methyl 2-(5-chloro-2-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)phenyl)-3-methoxyacrylate

ID: ALA234667

PubChem CID: 44432128

Max Phase: Preclinical

Molecular Formula: C20H18ClN3O3

Molecular Weight: 383.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO/C=C(/C(=O)OC)c1cc(Cl)ccc1Cn1cc(-c2ccccc2)nn1

Standard InChI:  InChI=1S/C20H18ClN3O3/c1-26-13-18(20(25)27-2)17-10-16(21)9-8-15(17)11-24-12-19(22-23-24)14-6-4-3-5-7-14/h3-10,12-13H,11H2,1-2H3/b18-13+

Standard InChI Key:  XWMUDOPICBVUAJ-QGOAFFKASA-N

Molfile:  

     RDKit          2D

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   -0.1889    2.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1901    1.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5247    1.1056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2412    1.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2383    2.3495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5229    2.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9512    2.7647    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5245    0.2806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1900   -0.1317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2389   -0.1320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9535    0.2803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6678   -0.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6190    1.5196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7016    2.3431    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085    2.5152    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219    1.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3699    1.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7490    1.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1561    2.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9803    2.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3984    1.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9863    1.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1635    1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9044    0.2810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1903   -0.9567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9042    1.1060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6190   -0.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 26 13  1  0
 13 14  1  0
  1  2  2  0
  5  7  1  0
  3  4  2  0
  3  8  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
  8  9  1  0
 18 19  2  0
  4  5  1  0
 19 20  1  0
  8 10  2  0
 20 21  2  0
  2  3  1  0
 21 22  1  0
 10 11  1  0
 22 23  2  0
 23 18  1  0
 16 18  1  0
  5  6  2  0
  9 24  1  0
 11 12  1  0
  9 25  2  0
  2 26  1  0
  6  1  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA234667

   methyl (E)-2-[5-chloro-2-[(4-phenyltriazol-1-yl)methyl]phenyl]-3-methoxyprop-2-enoate

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: 383.84

Molecular Weight (Monoisotopic): 383.1037

AlogP: 3.81

#Rotatable Bonds: 6

Polar Surface Area: 66.24

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.51

CX LogD: 4.51

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: -0.90

References

1. Chen H, Taylor JL, Abrams SR..  (2007)  Design and synthesis of beta-methoxyacrylate analogues via click chemistry and biological evaluations.,  17  (7): [PMID:17300931] [10.1016/j.bmcl.2007.01.021]

Source

Source(1):

• Scientific Literature