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

ID: ALA4102445

PubChem CID: 137659882

Max Phase: Preclinical

Molecular Formula: C24H20F2O4

Molecular Weight: 410.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@H]2c3c(C)c(OC(=O)/C=C/c4ccc(F)cc4F)cc(C)c3CC[C@@H]12

Standard InChI:  InChI=1S/C24H20F2O4/c1-12-10-20(29-21(27)9-5-15-4-6-16(25)11-19(15)26)14(3)22-17(12)7-8-18-13(2)24(28)30-23(18)22/h4-6,9-11,18,23H,2,7-8H2,1,3H3/b9-5+/t18-,23+/m0/s1

Standard InChI Key:  CIKSHORJDDSZGR-NMZWHVSPSA-N

Molfile:  

     RDKit          2D

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   42.9938   -7.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.9926   -8.0522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7074   -8.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7056   -6.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4210   -7.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   45.8526   -7.2233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1350   -6.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.8514   -8.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.1330   -8.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.3019   -9.2731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.1249   -9.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.4643   -8.6079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.2719   -8.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7031   -5.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7090   -9.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.2778   -8.4641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   41.5643   -7.2261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.5345  -10.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.4160   -8.8707    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   46.5618   -7.6332    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   40.1348   -8.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4199   -8.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7093   -8.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9950   -8.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9939   -9.2850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7130   -9.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4245   -9.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1406   -9.6938    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.2797   -9.6979    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  5  4  2  0
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 12 13  1  0
  9 13  1  0
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  4 15  1  0
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  2 17  1  0
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 18 20  2  0
 12 21  2  0
 10 22  1  6
  9 23  1  6
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 30 25  1  0
 30 31  1  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4102445

   ---

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: 410.42

Molecular Weight (Monoisotopic): 410.1330

AlogP: 4.92

#Rotatable Bonds: 3

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: 6.55

CX LogD: 6.55

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.41

Np Likeness Score: 0.73

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