NADPH

NADPH




Description


NADPH (Nicotinamide adenine dinucleotide phosphate) is a coenzyme that plays an important role in many biochemical reactions in cells. It is a reduced form of NADP+, which stands for nicotinamide adenine dinucleotide phosphate. NADPH is primarily involved in anabolic reactions, such as the biosynthesis of fatty acids, cholesterol, and nucleotides. It provides reducing power, in the form of electrons and hydrogen ions, for these reactions, which allows them to proceed. NADPH is also involved in a number of other cellular processes, including antioxidant defense, detoxification reactions, and the regeneration of glutathione, which is an important antioxidant molecule in cells. In addition, NADPH is required for the activity of various enzymes, such as cytochrome P450 monooxygenases and nitric oxide synthases, which are involved in the metabolism of drugs and other xenobiotics. NADPH is synthesized in cells by a number of enzymes, including glucose-6-phosphate dehydrogenase and malic enzyme. It is important to note that the ratio of NADPH to its oxidized form, NADP+, is tightly regulated in cells, as imbalances can lead to oxidative stress and cellular damage.


Chemical Formula:
C21H26N7O17P3
Molecular Weight:
741.394 Daltons
Monoisotopic Mass:
745.0911021051 Daltons
SMILES:
C5(N(C1(OC(C(C1O)O)COP(OP(OCC4(C(C(C(N3(C2(=C(C(=NC=N2)N)N=C3)))O4)OP([O-])([O-])=O)O))([O-])=O)(=O)[O-]))C=C(CC=5)C(=O)N)
InChI:
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)/p-4/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChIKey:
ACFIXJIJDZMPPO-NNYOXOHSSA-J

Synonyms
  • reduced nicotinamide adenine dinucleotide phosphate
  • NADPH2
  • NADPH2
  • dihydrotriphosphopyridine nucleotide
  • reduced dihydrotriphosphopyridine nucleotide
  • dihydronicotinamide adenine dinucleotide phosphate
  • dihydronicotinamide adenine dinucleotide phosphate reduced
  • reduced NADP
  • NADP-red
  • TPNH
  • dihydronicotinamide adenine dinucleotide-P
  • β-NADPH

Databases
MetaCyc:  NADPH
BiGG:  nadph
RefMet:  NADPH
MetaboLights:  MTBLC57783
HMDB:  HMDB00221
ChemSpider:  10239199
ChEBI:  57783 16474
PubChem (CID):  15983949 5884
CAS:  2646-71-1
KEGG:  C00005
PDB-CCD:  NDP
3DMET:  B01128
NIKKAJI:  J208.978E
Seed:  cpd00005
MetaNetX:  MNXM6
PupChem (SID):  3307
CHEMBL:  CHEMBL1594246 CHEMBL407009