N-{4-[6-(4-trifluoromethylcyclohex-1-enyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide

ID: ALA229431

Chembl Id: CHEMBL229431

PubChem CID: 16748464

Max Phase: Preclinical

Molecular Formula: C20H17F3N4O2S

Molecular Weight: 434.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)Nc1nc2c(Oc3cc(C4=CCC(C(F)(F)F)CC4)ncn3)cccc2s1

Standard InChI:  InChI=1S/C20H17F3N4O2S/c1-11(28)26-19-27-18-15(3-2-4-16(18)30-19)29-17-9-14(24-10-25-17)12-5-7-13(8-6-12)20(21,22)23/h2-5,9-10,13H,6-8H2,1H3,(H,26,27,28)

Standard InChI Key:  BPHBCIKYYUQAFI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA229431

   N-{4-[6-(4-Trifluoromethyl-cyclohex-1-enyl)-pyrimidin-4-yloxy]-benzothiazol-2-yl}-acetamide

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: 434.44

Molecular Weight (Monoisotopic): 434.1024

AlogP: 5.58

#Rotatable Bonds: 4

Polar Surface Area: 77.00

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.03

CX Basic pKa: 2.09

CX LogP: 5.00

CX LogD: 4.92

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.58

Np Likeness Score: -1.34

References

1. Wang HL, Katon J, Balan C, Bannon AW, Bernard C, Doherty EM, Dominguez C, Gavva NR, Gore V, Ma V, Nishimura N, Surapaneni S, Tang P, Tamir R, Thiel O, Treanor JJ, Norman MH..  (2007)  Novel vanilloid receptor-1 antagonists: 3. The identification of a second-generation clinical candidate with improved physicochemical and pharmacokinetic properties.,  50  (15): [PMID:17585751] [10.1021/jm070191h]

2. Das B, Baidya ATK, Mathew AT, Yadav AK, Kumar R..  (2022)  Structural modification aimed for improving solubility of lead compounds in early phase drug discovery.,  56  [PMID:35033884] [10.1016/j.bmc.2022.116614]

3. Subbaiah MAM, Meanwell NA..  (2021)  Bioisosteres of the Phenyl Ring: Recent Strategic Applications in Lead Optimization and Drug Design.,  64  (19.0): [PMID:34591488] [10.1021/acs.jmedchem.1c01215]

Source

Source(1):

• Scientific Literature