Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-04-27 16:14:44 UTC |
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HMDB ID | HMDB0001487 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | NADH |
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Description | NADH is the reduced form of NAD+, and NAD+ is the oxidized form of NADH. NAD (or nicotinamide adenine dinucleotide) is used extensively in glycolysis and the citric acid cycle of cellular respiration. The reducing potential stored in NADH can be either converted into ATP through the electron transport chain or used for anabolic metabolism. ATP "energy" is necessary for an organism to live. Green plants obtain ATP through photosynthesis, while other organisms obtain it via cellular respiration (Wikipedia ). NAD is a coenzyme composed of ribosylnicotinamide 5'-diphosphate coupled to adenosine 5'-phosphate by a 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). NADP is formed through the addition of a phosphate group to the 2' position of the adenosyl nucleotide through an ester linkage (Dorland, 27th ed). |
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Structure | |
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Synonyms | Value | Source |
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1,4-DIHYDRONICOTINAMIDE adenine dinucleotide | ChEBI | DPNH | ChEBI | Nicotinamide adenine dinucleotide (reduced) | ChEBI | Reduced nicotinamide adenine dinucleotide | ChEBI | b-DPNH | HMDB | b-NADH | HMDB | beta-DPNH | HMDB | beta-NADH | HMDB | Dihydrocodehydrogenase I | HMDB | Dihydrocozymase | HMDB | Dihydronicotinamide adenine dinucleotide | HMDB | Dihydronicotinamide mononucleotide | HMDB | ENADA | HMDB | NADH2 | HMDB | Reduced codehydrogenase I | HMDB | Reduced diphosphopyridine nucleotide | HMDB | Reduced nicotinamide adenine diphosphate | HMDB | Reduced nicotinamide-adenine dinucleotide | HMDB | Nadide | HMDB | Coenzyme I | HMDB | DPN | HMDB | Diphosphopyridine nucleotide | HMDB | Nicotinamide adenine dinucleotide | HMDB | Nicotinamide-adenine dinucleotide | HMDB | NAD | HMDB | Nucleotide, diphosphopyridine | HMDB | Adenine dinucleotide, dihydronicotinamide | HMDB | Dinucleotide, dihydronicotinamide adenine | HMDB | Dinucleotide, nicotinamide-adenine | HMDB |
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Chemical Formula | C21H29N7O14P2 |
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Average Molecular Weight | 665.441 |
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Monoisotopic Molecular Weight | 665.124771695 |
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IUPAC Name | [({[(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 |
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Traditional Name | NADH |
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CAS Registry Number | 58-68-4 |
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SMILES | NC(=O)C1=CN(C=CC1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2N=CN=C3N)[C@@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1 |
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InChI Key | BOPGDPNILDQYTO-NNYOXOHSSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | (5'->5')-dinucleotides |
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Sub Class | Not Available |
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Direct Parent | (5'->5')-dinucleotides |
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Alternative Parents | |
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Substituents | - (5'->5')-dinucleotide
- Purine nucleotide sugar
- Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Nicotinamide-nucleotide
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- 6-aminopurine
- Monosaccharide phosphate
- N-substituted nicotinamide
- Organic pyrophosphate
- Imidazopyrimidine
- Purine
- Monoalkyl phosphate
- Dihydropyridine
- Aminopyrimidine
- Pyrimidine
- Imidolactam
- Monosaccharide
- N-substituted imidazole
- Alkyl phosphate
- Phosphoric acid ester
- Hydropyridine
- Organic phosphoric acid derivative
- Heteroaromatic compound
- Tetrahydrofuran
- Imidazole
- Vinylogous amide
- Azole
- Amino acid or derivatives
- Primary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Organoheterocyclic compound
- Enamine
- Azacycle
- Oxacycle
- Carboxylic acid derivative
- Hydrocarbon derivative
- Alcohol
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Organopnictogen compound
- Primary amine
- Amine
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 140.0 - 142.0 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Disease References | Nicotinamide Adenine Dinucleotide Deficiency |
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- WholeHealthMD [Link]
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