CHEBI:7445 - nafarelin

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ChEBI Name nafarelin
ChEBI ID CHEBI:7445
Definition An oligopeptide comprising of 5-oxo-L-proline, L-histidine, L-tryptophan, L-serine, L-tyrosine, 3-(2-naphthyl)-D-alanine, L-leucine, L-arginine and L-prolylglycinamide residues joined sequence by peptide linkages. It is a gonadotropin releasing hormone agonist that is used to treat central precocious puberty in children and endometriosis in women.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C66H83N17O13
Net Charge 0
Average Mass 1322.496
Monoisotopic Mass 1321.63563
InChI InChI=1S/C66H83N17O13/c1-36(2)25-48(58(89)76-47(13-7-23-71-66(68)69)65(96)83-24-8-14-54(83)64(95)73-33-55(67)86)77-60(91)50(28-38-15-18-39-9-3-4-10-40(39)26-38)78-59(90)49(27-37-16-19-43(85)20-17-37)79-63(94)53(34-84)82-61(92)51(29-41-31-72-45-12-6-5-11-44(41)45)80-62(93)52(30-42-32-70-35-74-42)81-57(88)46-21-22-56(87)75-46/h3-6,9-12,15-20,26,31-32,35-36,46-54,72,84-85H,7-8,13-14,21-25,27-30,33-34H2,1-2H3,(H2,67,86)(H,70,74)(H,73,95)(H,75,87)(H,76,89)(H,77,91)(H,78,90)(H,79,94)(H,80,93)(H,81,88)(H,82,92)(H4,68,69,71)/t46-,47-,48-,49-,50+,51-,52-,53-,54-/m0/s1
InChIKey RWHUEXWOYVBUCI-ITQXDASVSA-N
SMILES CC(C)C[C@H](NC(=O)[C@@H](CC1=CC2=C(C=CC=C2)C=C1)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CNC2=C1C=CC=C2)NC(=O)[C@H](CC1=CNC=N1)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)NCC(N)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): gonadotropin releasing hormone agonist
Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response.
Application(s): gonadotropin releasing hormone agonist
Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response.
anti-estrogen
A drug which acts to reduce estrogenic activity in the body, either by reducing the amount of estrogen or by reducing the activity of whatever estrogen is present.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nafarelin (CHEBI:7445) has role anti-estrogen (CHEBI:50751)
nafarelin (CHEBI:7445) has role gonadotropin releasing hormone agonist (CHEBI:63533)
nafarelin (CHEBI:7445) is a oligopeptide (CHEBI:25676)
Incoming nafarelin acetate (CHEBI:167202) has part nafarelin (CHEBI:7445)
IUPAC Name
(2S)-N-(2-amino-2-oxoethyl)-1-{(2S,5S,8R,11S,14S,17S,20S)-2-(3-carbamimidamidopropyl)-11-(4-hydroxybenzyl)-14-(hydroxymethyl)-20-(1H-imidazol-4-ylmethyl)-17-(1H-indol-3-ylmethyl)-5-(2-methylpropyl)-8-(naphthalen-2-ylmethyl)-4,7,10,13,16,19,22-heptaoxo-22-[(2S)-5-oxopyrrolidin-2-yl]-3,6,9,12,15,18,21-heptaazadocosan-1-oyl}pyrrolidine-2-carboxamide
INNs Sources
nafarelin WHO MedNet
nafarelina WHO MedNet
nafaréline WHO MedNet
nafarelinum WHO MedNet
Synonyms Sources
5-oxo-L-prolyl L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-3-(2-naphthyl)-D-alanyl-L-leucyl-L-arginyl-L-prolylglycinamide ChEBI
[6-D-(2-naphthyl)alanine]-GnRH ChEBI
L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-3-(2-naphthyl)-D-alanyl-L-leucyl-L-arginyl-L-prolyl-glycinamide ChEBI
Manual Xrefs Databases
10605761 ChemSpider
1868 DrugCentral
C07613 KEGG COMPOUND
D08241 KEGG DRUG
DB00666 DrugBank
HMDB0014804 HMDB
Nafarelin Wikipedia
View more database links
Registry Number Type Source
76932-56-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10900577 PubMed citation Europe PMC
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Last Modified
19 January 2021