(2R,6R)-1-(3-Hydroxy-azetidin-1-yl)-2-(6-hydroxy-2-phenyl-adamantan-2-yl)-ethanone

ID: ALA4080667

Chembl Id: CHEMBL4080667

Max Phase: Preclinical

Molecular Formula: C21H27NO3

Molecular Weight: 341.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CC1(c2ccccc2)C2CC3CC1CC(C2)C3O)N1CC(O)C1

Standard InChI:  InChI=1S/C21H27NO3/c23-18-11-22(12-18)19(24)10-21(15-4-2-1-3-5-15)16-6-13-7-17(21)9-14(8-16)20(13)25/h1-5,13-14,16-18,20,23,25H,6-12H2/t13?,14?,16?,17?,20-,21?

Standard InChI Key:  OAAZMUGLOXGVNH-QKVOFEMESA-N

Alternative Forms

1. Parent:

   

   ALA4080667

   ---

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: 341.45

Molecular Weight (Monoisotopic): 341.1991

AlogP: 1.94

#Rotatable Bonds: 3

Polar Surface Area: 60.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: 1.34

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.88

Np Likeness Score: 0.40

References

1. Ye XY, Chen SY, Wu S, Yoon DS, Wang H, Hong Z, O'Connor SP, Li J, Li JJ, Kennedy LJ, Walker SJ, Nayeem A, Sheriff S, Camac DM, Ramamurthy V, Morin PE, Zebo R, Taylor JR, Morgan NN, Ponticiello RP, Harrity T, Apedo A, Golla R, Seethala R, Wang M, Harper TW, Sleczka BG, He B, Kirby M, Leahy DK, Li J, Hanson RL, Guo Z, Li YX, DiMarco JD, Scaringe R, Maxwell B, Moulin F, Barrish JC, Gordon DA, Robl JA..  (2017)  Discovery of Clinical Candidate 2-((2S,6S)-2-Phenyl-6-hydroxyadamantan-2-yl)-1-(3'-hydroxyazetidin-1-yl)ethanone [BMS-816336], an Orally Active Novel Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitor.,  60  (12): [PMID:28537398] [10.1021/acs.jmedchem.7b00211]

2. Ye XY, Chen SY, Wu S, Yoon DS, Wang H, Hong Z, O'Connor SP, Li J, Li JJ, Kennedy LJ, Walker SJ, Nayeem A, Sheriff S, Camac DM, Ramamurthy V, Morin PE, Zebo R, Taylor JR, Morgan NN, Ponticiello RP, Harrity T, Apedo A, Golla R, Seethala R, Wang M, Harper TW, Sleczka BG, He B, Kirby M, Leahy DK, Li J, Hanson RL, Guo Z, Li YX, DiMarco JD, Scaringe R, Maxwell B, Moulin F, Barrish JC, Gordon DA, Robl JA..  (2017)  Discovery of Clinical Candidate 2-((2S,6S)-2-Phenyl-6-hydroxyadamantan-2-yl)-1-(3'-hydroxyazetidin-1-yl)ethanone [BMS-816336], an Orally Active Novel Selective 11β-Hydroxysteroid Dehydrogenase Type 1 Inhibitor.,  60  (12): [PMID:28537398] [10.1021/acs.jmedchem.7b00211]

Source

Source(1):

• Scientific Literature