(3R,4R)-3-Ethyl-1-(4-methoxy-phenyl)-4-phenyl-3-(3-phenyl-propyl)-azetidin-2-one

ID: ALA49500

Chembl Id: CHEMBL49500

PubChem CID: 10386228

Max Phase: Preclinical

Molecular Formula: C27H29NO2

Molecular Weight: 399.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@]1(CCCc2ccccc2)C(=O)N(c2ccc(OC)cc2)[C@@H]1c1ccccc1

Standard InChI:  InChI=1S/C27H29NO2/c1-3-27(20-10-13-21-11-6-4-7-12-21)25(22-14-8-5-9-15-22)28(26(27)29)23-16-18-24(30-2)19-17-23/h4-9,11-12,14-19,25H,3,10,13,20H2,1-2H3/t25-,27-/m1/s1

Standard InChI Key:  VARYUPXKMPRXTG-XNMGPUDCSA-N

Alternative Forms

1. Parent:

   

   ALA49500

   (3R,4R)-3-ethyl-1-(4-methoxyphenyl)-4-phenyl-3-(3-phenylpropyl)azetidin-2-one

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: 399.53

Molecular Weight (Monoisotopic): 399.2198

AlogP: 6.20

#Rotatable Bonds: 8

Polar Surface Area: 29.54

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.65

CX LogD: 6.65

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.42

Np Likeness Score: -0.07

References

1. Burnett DA, Caplen MA, Davis HR, Burrier RE, Clader JW..  (1994)  2-Azetidinones as inhibitors of cholesterol absorption.,  37  (12): [PMID:8021912] [10.1021/jm00038a001]

2. Clader JW, Burnett DA, Caplen MA, Domalski MS, Dugar S, Vaccaro W, Sher R, Browne ME, Zhao H, Burrier RE, Salisbury B, Davis HR..  (1996)  2-Azetidinone cholesterol absorption inhibitors: structure-activity relationships on the heterocyclic nucleus.,  39  (19): [PMID:8809157] [10.1021/jm960405n]

3. Itzhak Y, Kalir A, Weissman BA, Cohen S..  (1981)  New analgesic drugs derived from phencyclidine.,  24  (5): [PMID:7241506] [10.1021/jm00137a004]

Source

Source(1):

• Scientific Literature