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

ID: ALA211569

PubChem CID: 11843819

Max Phase: Preclinical

Molecular Formula: C17H17N3O4

Molecular Weight: 327.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CCC12CCCN1c1nc3ncc(C(=O)O)c(O)c3cc1OC2

Standard InChI:  InChI=1S/C17H17N3O4/c1-2-4-17-5-3-6-20(17)15-12(24-9-17)7-10-13(21)11(16(22)23)8-18-14(10)19-15/h2,7-8H,1,3-6,9H2,(H,22,23)(H,18,19,21)

Standard InChI Key:  FFLALTTUXXLXTP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
    1.1904   -6.0101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1886   -4.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9033   -4.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9068   -5.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6253   -6.0106    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3451   -5.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417   -4.7698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6185   -4.3583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0548   -4.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7700   -4.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0523   -3.5415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6140   -3.5424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4761   -5.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4757   -4.7838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2325   -4.3795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9450   -4.7845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282   -6.0129    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9497   -5.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5622   -6.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2193   -6.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -6.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6694   -5.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3835   -5.5991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0972   -5.1865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  9 10  1  0
  9 11  2  0
  7  9  1  0
 18 22  1  0
  3  2  1  0
 22 23  1  0
  8 12  1  0
 23 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA211569

   4-Oxo-15-prop-2-enyl-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: 327.34

Molecular Weight (Monoisotopic): 327.1219

AlogP: 2.34

#Rotatable Bonds: 3

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: 0.67

CX LogP: 3.02

CX LogD: -0.37

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.84

Np Likeness Score: 0.16

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