N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)-P-methyl-P-phenylphosphinic amide

ID: ALA508720

PubChem CID: 44564186

Max Phase: Preclinical

Molecular Formula: C19H21N2O3P

Molecular Weight: 356.36

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C19H21N2O3P/c1-19(2)18(22)17(15-11-13(12-20)9-10-16(15)24-19)21-25(3,23)14-7-5-4-6-8-14/h4-11,17-18,22H,1-3H3,(H,21,23)/t17-,18+,25?/m1/s1

Standard InChI Key:  KUKOBIYRPWXHMP-GHTAMBSGSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   11.7292  -20.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7280  -21.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4424  -21.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4406  -20.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1556  -20.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1544  -21.2419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8708  -21.6570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5931  -21.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5943  -20.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8732  -19.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9995  -21.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3035  -20.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3093  -20.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8732  -19.1672    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.0156  -20.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3014  -19.5893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5873  -18.7551    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.2993  -18.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1700  -18.0440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0186  -18.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7302  -18.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7229  -17.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9981  -17.0915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2896  -17.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0029  -19.4672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 12  1  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
  4  1  1  0
 14 17  1  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
 17 19  2  0
  7  8  1  0
 18 20  2  0
  8  9  1  0
 20 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 18  1  0
 17 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA508720

   N-((3S,4R)-6-cyano-3-hydroxy-2,2-dimethylchroman-4-yl)-P-methyl-P-phenylphosphinic amide

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: 356.36

Molecular Weight (Monoisotopic): 356.1290

AlogP: 2.95

#Rotatable Bonds: 3

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: 13.05

CX Basic pKa: 2.92

CX LogP: 1.87

CX LogD: 1.87

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.83

Np Likeness Score: 0.24

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