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

ID: ALA3402427

PubChem CID: 73053109

Max Phase: Preclinical

Molecular Formula: C23H21ClO7S

Molecular Weight: 476.93

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H21ClO7S/c1-13-9-15(25)18(32(27,28)12-14-7-5-4-6-8-14)11-23(13)22(26)19-16(29-2)10-17(30-3)20(24)21(19)31-23/h4-8,10-11,13H,9,12H2,1-3H3/t13-,23-/m1/s1

Standard InChI Key:  ALQDFQMVFVAENH-JCQPUDPBSA-N

Molfile:  

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    5.6837    1.1248    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6034    1.8957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9742   -0.2216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.5325    0.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.9613    0.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2612   -2.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6597   -2.9324    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6743    2.7497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7221    3.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2709   -1.7002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3024   -1.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0938    0.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2445    1.5745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6546    1.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8027    2.0282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5408    3.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1307    4.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9826    3.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 17  1  1
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  7 19  2  0
  5 20  1  1
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  8  2  1  0
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 31 32  2  0
 32 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3402427

   (2S,5'R)-2'-benzylsulfonyl-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: 476.93

Molecular Weight (Monoisotopic): 476.0697

AlogP: 3.78

#Rotatable Bonds: 5

Polar Surface Area: 95.97

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.65

Np Likeness Score: 0.47

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