(3S,12aS)-3-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]-indole-1,4-dion

ID: ALA229494

PubChem CID: 21604533

Max Phase: Preclinical

Molecular Formula: C15H15N3O2

Molecular Weight: 269.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1NC(=O)[C@@H]2Cc3c([nH]c4ccccc34)CN2C1=O

Standard InChI:  InChI=1S/C15H15N3O2/c1-8-15(20)18-7-12-10(6-13(18)14(19)16-8)9-4-2-3-5-11(9)17-12/h2-5,8,13,17H,6-7H2,1H3,(H,16,19)/t8-,13-/m0/s1

Standard InChI Key:  YBFSNSRKOIYLIT-SDBXPKJASA-N

Molfile:  

     RDKit          2D

 21 24  0  0  1  0  0  0  0  0999 V2000
   -3.6121    1.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0985    0.8172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7650    0.0683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924    1.3988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    0.6431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9508   -0.0229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4678   -0.6919    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801    0.3858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6818   -0.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9686   -0.8568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9653    0.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2476    0.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2531   -0.4495    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4610   -0.8682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1854   -0.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1909    0.3734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4720    0.7967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    1.6207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4546   -1.6922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2539    1.2110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8956   -0.8766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
  8 11  1  0
  9 10  1  0
 10 13  1  0
 12 11  1  0
 12 13  1  0
  1  2  1  0
  1  4  2  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  8  9  2  0
 17 18  2  0
  2  3  2  0
 14 19  2  0
  3  6  1  0
 12 20  1  6
  5  4  1  0
 15 21  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA229494

   (5S,8S)-5-methyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione

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: 269.30

Molecular Weight (Monoisotopic): 269.1164

AlogP: 0.94

#Rotatable Bonds: ┄

Polar Surface Area: 65.20

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.38

CX Basic pKa: ┄

CX LogP: 0.58

CX LogD: 0.58

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.75

Np Likeness Score: 0.54

References

1. Liu J, Wu G, Cui G, Wang WX, Zhao M, Wang C, Zhang Z, Peng S..  (2007)  A new class of anti-thrombosis hexahydropyrazino-[1',2':1,6]pyrido-[3,4-b]-indole-1,4-dions: design, synthesis, logK determination, and QSAR analysis.,  15  (17): [PMID:17590343] [10.1016/j.bmc.2007.06.012]

Source

Source(1):

• Scientific Literature