serine biphenyl-4-carboxylate

ID: ALA3576945

PubChem CID: 122177347

Max Phase: Preclinical

Molecular Formula: C16H15NO4

Molecular Weight: 285.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](COC(=O)c1ccc(-c2ccccc2)cc1)C(=O)O

Standard InChI:  InChI=1S/C16H15NO4/c17-14(15(18)19)10-21-16(20)13-8-6-12(7-9-13)11-4-2-1-3-5-11/h1-9,14H,10,17H2,(H,18,19)/t14-/m0/s1

Standard InChI Key:  JMEQFOWNXZGEET-AWEZNQCLSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2297   -5.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877   -7.2109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5987    1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6012    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9015    3.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1969    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8967    0.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  1  1
  2  5  1  0
  2  6  2  0
  3  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15  9  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 13 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3576945

   ---

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: 285.30

Molecular Weight (Monoisotopic): 285.1001

AlogP: 1.92

#Rotatable Bonds: 5

Polar Surface Area: 89.62

Molecular Species: ZWITTERION

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.84

CX Basic pKa: 8.60

CX LogP: 0.26

CX LogD: 0.23

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.82

Np Likeness Score: 0.06

References

1. Schulte ML, Dawson ES, Saleh SA, Cuthbertson ML, Manning HC..  (2015)  2-Substituted Nγ-glutamylanilides as novel probes of ASCT2 with improved potency.,  25  (1): [PMID:25435145] [10.1016/j.bmcl.2014.10.098]

2. Schulte ML, Khodadadi AB, Cuthbertson ML, Smith JA, Manning HC..  (2016)  2-Amino-4-bis(aryloxybenzyl)aminobutanoic acids: A novel scaffold for inhibition of ASCT2-mediated glutamine transport.,  26  (3): [PMID:26750251] [10.1016/j.bmcl.2015.12.031]

Source

Source(1):

• Scientific Literature