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

ID: ALA278127

PubChem CID: 10612349

Max Phase: Preclinical

Molecular Formula: C14H14N2O4

Molecular Weight: 274.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)CCc2c(O)nc3ccc([N+](=O)[O-])cc3c2O1

Standard InChI:  InChI=1S/C14H14N2O4/c1-14(2)6-5-9-12(20-14)10-7-8(16(18)19)3-4-11(10)15-13(9)17/h3-4,7H,5-6H2,1-2H3,(H,15,17)

Standard InChI Key:  UEZMJQINPFIZMM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    0.8917   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -1.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8917   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3667   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875   -0.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500   -1.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -1.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -0.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -1.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -2.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1500   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9417   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -0.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  2  0
  5 10  1  0
  6  7  2  0
  7  3  1  0
  8  1  1  0
  9  3  1  0
 10  9  2  0
 11  2  1  0
 12  5  1  0
 13  8  1  0
 14  5  2  0
 15  4  1  0
 16  7  1  0
 17 10  1  0
 18 13  1  0
 19 13  1  0
 20 13  1  0
 11 18  1  0
  4  6  1  0
 16 17  2  0
M  CHG  2   5   1  12  -1
M  END

Alternative Forms

1. Parent:

   

   ALA278127

   2,2-dimethyl-9-nitro-4,6-dihydro-3H-pyrano[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: 274.28

Molecular Weight (Monoisotopic): 274.0954

AlogP: 2.95

#Rotatable Bonds: 1

Polar Surface Area: 85.49

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.11

CX Basic pKa: 2.75

CX LogP: 3.39

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.64

Np Likeness Score: -0.26

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