2-(1-Hydroxy-1-methyl-ethyl)-5-methyl-8-nitro-3,5-dihydro-2H-furo[3,2-c]quinolin-4-one

ID: ALA25442

PubChem CID: 10709609

Max Phase: Preclinical

Molecular Formula: C15H16N2O5

Molecular Weight: 304.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c(=O)c2c(c3cc([N+](=O)[O-])ccc31)OC(C(C)(C)O)C2

Standard InChI:  InChI=1S/C15H16N2O5/c1-15(2,19)12-7-10-13(22-12)9-6-8(17(20)21)4-5-11(9)16(3)14(10)18/h4-6,12,19H,7H2,1-3H3

Standard InChI Key:  XMZGXJCFVCWZHQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.2542   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -0.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2542   -1.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -1.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -2.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -0.3542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -0.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7042   -0.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4542   -0.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -0.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -1.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -2.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3583   -0.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -2.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8708   -1.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -1.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4417    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3292    0.3875    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  2  1  0
  7  5  1  0
  8 12  1  0
  9  1  1  0
 10  9  1  0
 11  4  2  0
 12 11  1  0
 13  7  2  0
 14 10  1  0
 15  8  1  0
 16  3  2  0
 17  8  2  0
 18 13  1  0
 19  5  1  0
 20 14  1  0
 21 14  1  0
 22 14  1  0
 10  6  1  0
  4  7  1  0
 12 18  2  0
M  CHG  2   8   1  15  -1
M  END

Alternative Forms

1. Parent:

   

   ALA25442

   2-(2-Hydroxypropan-2-yl)-5-methyl-8-nitro-2,3-dihydrofuro[3,2-c]quinolin-4-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: 304.30

Molecular Weight (Monoisotopic): 304.1059

AlogP: 1.52

#Rotatable Bonds: 2

Polar Surface Area: 94.60

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.75

CX LogD: 0.75

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.67

Np Likeness Score: 0.66

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