FADH (BioDeep_00000004676)

 

Secondary id: BioDeep_00001869023

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

化学式: C27H35N9O15P2 (787.1728)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(otcml) 7.39%

分子结构信息

SMILES: CC1=CC2=C(C=C1C)N(C3=C(N2)C(=O)NC(=O)N3)CC(C(C(COP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)O
InChI: InChI=1S/C27H35N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,32,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H2,33,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1

描述信息

Fadh2, also known as 1,5-dihydro-fad or dihydroflavine-adenine dinucleotide, is a member of the class of compounds known as flavin nucleotides. Flavin nucleotides are nucleotides containing a flavin moiety. Flavin is a compound that contains the tricyclic isoalloxazine ring system, which bears 2 oxo groups at the 2- and 4-positions. Fadh2 is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Fadh2 can be found in a number of food items such as soft-necked garlic, fruits, winter squash, and black cabbage, which makes fadh2 a potential biomarker for the consumption of these food products. Fadh2 exists in all living species, ranging from bacteria to humans. In humans, fadh2 is involved in several metabolic pathways, some of which include the oncogenic action of fumarate, the oncogenic action of 2-hydroxyglutarate, citric acid cycle, and congenital lactic acidosis. Fadh2 is also involved in several metabolic disorders, some of which include 2-ketoglutarate dehydrogenase complex deficiency, the oncogenic action of d-2-hydroxyglutarate in hydroxygluaricaciduria, the oncogenic action of l-2-hydroxyglutarate in hydroxygluaricaciduria, and pyruvate dehydrogenase deficiency (E2).
FADH is the reduced form of flavin adenine dinucleotide (FAD). FAD is synthesized from riboflavin and two molecules of ATP. Riboflavin is phosphorylated by ATP to give riboflavin 5-phosphate (FMN). FAD is then formed from FMN by the transfer of an AMP moiety from a second molecule of ATP. FADH is generated in each round of fatty acid oxidation, and the fatty acyl chain is shortened by two carbon atoms as a result of these reactions; because oxidation is on the beta carbon, this series of reactions is called the beta-oxidation pathway. In the citric acid cycle, FADH is involved in the harvesting of high-energy electrons from carbon fuels; the citric acid cycle itself neither generates a large amount of ATP nor includes oxygen as a reactant. Instead, the citric acid cycle removes electrons from acetyl CoA and uses these electrons to form FADH.

同义名列表

23 个代谢物同义名

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-1H,2H,3H,4H,5H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid; Adenosine 5-{3-[D-ribo-5-(7,8-dimethyl-2,4-dioxo-1,2,3,4,5,10-tetrahydrobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] dihydrogen diphosphate}; Adenosine 5-(trihydrogen pyrophosphate), 5->5-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine; Adenosine 5-(trihydrogen pyrophosphate), 5-5-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine; Adenosine pyrophosphate, 5->5-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine; Adenosine pyrophosphate, 5-5-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine; Adenosine pyrophosphate 5-5-ester with 5,10-dihydro-7,8-dimethyl-10-(D-ribo-2,3,4,5-tetrahydroxypentyl)alloxazine; 1,5-Dihydro-riboflavin 5-(trihydrogen diphosphate) p->5-ester with adenosine; Benzo[GR]pteridine riboflavin 5-(trihydrogen diphosphate) deriv; Benzo[g]pteridine riboflavin 5-(trihydrogen diphosphate) deriv; Adenosine 5-(trihydrogen pyrophosphate); Flavin adenine dinucleotide (reduced); 1,5-Dihydro-p-5-ester with adenosine; Reduced flavine adenine dinucleotide; DIHYDROFLAVINE-adenine dinucleotide; Flavin adenine dinucleotide reduced; 1,5-Dihydro-fad; SCHEMBL4371447; Dihydro-fad; fadh(.); FADH2; FADH; FDA



数据库引用编号

14 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(1)

BioCyc(1)

PlantCyc(0)

代谢反应

721 个相关的代谢反应过程信息。

Reactome(87)

BioCyc(7)

WikiPathways(0)

Plant Reactome(579)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(48)

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 6 BLVRB, CRY1, CRY2, NQO1, TXN, XDH
Peripheral membrane protein 3 FDXR, HSD17B6, SDHA
Nucleus 5 CRY1, CRY2, LIG4, NQO1, TXN
cytosol 6 BLVRB, CRY2, GSR, NQO1, TXN, XDH
dendrite 2 C4A, NQO1
nucleoplasm 3 BLVRB, LIG4, TXN
Cell projection, axon 1 C4A
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 2 MT-CYB, SLC9C1
Synapse 2 C4A, NQO1
Golgi membrane 1 INS
mitochondrial inner membrane 5 ATP5ME, FDXR, MT-CYB, SDHA, SQOR
neuronal cell body 2 C4A, NQO1
Cytoplasm, cytosol 1 NQO1
plasma membrane 3 BLVRB, C4A, SLC9C1
Membrane 4 EPHX4, MT-CYB, NQO1, SLC9C1
axon 1 C4A
extracellular exosome 4 BLVRB, C4A, GSR, TXN
Lumenal side 1 HSD17B6
endoplasmic reticulum 1 HSD17B6
extracellular space 3 C4A, INS, XDH
mitochondrion 10 ATP5ME, CRY1, CRY2, ETFA, ETFB, FDXR, GSR, MT-CYB, SDHA, SQOR
intracellular membrane-bounded organelle 3 BLVRB, HSD17B6, LIG4
Microsome membrane 1 HSD17B6
Secreted 3 C4A, INS, TXN
extracellular region 4 C4A, CRY2, INS, TXN
Mitochondrion matrix 2 ETFA, ETFB
mitochondrial matrix 5 ETFA, ETFB, FDXR, GSR, SDHA
motile cilium 1 SLC9C1
external side of plasma membrane 1 GSR
nucleolus 1 SDHA
Single-pass type II membrane protein 1 EPHX4
Mitochondrion inner membrane 3 FDXR, MT-CYB, SDHA
Matrix side 1 SDHA
Peroxisome 1 XDH
sarcoplasmic reticulum 1 XDH
nuclear speck 1 CRY2
chromosome, telomeric region 1 LIG4
blood microparticle 1 C4A
endosome lumen 1 INS
Cell projection, cilium, flagellum membrane 1 SLC9C1
Cell projection, dendrite 1 C4A
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 C4A, INS
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
respiratory chain complex II (succinate dehydrogenase) 1 SDHA
respiratory chain complex III 1 MT-CYB
Cry-Per complex 1 CRY2
condensed chromosome 1 LIG4
proton-transporting ATP synthase complex 1 ATP5ME
proton-transporting ATP synthase complex, coupling factor F(o) 1 ATP5ME
DNA-dependent protein kinase-DNA ligase 4 complex 1 LIG4
nonhomologous end joining complex 1 LIG4
electron transfer flavoprotein complex 2 ETFA, ETFB
DNA ligase IV complex 1 LIG4


文献列表

  • Cen Zhang, Guowen Zhang, Yijing Liao, Deming Gong. Myricetin inhibits the generation of superoxide anion by reduced form of xanthine oxidase. Food chemistry. 2017 Apr; 221(?):1569-1577. doi: 10.1016/j.foodchem.2016.10.136. [PMID: 27979130]
  • Verónica I Dumit, Timm Essigke, Néstor Cortez, G Matthias Ullmann. Mechanistic insights into ferredoxin-NADP(H) reductase catalysis involving the conserved glutamate in the active site. Journal of molecular biology. 2010 Apr; 397(3):814-25. doi: 10.1016/j.jmb.2010.01.063. [PMID: 20132825]
  • Alena Liavonchanka, Markus G Rudolph, Kai Tittmann, Mats Hamberg, Ivo Feussner. On the mechanism of a polyunsaturated fatty acid double bond isomerase from Propionibacterium acnes. The Journal of biological chemistry. 2009 Mar; 284(12):8005-12. doi: 10.1074/jbc.m809060200. [PMID: 19164287]
  • Pavinee Kurdrid, Sanjukta Subudhi, Supapon Cheevadhanarak, Morakot Tanticharoen, Apiradee Hongsthong. Effect of two intermediate electron donors, NADPH and FADH(2), on Spirulina Delta (6)-desaturase co-expressed with two different immediate electron donors, cytochrome b (5) and ferredoxin, in Escherichia coli. Molecular biology reports. 2007 Dec; 34(4):261-6. doi: 10.1007/s11033-006-9040-8. [PMID: 17160624]
  • George Emílio Sampaio Barreto, Gleide Souza dos Santos, Eryvaldo Sócrates Tabosa Egito, Ramon dos Santos El-Bachá. Catechol inhibits FADH2-linked respiration in rat liver mitochondrial fraction. Acta cirurgica brasileira. 2005; 20 Suppl 1(?):72-7. doi: 10.1590/s0102-86502005000700008. [PMID: 16186974]
  • Jaap van Milgen. Modeling biochemical aspects of energy metabolism in mammals. The Journal of nutrition. 2002 Oct; 132(10):3195-202. doi: 10.1093/jn/131.10.3195. [PMID: 12368418]
  • W N Kuo, R N Kanadia, V P Shanbhag, R Toro. Denitration of peroxynitrite-treated proteins by 'protein nitratases' from rat brain and heart. Molecular and cellular biochemistry. 1999 Nov; 201(1-2):11-6. doi: 10.1023/a:1007024126947. [PMID: 10630617]
  • M W Surber, S Maloy. Regulation of flavin dehydrogenase compartmentalization: requirements for PutA-membrane association in Salmonella typhimurium. Biochimica et biophysica acta. 1999 Sep; 1421(1):5-18. doi: 10.1016/s0005-2736(99)00104-2. [PMID: 10561467]