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

ID: ALA461800

PubChem CID: 44564205

Max Phase: Preclinical

Molecular Formula: C22H21N3O2

Molecular Weight: 359.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cn([C@@H]2c3cc(C#N)ccc3OC(C)(C)[C@H]2O)c(-c2ccccc2)n1

Standard InChI:  InChI=1S/C22H21N3O2/c1-14-13-25(21(24-14)16-7-5-4-6-8-16)19-17-11-15(12-23)9-10-18(17)27-22(2,3)20(19)26/h4-11,13,19-20,26H,1-3H3/t19-,20+/m1/s1

Standard InChI Key:  YMPLHFGZNFZQLU-UXHICEINSA-N

Molfile:  

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   -2.9689   -6.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2536   -6.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2548   -7.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5378   -8.0619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1042   -7.2298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0983   -6.4048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5353   -5.5706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3949   -6.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1096   -5.9930    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8695   -5.0878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0458   -5.0837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3676   -5.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1905   -5.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5996   -5.0778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1799   -4.3641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3584   -4.3713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4345   -3.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
 10 14  1  1
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  2  3  1  0
  9 13  1  6
 19 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA461800

   (3S,4R)-3-Hydroxy-2,2-dimethyl-4-(4-methyl-2-phenylimidazol-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: 359.43

Molecular Weight (Monoisotopic): 359.1634

AlogP: 3.85

#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: 5.63

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -0.26

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