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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:47:44 UTC
Update Date2019-07-23 06:35:13 UTC
HMDB IDHMDB0041916
Secondary Accession Numbers
  • HMDB41916
Metabolite Identification
Common NameLeuprorelin
DescriptionLeuprorelin, also known as leuprolide or lupron, 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. Leuprorelin (INN) or Leuprorelin (USAN) is a GnRH analog. Leuprorelin is a very strong basic compound (based on its pKa).
Structure
Data?1563863713
Synonyms
ValueSource
(D-Leu(6),des-gly-NH2(10),pro-ethylamide(9))-gonadotropin-releasing hormoneChEBI
L-Pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-L-proline ethylamideChEBI
LeuprorelinaChEBI
LeuprorelineChEBI
LeuprorelinumChEBI
PGlu-his-TRP-ser-tyr-D-leu-leu-arg-pro-NHC2H5ChEBI
PGlu-his-TRP-ser-tyr-D-leu-leu-arg-pro-nhetChEBI
LeuprolideHMDB
Leuprolide acetateHMDB
Leuprorelin acetateHMDB
LupronHMDB
Monoacetate, leuprolideHMDB
TAP 144HMDB
Acetate, leuprolideHMDB
Leuprolide monoacetateHMDB
Leuprolide, (L-leu)-isomerHMDB
EnantoneHMDB
Leuprolide, (DL-leu)-isomerHMDB
TAP-144HMDB
LeuprorelinChEBI
Chemical FormulaC59H84N16O12
Average Molecular Weight1209.3983
Monoisotopic Molecular Weight1208.645462232
IUPAC Name(2S)-1-[(2S)-5-carbamimidamido-2-{[(2S)-2-{[(2R)-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-(1H-imidazol-5-yl)propylidene]amino}-3-(1H-indol-3-yl)propylidene]amino}propylidene]amino}-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}pentanoyl]-N-ethylpyrrolidine-2-carboximidic acid
Traditional Name(2S)-1-[(2S)-5-carbamimidamido-2-{[(2S)-2-{[(2R)-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-hydroxy-4-methylpentylidene]amino}-1-hydroxy-4-methylpentylidene]amino}pentanoyl]-N-ethylpyrrolidine-2-carboximidic acid
CAS Registry Number53714-56-0
SMILES
CCN=C(O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)N=C(O)[C@H](CC(C)C)N=C(O)[C@@H](CC(C)C)N=C(O)[C@H](CC1=CC=C(O)C=C1)N=C(O)[C@H](CO)N=C(O)[C@H](CC1=CNC2=CC=CC=C12)N=C(O)[C@H](CC1=CN=CN1)N=C(O)[C@@H]1CCC(O)=N1
InChI Identifier
InChI=1S/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43+,44-,45-,46-,47-,48-/m0/s1
InChI KeyGFIJNRVAKGFPGQ-LIJARHBVSA-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 Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP1.76ALOGPS
logP3.05ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.47ChemAxon
pKa (Strongest Basic)11.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area460.45 ŲChemAxon
Rotatable Bond Count32ChemAxon
Refractivity332.5 m³·mol⁻¹ChemAxon
Polarizability128.88 ųChemAxon
Number of Rings6ChemAxon
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, Positivesplash10-0006-9430312101-7177e289524c095f81d3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9010200000-4470e9b4300869c9aba6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000x-9010100000-524894e26ac9967535dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052r-2910000000-80d1dda2903210b73624Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052u-7900100000-f287f5f4860a481302faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-054o-9300001201-83727000f2c8e0daffbeSpectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID571356
KEGG Compound IDC07612
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLeuprorelin
METLIN IDNot Available
PubChem Compound657181
PDB IDNot Available
ChEBI ID6427
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Saleh FM, Niel T, Fishman MJ: Treatment of paraphilia in young adults with leuprolide acetate: a preliminary case report series. J Forensic Sci. 2004 Nov;49(6):1343-8. [PubMed:15568711 ]
  2. Geier MR, Geier DA: The potential importance of steroids in the treatment of autistic spectrum disorders and other disorders involving mercury toxicity. Med Hypotheses. 2005;64(5):946-54. [PubMed:15780490 ]
  3. Doraiswamy PM, Xiong GL: Pharmacological strategies for the prevention of Alzheimer's disease. Expert Opin Pharmacother. 2006 Jan;7(1):1-10. [PubMed:16370917 ]
  4. RxMed [Link]
  5. Sequence Information [Link]