1-((1R,2S)-1-{2-[2-(4-Chloro-phenyl)-benzooxazol-7-yl]-ethyl}-2-hydroxy-propyl)-1H-imidazole-4-carboxylic acid amide

ID: ALA359803

PubChem CID: 10238071

Max Phase: Preclinical

Molecular Formula: C22H21ClN4O3

Molecular Weight: 424.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](O)[C@@H](CCc1cccc2nc(-c3ccc(Cl)cc3)oc12)n1cnc(C(N)=O)c1

Standard InChI:  InChI=1S/C22H21ClN4O3/c1-13(28)19(27-11-18(21(24)29)25-12-27)10-7-14-3-2-4-17-20(14)30-22(26-17)15-5-8-16(23)9-6-15/h2-6,8-9,11-13,19,28H,7,10H2,1H3,(H2,24,29)/t13-,19+/m0/s1

Standard InChI Key:  SMFRBBHLVBWHGB-ORAYPTAESA-N

Molfile:  

     RDKit          2D

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    1.4500    0.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6125    1.3083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    0.1458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250   -0.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9125   -0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2167    2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0208    3.5875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9125   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8667   -1.2417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6250   -1.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -1.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -2.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
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 23 19  2  0
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 28 29  2  0
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 21 30  1  1
  9  4  1  0
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  3  2  2  0
 22 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA359803

   1-((1R,2S)-1-{2-[2-(4-Chloro-phenyl)-benzooxazol-7-yl]-ethyl}-2-hydroxy-propyl)-1H-imidazole-4-carboxylic acid amide

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: 424.89

Molecular Weight (Monoisotopic): 424.1302

AlogP: 4.00

#Rotatable Bonds: 7

Polar Surface Area: 107.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.81

CX Basic pKa: 3.23

CX LogP: 3.53

CX LogD: 3.53

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.47

Np Likeness Score: -0.69

References

1. Terasaka T, Tsuji K, Kato T, Nakanishi I, Kinoshita T, Kato Y, Kuno M, Inoue T, Tanaka K, Nakamura K..  (2005)  Rational design of non-nucleoside, potent, and orally bioavailable adenosine deaminase inhibitors: predicting enzyme conformational change and metabolism.,  48  (15): [PMID:16033254] [10.1021/jm050413g]

Source

Source(1):

• Scientific Literature