ID: ALA1934449
Chembl Id: CHEMBL1934449
Cas Number: 1350448-42-8
PubChem CID: 56649343
Max Phase: Preclinical
Molecular Formula: C28H38O7
Molecular Weight: 486.61
Molecule Type: Small molecule
Associated Items:
Synonyms: 19-Hydroxywithaferin A | Withalongolide A|19-hydroxywithaferin A|CHEBI:69106|CHEMBL1934449|DTXSID701316661|Q27137447|(4beta,5beta,6beta,22R)-4,19,27-trihydroxy-5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione|1350448-42-8
Canonical SMILES: CC1=C(CO)C(=O)O[C@@H]([C@@H](C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5O[C@]56[C@@H](O)C=CC(=O)[C@]6(CO)[C@H]4CC[C@]23C)C1
Standard InChI: InChI=1S/C28H38O7/c1-14-10-21(34-25(33)17(14)12-29)15(2)18-4-5-19-16-11-24-28(35-24)23(32)7-6-22(31)27(28,13-30)20(16)8-9-26(18,19)3/h6-7,15-16,18-21,23-24,29-30,32H,4-5,8-13H2,1-3H3/t15-,16-,18+,19-,20-,21+,23-,24+,26+,27-,28+/m0/s1
Standard InChI Key: FJMXKFSOKLFYRC-CKNDUULBSA-N
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| Natural Product: Yes | 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: 486.61 | Molecular Weight (Monoisotopic): 486.2618 | AlogP: 2.33 | #Rotatable Bonds: 4 |
| Polar Surface Area: 116.59 | Molecular Species: NEUTRAL | HBA: 7 | HBD: 3 |
| #RO5 Violations: ┄ | HBA (Lipinski): 7 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): ┄ |
| CX Acidic pKa: 13.42 | CX Basic pKa: ┄ | CX LogP: 2.30 | CX LogD: 2.30 |
| Aromatic Rings: ┄ | Heavy Atoms: 35 | QED Weighted: 0.41 | Np Likeness Score: 3.80 |
| 1. Zhang H, Samadi AK, Gallagher RJ, Araya JJ, Tong X, Day VW, Cohen MS, Kindscher K, Gollapudi R, Timmermann BN.. (2011) Cytotoxic withanolide constituents of Physalis longifolia., 74 (12): [PMID:22098611] [10.1021/np200635r] |
| 2. Motiwala HF, Bazzill J, Samadi A, Zhang H, Timmermann BN, Cohen MS, Aubé J.. (2013) Synthesis and Cytotoxicity of Semisynthetic Withalongolide A Analogues., 4 (11): [PMID:24273633] [10.1021/ml400267q] |
| 3. Patouret R, Barluenga S, Winssinger N.. (2022) Withaferin A, a polyfunctional pharmacophore that includes covalent engagement of IPO5, is an inhibitor of influenza A replication., 69 [PMID:35772286] [10.1016/j.bmc.2022.116883] |
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