2-Amino-3-(3-hydroxy-5-thiazol-2-yl-isoxazol-4-yl)-propionic acid

ID: ALA310897

PubChem CID: 10562939

Max Phase: Preclinical

Molecular Formula: C9H9N3O4S

Molecular Weight: 255.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(Cc1c(O)noc1-c1nccs1)C(=O)O

Standard InChI:  InChI=1S/C9H9N3O4S/c10-5(9(14)15)3-4-6(16-12-7(4)13)8-11-1-2-17-8/h1-2,5H,3,10H2,(H,12,13)(H,14,15)

Standard InChI Key:  QEGZVBVIVYRNHK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 18  0  0  0  0  0  0  0  0999 V2000
    2.6417   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4542   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -4.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -3.9125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9375   -4.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2792   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -3.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -4.8042    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -2.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -4.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -4.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167   -1.6417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -2.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2167   -3.2417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7917   -2.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  5  2  0
  5  1  1  0
  6  2  1  0
  7  1  1  0
  8  6  2  0
  9 11  1  0
 10  6  1  0
 11  7  1  0
 12  8  1  0
 13 10  1  0
 14  9  2  0
 15  5  1  0
 16 11  1  0
 17  9  1  0
  3  4  1  0
 12 13  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA310897

   2-Amino-3-[3-oxo-5-(1,3-thiazol-2-yl)-1,2-oxazol-4-yl]propanoic 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: 255.25

Molecular Weight (Monoisotopic): 255.0314

AlogP: 0.46

#Rotatable Bonds: 4

Polar Surface Area: 122.47

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.75

CX Basic pKa: 7.23

CX LogP: -1.93

CX LogD: -3.43

Aromatic Rings: 2

Heavy Atoms: 17

QED Weighted: 0.72

Np Likeness Score: -0.58

References

1. Falch E, Brehm L, Mikkelsen I, Johansen TN, Skjaerbaek N, Nielsen B, Stensbøl TB, Ebert B, Krogsgaard-Larsen P..  (1998)  Heteroaryl analogues of AMPA. 2. Synthesis, absolute stereochemistry, photochemistry, and structure-activity relationships.,  41  (14): [PMID:9651156] [10.1021/jm9801206]

2. 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]

Source

Source(1):

• Scientific Literature