Structure via PubChem · Public domain (PubChem)
DAMGO
Sign in to saveAlso known as 2-Ala-4-mephe-5-gly-enkephalin, DAGO, glyol, Tyr-D-Ala-Gly-MePhe-Gly-ol, (D-Ala(2)-mephe(4)-gly-ol(5))enkephalin
DAMGO ([D-Ala2, N-MePhe4, Gly-ol]-enkephalin) is a synthetic opioid peptide with high μ-opioid receptor specificity. It was synthesized as a biologically stable analog of δ-opioid receptor-preferring endogenous opioids, leu- and met-enkephalin. Structures of DAMGO bound to the μ opioid receptor reveal a very similar binding pose to morphinans.
Chemical data
- Formula
- C26H35N5O6
- Molecular weight
- 513.6 g/mol
- IUPAC name
- (2S)-2-amino-N-[(2R)-1-[[2-[[(2S)-1-(2-hydroxyethylamino)-1-oxo-3-phenylpropan-2-yl]-methylamino]-2-oxoethyl]amino]-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)propanamide
- SMILES
- C[C@H](C(=O)NCC(=O)N(C)[C@@H](CC1=CC=CC=C1)C(=O)NCCO)NC(=O)[C@H](CC2=CC=C(C=C2)O)N
- InChIKey
- HPZJMUBDEAMBFI-WTNAPCKOSA-N
- XLogP
- 0.2
- Polar surface area
- 174 Ų
- H-bond donors
- 6
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
3,426 papers- DAMGO, a mu-opioid receptor selective agonist, distinguishes between mu- and delta-opioid receptors around their first extracellular loops.FEBS letters · 1995
- DAMGO recognizes four residues in the third extracellular loop to discriminate between mu- and kappa-opioid receptors.European journal of pharmacology · 1998
- DAMGO inhibits prostaglandin E2-induced potentiation of a TTX-resistant Na+ current in rat sensory neurons in vitro.Neuroscience letters · 1996
- DAMGO binding to mouse brain membranes: influence of salts, guanine nucleotides, substance P, and substance P fragments.Peptides · 1993
- DAMGO stimulates the hypothalamo-pituitary-adrenal axis through a mu-2 opioid receptor.The Journal of pharmacology and experimental therapeutics · 1993
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 513.258734
Show 3 more facts
- chemical formula
- C₂₆H₃₅N₅O₆
- canonical SMILES
- CC(C(=O)NCC(=O)N(C)C(CC1=CC=CC=C1)C(=O)NCCO)NC(=O)C(CC2=CC=C(C=C2)O)N
- isomeric SMILES
- C[C@H](C(=O)NCC(=O)N(C)[C@@H](CC1=CC=CC=C1)C(=O)NCCO)NC(=O)[C@H](CC2=CC=C(C=C2)O)N
Sources (3)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
DAMGO ([D-Ala2, N-MePhe4, Gly-ol]-enkephalin) is a synthetic opioid peptide with high μ-opioid receptor specificity. It was synthesized as a biologically stable analog of δ-opioid receptor-preferring endogenous opioids, leu- and met-enkephalin. Structures of DAMGO bound to the μ opioid receptor reveal a very similar binding pose to morphinans.
Its structure is H-Tyr-D-Ala-Gly-N-MePhe-Gly-ol.
Excerpted from Wikipedia’s “DAMGO” article, available under the CC BY-SA 4.0 licence.