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

ID: ALA4099738

PubChem CID: 137660477

Max Phase: Preclinical

Molecular Formula: C22H20O4S

Molecular Weight: 380.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2c3c(C)c(OC(=O)/C=C/c4cccs4)cc(C)c3CC[C@@H]12

Standard InChI:  InChI=1S/C22H20O4S/c1-12-11-18(25-19(23)9-6-15-5-4-10-27-15)14(3)20-16(12)7-8-17-13(2)22(24)26-21(17)20/h4-6,9-11,17,21H,2,7-8H2,1,3H3/b9-6+/t17-,21+/m0/s1

Standard InChI Key:  BBDKZDDFGJUCSC-ROORDGKBSA-N

Molfile:  

     RDKit          2D

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   15.0478  -18.7657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0467  -19.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7614  -20.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7596  -18.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4750  -18.7620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4738  -19.5904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9065  -18.7641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1890  -18.3465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9054  -19.5925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1869  -20.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3559  -20.8139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1787  -20.9036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5182  -20.1488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3258  -19.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7571  -17.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7631  -20.8308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3319  -20.0049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6178  -19.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9030  -20.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6184  -18.7669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5885  -21.6196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4700  -20.4115    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6158  -19.1740    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1890  -19.5907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4741  -20.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7231  -19.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1706  -20.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5825  -20.9994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3895  -20.8284    0.0000 S   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 29  1  0
 29 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099738

   ---

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: 380.46

Molecular Weight (Monoisotopic): 380.1082

AlogP: 4.70

#Rotatable Bonds: 3

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.17

CX LogD: 6.17

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: 0.64

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