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NADPH (PC000430)

Record Information
Version1.0
Creation date2015-10-09 22:30:39 UTC
Update date2017-01-19 02:36:23 UTC
FoodComEx IDPC000430
FoodDB RecordFDB021909
Chemical Information
NameNADPH
DescriptionNicotinamide 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.) [HMDB]. NADPH is found in many foods, some of which are american pokeweed, rice, ginseng, and ostrich fern.
CAS Number53-57-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2'-(Dihydrogen ate) 5'-(trihydrogen pyroate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamideHMDB
2'-(Dihydrogen ate) 5'-(trihydrogen pyroate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamideHMDB
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 diate) 2'-(dihydrogen ate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamideHMDB
Adenosine 5'-(trihydrogen diate) 2'-(dihydrogen ate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamideHMDB
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-orateHMDB
b-Nicotinamide-adenine-dinucleotide-oric acidHMDB
b-Nicotinamide-adenine-dinucleotide-phosphoratehmdb
b-Nicotinamide-adenine-dinucleotide-phosphoric acidhmdb
beta-NADPHhmdb
beta-Nicotinamide-adenine-dinucleotide-orateHMDB
beta-Nicotinamide-adenine-dinucleotide-oric acidHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphoratehmdb
beta-Nicotinamide-adenine-dinucleotide-phosphoric acidhmdb
Dihydrocodehydrogenase IIhmdb
Dihydronicotinamide adenine dinucleotide ateHMDB
dihydronicotinamide adenine dinucleotide phosphatehmdb
dihydronicotinamide adenine dinucleotide-Phmdb
Dihydrotriopyridine nucleotide reducedHMDB
dihydrotriphosphopyridine nucleotide reducedhmdb
NADP-reducedhmdb
NADPHhmdb
Nicotinamide adenine dinucleotide ate - reducedHMDB
Nicotinamide-adenine-dinucleotide-orateHMDB
Nicotinamide-adenine-dinucleotide-oric acidHMDB
Nicotinamide-adenine-dinucleotide-phosphoratehmdb
Nicotinamide-adenine-dinucleotide-phosphoric acidhmdb
reduced Codehydrase IIhmdb
reduced Coenzyme IIhmdb
reduced Cozymase IIhmdb
Reduced triopyridine nucleotideHMDB
Reduced triphosphopyridine nucleotidehmdb
Triopyridine nucleotide reducedHMDB
Triphosphopyridine nucleotide reducedhmdb
Chemical FormulaC21H30N7O17P3
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
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
Isomeric 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
Average Molecular Weight745.4209
Monoisotopic Molecular Weight745.091102105
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
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 20 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Toronto Research Chemicals N201504