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

ID: ALA157951

PubChem CID: 10713804

Max Phase: Preclinical

Molecular Formula: C20H20N4O3

Molecular Weight: 364.41

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H20N4O3/c1-27-20(26)15-8-13-4-2-3-5-16(13)14(9-15)6-7-24-12-23-18-17(25)10-21-11-22-19(18)24/h2-5,8-9,11-12,17,25H,6-7,10H2,1H3,(H,21,22)

Standard InChI Key:  SULFMPMRSCCZRA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.5292   -1.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -0.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0625   -1.4500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4917   -2.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2042   -1.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -1.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1417   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -2.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2167   -0.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7250   -1.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -0.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125   -1.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1375   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -2.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6167   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -3.2667    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
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 16 22  1  0
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 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 20  1  0
 26 27  1  0
 27 24  2  0
  6  4  1  0
 13 16  2  0
 12  7  1  0
 23 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA157951

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

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: 364.41

Molecular Weight (Monoisotopic): 364.1535

AlogP: 2.55

#Rotatable Bonds: 4

Polar Surface Area: 88.74

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.06

CX Basic pKa: 6.50

CX LogP: 1.95

CX LogD: 1.90

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.69

Np Likeness Score: -0.23

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