglyceroyl-p; Phosphoglyceroyl-p; 3-p-Glyceroyl-p; p-Glyceroyl-p; DPG; 3-Phospho-D-glyceroyl phosphate



数据库引用编号

20 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(5)

PlantCyc(0)

代谢反应

544 个相关的代谢反应过程信息。

Reactome(15)

BioCyc(16)

WikiPathways(8)

Plant Reactome(404)

INOH(3)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(98)

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 12 AKR1B1, CAPNS1, GAPDH, GAPDHS, GPI, PGAM1, PGK2, PGM2, PIK3CA, PKM, PRKG1, TXN
Endosome membrane 1 TF
Endoplasmic reticulum membrane 1 CYP1A2
Nucleus 5 GAPDH, GAPDHS, PGK2, PKM, TXN
cytosol 15 AKR1B1, CAPNS1, GAPDH, GAPDHS, GPI, PGAM1, PGK1, PGK2, PGM2, PGM2L1, PHGDH, PIK3CA, PKM, PRKG1, TXN
nucleoplasm 3 AKR1B1, PRKG1, TXN
Cell membrane 1 CAPNS1
lamellipodium 1 PIK3CA
Synapse 1 ALDH5A1
cell surface 2 EPO, TF
Golgi apparatus 1 PRKG1
sarcolemma 1 PRKG1
Cytoplasm, cytosol 3 GAPDH, PGM2, PGM2L1
acrosomal vesicle 1 PRKG1
plasma membrane 5 CAPNS1, GAPDH, PIK3CA, PRKG1, TF
Membrane 6 CAPNS1, DGCR2, GAPDH, GPI, PGAM1, PGK1
apical plasma membrane 1 TF
extracellular exosome 13 AKR1B1, CAPNS1, EPO, GAPDH, GPI, PGAM1, PGK1, PGK2, PGM2, PHGDH, PKM, TF, TXN
extracellular space 5 AKR1B1, EPO, GPI, PGK1, TF
perinuclear region of cytoplasm 3 GAPDH, PIK3CA, TF
intercalated disc 1 PIK3CA
mitochondrion 3 AKR1B1, ALDH5A1, PKM
intracellular membrane-bounded organelle 2 CYP1A2, GAPDH
Microsome membrane 1 CYP1A2
Secreted 4 EPO, GPI, TF, TXN
extracellular region 7 EPO, GPI, PGAM1, PGM2, PKM, TF, TXN
basal part of cell 1 TF
mitochondrial matrix 1 ALDH5A1
ciliary membrane 1 GPI
nuclear membrane 1 GAPDH
Extracellular vesicle 1 PKM
cytoplasmic vesicle 1 TF
microtubule cytoskeleton 1 GAPDH
Early endosome 1 TF
clathrin-coated pit 1 TF
recycling endosome 1 TF
vesicle 3 GAPDH, PKM, TF
Cytoplasm, perinuclear region 1 GAPDH
Membrane raft 1 PGK1
Cytoplasm, cytoskeleton 1 GAPDH
collagen-containing extracellular matrix 1 PKM
Late endosome 1 TF
cilium 1 PKM
cytoskeleton 1 GAPDH
blood microparticle 1 TF
Endomembrane system 1 CAPNS1
Lipid droplet 1 GAPDH
cell body 1 EPO
basal plasma membrane 1 TF
ficolin-1-rich granule lumen 4 GPI, PGAM1, PGM2, PKM
secretory granule lumen 6 EPO, GPI, PGAM1, PGM2, PKM, TF
HFE-transferrin receptor complex 1 TF
endoplasmic reticulum lumen 1 TF
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
endocytic vesicle 1 TF
clathrin-coated endocytic vesicle membrane 1 TF
ribonucleoprotein complex 1 GAPDH
Rough endoplasmic reticulum 1 PKM
GAIT complex 1 GAPDH
sperm fibrous sheath 1 PGK2
vesicle coat 1 TF
calpain complex 1 CAPNS1
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
dense body 1 TF


文献列表

  • Yiyi Gong, Panpan Zhang, Zheng Liu, Jieqiong Li, Hui Lu, Yujie Wang, Bintao Qiu, Mu Wang, Yunyun Fei, Hua Chen, Linyi Peng, Jing Li, Jiaxin Zhou, Qun Shi, Xuan Zhang, Min Shen, Xiaofeng Zeng, Fengchun Zhang, Wen Zhang. UPLC-MS based plasma metabolomics and lipidomics reveal alterations associated with IgG4-related disease. Rheumatology (Oxford, England). 2021 07; 60(7):3252-3261. doi: 10.1093/rheumatology/keaa775. [PMID: 33341881]
  • Carolina Gimiliani Lembke, Milton Yutaka Nishiyama, Paloma Mieko Sato, Rodrigo Fandiño de Andrade, Glaucia Mendes Souza. Identification of sense and antisense transcripts regulated by drought in sugarcane. Plant molecular biology. 2012 Jul; 79(4-5):461-77. doi: 10.1007/s11103-012-9922-1. [PMID: 22610347]
  • Wei Guo, Li-fang Zou, Yu-rong Li, Yi-ping Cui, Zhi-yuan Ji, Lu-lu Cai, Hua-song Zou, William C Hutchins, Ching-hong Yang, Gong-you Chen. Fructose-bisphophate aldolase exhibits functional roles between carbon metabolism and the hrp system in rice pathogen Xanthomonas oryzae pv. oryzicola. PloS one. 2012; 7(2):e31855. doi: 10.1371/journal.pone.0031855. [PMID: 22384086]
  • Carolin A Kolmeder, Mark de Been, Janne Nikkilä, Ilja Ritamo, Jaana Mättö, Leena Valmu, Jarkko Salojärvi, Airi Palva, Anne Salonen, Willem M de Vos. Comparative metaproteomics and diversity analysis of human intestinal microbiota testifies for its temporal stability and expression of core functions. PloS one. 2012; 7(1):e29913. doi: 10.1371/journal.pone.0029913. [PMID: 22279554]
  • Huawu Jiang, Pingzhi Wu, Sheng Zhang, Chi Song, Yaping Chen, Meiru Li, Yongxia Jia, Xiaohua Fang, Fan Chen, Guojiang Wu. Global analysis of gene expression profiles in developing physic nut (Jatropha curcas L.) seeds. PloS one. 2012; 7(5):e36522. doi: 10.1371/journal.pone.0036522. [PMID: 22574177]
  • Liezel M Gouws, Eileen Botes, Anna J Wiese, Sandra Trenkamp, Ivone Torres-Jerez, Yuhong Tang, Paul N Hills, Björn Usadel, James R Lloyd, Alisdair R Fernie, Jens Kossmann, Margaretha J van der Merwe. The plant growth promoting substance, lumichrome, mimics starch, and ethylene-associated symbiotic responses in lotus and tomato roots. Frontiers in plant science. 2012; 3(?):120. doi: 10.3389/fpls.2012.00120. [PMID: 22701462]
  • Yoichi Shimoda, Junkyu Han, Kiyokazu Kawada, Abderrazak Smaoui, Hiroko Isoda. Metabolomics analysis of Cistus monspeliensis leaf extract on energy metabolism activation in human intestinal cells. Journal of biomedicine & biotechnology. 2012; 2012(?):428514. doi: 10.1155/2012/428514. [PMID: 22523469]
  • William J Chirico. Protein release through nonlethal oncotic pores as an alternative nonclassical secretory pathway. BMC cell biology. 2011 Oct; 12(?):46. doi: 10.1186/1471-2121-12-46. [PMID: 22008609]
  • Zhixin Zhao, Sarah M Assmann. The glycolytic enzyme, phosphoglycerate mutase, has critical roles in stomatal movement, vegetative growth, and pollen production in Arabidopsis thaliana. Journal of experimental botany. 2011 Oct; 62(14):5179-89. doi: 10.1093/jxb/err223. [PMID: 21813794]
  • Baolei Jia, Le Thuy Linh, Sangmin Lee, Bang Phuong Pham, Jinliang Liu, Hongyu Pan, Shihong Zhang, Gang-Won Cheong. Biochemical characterization of glyceraldehyde-3-phosphate dehydrogenase from Thermococcus kodakarensis KOD1. Extremophiles : life under extreme conditions. 2011 May; 15(3):337-46. doi: 10.1007/s00792-011-0365-4. [PMID: 21409597]
  • Hong Lin, Binghai Lou, Jonathan M Glynn, Harshavardhan Doddapaneni, Edwin L Civerolo, Chuanwu Chen, Yongping Duan, Lijuan Zhou, Cheryl M Vahling. The complete genome sequence of 'Candidatus Liberibacter solanacearum', the bacterium associated with potato zebra chip disease. PloS one. 2011 Apr; 6(4):e19135. doi: 10.1371/journal.pone.0019135. [PMID: 21552483]
  • Ziru Li, Ellen A Ratliff, Thomas D Sharkey. Effect of temperature on postillumination isoprene emission in oak and poplar. Plant physiology. 2011 Feb; 155(2):1037-46. doi: 10.1104/pp.110.167551. [PMID: 21177471]
  • Jesús Muñoz-Bertomeu, María Angeles Bermúdez, Juan Segura, Roc Ros. Arabidopsis plants deficient in plastidial glyceraldehyde-3-phosphate dehydrogenase show alterations in abscisic acid (ABA) signal transduction: interaction between ABA and primary metabolism. Journal of experimental botany. 2011 Jan; 62(3):1229-39. doi: 10.1093/jxb/erq353. [PMID: 21068209]
  • Hong Jin, Shivangi Agarwal, Shivani Agarwal, Vijay Pancholi. Surface export of GAPDH/SDH, a glycolytic enzyme, is essential for Streptococcus pyogenes virulence. mBio. 2011; 2(3):e00068-11. doi: 10.1128/mbio.00068-11. [PMID: 21628503]
  • Ricardo Nilo, Carlos Saffie, Kathryn Lilley, Ricardo Baeza-Yates, Verónica Cambiazo, Reinaldo Campos-Vargas, Mauricio González, Lee A Meisel, Julio Retamales, Herman Silva, Ariel Orellana. Proteomic analysis of peach fruit mesocarp softening and chilling injury using difference gel electrophoresis (DIGE). BMC genomics. 2010 Jan; 11(?):43. doi: 10.1186/1471-2164-11-43. [PMID: 20082721]
  • Aaron K Livingston, Jeffrey A Cruz, Kaori Kohzuma, Amit Dhingra, David M Kramer. An Arabidopsis mutant with high cyclic electron flow around photosystem I (hcef) involving the NADPH dehydrogenase complex. The Plant cell. 2010 Jan; 22(1):221-33. doi: 10.1105/tpc.109.071084. [PMID: 20081115]
  • Jesús Muñoz-Bertomeu, Borja Cascales-Miñana, Manuel Alaiz, Juan Segura, Roc Ros. A critical role of plastidial glycolytic glyceraldehyde-3-phosphate dehydrogenase in the control of plant metabolism and development. Plant signaling & behavior. 2010 Jan; 5(1):67-9. doi: 10.4161/psb.5.1.10200. [PMID: 20592814]
  • Jesús Muñoz-Bertomeu, Borja Cascales-Miñana, Jose Miguel Mulet, Edurne Baroja-Fernández, Javier Pozueta-Romero, Josef M Kuhn, Juan Segura, Roc Ros. Plastidial glyceraldehyde-3-phosphate dehydrogenase deficiency leads to altered root development and affects the sugar and amino acid balance in Arabidopsis. Plant physiology. 2009 Oct; 151(2):541-58. doi: 10.1104/pp.109.143701. [PMID: 19675149]
  • Sebastián P Rius, Paula Casati, Alberto A Iglesias, Diego F Gomez-Casati. Characterization of Arabidopsis lines deficient in GAPC-1, a cytosolic NAD-dependent glyceraldehyde-3-phosphate dehydrogenase. Plant physiology. 2008 Nov; 148(3):1655-67. doi: 10.1104/pp.108.128769. [PMID: 18820081]
  • Sebastien Pomel, Flora C Y Luk, Con J M Beckers. Host cell egress and invasion induce marked relocations of glycolytic enzymes in Toxoplasma gondii tachyzoites. PLoS pathogens. 2008 Oct; 4(10):e1000188. doi: 10.1371/journal.ppat.1000188. [PMID: 18949028]
  • Ivi C Tsantili, M Nazmul Karim, Maria I Klapa. Quantifying the metabolic capabilities of engineered Zymomonas mobilis using linear programming analysis. Microbial cell factories. 2007 Mar; 6(?):8. doi: 10.1186/1475-2859-6-8. [PMID: 17349037]
  • Mirko Zaffagnini, Laure Michelet, Christophe Marchand, Francesca Sparla, Paulette Decottignies, Pierre Le Maréchal, Myroslawa Miginiac-Maslow, Graham Noctor, Paolo Trost, Stéphane D Lemaire. The thioredoxin-independent isoform of chloroplastic glyceraldehyde-3-phosphate dehydrogenase is selectively regulated by glutathionylation. The FEBS journal. 2007 Jan; 274(1):212-26. doi: 10.1111/j.1742-4658.2006.05577.x. [PMID: 17140414]
  • Sergio Grimbs, Joachim Selbig, Sascha Bulik, Hermann-Georg Holzhütter, Ralf Steuer. The stability and robustness of metabolic states: identifying stabilizing sites in metabolic networks. Molecular systems biology. 2007; 3(?):146. doi: 10.1038/msb4100186. [PMID: 18004279]
  • Sandrine Lebreton, Simona Andreescu, Emmanuelle Graciet, Brigitte Gontero. Mapping of the interaction site of CP12 with glyceraldehyde-3-phosphate dehydrogenase from Chlamydomonas reinhardtii. Functional consequences for glyceraldehyde-3-phosphate dehydrogenase. The FEBS journal. 2006 Jul; 273(14):3358-69. doi: 10.1111/j.1742-4658.2006.05342.x. [PMID: 16803460]
  • Francesca Sparla, Mirko Zaffagnini, Norbert Wedel, Renate Scheibe, Paolo Pupillo, Paolo Trost. Regulation of photosynthetic GAPDH dissected by mutants. Plant physiology. 2005 Aug; 138(4):2210-9. doi: 10.1104/pp.105.062117. [PMID: 16055685]
  • Emmanuelle Graciet, Sandrine Lebreton, Jean-Michel Camadro, Brigitte Gontero. Characterization of native and recombinant A4 glyceraldehyde 3-phosphate dehydrogenase. Kinetic evidence for confromation changes upon association with the small protein CP12. European journal of biochemistry. 2003 Jan; 270(1):129-36. doi: 10.1046/j.1432-1033.2003.03372.x. [PMID: 12492483]
  • Renate Scheibe, Norbert Wedel, Susanne Vetter, Vera Emmerlich, Sonja-Manuela Sauermann. Co-existence of two regulatory NADP-glyceraldehyde 3-P dehydrogenase complexes in higher plant chloroplasts. European journal of biochemistry. 2002 Nov; 269(22):5617-24. doi: 10.1046/j.1432-1033.2002.03269.x. [PMID: 12423361]
  • . . . . doi: . [PMID: 24862258]