Goserelin (CHEM022058)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:18:43 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022058
Identification
Common NameGoserelin
ClassSmall Molecule
DescriptionGoserelin is a synthetic hormone. In men, it stops the production of the hormone testosterone, which may stimulate the growth of cancer cells. In women, goserelin decreases the production of the hormone estradiol (which may stimulate the growth of cancer cells) to levels similar to a postmenopausal state. When the medication is stopped, hormone levels return to normal.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ICI-118630ZoladexHMDB
ICI 118HMDB
Goserelin acetateHMDB
Acetate, goserelinHMDB
ZoladexHMDB
(2S)-1-[(2S)-2-{[(2S)-2-{[(2R)-3-(tert-butoxy)-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-hydroxypropylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-5-carbamimidamidopentanoyl]-N-[(C-hydroxycarbonimidoyl)amino]pyrrolidine-2-carboximidateGenerator
GoserelinMeSH
Chemical FormulaC59H84N18O14
Average Molecular Mass1269.411 g/mol
Monoisotopic Mass1268.641 g/mol
CAS Registry Number65807-02-5
IUPAC Name(2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(tert-butoxy)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-5-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamido]-5-[(diaminomethylidene)amino]pentanoyl]-N-(carbamoylamino)pyrrolidine-2-carboxamide
Traditional Name(2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(tert-butoxy)-2-[(2S)-2-[(2S)-3-hydroxy-2-[(2S)-2-[(2S)-3-(3H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]propanamido]-4-methylpentanamido]-5-[(diaminomethylidene)amino]pentanoyl]-N-(carbamoylamino)pyrrolidine-2-carboxamide
SMILESCC(C)C[C@H](NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CNC2=CC=CC=C12)NC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NNC(N)=O
InChI IdentifierInChI=1S/C59H84N18O14/c1-31(2)22-40(49(82)68-39(12-8-20-64-57(60)61)56(89)77-21-9-13-46(77)55(88)75-76-58(62)90)69-54(87)45(29-91-59(3,4)5)74-50(83)41(23-32-14-16-35(79)17-15-32)70-53(86)44(28-78)73-51(84)42(24-33-26-65-37-11-7-6-10-36(33)37)71-52(85)43(25-34-27-63-30-66-34)72-48(81)38-18-19-47(80)67-38/h6-7,10-11,14-17,26-27,30-31,38-46,65,78-79H,8-9,12-13,18-25,28-29H2,1-5H3,(H,63,66)(H,67,80)(H,68,82)(H,69,87)(H,70,86)(H,71,85)(H,72,81)(H,73,84)(H,74,83)(H,75,88)(H4,60,61,64)(H3,62,76,90)/t38-,39-,40-,41-,42-,43-,44-,45+,46-/m0/s1
InChI KeyBLCLNMBMMGCOAS-URPVMXJPSA-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
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Triptan
  • Serine or derivatives
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • 3-alkylindole
  • Indole or derivatives
  • Indole
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 2-pyrrolidone
  • N-acyl-amine
  • Fatty amide
  • Benzenoid
  • Monocyclic benzene moiety
  • Substituted pyrrole
  • Fatty acyl
  • Pyrrolidone
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Hydrazinecarboxamide
  • Pyrrole
  • Tertiary carboxylic acid amide
  • Semicarbazide
  • Pyrrolidine
  • Secondary carboxylic acid amide
  • Carbonic acid derivative
  • Carboxamide group
  • Carboxylic acid hydrazide
  • Guanidine
  • Lactam
  • Carboximidamide
  • Propargyl-type 1,3-dipolar organic compound
  • Dialkyl ether
  • Ether
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Organopnictogen compound
  • 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 Solubility0.028 g/LALOGPS
logP0.3ALOGPS
logP-5.2ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.27ChemAxon
pKa (Strongest Basic)10.82ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area495.89 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity325.84 m³·mol⁻¹ChemAxon
Polarizability131.22 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-014i-0090000000-cca86889bc5dbda87a02Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-014i-0090000000-2ac55cccd457043baf43Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fl0-9282410110-4db809e164f05c461bdcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-003u-8195821130-ec7a3c13e290b40a9bf5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0089-9121200000-d2f77f54f4f6ea587de6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fv-3490000000-d769071afdc5edef7452Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abd-8590000110-4ff505f71e1a25f2732aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9000000000-ba1acae3d21095165274Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014l-2292310000-0bafe56204e9db33c9acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0lxx-6952402000-e38397ec3fc67f1e9487Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6930012244-6ab3e02292bc2a13c439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-0252900210-96bf98add412eb4f90a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0595-0540911300-8c1ea3e83288348c0c82Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btc-0620912210-e76ab43c23999a0d2425Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDDB00014
HMDB IDHMDB0014259
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGoserelin
Chemspider ID4470656
ChEBI ID775198
PubChem Compound ID5311128
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available