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

ID: ALA94859

PubChem CID: 3481675

Max Phase: Preclinical

Molecular Formula: C8H10N6O4

Molecular Weight: 254.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cn1nnc(-c2onc(O)c2CC(N)C(=O)O)n1

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

Standard InChI Key:  YXLQKZHKWIKJKC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 18 19  0  0  0  0  0  0  0  0999 V2000
    3.9917   -6.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -4.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -7.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -6.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -6.9375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -6.2042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -7.5250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9167   -5.6917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -4.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -3.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667   -2.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375   -4.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -4.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3167   -3.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -8.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  1  2  0
  5  1  1  0
  6  5  2  0
  7  2  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  8  1  0
  8  6  1  0
 10  9  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA94859

   (S)-2-Amino-3-[3-hydroxy-5-(2-methyl-2H-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: 1.81

CX Basic pKa: 8.80

CX LogP: -2.52

CX LogD: -4.25

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.59

Np Likeness Score: -0.74

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. 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