(R)-gamma-(3-trifluoromethyl-benzyl)-L-proline Hydrochloride

ID: ALA4100876

Cas Number: 1049743-55-6

PubChem CID: 2762027

Max Phase: Preclinical

Molecular Formula: C13H15ClF3NO2

Molecular Weight: 273.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(O)[C@@H]1C[C@@H](Cc2cccc(C(F)(F)F)c2)CN1

Standard InChI:  InChI=1S/C13H14F3NO2.ClH/c14-13(15,16)10-3-1-2-8(5-10)4-9-6-11(12(18)19)17-7-9;/h1-3,5,9,11,17H,4,6-7H2,(H,18,19);1H/t9-,11+;/m1./s1

Standard InChI Key:  POALZTWRXIMVHI-XQKZEKTMSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   11.2737  -10.5931    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6002  -12.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2708  -13.2342    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9354  -12.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6705  -11.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8478  -11.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7179  -12.9857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8956  -13.7873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3271  -12.4303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3616  -11.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7554  -10.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5812  -10.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9748   -9.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5429   -9.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7132   -9.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3234   -9.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2799   -8.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8872   -7.8160    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.5604   -7.6407    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.4295   -8.3399    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  2  1  0
  4  7  1  1
  7  8  2  0
  7  9  1  0
  6 10  1  6
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 17 18  1  0
 17 19  1  0
 17 20  1  0
 15 17  1  0
M  END

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: 273.25

Molecular Weight (Monoisotopic): 273.0977

AlogP: 2.31

#Rotatable Bonds: 3

Polar Surface Area: 49.33

Molecular Species: ZWITTERION

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.71

CX Basic pKa: 11.47

CX LogP: 0.25

CX LogD: 0.25

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.89

Np Likeness Score: -0.13

References

1.  (2014)  D-serine transporter inhibitors as pharmaceutical compositions for the treatment of central nervous system disorders, 

2. Singh K, Tanui R, Gameiro A, Eisenberg G, Colas C, Schlessinger A, Grewer C..  (2017)  Structure activity relationships of benzylproline-derived inhibitors of the glutamine transporter ASCT2.,  27  (3): [PMID:28057420] [10.1016/j.bmcl.2016.12.063]

Source

Source(2):

• Scientific Literature
• Patent Bioactivity Data