Nicotinic acid adenine dinucleotide (BioDeep_00000004140)

 

Secondary id: BioDeep_00000231876, BioDeep_00001869051

natural product human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1lambda5-pyridin-1-ylium

化学式: [C21H27N6O15P2]+ (665.101)
中文名称:
谱图信息: 最多检出来源 Homo sapiens(otcml) 4.46%

分子结构信息

SMILES: C1=CC(=C[N+](=C1)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O)C(=O)O
InChI: InChI=1S/C21H26N6O15P2/c22-17-12-18(24-7-23-17)27(8-25-12)20-16(31)14(29)11(41-20)6-39-44(36,37)42-43(34,35)38-5-10-13(28)15(30)19(40-10)26-3-1-2-9(4-26)21(32)33/h1-4,7-8,10-11,13-16,19-20,28-31H,5-6H2,(H4-,22,23,24,32,33,34,35,36,37)/p+1/t10-,11-,13-,14-,15-,16-,19-,20-/m1/s1

描述信息

Nicotinic acid adenine dinucleotide, also known as deamido-NAD or NAAD, belongs to the class of organic compounds known as (5->5)-dinucleotides. These are dinucleotides where the two bases are connected via a (5->5)-phosphodiester linkage. NAAD is possibly soluble (in water) and a strong basic compound (based on its pKa). NAAD exists in all living species, ranging from bacteria to humans. L-Glutamine and NAAD can be converted into L-glutamic acid and NAD; which is catalyzed by the enzyme glutamine-dependent nad(+) synthetase. In humans, NAAD is involved in the nicotinate and nicotinamide metabolism pathway. NAAD is also involved in the metabolic disorder called succinic semialdehyde dehydrogenase deficiency. Outside of the human body, NAAD has been detected, but not quantified in, several different foods, such as japanese walnuts, cauliflowers, sparkleberries, komatsuna, and macadamia nut (m. tetraphylla). This could make NAAD a potential biomarker for the consumption of these foods. NAAD is the product of the degradation of Nicotinic acid adenine dinucleotide phosphate (NAADP) by a Ca2+-sensitive phosphatase. NAADP is a Ca2+-mobilizing second messenger which is synthesized, in response to extracellular stimuli, via the base-exchange reaction by an ADP-ribosyl cyclase (ARC) family members (such as CD38). NAADP binds to and opens Ca2+ channels on intracellular organelles, thereby increasing the intracellular Ca2+ concentration which, in turn, modulates a variety of cellular processes. Structurally, NAADP it is a dinucleotide that only differs from the house-keeping enzyme cofactor, NADP, by a hydroxyl group (replacing the nicotinamide amino group) and yet this minor modification converts it into the most potent Ca2+-mobilizing second messenger yet described. NAADP may also be broken down to 2-phosphoadenosine diphosphoribose (ADPRP) by CD38 or reduced to NAADPH.
Deamido-nad(+), also known as deamidonicotinamide adenine dinucleoetide, is a member of the class of compounds known as (5->5)-dinucleotides (5->5)-dinucleotides are dinucleotides where the two bases are connected via a (5->5)-phosphodiester linkage. Deamido-nad(+) is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Deamido-nad(+) can be found in a number of food items such as garden tomato, sea-buckthornberry, pitanga, and japanese walnut, which makes deamido-nad(+) a potential biomarker for the consumption of these food products. Deamido-nad(+) exists in all living species, ranging from bacteria to humans. In humans, deamido-nad(+) is involved in few metabolic pathways, which include glutamate metabolism, homocarnosinosis, and nicotinate and nicotinamide metabolism. Deamido-nad(+) is also involved in few metabolic disorders, which include 2-hydroxyglutric aciduria (D and L form), 4-hydroxybutyric aciduria/succinic semialdehyde dehydrogenase deficiency, hyperinsulinism-hyperammonemia syndrome, and succinic semialdehyde dehydrogenase deficiency.

同义名列表

15 个代谢物同义名

1-[(2R,3R,4S,5R)-5-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1lambda5-pyridin-1-ylium; 1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carboxy-1lambda5-pyridin-1-ylium; Nicotinamide hypoxanthine dinucleotide sodium salt; Deamidonicotinamide adenine dinucleoetide; Nicotinic acid adenine dinucleotide; Nicotinic acid-adenine dinucleotide; Adenine-nicotinic acid dinucleotide; Deamidodiphosphopyridine nucleotide; Nicotinate adenine dinucleotide; Deamino-nad+; Deamido-nad+; Desamido NAD; Deamido-NAD; NaADN; NAAD



数据库引用编号

24 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(4)

BioCyc(3)

PlantCyc(0)

代谢反应

355 个相关的代谢反应过程信息。

Reactome(68)

BioCyc(10)

WikiPathways(3)

Plant Reactome(240)

INOH(2)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(32)

  • Nicotinate and Nicotinamide Metabolism: NAD + Water ⟶ Adenosine monophosphate + Nicotinamide ribotide
  • Glutamate Metabolism: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • Homocarnosinosis: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • Hyperinsulinism-Hyperammonemia Syndrome: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • 2-Hydroxyglutric Aciduria (D and L Form): Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • Succinic Semialdehyde Dehydrogenase Deficiency: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • NAD Biosynthesis: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + Hydrogen Ion + L-Glutamic acid + NAD + Pyrophosphate
  • NAD Salvage: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + Hydrogen Ion + L-Glutamic acid + NAD + Pyrophosphate
  • NAD Metabolism: N'-Formylkynurenine + Water ⟶ Formic acid + Hydrogen Ion + L-Kynurenine
  • Glutamate Metabolism: Adenosine triphosphate + L-Glutamine ⟶ Adenosine monophosphate + Pyrophosphate
  • Nicotinate and Nicotinamide Metabolism: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • 2-Hydroxyglutric Aciduria (D and L Form): Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid ⟶ Adenosine monophosphate + Guanosine monophosphate + L-Glutamic acid + Pyrophosphate
  • 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency: Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid ⟶ Adenosine monophosphate + Guanosine monophosphate + L-Glutamic acid + Pyrophosphate
  • Homocarnosinosis: Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid ⟶ Adenosine monophosphate + Guanosine monophosphate + L-Glutamic acid + Pyrophosphate
  • Hyperinsulinism-Hyperammonemia Syndrome: Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid ⟶ Adenosine monophosphate + Guanosine monophosphate + L-Glutamic acid + Pyrophosphate
  • Succinic Semialdehyde Dehydrogenase Deficiency: Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid ⟶ Adenosine monophosphate + Guanosine monophosphate + L-Glutamic acid + Pyrophosphate
  • Glutamate Metabolism: Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid ⟶ Adenosine monophosphate + Guanosine monophosphate + L-Glutamic acid + Pyrophosphate
  • Nicotinate and Nicotinamide Metabolism: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • Glutamate Metabolism: Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid ⟶ Adenosine monophosphate + Guanosine monophosphate + L-Glutamic acid + Pyrophosphate
  • Nicotinate and Nicotinamide Metabolism: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • Glutamate Metabolism: Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid ⟶ Adenosine monophosphate + Guanosine monophosphate + L-Glutamic acid + Pyrophosphate
  • Glutamate Metabolism: Adenosine triphosphate + L-Glutamine + Water + Xanthylic acid ⟶ Adenosine monophosphate + Guanosine monophosphate + L-Glutamic acid + Pyrophosphate
  • Nicotinate and Nicotinamide Metabolism: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • 2-Hydroxyglutric Aciduria (D and L Form): Adenosine triphosphate + L-Glutamine ⟶ Adenosine monophosphate + Pyrophosphate
  • 4-Hydroxybutyric Aciduria/Succinic Semialdehyde Dehydrogenase Deficiency: Adenosine triphosphate + L-Glutamine ⟶ Adenosine monophosphate + Pyrophosphate
  • Homocarnosinosis: Adenosine triphosphate + L-Glutamine ⟶ Adenosine monophosphate + Pyrophosphate
  • Hyperinsulinism-Hyperammonemia Syndrome: Adenosine triphosphate + L-Glutamine ⟶ Adenosine monophosphate + Pyrophosphate
  • Succinic Semialdehyde Dehydrogenase Deficiency: Adenosine triphosphate + L-Glutamine ⟶ Adenosine monophosphate + Pyrophosphate
  • Nicotinate and Nicotinamide Metabolism: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + L-Glutamic acid + NAD + Pyrophosphate
  • NAD Biosynthesis: Adenosine triphosphate + Ammonium + Nicotinic acid adenine dinucleotide ⟶ Adenosine monophosphate + Hydrogen Ion + NAD + Pyrophosphate
  • NAD Salvage: Adenosine triphosphate + L-Glutamine + Nicotinic acid adenine dinucleotide + Water ⟶ Adenosine monophosphate + Hydrogen Ion + L-Glutamic acid + NAD + Pyrophosphate

PharmGKB(0)

3 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 7 CA1, CA2, CD36, GJA1, ITPR3, NAAA, SND1
Peripheral membrane protein 2 COX5B, NAAA
Endosome membrane 1 CD14
Endoplasmic reticulum membrane 2 GJA1, ITPR3
Nucleus 4 GJA1, NMNAT1, PARP1, SND1
cytosol 8 CA1, CA2, GJA1, GLS, NADK, PARP1, SND1, TCHH
mitochondrial membrane 1 COX5B
nuclear body 2 NMNAT1, PARP1
phagocytic vesicle 1 CD36
nucleoplasm 4 GJA1, ITPR3, NMNAT1, PARP1
Cell membrane 6 CA2, CD14, CD36, GJA1, TRPM2, TRPM3
Multi-pass membrane protein 6 CATSPER3, CD36, GJA1, ITPR3, TRPM2, TRPM3
Synapse 1 GLS
cell junction 1 GJA1
cell surface 2 CD36, CD38
Golgi apparatus 3 CD14, CD36, GJA1
Golgi membrane 2 GJA1, INS
lysosomal membrane 1 TRPM2
mitochondrial inner membrane 1 COX5B
neuronal cell body 1 ITPR3
Cytoplasm, cytosol 2 GLS, PARP1
Lysosome 2 NAAA, TRPM2
acrosomal vesicle 1 CATSPER3
plasma membrane 9 CA2, CATSPER3, CD14, CD36, CD38, GJA1, ITPR3, TRPM2, TRPM3
Membrane 8 CD36, CD38, ITPR3, NAAA, PARP1, SND1, TRPM2, TRPM3
apical plasma membrane 2 CD36, GJA1
basolateral plasma membrane 1 CD38
brush border 1 ITPR3
caveola 1 CD36
extracellular exosome 6 CA1, CA2, CD14, CD38, NAAA, SND1
endoplasmic reticulum 3 CATSPER3, GJA1, ITPR3
extracellular space 4 CD14, CD36, CXCL8, INS
lysosomal lumen 1 NAAA
gap junction 1 GJA1
intercalated disc 1 GJA1
mitochondrion 4 COX5B, GJA1, GLS, PARP1
protein-containing complex 1 PARP1
intracellular membrane-bounded organelle 1 GJA1
Secreted 3 CD14, CXCL8, INS
extracellular region 3 CD14, CXCL8, INS
mitochondrial matrix 1 GLS
transcription regulator complex 1 PARP1
motile cilium 1 CATSPER3
nuclear membrane 1 CD38
external side of plasma membrane 2 CD14, CD36
perikaryon 1 TRPM2
cytoplasmic vesicle 1 TRPM2
nucleolus 2 ITPR3, PARP1
apical part of cell 2 CA2, ITPR3
Single-pass type II membrane protein 1 CD38
Apical cell membrane 1 CD36
Mitochondrion inner membrane 1 COX5B
Matrix side 1 COX5B
Membrane raft 3 CD14, CD36, GJA1
focal adhesion 1 GJA1
collagen trimer 1 CD36
sarcoplasmic reticulum 1 ITPR3
Cell junction, gap junction 1 GJA1
connexin complex 1 GJA1
contractile muscle fiber 1 GJA1
fascia adherens 1 GJA1
intermediate filament 1 GJA1
lateral plasma membrane 1 GJA1
nuclear outer membrane 1 ITPR3
receptor complex 2 CD36, ITPR3
chromatin 2 NMNAT1, PARP1
cell projection 1 TRPM2
cell periphery 1 CD36
Chromosome 1 PARP1
cytoskeleton 1 TCHH
[Isoform 1]: Mitochondrion 1 GLS
brush border membrane 1 CD36
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
Lipid-anchor, GPI-anchor 1 CD14
[Isoform 2]: Cell membrane 1 TRPM2
site of double-strand break 1 PARP1
nuclear envelope 1 PARP1
endosome lumen 1 INS
Cornified envelope 1 TCHH
Cell projection, cilium, flagellum membrane 1 CATSPER3
Cytoplasmic vesicle membrane 1 TRPM2
specific granule membrane 2 CD36, TRPM2
tertiary granule membrane 1 TRPM2
Melanosome 1 SND1
Golgi-associated vesicle membrane 1 GJA1
side of membrane 1 CD14
myelin sheath 1 CA2
lipopolysaccharide receptor complex 1 CD14
secretory granule lumen 1 INS
secretory granule membrane 2 CD14, ITPR3
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
endocytic vesicle membrane 1 CD36
transport vesicle 1 INS
respiratory chain complex IV 1 COX5B
tight junction 1 GJA1
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
mitochondrial envelope 1 COX5B
platelet dense tubular network membrane 1 ITPR3
protein-DNA complex 1 PARP1
ficolin-1-rich granule membrane 1 TRPM2
[Isoform 1]: Cell membrane 1 TRPM2
Cytoplasmic vesicle, secretory vesicle membrane 1 ITPR3
[Isoform 3]: Mitochondrion 1 GLS
platelet alpha granule membrane 1 CD36
site of DNA damage 1 PARP1
cell-cell contact zone 1 GJA1
[Isoform 3]: Cell membrane 1 TRPM2
[Glutaminase kidney isoform, mitochondrial 68 kDa chain]: Mitochondrion matrix 1 GLS
[Glutaminase kidney isoform, mitochondrial 65 kDa chain]: Mitochondrion matrix 1 GLS
transport vesicle membrane 1 ITPR3
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
cytoplasmic side of endoplasmic reticulum membrane 1 ITPR3
CatSper complex 1 CATSPER3
dense body 1 SND1
RNAi effector complex 1 SND1


文献列表

  • Dahyun Hwang, HyunA Jo, Seong-Ho Ma, Young-Hee Lim. Oxyresveratrol stimulates mucin production in an NAD+-dependent manner in human intestinal goblet cells. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2018 Aug; 118(?):880-888. doi: 10.1016/j.fct.2018.06.039. [PMID: 29935245]
  • Samuel A J Trammell, Mark S Schmidt, Benjamin J Weidemann, Philip Redpath, Frank Jaksch, Ryan W Dellinger, Zhonggang Li, E Dale Abel, Marie E Migaud, Charles Brenner. Nicotinamide riboside is uniquely and orally bioavailable in mice and humans. Nature communications. 2016 10; 7(?):12948. doi: 10.1038/ncomms12948. [PMID: 27721479]
  • Kerly Laskoski, Adrian R S Santos, Ana C Bonatto, Fábio O Pedrosa, Emanuel M Souza, Luciano F Huergo. In vitro characterization of the NAD+ synthetase NadE1 from Herbaspirillum seropedicae. Archives of microbiology. 2016 May; 198(4):307-13. doi: 10.1007/s00203-016-1190-z. [PMID: 26802007]
  • Valerio Mori, Adolfo Amici, Francesca Mazzola, Michele Di Stefano, Laura Conforti, Giulio Magni, Silverio Ruggieri, Nadia Raffaelli, Giuseppe Orsomando. Metabolic profiling of alternative NAD biosynthetic routes in mouse tissues. PloS one. 2014; 9(11):e113939. doi: 10.1371/journal.pone.0113939. [PMID: 25423279]
  • Riko Katahira, Hiroshi Ashihara. Profiles of the biosynthesis and metabolism of pyridine nucleotides in potatoes (Solanum tuberosum L.). Planta. 2009 Dec; 231(1):35-45. doi: 10.1007/s00425-009-1023-2. [PMID: 19820966]
  • Nobumasa Hara, Kazuo Yamada, Masaharu Terashima, Harumi Osago, Makoto Shimoyama, Mikako Tsuchiya. Molecular identification of human glutamine- and ammonia-dependent NAD synthetases. Carbon-nitrogen hydrolase domain confers glutamine dependency. The Journal of biological chemistry. 2003 Mar; 278(13):10914-21. doi: 10.1074/jbc.m209203200. [PMID: 12547821]
  • Kinji Ohno, Masashi Tanaka, Ko Sahashi. [Electron transfer flavoprotein in mitochondria]. Nihon rinsho. Japanese journal of clinical medicine. 2002 Apr; 60 Suppl 4(?):113-7. doi: NULL. [PMID: 12013830]
  • A C Foster, E Okuno, D S Brougher, R Schwarcz. A radioenzymatic assay for quinolinic acid. Analytical biochemistry. 1986 Oct; 158(1):98-103. doi: 10.1016/0003-2697(86)90595-6. [PMID: 2948416]