Fertirelin (CHEM020723)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 07:21:37 UTC
Update Date2026-04-06 10:56:06 UTC
Accession NumberCHEM020723
Identification
Common NameFertirelin
ClassSmall Molecule
DescriptionFertirelin, or fertirelin acetate, sold under the brand name Ovalyse, is a gonadotropin-releasing hormone agonist (GnRH agonist) which has been marketed in the United Kingdom and Austria. It may no longer be available. Fertirelin has been used in veterinary medicine. It may have been used in the treatment of sex hormone-dependent conditions and infertility in women. The drug was first introduced in 1981 in Japan to treat various kinds of ovarian failure in cattle. Fertirelin is a synthetic peptide and GnRH analogue. It is used as the acetate salt.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
9-N-Et-pronh2-LHRHMeSH
TAP 031MeSH
9-(N)-Et-pronh2-10-des-glynh2-LHRHMeSH
FertilerineMeSH
TAP-031MeSH
DesGly(10)-pro(9)-LHRH ethylamideMeSH
DGNH-LHRHMeSH
Fertilerine acetateMeSH
Fertirelin acetateMeSH
FertirelinMeSH
Chemical FormulaC55H76N16O12
Average Molecular Mass1153.313 g/mol
Monoisotopic Mass1152.583 g/mol
CAS Registry Number38234-21-8
IUPAC NameNot Available
Traditional Name(2S)-1-[(2S)-5-carbamimidamido-2-{[(2S)-2-[(2-{[(2S)-2-{[(2S)-1,3-dihydroxy-2-{[(2S)-1-hydroxy-2-{[(2S)-1-hydroxy-2-({hydroxy[(2S)-5-hydroxy-3,4-dihydro-2H-pyrrol-2-yl]methylidene}amino)-3-(3H-imidazol-4-yl)propylidene]amino}-3-(1H-indol-3-yl)propylidene]amino}propylidene]amino}-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxy-4-methylpentylidene]amino}pentanoyl]-N-ethylpyrrolidine-2-carboximidic acid
SMILES[H][C@@](CO)(N=C(O)[C@]([H])(CC1=CNC2=CC=CC=C12)N=C(O)[C@]([H])(CC1=CN=CN1)N=C(O)[C@]1([H])CCC(O)=N1)C(O)=N[C@@]([H])(CC1=CC=C(O)C=C1)C(O)=NCC(O)=N[C@@]([H])(CC(C)C)C(O)=N[C@@]([H])(CCCNC(N)=N)C(=O)N1CCC[C@@]1([H])C(O)=NCC
InChI IdentifierInChI=1S/C55H76N16O12/c1-4-59-53(82)44-12-8-20-71(44)54(83)38(11-7-19-60-55(56)57)66-49(78)39(21-30(2)3)65-46(75)27-62-47(76)40(22-31-13-15-34(73)16-14-31)67-52(81)43(28-72)70-50(79)41(23-32-25-61-36-10-6-5-9-35(32)36)68-51(80)42(24-33-26-58-29-63-33)69-48(77)37-17-18-45(74)64-37/h5-6,9-10,13-16,25-26,29-30,37-44,61,72-73H,4,7-8,11-12,17-24,27-28H2,1-3H3,(H,58,63)(H,59,82)(H,62,76)(H,64,74)(H,65,75)(H,66,78)(H,67,81)(H,68,80)(H,69,77)(H,70,79)(H4,56,57,60)/t37-,38-,39-,40-,41-,42-,43-,44-/m0/s1
InChI KeyDGCPIBPDYFLAAX-YTAGXALCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentOligopeptides
Alternative Parents
Substituents
  • Alpha-oligopeptide
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • Histidine or derivatives
  • Leucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Serine or derivatives
  • 3-alkylindole
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • Indole or derivatives
  • Indole
  • N-acylpyrrolidine
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Pyrrolidone
  • 2-pyrrolidone
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Tertiary carboxylic acid amide
  • Azole
  • Pyrrolidine
  • Heteroaromatic compound
  • Imidazole
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Guanidine
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboximidamide
  • Organoheterocyclic compound
  • Azacycle
  • Primary alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.039 g/LALOGPS
logP1.4ALOGPS
logP1.33ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)2.78ChemAxon
pKa (Strongest Basic)11.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area460.45 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity314.34 m³·mol⁻¹ChemAxon
Polarizability122.4 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00ko-9530402201-62f3a510ec14b637c1aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9120300000-33dfa1d61c776cda123bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9020100000-33609cd4b64d498d073fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kcr-5900100000-78216620bc7a69ff01c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5c-9600111001-654dc2689a346149365eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9200012021-bc9cf1d9a3da260dcc68Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkFertirelin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID188304
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available