N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)benzo[d][1,3]dioxole-5-carboxamide

ID: ALA454166

PubChem CID: 44564182

Max Phase: Preclinical

Molecular Formula: C20H18N2O5

Molecular Weight: 366.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](NC(=O)c2ccc3c(c2)OCO3)[C@@H]1O

Standard InChI:  InChI=1S/C20H18N2O5/c1-20(2)18(23)17(13-7-11(9-21)3-5-14(13)27-20)22-19(24)12-4-6-15-16(8-12)26-10-25-15/h3-8,17-18,23H,10H2,1-2H3,(H,22,24)/t17-,18+/m1/s1

Standard InChI Key:  LCMULRGEZDKTHJ-MSOLQXFVSA-N

Molfile:  

     RDKit          2D

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    1.7372    0.7660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227    1.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4517    2.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4517    1.1785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372    2.4160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227    2.0035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096    2.5556    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7452    3.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5657    3.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207   -1.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1207   -2.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062   -2.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4062   -1.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3082   -1.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3082   -2.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227   -2.9465    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -2.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -1.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227   -1.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0193   -3.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5496   -2.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8352   -1.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496   -0.8840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7372   -0.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4517   -0.4715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0227   -0.4715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4517   -1.2965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
 12 15  2  0
 10 11  2  0
 14 13  2  0
 22 23  3  0
 10 22  1  0
 13 10  1  0
 14 19  1  0
 15 16  1  0
 24 25  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14 15  1  0
 17 20  1  0
 17 21  1  0
 11 12  1  0
 24  1  1  0
 19 26  1  1
 24 26  1  0
 18 27  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA454166

   N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)benzo[d][1,3]dioxole-5-carboxamide

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: 366.37

Molecular Weight (Monoisotopic): 366.1216

AlogP: 2.29

#Rotatable Bonds: 2

Polar Surface Area: 100.81

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.38

CX Basic pKa: ┄

CX LogP: 2.05

CX LogD: 2.05

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.85

Np Likeness Score: 0.06

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