Structure Database (LMSD)
Common Name
2S-amino-butanoic acid
Systematic Name
2S-amino-butanoic acid
Synonyms
- (S)-2-Aminobutanoic acid
3D model of 2S-amino-butanoic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
L-2-Aminobutyric acid is a non-proteinogenic amino acid.1 It inhibits LPS-induced nitric oxide (NO) production in, and reduces the bactericidal activity of, isolated mouse bone marrow-derived macrophages (BMDMs) when used at concentrations of 0.1 and 1 mM. L-2-Aminobutyric acid (75 mg/kg) increases survival in mouse models of sepsis induced by LPS or cecum ligation and puncture and decreases disease severity in a mouse model of inflammatory bowel disease (IBD) induced by dextran sodium sulfate (DSS). Serum levels of L-2-aminobutyric acid are increased in patients with COVID-19 and increased serum levels are associated with higher overall survival in patients with head and neck cancer.2,3 It has been used in the synthesis of several compounds, including the antiepileptic levetiracetam and antimycobacterial agent ethambutol .4
This information has been provided by Cayman Chemical
References
2. Cadoni, G., Giraldi, L., Chiarla, C., et al. Prognostic role of serum amino acids in head and neck cancer. Dis. Markers 2291759 (2020).
String Representations
InChiKey (Click to copy)
QWCKQJZIFLGMSD-VKHMYHEASA-N
InChi (Click to copy)
InChI=1S/C4H9NO2/c1-2-3(5)4(6)7/h3H,2,5H2,1H3,(H,6,7)/t3-/m0/s1
SMILES (Click to copy)
[C@H](N)(CC)C(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
7
Rings
0
Aromatic Rings
0
Rotatable Bonds
2
Van der Waals Molecular Volume
103.70
Topological Polar Surface Area
63.32
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
0.09
Molar Refractivity
26.41
Admin
Created at
-
Updated at
30th Jan 2023