6-(4-chlorophenyl)-3-(4-((3,3-difluoro-1-hydroxycyclobutyl)methoxy)-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one

ID: ALA2147472

Chembl Id: CHEMBL2147472

Cas Number: 1197420-11-3

PubChem CID: 57988809

Max Phase: Preclinical

Molecular Formula: C24H19ClF2N2O4S

Molecular Weight: 504.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(-n2cnc3cc(-c4ccc(Cl)cc4)sc3c2=O)ccc1OCC1(O)CC(F)(F)C1

Standard InChI:  InChI=1S/C24H19ClF2N2O4S/c1-32-19-8-16(6-7-18(19)33-12-23(31)10-24(26,27)11-23)29-13-28-17-9-20(34-21(17)22(29)30)14-2-4-15(25)5-3-14/h2-9,13,31H,10-12H2,1H3

Standard InChI Key:  NCXJWNAKIMMZOC-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2147472

   6-(4-chlorophenyl)-3-(4-((3,3-difluoro-1-hydroxycyclobutyl)methoxy)-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one

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

Calculated Properties

Molecular Weight: 504.94

Molecular Weight (Monoisotopic): 504.0722

AlogP: 5.32

#Rotatable Bonds: 6

Polar Surface Area: 73.58

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.76

CX Basic pKa: ┄

CX LogP: 4.82

CX LogD: 4.82

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.38

Np Likeness Score: -0.95

References

1. Högberg T, Frimurer TM, Sasmal PK..  (2012)  Melanin concentrating hormone receptor 1 (MCHR1) antagonists-Still a viable approach for obesity treatment?,  22  (19): [PMID:22954736] [10.1016/j.bmcl.2012.08.025]

2. Ahmad S, Washburn WN, Hernandez AS, Bisaha S, Ngu K, Wang W, Pelleymounter MA, Longhi D, Flynn N, Azzara AV, Rohrbach K, Devenny J, Rooney S, Thomas M, Glick S, Godonis H, Harvey S, Zhang H, Gemzik B, Janovitz EB, Huang C, Zhang L, Robl JA, Murphy BJ..  (2016)  Synthesis and Antiobesity Properties of 6-(4-Chlorophenyl)-3-(4-((3,3-difluoro-1-hydroxycyclobutyl)methoxy)-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one (BMS-814580): A Highly Efficacious Melanin Concentrating Hormone Receptor 1 (MCHR1) Inhibitor.,  59  (19): [PMID:27564419] [10.1021/acs.jmedchem.6b00676]

Source

Source(1):

• Scientific Literature