Gonadorelin (CHEM022152)

Record Information
Version1.0
Creation Date2016-05-25 18:22:01 UTC
Update Date2026-09-01 07:19:36 UTC
Accession NumberCHEM022152
Identification
Common NameGonadorelin
ClassSmall Molecule
Description
Gonadorelin is another name for gonadotropin-releasing hormone (GnRH). It is a synthetic decapeptide prepared using solid phase peptide synthesis. GnRH is responsible for the release of follicle stimulating hormone and leutinizing hormone from the anterior pituitary.
Contaminant Sources
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Gonadoliberin IKegg
GNRH-IKegg
FertagylKegg
CystorelinHMDB
GonadoliberinHMDB
KryptocurHMDB
Luteinizing hormone-releasing hormoneHMDB
FSH Releasing hormoneHMDB
FSH-Releasing hormoneHMDB
FactrelHMDB
Gonadorelin hydrochlorideHMDB
lH-Releasing hormoneHMDB
Gonadotropin releasing hormoneHMDB
LHRHHMDB
Luteinizing hormone releasing hormoneHMDB
lH-FSH Releasing hormoneHMDB
LHFSHRHHMDB
GN-RHHMDB
Gonadotropin-releasing hormoneHMDB
lH FSH Releasing hormoneHMDB
lH Releasing hormoneHMDB
LuliberinHMDB
Releasing hormone, LHFSHHMDB
GNRHHMDB
lH-RHHMDB
Gonadorelin acetateHMDB
LFRHHMDB
LHFSH Releasing hormoneHMDB
DirigestranHMDB
GonadorelinKEGG
Chemical FormulaC55H75N17O13
Average Molecular Mass1182.290 g/mol
Monoisotopic Mass1181.573 g/mol
CAS Registry Number6918-09-8
IUPAC NameN-(1-{2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl}-5-[(diaminomethylidene)amino]-1-oxopentan-2-yl)-2-{2-[2-(3-hydroxy-2-{2-[3-(1H-imidazol-5-yl)-2-[(5-oxopyrrolidin-2-yl)formamido]propanamido]-3-(1H-indol-3-yl)propanamido}propanamido)-3-(4-hydroxyphenyl)propanamido]acetamido}-4-methylpentanamide
Traditional Namegonadotropin releasing hormone
SMILESCC(C)CC(NC(=O)CNC(=O)C(CC1=CC=C(O)C=C1)NC(=O)C(CO)NC(=O)C(CC1=CNC2=CC=CC=C12)NC(=O)C(CC1=CN=CN1)NC(=O)C1CCC(=O)N1)C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(N)=O
InChI IdentifierInChI=1S/C55H75N17O13/c1-29(2)19-38(49(80)67-37(9-5-17-60-55(57)58)54(85)72-18-6-10-43(72)53(84)62-25-44(56)75)66-46(77)26-63-47(78)39(20-30-11-13-33(74)14-12-30)68-52(83)42(27-73)71-50(81)40(21-31-23-61-35-8-4-3-7-34(31)35)69-51(82)41(22-32-24-59-28-64-32)70-48(79)36-15-16-45(76)65-36/h3-4,7-8,11-14,23-24,28-29,36-43,61,73-74H,5-6,9-10,15-22,25-27H2,1-2H3,(H2,56,75)(H,59,64)(H,62,84)(H,63,78)(H,65,76)(H,66,77)(H,67,80)(H,68,83)(H,69,82)(H,70,79)(H,71,81)(H4,57,58,60)
InChI KeyXLXSAKCOAKORKW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
KingdomOrganic compounds
Super ClassOrganic Polymers
ClassPolypeptides
Sub ClassNot Available
Direct ParentPolypeptides
Alternative Parents
Substituents
  • Polypeptide
  • Alpha peptide
  • Tyrosine or derivatives
  • Phenylalanine or derivatives
  • Histidine or derivatives
  • Leucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • Triptan
  • Alpha-amino acid amide
  • Serine or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Benzenoid
  • Pyrrolidone
  • 2-pyrrolidone
  • Substituted pyrrole
  • Imidazole
  • Heteroaromatic compound
  • Pyrrolidine
  • Azole
  • Tertiary carboxylic acid amide
  • Pyrrole
  • Guanidine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Primary carboxylic acid amide
  • Lactam
  • Azacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Primary alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • Gonadotropin-releasing hormone [KO:K05252] (C07607 )
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 Solubility0.059 g/LALOGPS
logP-0.09ALOGPS
logP-6.3ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.47ChemAxon
pKa (Strongest Basic)11.16ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area474.63 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity302.51 m³·mol⁻¹ChemAxon
Polarizability121.19 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
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
External Links
DrugBank IDDB00644
HMDB IDHMDB0014782
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGonadotropin-releasing hormone
Chemspider ID33562
ChEBI IDNot Available
PubChem Compound ID36523
Kegg Compound IDC07607
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Dungan HM, Clifton DK, Steiner RA: Minireview: kisspeptin neurons as central processors in the regulation of gonadotropin-releasing hormone secretion. Endocrinology. 2006 Mar;147(3):1154-8. Epub 2005 Dec 22.
2. Franceschini I, Lomet D, Cateau M, Delsol G, Tillet Y, Caraty A: Kisspeptin immunoreactive cells of the ovine preoptic area and arcuate nucleus co-express estrogen receptor alpha. Neurosci Lett. 2006 Jul 3;401(3):225-30. Epub 2006 Apr 18.