(S)-1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethyl-4-isopropylphenylcarbamate

ID: ALA3318310

PubChem CID: 76871876

Max Phase: Preclinical

Molecular Formula: C21H22FN3O2

Molecular Weight: 367.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)c1ccc(NC(=O)O[C@H](Cn2ccnc2)c2ccc(F)cc2)cc1

Standard InChI:  InChI=1S/C21H22FN3O2/c1-15(2)16-5-9-19(10-6-16)24-21(26)27-20(13-25-12-11-23-14-25)17-3-7-18(22)8-4-17/h3-12,14-15,20H,13H2,1-2H3,(H,24,26)/t20-/m1/s1

Standard InChI Key:  OMXCIRVMHPGVCD-HXUWFJFHSA-N

Molfile:  

     RDKit          2D

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   17.8843   -4.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.1218   -5.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7093   -6.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8843   -6.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2343   -6.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6468   -5.3165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6468   -6.7454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4092   -6.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9468   -5.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3593   -4.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.9967   -5.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4092   -4.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3323   -3.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7192   -2.5818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0047   -2.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1763   -3.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9967   -3.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1717   -5.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7592   -6.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9343   -6.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5218   -5.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9343   -4.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7592   -4.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6968   -5.3165    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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  3  4  1  0
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 21 26  2  0
 24 27  1  0
 14 21  1  0
 14 10  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3318310

   (1s)-1-(4-Fluorophenyl)-2-(1h-Imidazol-1-Yl)ethyl 4-Isopropylphenylcarbamate

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: 367.42

Molecular Weight (Monoisotopic): 367.1696

AlogP: 5.14

#Rotatable Bonds: 6

Polar Surface Area: 56.15

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.14

CX Basic pKa: 6.77

CX LogP: 4.91

CX LogD: 4.84

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.66

Np Likeness Score: -1.27

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]

2. De Vita D, Pandolfi F, Cirilli R, Scipione L, Di Santo R, Friggeri L, Mori M, Fiorucci D, Maccari G, Arul Christopher RS, Zamperini C, Pau V, De Logu A, Tortorella S, Botta M..  (2016)  Discovery of in vitro antitubercular agents through in silico ligand-based approaches.,  121  [PMID:27240272] [10.1016/j.ejmech.2016.05.032]

Source

Source(1):

• Scientific Literature