2′-Monophosphoadenosine 5′-Diphosphoribose

Status : experimental

Description

Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed)

Chemical Classification

This compound belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Purine nucleotide sugars

Organic compounds

Nucleosides, nucleotides, and analogues

Purine nucleotides

Purine nucleotide sugars

Calculated Property

kind Value Source
logP -0.81 ALOGPS
logS -2.2 ALOGPS
Water Solubility 4.84e+00 g/l ALOGPS
logP -11 ChemAxon
IUPAC Name 1-[(2R,3R,4R,5S)-5-{[({[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ⁵-pyridin-1-ylium ChemAxon
Traditional IUPAC Name 1-[(2R,3R,4R,5S)-5-[({[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl phosphonato}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1λ⁵-pyridin-1-ylium ChemAxon
Molecular Weight 743.405 ChemAxon
Monoisotopic Weight 743.075452041 ChemAxon
SMILES NC(=O)C1=CC=C[N+](=C1)[C@@H]1O[C@@H](CO[P@]([O-])(=O)O[P@@](O)(=O)OC[C@@H]2O[C@H]([C@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C2N=CN=C3N)[C@H](O)[C@H]1O ChemAxon
Molecular Formula C21H28N7O17P3 ChemAxon
InChI InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15+,16+,20+,21+/m0/s1 ChemAxon
InChIKey InChIKey=XJLXINKUBYWONI-XCSFTKGKSA-N ChemAxon
Polar Surface Area (PSA) 367.62 ChemAxon
Refractivity 151.75 ChemAxon
Polarizability 62.06 ChemAxon
Rotatable Bond Count 13 ChemAxon
H Bond Acceptor Count 17 ChemAxon
H Bond Donor Count 8 ChemAxon
pKa (strongest acidic) 0.66 ChemAxon
pKa (strongest basic) 4.92 ChemAxon
Physiological Charge -3 ChemAxon
Number of Rings 5 ChemAxon
Bioavailability 0 ChemAxon
Rule of Five 0 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 1 ChemAxon

Target within organism

  • Alcohol dehydrogenase 1B : in Human
  • NADPH–cytochrome P450 reductase : in Human
  • Shikimate dehydrogenase : in Escherichia coli (strain K12)
  • NADP-dependent isopropanol dehydrogenase : in Thermoanaerobacter brockii
  • GDP-L-fucose synthase : in Escherichia coli (strain K12)
  • Aspartate-semialdehyde dehydrogenase : in Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
  • 2,4-dienoyl-CoA reductase [NADPH] : in Escherichia coli (strain K12)
  • NADP-dependent malic enzyme : in Human
  • NAD(P) transhydrogenase subunit beta : in Rhodospirillum rubrum
  • 3-oxoacyl-[acyl-carrier-protein] reductase FabG : in Escherichia coli (strain K12)
  • Isocitrate dehydrogenase [NADP] : in Escherichia coli (strain K12)
  • Aldose reductase : in Human
  • Glucose-6-phosphate 1-dehydrogenase : in Leuconostoc mesenteroides
  • Aldo-keto reductase family 1 member C2 : in Human
  • Estradiol 17-beta-dehydrogenase 1 : in Human
  • NAD(P) transhydrogenase, mitochondrial : in Human
  • Corticosteroid 11-beta-dehydrogenase isozyme 1 : in Human
  • Sepiapterin reductase : in Human
  • Pteridine reductase 1 : in Leishmania major
  • L-xylulose reductase : in Human
  • Isocitrate dehydrogenase [NADP] cytoplasmic : in Human
  • Dihydrofolate reductase : in Escherichia coli (strain K12)
  • Aldo-keto reductase family 1 member C1 : in Human
  • Nitric oxide synthase, brain : in Human
  • Glucose-6-phosphate 1-dehydrogenase : in Human
  • Dihydrofolate reductase : in Human
  • ADP-L-glycero-D-manno-heptose-6-epimerase : in Escherichia coli (strain K12)
  • C-1-tetrahydrofolate synthase, cytoplasmic : in Human
  • Aldo-keto reductase family 1 member C3 : in Human
  • Flavin reductase (NADPH) : in Human
  • Isocitrate dehydrogenase [NADP] : in Azotobacter vinelandii
  • Dihydrofolate reductase : in Pneumocystis carinii
  • Quinone oxidoreductase : in Human
  • Dehydrogenase/reductase SDR family member 11 : in Human
  • 3-hydroxy-3-methylglutaryl-coenzyme A reductase : in Human
  • Malate dehydrogenase, cytoplasmic : in Human
  • Oxidoreductase YdhF : in Escherichia coli (strain K12)
  • Putative pteridine reductase 2 : in Trypanosoma cruzi
  • Estradiol 17-beta-dehydrogenase 8 : in Human
  • Alcohol dehydrogenase [NADP(+)] : in Human
  • Putative ketoacyl reductase : in Streptomyces coelicolor (strain ATCC BAA-471 / A3(2) / M145)
  • 2,4-dienoyl-CoA reductase, mitochondrial : in Human
  • Oxidoreductase, short chain dehydrogenase/reductase family : in Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
  • Prostaglandin F synthase : in Trypanosoma brucei brucei
  • General stress protein 69 : in Bacillus subtilis (strain 168)
  • Ferredoxin–NADP reductase : in Anabaena sp. (strain PCC 7119)
  • Bifunctional protein MdtA : in Methylobacterium extorquens (strain ATCC 14718 / DSM 1338 / AM1)
  • Alcohol dehydrogenase : in Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
  • NADPH:adrenodoxin oxidoreductase, mitochondrial : in Human
  • Ferredoxin–NADP reductase : in Nostoc sp. (strain PCC 7120 / UTEX 2576)
  • 2,5-diketo-D-gluconic acid reductase A : in Corynebacterium sp. (strain ATCC 31090)
  • Protein IolS : in Bacillus subtilis (strain 168)
  • NADP-dependent glyceraldehyde-3-phosphate dehydrogenase : in Streptococcus mutans serotype c (strain ATCC 700610 / UA159)
  • Prostaglandin reductase 1 : in Human
  • Sulfite reductase [NADPH] flavoprotein alpha-component : in Escherichia coli (strain K12)
  • Aldo-keto reductase family 1 member B10 : in Human
  • Alcohol dehydrogenase (NADP(+)) : in Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
  • NADP-dependent fatty aldehyde dehydrogenase : in Vibrio harveyi
  • Putative dehydrogenase/reductase SDR family member 4-like 2 : in Human
  • Aldehyde reductase : in Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)