3-Hydroxy-6-methoxy-2,2,9-trimethyl-2,3,4,9-tetrahydro-1-oxa-9-aza-anthracen-10-one

ID: ALA277490

PubChem CID: 44458030

Max Phase: Preclinical

Molecular Formula: C16H19NO4

Molecular Weight: 289.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)c(=O)c1c(n2C)OC(C)(C)C(O)C1

Standard InChI:  InChI=1S/C16H19NO4/c1-16(2)13(18)8-11-14(19)10-7-9(20-4)5-6-12(10)17(3)15(11)21-16/h5-7,13,18H,8H2,1-4H3

Standard InChI Key:  ZSSWMTCWRIQOKV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    0.3417   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3417    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -0.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833    0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083    0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -0.7167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7083   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208   -0.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208    0.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833    1.0958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1833   -1.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458    0.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7458   -0.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042    0.5000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3917   -1.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2583    0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7833    0.1958    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  7  1  0
  6  1  1  0
  7  3  1  0
  8  2  1  0
  9  6  1  0
 10  9  1  0
 11  7  2  0
 12  5  2  0
 13  4  2  0
 14  3  1  0
 15 16  2  0
 16 11  1  0
 17 10  1  0
 18  9  1  0
 19  9  1  0
 20 15  1  0
 21 20  1  0
  8 10  1  0
  4  5  1  0
 15 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA277490

   3-Hydroxy-7-methoxy-2,2,10-trimethyl-3,4-dihydropyrano[2,3-b]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: 289.33

Molecular Weight (Monoisotopic): 289.1314

AlogP: 1.62

#Rotatable Bonds: 1

Polar Surface Area: 60.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.89

CX Basic pKa: ┄

CX LogP: 1.87

CX LogD: 1.87

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.87

Np Likeness Score: 1.47

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