| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ID: ALA140448
Max Phase: Preclinical
Molecular Formula: C22H21N5O7
Molecular Weight: 467.44
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Nc1nc(O)c2cc(CN(C=O)c3ccc(C(=O)NC(CCC(=O)O)C(=O)O)cc3)ccc2n1
Standard InChI: InChI=1S/C22H21N5O7/c23-22-25-16-6-1-12(9-15(16)20(32)26-22)10-27(11-28)14-4-2-13(3-5-14)19(31)24-17(21(33)34)7-8-18(29)30/h1-6,9,11,17H,7-8,10H2,(H,24,31)(H,29,30)(H,33,34)(H3,23,25,26,32)
Standard InChI Key: QHUBQNFYSLRYQG-UHFFFAOYSA-N
Associated Targets(Human)
GAR transformylase 531 Activities
Dihydrofolate reductase 3072 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Associated Targets(non-human)
Thymidylate synthase 842 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Thymidylate synthase 501 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Dihydrofolate reductase 93 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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Molecule Features
| 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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 467.44 | Molecular Weight (Monoisotopic): 467.1441 | AlogP: 1.13 | #Rotatable Bonds: 10 |
| Polar Surface Area: 196.04 | Molecular Species: ACID | HBA: 8 | HBD: 5 |
| #RO5 Violations: 0 | HBA (Lipinski): 12 | HBD (Lipinski): 6 | #RO5 Violations (Lipinski): 2 |
| CX Acidic pKa: 3.13 | CX Basic pKa: 2.64 | CX LogP: 0.62 | CX LogD: -5.56 |
| Aromatic Rings: 3 | Heavy Atoms: 34 | QED Weighted: 0.27 | Np Likeness Score: -0.43 |
References
| 1. Caperelli CA, Conigliaro J.. (1986) Synthesis of 10-acetyl-5,8-dideazafolic acid: a potent inhibitor of glycinamide ribonucleotide transformylase., 29 (10): [PMID:3761327] [10.1021/jm00160a056] |
| 2. Hynes JB, Patil SA, Tomazic A, Kumar A, Pathak A, Tan XH, Li XQ, Ratnam M, Delcamp TJ, Freisheim JH.. (1988) Inhibition of murine thymidylate synthase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin., 31 (2): [PMID:3339615] [10.1021/jm00397a031] |
| 3. Crippen GM.. (1980) Quantitative structure-activity relationships by distance geometry: systematic analysis of dihydrofolate reductase inhibitors., 23 (6): [PMID:7392027] [10.1021/jm00180a004] |
| 4. Ghose AK, Crippen GM.. (1982) Quantitative structure-activity relationship by distance geometry: quinazolines as dihydrofolate reductase inhibitors., 25 (8): [PMID:7120278] [10.1021/jm00350a003] |
| 5. Chen BK, Horváth C, Bertino JR.. (1979) Multivariate analysis and quantitative structure-activity relationships. Inhibition of dihydrofolate reductase and thymidylate synthetase by quinazolines., 22 (5): [PMID:110930] [10.1021/jm00191a005] |
| 6. Hansch C, Fukunaga JY, Jow PY.. (1977) Quantitative structure-activity relationships of antimalarial and dihydrofolate reductase inhibition by quinazolines and 5-substituted benzyl-2,4-diaminopyrimidines., 20 (1): [PMID:319234] [10.1021/jm00211a020] |
Source
Source(1):