(3S,4R)-4-(5-Chloro-benzo[d]isoxazol-3-ylamino)-3-hydroxy-2,2-dimethyl-chroman-6-sulfonic acid diethylamide

ID: ALA473750

PubChem CID: 44564324

Max Phase: Preclinical

Molecular Formula: C22H26ClN3O5S

Molecular Weight: 479.99

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)S(=O)(=O)c1ccc2c(c1)[C@@H](Nc1noc3ccc(Cl)cc13)[C@H](O)C(C)(C)O2

Standard InChI:  InChI=1S/C22H26ClN3O5S/c1-5-26(6-2)32(28,29)14-8-10-17-15(12-14)19(20(27)22(3,4)30-17)24-21-16-11-13(23)7-9-18(16)31-25-21/h7-12,19-20,27H,5-6H2,1-4H3,(H,24,25)/t19-,20+/m1/s1

Standard InChI Key:  BYWJSRQTESMLML-UXHICEINSA-N

Molfile:  

     RDKit          2D

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    3.6411  -10.2954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3321   -8.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6196   -9.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5375   -5.5293    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA473750

   (3S,4R)-4-(5-Chloro-benzo[d]isoxazol-3-ylamino)-3-hydroxy-2,2-dimethyl-chroman-6-sulfonic acid diethylamide

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: 479.99

Molecular Weight (Monoisotopic): 479.1282

AlogP: 4.20

#Rotatable Bonds: 6

Polar Surface Area: 104.90

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.88

CX Basic pKa: 0.64

CX LogP: 3.32

CX LogD: 3.32

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.55

Np Likeness Score: -0.77

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