1-{(R)-1-Hydroxymethyl-3-[6-(3-phenyl-propoxy)-indol-1-yl]-propyl}-1H-imidazole-4-carboxylic acid amide

ID: ALA332298

PubChem CID: 11373857

Max Phase: Preclinical

Molecular Formula: C25H28N4O3

Molecular Weight: 432.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cn([C@@H](CO)CCn2ccc3ccc(OCCCc4ccccc4)cc32)cn1

Standard InChI:  InChI=1S/C25H28N4O3/c26-25(31)23-16-29(18-27-23)21(17-30)11-13-28-12-10-20-8-9-22(15-24(20)28)32-14-4-7-19-5-2-1-3-6-19/h1-3,5-6,8-10,12,15-16,18,21,30H,4,7,11,13-14,17H2,(H2,26,31)/t21-/m1/s1

Standard InChI Key:  YXYLHUPSWCCNBG-OAQYLSRUSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  1  0  0  0  0  0999 V2000
    5.2875    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917    1.2208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -0.1125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2000    0.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1042   -1.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000   -1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750    1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1917   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5042   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -0.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917    1.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8500    2.4083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208    1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -0.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9042   -1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4083    1.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458    1.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167    0.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0583    1.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8208    2.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6458    2.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  1  2  0
  5 13  1  0
  6  2  2  0
  7  5  1  0
  8  1  1  0
  9  5  1  0
 10  9  2  0
 11  7  1  0
 12  7  2  0
 13 14  1  0
 14 15  1  0
 15  3  1  1
 16  8  2  0
 17 11  2  0
 18  8  1  0
 19 12  1  0
 20 19  2  0
 21 19  1  0
 22 25  1  0
 23 24  1  0
 24 15  1  0
 25 29  1  0
 26 21  1  0
 27 22  2  0
 28 22  1  0
 29 26  1  0
 30 28  2  0
 31 27  1  0
 32 30  1  0
  3  6  1  0
 11 10  1  0
 17 20  1  0
 31 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA332298

   1-[(2R)-1-hydroxy-4-[6-(3-phenylpropoxy)-1H-indol-1-yl]butan-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: 432.52

Molecular Weight (Monoisotopic): 432.2161

AlogP: 3.57

#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: 3.23

CX LogP: 3.17

CX LogD: 3.17

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.35

Np Likeness Score: -0.74

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]

Source

Source(1):

• Scientific Literature