(S)-2-amino-3-[5-tertbutyl-3-(phosphono-methoxy)-4-isoxazolyl]-propionic acid

ID: ALA594840

PubChem CID: 447249

Max Phase: Preclinical

Molecular Formula: C11H19N2O7P

Molecular Weight: 322.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1onc(OCP(=O)(O)O)c1C[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C11H19N2O7P/c1-11(2,3)8-6(4-7(12)10(14)15)9(13-20-8)19-5-21(16,17)18/h7H,4-5,12H2,1-3H3,(H,14,15)(H2,16,17,18)/t7-/m0/s1

Standard InChI Key:  AGSOOCUNMTYPSE-ZETCQYMHSA-N

Molfile:  

     RDKit          2D

 21 21  0  0  0  0  0  0  0  0999 V2000
   -0.8692   -0.5183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4277    0.8407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969    1.3506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0407    0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8254    0.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4385   -0.0084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6918    0.5858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1270   -0.8663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4369   -0.1988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0244    1.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4625   -1.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6119   -0.1988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3570    0.5858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0244    1.0707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0244    2.7207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1994    1.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8494    1.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0224   -2.2874    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.6451   -2.7723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5073   -2.9548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898   -1.8025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  6
  2  4  1  0
  2 13  1  0
  5  3  1  0
  4  5  1  0
  5  6  2  0
  9  7  1  0
 14  7  1  0
 11  8  1  0
 12  8  1  0
 12  9  2  0
 10 14  1  0
 10 15  1  0
 16 10  1  0
 17 10  1  0
 11 18  1  0
 12 13  1  0
 13 14  2  0
 19 18  2  0
 20 18  1  0
 21 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA594840

   2-Amino-3-(5-tert-butyl-3-(phosphonomethoxy)-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: 322.25

Molecular Weight (Monoisotopic): 322.0930

AlogP: 0.44

#Rotatable Bonds: 6

Polar Surface Area: 156.11

Molecular Species: ZWITTERION

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.27

CX Basic pKa: 9.15

CX LogP: -1.10

CX LogD: -4.57

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: 0.11

References

1. Szymańska E, Pickering DS, Nielsen B, Johansen TN..  (2009)  3-Substituted phenylalanines as selective AMPA- and kainate receptor ligands.,  17  (17): [PMID:19656686] [10.1016/j.bmc.2009.07.021]

2. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

3. Szymańska E, Chałupnik P, Szczepańska K, Cuñado Moral AM, Pickering DS, Nielsen B, Johansen TN, Kieć-Kononowicz K..  (2016)  Design, synthesis and structure-activity relationships of novel phenylalanine-based amino acids as kainate receptors ligands.,  26  (22): [PMID:27765511] [10.1016/j.bmcl.2016.09.075]

4. Szymańska E, Nielsen B, Johansen TN, Cuñado Moral AM, Pickering DS, Szczepańska K, Mickowska A, Kieć-Kononowicz K..  (2017)  Pharmacological characterization and binding modes of novel racemic and optically active phenylalanine-based antagonists of AMPA receptors.,  138  [PMID:28738307] [10.1016/j.ejmech.2017.07.007]

Source

Source(1):

• Scientific Literature