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

ID: ALA4068036

Cas Number: 1217789-20-2

PubChem CID: 2761962

Max Phase: Preclinical

Molecular Formula: C12H16ClNO2

Molecular Weight: 205.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(O)[C@@H]1C[C@@H](Cc2ccccc2)CN1

Standard InChI:  InChI=1S/C12H15NO2.ClH/c14-12(15)11-7-10(8-13-11)6-9-4-2-1-3-5-9;/h1-5,10-11,13H,6-8H2,(H,14,15);1H/t10-,11+;/m1./s1

Standard InChI Key:  GPWGPOYNAWMDDN-DHXVBOOMSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    0.9521   -6.4346    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5709   -6.4336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3959   -6.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6527   -5.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9834   -5.1626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3183   -5.6494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9821   -4.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6960   -3.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4079   -4.3369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1213   -3.9239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1205   -3.0981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4004   -2.6868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6899   -3.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8800   -7.1016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5436   -7.8549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7006   -7.0163    0.0000 O   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
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: 205.26

Molecular Weight (Monoisotopic): 205.1103

AlogP: 1.29

#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: 2.12

CX Basic pKa: 11.48

CX LogP: -0.63

CX LogD: -0.63

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.78

Np Likeness Score: 0.69

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