Structure via PubChem · Public domain (PubChem)
Valorphin
Sign in to saveValorphin, also known as VV-hemorphin-5, is a naturally occurring, endogenous opioid heptapeptide of the hemorphin family with the amino acid sequence H-Val-Val-Tyr-Pro-Trp-Thr-Gln-OH (VVYPWTQ). It is produced in the body via proteolyic cleavage of residues 33-39 of the β-chain of hemoglobin. Valorphin binds preferentially to the μ-opioid receptor and produces effects such as analgesia and self-administration in animals. It also possesses cytotoxic and antiproliferative properties against tumor cells, the mediation of which, because they are reversed by naloxone, appears to be dependent on the
Chemical data
- Formula
- C44H61N9O11
- Molecular weight
- 892 g/mol
- IUPAC name
- (2S)-5-amino-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-3-hydroxybutanoyl]amino]-5-oxopentanoic acid
- SMILES
- C[C@H]([C@@H](C(=O)N[C@@H](CCC(=O)N)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)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N)O
- InChIKey
- VAEOIFAHJWMTKD-NMUVPRMFSA-N
- XLogP
- -1.5
- Polar surface area
- 328 Ų
- H-bond donors
- 11
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 891.4490537720001
Show 3 more facts
- isomeric SMILES
- C[C@H]([C@@H](C(=O)N[C@@H](CCC(=O)N)C(=O)O)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H]3CCCN3C(=O)[C@H](Cc4ccc(cc4)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N)O
- chemical formula
- C₄₄H₆₁N₉O₁₁
- canonical SMILES
- CC(C)C(N)C(=O)NC(C(=O)NC(Cc1ccc(O)cc1)C(=O)N1CCCC1C(=O)NC(Cc1c[nH]c2ccccc12)C(=O)NC(C(=O)NC(CCC(N)=O)C(=O)O)C(C)O)C(C)C
Sources (1)
via Wikidata · CC0
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Encyclopedic overview
2 sectionsContents
- See also
- References
Valorphin, also known as VV-hemorphin-5, is a naturally occurring, endogenous opioid heptapeptide of the hemorphin family with the amino acid sequence H-Val-Val-Tyr-Pro-Trp-Thr-Gln-OH (VVYPWTQ). It is produced in the body via proteolyic cleavage of residues 33-39 of the β-chain of hemoglobin. Valorphin binds preferentially to the μ-opioid receptor and produces effects such as analgesia and self-administration in animals. It also possesses cytotoxic and antiproliferative properties against tumor cells, the mediation of which, because they are reversed by naloxone, appears to be dependent on the opioid receptors.
== See also == Hemorphin
Excerpted from Wikipedia’s “Valorphin” article, available under the CC BY-SA 4.0 licence.