Record Information
Version1.0
Creation date2015-05-07 20:53:40 UTC
Update date2019-11-26 03:22:06 UTC
Primary IDFDB031054
Secondary Accession Numbers
  • FDB021908
Chemical Information
FooDB NameNADP+
DescriptionNadp+, also known as nicotinamide adenine dinucleotide phosphate or nadp, is a member of the class of compounds known as (5'->5')-dinucleotides (5'->5')-dinucleotides are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. Nadp+ is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Nadp+ can be found in a number of food items such as small-leaf linden, redcurrant, root vegetables, and fenugreek, which makes nadp+ a potential biomarker for the consumption of these food products. Nadp+ can be found primarily in blood, as well as throughout all human tissues. Nadp+ exists in all eukaryotes, ranging from yeast to humans. In humans, nadp+ is involved in several metabolic pathways, some of which include folate malabsorption, hereditary, carprofen action pathway, valdecoxib action pathway, and glutathione metabolism. Nadp+ is also involved in several metabolic disorders, some of which include monoamine oxidase-a deficiency (MAO-A), apparent mineralocorticoid excess syndrome, hyperprolinemia type I, and hyperphenylalaninemia due to dhpr-deficiency. Moreover, nadp+ is found to be associated with pellagra. Nicotinamide adenine dinucleotide phosphate, abbreviated NADP+ or, in older notation, TPN (triphosphopyridine nucleotide), is a cofactor used in anabolic reactions, such as lipid and nucleic acid synthesis, which require NADPH as a reducing agent .
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
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 (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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
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 IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference