(R)-gamma-(2-fluoro-benzyl)-L-proline hydrochloride

ID: ALA4071517

Cas Number: 1049733-29-0

PubChem CID: 2761965

Max Phase: Preclinical

Molecular Formula: C12H15ClFNO2

Molecular Weight: 223.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(O)[C@@H]1C[C@@H](Cc2ccccc2F)CN1

Standard InChI:  InChI=1S/C12H14FNO2.ClH/c13-10-4-2-1-3-9(10)5-8-6-11(12(15)16)14-7-8;/h1-4,8,11,14H,5-7H2,(H,15,16);1H/t8-,11+;/m1./s1

Standard InChI Key:  HKTWPCCWOYHOCB-NINOIYOQSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    7.9119   -6.4018    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.7915   -6.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6165   -6.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8733   -5.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2040   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5390   -5.5909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2028   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9166   -3.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6286   -4.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3419   -3.8655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3411   -3.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6210   -2.6284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9106   -3.0437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1007   -7.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7642   -7.7962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9212   -6.9577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1935   -2.6357    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
  5  7  1  6
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  3 14  1  1
 14 15  1  0
 14 16  2  0
 13 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: 223.25

Molecular Weight (Monoisotopic): 223.1009

AlogP: 1.43

#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: 11.41

CX LogP: -0.48

CX LogD: -0.48

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.81

Np Likeness Score: -0.13

References

1. 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(1):

• Scientific Literature