Showing metabocard for Thyrotropin-releasing factor (BMDB0005763)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:18:06 UTC
Update Date2020-03-13 16:39:45 UTC
BMDB IDBMDB0005763
Secondary Accession Numbers
  • BMDB05763
Metabolite Identification
Common NameThyrotropin-releasing factor
DescriptionThyrotropin releasing hormone, also known as TRH or protirelin, belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thyrotropin releasing hormone is a very strong basic compound (based on its pKa).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
Thyrotropin releasing hormoneChEBI
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 Number24305-27-9
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 estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassEstrane steroids
Direct ParentEstrogens and derivatives
Alternative Parents
Substituents
  • Estrogen-skeleton
  • 3-oxosteroid
  • Hydroxysteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • 2-oxosteroid
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Secondary alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0060080
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
References
Synthesis ReferenceMatsuda, Fuyuhiko; Itoh, Shin; Hattori, Noritaka; Yanagiya, Mitsutoshi; Matsumoto, Takeshi. A simple method for synthesis of amides and peptides through acyl chlorides. A rapid synthesis of thyrotropin releasing hormone. Tetrahedron (1985), 41(18), 3625-3
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 26S proteasome regulatory subunit 8
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
Component of the 26S proteasome, a multiprotein complex involved in the ATP-dependent degradation of ubiquitinated proteins. This complex plays a key role in the maintenance of protein homeostasis by removing misfolded or damaged proteins, which could impair cellular functions, and by removing proteins whose functions are no longer required. Therefore, the proteasome participates in numerous cellular processes, including cell cycle progression, apoptosis, or DNA damage repair. PSMC5 belongs to the heterohexameric ring of AAA (ATPases associated with diverse cellular activities) proteins that unfolds ubiquitinated target proteins that are concurrently translocated into a proteolytic chamber and degraded into peptides.
Gene Name:
PSMC5
Uniprot ID:
P62194
Molecular weight:
45626.0
Enzyme Details
2. Thyrotropin-releasing hormone receptor
General function:
Involved in thyrotropin-releasing hormone receptor acti
Specific function:
Receptor for thyrotropin-releasing hormone. This receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system.
Gene Name:
TRHR
Uniprot ID:
O46639
Molecular weight:
45165.0