10-methyl-1-(4-nitrophenyl)-1,2,3,4-tetrahydropyrazino[1,2-a]indole

ID: ALA369904

PubChem CID: 11681089

Max Phase: Preclinical

Molecular Formula: C18H17N3O2

Molecular Weight: 307.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c2n(c3ccccc13)CCNC2c1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C18H17N3O2/c1-12-15-4-2-3-5-16(15)20-11-10-19-17(18(12)20)13-6-8-14(9-7-13)21(22)23/h2-9,17,19H,10-11H2,1H3

Standard InChI Key:  BTPDIJZLGANASF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    9.5596   -5.0137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5585   -5.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2729   -6.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2711   -4.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9860   -5.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9862   -5.8406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7759   -4.7532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2643   -5.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7704   -6.0976    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.1041   -6.8575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9327   -6.9511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4266   -6.2785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0919   -5.5122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0304   -3.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5790   -4.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3956   -4.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8826   -4.2737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5500   -3.5182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7258   -3.4312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2426   -4.0966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0363   -2.8523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7052   -2.0931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8585   -2.9352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  3  6  2  0
  7 14  1  0
  6  9  1  0
 13 15  1  0
  8  7  2  0
 15 16  2  0
  7  5  1  0
 16 17  1  0
  8  9  1  0
 17 18  2  0
  1  2  2  0
 18 19  1  0
  5  4  2  0
 19 20  2  0
 20 15  1  0
  4  1  1  0
 18 21  1  0
  5  6  1  0
 21 22  2  0
 21 23  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA369904

   10-Methyl-1-(4-nitrophenyl)-1,2,3,4-tetrahydropyrazino[1,2-a]indole

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: 307.35

Molecular Weight (Monoisotopic): 307.1321

AlogP: 3.55

#Rotatable Bonds: 2

Polar Surface Area: 60.10

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.46

CX LogP: 3.84

CX LogD: 3.51

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.58

Np Likeness Score: -0.72

References

1. Tiwari RK, Singh D, Singh J, Yadav V, Pathak AK, Dabur R, Chhillar AK, Singh R, Sharma GL, Chandra R, Verma AK..  (2006)  Synthesis and antibacterial activity of substituted 1,2,3,4-tetrahydropyrazino [1,2-a] indoles.,  16  (2): [PMID:16246547] [10.1016/j.bmcl.2005.09.066]

Source

Source(1):

• Scientific Literature