Dihydronicotinamid-adenin-dinucleotid-phosphat

NADPH

HCID 5884CAS 53-57-6

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Grundinformationen

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
Summenformel: C21H30N7O17P3
Durchschnittliche Molmasse: 745,4 g/mol

Überblick

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-).

Namen und Bezeichner

Bevorzugter 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
Lokaler Name: Dihydronicotinamid-adenin-dinucleotid-phosphat
Englischer Name: NADPH
Summenformel: C21H30N7O17P3
Molmasse: 745.42

Namen und Synonyme

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

Weitere Namen anzeigen

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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -6,8
Polarare Oberfläche (TPSA): 364 Å²
H-Brücken-Donoren: 9
H-Brücken-Akzeptoren: 22
Frei drehbare Bindungen: 13
Schwere Atome: 48
Formalladung: 0
Komplexität: 1.410

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Other Biomolecules

DrugsPharmaceuticals -> Listed in ZINC15

Physical DescriptionSolid

Collision Cross Section · 2 Einträge

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]-

Physikochemische Eigenschaften

Siedepunkt: 1175.1 · 1175.1±75.0 °C(Predicted)
Dichte: 2.28 · 2.28±0.1 g/cm3(Predicted)
pka: 1.13 · 1.13±0.50(Predicted)
Aggregatzustand: Solid
Farbe: White to light yellow
EPA chemische Informationen: Nicotinamide adenine dinucleotide phosphate (53-57-6)

Sicherheit und Regulatorisches

Gefahrenhinweise

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.

Sicherheitsdaten

tsca: TSCA listed

Chemie und Industrie

Pharmakologische Informationen

Tissue LocationsAll Tissues

Cellular LocationsCytoplasm

Metabolite Pathways11-beta-hydroxylase deficiency (CYP11B1)

Verwendung und Herstellung

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

Anwendungen · 1 Eintrag

VerwendenOne 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

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Nachgelagerte Produkte

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

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Ergänzende Hinweise · 1 Eintrag

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.