(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-5-carbamimidamidopentanamido]-3-phenylpropanoic acid acetic acid hydrate

• ChemBase ID: 133421
• Molecular Formular: C44H62N10O12S
• Molecular Mass: 955.08788
• Monoisotopic Mass: 954.42693847
• SMILES: CC(=O)O.CSCC[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1ccccc1)C(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N.O
• Canonical SMILES: CC(=O)O.CSCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1ccccc1)CCCNC(=N)N)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N.O
• InChI: InChI=1S/C42H56N10O9S.C2H4O2.H2O/c1-62-20-18-32(39(58)50-31(13-8-19-46-42(44)45)38(57)52-34(41(60)61)23-27-11-6-3-7-12-27)51-40(59)33(22-26-9-4-2-5-10-26)49-36(55)25-47-35(54)24-48-37(56)30(43)21-28-14-16-29(53)17-15-28;1-2(3)4;/h2-7,9-12,14-17,30-34,53H,8,13,18-25,43H2,1H3,(H,47,54)(H,48,56)(H,49,55)(H,50,58)(H,51,59)(H,52,57)(H,60,61)(H4,44,45,46);1H3,(H,3,4);1H2/t30-,31-,32-,33-,34-;;/m0../s1
• InChIKey: WOWLRTTTXHINBL-AVEXNAMASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-5-carbamimidamidopentanamido]-3-phenylpropanoic acid acetic acid hydrate
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanamido]-5-carbamimidamidopentanamido]-3-phenylpropanoic acid acetic acid hydrate
• Synonyms: MERF; Tyr-Gly-Gly-Phe-Met-Arg-Phe; Methionine Enkephalin-Arg-Phe acetate salt hydrate

Database IDs

• MDL Number: MFCD11044450
• PubChem SID: 162227698
• PubChem CID: 71308667

CALCULATED PROPERTIES

• Acid pKa: 3.5040922
• H Acceptors: 13
• H Donor: 12
• LogD (pH = 5.5): -4.3504725
• LogD (pH = 7.4): -2.676154
• Log P: -2.3151624
• Molar Refractivity: 241.6463 cm^3
• Polarizability: 89.78273 Å^3
• Polar Surface Area: 320.05 Å^2
• Rotatable Bonds: 26
• 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% (HPLC)

DETAILS

Sigma Aldrich - E5757

Biochem/physiol Actions
Endogenous opioid heptapeptide that is an agonist at μ, δ, and κ receptors; also binds to σ2 receptors.