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

• ChemBase ID: 155358
• Molecular Formular: C27H35N5O7S
• Molecular Mass: 573.6611
• Monoisotopic Mass: 573.22571949
• SMILES: CSCC[C@@H](C(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N
• Canonical SMILES: CSCC[C@@H](C(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)CNC(=O)CNC(=O)[C@H](Cc1ccc(cc1)O)N
• InChI: InChI=1S/C27H35N5O7S/c1-40-12-11-21(27(38)39)32-26(37)22(14-17-5-3-2-4-6-17)31-24(35)16-29-23(34)15-30-25(36)20(28)13-18-7-9-19(33)10-8-18/h2-10,20-22,33H,11-16,28H2,1H3,(H,29,34)(H,30,36)(H,31,35)(H,32,37)(H,38,39)/t20-,21-,22-/m0/s1
• InChIKey: YFGBQHOOROIVKG-FKBYEOEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-(2-{2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]acetamido}acetamido)-3-phenylpropanamido]-4-(methylsulfanyl)butanoic acid
• IUPAC Traditional name: met-enkephalin
• Synonyms: Enkephalin M; [5-Methionine]Enkephalin; [Met5]Enkephalin acetate salt hydrate

Database IDs

• CAS Number: 82362-17-2
• MDL Number: MFCD00076415
• Beilstein Number: 3042295
• PubChem SID: 24897102; 162249496
• PubChem CID: 443363

CALCULATED PROPERTIES

• Acid pKa: 3.6128778
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -2.4654956
• LogD (pH = 7.4): -2.6164544
• Log P: -2.4675272
• Molar Refractivity: 149.0067 cm^3
• Polarizability: 58.17051 Å^3
• Polar Surface Area: 199.95 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: white powder

Safety Information

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

Pharmacology Properties

• Gene Information: human ... OPRD1(4985), OPRM1(4988)mouse ... OPRD1(18386), OPRM1(18390)rat ... OPRD1(24613), OPRM1(25601)

Product Information

• Purity: ≥95.0% (HPLC)
• Compostion: acetate, 2.5-20%
• Empirical Formula (Hill Notation): C27H35N5O7S · xC2H4O2 · yH2O

DETAILS

Sigma Aldrich - M6638

Amino Acid Sequence
Tyr-Gly-Gly-Phe-Met
Biochem/physiol Actions
Met-enkephalin is endogenous opioid neurotransmitter/neuromodulator with agonist activity at μ and δ opioid receptors. Enhancement of immune system function is mediated through met-enkephalin receptors on leukocytes. Met-enkephalin also functions as a growth factor on many cell types at a receptor that is distinct from the neuronal opioid receptors.