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

ID: ALA517128

PubChem CID: 44564206

Max Phase: Preclinical

Molecular Formula: C21H19N3O2

Molecular Weight: 345.40

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H19N3O2/c1-21(2)19(25)18(16-12-14(13-22)8-9-17(16)26-21)24-11-10-23-20(24)15-6-4-3-5-7-15/h3-12,18-19,25H,1-2H3/t18-,19+/m1/s1

Standard InChI Key:  AHBKXQFEGKICII-MOPGFXCFSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    6.0549   -6.1189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0538   -6.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7689   -7.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7671   -5.7060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4828   -6.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4816   -6.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1987   -7.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9216   -6.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9228   -6.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2011   -5.6973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3284   -7.6611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6327   -6.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6385   -5.7064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2011   -4.8720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3407   -5.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6259   -5.2944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8672   -4.3890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6122   -3.6040    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7869   -3.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5319   -4.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6911   -4.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1046   -5.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9277   -5.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3371   -4.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9171   -3.6651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0954   -3.6724    0.0000 C   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
 14 17  1  0
  4  1  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
  8  9  1  0
 17 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 25  1  0
  8 12  1  0
 25 26  2  0
 26 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA517128

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

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: 345.40

Molecular Weight (Monoisotopic): 345.1477

AlogP: 3.54

#Rotatable Bonds: 2

Polar Surface Area: 71.07

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: 5.76

CX LogP: 3.48

CX LogD: 3.47

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.77

Np Likeness Score: -0.20

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