Record Information
Version1.0
Creation date2011-09-21 00:04:59 UTC
Update date2019-11-27 17:42:27 UTC
Primary IDFDB021909
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNADPH
DescriptionNicotinamide 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.
CAS Number53-57-6
Structure
Thumb
Synonyms
SynonymSource
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamideHMDB
2'-(Dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamideHMDB
b-NADPHHMDB
b-Nicotinamide-adenine-dinucleotide-phosphorateHMDB
b-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
beta-NADPHHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphorateHMDB
beta-Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Dihydrocodehydrogenase IIHMDB
Dihydronicotinamide adenine dinucleotide phosphateHMDB
Dihydronicotinamide adenine dinucleotide-pHMDB
Dihydrotriphosphopyridine nucleotide reducedHMDB
NADP-reducedHMDB
Nicotinamide adenine dinucleotide phosphate - reducedHMDB
Nicotinamide-adenine-dinucleotide-phosphorateHMDB
Nicotinamide-adenine-dinucleotide-phosphoric acidHMDB
Reduced codehydrase IIHMDB
Reduced coenzyme IIHMDB
Reduced cozymase IIHMDB
Reduced triphosphopyridine nucleotideHMDB
Triphosphopyridine nucleotide reducedHMDB
2'-(Dihydrogen ate) 5'-(trihydrogen pyroate) adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamideHMDB
2'-(Dihydrogen ate) 5'-(trihydrogen pyroate) adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamideHMDB
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-b-D-ribofuranosylnicotinamidehmdb
2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate) Adenosine 5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosylnicotinamidehmdb
Adenosine 5'-(trihydrogen diate) 2'-(dihydrogen ate) p'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamideHMDB
Adenosine 5'-(trihydrogen diate) 2'-(dihydrogen ate) p'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamideHMDB
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamidehmdb
Adenosine 5'-(trihydrogen diphosphate) 2'-(dihydrogen phosphate) P'-5'-ester with 1,4-dihydro-1-beta-delta-ribofuranosyl-3-pyridinecarboxamidehmdb
b-Nicotinamide-adenine-dinucleotide-orateHMDB
b-Nicotinamide-adenine-dinucleotide-oric acidHMDB
beta-Nicotinamide-adenine-dinucleotide-orateHMDB
beta-Nicotinamide-adenine-dinucleotide-oric acidHMDB
Dihydronicotinamide adenine dinucleotide ateHMDB
dihydronicotinamide adenine dinucleotide phosphatehmdb
dihydronicotinamide adenine dinucleotide-Phmdb
Dihydrotriopyridine nucleotide reducedHMDB
dihydrotriphosphopyridine nucleotide reducedhmdb
NADPHhmdb
Nicotinamide adenine dinucleotide ate - reducedHMDB
Nicotinamide-adenine-dinucleotide-orateHMDB
Nicotinamide-adenine-dinucleotide-oric acidHMDB
reduced Codehydrase IIhmdb
reduced Coenzyme IIhmdb
reduced Cozymase IIhmdb
Reduced triopyridine nucleotideHMDB
Triopyridine nucleotide reducedHMDB
Predicted Properties
PropertyValueSource
Water Solubility5.45 g/LALOGPS
logP-1.1ALOGPS
logP-6.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)4ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area364.15 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity153.87 m³·mol⁻¹ChemAxon
Polarizability63.02 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H30N7O17P3
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
InChI IdentifierInChI=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
InChI KeyACFIXJIJDZMPPO-NCHANQSKSA-N
Isomeric SMILESNC(=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
Average Molecular Weight745.4209
Monoisotopic Molecular Weight745.091102105
Classification
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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class(5'->5')-dinucleotides
Sub ClassNot Available
Direct Parent(5'->5')-dinucleotides
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004j-9421780200-89062ec4778392672634View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-02tj-1838493720-b38b37650e8976905bb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4r-0841393100-6e4cbc8ac576e3e8b195View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0550-2694875730-0dc522520957880672cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0921104300-c1952197674952109d2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901000000-31adeef6c90e9070dfa4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0920000000-e29dcab04f59f9c7189cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0036-6900111800-ab3c73d03c4430e1b644View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4901100000-96b551ade48c419935edView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900000000-0898019fd8b891d5245eView in MoNA
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID17215925
ChEMBL IDNot Available
KEGG Compound IDC00005
Pubchem Compound ID22833512
Pubchem Substance IDNot Available
ChEBI ID16474
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00221
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33486
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNADPH
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Cytochrome P450, family 1, subfamily A, polypeptide 1CYP1A1A0N0X8
Cytochrome P450 2D6CYP2D6Q6NWU0
Aminoadipate-semialdehyde synthaseAASSA4D0W4
Alcohol dehydrogenase [NADP(+)]AKR1A1P14550
Fatty acyl-CoA reductase 2FAR2Q96K12
Glucose-6-phosphate 1-dehydrogenaseG6PDP11413
6-phosphogluconate dehydrogenase, decarboxylatingPGDP52209
Dehydrogenase/reductase SDR family member 4DHRS4Q9BTZ2
L-xylulose reductaseDCXRQ7Z4W1
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenaseDHDHQ9UQ10
7-dehydrocholesterol reductaseDHCR7Q9UBM7
Glutaredoxin-1GLRXP35754
Fatty acid synthaseFASNP49327
NOS1 mutantNOS1B3VK56
Fatty acyl-CoA reductase 1FAR1Q8WVX9
Delta-1-pyrroline-5-carboxylate synthaseALDH18A1P54886
GMP reductase 2GMPR2Q9P2T1
GMP reductase 1GMPRP36959
3-hydroxy-3-methylglutaryl-coenzyme A reductaseHMGCRP04035
Delta(14)-sterol reductaseTM7SF2O76062
3-oxo-5-beta-steroid 4-dehydrogenaseAKR1D1P51857
3-oxo-5-alpha-steroid 4-dehydrogenase 2SRD5A2P31213
3-oxo-5-alpha-steroid 4-dehydrogenase 1SRD5A1P18405
Testosterone 17-beta-dehydrogenase 3HSD17B3P37058
Polyprenol reductaseSRD5A3Q9H8P0
Peroxisomal trans-2-enoyl-CoA reductasePECRQ9BY49
C-1-tetrahydrofolate synthase, cytoplasmicMTHFD1P11586
Monofunctional C1-tetrahydrofolate synthase, mitochondrialMTHFD1LQ6UB35
Acyl-CoA synthetase family member 4AASDHQ4L235
L-aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferaseAASDHPPTQ9NRN7
Cytosolic 10-formyltetrahydrofolate dehydrogenaseALDH1L1O75891
Mitochondrial 10-formyltetrahydrofolate dehydrogenaseALDH1L2Q3SY69
Putative uncharacterized protein DKFZp686B0215DKFZp686B0215Q5HYI4
Cytochrome P450, family 21, subfamily A, polypeptide 2CYP21A2Q08AG9
Retinol dehydrogenase 8RDH8Q9NYR8
Retinol dehydrogenase 11RDH11Q8TC12
Retinol dehydrogenase 10RDH10Q8IZV5
Short-chain dehydrogenase/reductase 3DHRS3O75911
Dihydrofolate reductaseDHFRP00374
NADPH oxidase activator 1NOXA1Q86UR1
Aflatoxin B1 aldehyde reductase member 2AKR7A2O43488
GDP-L-fucose synthaseTSTA3Q13630
Sepiapterin reductaseSPRP35270
Dehydrogenase/reductase SDR family member 9DHRS9Q9BPW9
Corticosteroid 11-beta-dehydrogenase isozyme 1HSD11B1P28845
Carbonyl reductase [NADPH] 1CBR1P16152
Carbonyl reductase [NADPH] 3CBR3O75828
2,4-dienoyl-CoA reductase, mitochondrialDECR1Q16698
Peroxisomal 2,4-dienoyl-CoA reductaseDECR2Q9NUI1
3-ketodihydrosphingosine reductaseKDSRQ06136
Very-long-chain enoyl-CoA reductaseTECRQ9NZ01
Neutrophil cytosol factor 2NCF2P19878
Neutrophil cytosol factor 4NCF4Q15080
Neutrophil cytosol factor 1NCF1P14598
Retinol dehydrogenase 12RDH12Q96NR8
Retinol dehydrogenase 14RDH14Q9HBH5
Oxidoreductase HTATIP2HTATIP2Q9BUP3
Putative neutrophil cytosol factor 1BNCF1BA6NI72
Putative neutrophil cytosol factor 1CNCF1CA8MVU1
Pathways
NameSMPDB LinkKEGG Link
Arachidonic Acid MetabolismSMP00075 map00590
Ethanol DegradationSMP00449 Not Available
Folate MetabolismSMP00053 map00670
Glucose-Alanine CycleSMP00127 Not Available
Glutathione MetabolismSMP00015 map00480
Glycerolipid MetabolismSMP00039 map00561
Histidine MetabolismSMP00044 map00340
Phytanic Acid Peroxisomal OxidationSMP00450 Not Available
Plasmalogen SynthesisSMP00479 Not Available
Pterine BiosynthesisSMP00005 map00790
Transfer of Acetyl Groups into MitochondriaSMP00466 Not Available
Vitamin K MetabolismSMP00464 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference