4-(3-(1-benzhydryl-5-chloro-2-(2-((3,4-dichlorophenyl)methylsulfonamido)ethyl)-1H-indol-3-yl)propyl)benzoic acid

ID: ALA272342

Chembl Id: CHEMBL272342

Cas Number: 381683-94-9

PubChem CID: 9853499

Max Phase: Phase

Molecular Formula: C40H35Cl3N2O4S

Molecular Weight: 746.16

Molecule Type: Small molecule

Names and Identifiers

Synonyms: PLA-902 | Efipladib|381683-94-9|Efipladib [USAN:INN]|PLA-902|UNII-S97YUG2A91|S97YUG2A91|CHEMBL272342|Efipladib (USAN)|EFIPLADIB [USAN]|Efipladib [INN]|4-(3-(1-benzhydryl-5-chloro-2-(2-(((3,4-dichlorophenyl)methyl)sulfonamido)ethyl)-1H-indol-3-yl)propyl)benzoic|4-(3-(5-Chloro-2-(2-((((3,4-dichlorophenyl)methyl)sulfonyl)amino)ethyl)-1-(diphenylmethyl)-1H-indol-3-yl)propyl)benzoic acid|4-(3-(5-Chloro-2-(2-(((3,4-dichlorobenzyl)sulfonyl)amino)ethyl)-1-(diphenylmethyl)-1H-indol-3-yl)propyl)benzoic acShow More⌵

Canonical SMILES:  O=C(O)c1ccc(CCCc2c(CCNS(=O)(=O)Cc3ccc(Cl)c(Cl)c3)n(C(c3ccccc3)c3ccccc3)c3ccc(Cl)cc23)cc1

Standard InChI:  InChI=1S/C40H35Cl3N2O4S/c41-32-19-21-37-34(25-32)33(13-7-8-27-14-17-31(18-15-27)40(46)47)38(22-23-44-50(48,49)26-28-16-20-35(42)36(43)24-28)45(37)39(29-9-3-1-4-10-29)30-11-5-2-6-12-30/h1-6,9-12,14-21,24-25,39,44H,7-8,13,22-23,26H2,(H,46,47)

Standard InChI Key:  HIZOPJQOPKRKFM-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA272342

   EFIPLADIB

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: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 746.16

Molecular Weight (Monoisotopic): 744.1383

AlogP: 9.77

#Rotatable Bonds: 14

Polar Surface Area: 88.40

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.24

CX Basic pKa:

CX LogP: 10.55

CX LogD: 7.55

Aromatic Rings: 6

Heavy Atoms: 50

QED Weighted: 0.12

Np Likeness Score: -0.90

References

1. Lee KL, Behnke ML, Foley MA, Chen L, Wang W, Vargas R, Nunez J, Tam S, Mollova N, Xu X, Shen MW, Ramarao MK, Goodwin DG, Nickerson-Nutter CL, Abraham WM, Williams C, Clark JD, McKew JC..  (2008)  Benzenesulfonamide indole inhibitors of cytosolic phospholipase A2alpha: optimization of in vitro potency and rat pharmacokinetics for oral efficacy.,  16  (3): [PMID:17998165] [10.1016/j.bmc.2007.10.060]

2. Chen L, Wang W, Lee KL, Shen MW, Murphy EA, Zhang W, Xu X, Tam S, Nickerson-Nutter C, Goodwin DG, Clark JD, McKew JC..  (2009)  Reactions of functionalized sulfonamides: application to lowering the lipophilicity of cytosolic phospholipase A2alpha inhibitors.,  52  (4): [PMID:19178292] [10.1021/jm8009876]

3. McKew JC, Lee KL, Shen MW, Thakker P, Foley MA, Behnke ML, Hu B, Sum FW, Tam S, Hu Y, Chen L, Kirincich SJ, Michalak R, Thomason J, Ipek M, Wu K, Wooder L, Ramarao MK, Murphy EA, Goodwin DG, Albert L, Xu X, Donahue F, Ku MS, Keith J, Nickerson-Nutter CL, Abraham WM, Williams C, Hegen M, Clark JD..  (2008)  Indole cytosolic phospholipase A2 alpha inhibitors: discovery and in vitro and in vivo characterization of 4-{3-[5-chloro-2-(2-{[(3,4-dichlorobenzyl)sulfonyl]amino}ethyl)-1-(diphenylmethyl)-1H-indol-3-yl]propyl}benzoic acid, efipladib.,  51  (12): [PMID:18498150] [10.1021/jm701467e]

4. Kirincich SJ, Xiang J, Green N, Tam S, Yang HY, Shim J, Shen MW, Clark JD, McKew JC..  (2009)  Benzhydrylquinazolinediones: novel cytosolic phospholipase A2alpha inhibitors with improved physicochemical properties.,  17  (13): [PMID:19482480] [10.1016/j.bmc.2009.05.027]

5. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

6. Tomoo T, Nakatsuka T, Katayama T, Hayashi Y, Fujieda Y, Terakawa M, Nagahira K..  (2014)  Design, synthesis, and biological evaluation of 3-(1-Aryl-1H-indol-5-yl)propanoic acids as new indole-based cytosolic phospholipase A2α inhibitors.,  57  (17): [PMID:25102418] [10.1021/jm500494y]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names