(2S)-1-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanoyl]pyrrolidine-2-carboxamide

• ChemBase ID: 131519
• Molecular Formular: C16H22N6O4
• Molecular Mass: 362.38368
• Monoisotopic Mass: 362.17025321
• SMILES: c1c(nc[nH]1)C[C@@H](C(=O)N1CCC[C@H]1C(=O)N)NC(=O)[C@@H]1CCC(=O)N1
• Canonical SMILES: O=C1CC[C@H](N1)C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N)Cc1nc[nH]c1
• 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
• InChIKey: XNSAINXGIQZQOO-SRVKXCTJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-1-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanoyl]pyrrolidine-2-carboxamide
• IUPAC Traditional name: (2S)-1-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanoyl]pyrrolidine-2-carboxamide
• Synonyms: TRF; TRH; Thyrotropin releasing hormone; L-Pyroglutamyl-L-histidyl-L-prolinamide; Thyroliberin; pGlu-His-Pro amide; L-焦谷氨酰-L-组氨酰-L-脯氨酰胺; pGlu-His-Pro 酰胺; 促甲状腺素释放素; 促甲状腺素释放激素

Database IDs

• CAS Number: 24305-27-9
• EC Number: 246-143-4
• MDL Number: MFCD00038640
• Beilstein Number: 770238
• PubChem SID: 24898185; 162225797
• PubChem CID: 638678

CALCULATED PROPERTIES

• Acid pKa: 11.153014
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.711611
• LogD (pH = 7.4): -2.9796522
• Log P: -2.929305
• Molar Refractivity: 89.1899 cm^3
• Polarizability: 34.62961 Å^3
• Polar Surface Area: 150.28 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: cell culture medium: soluble50 mL/vial; H2O: soluble10 mg/mL, clear, colorless
• Apperance: powder

Safety Information

• RTECS: TW3580000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... TRH(7200); human ... TRH(7200)mouse ... Trhr(22045)

Product Information

• Purity: ≥85% peptide basis; ≥98% (HPLC); ≥98.0% (HPLC)
• Potency: 0.3-10 ng/mL
• Suitability: cell culture tested
• Impurities: ≤5% water
• Sterility: γ-irradiated
• Empirical Formula (Hill Notation): C16H22N6O4

DETAILS

Sigma Aldrich - T9146

Amino Acid Sequence
Glp-His-Pro-NH2
Biochem/physiol Actions
促进垂体前叶生成和分泌促甲状腺素 (TSH)。
Physical form
0°C 下为粉末状；分成小份冻存，以避免使用时重复冰冻/解冻，溶液在 2-8°C 下可稳定 30 天

Sigma Aldrich - P1319

Amino Acid Sequence
Glp-His-Pro-NH2
Biochem/physiol Actions
Stimulates the production of thyrotropin (TSH) and its secretion from the anterior pituitary.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P1319.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P1319.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 83177

Amino Acid Sequence
Glp-His-Pro-NH2
Biochem/physiol Actions
Stimulates the production of thyrotropin (TSH) and its secretion from the anterior pituitary.
Other Notes
Review1; TRH and phorbol esters stimulate sphingomyelin synthesis in GH3 pituitary cells2