Record Information
Version1.0
Creation date2011-09-21 00:04:58 UTC
Update date2018-01-23 20:19:36 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
Adenine-nicotinamide dinucleotide phosphateHMDB
b-NADPHMDB
b-TPNHMDB
beta-NADPHMDB
beta-TPNHMDB
Codehydrase IIHMDB
Codehydrogenase IIHMDB
Coenzyme IIHMDB
Cozymase IIHMDB
NAD phosphateHMDB
Nicotinamide-adenine dinucleotide phosphateHMDB
Dinucleotide phosphate, nicotinamide-adenineHMDB
NADPHHMDB
Nucleotide, triphosphopyridineHMDB
Phosphate, nicotinamide-adenine dinucleotideHMDB
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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 (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
  • Pyridine nucleotide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Nicotinamide
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyridinium
  • Pyridine
  • Imidolactam
  • Imidazole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Azole
  • Secondary alcohol
  • Carboximidic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboximidic acid
  • Primary amine
  • Hydrocarbon derivative
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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, Positivesplash10-056s-9231470300-9e17b00343fde5427c48View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0219003700-2f52e3c5db41066a112cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-0301009000-a3d0c464e56f6e320c80View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0000090000-c18a7719161c63a71938View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0000009000-1dde5b221786fe375304View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-00dl-0209000700-02057593d6470f6a2075View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-0301109000-bf4996084c09a9176489View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0uk9-0301009000-b3e8d304dfdc4711e0ceView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positivesplash10-0udi-0000009000-384d275a638928dd40f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00dl-0000229600-bd164bae0cc54f45b961View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-004i-0027900000-25e0180b7638ed18e207View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0011953000-c328377f842fac60b55eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-0ec3670e706b086d382aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00dl-0000109700-df2a731fd5f55e9e7a8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-0011953000-981d13d6b50f18ebc910View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-f9526262833104be0a2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-00di-0000009000-c0cedd489befb2073370View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-1000000900-8e9739738c1e21ad0cfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000t-0000000900-5168590e47e1994b82e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006y-2910001000-5066541857e9b5d8bbbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1000000900-b0b6966dffa0668455c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-7100000900-fb944feb508487f250a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-005a-9100000000-2fe9ef99497bf15191d1View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
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
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