(S)-4-(1-(1-(3-chlorobenzyl)-3-methyl-1H-indole-7-carboxamido)ethyl)benzoic acid

ID: ALA1083746

PubChem CID: 24765766

Max Phase: Preclinical

Molecular Formula: C26H23ClN2O3

Molecular Weight: 446.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn(Cc2cccc(Cl)c2)c2c(C(=O)N[C@@H](C)c3ccc(C(=O)O)cc3)cccc12

Standard InChI:  InChI=1S/C26H23ClN2O3/c1-16-14-29(15-18-5-3-6-21(27)13-18)24-22(16)7-4-8-23(24)25(30)28-17(2)19-9-11-20(12-10-19)26(31)32/h3-14,17H,15H2,1-2H3,(H,28,30)(H,31,32)/t17-/m0/s1

Standard InChI Key:  XTRLBRLYAATAGR-KRWDZBQOSA-N

Molfile:  

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    0.9484   -7.4074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1134   -8.0828    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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 13 15  1  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083746

   (S)-4-(1-(1-(3-chlorobenzyl)-3-methyl-1H-indole-7-carboxamido)ethyl)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: 446.93

Molecular Weight (Monoisotopic): 446.1397

AlogP: 5.84

#Rotatable Bonds: 6

Polar Surface Area: 71.33

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.06

CX Basic pKa: ┄

CX LogP: 6.01

CX LogD: 2.89

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.22

References

1. Colucci J, Boyd M, Berthelette C, Chiasson JF, Wang Z, Ducharme Y, Friesen R, Wrona M, Levesque JF, Denis D, Mathieu MC, Stocco R, Therien AG, Clarke P, Rowland S, Xu D, Han Y..  (2010)  Discovery of 4-[1-[([1-[4-(trifluoromethyl)benzyl]-1H-indol-7-yl]carbonyl)amino]cyclopropyl]benzoic acid (MF-766), a highly potent and selective EP4 antagonist for treating inflammatory pain.,  20  (12): [PMID:20471829] [10.1016/j.bmcl.2010.04.065]

Source

Source(1):

• Scientific Literature