(3S,4R)-4-(6-chloro-3-oxo-3H-benzo[d]isoxazol-2-yl)-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

ID: ALA473744

PubChem CID: 42609940

Product Number: S608693, Order Now?

Max Phase: Preclinical

Molecular Formula: C19H15ClN2O4

Molecular Weight: 370.79

Molecule Type: Small molecule

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Associated Items:

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](n2oc3cc(Cl)ccc3c2=O)[C@@H]1O

Standard InChI:  InChI=1S/C19H15ClN2O4/c1-19(2)17(23)16(13-7-10(9-21)3-6-14(13)25-19)22-18(24)12-5-4-11(20)8-15(12)26-22/h3-8,16-17,23H,1-2H3/t16-,17+/m1/s1

Standard InChI Key:  LSWVRWFSRJQEKB-SJORKVTESA-N

Molfile:  

     RDKit          2D

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   -3.0123   -2.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972   -2.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2990   -0.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -1.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5845   -2.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8672   -2.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1443   -2.0658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1431   -1.2323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8648   -0.8123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2626   -2.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670   -1.6466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728   -0.8214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8648    0.0131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7256   -0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4404   -0.4093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1987    0.4962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5341    0.4962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5862    0.2408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    1.2812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4541    1.2779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0405    1.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4508    2.7052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2791    2.7045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    1.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6926    3.4188    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
  1  2  2  0
  5  4  2  0
 15 16  3  0
  1 15  1  0
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  5 10  1  0
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 20 18  1  0
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  6  7  1  0
 17 19  2  0
  7  8  1  0
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  5  6  1  0
 22 23  2  0
  8 11  1  0
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 25 20  1  0
  8 12  1  0
 24 26  1  0
M  END

Associated Targets(Human)

ABCC9 Tclin Sulfonylurea receptor 2 (109 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rattus norvegicus (775804 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 370.79Molecular Weight (Monoisotopic): 370.0720AlogP: 3.24#Rotatable Bonds: 1
Polar Surface Area: 88.39Molecular Species: NEUTRALHBA: 6HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 13.17CX Basic pKa: CX LogP: 3.09CX LogD: 3.09
Aromatic Rings: 3Heavy Atoms: 26QED Weighted: 0.71Np Likeness Score: -0.03

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