1-(4-(4-(((2r,5r)-2-((1H-imidazol-1-yl)methyl)-2-(2-chlorophenyl)-1,3-dioxan-5-yloxy)methyl)phenyl)piperazin-1-yl)ethanone

ID: ALA4285744

Max Phase: Preclinical

Molecular Formula: C27H31ClN4O4

Molecular Weight: 511.02

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCN(c2ccc(CO[C@H]3CO[C@@](Cn4ccnc4)(c4ccccc4Cl)OC3)cc2)CC1

Standard InChI:  InChI=1S/C27H31ClN4O4/c1-21(33)31-12-14-32(15-13-31)23-8-6-22(7-9-23)16-34-24-17-35-27(36-18-24,19-30-11-10-29-20-30)25-4-2-3-5-26(25)28/h2-11,20,24H,12-19H2,1H3/t24-,27+

Standard InChI Key:  KXAVEJVPHQCMQP-FEGDYQJNSA-N

Molfile:  

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   34.1157   -5.4163    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4285744

   ---

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: 511.02

Molecular Weight (Monoisotopic): 510.2034

AlogP: 3.69

#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: 3.62

CX LogD: 3.59

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.48

Np Likeness Score: -0.77

References

1.  (2016)  Novel functionalized 5-(phenoxymethyl)-1,3-dioxane analogs exhibiting cytochrome p450 inhibition and their method of use, 

2. Blass, Benjamin E BE and 18 more authors.  2016-12-01  Design, synthesis, and evaluation of (2S,4R)-Ketoconazole sulfonamide analogs as potential treatments for Metabolic Syndrome.  [PMID:27789139]

3. Fehl, Charlie C and 5 more authors.  2018-06-14  Structure-Based Design of Inhibitors with Improved Selectivity for Steroidogenic Cytochrome P450 17A1 over Cytochrome P450 21A2.  [PMID:29792703]

Source

Source(1):

• Patent Bioactivity Data