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ID: ALA491938
Max Phase: Preclinical
Molecular Formula: C23H21ClO5S
Molecular Weight: 444.94
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc(OC)c2c(c1Cl)O[C@]1(C2=O)C(SCc2ccccc2)=CC(=O)C[C@H]1C
Standard InChI: InChI=1S/C23H21ClO5S/c1-13-9-15(25)10-18(30-12-14-7-5-4-6-8-14)23(13)22(26)19-16(27-2)11-17(28-3)20(24)21(19)29-23/h4-8,10-11,13H,9,12H2,1-3H3/t13-,23+/m1/s1
Standard InChI Key: KOWBFBWFLFWGIE-ZLOXQWCVSA-N
Associated Targets(Human)
MDA-MB-231 73002 Activities
HCC1937 423 Activities
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Associated Targets(non-human)
Trichophyton mentagrophytes 4846 Activities
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Trichophyton rubrum 3646 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: 444.94 | Molecular Weight (Monoisotopic): 444.0798 | AlogP: 5.10 | #Rotatable Bonds: 5 |
| Polar Surface Area: 61.83 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 0 |
| #RO5 Violations: 1 | HBA (Lipinski): 5 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 4.58 | CX LogD: 4.58 |
| Aromatic Rings: 2 | Heavy Atoms: 30 | QED Weighted: 0.64 | Np Likeness Score: 0.86 |
References
| 1. Rønnest MH, Rebacz B, Markworth L, Terp AH, Larsen TO, Krämer A, Clausen MH.. (2009) Synthesis and structure-activity relationship of griseofulvin analogues as inhibitors of centrosomal clustering in cancer cells., 52 (10): [PMID:19402668] [10.1021/jm801517j] |
| 2. Rønnest MH, Raab MS, Anderhub S, Boesen S, Krämer A, Larsen TO, Clausen MH.. (2012) Disparate SAR data of griseofulvin analogues for the dermatophytes Trichophyton mentagrophytes, T. rubrum, and MDA-MB-231 cancer cells., 55 (2): [PMID:22191585] [10.1021/jm200835c] |
| 3. Liéby-Muller F, Heudré Le Baliner Q, Grisoni S, Fournier E, Guilbaud N, Marion F.. (2015) Synthesis and activities towards resistant cancer cells of sulfone and sulfoxide griseofulvin derivatives., 25 (10): [PMID:25872984] [10.1016/j.bmcl.2015.03.081] |
Source
Source(1):