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Showing metabocard for Cetrorelix (HMDB0014261)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:48 UTC
Update Date2017-12-07 02:44:37 UTC
HMDB IDHMDB0014261
Secondary Accession Numbers
  • HMDB14261
Metabolite Identification
Common NameCetrorelix
DescriptionCetrorelix is a man-made hormone that blocks the effects of Gonadotropin Releasing Hormone (GnRH). GnRH controls another hormone that is called luteinizing hormone (LH), which is the hormone that starts ovulation during the menstrual cycle. When undergoing hormone treatment sometimes premature ovulation can occur, leading to eggs that are not ready for fertilization to be released. Cetrorelix does not allow the premature release of these eggs to occur.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CetrorelixumChEBI
SB 75HMDB
SB-75HMDB
N-Acetyl-1-(3-(2-naphthyl)alanine)-2-(4-chlorophenylalanine)-3-(3-(3-pyridyl)alanine)-6-citrulline-10-alanine-LHRHMeSH
CetrotideMeSH
Cetrorelix acetateMeSH
Cetrorelix pamoateMeSH
Chemical FormulaC70H92ClN17O14
Average Molecular Weight1431.038
Monoisotopic Molecular Weight1429.669818444
IUPAC Name(2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-5-(carbamoylamino)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]pentanamido]-4-methylpentanamide
Traditional Namecetrorelix
CAS Registry Number120287-85-6
SMILES
CC(C)C[C@H](NC(=O)[C@@H](CCCNC(N)=O)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC1=CN=CC=C1)NC(=O)[C@@H](CC1=CC=C(Cl)C=C1)NC(=O)[C@@H](CC1=CC2=CC=CC=C2C=C1)NC(C)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O
InChI Identifier
InChI=1S/C70H92ClN17O14/c1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44/h5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+/m1/s1
InChI KeySBNPWPIBESPSIF-MHWMIDJBSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Leucine or derivatives
  • Proline or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Serine or derivatives
  • Alanine or derivatives
  • Naphthalene
  • N-substituted-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Amphetamine or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Chlorobenzene
  • Halobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Aryl halide
  • Fatty amide
  • Aryl chloride
  • Pyridine
  • N-acyl-amine
  • Monocyclic benzene moiety
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Heteroaromatic compound
  • Acetamide
  • Carboxamide group
  • Urea
  • Guanidine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Carbonic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboximidamide
  • Organochloride
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Imine
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organohalogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0069 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0069 g/LALOGPS
logP1.33ALOGPS
logP-1.7ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)9.49ChemAxon
pKa (Strongest Basic)11.11ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count17ChemAxon
Polar Surface Area495.67 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity384.16 m³·mol⁻¹ChemAxon
Polarizability148.09 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03du-5119702200-713925e521f82910ba30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p6-9247614220-9f57159f8b39e33cb6f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03du-9244111100-c5289fceb123c9db71eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-2009300000-fdcb67df57c3c50e2b4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0cdl-5109300001-d9e1a7fe30de34be3f74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9011010111-f8b524a667f58a9d9b4eView in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00050 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00050 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00050
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10482082
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCetrorelix
METLIN IDNot Available
PubChem Compound25074887
PDB IDNot Available
ChEBI ID59224
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lutropin-choriogonadotropic hormone receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for lutropin-choriogonadotropic hormone. The activity of this receptor is mediated by G proteins which activate adenylate cyclase
Gene Name:
LHCGR
Uniprot ID:
P22888
Molecular weight:
78642.0
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Ascoli M, Fanelli F, Segaloff DL: The lutropin/choriogonadotropin receptor, a 2002 perspective. Endocr Rev. 2002 Apr;23(2):141-74. [PubMed:11943741 ]
Enzyme Details
2. Gonadotropin-releasing hormone receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle- stimulating hormone (FSH). This receptor mediates its action by association with G-proteins that activate a phosphatidylinositol- calcium second messenger system. Isoform 2 may act as an inhibitor of GnRH-R signaling
Gene Name:
GNRHR
Uniprot ID:
P30968
Molecular weight:
37730.4
References
  1. Volker P, Grundker C, Schmidt O, Schulz KD, Emons G: Expression of receptors for luteinizing hormone-releasing hormone in human ovarian and endometrial cancers: frequency, autoregulation, and correlation with direct antiproliferative activity of luteinizing hormone-releasing hormone analogues. Am J Obstet Gynecol. 2002 Feb;186(2):171-9. [PubMed:11854630 ]
  2. Zapatero-Caballero H, Sanchez-Franco F, Guerra-Perez N, Fernandez-Mendez C, Fernandez-Vazquez G: Gonadotropin-releasing hormone receptor gene expression during pubertal development of male rats. Biol Reprod. 2003 May;68(5):1764-70. Epub 2002 Dec 11. [PubMed:12606421 ]
  3. Zapatero-Caballero H, Sanchez-Franco F, Fernandez-Mendez C, Garcia-San Frutos M, Botella-Cubells LM, Fernandez-Vazquez G: Gonadotropin-releasing hormone receptor gene expression during pubertal development of female rats. Biol Reprod. 2004 Feb;70(2):348-55. Epub 2003 Oct 15. [PubMed:14561652 ]
  4. Roth C, Hegemann F, Hildebrandt J, Balzer I, Witt A, Wuttke W, Jarry H: Pituitary and gonadal effects of GnRH (gonadotropin releasing hormone) analogues in two peripubertal female rat models. Pediatr Res. 2004 Jan;55(1):126-33. Epub 2003 Nov 6. [PubMed:14605254 ]
  5. Castellon E, Clementi M, Hitschfeld C, Sanchez C, Benitez D, Saenz L, Contreras H, Huidobro C: Effect of leuprolide and cetrorelix on cell growth, apoptosis, and GnRH receptor expression in primary cell cultures from human prostate carcinoma. Cancer Invest. 2006 Apr-May;24(3):261-8. [PubMed:16809153 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]