(1'S,6'R)-3'-(benzylsulfinyl)-7-chloro-4,6-dimethoxy-6'-methyl-3H-spiro[benzofuran-2,1'-cyclohex[2]ene]-3,4'-dione

ID: ALA3402425

PubChem CID: 73053110

Max Phase: Preclinical

Molecular Formula: C23H21ClO6S

Molecular Weight: 460.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c2c(c1Cl)O[C@@]1(C=C([S+]([O-])Cc3ccccc3)C(=O)C[C@H]1C)C2=O

Standard InChI:  InChI=1S/C23H21ClO6S/c1-13-9-15(25)18(31(27)12-14-7-5-4-6-8-14)11-23(13)22(26)19-16(28-2)10-17(29-3)20(24)21(19)30-23/h4-8,10-11,13H,9,12H2,1-3H3/t13-,23-,31?/m1/s1

Standard InChI Key:  UPOACYJBVPQWIC-AIZHSPNTSA-N

Molfile:  

     RDKit          2D

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   12.7475   -7.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2192   -7.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.4555  -13.3578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.1202  -10.5655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   10.5307  -11.6939    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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   11.9961   -7.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2378   -8.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7530   -8.6171    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2797  -10.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7516   -8.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3033  -12.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2488   -7.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3999  -11.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9345  -10.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7509   -7.9249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 22 28  2  0
  1 12  2  0
  8 20  1  0
  7 21  2  0
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  9  3  1  0
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  4  7  1  0
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 27  9  1  0
 15  5  2  0
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 25  5  1  0
 24 31  1  0
M  CHG  2  24   1  31  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3402425

   (2S,5'R)-2'-benzylsulfinyl-7-chloro-4,6-dimethoxy-5'-methylspiro[1-benzofuran-2,4'-cyclohex-2-ene]-1',3-dione

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: 460.94

Molecular Weight (Monoisotopic): 460.0747

AlogP: 4.11

#Rotatable Bonds: 5

Polar Surface Area: 84.89

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.13

CX LogD: 3.13

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.62

Np Likeness Score: 0.85

References

1. Liéby-Muller F, Heudré Le Baliner Q, Grisoni S, Fournier E, Guilbaud N, Marion F..  (2015)  Synthesis and activities towards resistant cancer cells of sulfone and sulfoxide griseofulvin derivatives.,  25  (10): [PMID:25872984] [10.1016/j.bmcl.2015.03.081]

Source

Source(1):

• Scientific Literature