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anserine

Structure via PubChem · Public domain (PubChem)

EntityQ415335· pop 16· linked from 13 articles

Also known as beta-alanyl-3-methyl-L-histidine, L-Anserine, (2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid, L-N-beta-Alanyl-3-methyl-Histidine, beta-Alanyl-N(pai)-methyl-L-histidine, N-b-Alanyl-3-methyl-L-Histidine, L-N-b-Alanyl-3-methyl-Histidine, N-beta-Alanyl-3-methyl-L-histidine

Anserine (β-alanyl-3-methylhistidine) is a dipeptide containing β-alanine and 3-methylhistidine. Anserine is a derivative of carnosine, which has been methylated.

Chemical data

Formula
C10H16N4O3
Molecular weight
240.26 g/mol
IUPAC name
(2S)-2-(3-aminopropanoylamino)-3-(3-methylimidazol-4-yl)propanoic acid
SMILES
CN1C=NC=C1C[C@@H](C(=O)O)NC(=O)CCN
InChIKey
MYYIAHXIVFADCU-QMMMGPOBSA-N
XLogP
-4
Polar surface area
110 Ų
H-bond donors
3
H-bond acceptors
5
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Has part
oxygen
Mass
240.12224
Show 5 more facts
chemical formula
C₁₀H₁₆N₄O₃
canonical SMILES
CN1C=NC=C1CC(C(=O)O)NC(=O)CCN
isomeric SMILES
CN1C=NC=C1C[C@@H](C(=O)O)NC(=O)CCN
Commons category
Anserine
Sources (3)

via Wikidata · CC0

~1 min read

Encyclopedic overview

5 sections
Contents
  • Biosynthesis
  • Anti-inflammatory effects
  • Metal binding
  • See also
  • References

Anserine (β-alanyl-3-methylhistidine) is a dipeptide containing β-alanine and 3-methylhistidine. Anserine is a derivative of carnosine, which has been methylated.

Anserine has biological activities similar to those of carnosine, including buffering activity, antioxidant properties, metal ion chelation, and anti-aggregation effects. Both anserine and carnosine chelate copper. Because of its methylation, anserine is more stable in serum and resistant to degradation than carnosine. Compared with carnosine, anserine have a higher antioxidant capacity.

Excerpted from Wikipedia’s “anserine” article, available under the CC BY-SA 4.0 licence.