1-(4-{4-[2-(2,4-Dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-ethanone

ID: ALA328863

Cas Number: 83374-59-8

PubChem CID: 12854713

Product Number: R339297, Order Now?

Max Phase: Preclinical

Molecular Formula: C26H28Cl2N4O4

Molecular Weight: 531.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCN(c2ccc(OC[C@@H]3CO[C@](Cn4ccnc4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1

Standard InChI:  InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26+/m1/s1

Standard InChI Key:  XMAYWYJOQHXEEK-BVAGGSTKSA-N

Molfile:  

     RDKit          2D

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    2.3542   -7.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9375   -3.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -2.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2500   -8.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -9.8792    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -5.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.8792   -0.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1
  3  1  1  0
  4 19  1  0
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  1 11  1  6
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 16 32  1  1
 33 31  2  0
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 16 24  1  0
 17  9  1  0
 27 14  1  0
 25 15  2  0
 18  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA328863

   rac-trans-Ketoconazole

Molecule Features

Natural Product: Yes

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: 531.44

Molecular Weight (Monoisotopic): 530.1488

AlogP: 4.21

#Rotatable Bonds: 7

Polar Surface Area: 69.06

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.42

CX LogP: 4.19

CX LogD: 4.16

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.46

Np Likeness Score: -0.77

References

1. Rotstein DM, Kertesz DJ, Walker KA, Swinney DC..  (1992)  Stereoisomers of ketoconazole: preparation and biological activity.,  35  (15): [PMID:1495014] [10.1021/jm00093a015]

2. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

Source

Source(2):

• Scientific Literature
• IMI-CARE SARS-CoV-2 Data