(3aS,9bR)-6,9-Dimethyl-3-methylene-2-oxo-2,3,3a,4,5,9b-hexahydronaphtho[1,2-b]furan-8-yl 4-Methylbenzoate

ID: ALA4086066

PubChem CID: 137641744

Max Phase: Preclinical

Molecular Formula: C23H22O4

Molecular Weight: 362.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2c3c(C)c(OC(=O)c4ccc(C)cc4)cc(C)c3CC[C@@H]12

Standard InChI:  InChI=1S/C23H22O4/c1-12-5-7-16(8-6-12)23(25)26-19-11-13(2)17-9-10-18-14(3)22(24)27-21(18)20(17)15(19)4/h5-8,11,18,21H,3,9-10H2,1-2,4H3/t18-,21+/m0/s1

Standard InChI Key:  NIOOVGYICSHBQU-GHTZIAJQSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   15.1354   -2.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1343   -2.8980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8490   -3.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8472   -1.6579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5625   -2.0671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5614   -2.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9941   -2.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2767   -1.6516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9930   -2.8975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2746   -3.3087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4435   -4.1189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2664   -4.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6059   -3.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4135   -3.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8448   -0.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8507   -4.1359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4195   -3.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7053   -2.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9906   -3.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7060   -2.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6762   -4.9247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5576   -3.7165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.7033   -2.4791    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2773   -2.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5629   -3.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5618   -4.1306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2810   -4.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9923   -4.1299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8477   -4.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  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
 13 14  2  0
  4 15  1  0
  3 16  1  0
  2 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 12 21  2  0
 10 22  1  6
  9 23  1  6
 19 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 19  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4086066

   ---

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: 362.43

Molecular Weight (Monoisotopic): 362.1518

AlogP: 4.55

#Rotatable Bonds: 2

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.23

CX LogD: 6.23

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: 1.02

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