2,2,6-Trimethyl-9-nitro-2,3,4,6-tetrahydro-pyrano[3,2-c]quinolin-5-one

ID: ALA25489

PubChem CID: 10637073

Max Phase: Preclinical

Molecular Formula: C15H16N2O4

Molecular Weight: 288.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(c3cc([N+](=O)[O-])ccc31)OC(C)(C)CC2

Standard InChI:  InChI=1S/C15H16N2O4/c1-15(2)7-6-10-13(21-15)11-8-9(17(19)20)4-5-12(11)16(3)14(10)18/h4-5,8H,6-7H2,1-3H3

Standard InChI Key:  VVVXFFQYFOXXOR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    0.4167   -0.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -0.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -0.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -1.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6333   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -0.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1125    0.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500   -0.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417   -0.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833    0.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4167    0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9375   -1.2542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7083   -0.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9417    0.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8375    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083    1.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  5  1  0
  7 10  1  0
  8  2  1  0
  9  4  2  0
 10  9  1  0
 11  1  1  0
 12  6  2  0
 13  7  1  0
 14 18  1  0
 15  3  2  0
 16  7  2  0
 17 12  1  0
 18 11  1  0
 19  5  1  0
 20 14  1  0
 21 14  1  0
  8 14  1  0
  4  6  1  0
 10 17  2  0
M  CHG  2   7   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA25489

   2,2,6-Trimethyl-9-nitro-3,4-dihydropyrano[3,2-c]quinolin-5-one

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: 288.30

Molecular Weight (Monoisotopic): 288.1110

AlogP: 2.55

#Rotatable Bonds: 1

Polar Surface Area: 74.37

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.82

CX LogD: 1.82

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.60

Np Likeness Score: -0.02

References

1. Butenschön I, Möller K, Hänsel W..  (2001)  Angular methoxy-substituted furo- and pyranoquinolinones as blockers of the voltage-gated potassium channel Kv1.3.,  44  (8): [PMID:11312924] [10.1021/jm001007u]

Source

Source(1):

• Scientific Literature