2-Benzyl-6-(8-hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-hexanoic acid H2O.0.2CH3CO2H

ID: ALA35929

PubChem CID: 9820070

Max Phase: Preclinical

Molecular Formula: C19H24N4O3

Molecular Weight: 356.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C(CCCCn1cnc2c1NC=NCC2O)Cc1ccccc1

Standard InChI:  InChI=1S/C19H24N4O3/c24-16-11-20-12-21-18-17(16)22-13-23(18)9-5-4-8-15(19(25)26)10-14-6-2-1-3-7-14/h1-3,6-7,12-13,15-16,24H,4-5,8-11H2,(H,20,21)(H,25,26)

Standard InChI Key:  KENABUKLZKAHBP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -0.7958   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000   -2.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2583   -2.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -2.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0625   -3.2667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3500   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6833   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -2.8750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -4.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875   -5.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3458   -1.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9333   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -5.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -3.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9292   -4.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -6.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -5.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  2  1  0
  6  3  2  0
  7  1  1  0
  8 11  1  0
  9  5  1  0
 10 17  1  0
 11 19  1  0
 12  8  2  0
 13 11  1  0
 14  8  1  0
 15  7  1  0
 16  4  1  0
 17  7  1  0
 18 13  1  0
 19 23  1  0
 20 18  2  0
 21 18  1  0
 22 16  1  0
 23 22  1  0
 24 21  2  0
 25 20  1  0
 26 24  1  0
  6  4  1  0
  9 10  2  0
 26 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA35929

   2-Benzyl-6-(8-hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-hexanoic 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: 356.43

Molecular Weight (Monoisotopic): 356.1848

AlogP: 2.48

#Rotatable Bonds: 8

Polar Surface Area: 99.74

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.96

CX Basic pKa: 6.51

CX LogP: 0.38

CX LogD: -0.32

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: -0.08

References

1. Bookser BC, Kasibhatla SR, Appleman JR, Erion MD..  (2000)  AMP deaminase inhibitors. 2. Initial discovery of a non-nucleotide transition-state inhibitor series.,  43  (8): [PMID:10780906] [10.1021/jm990447m]

2. Kasibhatla SR, Bookser BC, Xiao W, Erion MD..  (2001)  AMP deaminase inhibitors. 5. Design, synthesis, and SAR of a highly potent inhibitor series.,  44  (4): [PMID:11170651] [10.1021/jm000355t]

Source

Source(1):

• Scientific Literature