(2S,4R)-4-(4-Acetyl-2-carboxyphenoxy)pyrrolidine-2-carboxylic Acid

ID: ALA4090961

Chembl Id: CHEMBL4090961

PubChem CID: 90480171

Max Phase: Preclinical

Molecular Formula: C14H15NO6

Molecular Weight: 293.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc(O[C@H]2CN[C@H](C(=O)O)C2)c(C(=O)O)c1

Standard InChI:  InChI=1S/C14H15NO6/c1-7(16)8-2-3-12(10(4-8)13(17)18)21-9-5-11(14(19)20)15-6-9/h2-4,9,11,15H,5-6H2,1H3,(H,17,18)(H,19,20)/t9-,11+/m1/s1

Standard InChI Key:  KAZFDFAPKWRBAV-KOLCDFICSA-N

Alternative Forms

1. Parent:

   

   ALA4090961

   (2S,4R)-4-(4-acetyl-2-carboxyphenoxy)pyrrolidine-2-carboxylic acid

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: 293.28

Molecular Weight (Monoisotopic): 293.0899

AlogP: 0.78

#Rotatable Bonds: 5

Polar Surface Area: 112.93

Molecular Species: ZWITTERION

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 0.81

CX Basic pKa: 10.53

CX LogP: -2.20

CX LogD: -5.43

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.69

Np Likeness Score: 0.35

References

1. Krogsgaard-Larsen N, Delgar CG, Koch K, Brown PM, Møller C, Han L, Huynh TH, Hansen SW, Nielsen B, Bowie D, Pickering DS, Kastrup JS, Frydenvang K, Bunch L..  (2017)  Design and Synthesis of a Series of l-trans-4-Substituted Prolines as Selective Antagonists for the Ionotropic Glutamate Receptors Including Functional and X-ray Crystallographic Studies of New Subtype Selective Kainic Acid Receptor Subtype 1 (GluK1) Antagonist (2S,4R)-4-(2-Carboxyphenoxy)pyrrolidine-2-carboxylic Acid.,  60  (1): [PMID:28005385] [10.1021/acs.jmedchem.6b01516]

Source

Source(1):

• Scientific Literature