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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-05-09 20:53:07 UTC
Update Date2019-07-23 07:13:33 UTC
HMDB IDHMDB0060080
Secondary Accession Numbers
  • HMDB60080
Metabolite Identification
Common NameThyrotropin releasing hormone
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 drug. 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?1563866013
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
Relefact TRHKegg
ProtirelinKegg
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 FormulaC16H22N6O4
Average Molecular Weight362.3837
Monoisotopic Molecular Weight362.170253222
IUPAC Name(2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
Traditional Name(2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(3H-imidazol-4-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
CAS Registry NumberNot Available
SMILES
[H][C@@](CC1=CN=CN1)(NC(=O)[C@]1([H])CCC(=O)N1)C(=O)N1CCC[C@@]1([H])C(N)=O
InChI Identifier
InChI=1S/C16H22N6O4/c17-14(24)12-2-1-5-22(12)16(26)11(6-9-7-18-8-19-9)21-15(25)10-3-4-13(23)20-10/h7-8,10-12H,1-6H2,(H2,17,24)(H,18,19)(H,20,23)(H,21,25)/t10-,11-,12-/m0/s1
InChI KeyXNSAINXGIQZQOO-SRVKXCTJSA-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
Role

Industrial application:

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 Solubility0.12 g/LALOGPS
logP-2.3ALOGPS
logP-3.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)11.15ChemAxon
pKa (Strongest Basic)6.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.28 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.76 m³·mol⁻¹ChemAxon
Polarizability35.13 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9132000000-49fa8da4e6762d408997Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ika-2369000000-319ede954f3ced479d6eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-9582000000-bdc5d7fba5104a9bcfe8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lr-9400000000-32c92be7b84a0dc3663bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1129000000-e58ba2209f3459479f64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-6968000000-2fff001bc2b3c86f57d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9411000000-a08e549b33f1b6a81063Spectrum
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 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
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 ]