(S)-(-)-9-(4-aminopiperazin-1-yl)-8-fluoro-3-methyl-6-oxo-2,3-dihydro-6H-1-oxa-3a-azaphenalene-5-carboxylic acid

ID: ALA1215659

Cas Number: 1152314-49-2

PubChem CID: 46829291

Max Phase: Preclinical

Molecular Formula: C17H19FN4O4

Molecular Weight: 362.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1COc2c(N3CCN(N)CC3)c(F)cc3c(=O)c(C(=O)O)cn1c23

Standard InChI:  InChI=1S/C17H19FN4O4/c1-9-8-26-16-13-10(15(23)11(17(24)25)7-22(9)13)6-12(18)14(16)20-2-4-21(19)5-3-20/h6-7,9H,2-5,8,19H2,1H3,(H,24,25)/t9-/m0/s1

Standard InChI Key:  ICQVSZFWVUBYSI-VIFPVBQESA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    2.0750   -3.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583   -2.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458   -3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -2.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -2.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -4.0333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0708   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6458   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -3.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -1.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167   -4.0333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0750   -4.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -0.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -4.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -2.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -4.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5000   -4.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2167   -3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5083   -0.7292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -1.5542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9333   -4.4458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -1.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -4.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  1  1  0
  4  3  1  0
  5  3  2  0
  6  1  1  0
  7  5  1  0
  8  4  2  0
  9  4  1  0
 10 11  2  0
 11  5  1  0
 12  8  1  0
 13  2  1  0
 14 20  1  0
 15  1  1  0
 16  7  2  0
 17 15  1  0
 18 12  1  0
 19 12  1  0
 20 19  1  0
 21 18  1  0
 22 13  2  0
 23 10  1  0
 24 14  1  0
 25 13  1  0
 15 26  1  1
 17  9  1  0
  7  2  1  0
  8 10  1  0
 14 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1215659

   CID 46829291

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: 362.36

Molecular Weight (Monoisotopic): 362.1390

AlogP: 0.79

#Rotatable Bonds: 2

Polar Surface Area: 101.03

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.12

CX Basic pKa: 5.73

CX LogP: -0.24

CX LogD: -1.51

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: -0.14

References

1. Rossi F, Valentina C, Garavaglia S, Sathyasaikumar KV, Schwarcz R, Kojima S, Okuwaki K, Ono S, Kajii Y, Rizzi M..  (2010)  Crystal structure-based selective targeting of the pyridoxal 5'-phosphate dependent enzyme kynurenine aminotransferase II for cognitive enhancement.,  53  (15): [PMID:20684605] [10.1021/jm100464k]

2. Dounay AB, Tuttle JB, Verhoest PR..  (2015)  Challenges and Opportunities in the Discovery of New Therapeutics Targeting the Kynurenine Pathway.,  58  (22): [PMID:26207924] [10.1021/acs.jmedchem.5b00461]

Source

Source(1):

• Scientific Literature