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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30N7O17P3
Molecular Weight 745.4209
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICOTINAMIDE-ADENINE DINUCLEOTIDE PHOSPHATE, REDUCED

SMILES

NC(=O)C1=CN(C=CC1)[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](OP(O)(O)=O)[C@@H]3O)N4C=NC5=C4N=CN=C5N)[C@@H](O)[C@H]2O

InChI

InChIKey=ACFIXJIJDZMPPO-NNYOXOHSSA-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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H30N7O17P3
Molecular Weight 745.4209
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Nicotinamide-adenine dinucleotide phosphate, reduced (NADPH) is the reduced form of the electron acceptor NADP+ and acts as an electron donor in various biological reactions. In plants, NADPH is produced by ferredoxin-NADP+ reductase in the last step of the electron chain during photosynthesis. In animals it is predominantly produced by the pentose phosphate pathway, but it is also generated by key mitochondrial enzymes. NADPH provides the reducing equivalents for biosynthetic reactions and the oxidation-reduction involved in protecting against the toxicity of reactive oxygen species. It is also used for the synthesis of lipids and cholesterol and during the process of fatty acid chain elongation. β-Nicotinamide adenine dinucleotide 2′-phosphate (NADP+) and β-Nicotinamide adenine dinucleotide 2′-phosphate, reduced (NADPH) comprise a coenzyme redox pair (NADP+:NADPH) involved in a wide range of enzyme catalyzed oxidation reduction reactions. The NADP+/NADPH redox pair facilitates electron transfer in anabolic reactions such as lipid and cholesterol biosynthesis and fatty acyl chain elongation. The NADP+/NADPH redox pair is used in a variety of antioxidation mechanism where it protects agains reactive oxidation species accumulation. NADPH protects against redox stress by providing reducing equivalents to antioxidants such as glutathione and thioredoxin. NADPH levels decline with aging in several tissues, but whether this is a major driving force for the aging process has not been well established. Both NADPH and NAD+ have been reported to have potent neuroprotective effects against ischemic neuronal injury. The combination of NADPH and NAD+ may provide a novel effective therapy for ischemic stroke.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Production of cytoplasmic NADPH2 other than by the pentose cycle in adipose tissue].
1967
Studies on the mechanism of metabolic stimulation in polymorphonuclear leucocytes during phagocytosis. I. Evidence for superoxide anion involvement in the oxidation of NADPH2.
1975 Apr 7
Memo is a copper-dependent redox protein with an essential role in migration and metastasis.
2014 Jun 10
NADPH metabolism: a survey of its theoretical characteristics and manipulation strategies in amino acid biosynthesis.
2018 Nov

Sample Use Guides

In in vivo studies, NAD+ (12.5–50 mg/kg) or NADPH (2.5 or 7.5 mg/kg), dissolved in 0.9% saline solution, was administered to mice via tail vein at the onset of reperfusion or at the indicated time after reperfusion.
Route of Administration: Intravenous
Insect ganglia were directly incubated in an NADPHd staining solution of 0.2 mM nicotinamide-adenine dinucleotide phosphate, reduced (β-NADPH) and 0.2 mM nitroblue tetrazolium (NBT) in Tris-Tx for 1–3 hr at RT.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:53:01 GMT 2023
Edited
by admin
on Sat Dec 16 09:53:01 GMT 2023
Record UNII
381Q4X082D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NICOTINAMIDE-ADENINE DINUCLEOTIDE PHOSPHATE, REDUCED
Common Name English
.BETA.-NICOTINAMIDE-ADENINE-DINUCLEOTIDE-PHOSPHORIC ACID
Common Name English
NADPH
Common Name English
REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE
Common Name English
ADENOSINE 5'-(TRIHYDROGEN DIPHOSPHATE), 2'-(DIHYDROGEN PHOSPHATE), P'->5'-ESTER WITH 1,4-DIHYDRO-1-.BETA.-D-RIBOFURANOSYL-3-PYRIDINECARBOXAMIDE
Common Name English
COENZYME II, REDUCED
Common Name English
TPNH
Common Name English
NADP REDUCED FOM
Common Name English
NADPH2
Common Name English
NADP REDUCED FORM [MI]
Common Name English
REDUCED CODEHYDROGENASE II
Common Name English
.BETA.-NADPH
Common Name English
REDUCED TRIPHOSPHOPYRIDINE NUCLEOTIDE
Common Name English
DIHYDROCODEHYDROGENASE II
Common Name English
Code System Code Type Description
FDA UNII
381Q4X082D
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY
CHEBI
16474
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-177-6
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY
PUBCHEM
5884
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY
MERCK INDEX
m7702
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
NADPH
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY
CHEBI
57783
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY
CAS
53-57-6
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID001018921
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY
EVMPD
SUB22887
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY
DRUG BANK
DB02338
Created by admin on Sat Dec 16 09:53:01 GMT 2023 , Edited by admin on Sat Dec 16 09:53:01 GMT 2023
PRIMARY