trans-methyl (1R,3S)-1-octyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate

ID: ALA4648769

PubChem CID: 156021523

Max Phase: Preclinical

Molecular Formula: C21H30N2O2

Molecular Weight: 342.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCCCCCCC[C@H]1N[C@H](C(=O)OC)Cc2c1[nH]c1ccccc21

Standard InChI:  InChI=1S/C21H30N2O2/c1-3-4-5-6-7-8-13-18-20-16(14-19(22-18)21(24)25-2)15-11-9-10-12-17(15)23-20/h9-12,18-19,22-23H,3-8,13-14H2,1-2H3/t18-,19+/m1/s1

Standard InChI Key:  FYHDKKBRSLVJIZ-MOPGFXCFSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    3.1218  -10.3681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4421   -9.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6706   -9.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1091   -8.5328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147   -8.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0850   -9.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522  -10.1026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4913   -9.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7713   -9.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5755  -10.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1055   -9.3875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8297   -8.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0197   -8.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3628   -7.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1709   -8.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0838   -7.2171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4458   -8.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8501  -10.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6581  -10.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9327  -11.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4035  -12.3348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5955  -12.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0621  -12.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541  -12.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9795  -11.8897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  9  1  0
  8  3  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  2  1  0
  8  9  2  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  1
 14 15  1  0
 14 16  2  0
 15 17  1  0
 10 18  1  6
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4648769

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 342.48

Molecular Weight (Monoisotopic): 342.2307

AlogP: 4.65

#Rotatable Bonds: 8

Polar Surface Area: 54.12

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.50

CX LogP: 5.03

CX LogD: 5.03

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.54

Np Likeness Score: 0.64

References

1. Singh R, Jaisingh A, Maurya IK, Salunke DB..  (2020)  Design, synthesis and bio-evaluation of C-1 alkylated tetrahydro-β-carboline derivatives as novel antifungal lead compounds.,  30  (3): [PMID:31870647] [10.1016/j.bmcl.2019.126869]

2. Dai JK, Dan WJ, Wan JB..  (2022)  Natural and synthetic β-carboline as a privileged antifungal scaffolds.,  229  [PMID:34954591] [10.1016/j.ejmech.2021.114057]

Source

Source(1):

• Scientific Literature