ID: ALA363352

Max Phase: Preclinical

Molecular Formula: C17H17ClN2O3S

Molecular Weight: 364.85

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC/C=C\COC1(c2ccc(Cl)cc2)SC=C(C)n2c1noc2=O

Standard InChI:  InChI=1S/C17H17ClN2O3S/c1-3-4-5-10-22-17(13-6-8-14(18)9-7-13)15-19-23-16(21)20(15)12(2)11-24-17/h4-9,11H,3,10H2,1-2H3/b5-4-

Standard InChI Key:  FHQCBTSYENFAFR-PLNGDYQASA-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: 364.85

Molecular Weight (Monoisotopic): 364.0648

AlogP: 4.24

#Rotatable Bonds: 5

Polar Surface Area: 57.26

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.94

CX LogD: 4.94

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.74

Np Likeness Score: -0.40

References

1. Budriesi R, Carosati E, Chiarini A, Cosimelli B, Cruciani G, Ioan P, Spinelli D, Spisani R..  (2005)  A new class of selective myocardial calcium channel modulators. 2. Role of the acetal chain in oxadiazol-3-one derivatives.,  48  (7): [PMID:15801835] [10.1021/jm0493414]

2. Viale M, Cordazzo C, Cosimelli B, de Totero D, Castagnola P, Aiello C, Severi E, Petrillo G, Cianfriglia M, Spinelli D..  (2009)  Inhibition of MDR1 activity in vitro by a novel class of diltiazem analogues: toward new candidates.,  52  (2): [PMID:19093883] [10.1021/jm801195k]

3. Rosano C, Viale M, Cosimelli B, Severi E, Gangemi R, Ciogli A, De Totero D, Spinelli D..  (2013)  ABCB1 Structural Models, Molecular Docking, and Synthesis of New Oxadiazolothiazin-3-one Inhibitors.,  4  (8): [PMID:24900735] [10.1021/ml300436x]

4. Cuviello F, Bisaccia F, Spinelli D, Armentano MF, Bufo SA, Cosimelli B, Ostuni A..  (2019)  The P-glycoprotein inhibitor diltiazem-like 8-(4-chlorophenyl)-5-methyl-8-[(2Z)-pent-2-en-1-yloxy]-8H-[1,2,4]oxadiazolo[3,4-c][1,4]thiazin-3-one inhibits esterase activity and H3 histone acetylation.,  164  [PMID:30583246] [10.1016/j.ejmech.2018.12.037]

Source

Source(1):

• Scientific Literature