Methyl 4-((E)-2-(methoxycarbonyl)vinyloxy)-5-phenylhex-2-ynoate

ID: ALA1097283

PubChem CID: 46887364

Max Phase: Preclinical

Molecular Formula: C17H18O5

Molecular Weight: 302.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C#CC(O/C=C/C(=O)OC)C(C)c1ccccc1

Standard InChI:  InChI=1S/C17H18O5/c1-13(14-7-5-4-6-8-14)15(9-10-16(18)20-2)22-12-11-17(19)21-3/h4-8,11-13,15H,1-3H3/b12-11+

Standard InChI Key:  FVHJDHJQLJVSAI-VAWYXSNFSA-N

Molfile:  

     RDKit          2D

 22 22  0  0  0  0  0  0  0  0999 V2000
    6.7573    0.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5826    0.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3568    1.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3365   -0.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4090    0.5702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2345    0.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5313    1.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1267    2.0346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3013    2.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9008    2.7675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8805    1.3368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    1.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6516    1.2776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6471   -0.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2300   -0.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7370   -0.8463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0861   -0.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5099   -0.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1074    0.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2854    0.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8674   -0.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683   -0.8133    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
  4 18  1  0
  7  8  2  0
  4 16  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:

   

   ALA1097283

   methyl 4-[(E)-3-methoxy-3-oxoprop-1-enoxy]-5-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: 2.04

#Rotatable Bonds: 5

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: 3.51

CX LogD: 3.51

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.27

Np Likeness Score: 0.62

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