Structure Database (LMSD)

Common Name
2S-amino-butanoic acid
Systematic Name
2S-amino-butanoic acid
Synonyms
  • (S)-2-Aminobutanoic acid
LM ID
LMFA01100034
Formula
Exact Mass
Calculate m/z
103.063329
Status
Curated



Classification

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

KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID

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

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Created at
-
Updated at
30th Jan 2023