2-Methyl-2-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-cyclopropanecarboxylic acid ethyl ester

ID: ALA2115168

PubChem CID: 71450987

Max Phase: Preclinical

Molecular Formula: C23H34O2

Molecular Weight: 342.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)[C@@H]1C[C@@]1(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C

Standard InChI:  InChI=1S/C23H34O2/c1-7-25-21(24)20-16-23(20,6)15-8-10-17(2)12-13-19-18(3)11-9-14-22(19,4)5/h8,10,12-13,15,20H,7,9,11,14,16H2,1-6H3/b13-12+,15-8+,17-10+/t20-,23+/m0/s1

Standard InChI Key:  MTGJEKMTXCEFTB-PWZHTVMVSA-N

Molfile:  

     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    1.3445    2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0585    2.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9394    2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4593    0.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6534    0.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3715    2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2254    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6305    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835    2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114    2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7974    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2860    0.8851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6263    2.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0459    0.1712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3715    0.3633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0813    1.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9394    0.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9665    2.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    2.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0938    0.7766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5114    2.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2192    0.1712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8059   -0.5428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  5  1  0
  5  9  2  0
  2  6  1  1
  7  4  2  0
  8  4  1  0
  9 12  1  0
 10  1  1  0
 11 10  2  0
 12 13  2  0
 13 11  1  0
 14  6  2  0
  1 15  1  1
 16  6  1  0
 17  7  1  0
 18  8  1  0
 19  7  1  0
 20  8  1  0
 21  8  1  0
 22 18  1  0
 23 12  1  0
 24 16  1  0
 25 24  1  0
  2  3  1  0
 22 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2115168

   ethyl (1R,2S)-2-methyl-2-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hexa-1,3,5-trienyl]cyclopropane-1-carboxylate

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: 342.52

Molecular Weight (Monoisotopic): 342.2559

AlogP: 6.16

#Rotatable Bonds: 6

Polar Surface Area: 26.30

Molecular Species: ┄

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.50

CX LogD: 5.50

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.43

Np Likeness Score: 1.93

References

1. Wong MF, Repa JJ, Clagett-Dame M, Curley RW.  (1997)  Synthesis and receptor binding affinity of conformationally restricted retinoic acid analogues,  7  (17): [10.1016/S0960-894X(97)00420-4]

Source

Source(1):

• Scientific Literature