Methyl 4-((E)-2-(methoxycarbonyl)vinyloxy)-6-phenylhex-2-ynoate

ID: ALA1096974

PubChem CID: 46887317

Max Phase: Preclinical

Molecular Formula: C17H18O5

Molecular Weight: 302.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C#CC(CCc1ccccc1)O/C=C/C(=O)OC

Standard InChI:  InChI=1S/C17H18O5/c1-20-16(18)11-10-15(22-13-12-17(19)21-2)9-8-14-6-4-3-5-7-14/h3-7,12-13,15H,8-9H2,1-2H3/b13-12+

Standard InChI Key:  AJYJTJKVEVLGQW-OUKQBFOZSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
   -1.0537    0.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284    0.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4540    1.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4743    0.1611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5977    0.8520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229    0.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2792    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6838    2.3202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5089    2.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9094    3.0530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9297    1.6226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7549    1.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    1.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8354    0.1329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4184   -0.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2995    0.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3198   -1.2576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7202   -0.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5402   -0.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9608   -1.2297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -1.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7408   -1.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 11 12  1  0
  1  2  1  0
  6 13  2  0
  3  7  1  0
  6 14  1  0
  1  4  1  0
 14 15  1  0
  7  8  2  0
  4 16  1  0
 16 18  1  0
  8  9  1  0
 17 18  2  0
  2  5  3  0
 18 19  1  0
  9 10  2  0
 19 20  2  0
  1  3  1  0
 20 21  1  0
  9 11  1  0
 21 22  2  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096974

   methyl 4-[(E)-3-methoxy-3-oxoprop-1-enoxy]-6-phenylhex-2-ynoate

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: 302.33

Molecular Weight (Monoisotopic): 302.1154

AlogP: 1.87

#Rotatable Bonds: 6

Polar Surface Area: 61.83

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.26

Np Likeness Score: 0.72

References

1. León LG, Ríos-Luci C, Tejedor D, Pérez-Roth E, Montero JC, Pandiella A, García-Tellado F, Padrón JM..  (2010)  Mitotic arrest induced by a novel family of DNA topoisomerase II inhibitors.,  53  (9): [PMID:20405921] [10.1021/jm100155y]

Source

Source(1):

• Scientific Literature