N-(1-Methyl-9-butyl-b-carboline-3-carbonyl)-L-methionine ethylester

ID: ALA1097254

PubChem CID: 46192866

Max Phase: Preclinical

Molecular Formula: C24H31N3O3S

Molecular Weight: 441.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1c2ccccc2c2cc(C(=O)N[C@@H](CCSC)C(=O)OCC)nc(C)c21

Standard InChI:  InChI=1S/C24H31N3O3S/c1-5-7-13-27-21-11-9-8-10-17(21)18-15-20(25-16(3)22(18)27)23(28)26-19(12-14-31-4)24(29)30-6-2/h8-11,15,19H,5-7,12-14H2,1-4H3,(H,26,28)/t19-/m0/s1

Standard InChI Key:  HYKKTFBEIJFUKZ-IBGZPJMESA-N

Molfile:  

     RDKit          2D

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   -4.4652   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7199   -0.8433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8529    1.3427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3479    0.6798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0212   -0.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0354    1.2487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7060    0.4933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1993   -0.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9264    0.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9327   -0.5990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2196   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4999   -0.6073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4977    0.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    0.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7822    0.6350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0687    0.2208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803    1.4599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6467    0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6487    1.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0757    0.6282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3583   -0.6076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7892    0.2141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4817   -2.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2042   -3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3641    1.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7872   -0.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602    2.6882    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2249   -1.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0727    3.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 14 15  2  0
 15 10  1  0
  8  9  1  0
 14 16  1  0
 16 17  1  0
  4  5  2  0
 16 18  2  0
  9  3  1  0
 17 19  1  0
  3 11  1  0
 19 20  1  0
 10  8  1  0
 19 21  1  1
  1  3  1  0
 20 22  1  0
  5  6  1  0
 20 23  2  0
 10 11  2  0
 22 24  1  0
  6  9  2  0
 25  2  1  0
 11 12  1  0
 25 26  1  0
  1  2  1  0
 21 27  1  0
 12 13  2  0
 24 28  1  0
  8  7  2  0
 29 27  1  0
 13 14  1  0
 12 30  1  0
  7  4  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097254

   ethyl (2S)-2-[(9-butyl-1-methylpyrido[3,4-b]indole-3-carbonyl)amino]-4-methylsulfanylbutanoate

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: 441.60

Molecular Weight (Monoisotopic): 441.2086

AlogP: 4.71

#Rotatable Bonds: 10

Polar Surface Area: 73.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.66

CX LogP: 4.21

CX LogD: 4.21

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.46

Np Likeness Score: -0.89

References

1. Ma C, Cao R, Shi B, Li S, Chen Z, Yi W, Peng W, Ren Z, Song H..  (2010)  Synthesis and cytotoxic evaluation of N2-benzylated quaternary beta-carboline amino acid ester conjugates.,  45  (4): [PMID:20122764] [10.1016/j.ejmech.2009.12.060]

Source

Source(1):

• Scientific Literature