3,4-dichloro-N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)benzamide

ID: ALA508490

PubChem CID: 44564183

Max Phase: Preclinical

Molecular Formula: C19H16Cl2N2O3

Molecular Weight: 391.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)c2ccc(Cl)c(Cl)c2)[C@@H]1O

Standard InChI:  InChI=1S/C19H16Cl2N2O3/c1-19(2)17(24)16(12-7-10(9-22)3-6-15(12)26-19)23-18(25)11-4-5-13(20)14(21)8-11/h3-8,16-17,24H,1-2H3,(H,23,25)/t16-,17+/m1/s1

Standard InChI Key:  ZPTXVIWXGDGGTD-SJORKVTESA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   12.4239    0.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4293    0.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7157    1.3887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0002    0.9762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0028    0.1469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7170   -0.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2852    1.3878    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.7161    2.2137    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.2861   -2.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2849   -3.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9998   -3.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9980   -2.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7133   -2.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7121   -3.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4290   -3.9905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1517   -3.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1529   -2.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4314   -2.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5584   -4.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8625   -3.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8684   -2.3335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4315   -1.4994    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5721   -2.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8575   -1.9216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.7170   -1.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0025   -1.4993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  3  8  1  0
 17 21  1  6
 11 14  2  0
 18 22  1  1
  9 10  2  0
 13 12  2  0
 23 24  3  0
  9 23  1  0
 12  9  1  0
 22 25  1  0
 13 18  1  0
 25  6  1  0
 14 15  1  0
 25 26  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 14  1  0
 16 19  1  0
 16 20  1  0
 10 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA508490

   3,4-dichloro-N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)benzamide

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: 391.25

Molecular Weight (Monoisotopic): 390.0538

AlogP: 3.87

#Rotatable Bonds: 2

Polar Surface Area: 82.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.11

CX Basic pKa: ┄

CX LogP: 3.63

CX LogD: 3.63

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.81

Np Likeness Score: -0.35

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