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CHEBI:140980 - RF9

ChEBI IDCHEBI:140980
ChEBI NameRF9
Stars
DefinitionA dipeptide formed from L-arginine and L-phenylalaninamide residues in which a hydrogen attached to the nitrogen of the α-amino group of the arginine residue has been replaced by a 1-adamantanecarbonyl group. It has been reported to be a potent and selective antagonist of neuropeptide FF (NPFF) receptors, but more recently found to be an agonist at both NPFF1R and the kisspeptin receptor (KISS1R).
Last Modified12 June 2018
SubmitterTheOtherDave
DownloadsMolfile
FormulaC26H38N6O3
Net Charge0
Average Mass482.629
Monoisotopic Mass482.30054
SMILESN=C(N)NCCC[C@H](NC(=O)C12CC3CC(CC(C3)C1)C2)C(=O)N[C@@H](Cc1ccccc1)C(N)=O
InChIInChI=1S/C26H38N6O3/c27-22(33)21(12-16-5-2-1-3-6-16)31-23(34)20(7-4-8-30-25(28)29)32-24(35)26-13-17-9-18(14-26)11-19(10-17)15-26/h1-3,5-6,17-21H,4,7-15H2,(H2,27,33)(H,31,34)(H,32,35)(H4,28,29,30)/t17?,18?,19?,20-,21-,26?/m0/s1
InChIKeyUMKHUSRDQFQHAK-RNJMTYCLSA-N
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
neuropeptide FF receptor antagonist  An antagonist that binds to and deactivates neuropeptide FF receptors.
kisspeptin receptor agonist  An agonist that acts at the kisspeptin receptor (KISS1R).
neuropeptide FF receptor agonist  An agonist that activates neuropeptide FF (NPFF) receptors.
ChEBI Ontology
Outgoing Relation(s)
RF9 (CHEBI:140980) has functional parent Arg-Ala (CHEBI:73810)
RF9 (CHEBI:140980) has role kisspeptin receptor agonist (CHEBI:141001)
RF9 (CHEBI:140980) has role neuropeptide FF receptor agonist (CHEBI:141000)
RF9 (CHEBI:140980) has role neuropeptide FF receptor antagonist (CHEBI:140982)
RF9 (CHEBI:140980) is a dipeptide (CHEBI:46761)
IUPAC Name 
N2-(tricyclo[3.3.1.13,7]decan-1-ylcarbonyl)-L-arginyl-L-phenylalaninamide
Synonyms  Source
RF 9SUBMITTER
NPFF receptor antagonistSUBMITTER
neuropeptide FF receptor antagonistSUBMITTER
RF-9ChEBI
1-adamantanecarbonyl-Arg-Phe-NH2ChEBI
Registry NumbersSources
CAS:876310-60-0SUBMITTER
Citations