(3S,4R)-6,7-Dichloro-4-(5-chloro-benzo[d]isoxazol-3-ylamino)-2,2-dimethyl-chroman-3-ol

ID: ALA473132

PubChem CID: 44564347

Max Phase: Preclinical

Molecular Formula: C18H15Cl3N2O3

Molecular Weight: 413.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2cc(Cl)c(Cl)cc2[C@@H](Nc2noc3ccc(Cl)cc23)[C@@H]1O

Standard InChI:  InChI=1S/C18H15Cl3N2O3/c1-18(2)16(24)15(9-6-11(20)12(21)7-14(9)25-18)22-17-10-5-8(19)3-4-13(10)26-23-17/h3-7,15-16,24H,1-2H3,(H,22,23)/t15-,16+/m1/s1

Standard InChI Key:  PTGNZWJRQOTYKB-CVEARBPZSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    6.7209   -6.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7197   -7.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -7.8241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4329   -6.1707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1485   -6.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1473   -7.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8643   -7.8285    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5872   -7.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5884   -6.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8667   -6.1620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9939   -8.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2982   -6.9962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3040   -6.1711    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8603   -5.3339    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5320   -4.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3140   -5.1165    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8046   -4.4530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5383   -4.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3250   -3.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5020   -2.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8934   -2.4216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1049   -2.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9315   -3.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0061   -6.1711    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0047   -7.8231    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.4938   -2.1202    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
 14 15  1  0
 15 16  2  0
  5  4  2  0
  4  1  1  0
 16 17  1  0
 17 19  1  0
 18 15  1  0
  5 10  1  0
  6  7  1  0
 18 19  2  0
  7  8  1  0
 19 20  1  0
  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:

   

   ALA473132

   (3S,4R)-6,7-Dichloro-4-(5-chloro-benzo[d]isoxazol-3-ylamino)-2,2-dimethyl-chroman-3-ol

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: 413.69

Molecular Weight (Monoisotopic): 412.0148

AlogP: 5.47

#Rotatable Bonds: 2

Polar Surface Area: 67.52

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.89

CX Basic pKa: 0.64

CX LogP: 4.76

CX LogD: 4.76

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.58

Np Likeness Score: 0.04

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