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

ID: ALA1096294

PubChem CID: 46192872

Max Phase: Preclinical

Molecular Formula: C25H25N3O3

Molecular Weight: 415.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1c2ccccc2c2cc(C(=O)N[C@@H](Cc3ccccc3)C(=O)O)ncc21

Standard InChI:  InChI=1S/C25H25N3O3/c1-2-3-13-28-22-12-8-7-11-18(22)19-15-20(26-16-23(19)28)24(29)27-21(25(30)31)14-17-9-5-4-6-10-17/h4-12,15-16,21H,2-3,13-14H2,1H3,(H,27,29)(H,30,31)/t21-/m0/s1

Standard InChI Key:  FOVPWPAYZJKQKS-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.1886   -8.7847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4639   -9.1791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2093   -7.9600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0763   -5.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5812   -6.4369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9080   -7.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8937   -5.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2232   -6.6234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7299   -7.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0027   -6.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9965   -7.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7096   -8.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4293   -7.7240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4315   -6.8925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7179   -6.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1470   -6.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8605   -6.8959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1489   -5.6567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5759   -6.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2894   -6.8992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5778   -5.6601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0048   -6.4884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2875   -7.7242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4475  -10.0038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7249  -10.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2933   -5.2492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -5.6660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7175   -5.2559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7199   -4.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0014   -4.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2893   -4.4285    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
 24  2  1  0
  6  9  2  0
 24 25  1  0
 11 12  1  0
 21 26  1  0
  1  2  1  0
 26 27  2  0
 12 13  2  0
 27 28  1  0
  8  7  2  0
 28 29  2  0
 13 14  1  0
 29 30  1  0
  7  4  1  0
 30 31  2  0
 31 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096294

   (2S)-2-[(9-butylpyrido[3,4-b]indole-3-carbonyl)amino]-3-phenylpropanoic 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: 415.49

Molecular Weight (Monoisotopic): 415.1896

AlogP: 4.42

#Rotatable Bonds: 8

Polar Surface Area: 84.22

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.74

CX Basic pKa: 1.91

CX LogP: 4.47

CX LogD: 1.29

Aromatic Rings: 4

Heavy Atoms: 31

QED Weighted: 0.45

Np Likeness Score: -0.55

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