6-Oxo-1,2,(S)-2a,3,6,9-hexahydro-4-oxa-9,10,10b-triazacyclobuta[a]anthracene-7-carboxylic acid

ID: ALA211321

PubChem CID: 11844086

Max Phase: Preclinical

Molecular Formula: C13H11N3O4

Molecular Weight: 273.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cnc2nc3c(cc2c1O)OC[C@@H]1CCN31

Standard InChI:  InChI=1S/C13H11N3O4/c17-10-7-3-9-12(16-2-1-6(16)5-20-9)15-11(7)14-4-8(10)13(18)19/h3-4,6H,1-2,5H2,(H,18,19)(H,14,15,17)/t6-/m0/s1

Standard InChI Key:  UIKNYHFGGWGPNP-LURJTMIESA-N

Molfile:  

     RDKit          2D

 21 24  0  0  1  0  0  0  0  0999 V2000
    6.0060  -17.3685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042  -15.7308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7184  -16.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7218  -16.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4397  -17.3690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1589  -16.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1554  -16.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4329  -15.7182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8680  -15.7173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5824  -16.1227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8654  -14.9021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4284  -14.9030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2925  -16.9605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2921  -16.1432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5844  -15.7393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8726  -16.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5898  -17.3704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8678  -16.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4595  -17.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1814  -18.0923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9015  -16.7047    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  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
 18 16  1  0
  5  6  1  0
 17 18  1  0
  6  7  2  0
  7  8  1  0
 13  1  2  0
  1  4  1  0
 18 19  1  0
 19 20  1  0
 20 17  1  0
 18 21  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA211321

   (14S)-4-oxo-16-oxa-7,9,11-triazatetracyclo[8.6.0.03,8.011,14]hexadeca-1(10),2,5,8-tetraene-5-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: 273.25

Molecular Weight (Monoisotopic): 273.0750

AlogP: 1.00

#Rotatable Bonds: 1

Polar Surface Area: 95.78

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.45

CX Basic pKa: 0.71

CX LogP: 1.56

CX LogD: -1.83

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.80

Np Likeness Score: -0.15

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