NADP+
Athanor · official
C21H28N7O17P3 · 743.4 g/mol
IUPAC name: [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
Also called nicotinamide adenine dinucleotide phosphate, TPN
WarningCauses skin irritation · Causes serious eye irritation · May cause respiratory irritationNames and identifiers
- IUPAC name
- [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
- Synonyms
- nicotinamide adenine dinucleotide phosphate, TPN, coenzyme II
+ 37 more
NADP, triphosphopyridine nucleotide, Codehydrogenase II, NAD phosphate, Cozymase II, Nadide phosphate, TPN (nucleotide), Nicotinamide-adenine dinucleotide phosphate, BY8P107XEP, CHEBI:44409, beta-nicotinamide adenine dinucleotide phosphate, DTXSID50889327, Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'-5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt, beta-NADP+, [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate, CHEBI:18009, (((2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl)methoxy-hydroxyphosphoryl) ((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl)methyl phosphate, ((2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl)methyl (((2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl)methoxy-hydroxyphosphoryl) hydrogen phosphate, RefChem:831677, Nucleotide, Triphosphopyridine, CHEBI:25523, DTXCID801028590, Dinucleotide Phosphate, Nicotinamide-Adenine, Phosphate, Nicotinamide-Adenine Dinucleotide, 1-((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, 200-178-1, Codehydrase II, beta-NADP, Adenine-nicotinamide dinucleotide phosphate, beta-TPN, NADP zwitterion, b-NADP, BRN 3885115, 1-((2R,3R,4S,5R)-5-((((((((2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)oxidophosphoryl)oxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-3-carbamoylpyridin-1-ium, b-Nicotinamide adenine dinucleotide phosphate, TPN-ox, Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), 5'->'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium hydroxide, inner salt
- Molecular formula
- C21H28N7O17P3
- Empirical formula
- C21H28N7O17P3
- Molecular weight
- 743.4 g/mol
- Exact mass
- 743.07545
- CAS number
- 53-59-8
- PubChem CID
- 5885
- Canonical SMILES
- C1=CC(=C[N+](=C1)C2C(C(C(O2)COP(=O)([O-])OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O)C(=O)N
- Isomeric SMILES
- C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)([O-])OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O)C(=O)N
- InChI
- InChI=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)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
- InChIKey
- XJLXINKUBYWONI-NNYOXOHSSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 48
- Rings
- 5
- Aromatic rings
- 3
- Fraction sp³ carbons (Fsp3)
- 0.48
- H-bond donors
- 8
- H-bond acceptors
- 18 computed here · PubChem 21
- Rotatable bonds
- 13
- TPSA (Ų)
- 367.6 computed here · PubChem 368
- Formal charge
- 0
- XLogP3
- -7.1 PubChem
- Complexity
- 1290 PubChem
- Stereocenters
- 8 defined, 2 undefinedCIP: C10: R · C12: R · P15: undefined · P19: undefined · C24: R · C26: R · C37: R · C43: R · C45: S · C47: R
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C33.93%
- H3.80%
- N13.19%
- O36.59%
- P12.50%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- -3.53 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -1.6 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 5.54 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 743.41
- log P ≤ 5 (Crippen): -3.53
- H-bond donors ≤ 5: 8
- H-bond acceptors ≤ 10: 18
Breaks 3 of the four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Warning
Most widely reported: 2 company reports to ECHA. Source [1].
- Harmful or irritant
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements: P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Safety data sheets on the supplier’s page: 10X CHEM, Alfa Chemistry, eMolecules.
Always read the supplier’s safety data sheet before working with it.
Spectra
- 1H NMRHuman Metabolome Database (HMDB) (Varian · 500 MHz · Water) · Human Metabolome Database (HMDB) (Bruker · D2O)
- 13C NMRHuman Metabolome Database (HMDB) (Bruker · 125 MHz · Water) · Human Metabolome Database (HMDB) (Bruker · D2O)
- 31P NMRSpectraBase (Bruker HX-90)
- 1H-1H NMRHuman Metabolome Database (HMDB)
- 1H-13C NMRHuman Metabolome Database (HMDB) (Bruker · 600 MHz · Water)
- MS-MSHuman Metabolome Database (HMDB) (LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) · Positive) · Human Metabolome Database (HMDB) (LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) · Positive) · Human Metabolome Database (HMDB) (LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) · Positive) · Human Metabolome Database (HMDB) (LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) · Positive) · Human Metabolome Database (HMDB) (LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) · Positive) · Human Metabolome Database (HMDB) (LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) · Positive)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [2]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [3]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [4]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.