1-(adamantan-1-yl)-2-(1H-imidazol-1-yl)ethanone hydrochloride

ID: ALA493448

PubChem CID: 25132859

Max Phase: Preclinical

Molecular Formula: C15H21ClN2O

Molecular Weight: 244.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(Cn1ccnc1)C12CC3CC(CC(C3)C1)C2

Standard InChI:  InChI=1S/C15H20N2O.ClH/c18-14(9-17-2-1-16-10-17)15-6-11-3-12(7-15)5-13(4-11)8-15;/h1-2,10-13H,3-9H2;1H

Standard InChI Key:  BOCVFOQNPUSEIG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 21  0  0  0  0  0  0  0  0999 V2000
    9.2645  -19.8333    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.2553  -19.5252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8965  -18.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597  -19.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6079  -19.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8124  -19.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3557  -18.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0570  -18.4518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6136  -17.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8920  -18.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3615  -18.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1959  -21.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3709  -21.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1141  -20.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7834  -19.7458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4484  -20.2326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7846  -18.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0708  -18.5072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0720  -17.6822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3 10  1  0
  7 11  1  0
 11  9  1  0
  9 10  1  0
 12 13  1  0
  2  3  1  0
  2  4  1  0
  3  5  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
  4  6  1  0
 15 17  1  0
  5  7  1  0
 17 18  1  0
  6  7  1  0
 18 19  2  0
 18  7  1  0
  8  9  1  0
  4  8  1  0
M  END

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: 244.34

Molecular Weight (Monoisotopic): 244.1576

AlogP: 2.67

#Rotatable Bonds: 3

Polar Surface Area: 34.89

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.73

CX LogP: 2.49

CX LogD: 2.43

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.82

Np Likeness Score: -0.98

References

1. Rahman MN, Vlahakis JZ, Szarek WA, Nakatsu K, Jia Z..  (2008)  X-ray crystal structure of human heme oxygenase-1 in complex with 1-(adamantan-1-yl)-2-(1H-imidazol-1-yl)ethanone: a common binding mode for imidazole-based heme oxygenase-1 inhibitors.,  51  (19): [PMID:18798608] [10.1021/jm800505m]

Source

Source(1):

• Scientific Literature