3-[2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-benzoic acid (1.1H2O)

ID: ALA35524

PubChem CID: 10780561

Max Phase: Preclinical

Molecular Formula: C15H16N4O3

Molecular Weight: 300.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cccc(CCn2cnc3c2NC=NCC3O)c1

Standard InChI:  InChI=1S/C15H16N4O3/c20-12-7-16-8-17-14-13(12)18-9-19(14)5-4-10-2-1-3-11(6-10)15(21)22/h1-3,6,8-9,12,20H,4-5,7H2,(H,16,17)(H,21,22)

Standard InChI Key:  NDZNCVGWUGOBIF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -0.8208   -5.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8083   -6.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458   -5.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -7.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4458   -7.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4542   -6.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1042  -10.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4750   -5.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917  -10.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6250   -6.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0250   -7.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -9.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167  -10.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125  -11.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750   -9.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6792   -8.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833   -4.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2750   -5.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750  -10.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0458  -10.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375   -9.5167    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 10  1  0
  8  1  1  0
  9  5  1  0
 10 13  2  0
 11 19  1  0
 12  4  1  0
 13 16  1  0
 14  7  2  0
 15  7  1  0
 16 17  1  0
 17 12  1  0
 18  8  1  0
 19  8  1  0
 20 21  2  0
 21 22  1  0
 22 16  2  0
  6  4  1  0
  9 11  2  0
 20 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA35524

   3-[2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-benzoic 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: 300.32

Molecular Weight (Monoisotopic): 300.1222

AlogP: 1.31

#Rotatable Bonds: 4

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: 4.05

CX Basic pKa: 6.50

CX LogP: -0.95

CX LogD: -1.66

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: -0.29

References

1. Kasibhatla SR, Bookser BC, Probst G, Appleman JR, Erion MD..  (2000)  AMP deaminase inhibitors. 3. SAR of 3-(carboxyarylalkyl)coformycin aglycon analogues.,  43  (8): [PMID:10780907] [10.1021/jm990448e]

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]

3. Lindell SD, Maechling S, Sabina RL..  (2010)  Synthesis and Biochemical Testing of 3-(Carboxyphenylethyl)imidazo[2,1-f][1,2,4]triazines as Inhibitors of AMP Deaminase.,  1  (6): [PMID:24900209] [10.1021/ml100092a]

Source

Source(1):

• Scientific Literature