rac-(2S)-1-[(2S)-2-methyl-3-sulfanyl-propanoyl]-3,4-dihydro-2H-quinoline-2-carboxylic acid

ID: ALA5275273

Max Phase: Preclinical

Molecular Formula: C14H17NO3S

Molecular Weight: 279.36

Names and Identifiers

Canonical SMILES:  C[C@H](CS)C(=O)N1c2ccccc2CC[C@H]1C(=O)O

Standard InChI:  InChI=1S/C14H17NO3S/c1-9(8-19)13(16)15-11-5-3-2-4-10(11)6-7-12(15)14(17)18/h2-5,9,12,19H,6-8H2,1H3,(H,17,18)/t9-,12+/m1/s1

Standard InChI Key:  AFQRQONIFUVVEI-SKDRFNHKSA-N

Molfile:  

 
     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   -0.0001   -1.6493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0001   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -0.4119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432    0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -0.8243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287   -1.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1432   -2.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143   -2.0618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4287    1.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7120    2.0618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0021    1.6498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0021    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4287   -0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.4117    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  7  6  1  0
  8  7  1  0
  3  8  1  0
  8  9  1  1
  9 10  2  0
  9 11  1  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  4 15  1  0
 16  2  1  0
 16 17  1  1
 18 16  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5275273

   ---

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: 279.36

Molecular Weight (Monoisotopic): 279.0929

AlogP: 1.98

#Rotatable Bonds: 3

Polar Surface Area: 57.61

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.07

CX Basic pKa: ┄

CX LogP: 2.46

CX LogD: -0.65

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.83

Np Likeness Score: -0.06

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