4-Benzyloxy-1-[(methyl-phenethyl-carbamoyl)-methyl]-3a,4-dihydro-1H-indole-3-carboxylic acid

ID: ALA3706723

PubChem CID: 10503348

Max Phase: Preclinical

Molecular Formula: C27H26N2O4

Molecular Weight: 442.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(CCc1ccccc1)C(=O)Cn1cc(C(=O)O)c2c(OCc3ccccc3)cccc21

Standard InChI:  InChI=1S/C27H26N2O4/c1-28(16-15-20-9-4-2-5-10-20)25(30)18-29-17-22(27(31)32)26-23(29)13-8-14-24(26)33-19-21-11-6-3-7-12-21/h2-14,17H,15-16,18-19H2,1H3,(H,31,32)

Standard InChI Key:  PWCPJKIYPSJPPM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.5271   -4.2661    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7734   -4.6016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6339   -3.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3789   -2.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6705   -4.6786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9929   -2.8325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7379   -2.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2551   -0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9580   -1.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2428   -4.2661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5284   -3.0286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1510   -1.8033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4481   -0.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1039   -1.0187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2428   -3.4411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  2  0
  4  1  1  0
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  7  8  1  0
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 25 22  2  0
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 30 27  1  0
 31 24  2  0
 32 30  2  0
 33 29  1  0
  5  2  1  0
 11 12  1  0
 31 32  1  0
 28 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3706723

   1-[2-[Methyl(2-phenylethyl)amino]-2-oxoethyl]-4-phenylmethoxyindole-3-carboxylic 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: 442.52

Molecular Weight (Monoisotopic): 442.1893

AlogP: 4.62

#Rotatable Bonds: 9

Polar Surface Area: 71.77

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.49

CX Basic pKa: ┄

CX LogP: 4.65

CX LogD: 1.27

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.41

Np Likeness Score: -0.87

References

1. Chan WK, Huang FC, Morrissette MM, Warus JD, Moriarty KJ, Galemmo RA, Dankulich WD, Poli G, Sutherland CA..  (1996)  Structure-activity relationships study of two series of leukotriene B4 antagonists: novel indolyl and naphthyl compounds substituted with a 2-[methyl(2-phenethyl)amino]-2-oxoethyl side chain.,  39  (19): [PMID:8809164] [10.1021/jm950699x]

Source

Source(1):

• Scientific Literature