rac-7-chloro-N-(2-(2,4-difluorophenyl)-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

ID: ALA4462376

PubChem CID: 155529329

Max Phase: Preclinical

Molecular Formula: C21H16ClF2N5O3

Molecular Weight: 459.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(NCC(O)(Cn1cncn1)c1ccc(F)cc1F)c1cc2ccc(Cl)cc2[nH]c1=O

Standard InChI:  InChI=1S/C21H16ClF2N5O3/c22-13-2-1-12-5-15(20(31)28-18(12)6-13)19(30)26-8-21(32,9-29-11-25-10-27-29)16-4-3-14(23)7-17(16)24/h1-7,10-11,32H,8-9H2,(H,26,30)(H,28,31)

Standard InChI Key:  IMYFQEKBSJCZJQ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    5.7133   -5.6277    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7035   -6.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9664   -7.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9565   -8.5058    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2574   -7.2569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2714   -6.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2645   -5.4418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.1693   -3.9993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1500   -4.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8528   -5.2466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8848   -3.5960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5920   -4.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5752   -4.8492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2797   -5.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0013   -4.8758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0143   -4.0482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3091   -3.6270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4273   -5.2193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7081   -5.3004    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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 26 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 25  1  0
 22 31  2  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4462376

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 459.84

Molecular Weight (Monoisotopic): 459.0910

AlogP: 2.37

#Rotatable Bonds: 6

Polar Surface Area: 112.90

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.20

CX Basic pKa: 2.26

CX LogP: 2.05

CX LogD: 2.05

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.41

Np Likeness Score: -1.52

References

1. Elias R, Benhamou RI, Jaber QZ, Dorot O, Zada SL, Oved K, Pichinuk E, Fridman M..  (2019)  Antifungal activity, mode of action variability, and subcellular distribution of coumarin-based antifungal azoles.,  179  [PMID:31288127] [10.1016/j.ejmech.2019.07.003]

Source

Source(1):

• Scientific Literature