5-methyl-7-oxo-1,2,3,3a,4,5,7,10-octahydro-5,10,11,11b-tetraazacyclopenta[a]anthracene-8-carboxylic acid

ID: ALA213450

PubChem CID: 11843950

Max Phase: Preclinical

Molecular Formula: C15H16N4O3

Molecular Weight: 300.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1C[C@@H]2CCCN2c2nc3ncc(C(=O)O)c(O)c3cc21

Standard InChI:  InChI=1S/C15H16N4O3/c1-18-7-8-3-2-4-19(8)14-11(18)5-9-12(20)10(15(21)22)6-16-13(9)17-14/h5-6,8H,2-4,7H2,1H3,(H,21,22)(H,16,17,20)/t8-/m0/s1

Standard InChI Key:  NABODKQCZVJUAC-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  1  0  0  0  0  0999 V2000
   -1.5350  -25.9029    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5368  -24.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247  -24.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8212  -25.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1053  -25.9034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118  -25.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085  -24.6670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1121  -24.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3190  -24.2562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0316  -24.6605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3165  -23.4432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166  -23.4442    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2467  -25.4961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471  -24.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9527  -24.2781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6626  -24.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9484  -25.9057    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6673  -25.4976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2776  -26.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9359  -26.8079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1146  -26.7154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9520  -23.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5811  -25.0915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  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
 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
  9 10  1  0
 15 22  1  0
 18 23  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA213450

   (15S)-17-methyl-4-oxo-7,9,11,17-tetrazatetracyclo[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: 300.32

Molecular Weight (Monoisotopic): 300.1222

AlogP: 1.45

#Rotatable Bonds: 1

Polar Surface Area: 89.79

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: 0.10

CX LogP: 2.35

CX LogD: -1.04

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.82

Np Likeness Score: -0.42

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