NADPH   Click here for help

GtoPdb Ligand ID: 3041

Synonyms: reduced nicotinamide adenine dinucleotide phosphate | TPNH
Compound class: Metabolite or derivative
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 23
Hydrogen bond donors 9
Rotatable bonds 13
Topological polar surface area 393.58
Molecular weight 745.09
XLogP -6.65
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC1C(O)C(OC1N1C=CCC(=C1)C(=O)N)COP(=O)(OP(=O)(OCC1OC(C(C1O)OP(=O)(O)O)n1cnc2c1ncnc2N)O)O
Isomeric SMILES O[C@H]1[C@@H](O)[C@@H](O[C@@H]1N1C=CCC(=C1)C(=O)N)COP(=O)(OP(=O)(OC[C@@H]1O[C@@H]([C@H]([C@H]1O)OP(=O)(O)O)n1cnc2c1ncnc2N)O)O
InChI InChI=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 Key ACFIXJIJDZMPPO-NCHANQSKSA-N
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
hydroxymethylglutaryl-CoA reductase 1.1.1.34 (S)-3-hydroxy-3-methylglutaryl-CoA + NADPH -> (R)-mevalonate + coenzyme A + NADP+ 1
squalene synthase 8
CBR1 1.1.1.189 PGE2 + NADP+ = PGF2α + NADPH + H+
squalene monooxygenase 1.14.13.132 H+ + NADPH + O2 + squalene = H2O + NADP+ + (S)-2,3-epoxysqualene
AKR1C3 1.1.1.188 PGD2 + NADP+ = PGF2α + NADPH + H+
3-ketodihydrosphingosine reductase 1.1.1.102 3-Ketosphinganine + NADPH -> NADP+ + dihydrosphingosine
aldehyde dehydrogenase 9 family member A1 1.2.1.47 4-Trimethylammoniobutanal + NAD + H2O = 4-trimethylammoniobutanoate + NADPH + 2H+
Cofactor in Enzyme Reactions
Enzyme Reference
hydroxymethylglutaryl-CoA reductase 1-6
squalene synthase 7
Endothelial NOS
Inducible NOS
Neuronal NOS
γ-Glutamyl carboxylase
CYP3A4
3-ketodihydrosphingosine reductase
iodotyrosine deiodinase
Ligand mentioned in the following text fields
Haem oxygenase overview