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CHEBI:60564 - felypressin

ChEBI IDCHEBI:60564
ChEBI Namefelypressin
Stars
DefinitionA synthetic nonapeptide comprising cysteinyl, phenylalanyl, phenylalanyl, glutaminyl, asparaginyl, cysteinyl, prolyl, lysyl, and glycinamide residues in sequence, with a disulfide bridge joining the two cysteine residues. Its antidiuretic effects are less than those of vasopressin. It is used as a vasoconstrictor in local anaesthetic injections for dental use, and is an ingredient of preparations that have been used for treatment of pain and inflammation of the mouth.
Last Modified25 April 2025
SubmitterGareth Owen
DownloadsMolfile
FormulaC46H65N13O11S2
Net Charge0
Average Mass1040.240
Monoisotopic Mass1039.43679
SMILESNCCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O
InChIInChI=1S/C46H65N13O11S2/c47-18-8-7-14-29(40(64)52-23-38(51)62)54-45(69)35-15-9-19-59(35)46(70)34-25-72-71-24-28(48)39(63)55-31(20-26-10-3-1-4-11-26)43(67)56-32(21-27-12-5-2-6-13-27)42(66)53-30(16-17-36(49)60)41(65)57-33(22-37(50)61)44(68)58-34/h1-6,10-13,28-35H,7-9,14-25,47-48H2,(H2,49,60)(H2,50,61)(H2,51,62)(H,52,64)(H,53,66)(H,54,69)(H,55,63)(H,56,67)(H,57,65)(H,58,68)/t28-,29-,30-,31-,32-,33-,34-,35-/m0/s1
InChIKeySFKQVVDKFKYTNA-DZCXQCEKSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
vasopressin receptor agonist  Any drug which binds to vasopressin receptors and triggers a response.
Applications:
vasoconstrictor agent  Drug used to cause constriction of the blood vessels.
vasopressin receptor agonist  Any drug which binds to vasopressin receptors and triggers a response.
ChEBI Ontology
Outgoing Relation(s)
felypressin (CHEBI:60564) has role vasoconstrictor agent (CHEBI:50514)
felypressin (CHEBI:60564) has role vasopressin receptor agonist (CHEBI:59727)
felypressin (CHEBI:60564) is a heterodetic cyclic peptide (CHEBI:24533)
IUPAC Name 
1-{[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13,16-dibenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-L-lysylglycinamide
INNs  Source
felypressinumChemIDplus
felipresinaChemIDplus
felypressinChemIDplus
felypressineChemIDplus
Synonyms  Source
2-(L-phenylalanine)-8-L-lysinevasopressinChemIDplus
L-cysteinyl-L-phenylalanyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-lysylglycinamide cyclic (1-6)disulfideChemIDplus
PLV-2ChEBI
Phe2-Lys8-vasopressinChEBI
Manual XrefsDatabases
DB00093DrugBank
D04137KEGG DRUG
GB928607Patent
US3232923Patent
4910DrugCentral
Registry NumbersSources
Reaxys:13260124Reaxys
CAS:56-59-7KEGG DRUG
CAS:56-59-7ChemIDplus
Citations