ID: ALA521969

Max Phase: Preclinical

Molecular Formula: C23H21ClO6

Molecular Weight: 428.87

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1cc(OC)c2c(c1Cl)O[C@]1(C2=O)C(OCc2ccccc2)=CC(=O)C[C@H]1C

Standard InChI:  InChI=1S/C23H21ClO6/c1-13-9-15(25)10-18(29-12-14-7-5-4-6-8-14)23(13)22(26)19-16(27-2)11-17(28-3)20(24)21(19)30-23/h4-8,10-11,13H,9,12H2,1-3H3/t13-,23+/m1/s1

Standard InChI Key:  LAWAOYZSUFCPKY-ZLOXQWCVSA-N

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

Properties

Molecular Weight: 428.87

Molecular Weight (Monoisotopic): 428.1027

AlogP: 4.38

#Rotatable Bonds: 5

Polar Surface Area: 71.06

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.90

CX LogD: 3.90

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.70

Np Likeness Score: 1.25

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]

4. Petersen AB, Konotop G, Hanafiah NHM, Hammershøj P, Raab MS, Krämer A, Clausen MH..  (2016)  Strategies for improving the solubility and metabolic stability of griseofulvin analogues.,  116  [PMID:27061984] [10.1016/j.ejmech.2016.03.071]

5. Petersen AB, Andersen NS, Konotop G, Hanafiah NH, Raab MS, Krämer A, Clausen MH..  (2017)  Synthesis and formulation studies of griseofulvin analogues with improved solubility and metabolic stability.,  130  [PMID:28258034] [10.1016/j.ejmech.2017.02.055]

Source

Source(1):

• Scientific Literature