6-Hydroxy-2-(1-hydroxy-1-methyl-ethyl)-9-methyl-3,9-dihydro-2H-furo[2,3-b]quinolin-4-one

ID: ALA25275

Cas Number: 6872-52-2

PubChem CID: 336321

Max Phase: Preclinical

Molecular Formula: C15H17NO4

Molecular Weight: 275.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1c2c(c(=O)c3cc(O)ccc31)CC(C(C)(C)O)O2

Standard InChI:  InChI=1S/C15H17NO4/c1-15(2,19)12-7-10-13(18)9-6-8(17)4-5-11(9)16(3)14(10)20-12/h4-6,12,17,19H,7H2,1-3H3

Standard InChI Key:  ONPUKGULNMQBLF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
   -0.2208   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2208   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -1.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458    0.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -1.1667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8292   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8417   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7958    0.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7583    0.6458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7458   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -0.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3083   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -1.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8333    0.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -0.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -1.7625    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  7  2  0
 11  5  2  0
 12  9  1  0
 13  4  2  0
 14  3  1  0
 15 16  2  0
 16 10  1  0
 17 12  1  0
 18 15  1  0
 19 12  1  0
 20 12  1  0
  9  8  1  0
  4  5  1  0
 15 11  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA25275

   Ribaline

Molecule Features

Natural Product: Yes

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: 275.30

Molecular Weight (Monoisotopic): 275.1158

AlogP: 1.32

#Rotatable Bonds: 1

Polar Surface Area: 71.69

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.73

CX Basic pKa: ┄

CX LogP: 1.72

CX LogD: 1.72

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.82

Np Likeness Score: 1.86

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