1-((R)-3-{5-[3-(4-Chloro-phenyl)-propoxy]-1-methyl-1H-indol-3-yl}-1-hydroxymethyl-propyl)-1H-imidazole-4-carboxylic acid amide

ID: ALA340297

PubChem CID: 10480325

Max Phase: Preclinical

Molecular Formula: C26H29ClN4O3

Molecular Weight: 481.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1cc(CC[C@H](CO)n2cnc(C(N)=O)c2)c2cc(OCCCc3ccc(Cl)cc3)ccc21

Standard InChI:  InChI=1S/C26H29ClN4O3/c1-30-14-19(6-9-21(16-32)31-15-24(26(28)33)29-17-31)23-13-22(10-11-25(23)30)34-12-2-3-18-4-7-20(27)8-5-18/h4-5,7-8,10-11,13-15,17,21,32H,2-3,6,9,12,16H2,1H3,(H2,28,33)/t21-/m1/s1

Standard InChI Key:  LOLFJCSELDRAPA-OAQYLSRUSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  1  0  0  0  0  0999 V2000
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    2.5292   -0.7417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542    3.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500    2.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042    0.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042    0.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1625   -0.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0000    1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250    0.9583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500    3.2958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5583   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -1.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -1.4917    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.7125    0.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7250   -0.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9583   -0.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3083   -0.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5375    0.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7750    2.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125    1.5208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2958    1.3458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0500    2.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708    1.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  1  0
  3  1  1  0
  4  7  1  0
  5 14  1  0
  6  5  1  0
  7  1  2  0
  8  6  2  0
  9  5  2  0
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 11  1  1  0
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 14 17  1  0
 15  4  1  1
 16 11  2  0
 17 15  1  0
 18 11  1  0
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 20 19  1  0
 21 26  2  0
 22  2  1  0
 23 21  1  0
 24 32  1  0
 25 27  2  0
 26 28  1  0
 27 24  1  0
 28 24  2  0
 29 19  1  0
 30 31  1  0
 31 15  1  0
 32 34  1  0
 33 29  1  0
 34 33  1  0
  4 10  1  0
  8  2  1  0
 20 12  2  0
 25 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA340297

   1-[(2R)-4-{5-[3-(4-chlorophenyl)propoxy]-1-methyl-1H-indol-3-yl}-1-hydroxybutan-2-yl]-1H-imidazole-4-carboxamide

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: 481.00

Molecular Weight (Monoisotopic): 480.1928

AlogP: 4.30

#Rotatable Bonds: 11

Polar Surface Area: 95.30

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.82

CX Basic pKa: 3.24

CX LogP: 4.37

CX LogD: 4.37

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.31

Np Likeness Score: -0.61

References

1. Terasaka T, Kinoshita T, Kuno M, Seki N, Tanaka K, Nakanishi I..  (2004)  Structure-based design, synthesis, and structure-activity relationship studies of novel non-nucleoside adenosine deaminase inhibitors.,  47  (15): [PMID:15239652] [10.1021/jm0306374]

2. Terasaka T, Tsuji K, Kato T, Nakanishi I, Kinoshita T, Kato Y, Kuno M, Inoue T, Tanaka K, Nakamura K..  (2005)  Rational design of non-nucleoside, potent, and orally bioavailable adenosine deaminase inhibitors: predicting enzyme conformational change and metabolism.,  48  (15): [PMID:16033254] [10.1021/jm050413g]

Source

Source(1):

• Scientific Literature