2-Amino-3-[3-hydroxy-5-(1-methyl-1H-tetrazol-5-yl)-isoxazol-4-yl]-propionic acid

ID: ALA317790

PubChem CID: 10658567

Max Phase: Preclinical

Molecular Formula: C8H10N6O4

Molecular Weight: 254.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1nnnc1-c1onc(O)c1CC(N)C(=O)O

Standard InChI:  InChI=1S/C8H10N6O4/c1-14-6(10-12-13-14)5-3(7(15)11-18-5)2-4(9)8(16)17/h4H,2,9H2,1H3,(H,11,15)(H,16,17)

Standard InChI Key:  JLVXZYSVVWOWNA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    4.2667   -6.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -6.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -5.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8042   -7.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4792   -7.4042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -6.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9542   -6.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -7.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6042   -6.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3167   -5.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0750   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -3.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2500   -4.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -3.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7250   -4.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625   -5.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -3.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -8.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  2  1  0
  5  6  1  0
  6  2  2  0
  7  1  1  0
  8  4  1  0
  9  7  1  0
 10  3  1  0
 11  3  1  0
 12 13  1  0
 13 11  1  0
 14 12  2  0
 15 10  1  0
 16 13  1  0
 17 12  1  0
 18  4  1  0
 10  9  2  0
  8  5  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA317790

   2-Amino-3-[3-hydroxy-5-(1-methyl-1H-tetrazol-5-yl)-isoxazol-4-yl]-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: 254.21

Molecular Weight (Monoisotopic): 254.0764

AlogP: -1.47

#Rotatable Bonds: 4

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: 1.83

CX Basic pKa: 8.82

CX LogP: -3.21

CX LogD: -4.76

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.59

Np Likeness Score: -1.01

References

1. Bang-Andersen B, Lenz SM, Skjaerbaek N, Søby KK, Hansen HO, Ebert B, Bøgesø KP, Krogsgaard-Larsen P..  (1997)  Heteroaryl analogues of AMPA. Synthesis and quantitative structure-activity relationships.,  40  (18): [PMID:9288165] [10.1021/jm970253b]

2. Vogensen SB, Clausen RP, Greenwood JR, Johansen TN, Pickering DS, Nielsen B, Ebert B, Krogsgaard-Larsen P..  (2005)  Convergent synthesis and pharmacology of substituted tetrazolyl-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid analogues.,  48  (9): [PMID:15857151] [10.1021/jm050014l]

3. 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]

Source

Source(1):

• Scientific Literature