(3S,4R)-4-(1,3-Dioxo-1,3-dihydro-pyrrolo[3,4-c]pyridin-2-yl)-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

ID: ALA521608

PubChem CID: 44564513

Max Phase: Preclinical

Molecular Formula: C19H15N3O4

Molecular Weight: 349.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@@H](N2C(=O)c3ccncc3C2=O)[C@@H]1O

Standard InChI:  InChI=1S/C19H15N3O4/c1-19(2)16(23)15(12-7-10(8-20)3-4-14(12)26-19)22-17(24)11-5-6-21-9-13(11)18(22)25/h3-7,9,15-16,23H,1-2H3/t15-,16+/m1/s1

Standard InChI Key:  SDPXDXXATHVSGC-CVEARBPZSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    3.5123  -11.1039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5111  -11.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2262  -12.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244  -10.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9401  -11.1002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9389  -11.9336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6560  -12.3491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3790  -11.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3802  -11.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6584  -10.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7857  -12.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0900  -11.5166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0958  -10.6914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6584   -9.8570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3245   -9.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9893   -9.3739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1093   -9.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2442   -8.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0692   -8.5924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4826   -7.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0724   -7.1652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2443   -7.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8344   -7.8782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2047   -9.6302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7981  -10.6919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0832  -10.2795    0.0000 N   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
 14 15  1  0
  1  2  2  0
  5  4  2  0
 15 19  1  0
 18 16  1  0
 16 14  1  0
  4  1  1  0
 15 17  2  0
  5 10  1  0
  6  7  1  0
 18 19  2  0
  7  8  1  0
 19 20  1  0
  8  9  1  0
 20 21  2  0
  9 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 23 18  1  0
  8 11  1  0
 16 24  2  0
  8 12  1  0
 25 26  3  0
  1 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA521608

   (3S,4R)-4-(1,3-Dioxo-1,3-dihydro-pyrrolo[3,4-c]pyridin-2-yl)-3-hydroxy-2,2-dimethyl-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: 349.35

Molecular Weight (Monoisotopic): 349.1063

AlogP: 1.82

#Rotatable Bonds: 1

Polar Surface Area: 103.52

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.23

CX Basic pKa: 1.86

CX LogP: 1.08

CX LogD: 1.08

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.79

Np Likeness Score: -0.02

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