(2S)-2-{2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-N-methylacetamido}-N-(2-hydroxyethyl)-3-phenylpropanamide; acetic acid

• ChemBase ID: 132318
• Molecular Formular: C28H39N5O8
• Molecular Mass: 573.63796
• Monoisotopic Mass: 573.27986323
• SMILES: C[C@H](C(=O)NCC(=O)N(C)[C@@H](Cc1ccccc1)C(=O)NCCO)NC(=O)[C@H](Cc1ccc(cc1)O)N.CC(=O)O
• Canonical SMILES: CC(=O)O.OCCNC(=O)[C@@H](N(C(=O)CNC(=O)[C@H](NC(=O)[C@H](Cc1ccc(cc1)O)N)C)C)Cc1ccccc1
• InChI: InChI=1S/C26H35N5O6.C2H4O2/c1-17(30-25(36)21(27)14-19-8-10-20(33)11-9-19)24(35)29-16-23(34)31(2)22(26(37)28-12-13-32)15-18-6-4-3-5-7-18;1-2(3)4/h3-11,17,21-22,32-33H,12-16,27H2,1-2H3,(H,28,37)(H,29,35)(H,30,36);1H3,(H,3,4)/t17-,21+,22+;/m1./s1
• InChIKey: XZZYKCKUDLGXJA-NJUGUJQKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{2-[(2R)-2-[(2S)-2-amino-3-(4-hydroxyphenyl)propanamido]propanamido]-N-methylacetamido}-N-(2-hydroxyethyl)-3-phenylpropanamide; acetic acid
• IUPAC Traditional name: acetic acid; damgo
• Synonyms: DAGO; DAMGO; Tyr-D-Ala-Gly-N-methyl-Phe-Gly-ol; [D-Ala2, N-Me-Phe4, Gly5-ol]-Enkephalin acetate salt

Database IDs

• CAS Number: 100929-53-1
• MDL Number: MFCD00133215
• PubChem SID: 162226595
• PubChem CID: 5485228

CALCULATED PROPERTIES

• Acid pKa: 9.510376
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -2.9699023
• LogD (pH = 7.4): -1.2990922
• Log P: -0.93769467
• Molar Refractivity: 137.0224 cm^3
• Polarizability: 53.33679 Å^3
• Polar Surface Area: 174.09 Å^2
• Rotatable Bonds: 13
• 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 ... OPRM1(4988)mouse ... OPRM1(18390)rat ... OPRM1(25601)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - E7384

Amino Acid Sequence
Tyr-Ala-Gly-Nme-Phe-Gly-ol
Biochem/physiol Actions
Enkephalin analog that is a selective agonist at μ-opioid receptors.