3a-methyl-7-oxo-2,3,3a,4,7,10-hexahydro-1H-5-oxa-10,11,11btriazacyclopenta[a]anthracene-8-carboxylic acid

ID: ALA214187

PubChem CID: 11843817

Max Phase: Preclinical

Molecular Formula: C15H15N3O4

Molecular Weight: 301.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12CCCN1c1nc3ncc(C(=O)O)c(O)c3cc1OC2

Standard InChI:  InChI=1S/C15H15N3O4/c1-15-3-2-4-18(15)13-10(22-7-15)5-8-11(19)9(14(20)21)6-16-12(8)17-13/h5-6H,2-4,7H2,1H3,(H,20,21)(H,16,17,19)

Standard InChI Key:  CRMGLPGLCIILNS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   -2.4269  -20.5685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4287  -18.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7165  -19.3385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7131  -20.1637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971  -20.5690    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2799  -20.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833  -19.3327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0039  -18.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272  -18.9219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1398  -19.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4247  -18.1089    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0085  -18.1098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1385  -20.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1389  -19.3466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8446  -18.9438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5544  -19.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8403  -20.5713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5591  -20.1632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1695  -20.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8278  -21.4735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0064  -21.3811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2763  -19.7487    0.0000 C   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
 16 18  1  0
 17 18  1  0
  5  6  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 21  1  0
 21 17  1  0
 18 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA214187

   15-Methyl-4-oxo-17-oxa-7,9,11-triazatetracyclo[8.7.0.03,8.011,15]heptadeca-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: 301.30

Molecular Weight (Monoisotopic): 301.1063

AlogP: 1.78

#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: 0.68

CX LogP: 2.36

CX LogD: -1.03

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: 0.17

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