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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:10:43 UTC
Update Date2020-02-26 21:38:00 UTC
HMDB IDHMDB0012965
Secondary Accession Numbers
  • HMDB12965
Metabolite Identification
Common NameGonadotropin releasing hormone
DescriptionGonadotropin-releasing hormone (GnRH), also known as Luteinizing-hormone releasing hormone (LHRH), is a tropic peptide hormone responsible for the release of FSH and LH from the anterior pituitary. GnRH is synthesized and released from neurons within the hypothalamus. There are differences in GNRH secretion between females and males. In males, GNRH is secreted in pulses at a constant frequency, but in females the frequency of the pulses varies during the menstrual cycle and there is a large surge of GNRH just before ovulation. Gonadotropin releasing hormone is used in the palliative treatment of advanced prostate cancer. Leuprolide is a luteinizing hormone agonist that results in suppression of testicular or follicular steroidogenesis.
Structure
Data?1582753080
Synonyms
ValueSource
(Pyro)glu-his-TRP-ser-tyr-gly-leu-arg-pro-gly-NH2HMDB
GNRHHMDB
GonadoliberinHMDB
lH-RHHMDB
Luteinizing hormone-releasing hormoneHMDB
PGlu-his-TRP-ser-tyr-gly-leu-arg-pro-gly-NH2HMDB
4-Amino-4-[(1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(2R)-5-carbamimidamido-1-[(2R)-2-{[(C-hydroxycarbonimidoyl)methyl]-C-hydroxycarbonimidoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]-C-hydroxycarbonimidoyl}-3-methylbutyl]-C-hydroxycarbonimidoyl}methyl)-C-hydroxycarbonimidoyl]-2-(4-hydroxyphenyl)ethyl]-C-hydroxycarbonimidoyl}-2-hydroxyethyl]-C-hydroxycarbonimidoyl}-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}-2-(1H-imidazol-5-yl)ethyl)-C-hydroxycarbonimidoyl]butanoateGenerator
Chemical FormulaC55H77N17O14
Average Molecular Weight1200.3054
Monoisotopic Molecular Weight1199.583590257
IUPAC Name4-amino-4-[(1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(2R)-5-carbamimidamido-1-[(2R)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(1H-imidazol-5-yl)ethyl)carbamoyl]butanoic acid
Traditional Name4-amino-4-[(1-{[(1S)-1-{[(1S)-1-{[(1S)-1-[({[(1S)-1-{[(2R)-5-carbamimidamido-1-[(2R)-2-(carbamoylmethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-hydroxyethyl]carbamoyl}-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(3H-imidazol-4-yl)ethyl)carbamoyl]butanoic acid
CAS Registry Number71447-49-9
SMILES
CC(C)C[C@H](NC(=O)CNC(=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(CC1=CN=CN1)NC(=O)C(N)CCC(O)=O)C(=O)N[C@H](CCCNC(N)=N)C(=O)N1CCC[C@@H]1C(=O)NCC(N)=O
InChI Identifier
InChI=1S/C55H77N17O14/c1-29(2)19-38(49(81)67-37(9-5-17-61-55(58)59)54(86)72-18-6-10-43(72)53(85)63-25-44(57)75)66-45(76)26-64-48(80)39(20-30-11-13-33(74)14-12-30)69-52(84)42(27-73)71-50(82)40(21-31-23-62-36-8-4-3-7-34(31)36)70-51(83)41(22-32-24-60-28-65-32)68-47(79)35(56)15-16-46(77)78/h3-4,7-8,11-14,23-24,28-29,35,37-43,62,73-74H,5-6,9-10,15-22,25-27,56H2,1-2H3,(H2,57,75)(H,60,65)(H,63,85)(H,64,80)(H,66,76)(H,67,81)(H,68,79)(H,69,84)(H,70,83)(H,71,82)(H,77,78)(H4,58,59,61)/t35?,37-,38+,39+,40+,41?,42+,43-/m1/s1
InChI KeyKTVPQHFLYINKPT-BWHZHEQWSA-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
  • Glutamic acid or derivatives
  • Leucine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • Serine or derivatives
  • Triptan
  • Alpha-amino acid amide
  • 3-alkylindole
  • N-substituted-alpha-amino acid
  • Amphetamine or derivatives
  • Alpha-amino acid or derivatives
  • Indole or derivatives
  • Indole
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Imidazolyl carboxylic acid derivative
  • N-acylpyrrolidine
  • 1-hydroxy-2-unsubstituted benzenoid
  • Amino fatty acid
  • Phenol
  • Hydroxy fatty acid
  • Substituted pyrrole
  • Fatty amide
  • Fatty acyl
  • Monocyclic benzene moiety
  • N-acyl-amine
  • Benzenoid
  • Pyrrolidine
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Azole
  • Imidazole
  • Amino acid or derivatives
  • Amino acid
  • Carboxamide group
  • Guanidine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Carboxylic acid
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Alcohol
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.036 g/LALOGPS
logP-1.6ALOGPS
logP-7.6ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)11.55ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count18ChemAxon
Polar Surface Area506.35 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity316 m³·mol⁻¹ChemAxon
Polarizability123.79 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1920100400-19d4c5e28a178fc98fbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w4r-7910400200-0c9fec4416c09b2e87d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-114i-6920201200-5247c131cf00bc40abb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0apj-2900000000-d29b1398d924ebc2a31eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ac0-8901101100-3eb34365562972d007a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9401111221-cbfe8a0f97b86d04b352Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029226
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC07612
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGonadotropin-releasing hormone
METLIN IDNot Available
PubChem Compound53481562
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available