Record Information
Version1.0
Creation date2011-09-21 00:04:58 UTC
Update date2020-04-21 18:03:36 UTC
Primary IDFDB021908
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNADP
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.) Hydrogen carrier in biochemical redox systems. In the hexose monophosphoric acid system it is reduced to Dihydrocoenzyme II and reoxidation in the presence of flavoproteins (Dictionary of Organic Compounds) [HMDB]. NADP is found in many foods, some of which are black walnut, lemon verbena, savoy cabbage, and silver linden.
CAS Number53-59-8
Structure
Thumb
Synonyms
SynonymSource
beta-Nicotinamide adenine dinucleotide phosphateChEBI
NADP+ChEBI
Nicotinamide adenine dinucleotide phosphateChEBI
Oxidized nicotinamide-adenine dinucleotide phosphateChEBI
TPNChEBI
Triphosphopyridine nucleotideChEBI
beta-NADP+Kegg
b-Nicotinamide adenine dinucleotide phosphateGenerator
b-Nicotinamide adenine dinucleotide phosphoric acidGenerator
beta-Nicotinamide adenine dinucleotide phosphoric acidGenerator
Β-nicotinamide adenine dinucleotide phosphateGenerator
Β-nicotinamide adenine dinucleotide phosphoric acidGenerator
Nicotinamide adenine dinucleotide phosphoric acidGenerator
Oxidized nicotinamide-adenine dinucleotide phosphoric acidGenerator
b-NADP+Generator
Β-nadp+Generator
Coenzyme IIMeSH
Dinucleotide phosphate, nicotinamide-adenineMeSH
NADPHMeSH
Nicotinamide-adenine dinucleotide phosphateMeSH
Nucleotide, triphosphopyridineMeSH
Phosphate, nicotinamide-adenine dinucleotideMeSH
Adenine-nicotinamide dinucleotide phosphateHMDB
b-NADPHMDB
b-TPNHMDB
beta-NADPHMDB
beta-TPNHMDB
Codehydrase IIHMDB
Codehydrogenase IIHMDB
Cozymase IIHMDB
NAD phosphateHMDB
Adenine-nicotinamide dinucleotide ateHMDB
b-Nicotinamide adenine dinucleotide ateGenerator
b-Nicotinamide adenine dinucleotide ic acidGenerator
beta-Nicotinamide adenine dinucleotide ateChEBI
beta-Nicotinamide adenine dinucleotide ic acidGenerator
NAD ateHMDB
NADPhmdb
Nicotinamide adenine dinucleotide ateChEBI
Nicotinamide adenine dinucleotide ic acidGenerator
Nicotinamide-adenine dinucleotide ateHMDB
Oxidized nicotinamide-adenine dinucleotide ateChEBI
Oxidized nicotinamide-adenine dinucleotide ic acidGenerator
Triopyridine nucleotideChEBI
β-nicotinamide adenine dinucleotide ateGenerator
β-nicotinamide adenine dinucleotide ic acidGenerator
Predicted Properties
PropertyValueSource
Water Solubility4.15 g/LALOGPS
logP-0.78ALOGPS
logP-10ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)4ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area364.79 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity152.87 m³·mol⁻¹ChemAxon
Polarizability60.89 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H29N7O17P3
IUPAC name1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-1lambda5-pyridin-1-ylium
InChI IdentifierInChI=1S/C21H28N7O17P3/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/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/p+1/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
InChI KeyXJLXINKUBYWONI-NNYOXOHSSA-O
Isomeric SMILESNC(=O)C1=C[N+](=CC=C1)[C@@H]1O[C@H](CO[P@](O)(=O)O[P@](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 Weight744.4129
Monoisotopic Molecular Weight744.083277073
Classification
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Hydroxamic acid
  • Amino acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Amine
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNADP, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-056s-9231470300-9e17b00343fde5427c48Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0219003700-2f52e3c5db41066a112cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-0301009000-a3d0c464e56f6e320c80Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0000090000-c18a7719161c63a71938Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0000009000-1dde5b221786fe375304Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0209000700-02057593d6470f6a2075Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-0301109000-bf4996084c09a9176489Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-0301009000-b3e8d304dfdc4711e0ceSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0000009000-384d275a638928dd40f1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00dl-0000229600-bd164bae0cc54f45b961Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0027900000-25e0180b7638ed18e207Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0011953000-c328377f842fac60b55eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-0ec3670e706b086d382aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00dl-0000109700-df2a731fd5f55e9e7a8eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0011953000-981d13d6b50f18ebc910Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-f9526262833104be0a2eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-c0cedd489befb2073370Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1000000900-8e9739738c1e21ad0cfbSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0000000900-5168590e47e1994b82e9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-2910001000-5066541857e9b5d8bbbfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1000000900-b0b6966dffa0668455c4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-7100000900-fb944feb508487f250a5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005a-9100000000-2fe9ef99497bf15191d1Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID5675
ChEMBL IDNot Available
KEGG Compound IDC00006
Pubchem Compound ID5886
Pubchem Substance IDNot Available
ChEBI ID13397
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00217
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33488
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNADP
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
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
14 kDa phosphohistidine phosphatasePHPT1Q9NRX4
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
GDP-mannose 4,6 dehydrataseGMDSO60547
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
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
Thioredoxin domain-containing protein 2TXNDC2Q86VQ3
Very-long-chain enoyl-CoA reductaseTECRQ9NZ01
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
Nicotinate and Nicotinamide MetabolismSMP00048 map00760
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference