(R)-gamma-(4-fluoro-benzyl)-L-proline hydrochloride

ID: ALA4103180

Cas Number: 1049733-41-6

PubChem CID: 2761970

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](Cc2ccc(F)cc2)CN1

Standard InChI:  InChI=1S/C12H14FNO2.ClH/c13-10-3-1-8(2-4-10)5-9-6-11(12(15)16)14-7-9;/h1-4,9,11,14H,5-7H2,(H,15,16);1H/t9-,11+;/m1./s1

Standard InChI Key:  LOGXELIZYUDTKZ-XQKZEKTMSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    1.2475  -13.0662    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3208  -13.1839    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1459  -13.1839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4027  -12.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7334  -11.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0684  -12.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7322  -11.0879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4460  -10.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1580  -11.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8714  -10.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8706   -9.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504   -9.4371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4400   -9.8524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6301  -13.8519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2936  -14.6052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4507  -13.7666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5838   -9.4338    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
 11 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: 1.68

CX Basic pKa: 11.49

CX LogP: -0.48

CX LogD: -0.48

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.81

Np Likeness Score: 0.17

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