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

ID: ALA1094612

PubChem CID: 46193003

Max Phase: Preclinical

Molecular Formula: C26H27N3O3

Molecular Weight: 429.52

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H27N3O3/c1-17(2)24(26(31)32)28-25(30)21-15-20-19-12-6-7-13-22(19)29(23(20)16-27-21)14-8-11-18-9-4-3-5-10-18/h3-7,9-10,12-13,15-17,24H,8,11,14H2,1-2H3,(H,28,30)(H,31,32)/t24-/m0/s1

Standard InChI Key:  QDWBHLQUCXCRBI-DEOSSOPVSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   14.7761  -15.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0514  -15.9541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7968  -14.7350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.6638  -12.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1687  -13.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4955  -13.9699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4812  -12.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8107  -13.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -14.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5902  -13.6624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5840  -14.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2971  -14.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0168  -14.4990    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0190  -13.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3054  -13.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7345  -13.2567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4480  -13.6709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7364  -12.4317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1634  -13.2601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8769  -13.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1653  -12.4351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5923  -13.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8750  -14.4992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0372  -16.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3156  -17.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6086  -16.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8876  -17.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8728  -17.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5850  -18.3984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3032  -17.9966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8808  -12.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4518  -12.0209    0.0000 C   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
 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
 21 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094612

   (2S)-3-methyl-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: 429.52

Molecular Weight (Monoisotopic): 429.2052

AlogP: 4.66

#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: 3.73

CX Basic pKa: 1.91

CX LogP: 4.83

CX LogD: 1.65

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.43

Np Likeness Score: -0.63

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