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

ID: ALA346360

PubChem CID: 10132584

Max Phase: Preclinical

Molecular Formula: C19H18N4O3

Molecular Weight: 350.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(CCn2cnc3c2NC=NCC3O)c2ccccc2c1

Standard InChI:  InChI=1S/C19H18N4O3/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/h1-4,7-8,10-11,16,24H,5-6,9H2,(H,20,21)(H,25,26)

Standard InChI Key:  BHYHIEMPROVLIW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.9667   -2.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -2.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -1.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -2.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -3.3250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -1.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042   -2.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5167   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792   -3.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -3.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -2.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -1.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5667   -2.7625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -1.9250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0917   -2.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -4.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -4.2375    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 11  2  0
  8 18  1  0
  9  7  1  0
 10  1  1  0
 11  8  1  0
 12 14  2  0
 13  5  1  0
 14 15  1  0
 15  8  2  0
 16 22  1  0
 17  4  1  0
 18 17  1  0
 19  9  2  0
 20  9  1  0
 21 10  1  0
 22 10  1  0
 23 14  1  0
 24 15  1  0
 25 26  1  0
 26 24  2  0
  6  4  1  0
 13 16  2  0
 12  7  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA346360

   4-[2-(8-Hydroxy-7,8-dihydro-6H-imidazo[4,5-d][1,3]diazepin-3-yl)-ethyl]-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: 350.38

Molecular Weight (Monoisotopic): 350.1379

AlogP: 2.46

#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: 3.97

CX Basic pKa: 6.50

CX LogP: 0.03

CX LogD: -0.67

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -0.14

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]

Source

Source(1):

• Scientific Literature