ID: ALA2364573
Max Phase: Preclinical
Molecular Formula: C21H28N7O17P3
Molecular Weight: 743.41
Molecule Type: Small molecule
Associated Items:
Synonyms (4): NADP | NADP+ | NADPH | Nicotinamide Adenine Dinucleotide Phosphate
Synonyms from Alternative Forms(4):
Canonical SMILES: NC(=O)c1ccc[n+]([C@H]2O[C@@H](COP(=O)([O-])OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](OP(=O)(O)O)[C@@H]3O)[C@H](O)[C@@H]2O)c1
Standard 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+/m0/s1
Standard InChI Key: XJLXINKUBYWONI-DQQFMEOOSA-N
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| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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| Molecular Weight: 743.41 | Molecular Weight (Monoisotopic): 743.0755 | AlogP: -3.53 | #Rotatable Bonds: 13 |
| Polar Surface Area: 367.62 | Molecular Species: ACID | HBA: 19 | HBD: 8 |
| #RO5 Violations: 3 | HBA (Lipinski): 24 | HBD (Lipinski): 10 | #RO5 Violations (Lipinski): 3 |
| CX Acidic pKa: 0.66 | CX Basic pKa: 4.80 | CX LogP: -10.61 | CX LogD: -15.52 |
| Aromatic Rings: 3 | Heavy Atoms: 48 | QED Weighted: 0.06 | Np Likeness Score: 0.78 |
| 1. Taira K, Benkovic SJ.. (1988) Evaluation of the importance of hydrophobic interactions in drug binding to dihydrofolate reductase., 31 (1): [PMID:3275776] [10.1021/jm00396a019] |
| 2. McKie JH, Douglas KT, Chan C, Roser SA, Yates R, Read M, Hyde JE, Dascombe MJ, Yuthavong Y, Sirawaraporn W.. (1998) Rational drug design approach for overcoming drug resistance: application to pyrimethamine resistance in malaria., 41 (9): [PMID:9554869] [10.1021/jm970845u] |
| 3. Mautner HG, Merrill RE, Currier SF, Harvey G.. (1981) Interaction of aromatic dyes with the coenzyme A binding site of choline acetyltransferase., 24 (12): [PMID:7310833] [10.1021/jm00144a035] |
| 4. Evenson DA, Adams J, McIvor RS, Wagner CR.. (1996) Methotrexate resistance of mouse dihydrofolate reductase: effect of substitution of phenylalanine-31 by serine or tryptophan., 39 (9): [PMID:8627598] [10.1021/jm950793d] |
| 5. Wagner CR, Benkovic SJ.. (1992) Probing the molecular basis of resistance to pyrimethamine by site-directed mutagenesis., 35 (15): [PMID:1495020] [10.1021/jm00093a026] |
| 6. Ciulli A, Williams G, Smith AG, Blundell TL, Abell C.. (2006) Probing hot spots at protein-ligand binding sites: a fragment-based approach using biophysical methods., 49 (16): [PMID:16884311] [10.1021/jm060490r] |
Source(1):
