(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid; acetic acid

• ChemBase ID: 153415
• Molecular Formular: C17H27N5O6
• Molecular Mass: 397.42618
• Monoisotopic Mass: 397.19613361
• SMILES: CC(=O)O.c1cc(ccc1C[C@@H](C(=O)N[C@H](CCCNC(=N)N)C(=O)O)N)O
• Canonical SMILES: NC(=N)NCCC[C@H](C(=O)O)NC(=O)[C@H](Cc1ccc(cc1)O)N.CC(=O)O
• InChI: InChI=1S/C15H23N5O4.C2H4O2/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;1-2(3)4/h3-6,11-12,21H,1-2,7-8,16H2,(H,20,22)(H,23,24)(H4,17,18,19);1H3,(H,3,4)/t11-,12+;/m0./s1
• InChIKey: JSHLZRQFLJYDSZ-ZVWHLABXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid; acetic acid
• IUPAC Traditional name: (2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]-5-carbamimidamidopentanoic acid; acetic acid
• Synonyms: Tyr-D-Arg; [D-Arg2]-Kyotorphin acetate salt

Database IDs

• CAS Number: 74872-77-8
• MDL Number: MFCD00055744
• PubChem SID: 162247554
• PubChem CID: 5702203

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

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (TLC)
• Empirical Formula (Hill Notation): C15H22N5O4 · C2H4O2

DETAILS

Sigma Aldrich - K0252

Biochem/physiol Actions
Analgesic effect is six times that of kyotorphin