4-[3-(4-Decyloxy-phenoxy)-2-oxo-propoxy]-3-nitro-benzoic acid

ID: ALA286067

Chembl Id: CHEMBL286067

PubChem CID: 11134688

Max Phase: Preclinical

Molecular Formula: C26H33NO8

Molecular Weight: 487.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCOc1ccc(OCC(=O)COc2ccc(C(=O)O)cc2[N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C26H33NO8/c1-2-3-4-5-6-7-8-9-16-33-22-11-13-23(14-12-22)34-18-21(28)19-35-25-15-10-20(26(29)30)17-24(25)27(31)32/h10-15,17H,2-9,16,18-19H2,1H3,(H,29,30)

Standard InChI Key:  DJGMDXHOTRZDSB-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA286067

   4-[3-(4-Decyloxy-phenoxy)-2-oxo-propoxy]-3-nitro-benzoic 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: 487.55

Molecular Weight (Monoisotopic): 487.2206

AlogP: 5.84

#Rotatable Bonds: 18

Polar Surface Area: 125.20

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.80

CX Basic pKa:

CX LogP: 6.57

CX LogD: 3.31

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.16

Np Likeness Score: -0.59

References

1. Connolly S, Bennion C, Botterell S, Croshaw PJ, Hallam C, Hardy K, Hartopp P, Jackson CG, King SJ, Lawrence L, Mete A, Murray D, Robinson DH, Smith GM, Stein L, Walters I, Wells E, Withnall WJ..  (2002)  Design and synthesis of a novel and potent series of inhibitors of cytosolic phospholipase A(2) based on a 1,3-disubstituted propan-2-one skeleton.,  45  (6): [PMID:11882004] [10.1021/jm011050x]

2. Noha SM, Jazzar B, Kuehnl S, Rollinger JM, Stuppner H, Schaible AM, Werz O, Wolber G, Schuster D..  (2012)  Pharmacophore-based discovery of a novel cytosolic phospholipase A(2)α inhibitor.,  22  (2): [PMID:22192589] [10.1016/j.bmcl.2011.11.093]

Source

Source(1):

• Scientific Literature