Methyl 4-((E)-2-(methoxycarbonyl)vinyloxy)non-2-ynoate

ID: ALA1094779

PubChem CID: 46887312

Max Phase: Preclinical

Molecular Formula: C14H20O5

Molecular Weight: 268.31

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C14H20O5/c1-4-5-6-7-12(8-9-13(15)17-2)19-11-10-14(16)18-3/h10-12H,4-7H2,1-3H3/b11-10+

Standard InChI Key:  LPEWIYOOYMXULY-ZHACJKMWSA-N

Molfile:  

     RDKit          2D

 19 18  0  0  0  0  0  0  0  0999 V2000
    6.3664  -14.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1913  -14.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9642  -14.2051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9438  -15.6339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0171  -14.9398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8421  -14.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1392  -14.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7370  -13.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9121  -13.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5098  -12.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4894  -14.1698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6645  -14.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2569  -14.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2524  -15.6582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8376  -16.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1188  -15.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6962  -16.3307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8713  -16.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4486  -17.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  2  0
  1  3  1  0
  9 11  1  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 17  1  0
  8  9  1  0
 17 18  1  0
  2  5  3  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094779

   methyl 4-[(E)-3-methoxy-3-oxoprop-1-enoxy]non-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: 268.31

Molecular Weight (Monoisotopic): 268.1311

AlogP: 1.81

#Rotatable Bonds: 7

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: 3.34

CX LogD: 3.34

Aromatic Rings: ┄

Heavy Atoms: 19

QED Weighted: 0.18

Np Likeness Score: 1.05

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]

2. Silveira-Dorta G, Sousa IJ, Ríos-Luci C, Martín VS, Fernandes MX, Padrón JM..  (2013)  Molecular docking studies of the interaction between propargylic enol ethers and human DNA topoisomerase IIα.,  23  (19): [PMID:23953196] [10.1016/j.bmcl.2013.07.055]

Source

Source(1):

• Scientific Literature