5-Oxoprolylhistidylprolinamide
Basic information
- CAS
24305-27-9- Standard SMILES
NC(=O)C1CCCN1C(=O)C(Cc1cnc[nH]1)NC(=O)C1CCC(=O)N1- InChIKey
XNSAINXGIQZQOO-UHFFFAOYSA-N- Molecular formula
- C16H22N6O4
- Average molar mass
- 362.38 g/mol
- Monoisotopic mass
- 362.1702532
Names & identifiers
- Preferred name
- 5-Oxoprolylhistidylprolinamide
- IUPAC
- N-[1-(2-carbamoylpyrrolidin-1-yl)-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
- English name
- Thyrotropin-releasing hormone
- Molecular formula
- C16H22N6O4
- Molecular weight
- 362.38
Names & synonyms
5-oxoprolylhistidylprolinamideDTXSID30860316RefChem:1073214DTXCID70204018TRHC16H22N6O41-{3-imidazol-5-yl-2-[(5-oxopyrrolidin-2-yl)carbonylamino]propanoyl}pyrrolidin e-2-carboxamidePhe2TRHpyro-Glu-His-Pro-NH2PyroGLU-HIS-PRO AMIDESCHEMBL8364920SCHEMBL10087946
Show more names
PROTIRELINPIN2TRFTHYROTROPIN RELEASING HORMONETRH,protirelinPYR-HIS-PRO-NH2TRH (Thyrotropin Releasing Hormone)TRF1Prem
BDBM86214XNSAINXGIQZQOO-UHFFFAOYSA-NHMS3264O18HMS3755A13HMS5083I14Pharmakon1600-01506101PTR-4011-VPTR-4011
Database identifiers
- CAS
24305-27-9- PubChem CID
- 32281
- DTXSID
DTXSID30860316- Nikkaji
- J707.434D
Properties
Computed structural properties
- XLogP
- -2.5
- Topological polar surface area
- 150 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 597
Physicochemical properties
- Melting point
- 143 °C · >143°C (dec.)
- Boiling point
- 494 °C · 494°C (rough estimate)
- alpha
- -50 · -50 (D/25℃) (c=1.5, H2O)-65.5 (D) (c=1.0, H2O)
- Density
- 1.1675 · 1.1675 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- 20 °C · −20°C
- solubility
- 2 O: · H2O: 10 mg/mL, clear, colorless
- form
- powder
- pka
- 13.05 · 13.05±0.20(Predicted)
- color
- White to Off-White
- PH
- pH (10g/l, 25℃) : 3.0～4.0
- biological source
- mouse
- Water Solubility
- 25 mg/mL, · water: 25mg/mL, cloudy, colorless to faintly yellow
- Merck
- 13 · 13,9663
- BRN
- 770238 · 770238
- Sequence
- 2 · {pGlu}-His-Pro-NH2
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-21
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 2
- rtecs
- TW3580000
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
DescriptionThe first hypothalamic hypophysiotropic neurohormone identified, TRH consists of the tripeptide pGlu-His-ProNH2. It stimulates the secretion ofthyroid-stimulating hormone (TSH), prolactin (PRL), and growth hormone (GH), and also functions as a neurotransmitter and neuromodulator.
UsesThyrotropin-Releasing Hormone is a hypothalamic hypophysiotropic neuropeptide, which has the ability to stimulate the release of thyroid-stimulating hormone in mammals. It is proven that Thyrotropin-Releasing Hormone can be used to accelerate wound healing.
Usesprothyrotropin
General DescriptionThyrotropin releasing hormone (TRH) is a tripeptide hypothalamic regulatory hormone, encoded by the gene mapped to human chromosome 3q13.3-q21. TRH is expressed in a variety of organs including central nervous system (CNS) and gastrointestinal tract.
DescriptionThyrotropin Releasing Hormone Human C16H22N6O4 has a molecular mass of 362.4 Dalton.The TRH is purified by proprietary chromatographic techniques.
Additional notes
DefinitionChEBI: Protirelin is a tripeptide composed of L-pyroglutamyl, L-histidyl and L-prolinamide residues joined in sequence. It has a role as a human metabolite. It is a peptide hormone and a tripeptide.
Related reactions
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Compound notes
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