(3aS,9bR)-8-Hydroxy-6,9-dimethyl-3-methylene-3a,4,5,9b-tetrahydronaphtho[1,2-b]furan-2(3H)-one

ID: ALA4086638

PubChem CID: 137409942

Max Phase: Preclinical

Molecular Formula: C15H16O3

Molecular Weight: 244.29

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C15H16O3/c1-7-6-12(16)9(3)13-10(7)4-5-11-8(2)15(17)18-14(11)13/h6,11,14,16H,2,4-5H2,1,3H3/t11-,14+/m0/s1

Standard InChI Key:  NDVJGWDQEJDWTD-SMDDNHRTSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   23.9787  -10.5967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9776  -11.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6922  -11.8366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6904  -10.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4056  -10.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4044  -11.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8367  -10.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1195  -10.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8356  -11.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1173  -11.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2863  -12.6445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1089  -12.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4483  -11.9795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2557  -11.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6879   -9.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6939  -12.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2631  -11.8357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.5186  -13.4500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4006  -12.2421    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.5458  -11.0050    0.0000 H   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
 12 18  2  0
 10 19  1  6
  9 20  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4086638

   ---

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: 244.29

Molecular Weight (Monoisotopic): 244.1099

AlogP: 2.73

#Rotatable Bonds: ┄

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.15

CX Basic pKa: ┄

CX LogP: 3.76

CX LogD: 3.76

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.56

Np Likeness Score: 2.29

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