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

ID: ALA3402426

PubChem CID: 72737651

Max Phase: Preclinical

Molecular Formula: C22H19ClO6S

Molecular Weight: 446.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(OC)c2c(c1Cl)O[C@@]1(C=C([S+]([O-])c3ccccc3)C(=O)C[C@H]1C)C2=O

Standard InChI:  InChI=1S/C22H19ClO6S/c1-12-9-14(24)17(30(26)13-7-5-4-6-8-13)11-22(12)21(25)18-15(27-2)10-16(28-3)19(23)20(18)29-22/h4-8,10-12H,9H2,1-3H3/t12-,22-,30?/m1/s1

Standard InChI Key:  PYRLFNHMKOKIBV-BYGLIRNBSA-N

Molfile:  

     RDKit          2D

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   10.5052   -9.0480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1620  -11.1590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5237   -9.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5317  -11.6979    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    8.3014  -12.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3981  -11.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9308  -10.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7509   -7.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2550   -8.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0060   -9.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0072   -9.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2575  -10.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5065   -9.9144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6 17  1  0
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 21 10  1  6
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  8 26  2  0
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M  CHG  2  20   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3402426

   (2S,5'R)-2'-(benzenesulfinyl)-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: 446.91

Molecular Weight (Monoisotopic): 446.0591

AlogP: 3.97

#Rotatable Bonds: 4

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: 3.36

CX LogD: 3.36

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: 0.90

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