(3S)-2-(3-sulfanylpropanoyl)-1,3,4,9-tetrahydropyrido[3,4-b]indole-3-carboxylic acid

ID: ALA5283805

Max Phase: Preclinical

Molecular Formula: C15H16N2O3S

Molecular Weight: 304.37

Names and Identifiers

Canonical SMILES:  O=C(O)[C@@H]1Cc2c([nH]c3ccccc23)CN1C(=O)CCS

Standard InChI:  InChI=1S/C15H16N2O3S/c18-14(5-6-21)17-8-12-10(7-13(17)15(19)20)9-3-1-2-4-11(9)16-12/h1-4,13,16,21H,5-8H2,(H,19,20)/t13-/m0/s1

Standard InChI Key:  GCXZPZAQMOQPHW-ZDUSSCGKSA-N

Molfile:  

 
     RDKit          2D

 21 23  0  0  0  0  0  0  0  0999 V2000
    1.4623    1.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7978    0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1847    0.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1847   -0.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4701   -0.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4701   -1.8105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443   -2.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1847   -2.2230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443   -0.5728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2443    0.2522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4701    0.6648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417    1.4718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.9853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -1.8105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735   -0.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3878   -0.9852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1024   -0.5727    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6218    0.7178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1024    1.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7669    2.1370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9462    2.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  3  2  1  0
  4  3  1  0
  5  4  1  0
  5  6  1  1
  6  7  1  0
  6  8  2  0
  9  5  1  0
 10  9  1  0
 11 10  1  0
  3 11  2  0
 11 12  1  0
 12  1  1  0
 13  9  1  0
 13 14  2  0
 15 13  1  0
 16 15  1  0
 16 17  1  0
  2 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  1 21  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5283805

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 304.37

Molecular Weight (Monoisotopic): 304.0882

AlogP: 1.83

#Rotatable Bonds: 3

Polar Surface Area: 73.40

Molecular Species: ACID

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.01

CX Basic pKa: ┄

CX LogP: 1.56

CX LogD: -1.59

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.76

Np Likeness Score: -0.38

References

1. Van der Poorten O, Knuhtsen A, Sejer Pedersen D, Ballet S, Tourwé D..  (2016)  Side Chain Cyclized Aromatic Amino Acids: Great Tools as Local Constraints in Peptide and Peptidomimetic Design.,  59  (24): [PMID:27690430] [10.1021/acs.jmedchem.6b01029]

Source

Source(1):

• Scientific Literature