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

ID: ALA1096615

PubChem CID: 46192874

Max Phase: Preclinical

Molecular Formula: C25H25N3O4

Molecular Weight: 431.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCn1c2ccccc2c2cc(C(=O)N[C@@H](Cc3ccc(O)cc3)C(=O)O)ncc21

Standard InChI:  InChI=1S/C25H25N3O4/c1-2-3-12-28-22-7-5-4-6-18(22)19-14-20(26-15-23(19)28)24(30)27-21(25(31)32)13-16-8-10-17(29)11-9-16/h4-11,14-15,21,29H,2-3,12-13H2,1H3,(H,27,30)(H,31,32)/t21-/m0/s1

Standard InChI Key:  QWKQJQFIPSCPRN-NRFANRHFSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   13.8302   -8.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1056   -8.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8510   -7.6850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7179   -5.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2229   -6.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5497   -6.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5354   -5.5930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8649   -6.3484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3715   -7.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6444   -6.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6382   -7.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3512   -7.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0710   -7.4490    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0732   -6.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3595   -6.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7886   -6.2067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5021   -6.6209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7906   -5.3817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2176   -6.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9311   -6.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2195   -5.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6465   -6.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9291   -7.4492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0892   -9.7288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3666  -10.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9349   -4.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6442   -5.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3592   -4.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3615   -4.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6430   -3.7410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9310   -4.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0764   -3.7432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  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
 14 15  2  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096615

   (2S)-2-[(9-butylpyrido[3,4-b]indole-3-carbonyl)amino]-3-(4-hydroxyphenyl)propanoic 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: 431.49

Molecular Weight (Monoisotopic): 431.1845

AlogP: 4.12

#Rotatable Bonds: 8

Polar Surface Area: 104.45

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.56

CX Basic pKa: 1.90

CX LogP: 4.13

CX LogD: 0.91

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -0.38

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