ID: ALA373257

Max Phase: Preclinical

Molecular Formula: C26H23F4N5O

Molecular Weight: 497.50

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cn1c(-c2ccccc2C(F)(F)F)nnc1C12CCC(c3nc(-c4ccc(F)cc4)no3)(CC1)CC2

Standard InChI:  InChI=1S/C26H23F4N5O/c1-35-21(18-4-2-3-5-19(18)26(28,29)30)32-33-22(35)24-10-13-25(14-11-24,15-12-24)23-31-20(34-36-23)16-6-8-17(27)9-7-16/h2-9H,10-15H2,1H3

Standard InChI Key:  FRKIPPLTMSQJLF-UHFFFAOYSA-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: 497.50

Molecular Weight (Monoisotopic): 497.1839

AlogP: 6.23

#Rotatable Bonds: 4

Polar Surface Area: 69.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa: 2.24

CX LogP: 6.75

CX LogD: 6.75

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.31

Np Likeness Score: -1.07

References

1. Gu X, Dragovic J, Koo GC, Koprak SL, LeGrand C, Mundt SS, Shah K, Springer MS, Tan EY, Thieringer R, Hermanowski-Vosatka A, Zokian HJ, Balkovec JM, Waddell ST..  (2005)  Discovery of 4-heteroarylbicyclo[2.2.2]octyltriazoles as potent and selective inhibitors of 11beta-HSD1: novel therapeutic agents for the treatment of metabolic syndrome.,  15  (23): [PMID:16185866] [10.1016/j.bmcl.2005.08.052]

2. Lee JH, Kang NS, Yoo SE..  (2008)  Docking-based 3D-QSAR study for 11beta-HSD1 inhibitors.,  18  (7): [PMID:18314331] [10.1016/j.bmcl.2008.02.042]

3. Fotsch C, Wang M..  (2008)  Blockade of glucocorticoid excess at the tissue level: inhibitors of 11beta-hydroxysteroid dehydrogenase type 1 as a therapy for type 2 diabetes.,  51  (16): [PMID:18652443] [10.1021/jm800369f]

4. Fotsch C, Bartberger MD, Bercot EA, Chen M, Cupples R, Emery M, Fretland J, Guram A, Hale C, Han N, Hickman D, Hungate RW, Hayashi M, Komorowski R, Liu Q, Matsumoto G, St Jean DJ, Ursu S, Véniant M, Xu G, Ye Q, Yuan C, Zhang J, Zhang X, Tu H, Wang M..  (2008)  Further studies with the 2-amino-1,3-thiazol-4(5H)-one class of 11beta-hydroxysteroid dehydrogenase type 1 inhibitors: reducing pregnane X receptor activity and exploring activity in a monkey pharmacodynamic model.,  51  (24): [PMID:19053753] [10.1021/jm801073z]

5. Bauman DR, Whitehead A, Contino LC, Cui J, Garcia-Calvo M, Gu X, Kevin N, Ma X, Pai LY, Shah K, Shen X, Stribling S, Zokian HJ, Metzger J, Shevell DE, Waddell ST..  (2013)  Evaluation of selective inhibitors of 11β-HSD1 for the treatment of hypertension.,  23  (12): [PMID:23659858] [10.1016/j.bmcl.2013.03.011]

Source

Source(1):

• Scientific Literature