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

• ChemBase ID: 155334
• Molecular Formular: C31H43N5O9
• Molecular Mass: 629.70122
• Monoisotopic Mass: 629.30607798
• SMILES: C[C@H](C(=O)NCC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@H](CC(C)C)C(=O)O)NC(=O)[C@H](Cc1ccc(cc1)O)N.CC(=O)O
• Canonical SMILES: Oc1ccc(cc1)C[C@@H](C(=O)N[C@@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@@H](C(=O)O)CC(C)C)Cc1ccccc1)C)N.CC(=O)O
• InChI: InChI=1S/C29H39N5O7.C2H4O2/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;1-2(3)4/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);1H3,(H,3,4)/t18-,22+,23+,24-;/m1./s1
• InChIKey: YRZBXSPTRALQEX-IIKZURRYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-[(2S)-2-{2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]acetamido}-3-phenylpropanamido]-4-methylpentanoic acid; acetic acid
• IUPAC Traditional name: acetic acid; dadle
• Synonyms: DADLE; [D-Ala2, D-Leu5]-Enkephalin acetate salt; [D-Ala2, D-Leu5]-脑啡肽 乙酸盐

Database IDs

• CAS Number: 94825-57-7
• MDL Number: MFCD00133947
• PubChem SID: 162249472
• PubChem CID: 71312121

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

Pharmacology Properties

• Gene Information: human ... OPRD1(4985)mouse ... OPRD1(18386)rat ... OPRD1(24613)

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C29H39N5O7

DETAILS

Sigma Aldrich - E7131

Amino Acid Sequence
Tyr-Ala-Gly-Phe-Leu
Biochem/physiol Actions
Prototypical δ-agonist; more potent and selective than Leu-enkephalin and Met-enkephalin; antinociceptive potency equivalent to that of β-endorphin