1-Methyl-7-(3-methylbutyloxy)-9-(3-methylbutyl)-beta-carboline

ID: ALA2164713

PubChem CID: 60195194

Max Phase: Preclinical

Molecular Formula: C22H30N2O

Molecular Weight: 338.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nccc2c3ccc(OCCC(C)C)cc3n(CCC(C)C)c12

Standard InChI:  InChI=1S/C22H30N2O/c1-15(2)9-12-24-21-14-18(25-13-10-16(3)4)6-7-19(21)20-8-11-23-17(5)22(20)24/h6-8,11,14-16H,9-10,12-13H2,1-5H3

Standard InChI Key:  CYNQFAAXQWCODJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.7484   -8.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7473   -9.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4621  -10.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4603   -8.4204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1756   -8.8296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1759   -9.6560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9626   -9.9103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9615   -8.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4457   -9.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2631   -9.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5972   -8.4008    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1080   -7.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2924   -7.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0325  -10.0725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7487   -9.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3768  -10.6237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9660  -11.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3183   -9.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6035  -10.0713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8894   -9.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1746  -10.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8901   -8.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1410  -11.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7302  -12.0567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7268  -10.6278    0.0000 C   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
  2 14  1  0
 10 15  1  0
  7 16  1  0
 16 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 17 23  1  0
 23 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2164713

   1-Methyl-7-(3-methylbutyloxy)-9-(3-methylbutyl)-beta-carboline

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: 338.50

Molecular Weight (Monoisotopic): 338.2358

AlogP: 5.97

#Rotatable Bonds: 7

Polar Surface Area: 27.05

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.04

CX LogP: 5.29

CX LogD: 5.27

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.53

Np Likeness Score: -0.26

References

1. Frédérick R, Bruyère C, Vancraeynest C, Reniers J, Meinguet C, Pochet L, Backlund A, Masereel B, Kiss R, Wouters J..  (2012)  Novel trisubstituted harmine derivatives with original in vitro anticancer activity.,  55  (14): [PMID:22770529] [10.1021/jm300542e]

2. Meinguet C, Bruyère C, Frédérick R, Mathieu V, Vancraeynest C, Pochet L, Laloy J, Mortier J, Wolber G, Kiss R, Masereel B, Wouters J..  (2015)  3D-QSAR, design, synthesis and characterization of trisubstituted harmine derivatives with in vitro antiproliferative properties.,  94  [PMID:25747498] [10.1016/j.ejmech.2015.02.044]

Source

Source(1):

• Scientific Literature