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
References
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Binding thermodynamics of statins to HMG-CoA reductase.
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Compared effect of immunosuppressive drugs cyclosporine A and rapamycin on cholesterol homeostasis key enzymes CYP27A1 and HMG-CoA reductase.
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3. Ingebritsen TS, Parker RA, Gibson DM. (1981)
Regulation of liver hydroxymethylglutaryl-CoA reductase by a bicyclic phosphorylation system.
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4. Istvan ES, Deisenhofer J. (2000)
The structure of the catalytic portion of human HMG-CoA reductase.
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5. Ness GC, Eales SJ, Pendleton LC, Smith M. (1985)
Activation of rat liver microsomal 3-hydroxy-3-methylglutaryl coenzyme A reductase by NADPH. Effects of dietary treatments.
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Biphasic regulation of HMG-CoA reductase expression and activity during wound healing and its functional role in the control of keratinocyte angiogenic and proliferative responses.
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7. Seiki S, Frishman WH. (2009)
Pharmacologic inhibition of squalene synthase and other downstream enzymes of the cholesterol synthesis pathway: a new therapeutic approach to treatment of hypercholesterolemia.
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8. Shechter I, Klinger E, Rucker ML, Engstrom RG, Spirito JA, Islam MA, Boettcher BR, Weinstein DB. (1992)
Solubilization, purification, and characterization of a truncated form of rat hepatic squalene synthetase.
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