Dihydronicotinamid-adenin-dinucleotid
Nadh
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Grundinformationen
- CAS
58-68-4- 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](O)[C@@H]3O)[C@@H](O)[C@H]2O)C=CC1- InChIKey
BOPGDPNILDQYTO-NNYOXOHSSA-N- Summenformel
- C21H29N7O14P2
- Durchschnittliche Molmasse
- 665,4 g/mol
- Monoisotopische Masse
- 665,12477262
Namen und Bezeichner
- Bevorzugter Name
- Nadh
- IUPAC
- [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-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
- Englischer Name
- dihydrodiphosphopyridine nucleotide
- Summenformel
- C21H29N7O14P2
- Molmasse
- 665.44
Namen und Synonyme
NADHDPNHbeta-NADH58-68-41,4-Dihydronicotinamide adenine dinucleotideNADH2dihydronicotinamide adenine dinucleotideReduced nicotinamide adenine diphosphateReduced nicotinamide-adenine dinucleotideReduced Nicotinamide Adenine Dinucleotide[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate4J24DQ0916
Weitere Namen anzeigen
NICOTINAMIDE ADENINE DINUCLEOTIDEdihydrocozymaseReduced formβ-NADH, DPNH, NADHReduced codehydrase ITestosterone 17β-dehydrogenase
Nicotinamide-adenine dinucleotide, reducednicotinamide adenine dinucleotide (reduced)CHEBI:16908DTXSID30889320[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acidAdenosine 5'-(trihydrogen diphosphate), P'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamideNAD reduced(((((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(hydroxy)phosphoryl)oxy)((((2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy))phosphinic acid
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- -5,7
- Polarare Oberfläche (TPSA)
- 318 Ų
- H-Brücken-Donoren
- 8
- H-Brücken-Akzeptoren
- 19
- Frei drehbare Bindungen
- 11
- Schwere Atome
- 44
- Formalladung
- 0
- Komplexität
- 1.230
Experimentelle und physikochemische Eigenschaften
LogP-5.1
Melting Point
140.0-142.0 °C
140.0 - 142.0 °C
Physical DescriptionSolid
Physikochemische Eigenschaften
- Siedepunkt
- 1081.8 · 1081.8±75.0 °C(Predicted)
- Dichte
- 2.18 · 2.18±0.1 g/cm3(Predicted)
- Löslichkeit
- Water (Slightly)
- pka
- 1.13 · 1.13±0.50(Predicted)
- Aggregatzustand
- Solid
- Farbe
- White to Off-White
- Stabilität
- Light Sensitive, Temperature Sensitive
- InChIKey
- BOPGDPNILDQYTO-NNYOXOHSSA-N
- EPA chemische Informationen
- 5 · Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide (58-68-4)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Gefahrenhinweise
Regulatory Information
Chemical: Adenosine 5â²-(trihydrogen diphosphate), Pâ².fwdarw.5â²-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate), P'â5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide, disodium salt: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Regulatorische Informationen
Regulatory Information
Chemical: Adenosine 5â²-(trihydrogen diphosphate), Pâ².fwdarw.5â²-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide
Adenosine 5'-(trihydrogen diphosphate), P'â5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide, disodium salt: Does not have an individual approval but may be used under an appropriate group standard
Sicherheitsdaten
- tsca
- TSCA listed
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
A coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by pyrophosphate linkage. It is found widely in nature and is involved in numerous enzymatic reactions in which it serves as an electron carrier by being alternately oxidized (NAD+) and reduced (NADH). The action of supplemental NADH is unclear. Oral NADH supplementation has been used to combat simple fatigue as well as such mysterious and energy-sapping disorders as chronic fatigue syndrome and fibromyalgia. Researchers are also studying the value of NADH supplements for improving mental function in people with Alzheimer's disease, and minimizing physical disability and relieving depression in people with Parkinson's disease. Some healthy individuals also take NADH supplements orally to improve concentration and memory capacity, as well as to increase athletic endurance. However, to date there have been no published studies to indicate that using NADH is in any way effective or safe for these purposes.
Mechanism of Action
NADH is synthesized by the body and thus is not an essential nutrient. It does require the essential nutrient nicotinamide for its synthesis, and its role in energy production is certainly an essential one. In addition to its role in the mitochondrial electron transport chain, NADH is produced in the cytosol. The mitochondrial membrane is impermeable to NADH, and this permeability barrier effectively separates the cytoplasmic from the mitochondrial NADH pools. However, cytoplasmic NADH can be used for biologic energy production. This occurs when the malate-aspartate shuttle introduces reducing equivalents from NADH in the cytosol to the electron transport chain of the mitochondria. This shuttle mainly occurs in the liver and heart.
Absorption, Distribution and ExcretionUnclear how much of an administered dose is absorbed.
Tissue LocationsBladder；Brain；Fibroblasts；Platelet；Skeletal Muscle
Cellular LocationsEndoplasmic reticulum；Mitochondria；Peroxisome
Metabolite Pathways
Zugehörige Reaktionen
141
Notizen zur Verbindung
Wird geladen…