(3aS,5aS,8S,9R,9bS)-5a,9-Dimethyl-3-methylene-2-oxododecahydronaphtho[1,2-b]furan-8-yl 3-(Trifluoromethyl)-benzoate

ID: ALA4095972

PubChem CID: 137655712

Max Phase: Preclinical

Molecular Formula: C23H25F3O4

Molecular Weight: 422.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2C3[C@@H](C)C(OC(=O)c4cccc(C(F)(F)F)c4)CC[C@]3(C)CC[C@@H]12

Standard InChI:  InChI=1S/C23H25F3O4/c1-12-16-7-9-22(3)10-8-17(13(2)18(22)19(16)30-20(12)27)29-21(28)14-5-4-6-15(11-14)23(24,25)26/h4-6,11,13,16-19H,1,7-10H2,2-3H3/t13-,16-,17?,18?,19-,22-/m0/s1

Standard InChI Key:  HNFRQOINAHFFTK-GQFGSLMRSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   32.5308  -22.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5308  -23.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2361  -23.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2361  -22.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9414  -22.5966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9379  -23.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3535  -22.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6469  -22.1887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3500  -23.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6405  -23.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8053  -24.6232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6168  -24.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9533  -23.9698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9341  -21.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2283  -24.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8237  -23.8234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1154  -23.4158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4083  -23.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1142  -22.5986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7025  -23.4175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9959  -23.8264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9966  -24.6445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7099  -25.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4136  -24.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0211  -25.4237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.7536  -23.8047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2878  -23.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0555  -23.0052    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.0579  -24.4002    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.2870  -22.6013    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.5805  -23.8278    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.5740  -23.0093    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  9 13  1  0
  5 14  1  1
  3 15  1  1
  2 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 18  1  0
 12 25  2  0
 13 26  2  0
 21 27  1  0
  9 28  1  6
 10 29  1  1
 27 30  1  0
 27 31  1  0
 27 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4095972

   ---

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: 422.44

Molecular Weight (Monoisotopic): 422.1705

AlogP: 5.17

#Rotatable Bonds: 2

Polar Surface Area: 52.60

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.85

CX LogD: 5.85

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.49

Np Likeness Score: 1.50

References

1. Chen H, Wu G, Gao S, Guo R, Zhao Z, Yuan H, Liu S, Wu J, Lu X, Yuan X, Yu Z, Zu X, Xie N, Yang N, Hu Z, Sun Q, Zhang W..  (2017)  Discovery of Potent Small-Molecule Inhibitors of Ubiquitin-Conjugating Enzyme UbcH5c from α-Santonin Derivatives.,  60  (16): [PMID:28696694] [10.1021/acs.jmedchem.6b01829]

Source

Source(1):

• Scientific Literature