(3S,4R)-6-Chloro-2,2-dimethyl-4-(2-phenyl-imidazol-1-yl)-chroman-3-ol

ID: ALA516976

PubChem CID: 44564249

Max Phase: Preclinical

Molecular Formula: C20H19ClN2O2

Molecular Weight: 354.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(Cl)cc2[C@@H](n2ccnc2-c2ccccc2)[C@@H]1O

Standard InChI:  InChI=1S/C20H19ClN2O2/c1-20(2)18(24)17(15-12-14(21)8-9-16(15)25-20)23-11-10-22-19(23)13-6-4-3-5-7-13/h3-12,17-18,24H,1-2H3/t17-,18+/m1/s1

Standard InChI Key:  YUWHIPMHJROMKH-MSOLQXFVSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   14.8527   -6.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8516   -7.6107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5664   -8.0235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5646   -6.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2800   -6.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2788   -7.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9957   -8.0280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7183   -7.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7195   -6.7817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9981   -6.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1250   -8.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4292   -7.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4350   -6.3710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9981   -5.5369    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6639   -5.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4090   -4.2694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.5840   -4.2694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3291   -5.0540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4875   -5.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9009   -5.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7237   -5.7599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1329   -5.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7131   -4.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8917   -4.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1382   -6.3710    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  8 12  1  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
  4  1  1  0
  5 10  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 14  1  0
  6  7  1  0
 15 19  1  0
  7  8  1  0
 19 20  2  0
  8  9  1  0
 20 21  1  0
  9 10  1  0
 21 22  2  0
  5  6  1  0
 22 23  1  0
  8 11  1  0
 23 24  2  0
 24 19  1  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA516976

   (3S,4R)-6-Chloro-2,2-dimethyl-4-(2-phenyl-imidazol-1-yl)-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: 354.84

Molecular Weight (Monoisotopic): 354.1135

AlogP: 4.32

#Rotatable Bonds: 2

Polar Surface Area: 47.28

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.18

CX Basic pKa: 5.76

CX LogP: 4.23

CX LogD: 4.22

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.74

Np Likeness Score: -0.09

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