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

ID: ALA292239

Chembl Id: CHEMBL292239

PubChem CID: 10045902

Max Phase: Preclinical

Molecular Formula: C23H22N2O4

Molecular Weight: 390.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Cc2c(-c3ccccc3)c(-c3ccc([N+](=O)[O-])cc3)c(CC(=O)O)n2C1

Standard InChI:  InChI=1S/C23H22N2O4/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(18(12-20(26)27)24(19)14-23)16-8-10-17(11-9-16)25(28)29/h3-11H,12-14H2,1-2H3,(H,26,27)

Standard InChI Key:  VYMSMZLVFCEANQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA292239

   2-(2,2-dimethyl-6-(4-nitrophenyl)-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: 390.44

Molecular Weight (Monoisotopic): 390.1580

AlogP: 4.94

#Rotatable Bonds: 5

Polar Surface Area: 85.37

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.32

CX Basic pKa: ┄

CX LogP: 5.06

CX LogD: 2.11

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -0.30

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