(2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid; nitric acid

• ChemBase ID: 133841
• Molecular Formular: C10H17N5O6
• Molecular Mass: 303.27188
• Monoisotopic Mass: 303.11788329
• SMILES: Cn1cncc1C[C@@H](C(=O)O)NC(=O)CCN.[N+](=O)(O)[O-]
• Canonical SMILES: [O-][N+](=O)O.NCCC(=O)N[C@H](C(=O)O)Cc1cncn1C
• InChI: InChI=1S/C10H16N4O3.HNO3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11;2-1(3)4/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17);(H,2,3,4)/t8-;/m0./s1
• InChIKey: OLWOKAYJAHHSNY-QRPNPIFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(3-aminopropanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid; nitric acid
• IUPAC Traditional name: acid, nitric; anserine
• Synonyms: Amp29-ol; Annamycinol; β-Ala-3-methyl-His nitrate salt; L-Anserine nitrate salt; β-Alanyl-3-methylhistidine 硝酸盐

Database IDs

• CAS Number: 10030-52-1
• EC Number: 233-079-7
• MDL Number: MFCD00037001
• PubChem SID: 24890509; 162228118
• PubChem CID: 112071

CALCULATED PROPERTIES

• Acid pKa: 3.4429698
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.7580523
• LogD (pH = 7.4): -4.277649
• Log P: -4.2646613
• Molar Refractivity: 60.4586 cm^3
• Polarizability: 23.294943 Å^3
• Polar Surface Area: 110.24 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338

DETAILS

Sigma Aldrich - A1131

Biochem/physiol Actions
L-Anserine s a dipeptide found in most animal tissues. In model systems it is a potent antioxidant and scavener of hydroxyl radicals. It inhibits nonenzymatic protein glycation induced by aldose and ketose reducing sugars. It is much less potent than L-carnosine as an inhibitor of protein-protein crosslinking.
Linkage
Anserine is a naturally occurring methylated analog of carnosine.

Toronto Research Chemicals - A675500

Annamycin analog.