N-(9-Phenylpropyl-b-carboline-3-carbonyl)-L-methionine

ID: ALA1094613

PubChem CID: 46193005

Max Phase: Preclinical

Molecular Formula: C26H27N3O3S

Molecular Weight: 461.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CSCC[C@H](NC(=O)c1cc2c3ccccc3n(CCCc3ccccc3)c2cn1)C(=O)O

Standard InChI:  InChI=1S/C26H27N3O3S/c1-33-15-13-21(26(31)32)28-25(30)22-16-20-19-11-5-6-12-23(19)29(24(20)17-27-22)14-7-10-18-8-3-2-4-9-18/h2-6,8-9,11-12,16-17,21H,7,10,13-15H2,1H3,(H,28,30)(H,31,32)/t21-/m0/s1

Standard InChI Key:  MEABAGYJSNWZMI-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
   -3.0198  -24.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7444  -25.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9990  -23.8141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1321  -21.6281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6271  -22.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3003  -23.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3146  -21.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9851  -22.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4785  -23.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2056  -22.7416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118  -23.5698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4988  -23.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790  -23.5781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7768  -22.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905  -22.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0614  -22.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6521  -22.7501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0594  -21.5109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3676  -22.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0811  -22.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3695  -21.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7965  -22.3426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0791  -23.5784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7587  -25.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4802  -26.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1872  -25.8277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9082  -26.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9230  -27.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2108  -27.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4927  -27.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0849  -21.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0869  -20.2784    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.8023  -19.8676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
 24  2  1  0
  6  9  2  0
 24 25  1  0
 11 12  1  0
 25 26  2  0
  1  2  1  0
 26 27  1  0
 12 13  2  0
 27 28  2  0
  8  7  2  0
 28 29  1  0
 13 14  1  0
 29 30  2  0
 30 25  1  0
  7  4  1  0
 21 31  1  0
 14 15  2  0
 31 32  1  0
 15 10  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094613

   (2S)-4-methylsulfanyl-2-[[9-(3-phenylpropyl)pyrido[3,4-b]indole-3-carbonyl]amino]butanoic acid

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: 461.59

Molecular Weight (Monoisotopic): 461.1773

AlogP: 4.76

#Rotatable Bonds: 10

Polar Surface Area: 84.22

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.70

CX Basic pKa: 1.91

CX LogP: 4.59

CX LogD: 1.40

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: -0.74

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