(R)-gamma-(4-biphenylmethyl)-L-proline hydrochloride

ID: ALA4085113

Cas Number: 1049745-26-7

PubChem CID: 2762060

Max Phase: Preclinical

Molecular Formula: C18H20ClNO2

Molecular Weight: 281.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cl.O=C(O)[C@@H]1C[C@@H](Cc2ccc(-c3ccccc3)cc2)CN1

Standard InChI:  InChI=1S/C18H19NO2.ClH/c20-18(21)17-11-14(12-19-17)10-13-6-8-16(9-7-13)15-4-2-1-3-5-15;/h1-9,14,17,19H,10-12H2,(H,20,21);1H/t14-,17+;/m1./s1

Standard InChI Key:  SHDWZGVXHRYAOT-CVLQQERVSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   27.4784  -14.8390    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   28.3299  -14.6712    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.1549  -14.6712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4117  -13.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7424  -13.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0774  -13.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7411  -12.5753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4549  -12.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1669  -12.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8803  -12.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8795  -11.3358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1593  -10.9246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4490  -11.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6390  -15.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3026  -16.0925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4597  -15.2540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5918  -10.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3077  -11.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0206  -10.9210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0187  -10.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2979   -9.6848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5881  -10.1011    0.0000 C   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
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  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: 281.36

Molecular Weight (Monoisotopic): 281.1416

AlogP: 2.96

#Rotatable Bonds: 4

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: 2.20

CX Basic pKa: 11.48

CX LogP: 1.02

CX LogD: 1.02

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.91

Np Likeness Score: 0.40

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