ID: ALA275835

Max Phase: Phase

Molecular Formula: C18H24N2O2S

Molecular Weight: 332.47

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(C)(C)c1cc(/C=C2\SC(=N)NC2=O)cc(C(C)(C)C)c1O

Standard InChI:  InChI=1S/C18H24N2O2S/c1-17(2,3)11-7-10(8-12(14(11)21)18(4,5)6)9-13-15(22)20-16(19)23-13/h7-9,21H,1-6H3,(H2,19,20,22)/b13-9-

Standard InChI Key:  AKTXOQVMWSFEBQ-LCYFTJDESA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 332.47

Molecular Weight (Monoisotopic): 332.1558

AlogP: 4.13

#Rotatable Bonds: 1

Polar Surface Area: 73.18

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 10.38

CX Basic pKa: 1.53

CX LogP: 4.65

CX LogD: 4.65

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.68

Np Likeness Score: -0.63

References

1. Song Y, Connor DT, Doubleday R, Sorenson RJ, Sercel AD, Unangst PC, Roth BD, Gilbertsen RB, Chan K, Schrier DJ, Guglietta A, Bornemeier DA, Dyer RD..  (1999)  Synthesis, structure-activity relationships, and in vivo evaluations of substituted di-tert-butylphenols as a novel class of potent, selective, and orally active cyclooxygenase-2 inhibitors. 1. Thiazolone and oxazolone series.,  42  (7): [PMID:10197959] [10.1021/jm9805081]

2. Unangst PC, Connor DT, Cetenko WA, Sorenson RJ, Sircar JC, Wright CD, Schrier DJ, Dyer RD.  (1993)  Oxazole, thiazole, and imidazole derivatives of 2,6-di-tert-butylphenol as dual 5-lipoxygenase and cyclooxygenase inhibitors,  3  (8): [10.1016/S0960-894X(00)80051-7]

3. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

4. Misra S, Ghatak S, Patil N, Dandawate P, Ambike V, Adsule S, Unni D, Venkateswara Swamy K, Padhye S..  (2013)  Novel dual cyclooxygenase and lipoxygenase inhibitors targeting hyaluronan-CD44v6 pathway and inducing cytotoxicity in colon cancer cells.,  21  (9): [PMID:23517721] [10.1016/j.bmc.2013.02.033]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names