ID: ALA1221983

Max Phase: Preclinical

Molecular Formula: C28H28ClN3OS

Molecular Weight: 490.07

Molecule Type: Small molecule

Representations

Canonical SMILES:  CN[C@H]1CC[C@H](N(Cc2cccc(-c3ccncc3)c2)C(=O)c2sc3ccccc3c2Cl)CC1

Standard InChI:  InChI=1S/C28H28ClN3OS/c1-30-22-9-11-23(12-10-22)32(28(33)27-26(29)24-7-2-3-8-25(24)34-27)18-19-5-4-6-21(17-19)20-13-15-31-16-14-20/h2-8,13-17,22-23,30H,9-12,18H2,1H3/t22-,23-

Standard InChI Key:  VFSUUTYAEQOIMW-YHBQERECSA-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: 490.07

Molecular Weight (Monoisotopic): 489.1642

AlogP: 6.79

#Rotatable Bonds: 6

Polar Surface Area: 45.23

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 10.40

CX LogP: 5.78

CX LogD: 2.97

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.32

Np Likeness Score: -1.60

References

1. Sinha S, Chen JK..  (2006)  Purmorphamine activates the Hedgehog pathway by targeting Smoothened.,  2  (1): [PMID:16408088] [10.1038/nchembio753]

2. Heretsch P, Tzagkaroulaki L, Giannis A..  (2010)  Modulators of the hedgehog signaling pathway.,  18  (18): [PMID:20708941] [10.1016/j.bmc.2010.07.038]

3. Seifert K, Büttner A, Rigol S, Eilert N, Wandel E, Giannis A..  (2012)  Potent small molecule Hedgehog agonists induce VEGF expression in vitro.,  20  (21): [PMID:22985958] [10.1016/j.bmc.2012.08.026]

4. Manetti F, Petricci E, Gabrielli A, Mann A, Faure H, Gorojankina T, Brasseur L, Hoch L, Ruat M, Taddei M..  (2016)  Design, synthesis and biological characterization of a new class of osteogenic (1H)-quinolone derivatives.,  121  [PMID:27429255] [10.1016/j.ejmech.2016.05.062]

5. Zhao F, Wu Y, Zhou F, Xue D, Zhao S, Lu W, Liu X, Hu T, Qiu Y, Li R, Gu T, Xu Y, Xu F, Zhong G, Jiang Z, Zhao S, Tao H..  (2021)  Elucidation of Distinct Modular Assemblies of Smoothened Receptor by Bitopic Ligand Measurement.,  64  (18.0): [PMID:34492176] [10.1021/acs.jmedchem.1c01220]

Source

Source(1):

• Scientific Literature