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ID: ALA2414617
Max Phase: Preclinical
Molecular Formula: C22H21ClFNO5S
Molecular Weight: 465.93
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: OC[C@H]1O[C@@H](c2ccc(Cl)c(Cc3ccc(-c4ccc(F)nc4)s3)c2)[C@H](O)[C@@H](O)[C@@H]1O
Standard InChI: InChI=1S/C22H21ClFNO5S/c23-15-4-1-11(22-21(29)20(28)19(27)16(10-26)30-22)7-13(15)8-14-3-5-17(31-14)12-2-6-18(24)25-9-12/h1-7,9,16,19-22,26-29H,8,10H2/t16-,19-,20+,21-,22+/m1/s1
Standard InChI Key: WQWNUPFPUXHKAQ-OSKXVONFSA-N
Associated Targets(Human)
Sodium/glucose cotransporter 1 1526 Activities
Sodium/glucose cotransporter 2 2000 Activities
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Associated Targets(non-human)
Mus musculus 284745 Activities
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Rattus norvegicus 775804 Activities
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Solute carrier family 2, facilitated glucose transporter member 1 20 Activities
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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 |
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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: 465.93 | Molecular Weight (Monoisotopic): 465.0813 | AlogP: 2.71 | #Rotatable Bonds: 5 |
| Polar Surface Area: 103.04 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 4 |
| #RO5 Violations: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 12.57 | CX Basic pKa: | CX LogP: 2.79 | CX LogD: 2.79 |
| Aromatic Rings: 3 | Heavy Atoms: 31 | QED Weighted: 0.43 | Np Likeness Score: 0.13 |
References
| 1. Koga Y, Sakamaki S, Hongu M, Kawanishi E, Sakamoto T, Yamamoto Y, Kimata H, Nakayama K, Kuriyama C, Matsushita Y, Ueta K, Tsuda-Tsukimoto M, Nomura S.. (2013) C-Glucosides with heteroaryl thiophene as novel sodium-dependent glucose cotransporter 2 inhibitors., 21 (17): [PMID:23809172] [10.1016/j.bmc.2013.05.048] |
| 2. Maccari R, Ottanà R.. (2022) Sodium-Glucose Cotransporter Inhibitors as Antidiabetic Drugs: Current Development and Future Perspectives., 65 (16.0): [PMID:35924548] [10.1021/acs.jmedchem.2c00867] |
Source
Source(1):