9-oxo-3,4,6,9-tetrahydro-2H-[1,4]oxazino[3,2-b][1,8]naphthyridine-8-carboxylic acid

ID: ALA209810

PubChem CID: 11844476

Max Phase: Preclinical

Molecular Formula: C11H9N3O4

Molecular Weight: 247.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2nc3c(cc2c1O)OCCN3

Standard InChI:  InChI=1S/C11H9N3O4/c15-8-5-3-7-10(12-1-2-18-7)14-9(5)13-4-6(8)11(16)17/h3-4H,1-2H2,(H,16,17)(H2,12,13,14,15)

Standard InChI Key:  KAKZIGZOPHZURN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 20  0  0  0  0  0  0  0  0999 V2000
   13.9520  -22.0945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9502  -20.4527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6661  -20.8580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6695  -21.6876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3893  -22.0950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1102  -21.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1067  -20.8521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3824  -20.4400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8211  -20.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5373  -20.8455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8185  -19.6219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3779  -19.6228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2367  -21.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2363  -20.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5268  -20.4612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8133  -20.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5336  -22.0949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8085  -21.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
 13  1  2  0
  1  4  1  0
  9 10  1  0
  9 11  2  0
  7  9  1  0
  3  2  1  0
  8 12  1  0
 13 14  1  0
  2 14  2  0
  3  4  1  0
  3  8  2  0
  4  5  2  0
 13 17  1  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 17 18  1  0
  5  6  1  0
  6  7  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA209810

   9-Oxo-2,3,4,6-tetrahydro-[1,4]oxazino[3,2-b][1,8]naphthyridine-8-carboxylic acid

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: 247.21

Molecular Weight (Monoisotopic): 247.0593

AlogP: 0.84

#Rotatable Bonds: 1

Polar Surface Area: 104.57

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.45

CX Basic pKa: 0.93

CX LogP: 0.98

CX LogD: -2.41

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.69

Np Likeness Score: -0.07

References

1. Hinman MM, Rosenberg TA, Balli D, Black-Schaefer C, Chovan LE, Kalvin D, Merta PJ, Nilius AM, Pratt SD, Soni NB, Wagenaar FL, Weitzberg M, Wagner R, Beutel BA..  (2006)  Novel antibacterial class: a series of tetracyclic derivatives.,  49  (16): [PMID:16884296] [10.1021/jm060010w]

Source

Source(1):

• Scientific Literature