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

ID: ALA1085081

PubChem CID: 24765672

Max Phase: Preclinical

Molecular Formula: C25H21ClN2O3

Molecular Weight: 432.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)c1cccc2ccn(Cc3cccc(Cl)c3)c12)c1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C25H21ClN2O3/c1-16(18-8-10-20(11-9-18)25(30)31)27-24(29)22-7-3-5-19-12-13-28(23(19)22)15-17-4-2-6-21(26)14-17/h2-14,16H,15H2,1H3,(H,27,29)(H,30,31)/t16-/m0/s1

Standard InChI Key:  TWQIOOHEKFFYJQ-INIZCTEOSA-N

Molfile:  

     RDKit          2D

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   -5.6443    1.6102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2159    2.4412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9312    2.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2130    1.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9305    1.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7604    0.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9376    0.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6000    1.0555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7753    1.0777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5029    2.8564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7869    2.4466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5061    3.6814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0740    2.8617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3580    2.4519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0653    2.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0771    3.6867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7900    1.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7942    0.4009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5024    1.6421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7415   -0.3490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3106   -1.0516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4850   -1.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0922   -0.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5253    0.4001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2675   -0.2744    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 13 15  1  0
  3  4  2  0
 15 16  1  0
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  9  5  1  0
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  4  1  1  0
 20 21  2  0
 21 16  1  0
  9 10  1  0
 15 22  1  1
  5  6  2  0
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  3 12  1  0
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  5  3  1  0
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 12 14  2  0
 29 30  2  0
 30 11  1  0
  1  2  2  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1085081

   (S)-4-(1-(1-(3-chlorobenzyl)-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: 432.91

Molecular Weight (Monoisotopic): 432.1241

AlogP: 5.53

#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: 5.50

CX LogD: 2.38

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: -1.23

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]

2. Boyd MJ, Berthelette C, Chiasson JF, Clark P, Colucci J, Denis D, Han Y, Lévesque JF, Mathieu MC, Stocco R, Therien A, Rowland S, Wrona M, Xu D..  (2011)  A novel series of potent and selective EP(4) receptor ligands: facile modulation of agonism and antagonism.,  21  (1): [PMID:21126875] [10.1016/j.bmcl.2010.10.106]

Source

Source(1):

• Scientific Literature