Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:53:41 UTC
Update Date2022-03-07 03:17:38 UTC
HMDB IDHMDB0060088
Secondary Accession Numbers
  • HMDB60088
Metabolite Identification
Common Name4-Methoxyestrone
DescriptionThyrotropin releasing hormone, also known as TRH or protirelin, 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. Thyrotropin releasing hormone is a very strong basic compound (based on its pKa). A tripeptide composed of L-pyroglutamyl, L-histidyl and L-prolinamide residues joined in sequence.
Structure
Data?1563866014
Synonyms
ValueSource
L-Pyroglutamyl-L-histidyl-L-prolineamideChEBI
ThyroliberinChEBI
Thyrotropic releasing hormoneChEBI
Thyrotropic-releasing factorChEBI
Thyrotropin-releasing factorChEBI
TRHChEBI
TSH-Releasing factorChEBI
TSH-Releasing hormoneChEBI
ProtirelinKegg
Relefact TRHKegg
Abbott brand OF protirelinHMDB
Abbott-38579HMDB
AntepanHMDB
Aventis brand OF protirelinHMDB
Novartis brand OF protirelinHMDB
Proterelin tartrateHMDB
Proterelin tartrate hydrateHMDB
Protirelin abbott brandHMDB
Protirelin aventis brandHMDB
Stimu TSHHMDB
Tartrate hydrate, proterelinHMDB
ThypinoneHMDB
Abbott 38579HMDB
Protirelin tartrate (1:1)HMDB
TRH FerringHMDB
TRH PremHMDB
Thyrotropin-releasing hormoneHMDB
Thyrotropin-releasing hormone tartrateHMDB
Abbott38579HMDB
Ferring brand OF protirelinHMDB
Henning berlin brand OF protirelinHMDB
Hydrate, proterelin tartrateHMDB
Merck brand OF protirelinHMDB
Prem, TRHHMDB
Protirelin ferring brandHMDB
Protirelin merck brandHMDB
Stimu-TSHHMDB
Thyroliberin TRH merckHMDB
Thyrotropin releasing factorHMDB
Protirelin novartis brandHMDB
StimuTSHHMDB
TRH, RelefactHMDB
Thyrotropin releasing hormone tartrateHMDB
Chemical FormulaC19H24O3
Average Molecular Weight300.3921
Monoisotopic Molecular Weight300.172544634
IUPAC Name(1S,10R,11S,15R)-5-hydroxy-6-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
Traditional Name(1S,10R,11S,15R)-5-hydroxy-6-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC2=C1CC[C@H]1[C@@H]3CCC(=O)[C@]3(C)CC[C@H]21
InChI Identifier
InChI=1S/C19H24O3/c1-19-10-9-12-11-5-7-16(20)18(22-2)14(11)4-3-13(12)15(19)6-8-17(19)21/h5,7,12-13,15,20H,3-4,6,8-10H2,1-2H3/t12-,13-,15+,19-/m1/s1
InChI KeyPUEXVLNGOBYUEW-PITQQHRWSA-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
  • Histidine or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Proline or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine-2-carboxamide
  • Pyrrolidone
  • 2-pyrrolidone
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Primary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0079 g/LALOGPS
logP3.48ALOGPS
logP4.15ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)10.34ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity85.55 m³·mol⁻¹ChemAxon
Polarizability33.98 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+171.64431661259
DarkChem[M-H]-170.90731661259
DeepCCS[M-2H]-210.63330932474
DeepCCS[M+Na]+186.13830932474
AllCCS[M+H]+173.932859911
AllCCS[M+H-H2O]+170.732859911
AllCCS[M+NH4]+176.932859911
AllCCS[M+Na]+177.832859911
AllCCS[M-H]-180.232859911
AllCCS[M+Na-2H]-180.032859911
AllCCS[M+HCOO]-180.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-MethoxyestroneCOC1=C(O)C=CC2=C1CC[C@H]1[C@@H]3CCC(=O)[C@]3(C)CC[C@H]213540.7Standard polar33892256
4-MethoxyestroneCOC1=C(O)C=CC2=C1CC[C@H]1[C@@H]3CCC(=O)[C@]3(C)CC[C@H]212614.8Standard non polar33892256
4-MethoxyestroneCOC1=C(O)C=CC2=C1CC[C@H]1[C@@H]3CCC(=O)[C@]3(C)CC[C@H]212737.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Methoxyestrone,1TMS,isomer #1COC1=C(O[Si](C)(C)C)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(=O)CC[C@@H]122758.3Semi standard non polar33892256
4-Methoxyestrone,1TMS,isomer #2COC1=C(O)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(O[Si](C)(C)C)=CC[C@@H]122688.6Semi standard non polar33892256
4-Methoxyestrone,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(O[Si](C)(C)C)=CC[C@@H]122663.4Semi standard non polar33892256
4-Methoxyestrone,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(O[Si](C)(C)C)=CC[C@@H]122651.6Standard non polar33892256
4-Methoxyestrone,2TMS,isomer #1COC1=C(O[Si](C)(C)C)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(O[Si](C)(C)C)=CC[C@@H]123065.0Standard polar33892256
4-Methoxyestrone,1TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(=O)CC[C@@H]123038.6Semi standard non polar33892256
4-Methoxyestrone,1TBDMS,isomer #2COC1=C(O)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]122940.0Semi standard non polar33892256
4-Methoxyestrone,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]123096.4Semi standard non polar33892256
4-Methoxyestrone,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]123008.7Standard non polar33892256
4-Methoxyestrone,2TBDMS,isomer #1COC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1CC[C@@H]1[C@@H]2CC[C@@]2(C)C(O[Si](C)(C)C(C)(C)C)=CC[C@@H]123308.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methoxyestrone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fe0-0490000000-e0b809016b8c8bad412a2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methoxyestrone GC-MS (1 TMS) - 70eV, Positivesplash10-08ou-1059000000-fc0f62cbcdf1d5df51082017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methoxyestrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methoxyestrone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 10V, Positive-QTOFsplash10-0udi-0029000000-d7fd1e3ab4e4be7289142017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 20V, Positive-QTOFsplash10-0v4i-0792000000-557e318f749c8060ba9b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 40V, Positive-QTOFsplash10-0pi9-5490000000-42c39c3194e527bdc7512017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 10V, Negative-QTOFsplash10-0002-0090000000-0655540f59ad5c8c43a02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 20V, Negative-QTOFsplash10-0002-0090000000-5f7c58555ff69013e2002017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 40V, Negative-QTOFsplash10-0kec-1090000000-461b8b04617809255fd72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 10V, Negative-QTOFsplash10-0002-0090000000-dd82c6133109d0e6e28e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 20V, Negative-QTOFsplash10-00l2-0090000000-66e609af1e31bb2371062021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 40V, Negative-QTOFsplash10-00kb-0090000000-fc050b7ed710552a3f972021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 10V, Positive-QTOFsplash10-0ue9-0049000000-98a596f43e468044b4172021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 20V, Positive-QTOFsplash10-0f89-5794000000-a3bbd4498b460f1ededa2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methoxyestrone 40V, Positive-QTOFsplash10-0f6t-0960000000-f8b5386627dfc60286642021-10-12Wishart LabView Spectrum
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 IDDB09421
Phenol Explorer Compound IDNot Available
FooDB IDFDB023753
KNApSAcK IDNot Available
Chemspider ID554166
KEGG Compound IDC03958
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProtirelin
METLIN IDNot Available
PubChem Compound638678
PDB IDNot Available
ChEBI ID35940
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.