Record Information |
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Version | 1.0 |
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Creation Date | 2016-09-30 22:46:37 UTC |
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Update Date | 2020-06-04 20:14:25 UTC |
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BMDB ID | BMDB0001487 |
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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 | Nadhh, also known as NAD or DPNH, 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. Nadhh exists as a solid, possibly soluble (in water), and a strong basic compound (based on its pKa) molecule. Nadhh exists in all living species, ranging from bacteria to humans. In cattle, nadhh is involved in the metabolic pathway called cancer (via the Warburg effect). |
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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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Status | Detected and Quantified |
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Origin | |
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Biofunction | Not Available |
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Application | Not Available |
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Cellular locations | - Cytoplasm
- Endoplasmic reticulum
- Mitochondria
- Peroxisome
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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 | Not Available | 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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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-002b-1301902000-1a1639ad87019605438c | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive | Not Available | View in JSpectraViewer |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-00n0-0210192000-bf07b6b154c5778067ce | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0udi-0150291000-84ef746651797f0679a5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-0970000000-0688003193d7fc461235 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT 35V, negative | splash10-00di-0190000000-775fe0fdd09a45ed6a96 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT 35V, negative | splash10-052b-0019600000-3247f3ea96ec22c0e190 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT 35V, negative | splash10-052b-0019600000-c62f2c56a1ce8a2874fb | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative | splash10-03di-3212549000-5bb7a136d3e7ca7d8edd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 30V, negative | splash10-00ea-1219600000-1e722b38e19c9839c336 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-00ea-1219600000-25943c109cf639eb967c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-05dj-5449401000-5b1b9b660a66672f95af | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-03di-0000009000-c3a8f40f5761a0b33639 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-054k-6339301000-c1dfbc12dc893f53f0a4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0000009000-ced4da70fe9076bb4c29 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-05dj-5449401000-1c9466169a2e22067bd9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-00kb-0000009000-f46730c3cbc0e239c819 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-1329230000-4e5a5ac7f7ccdfcf5798 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 30V, Negative | splash10-00ea-1219600000-1e722b38e19c9839c336 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0002-0002049000-452a7a02c7cdd0a7db02 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0931104000-bf6579d19ee9bc297e13 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0901000000-92672b1d4b96838f8652 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-1900000000-ef56d203da65089e145f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03e9-1900207000-f248eb28a7283de7118b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-1900100000-efadf1d6c54e9e86671d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a7i-3900000000-f258fc2bf1d8e54ac6da | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-0000009000-7483a50cefc91ed6c523 | View in MoNA |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental) | Not Available | View in JSpectraViewer |
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2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | Not Available | View in JSpectraViewer |
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Biological Properties |
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Cellular Locations | - Cytoplasm
- Endoplasmic reticulum
- Mitochondria
- Peroxisome
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Biospecimen Locations | - Bladder
- Brain
- Fibroblasts
- Liver
- Longissimus Thoracis Muscle
- Platelet
- Semimembranosus Muscle
- Testis
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Pathways | |
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Normal Concentrations |
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Bladder | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Brain | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Liver | Detected and Quantified | 48 +/- 26 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Liver | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Longissimus Thoracis Muscle | Detected and Quantified | 94 +/- 75 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Platelet | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | Semimembranosus Muscle | Detected and Quantified | 101 +/- 45 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | Testis | Detected and Quantified | 21 +/- 8 nmol/g of tissue | Not Specified | Not Specified | Normal | | details |
| Show more...
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Abnormal Concentrations |
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| Not Available |
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External Links |
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HMDB ID | HMDB0001487 |
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DrugBank ID | DB00157 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022649 |
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KNApSAcK ID | C00019343 |
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Chemspider ID | 903 |
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KEGG Compound ID | C00004 |
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BioCyc ID | NADH |
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BiGG ID | 33484 |
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Wikipedia Link | Nicotinamide_adenine_dinucleotide |
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METLIN ID | 3687 |
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PubChem Compound | 439153 |
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PDB ID | Not Available |
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ChEBI ID | 16908 |
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References |
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Synthesis Reference | Marek, Miroslav; Vrbova, Eva; Horakova, Irena; Musil, Petr; Kefurt, Karel. NADH manufacture with immobilized Candida formate dehydrogenase. Czech. (1992), 4 pp. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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