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Hemorphin-4
Sign in to saveHemorphin-4 is an endogenous opioid peptide of the hemorphin family which possesses antinociceptive properties and is derived from the β-chain of hemoglobin in the bloodstream. It contains a tetrapeptide core with the amino acid sequence Tyr-Pro-Trp-Thr. Hemorphin-4 serves as a opioid receptor ligand that has affinities for the μ-, δ-, and κ-opioid receptors in the same range as the structurally related β-casomorphins, although affinity to the κ-opioid receptor is markedly higher in comparison. It acts as an agonist at these sites. It presents high affinity for other receptors such as angioten
In the Vinony graph
Vinony's link graph records 760 inbound references to Hemorphin-4, and connects out to orexin, (+)-catechin and butorphanol.
It is catalogued under topics including Chembox image size set, Delta-opioid receptor agonists and Kappa-opioid receptor agonists.
Vinony links it to 5 Wikipedia language editions.
Chemical data
- Formula
- C29H35N5O7
- Molecular weight
- 565.6 g/mol
- IUPAC name
- (2S,3R)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-hydroxybutanoic acid
- SMILES
- C[C@H]([C@@H](C(=O)O)NC(=O)[C@H](CC1=CNC2=CC=CC=C21)NC(=O)[C@@H]3CCCN3C(=O)[C@H](CC4=CC=C(C=C4)O)N)O
- InChIKey
- WEGGKZQIJMQCGR-RECQUVTISA-N
- XLogP
- -1.5
- Polar surface area
- 198 Ų
- H-bond donors
- 7
- H-bond acceptors
- 8
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 565.2536484599999
Show 3 more facts
- canonical SMILES
- CC(C(C(=O)O)NC(=O)C(Cc1c[nH]c2c1cccc2)NC(=O)C3CCCN3C(=O)C(Cc4ccc(cc4)O)N)O
- chemical formula
- C₂₉H₃₅N₅O₇
- isomeric SMILES
- C[C@H]([C@@H](C(=O)O)NC(=O)[C@H](CC1=CNC2=CC=CC=C21)NC(=O)[C@@H]3CCCN3C(=O)[C@H](CC4=CC=C(C=C4)O)N)O
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Therapeutic potentials
- See also
- References
Hemorphin-4 is an endogenous opioid peptide of the hemorphin family which possesses antinociceptive properties and is derived from the β-chain of hemoglobin in the bloodstream. It contains a tetrapeptide core with the amino acid sequence Tyr-Pro-Trp-Thr. Hemorphin-4 serves as a opioid receptor ligand that has affinities for the μ-, δ-, and κ-opioid receptors in the same range as the structurally related β-casomorphins, although affinity to the κ-opioid receptor is markedly higher in comparison. It acts as an agonist at these sites. It presents high affinity for other receptors such as angiotensin IV, bombesin subtype 3 (hBRS-3), and the corticotropin releasing factor (CRF). Even though it exhibits lower binding affinity for opioid receptors relative to traditional opioid peptides such as endorphins and enkephalins; it may still influence opioid receptor systems due to its high tissue concentration.
== Therapeutic potentials == Hemorphin-4 also has inhibitory effects on angiotensin-converting enzyme (ACE), and as a result, may play a role in the regulation of blood pressure. Notably, inhibition of ACE also reduces enkephalin catabolism. Upon modifications with adamantane and cyclohexane, the Hemorphin-4 analog inhibits insulin-regulated aminopeptidase (IRAP) compared to other angiotensin IV inhibitors, making it a suitable candidate for pain, anxiety, and depression therapies. In binding to the μ-opioid receptor, it has significant seizure-suppressing and pain-relieving properties and reduces involuntary bladder contractions in a similar manner to classic opioids.
Excerpted from Wikipedia’s “Hemorphin-4” article, available under the CC BY-SA 4.0 licence.