2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]propanamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid

• ChemBase ID: 103779
• Molecular Formular: C29H39N5O7
• Molecular Mass: 569.64926
• Monoisotopic Mass: 569.28494861
• SMILES: CC(C)CC(NC(=O)C(Cc1ccccc1)NC(=O)CNC(=O)C(C)NC(=O)C(N)Cc1ccc(O)cc1)C(=O)O
• Canonical SMILES: Oc1ccc(cc1)CC(C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)O)CC(C)C)Cc1ccccc1)C)N
• InChI: InChI=1S/C29H39N5O7/c1-17(2)13-24(29(40)41)34-28(39)23(15-19-7-5-4-6-8-19)33-25(36)16-31-26(37)18(3)32-27(38)22(30)14-20-9-11-21(35)12-10-20/h4-12,17-18,22-24,35H,13-16,30H2,1-3H3,(H,31,37)(H,32,38)(H,33,36)(H,34,39)(H,40,41)
• InChIKey: ZHUJMSMQIPIPTF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]propanamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid
• IUPAC Traditional name: 2-[2-(2-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]propanamido}acetamido)-3-phenylpropanamido]-4-methylpentanoic acid; dadle
• Synonyms: Tyr-D-Ala-Gly-Phe-Leu; [D-Ala^2,Leu^5]-ENKEPHALIN; [D-Ala2]-Leucine enkephalin

Database IDs

• CAS Number: 64963-01-5
• EC Number: 265-291-0
• MDL Number: MFCD00076409
• PubChem SID: 24894597; 162091351
• PubChem CID: 44568

CALCULATED PROPERTIES

• Acid pKa: 3.7021072
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -1.2937511
• LogD (pH = 7.4): -1.4437784
• Log P: -1.2950686
• Molar Refractivity: 150.0855 cm^3
• Polarizability: 58.771305 Å^3
• Polar Surface Area: 199.95 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - E5008

Amino Acid Sequence
Tyr-Ala-Gly-Phe-Leu
Other Notes
Potent, long-acting Leu-enkephalin analog that is resistant to enzymatic degradation

REFERENCES

• Pert, C., Science, 194: 330 (1976).