2-(3,4,5-trimethoxyphenylmethylene)-cycloheptanone

ID: ALA555374

PubChem CID: 44428796

Max Phase: Preclinical

Molecular Formula: C17H22O4

Molecular Weight: 290.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(/C=C2\CCCCCC2=O)cc(OC)c1OC

Standard InChI:  InChI=1S/C17H22O4/c1-19-15-10-12(11-16(20-2)17(15)21-3)9-13-7-5-4-6-8-14(13)18/h9-11H,4-8H2,1-3H3/b13-9+

Standard InChI Key:  SCDABWNFAVHEPI-UKTHLTGXSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -2.9555  -23.7110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9555  -24.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2441  -24.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296  -24.5299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5296  -23.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2453  -23.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202  -23.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1108  -23.7020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2091  -24.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3481  -25.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3501  -23.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5861  -23.2787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4941  -22.4646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6649  -24.9429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3743  -24.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1830  -25.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6328  -24.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6697  -23.3035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6739  -22.4812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2441  -25.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9562  -26.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  8 12  1  0
  9 10  1  0
 17 11  1  0
 11 12  1  0
 12 13  2  0
  2 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
  1 18  1  0
  1  2  2  0
 18 19  1  0
  2  3  1  0
  3 20  1  0
  3  4  2  0
 20 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA555374

   (2E)-2-[(3,4,5-trimethoxyphenyl)methylidene]cycloheptan-1-one

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: 290.36

Molecular Weight (Monoisotopic): 290.1518

AlogP: 3.63

#Rotatable Bonds: 4

Polar Surface Area: 44.76

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.51

CX LogD: 3.51

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.63

Np Likeness Score: 0.07

References

1. Das U, Kawase M, Sakagami H, Ideo A, Shimada J, Molnár J, Baráth Z, Bata Z, Dimmock JR..  (2007)  3-(3,4,5-Trimethoxyphenyl)-1-oxo-2-propene: a novel pharmacophore displaying potent multidrug resistance reversal and selective cytotoxicity.,  15  (10): [PMID:17383883] [10.1016/j.bmc.2007.03.022]

Source

Source(1):

• Scientific Literature