Asparagine
C₄H₈N₂O₃·132.118 g/mol·Amino Acids·CID 6267
Amino AcidHistorical
The amide derivative of aspartic acid and the first amino acid ever isolated (from asparagus, 1806). Its side chain is a common site for N-linked glycosylation — the attachment of sugar chains to proteins, critical for cell surface recognition.
IUPAC: (2S)-2,4-diamino-4-oxobutanoic acid
Also known as: asparagine, 70-47-3, (S)-asparagine, Aspartamic acid, agedoite (+14 more)
Molecular Structure
Molecular Propertiesmass · H-bonds · stereo
Molecular Weight
132.120g/mol
Exact Mass
132.053492Da
Monoisotopic Mass
132.053492Da
XLogP
-3.4
Polar Surface Area
106.0Ų
Complexity
134
Formal Charge
0
H-Bond Donors
3
H-Bond Acceptors
4
Rotatable Bonds
3
Heavy Atoms
9
Stereo Centers
1
Bond Stereo
0
Drug-Likeness (Lipinski's Rule of Five)
✓ 132.1 g/mol
MW ≤ 500
✓ -3.4
LogP ≤ 5
✓ 3
H-bond donors ≤ 5
✓ 4
H-bond acceptors ≤ 10
Passes all rules — good oral bioavailability predicted
Chemical IdentifiersSMILES · InChI
InChI
InChI=1S/C4H8N2O3/c5-2(4(8)9)1-3(6)7/h2H,1,5H2,(H2,6,7)(H,8,9)/t2-/m0/s1
Constituent Elements
Isomers8 compounds with formula C₄H₈N₂O₃
(Z)-acetyloxymethylimino-methyl-oxidoazanium
CID 5363199 · 132.1 g/mol
3-(carbamoylamino)propanoic acid
CID 111 · 132.1 g/mol
2-[(2-aminoacetyl)amino]acetic acid
CID 11163 · 132.1 g/mol
ethyl N-methyl-N-nitrosocarbamate
CID 12001 · 132.1 g/mol
[methyl(nitroso)amino]methyl acetate
CID 42016 · 132.1 g/mol
2,4-diamino-4-oxobutanoic acid
CID 236 · 132.1 g/mol
2-[(2-azaniumylacetyl)amino]acetate
CID 1548897 · 132.1 g/mol
(2R)-2,4-diamino-4-oxobutanoic acid
CID 439600 · 132.1 g/mol