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

ID: ALA1096293

PubChem CID: 46192870

Max Phase: Preclinical

Molecular Formula: C21H25N3O3S

Molecular Weight: 399.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1c2ccccc2c2cc(C(=O)N[C@@H](CCSC)C(=O)O)ncc21

Standard InChI:  InChI=1S/C21H25N3O3S/c1-3-4-10-24-18-8-6-5-7-14(18)15-12-17(22-13-19(15)24)20(25)23-16(21(26)27)9-11-28-2/h5-8,12-13,16H,3-4,9-11H2,1-2H3,(H,23,25)(H,26,27)/t16-/m0/s1

Standard InChI Key:  MJXSASAIZIOSTE-INIZCTEOSA-N

Molfile:  

     RDKit          2D

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   -4.5069   -9.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7615   -8.1350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8946   -5.9490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3896   -6.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0628   -7.3699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0771   -6.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7476   -6.7984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2410   -7.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9681   -7.0624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9743   -7.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2613   -8.3084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5415   -7.8990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5393   -7.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2530   -6.6536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239   -6.6567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1104   -7.0709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8219   -5.8317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051   -6.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3186   -7.0742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6070   -5.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0340   -6.6634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3166   -7.8992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5233  -10.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2459  -10.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3224   -5.4242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3185   -4.6035    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.0310   -4.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
 13 14  1  0
  7  4  1  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
 24  2  1  0
  6  9  2  0
 24 25  1  0
 11 12  1  0
 21 26  1  0
  1  2  1  0
 27 26  1  0
 12 13  2  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096293

   (2S)-2-[(9-butylpyrido[3,4-b]indole-3-carbonyl)amino]-4-methylsulfanylbutanoic 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: 399.52

Molecular Weight (Monoisotopic): 399.1617

AlogP: 3.93

#Rotatable Bonds: 9

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: 3.46

CX LogD: 0.27

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: -0.83

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