[2-(4-Chloro-phenyl)-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl]-acetic acid

ID: ALA294159

Chembl Id: CHEMBL294159

PubChem CID: 10066564

Max Phase: Preclinical

Molecular Formula: C21H18ClNO2

Molecular Weight: 351.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1c(-c2ccc(Cl)cc2)c(-c2ccccc2)c2n1CCC2

Standard InChI:  InChI=1S/C21H18ClNO2/c22-16-10-8-15(9-11-16)21-18(13-19(24)25)23-12-4-7-17(23)20(21)14-5-2-1-3-6-14/h1-3,5-6,8-11H,4,7,12-13H2,(H,24,25)

Standard InChI Key:  YHELUJCERLGVBD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA294159

   2-(6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl)acetic acid

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: 351.83

Molecular Weight (Monoisotopic): 351.1026

AlogP: 5.05

#Rotatable Bonds: 4

Polar Surface Area: 42.23

Molecular Species: ACID

HBA: 2

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.72

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 2.36

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.71

Np Likeness Score: -0.53

References

1. Laufer SA, Augustin J, Dannhardt G, Kiefer W..  (1994)  (6,7-Diaryldihydropyrrolizin-5-yl)acetic acids, a novel class of potent dual inhibitors of both cyclooxygenase and 5-lipoxygenase.,  37  (12): [PMID:8021931] [10.1021/jm00038a021]

2. Liedtke AJ, Keck PR, Lehmann F, Koeberle A, Werz O, Laufer SA..  (2009)  Arylpyrrolizines as inhibitors of microsomal prostaglandin E2 synthase-1 (mPGES-1) or as dual inhibitors of mPGES-1 and 5-lipoxygenase (5-LOX).,  52  (15): [PMID:19719242] [10.1021/jm900481c]

3. Aparoy P, Kumar Reddy K, Kalangi SK, Chandramohan Reddy T, Reddanna P..  (2010)  Pharmacophore modeling and virtual screening for designing potential 5-lipoxygenase inhibitors.,  20  (3): [PMID:20045317] [10.1016/j.bmcl.2009.12.047]

Source

Source(1):

• Scientific Literature