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

ID: ALA125386

PubChem CID: 447546

Max Phase: Preclinical

Molecular Formula: C24H26N6O3

Molecular Weight: 446.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cn([C@@H](CO)CCn2ccc3ccc(NC(=O)NCc4ccccc4)cc32)cn1

Standard InChI:  InChI=1S/C24H26N6O3/c25-23(32)21-14-30(16-27-21)20(15-31)9-11-29-10-8-18-6-7-19(12-22(18)29)28-24(33)26-13-17-4-2-1-3-5-17/h1-8,10,12,14,16,20,31H,9,11,13,15H2,(H2,25,32)(H2,26,28,33)/t20-/m1/s1

Standard InChI Key:  KCCUBLLGAMGDJL-HXUWFJFHSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.6257    1.9139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2901    1.1602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9032    0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6177    1.0207    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4462    1.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9982    2.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8052    2.2692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7433    3.2253    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4832    0.9887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311    1.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242    1.4302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2282    0.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4212    0.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1663   -0.7521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6512   -1.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1663   -2.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3817   -1.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3817   -1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3328   -2.2445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0473   -1.8320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0473   -1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3328   -0.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7617   -0.5945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4762   -1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4762   -1.8320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1907   -0.5945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9051   -1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6196    0.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6196   -0.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3341   -1.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0486   -0.5945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0486    0.2305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3341    0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  5  2  0
  3  2  1  0
  9  2  1  1
  3  4  2  0
  5  4  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  9 10  1  0
  9 12  1  0
 10 11  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  0
 18 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 18 22  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 24 23  1  0
 24 25  2  0
 24 26  1  0
 27 26  1  0
 29 27  1  0
 29 28  2  0
 33 28  1  0
 29 30  1  0
 31 30  2  0
 32 31  1  0
 32 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA125386

   1-[(1R)-3-(6-{[(Benzylamino)carbonyl]amino}-1H-indol-1-YL)-1-(hydroxymethyl)propyl]-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: 446.51

Molecular Weight (Monoisotopic): 446.2066

AlogP: 2.88

#Rotatable Bonds: 9

Polar Surface Area: 127.20

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.07

CX Basic pKa: 3.23

CX LogP: 1.72

CX LogD: 1.72

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.32

Np Likeness Score: -1.38

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