(R)-1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl 4-[4-(3,4-dichlorophenyl)-piperazin-1-yl]phenylcarbamate

ID: ALA3318325

PubChem CID: 76871875

Max Phase: Preclinical

Molecular Formula: C28H25Cl4N5O2

Molecular Weight: 605.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(N2CCN(c3ccc(Cl)c(Cl)c3)CC2)cc1)O[C@@H](Cn1ccnc1)c1ccc(Cl)cc1Cl

Standard InChI:  InChI=1S/C28H25Cl4N5O2/c29-19-1-7-23(25(31)15-19)27(17-35-10-9-33-18-35)39-28(38)34-20-2-4-21(5-3-20)36-11-13-37(14-12-36)22-6-8-24(30)26(32)16-22/h1-10,15-16,18,27H,11-14,17H2,(H,34,38)/t27-/m0/s1

Standard InChI Key:  RKYWJGOKHMLHHS-MHZLTWQESA-N

Molfile:  

     RDKit          2D

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   12.9085   -4.6672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3374   -3.8422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0519   -3.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.4808   -5.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   20.0532   -6.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.6242   -7.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7677   -7.5548    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.7677   -5.9047    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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   10.6787   -5.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8718   -6.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4593   -5.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0113   -4.7441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.1940   -5.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.9085   -7.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4795   -7.1422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4795   -6.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1940   -8.3798    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   13.6229   -5.9047    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  5  6  1  0
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  9 10  1  0
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  8 11  1  0
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 25  4  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3318325

   (1r)-1-(2,4-Dichlorophenyl)-2-(1h-Imidazol-1-Yl)ethyl {4-[4-(3,4-Dichlorophenyl)piperazin-1-Yl]phenyl}carbamate

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: 605.35

Molecular Weight (Monoisotopic): 603.0762

AlogP: 7.81

#Rotatable Bonds: 7

Polar Surface Area: 62.63

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 13.60

CX Basic pKa: 6.77

CX LogP: 7.78

CX LogD: 7.72

Aromatic Rings: 4

Heavy Atoms: 39

QED Weighted: 0.23

Np Likeness Score: -1.32

References

1. Friggeri L, Hargrove TY, Rachakonda G, Williams AD, Wawrzak Z, Di Santo R, De Vita D, Waterman MR, Tortorella S, Villalta F, Lepesheva GI..  (2014)  Structural basis for rational design of inhibitors targeting Trypanosoma cruzi sterol 14α-demethylase: two regions of the enzyme molecule potentiate its inhibition.,  57  (15): [PMID:25033013] [10.1021/jm500739f]

Source

Source(1):

• Scientific Literature