1-[(R)-3-(6-Butoxy-indol-1-yl)-1-hydroxymethyl-propyl]-1H-imidazole-4-carboxylic acid amide

ID: ALA125275

PubChem CID: 11394608

Max Phase: Preclinical

Molecular Formula: C20H26N4O3

Molecular Weight: 370.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOc1ccc2ccn(CC[C@H](CO)n3cnc(C(N)=O)c3)c2c1

Standard InChI:  InChI=1S/C20H26N4O3/c1-2-3-10-27-17-5-4-15-6-8-23(19(15)11-17)9-7-16(13-25)24-12-18(20(21)26)22-14-24/h4-6,8,11-12,14,16,25H,2-3,7,9-10,13H2,1H3,(H2,21,26)/t16-/m1/s1

Standard InChI Key:  HKEHYJMEICETAY-MRXNPFEDSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  1  0  0  0  0  0999 V2000
    4.6917    1.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5000    1.9583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542    0.6250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042    0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5125   -1.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2875   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2875   -0.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -0.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9125   -0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5250   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917    2.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625   -1.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542    3.1458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4667   -0.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0542    0.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9250    0.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3042   -0.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0083    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208    2.0083    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 23  1  0
 23 15  1  0
 24 21  1  0
 25 24  1  0
 26 25  1  0
 27 26  1  0
  3  6  1  0
 11 10  1  0
 20 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA125275

   1-[(2R)-4-(6-butoxy-1H-indol-1-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: 370.45

Molecular Weight (Monoisotopic): 370.2005

AlogP: 2.74

#Rotatable Bonds: 10

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: 2.03

CX LogD: 2.03

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.54

Np Likeness Score: -0.82

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