Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:04:59 UTC |
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Update date | 2019-11-26 03:21:00 UTC |
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Primary ID | FDB021909 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | NADPH |
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Description | Nicotinamide adenine dinucleotide phosphate. A coenzyme composed of ribosylnicotinamide 5'-phosphate (NMN) coupled by pyrophosphate linkage to the 5'-phosphate adenosine 2',5'-bisphosphate. It serves as an electron carrier in a number of reactions, being alternately oxidized (NADP+) and reduced (NADPH). (Dorland, 27th ed.) [HMDB]. NADPH is found in many foods, some of which are american pokeweed, rice, ginseng, and ostrich fern. |
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CAS Number | 53-57-6 |
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Structure | |
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Synonyms | Synonym | Source |
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2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide | HMDB | 2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide | HMDB | Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide | HMDB | Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide | HMDB | b-NADPH | HMDB | b-Nicotinamide-adenine-dinucleotide-phosphorate | HMDB | b-Nicotinamide-adenine-dinucleotide-phosphoric acid | HMDB | beta-NADPH | HMDB | beta-Nicotinamide-adenine-dinucleotide-phosphorate | HMDB | beta-Nicotinamide-adenine-dinucleotide-phosphoric acid | HMDB | Dihydrocodehydrogenase II | HMDB | Dihydronicotinamide adenine dinucleotide phosphate | HMDB | Dihydronicotinamide adenine dinucleotide-p | HMDB | Dihydrotriphosphopyridine nucleotide reduced | HMDB | NADP-reduced | HMDB | Nicotinamide adenine dinucleotide phosphate - reduced | HMDB | Nicotinamide-adenine-dinucleotide-phosphorate | HMDB | Nicotinamide-adenine-dinucleotide-phosphoric acid | HMDB | Reduced codehydrase II | HMDB | Reduced coenzyme II | HMDB | Reduced cozymase II | HMDB | Reduced triphosphopyridine nucleotide | HMDB | Triphosphopyridine nucleotide reduced | HMDB | 2'-(Dihydrogen ate) 5'-(trihydrogen pyroate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide | HMDB | 2'-(Dihydrogen ate) 5'-(trihydrogen pyroate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide | HMDB | 2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamide | hmdb | 2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamide | hmdb | Adenosine 5'-(trihydrogen diate) 2'-(dihydrogen ate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide | HMDB | Adenosine 5'-(trihydrogen diate) 2'-(dihydrogen ate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide | HMDB | Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide | hmdb | Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamide | hmdb | b-Nicotinamide-adenine-dinucleotide-orate | HMDB | b-Nicotinamide-adenine-dinucleotide-oric acid | HMDB | beta-Nicotinamide-adenine-dinucleotide-orate | HMDB | beta-Nicotinamide-adenine-dinucleotide-oric acid | HMDB | Dihydronicotinamide adenine dinucleotide ate | HMDB | dihydronicotinamide adenine dinucleotide phosphate | hmdb | dihydronicotinamide adenine dinucleotide-P | hmdb | Dihydrotriopyridine nucleotide reduced | HMDB | dihydrotriphosphopyridine nucleotide reduced | hmdb | NADPH | hmdb | Nicotinamide adenine dinucleotide ate - reduced | HMDB | Nicotinamide-adenine-dinucleotide-orate | HMDB | Nicotinamide-adenine-dinucleotide-oric acid | HMDB | reduced Codehydrase II | hmdb | reduced Coenzyme II | hmdb | reduced Cozymase II | hmdb | Reduced triopyridine nucleotide | HMDB | Triopyridine nucleotide reduced | HMDB |
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Predicted Properties | |
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Chemical Formula | C21H30N7O17P3 |
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IUPAC name | {[(2S,3S,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-[({[({[(2S,3R,4S,5S)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid |
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InChI Identifier | InChI=1S/C21H30N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1,3-4,7-8,10-11,13-16,20-21,29-31H,2,5-6H2,(H2,23,32)(H,36,37)(H,38,39)(H2,22,24,25)(H2,33,34,35)/t10-,11-,13-,14-,15-,16-,20-,21-/m0/s1 |
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InChI Key | ACFIXJIJDZMPPO-NCHANQSKSA-N |
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Isomeric 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](OP(O)(O)=O)[C@H]2O)N2C=NC3=C(N)N=CN=C23)[C@H](O)[C@@H]1O |
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Average Molecular Weight | 745.4209 |
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Monoisotopic Molecular Weight | 745.091102105 |
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Classification |
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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 2',5'-bisphosphate
- Purine ribonucleoside bisphosphate
- Purine ribonucleoside diphosphate
- Nicotinamide-nucleotide
- Pentose phosphate
- Pentose-5-phosphate
- N-glycosyl compound
- Glycosyl compound
- Monosaccharide phosphate
- 6-aminopurine
- N-substituted nicotinamide
- Organic pyrophosphate
- Imidazopyrimidine
- Purine
- Monoalkyl phosphate
- Dihydropyridine
- Aminopyrimidine
- Organic phosphoric acid derivative
- Pyrimidine
- N-substituted imidazole
- Hydropyridine
- Alkyl phosphate
- Phosphoric acid ester
- Imidolactam
- Monosaccharide
- Vinylogous amide
- Heteroaromatic compound
- Tetrahydrofuran
- Azole
- Imidazole
- Amino acid or derivatives
- Carboxamide group
- Secondary alcohol
- Primary carboxylic acid amide
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Carboxylic acid derivative
- Enamine
- Hydrocarbon derivative
- Organic oxygen compound
- Amine
- Organopnictogen compound
- Carbonyl group
- Organic oxide
- Primary amine
- Alcohol
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | NADPH, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-004j-9421780200-89062ec4778392672634 | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-02tj-1838493720-b38b37650e8976905bb0 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0a4r-0841393100-6e4cbc8ac576e3e8b195 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0550-2694875730-0dc522520957880672cb | 2012-07-24 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0921104300-c1952197674952109d2c | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0901000000-31adeef6c90e9070dfa4 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-000i-0920000000-e29dcab04f59f9c7189c | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0036-6900111800-ab3c73d03c4430e1b644 | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-003r-4901100000-96b551ade48c419935ed | 2017-09-01 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-057i-5900000000-0898019fd8b891d5245e | 2017-09-01 | View Spectrum |
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NMR | Type | Description | | View |
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1D NMR | 13C NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | | Spectrum | 2D NMR | [1H, 1H]-TOCSY 2D NMR Spectrum (experimental) | | Spectrum |
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External Links |
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ChemSpider ID | 17215925 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00005 |
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Pubchem Compound ID | 22833512 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 16474 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB00221 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 33486 |
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KNApSAcK ID | Not Available |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | NADPH |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Cytochrome P450, family 1, subfamily A, polypeptide 1 | CYP1A1 | A0N0X8 | Cytochrome P450 2D6 | CYP2D6 | Q6NWU0 | Aminoadipate-semialdehyde synthase | AASS | A4D0W4 | Alcohol dehydrogenase [NADP(+)] | AKR1A1 | P14550 | Fatty acyl-CoA reductase 2 | FAR2 | Q96K12 | Glucose-6-phosphate 1-dehydrogenase | G6PD | P11413 | 6-phosphogluconate dehydrogenase, decarboxylating | PGD | P52209 | Dehydrogenase/reductase SDR family member 4 | DHRS4 | Q9BTZ2 | L-xylulose reductase | DCXR | Q7Z4W1 | Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | DHDH | Q9UQ10 | 7-dehydrocholesterol reductase | DHCR7 | Q9UBM7 | Glutaredoxin-1 | GLRX | P35754 | Fatty acid synthase | FASN | P49327 | NOS1 mutant | NOS1 | B3VK56 | Fatty acyl-CoA reductase 1 | FAR1 | Q8WVX9 | Delta-1-pyrroline-5-carboxylate synthase | ALDH18A1 | P54886 | GMP reductase 2 | GMPR2 | Q9P2T1 | GMP reductase 1 | GMPR | P36959 | 3-hydroxy-3-methylglutaryl-coenzyme A reductase | HMGCR | P04035 | Delta(14)-sterol reductase | TM7SF2 | O76062 | 3-oxo-5-beta-steroid 4-dehydrogenase | AKR1D1 | P51857 | 3-oxo-5-alpha-steroid 4-dehydrogenase 2 | SRD5A2 | P31213 | 3-oxo-5-alpha-steroid 4-dehydrogenase 1 | SRD5A1 | P18405 | Testosterone 17-beta-dehydrogenase 3 | HSD17B3 | P37058 | Polyprenol reductase | SRD5A3 | Q9H8P0 | Peroxisomal trans-2-enoyl-CoA reductase | PECR | Q9BY49 | C-1-tetrahydrofolate synthase, cytoplasmic | MTHFD1 | P11586 | Monofunctional C1-tetrahydrofolate synthase, mitochondrial | MTHFD1L | Q6UB35 | Acyl-CoA synthetase family member 4 | AASDH | Q4L235 | L-aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferase | AASDHPPT | Q9NRN7 | Cytosolic 10-formyltetrahydrofolate dehydrogenase | ALDH1L1 | O75891 | Mitochondrial 10-formyltetrahydrofolate dehydrogenase | ALDH1L2 | Q3SY69 | Putative uncharacterized protein DKFZp686B0215 | DKFZp686B0215 | Q5HYI4 | Cytochrome P450, family 21, subfamily A, polypeptide 2 | CYP21A2 | Q08AG9 | Retinol dehydrogenase 8 | RDH8 | Q9NYR8 | Retinol dehydrogenase 11 | RDH11 | Q8TC12 | Retinol dehydrogenase 10 | RDH10 | Q8IZV5 | Short-chain dehydrogenase/reductase 3 | DHRS3 | O75911 | Dihydrofolate reductase | DHFR | P00374 | NADPH oxidase activator 1 | NOXA1 | Q86UR1 | Aflatoxin B1 aldehyde reductase member 2 | AKR7A2 | O43488 | GDP-L-fucose synthase | TSTA3 | Q13630 | Sepiapterin reductase | SPR | P35270 | Dehydrogenase/reductase SDR family member 9 | DHRS9 | Q9BPW9 | Corticosteroid 11-beta-dehydrogenase isozyme 1 | HSD11B1 | P28845 | Carbonyl reductase [NADPH] 1 | CBR1 | P16152 | Carbonyl reductase [NADPH] 3 | CBR3 | O75828 | 2,4-dienoyl-CoA reductase, mitochondrial | DECR1 | Q16698 | Peroxisomal 2,4-dienoyl-CoA reductase | DECR2 | Q9NUI1 | 3-ketodihydrosphingosine reductase | KDSR | Q06136 | Very-long-chain enoyl-CoA reductase | TECR | Q9NZ01 | Neutrophil cytosol factor 2 | NCF2 | P19878 | Neutrophil cytosol factor 4 | NCF4 | Q15080 | Neutrophil cytosol factor 1 | NCF1 | P14598 | Retinol dehydrogenase 12 | RDH12 | Q96NR8 | Retinol dehydrogenase 14 | RDH14 | Q9HBH5 | Oxidoreductase HTATIP2 | HTATIP2 | Q9BUP3 | Putative neutrophil cytosol factor 1B | NCF1B | A6NI72 | Putative neutrophil cytosol factor 1C | NCF1C | A8MVU1 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | Not Available |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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