4-[2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid

ID: ALA157949

PubChem CID: 10546056

Max Phase: Preclinical

Molecular Formula: C19H22N4O3

Molecular Weight: 354.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc2c(c(CCn3cnc4c3NC=NCC4O)c1)CCCC2

Standard InChI:  InChI=1S/C19H22N4O3/c24-16-9-20-10-21-18-17(16)22-11-23(18)6-5-13-8-14(19(25)26)7-12-3-1-2-4-15(12)13/h7-8,10-11,16,24H,1-6,9H2,(H,20,21)(H,25,26)

Standard InChI Key:  QYLCLEVVCQXKFN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    4.2792   -3.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7167   -3.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -2.9042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -3.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -4.4542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542   -3.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3792   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6875   -3.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542   -4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3375   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1792   -4.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -4.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7625   -3.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -3.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3917   -2.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9042   -3.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -3.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3250   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2792   -5.3750    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 14  2  0
  8 18  1  0
  9  7  1  0
 10 11  1  0
 11  8  2  0
 12  1  1  0
 13  7  1  0
 14  8  1  0
 15  5  1  0
 16 22  1  0
 17  4  1  0
 18 17  1  0
 19  9  2  0
 20  9  1  0
 21 12  1  0
 22 12  1  0
 23 10  1  0
 24 11  1  0
 25 26  1  0
 26 24  1  0
  6  4  1  0
 15 16  2  0
 13 10  2  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA157949

   4-[2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic 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: 354.41

Molecular Weight (Monoisotopic): 354.1692

AlogP: 2.19

#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: 4.21

CX Basic pKa: 6.50

CX LogP: 0.52

CX LogD: -0.19

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.78

Np Likeness Score: 0.15

References

1. 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]

2. 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