Dihydroneopterin triphosphate (BioDeep_00000005694)

 

Secondary id: BioDeep_00000604808

human metabolite Endogenous natural product


代谢物信息卡片


{[({[(2R,3S)-3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid

化学式: C9H16N5O13P3 (494.9957)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(plant) 9.76%

分子结构信息

SMILES: C1C(=NC2=C(N1)N=C(NC2=O)N)C(C(COP(=O)(O)OP(=O)(O)OP(=O)(O)O)O)O
InChI: InChI=1S/C9H16N5O13P3/c10-9-13-7-5(8(17)14-9)12-3(1-11-7)6(16)4(15)2-25-29(21,22)27-30(23,24)26-28(18,19)20/h4,6,15-16H,1-2H2,(H,21,22)(H,23,24)(H2,18,19,20)(H4,10,11,13,14,17)/t4-,6+/m1/s1

描述信息

The biosynthesis of tetrahydrobiopterin (BH4) from dihydroneopterin triphosphate (NH2P3) was studied in human liver extract. The phosphate-eliminating enzyme (PEE) was purified approximately 750-fold. The conversion of NH2P3 to BH4 was catalyzed by this enzyme in the presence of partially purified sepiapterin reductase, Mg2+, and NADPH. The PEE is heat stable when heated at 80°C for 5 min. It has a molecular weight of 63 000 daltons. One possible intermediate 6-(1-hydroxy-2-oxopropyl)5,6,7,8-tetrahydropterin(2-oxo-tetrahydropte rin) was formed upon incubation of BH4 in the presence of sepiapterin reductase and NADP+ at pH 9.0. The reduction of this compound with NaBD4 yielded monodeutero-, threo-, and erythro-BH4; the deuterium was incorporated at the 2 position. This and the UV spectra were consistent with a 2-oxo-tetrahydropterin structure. Dihydrofolate reductase (DHFR) catalyzed the reduction of BH2 into BH4 and was found to be specific for the pro-R-NADPH side. The sepiapterin reductase catalyzed the transfer of the pro-S hydrogen of NADPH during the reduction of sepiapterin into BH2. In the presence of crude liver extracts, the conversion of NH2P3 into BH4 requires NADPH. Two deuterium atoms were incorporated from (4S-2H)NADHP in the 1 and 2 position of the BH4 side chain. The incorporation of one hydrogen from the solvent was found at position C(6). These results are consistent with the occurrence of an intramolecular redox exchange between the pteridine nucleus and the side chain and formation of 6-pyruvoyl-5,6,7,8-tetrahydropterin(tetrahydro-1-2-dioxopterin) as an intermediate (PMID: 3930838).
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同义名列表

16 个代谢物同义名

{[({[(2R,3S)-3-(2-amino-4-oxo-1,4,7,8-tetrahydropteridin-6-yl)-2,3-dihydroxypropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid; {[(2R,3S)-3-(2-amino-4-oxo-7,8-dihydro-1H-pteridin-6-yl)-2,3-dihydroxypropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxyphosphonic acid; 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphoric acid; 2-amino-4-Hydroxy-6-(erythro-1,2,3-trihydroxypropyl) dihydropteridine triphosphate; 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine triphosphate; 6-(L-Erythro-1,2-dihydroxypropyl 3-triphosphoric acid)-7,8-dihydropterin; 6-(L-Erythro-1,2-dihydroxy-3-triphosphooxypropyl)-7,8-dihydropterin; 6-(L-Erythro-1,2-dihydroxypropyl 3-triphosphate)-7,8-dihydropterin; 6-[(1S,2R)-1,2-Dihydroxy-3-triphosphooxypropyl]-7,8-dihydropterin; Dihydroneopterin triphosphate, (S-(r*,s*))-isomer; Dihydroneopterin triphosphoric acid; 7,8-Dihydroneopterin 3-triphosphate; 7,8-Dihydroneopterin triphosphate; dihydro-Neopterin triphosphate; Dihydroneopterin triphosphate; 27040-09-1



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(2)

PlantCyc(0)

代谢反应

275 个相关的代谢反应过程信息。

Reactome(12)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(1)

PlantCyc(232)

COVID-19 Disease Map(1)

PathBank(27)

PharmGKB(0)

11 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 10 BRAF, CMA1, DHFR, GCH1, GCHFR, KITLG, PRUNE2, SPR, TH, XDH
Endoplasmic reticulum membrane 1 CD4
Nucleus 4 BRAF, GCH1, GCHFR, TH
cytosol 9 BRAF, CMA1, DHFR, GCH1, GCHFR, PRUNE2, SPR, TH, XDH
dendrite 2 GCHFR, TH
nucleoplasm 3 GCH1, GCHFR, SPR
Cell membrane 3 BRAF, CD4, KITLG
lamellipodium 1 KITLG
Cell projection, axon 1 TH
glutamatergic synapse 2 BRAF, PRUNE2
postsynapse 1 BRAF
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Cytoplasm, cytosol 1 GCHFR
Presynapse 2 BRAF, PRUNE2
plasma membrane 4 BRAF, CD4, IFNLR1, KITLG
terminal bouton 1 TH
Membrane 3 IFNLR1, KITLG, PRUNE2
axon 1 TH
extracellular exosome 1 SPR
extracellular space 4 CMA1, IL2, KITLG, XDH
perinuclear region of cytoplasm 1 TH
mitochondrion 6 BRAF, DHFR, GCH1, SPR, SUOX, TH
protein-containing complex 1 GCH1
intracellular membrane-bounded organelle 2 BRAF, CMA1
filopodium 1 KITLG
Single-pass type I membrane protein 3 CD4, IFNLR1, KITLG
Secreted 2 IL2, KITLG
extracellular region 3 CMA1, IL2, KITLG
cytoplasmic side of plasma membrane 1 TH
mitochondrial matrix 1 SUOX
Nucleus membrane 1 GCHFR
nuclear membrane 2 GCH1, GCHFR
external side of plasma membrane 1 CD4
perikaryon 1 TH
cytoplasmic vesicle 2 GCH1, TH
Melanosome membrane 1 TH
Early endosome 1 CD4
Cell projection, lamellipodium 1 KITLG
Cytoplasm, perinuclear region 1 TH
Membrane raft 1 CD4
Cytoplasm, cytoskeleton 1 KITLG
Peroxisome 1 XDH
sarcoplasmic reticulum 1 XDH
Mitochondrion intermembrane space 1 SUOX
mitochondrial intermembrane space 1 SUOX
collagen-containing extracellular matrix 1 CMA1
secretory granule 1 CMA1
Cell projection, filopodium 1 KITLG
neuron projection 2 BRAF, TH
cytoskeleton 1 KITLG
cytoplasmic ribonucleoprotein granule 1 CMA1
Melanosome 1 GCHFR
cell body 1 BRAF
endoplasmic reticulum lumen 1 CD4
[Isoform 2]: Cytoplasm 1 KITLG
clathrin-coated endocytic vesicle membrane 1 CD4
T cell receptor complex 1 CD4
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
neuron projection terminus 1 GCH1
interleukin-28 receptor complex 1 IFNLR1


文献列表

  • Z Bellahsene, J L Dhondt, J P Farriaux. Guanosine triphosphate cyclohydrolase activity in rat tissues. The Biochemical journal. 1984 Jan; 217(1):59-65. doi: 10.1042/bj2170059. [PMID: 6696731]
  • S I Yoshioka, M Masada, T Yoshida, K Inoue, T Mizokami, M Akino. Synthesis of biopterin from dihydroneopterin triphosphate by rat tissues. Biochimica et biophysica acta. 1983 Apr; 756(3):279-85. doi: 10.1016/0304-4165(83)90336-7. [PMID: 6830857]
  • I Eto, K Fukushima, T Shiota. Enzymatic synthesis of biopterin from D-erythrodihydroneopterin triphosphate by extracts of kidneys from Syrian golden hamsters. The Journal of biological chemistry. 1976 Nov; 251(21):6505-12. doi: . [PMID: 10299]