(RS)-2-amino-3-[3-hydroxy-5-(2-benzyl-2H-5-tetrazolyl)-4-isoxazolyl]propionic acid

ID: ALA388746

Chembl Id: CHEMBL388746

PubChem CID: 16659202

Max Phase: Preclinical

Molecular Formula: C14H14N6O4

Molecular Weight: 330.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(Cc1c(O)noc1-c1nnn(Cc2ccccc2)n1)C(=O)O

Standard InChI:  InChI=1S/C14H14N6O4/c15-10(14(22)23)6-9-11(24-18-13(9)21)12-16-19-20(17-12)7-8-4-2-1-3-5-8/h1-5,10H,6-7,15H2,(H,18,21)(H,22,23)

Standard InChI Key:  ZNMNDDBPIVAUGG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA388746

   (RS)-2-amino-3-[3-hydroxy-5-(2-benzyl-2H-5-tetrazolyl)-4-isoxazolyl]propionic 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: 330.30

Molecular Weight (Monoisotopic): 330.1077

AlogP: 0.04

#Rotatable Bonds: 6

Polar Surface Area: 153.18

Molecular Species: ZWITTERION

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.77

CX Basic pKa: 8.80

CX LogP: -0.80

CX LogD: -2.53

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.57

Np Likeness Score: -1.04

References

1. Vogensen SB, Frydenvang K, Greenwood JR, Postorino G, Nielsen B, Pickering DS, Ebert B, Bølcho U, Egebjerg J, Gajhede M, Kastrup JS, Johansen TN, Clausen RP, Krogsgaard-Larsen P..  (2007)  A tetrazolyl-substituted subtype-selective AMPA receptor agonist.,  50  (10): [PMID:17455929] [10.1021/jm061439q]

2. Jensen AA, Christesen T, Bølcho U, Greenwood JR, Postorino G, Vogensen SB, Johansen TN, Egebjerg J, Bräuner-Osborne H, Clausen RP..  (2007)  Functional characterization of Tet-AMPA [tetrazolyl-2-amino-3-(3-hydroxy-5-methyl- 4-isoxazolyl)propionic acid] analogues at ionotropic glutamate receptors GluR1-GluR4. The molecular basis for the functional selectivity profile of 2-Bn-Tet-AMPA.,  50  (17): [PMID:17672447] [10.1021/jm070532r]

3. Sainas S, Temperini P, Farnsworth JC, Yi F, Møllerud S, Jensen AA, Nielsen B, Passoni A, Kastrup JS, Hansen KB, Boschi D, Pickering DS, Clausen RP, Lolli ML..  (2019)  Use of the 4-Hydroxytriazole Moiety as a Bioisosteric Tool in the Development of Ionotropic Glutamate Receptor Ligands.,  62  (9): [PMID:30943028] [10.1021/acs.jmedchem.8b01986]

Source

Source(1):

• Scientific Literature