Ethyl 9-(2-picolyl)-beta-carboline-3-carboxylate

ID: ALA3608811

PubChem CID: 122187131

Max Phase: Preclinical

Molecular Formula: C20H17N3O2

Molecular Weight: 331.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1cc2c3ccccc3n(Cc3ccccn3)c2cn1

Standard InChI:  InChI=1S/C20H17N3O2/c1-2-25-20(24)17-11-16-15-8-3-4-9-18(15)23(19(16)12-22-17)13-14-7-5-6-10-21-14/h3-12H,2,13H2,1H3

Standard InChI Key:  MQCXLBWKQYIVHC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -3.7006   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4915    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2274   -0.6045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732   -1.3190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372   -0.6045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7372    0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    1.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0356    1.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0332    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0760    0.9801    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3312    3.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3293    5.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031   -2.8205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -3.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3092   -5.0691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6108   -5.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9072   -5.0601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9021   -3.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6004   -2.8146    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
 14 15  1  0
 14 16  2  0
 12 14  1  0
 15 17  1  0
 17 18  1  0
  7 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3608811

   ---

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: 331.38

Molecular Weight (Monoisotopic): 331.1321

AlogP: 3.81

#Rotatable Bonds: 4

Polar Surface Area: 57.01

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.93

CX LogP: 3.23

CX LogD: 3.23

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: -1.16

References

1. Chen YF, Lin YC, Chen JP, Chan HC, Hsu MH, Lin HY, Kuo SC, Huang LJ..  (2015)  Synthesis and biological evaluation of novel 3,9-substituted β-carboline derivatives as anticancer agents.,  25  (18): [PMID:26235951] [10.1016/j.bmcl.2015.07.058]

Source

Source(1):

• Scientific Literature