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

ID: ALA156217

PubChem CID: 10598664

Max Phase: Preclinical

Molecular Formula: C19H17BrN4O3

Molecular Weight: 429.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(CCn2cnc3c2NC=NCC3O)c2cc(Br)ccc2c1

Standard InChI:  InChI=1S/C19H17BrN4O3/c20-14-2-1-11-5-13(19(26)27)6-12(15(11)7-14)3-4-24-10-23-17-16(25)8-21-9-22-18(17)24/h1-2,5-7,9-10,16,25H,3-4,8H2,(H,21,22)(H,26,27)

Standard InChI Key:  AJEMOPXEMMOAAC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    4.0375   -0.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4750   -1.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -0.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -0.9417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4292   -1.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5500   -1.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5500   -1.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1125   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0625   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500   -0.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0750   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5875   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -2.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3625   -2.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5125   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250   -2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375   -0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1250   -0.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0625   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0250   -2.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6292   -1.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -0.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5375   -3.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5042   -3.0500    0.0000 Br  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 13  2  0
  8  9  2  0
  9 19  1  0
 10  7  1  0
 11  8  1  0
 12  1  1  0
 13  9  1  0
 14  7  1  0
 15  5  1  0
 16 25  1  0
 17  4  1  0
 18  8  1  0
 19 17  1  0
 20 10  2  0
 21 11  1  0
 22 18  2  0
 23 10  1  0
 24 12  1  0
 25 12  1  0
 26 22  1  0
 27 22  1  0
  6  4  1  0
 15 16  2  0
 14 11  2  0
 21 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA156217

   6-Bromo-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: 429.27

Molecular Weight (Monoisotopic): 428.0484

AlogP: 3.23

#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: 0.80

CX LogD: 0.09

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: -0.09

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