(R)-gamma-(3,4-difluoro-benzyl)-L-proline hydrochloride

ID: ALA4068819

Cas Number: 1049743-09-0

PubChem CID: 2762021

Max Phase: Preclinical

Molecular Formula: C12H14ClF2NO2

Molecular Weight: 241.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(O)[C@@H]1C[C@@H](Cc2ccc(F)c(F)c2)CN1

Standard InChI:  InChI=1S/C12H13F2NO2.ClH/c13-9-2-1-7(4-10(9)14)3-8-5-11(12(16)17)15-6-8;/h1-2,4,8,11,15H,3,5-6H2,(H,16,17);1H/t8-,11+;/m1./s1

Standard InChI Key:  MCIYUVYFHTWUSB-NINOIYOQSA-N

Molfile:  

     RDKit          2D

 18 18  0  0  0  0  0  0  0  0999 V2000
   14.1824  -22.4226    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.1675  -22.3971    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.9926  -22.3971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2493  -21.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5800  -21.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9149  -21.6130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5787  -20.3012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2926  -19.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0046  -20.3004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7180  -19.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7172  -19.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9970  -18.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2866  -19.0656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4767  -23.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1403  -23.8185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2973  -22.9799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9929  -17.8253    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.4306  -18.6470    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
 12 17  1  0
 11 18  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: 241.24

Molecular Weight (Monoisotopic): 241.0914

AlogP: 1.57

#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: 1.33

CX Basic pKa: 11.46

CX LogP: -0.34

CX LogD: -0.34

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.84

Np Likeness Score: -0.23

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