(3S,4R)-6-Chloro-2-(6,7-dichloro-3-hydroxy-2,2-dimethyl-chroman-4-yl)-benzo[d]isoxazol-3-one

ID: ALA491674

PubChem CID: 44564424

Max Phase: Preclinical

Molecular Formula: C18H14Cl3NO4

Molecular Weight: 414.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2cc(Cl)c(Cl)cc2[C@@H](n2oc3cc(Cl)ccc3c2=O)[C@@H]1O

Standard InChI:  InChI=1S/C18H14Cl3NO4/c1-18(2)16(23)15(10-6-11(20)12(21)7-13(10)25-18)22-17(24)9-4-3-8(19)5-14(9)26-22/h3-7,15-16,23H,1-2H3/t15-,16+/m1/s1

Standard InChI Key:  DRUFGAQCTMUDIN-CVEARBPZSA-N

Molfile:  

     RDKit          2D

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   -2.9320  -25.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2171  -26.2714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2190  -24.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5035  -25.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5047  -25.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878  -26.2758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0650  -25.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638  -25.0295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7854  -24.6096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417  -26.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458  -25.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6518  -24.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7853  -23.7845    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1194  -23.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4543  -23.3016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6652  -23.5570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1995  -22.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3747  -22.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0387  -21.8088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3715  -21.0935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1994  -21.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6090  -21.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6455  -24.6187    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6469  -26.2704    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6128  -20.3802    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  9 13  1  6
  3  6  2  0
 10 14  1  1
 14 15  1  0
  1  2  2  0
  5  4  2  0
 15 19  1  0
 18 16  1  0
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  4  1  1  0
 15 17  2  0
  5 10  1  0
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 18 19  2  0
  7  8  1  0
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  8  9  1  0
 20 21  2  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
  8 11  1  0
  1 24  1  0
  2 25  1  0
  8 12  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA491674

   (3S,4R)-6-Chloro-2-(6,7-dichloro-3-hydroxy-2,2-dimethyl-chroman-4-yl)-benzo[d]isoxazol-3-one

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: 414.67

Molecular Weight (Monoisotopic): 412.9988

AlogP: 4.68

#Rotatable Bonds: 1

Polar Surface Area: 64.60

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: ┄

CX LogP: 4.44

CX LogD: 4.44

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.63

Np Likeness Score: 0.37

References

1. Zhang X, Qiu Y, Li X, Bhattacharjee S, Woods M, Kraft P, Lundeen SG, Sui Z..  (2009)  Discovery and structure-activity relationships of a novel series of benzopyran-based K(ATP) openers for urge urinary incontinence.,  17  (2): [PMID:19101153] [10.1016/j.bmc.2008.11.055]

Source

Source(1):

• Scientific Literature