(3aS,6R,8S,9bS)-6-Acetoxy-6,9-dimethyl-3-methylene-2-oxo-2,3,3a,4,5,6,6a,7,8,9b-decahydroazuleno[4,5-b]furan-8-yl (E)-3-(4-Bromophenyl)acrylate

ID: ALA4100187

PubChem CID: 137660266

Max Phase: Preclinical

Molecular Formula: C26H27BrO6

Molecular Weight: 515.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2C3=C(C)[C@@H](OC(=O)/C=C/c4ccc(Br)cc4)CC3[C@](C)(OC(C)=O)CC[C@@H]12

Standard InChI:  InChI=1S/C26H27BrO6/c1-14-19-11-12-26(4,33-16(3)28)20-13-21(15(2)23(20)24(19)32-25(14)30)31-22(29)10-7-17-5-8-18(27)9-6-17/h5-10,19-21,24H,1,11-13H2,2-4H3/b10-7+/t19-,20?,21-,24-,26+/m0/s1

Standard InChI Key:  GFLDTJSIDZCSNP-OZDKUXIFSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   16.0549  -17.7512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6369  -18.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8540  -17.5382    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4359  -18.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7943  -19.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9973  -19.6735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9975  -18.8526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2239  -18.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7404  -19.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2219  -19.9225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4352  -20.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6358  -20.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5598  -20.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3123  -21.3219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8548  -20.7058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2720  -16.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4835  -16.1628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4785  -17.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6726  -20.7818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9626  -20.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9191  -19.2547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4914  -22.1233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8362  -20.3885    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2258  -19.7818    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5080  -18.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6866  -18.5401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9223  -17.8311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2797  -17.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4584  -17.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0522  -17.1133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2316  -17.1111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8206  -17.8225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2319  -18.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0511  -18.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9992  -17.8217    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  6
  7  2  1  0
  2  4  1  0
  4  5  1  0
  6 12  1  0
  5 11  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11 15  1  0
  3 16  1  0
 16 17  1  0
 16 18  2  0
 15 19  2  0
 10 20  1  0
  9 21  1  1
 14 22  2  0
 12 23  1  1
 11 24  1  6
 21 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4100187

   ---

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: 515.40

Molecular Weight (Monoisotopic): 514.0991

AlogP: 4.92

#Rotatable Bonds: 4

Polar Surface Area: 78.90

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.10

CX LogD: 5.10

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.25

Np Likeness Score: 2.30

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]

2. Chen H, Yang X, Yu Z, Cheng Z, Yuan H, Zhao Z, Wu G, Xie N, Yuan X, Sun Q, Zhang W..  (2018)  Synthesis and biological evaluation of α-santonin derivatives as anti-hepatoma agents.,  149  [PMID:29499490] [10.1016/j.ejmech.2018.02.073]

Source

Source(1):

• Scientific Literature