(R)-gamma-(3-fluoro-benzyl)-L-proline hydrochloride

ID: ALA4078902

Cas Number: 1373512-33-4

PubChem CID: 45026930

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](Cc2cccc(F)c2)CN1

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

Standard InChI Key:  UEJCKIYKRFAMOV-XQKZEKTMSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    0.8536  -20.5514    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9458  -20.5915    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7708  -20.5915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0275  -19.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3583  -19.3207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6932  -19.8074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570  -18.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0708  -18.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7828  -18.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4961  -18.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4953  -17.2561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7752  -16.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0648  -17.2602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2549  -21.2595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185  -22.0127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0755  -21.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7711  -16.0200    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
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: 1.69

CX Basic pKa: 11.46

CX LogP: -0.48

CX LogD: -0.48

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.81

Np Likeness Score: -0.05

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