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

ID: ALA4098554

Cas Number: 1049734-78-2

PubChem CID: 2762000

Max Phase: Preclinical

Molecular Formula: C12H15ClN2O4

Molecular Weight: 250.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C12H14N2O4.ClH/c15-12(16)10-6-8(7-13-10)5-9-3-1-2-4-11(9)14(17)18;/h1-4,8,10,13H,5-7H2,(H,15,16);1H/t8-,10+;/m1./s1

Standard InChI Key:  KAZGTSFNVQSTNN-SCYNACPDSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
    7.6821  -13.1975    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.5084  -13.3085    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3335  -13.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5902  -12.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9210  -12.0377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2558  -12.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9196  -11.2127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6335  -10.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3455  -11.2120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0588  -10.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0580   -9.9731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3379   -9.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6274   -9.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8176  -13.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4812  -14.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6381  -13.8913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9072   -9.5680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1954   -9.9850    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9020   -8.7431    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
 17 18  2  0
 17 19  1  0
 13 17  1  0
M  CHG  2  17   1  19  -1
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: 250.25

Molecular Weight (Monoisotopic): 250.0954

AlogP: 1.20

#Rotatable Bonds: 4

Polar Surface Area: 92.47

Molecular Species: ZWITTERION

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.16

CX Basic pKa: 11.36

CX LogP: -0.69

CX LogD: -0.69

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.62

Np Likeness Score: -0.16

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