NADPH

HCID 5884CAS 53-57-6

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Basic information

Standard SMILES: NC(=O)C1=CN([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1
InChIKey: ACFIXJIJDZMPPO-NNYOXOHSSA-N
Molecular formula: C21H30N7O17P3
Average molar mass: 745.4 g/mol

Overview

NADPH is the reduced form of NADP+; used in anabolic reactions, such as lipid and nucleic acid synthesis, which require NADPH as a reducing agent. It has a role as a cofactor and a fundamental metabolite. It is a NAD(P)H and a NADP. It is a conjugate acid of a NADPH(4-).

Names & identifiers

Preferred name: NADPH
IUPAC: [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
English name: NADPH
Molecular formula: C21H30N7O17P3
Molecular weight: 745.42

Names & synonyms

NADPH53-57-6TPNHDihydronicotinamide-adenine dinucleotide phosphatebeta-NADPHDihydrocodehydrogenase II2646-71-1Reduced triphosphopyridine nucleotideReduced Nicotinamide Adenine Dinucleotide PhosphateNADPH2MFCD00674870381Q4X082D

Show more names

reducedNADPNNa4 saltent-NADPHβ-NADPH-d4NADPH ≥98%Reduced Co IITriphosphopyridine Nu

dihydronicotinamide adenine dinucleotide phosphatereduced nicotinamide-adenine dinucleotide phosphate[[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphateNicotinamide-adenine dinucleotide phosphate, reducedAdenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamidereduced Coenzyme IIMFCD00036263dihydronicotinamide adenine dinucleotide-P

Database identifiers

CAS: 53-57-6
PubChem CID: 5884
DTXSID: DTXSID001018921
ChEMBL: CHEMBL407009
ChEBI: CHEBI:16474
UNII: 381Q4X082D
EC Number: 200-177-6
Nikkaji: J213.537J

Properties

Computed structural properties

XLogP: -6.8
Topological polar surface area: 364 Å²
Hydrogen bond donors: 9
Hydrogen bond acceptors: 22
Rotatable bonds: 13
Heavy atoms: 48
Formal charge: 0
Complexity: 1,410

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Other Biomolecules

DrugsPharmaceuticals -> Listed in ZINC15

Physical DescriptionSolid

Collision Cross Section · 2 items

240.5 Å² [M+Na-H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

246.7 Å² [M-H]-

Physicochemical properties

Boiling point: 1175.1 · 1175.1±75.0 °C(Predicted)
Density: 2.28 · 2.28±0.1 g/cm3(Predicted)
pka: 1.13 · 1.13±0.50(Predicted)
form: Solid
color: White to light yellow
FDA UNII: 381 Q4X082D · 381Q4X082D
EPA Substance Registry System: Nicotinamide adenine dinucleotide phosphate (53-57-6)
TSCA: TSCA listed

Safety & regulation

Hazard information

Regulatory InformationAdenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'â5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySee NADP.

Safety data

tsca: TSCA listed

Chemistry & industry

Pharmacology

Tissue LocationsAll Tissues

Cellular LocationsCytoplasm

Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)

Uses & manufacturing

UsesThe reduced form of NADP found in living cells; [Merck Index]

General Manufacturing InformationAdenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'.fwdarw.5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide: INACTIVE

Applications · 2 items

Usesβ-NADPH-d4 is the isotope labelled analog of β-NADPH. One of the biologically active forms of nicotinic acid. Differs from NAD by an additional phosphate group at the 2’-position of the adenosine moiety. Serves as a coenzyme of hydrogenases and dehydrogenases. Present in living cells primarily in the reduced form (NADPH) and is involved in synthetic reactions.

UsesOne of the biologically active forms of nicotinic acid. Differs from NAD by an additional phosphate group at the 2position of the adenosine moiety. Serves as a coenzyme of hydrogenases and dehydrogenases. Present in living cells primarily in the r

Upstream & downstream products

Upstream raw materials

Downstream products

5-amino-2,5-dioxo-pentanoic acid

Suppliers40 total

上海摩睿化学科技有限公司13382110328 15255501563 · [email protected]

Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

曼顿生物科技（深圳）有限公司+86-75589664337 +86-15112661142 · [email protected]

Hong Kong Tiansheng New Material Trading Co., Ltd+8617320695765 · [email protected]

Additional notes · 1 item

DefinitionA coenzyme composed of ribosylnicotinamide 5′- phosphate coupled by pyrophosphate linkage to the 5′-phosphate adenosine 2′,5′-bisphosphate. The reduced from of NADP. It is an energy-storage form that can be transferred to the Calvin cycle where it participates in the production of carbohydrate.