1-Bromo-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: ALA346040

Cas Number: 214679-60-4

PubChem CID: 9802899

Max Phase: Preclinical

Molecular Formula: C19H21BrN4O3

Molecular Weight: 433.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(CCn2cnc3c2NC=NCC3O)c2c(c1Br)CCCC2

Standard InChI:  InChI=1S/C19H21BrN4O3/c20-16-13-4-2-1-3-12(13)11(7-14(16)19(26)27)5-6-24-10-23-17-15(25)8-21-9-22-18(17)24/h7,9-10,15,25H,1-6,8H2,(H,21,22)(H,26,27)

Standard InChI Key:  YPFKFJNLCPXDDR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    3.9875   -2.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250   -3.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2292   -2.0792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5625   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -2.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5625   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -3.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8292   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5250   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5250   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917   -2.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917   -3.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -3.8000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4792   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1042   -2.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0750   -3.9542    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    8.6167   -3.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542   -2.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -3.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5125   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917   -4.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4 10  2  0
  5  2  1  0
  6  9  2  0
  7  2  1  0
  8  3  2  0
  9 11  1  0
 10 13  1  0
 11 13  2  0
 12  4  1  0
 13 18  1  0
 14  1  1  0
 15  7  1  0
 16 23  1  0
 17  5  1  0
 18 17  1  0
 19 12  2  0
 20  6  1  0
 21 12  1  0
 22 14  1  0
 23 14  1  0
 24  9  1  0
 25 11  1  0
 26 27  1  0
 27 25  1  0
  8  5  1  0
 15 16  2  0
  6  4  1  0
 24 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA346040

   1-Bromo-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: 433.31

Molecular Weight (Monoisotopic): 432.0797

AlogP: 2.95

#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: 3.42

CX Basic pKa: 6.50

CX LogP: 1.24

CX LogD: 0.54

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: 0.05

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