1.0 2011-09-21 00:34:12 UTC 2025-11-19 02:44:52 UTC FDB023753 Thyrotropin-releasing factor Thyrotropin-releasing hormone (TRH), also called thyrotropin-releasing factor (TRF), thyroliberin or protirelin, is a tripeptide hormone that stimulates the release of thyroid-stimulating hormone and prolactin by the anterior pituitary. In humans, it also acts as a prolactin-releasing factor. It is also a neurotransmitter in the central nervous system. TRH is produced by the hypothalamus and travels across the median eminence to the pituitary via the hypophyseal portal system. In addition to the brain, TRH can also be detected in other areas of the body including the gastrointestinal system and pancreatic islets. Medical preparations of TRH are used in diagnostic tests of thyroid disorders and in acromegaly. [HMDB] (Pyro)-L-glutamic acid-L-histidine-L-proline-NH2 L-Pyroglutamyl-L-histidyl-L-prolinamide L-Pyroglutamyl-L-histidyl-L-proline amide Lopremone Prem Protirelin Protirelin (JP15/USAN) Relefact TRH Relefact TRH (TN) Rifathyroin Rifotironin Stimu TSH Synthetic thyrotropin-releasing factor Synthetic thyrotropin-releasing hormone Synthetic TRF Synthetic TRH Synthetic TSH-releasing factor Synthetic TSH-releasing hormone Thypinone Thyrefact Thyroid releasing hormone Thyroid-stimulating hormone-releasing factor Thyroliberin Thyrotropic hormone-releasing factor Thyrotropic hormone-releasing hormone Thyrotropic releasing hormone Thyrotropic-releasing factor Thyrotropin releasing hormone Thyrotropin-releasing factor Thyrotropin-releasing factor (8CI) Thyrotropin-releasing hormone TRF TRH TSH-releasing factor TSH-releasing hormone TSH-RF C16H22N6O4 362.3837 362.170253222 (2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide (2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(3H-imidazol-4-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide 24305-27-9 [H][C@@](CC1=CN=CN1)(NC(=O)[C@]1([H])CCC(=O)N1)C(=O)N1CCC[C@@]1([H])C(N)=O 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 XNSAINXGIQZQOO-SRVKXCTJSA-N belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Estrogens and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Estrane steroids Aliphatic homopolycyclic compounds 17-hydroxysteroids 3-oxosteroids Cyclic alcohols and derivatives Cyclic ketones Hydrocarbon derivatives Organic oxides Secondary alcohols 17-hydroxysteroid 2-oxosteroid 3-oxosteroid Alcohol Aliphatic homopolycyclic compound Carbonyl group Cyclic alcohol Cyclic ketone Estrogen-skeleton Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Secondary alcohol logp -2.32 ALOGPS logs -1.94 ALOGPS solubility 4.18e+00 g/l ALOGPS logp -3.3 ChemAxon pka_strongest_acidic 11.15 ChemAxon pka_strongest_basic 6.74 ChemAxon iupac (2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide ChemAxon average_mass 362.3837 ChemAxon mono_mass 362.170253222 ChemAxon smiles [H][C@@](CC1=CN=CN1)(NC(=O)[C@]1([H])CCC(=O)N1)C(=O)N1CCC[C@@]1([H])C(N)=O ChemAxon formula C16H22N6O4 ChemAxon inchi 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 ChemAxon inchikey XNSAINXGIQZQOO-SRVKXCTJSA-N ChemAxon polar_surface_area 150.28 ChemAxon refractivity 89.76 ChemAxon polarizability 35.13 ChemAxon rotatable_bond_count 6 ChemAxon acceptor_count 5 ChemAxon donor_count 4 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 33879 Specdb::CMs 133944 Specdb::CMs 141678 Specdb::MsMs 98070 Specdb::MsMs 98071 Specdb::MsMs 98072 Specdb::MsMs 162903 Specdb::MsMs 162904 Specdb::MsMs 162905 Specdb::MsMs 2226991 Specdb::MsMs 2227709 Specdb::MsMs 2229422 Specdb::MsMs 2230064 Specdb::MsMs 2235877 Specdb::MsMs 2237485 Specdb::MsMs 2237971 Specdb::MsMs 2239619 Specdb::MsMs 2239960 Specdb::MsMs 2241731 Specdb::MsMs 2242082 Specdb::MsMs 2243805 Specdb::MsMs 2250375 Specdb::MsMs 2251997 Specdb::MsMs 3224572 Specdb::MsMs 3224573 Specdb::MsMs 3224574 Specdb::MsMs 3224575 Specdb::MsMs 3224576 Specdb::NmrOneD 55962 Specdb::NmrOneD 55963 Specdb::NmrOneD 55964 Specdb::NmrOneD 55965 Specdb::NmrOneD 55966 Specdb::NmrOneD 55967 Specdb::NmrOneD 55968 Specdb::NmrOneD 55969 Specdb::NmrOneD 55970 Specdb::NmrOneD 55971 Specdb::NmrOneD 55972 Specdb::NmrOneD 55973 Specdb::NmrOneD 55974 Specdb::NmrOneD 55975 Specdb::NmrOneD 55976 Specdb::NmrOneD 55977 Specdb::NmrOneD 55978 Specdb::NmrOneD 55979 Specdb::NmrOneD 55980 Specdb::NmrOneD 55981 HMDB05763 35940