4'-[3-(3-Dimethylamino-propyl)-4-methoxy-benzoylamino]-2-methyl-biphenyl-4-carboxylic acid

ID: ALA72092

PubChem CID: 10321355

Max Phase: Preclinical

Molecular Formula: C27H30N2O4

Molecular Weight: 446.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C(=O)Nc2ccc(-c3ccc(C(=O)O)cc3C)cc2)cc1CCCN(C)C

Standard InChI:  InChI=1S/C27H30N2O4/c1-18-16-22(27(31)32)9-13-24(18)19-7-11-23(12-8-19)28-26(30)21-10-14-25(33-4)20(17-21)6-5-15-29(2)3/h7-14,16-17H,5-6,15H2,1-4H3,(H,28,30)(H,31,32)

Standard InChI Key:  ARUYHNGXUSSPTH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.3792   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -4.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9292   -4.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6875   -3.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3417   -3.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4792   -2.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2042   -0.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -2.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4500   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4042   -4.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5917   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3792   -5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1875   -2.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6042   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6292    0.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3750   -0.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8167   -5.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 12  1  0
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  7 15  2  0
  8  3  2  0
  9  4  1  0
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 24 19  1  0
 25 19  2  0
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 31 23  1  0
 32 23  1  0
 33 26  1  0
 12 20  1  0
 13 11  1  0
  7  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA72092

   4-[4-[[3-[3-(Dimethylamino)propyl]-4-methoxybenzoyl]amino]phenyl]-3-methylbenzoic 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: 446.55

Molecular Weight (Monoisotopic): 446.2206

AlogP: 5.12

#Rotatable Bonds: 9

Polar Surface Area: 78.87

Molecular Species: ZWITTERION

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.08

CX Basic pKa: 9.53

CX LogP: 2.67

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.48

Np Likeness Score: -0.80

References

1. Clitherow JW, Scopes DI, Skingle M, Jordan CC, Feniuk W, Campbell IB, Carter MC, Collington EW, Connor HE, Higgins GA..  (1994)  Evolution of a novel series of [(N,N-dimethylamino)propyl]- and piperazinylbenzanilides as the first selective 5-HT1D antagonists.,  37  (15): [PMID:8057272] [10.1021/jm00041a001]

Source

Source(1):

• Scientific Literature