NADPH (CHEM034785)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:13:08 UTC
Update Date2016-11-09 01:21:11 UTC
Accession NumberCHEM034785
Identification
Common NameNADPH
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamideHMDB
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamideHMDB
b-NADPHHMDB
b-Nicotinamide-adenine-dinucleotide-phosphorateHMDB
b-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
beta-NADPHHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphorateHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Dihydrocodehydrogenase IIHMDB
Dihydronicotinamide adenine dinucleotide phosphateHMDB
Dihydronicotinamide adenine dinucleotide-pHMDB
Dihydrotriphosphopyridine nucleotide reducedHMDB
NADP-reducedHMDB
Nicotinamide adenine dinucleotide phosphate - reducedHMDB
Nicotinamide-adenine-dinucleotide-phosphorateHMDB
Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Reduced codehydrase IIHMDB
Reduced coenzyme IIHMDB
Reduced cozymase IIHMDB
Reduced triphosphopyridine nucleotideHMDB
Triphosphopyridine nucleotide reducedHMDB
Chemical FormulaC21H30N7O17P3
Average Molecular Mass745.421 g/mol
Monoisotopic Mass745.091 g/mol
CAS Registry Number53-57-6
IUPAC Name{[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2S,3S,4S,5S)-2-(6-aminopurin-9-yl)-5-{[({[(2S,3R,4S,5S)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
SMILESNC(=O)C1=CN(C=CC1)[C@H]1O[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2O[C@@H]([C@@H](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C21H30N7O17P3/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/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1
InChI KeyACFIXJIJDZMPPO-NCHANQSKSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class(5'->5')-dinucleotides
Sub ClassNot Available
Direct Parent(5'->5')-dinucleotides
Alternative Parents
Substituents
  • (5'->5')-dinucleotide
  • Purine nucleotide sugar
  • Purine ribonucleoside 2',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Nicotinamide-nucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • N-substituted nicotinamide
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Dihydropyridine
  • Aminopyrimidine
  • Organic phosphoric acid derivative
  • Pyrimidine
  • N-substituted imidazole
  • Hydropyridine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Imidolactam
  • Monosaccharide
  • Vinylogous amide
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Enamine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Amine
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxide
  • Primary amine
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.45 g/LALOGPS
logP-1.1ALOGPS
logP-6.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)4ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area364.15 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity153.87 m³·mol⁻¹ChemAxon
Polarizability63.02 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9421780200-89062ec4778392672634Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-02tj-1838493720-b38b37650e8976905bb0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4r-0841393100-6e4cbc8ac576e3e8b195Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0550-2694875730-0dc522520957880672cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0921104300-c1952197674952109d2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-31adeef6c90e9070dfa4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0920000000-e29dcab04f59f9c7189cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0036-6900111800-ab3c73d03c4430e1b644Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4901100000-96b551ade48c419935edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900000000-0898019fd8b891d5245eSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000221
FooDB IDFDB021909
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID33486
BioCyc IDNot Available
METLIN ID3691
PDB IDNot Available
Wikipedia LinkNicotinamide adenine dinucleotide phosphate
Chemspider ID17215925
ChEBI ID16474
PubChem Compound ID22833512
Kegg Compound IDC00005
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Seelbach, Karsten; Riebel, Bettina; Hummel, Werner; Kula, Maria-Regina; Tishkov, Vladimir I.; Egorov, Alexey M.; Wandrey, Christian; Kragl, Udo. A novel, efficient regenerating method of NADPH using a new formate dehydrogenase. Tetrahedron Letters (1996), 37(9), 1377-80.
2. Shindo Y, Witt E, Han D, Epstein W, Packer L: Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin. J Invest Dermatol. 1994 Jan;102(1):122-4.
3. Iwata H, Tezuka Y, Kadota S, Hiratsuka A, Watabe T: Mechanism-based inactivation of human liver microsomal CYP3A4 by rutaecarpine and limonin from Evodia fruit extract. Drug Metab Pharmacokinet. 2005 Feb;20(1):34-45.
4. Birkmayer GJ, Birkmayer W: Stimulation of endogenous L-dopa biosynthesis--a new principle for the therapy of Parkinson's disease. The clinical effect of nicotinamide adenine dinucleotide (NADH) and nicotinamide adenine dinucleotidephosphate (NADPH). Acta Neurol Scand Suppl. 1989;126:183-7.
5. Lee AJ, Zhu BT: NADPH-dependent formation of polar and nonpolar estrogen metabolites following incubations of 17 beta-estradiol with human liver microsomes. Drug Metab Dispos. 2004 Aug;32(8):876-83.
6. Kochansky CJ, Xia YQ, Wang S, Cato B, Creighton M, Vincent SH, Franklin RB, Reed JR: Species differences in the elimination of a peroxisome proliferator-activated receptor agonist highlighted by oxidative metabolism of its acyl glucuronide. Drug Metab Dispos. 2005 Dec;33(12):1894-904. Epub 2005 Sep 23.
7. Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2:18.
8. Karanam BV, Hop CE, Liu DQ, Wallace M, Dean D, Satoh H, Komuro M, Awano K, Vincent SH: In vitro metabolism of MK-0767 [(+/-)-5-[(2,4-dioxothiazolidin-5-yl)methyl]-2-methoxy-N-[[(4-trifluoromethyl) phenyl]methyl]benzamide], a peroxisome proliferator-activated receptor alpha/gamma agonist. I. Role of cytochrome P450, methyltransferases, flavin monooxygenases, and esterases. Drug Metab Dispos. 2004 Sep;32(9):1015-22.
9. Soglia JR, Contillo LG, Kalgutkar AS, Zhao S, Hop CE, Boyd JG, Cole MJ: A semiquantitative method for the determination of reactive metabolite conjugate levels in vitro utilizing liquid chromatography-tandem mass spectrometry and novel quaternary ammonium glutathione analogues. Chem Res Toxicol. 2006 Mar;19(3):480-90.
10. Afanas'ev IB, Suslova TB, Cheremisina ZP, Abramova NE, Korkina LG: Study of antioxidant properties of metal aspartates. Analyst. 1995 Mar;120(3):859-62.
11. Lin CC, Wong BK, Burgey CS, Gibson CR, Singh R: In vitro metabolism of a thrombin inhibitor and quantitation of metabolically generated cyanide. J Pharm Biomed Anal. 2005 Oct 4;39(5):1014-20. Epub 2005 Jul 14.
12. Conley AJ, Pattison JC, Bird IM: Variations in adrenal androgen production among (nonhuman) primates. Semin Reprod Med. 2004 Nov;22(4):311-26.