2-[2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid

• ChemBase ID: 105950
• Molecular Formular: C15H23N5O4
• Molecular Mass: 337.37422
• Monoisotopic Mass: 337.17500424
• SMILES: NC(Cc1ccc(O)cc1)C(=O)NC(CCCNC(=N)N)C(=O)O
• Canonical SMILES: NC(=N)NCCCC(C(=O)O)NC(=O)C(Cc1ccc(cc1)O)N
• InChI: InChI=1S/C15H23N5O4/c16-11(8-9-3-5-10(21)6-4-9)13(22)20-12(14(23)24)2-1-7-19-15(17)18/h3-6,11-12,21H,1-2,7-8,16H2,(H,20,22)(H,23,24)(H4,17,18,19)
• InChIKey: JXNRXNCCROJZFB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid
• IUPAC Traditional name: 2-[2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid
• Synonyms: Tyr-Arg; KYOTORPHIN

Database IDs

• CAS Number: 70904-56-2
• PubChem SID: 162092638
• PubChem CID: 2932

CALCULATED PROPERTIES

• Acid pKa: 3.5237994
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -4.7110515
• LogD (pH = 7.4): -3.0166602
• Log P: -2.4775443
• Molar Refractivity: 97.8204 cm^3
• Polarizability: 33.828503 Å^3
• Polar Surface Area: 174.55 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C

DETAILS

MP Biomedicals - 02195268

When administered intracisternally to mice, this dipeptide has about 4.2-fold more analgesic potency than met-enkephalin; it promotes the release of met-enkephalin.

REFERENCES

• Fournie-Zaluski, M.C., et al., Biochem. Biophys. Res. Commun. , 91 : 130, (1979).
• Takagi, H., et al., Nature , 282 : 410, (1979).