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CHEBI:7445 - nafarelin

Default Structure
ChEBI IDCHEBI:7445
ChEBI Namenafarelin
Stars
DefinitionAn 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.
Last Modified19 January 2021
DownloadsMolfile
FormulaC66H83N17O13
Net Charge0
Average Mass1322.496
Monoisotopic Mass1321.63563
SMILESCC(C)C[C@H](NC(=O)[C@@H](Cc1ccc2ccccc2c1)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1cnc2ccccc12)NC(=O)[C@H](Cc1cncn1)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
InChIInChI=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
InChIKeyRWHUEXWOYVBUCI-ITQXDASVSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
gonadotropin releasing hormone agonist  Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response.
Applications:
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.
gonadotropin releasing hormone agonist  Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
nafarelinWHO MedNet
nafarelinaWHO MedNet
nafarélineWHO MedNet
nafarelinumWHO MedNet
Synonyms  Source
5-oxo-L-prolyl L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-3-(2-naphthyl)-D-alanyl-L-leucyl-L-arginyl-L-prolylglycinamideChEBI
[6-D-(2-naphthyl)alanine]-GnRHChEBI
L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-3-(2-naphthyl)-D-alanyl-L-leucyl-L-arginyl-L-prolyl-glycinamideChEBI
Manual XrefsDatabases
10605761ChemSpider
1868DrugCentral
C07613KEGG COMPOUND
D08241KEGG DRUG
DB00666DrugBank
HMDB0014804HMDB
NafarelinWikipedia
Registry NumbersSources
CAS:76932-56-4ChemIDplus
Citations