What is the molecular formula of Protirelin?

Protirelin has a molecular formula of C 16 H 22 N 6 O 4

What is the InChI Key of Protirelin molecule?

The InChI Key of Protirelin is: XNSAINXGIQZQOO-SRVKXCTJSA-N.

What is the molecular weight of Protirelin?

Protirelin presents a molecular weight of 362.384 g/mol.

Protirelin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Protirelin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

Table of Contents

1. What is Protirelin?
2. 3D Structure
3. Cartesian coordinates
4. 2D Drawing
5. Molecule descriptors
6. Physico-Chemical properties

What is the Protirelin?

The molecule Protirelin presents a molecular formula of C₁₆H₂₂N₆O₄ and its IUPAC name is (2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide.

Protirelin is a synthetic molecule that is structurally similar to the hormone thyrotropin-releasing hormone (TRH). It is used as a diagnostic tool in the evaluation of the hypothalamic-pituitary-thyroid (HPT) axis and as a research tool to study the role of TRH in various physiological processes. Protirelin has been shown to stimulate the release of thyroid-stimulating hormone (TSH) from the pituitary gland in humans and animals. This effect is thought to be mediated by the activation of TRH receptors in the pituitary. Protirelin has also been shown to stimulate the release of prolactin from the pituitary in humans. The exact mechanism by which protirelin stimulates prolactin release is not known, but it is thought to involve the activation of TRH receptors in the pituitary..

3D structure

Cartesian coordinates

Geometry of Protirelin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

Protirelin XNSAINXGIQZQOO-SRVKXCTJSA-N chemical compound 2D structure molecule svg — Protirelin

Molecule descriptors

IUPAC name	(2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
InChI code	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 Key	XNSAINXGIQZQOO-SRVKXCTJSA-N
SMILES	NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

(2S)-N-[(1S)-2-[(2S)-2-carbamoylpyrrolidino]-1-(1H-imidazol-5-ylmethyl)-2-keto-ethyl]-5-keto-pyrrolidine-2-carboxamide
(2S)-N-[(2S)-1-[(2S)-2-aminocarbonylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxidanylidene-propan-2-yl]-5-oxidanylidene-pyrrolidine-2-carboxamide
(2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
(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
(Pyro)-L-glutamic acid-L-histidine-L-proline-NH2
(S)-N-((S)-1-((S)-2-carbamoylpyrrolidin-1-yl)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)-5-oxopyrrolidine-2-carboxamide
(S)-N-((S)-1-((S)-2-carbamoylpyrrolidin-1-yl)-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl)-5-oxopyrrolidine-2-carboxamide
1-(3-(1H-Imidazol-5-yl)-2-([(5-oxo-2-pyrrolidinyl)carbonyl]amino)propanoyl)-2-pyrrolidinecarboxamide #
1-[3-(1H-4-imidazolyl)-2-(5-oxotetrahydro-1H-2-pyrrolylcarboxamido)propanoyl]tetrahydro-1H-2-pyrrolecarboxamide
11096-37-0
117217-40-0
2-Pyrrolidinecarboxamide, N-[1-[(2-Carbamoyl-1-pyrrolidinyl)carbonyl]-2-imidazol-4-ylethyl]-5-oxo-, (S,S,S)-
2-Pyrrolidinecarboxamide, N-[1-[(2-carbamoyl-1-pyrrolidinyl)carbonyl]-2-imidazol-4-ylethyl]-5-oxo-,
24305-27-9
24305-27-9 (free base)
305T279
5-Oxo-L-prolyl-L-histidyl-L-prolinamide
5-oxo-pro-his-pro-nh2
5Y5F15120W
A-38579
A858244
ABBOTT-38579
Abbott 38579
BCP12450
BDBM50072394
C03958
C74244
CCG-268193
CCRIS 2593
D00176
DB09421
DSSTox_CID_3533
DSSTox_GSID_23533
DSSTox_RID_77067
FDA 1725
GTPL2139
GTPL3836
HOLO-TRANSFERRIN
HS-2023
HY-P0002
Human Transferrin
L-Prolinamide, 5-oxo-L-prolyl-L-histidyl-
L-Pyroglutamyl-L-histidinyl-L-prolinamide
L-Pyroglutamyl-L-histidyl-L-prolinamide
L-Pyroglutamyl-L-histidyl-L-proline amide
L-Pyroglutamyl-L-histidyl-L-prolineamide
Lopremone
MFCD00038640
NCGC00160616-01
NSC 760113
NSC-760113
PR 546
PR-546
Prolinamide, 1-[N-(5-oxo-L-prolyl)-L-histidyl]-, L-
Prolinamide, 5-oxo-L-prolyl-L-histidyl-, L-
Protirelin
Protirelin (JP17/USAN/INN)
Protirelin tartrate
Protirelin, synthetic
Protirelina
Protireline
Protirelinum
PyroGlu-His-prolinamide
Q24726011
Relefact TRH
Relefact-TRH
Rifathyroin
Ro 8-6270/9
Siderophilin;partially saturated
Stimu-TSH
Synthetic TRF
Synthetic TRH
Synthetic thyrotopin releasing factor
Synthetic thyrotropin-releasing factor
Synthetic thyrotropin-releasing hormone
Synthetic tsh-releasing factor
Synthetic tsh-releasing hormone
THYREL TRH
TRANSFERRIN
TRF
TRH
TSH-RF
TSH-releasing factor
TSH-releasing hormone
Thypinone
Thyrefact
Thyroid releasing hormone
Thyroid-stimulating hormone-releasing factor
Thyroliberin
Thyroliberin;Lopremone;Synthetic TRH;Thyrotropin-releasing hormone; Rifathyroin
Thyrothropin relasing hormone
Thyrotrophic hormone releasing hormone
Thyrotrophin releasing hormone
Thyrotropic hormone-releasing factor
Thyrotropic hormone-releasing hormone
Thyrotropic releasing hormone
Thyrotropic-releasing factor
Thyrotropin releasing hormone
Thyrotropin releasing hormone, powder, gamma-irradiated, cell culture tested
Thyrotropin-ReleasingHormone
Thyrotropin-releasing factor
Thyrotropin-releasing factor (pig)
Thyrotropin-releasing hormone
[3H]-TRH
[3H]-thyrotropin-releasing hormone
[3H]TRH (human, mouse, rat)
pGlu-His-Pro-NH2
protirelin
pyroglutamyl-histidyl-prolinamide
s4680
trh-sr

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:

CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.

ZINC4096261
CAS-24305-27-9
UNII-5Y5F15120W
AKOS015994636
DTXSID0023533
CHEMBL1472
CHEBI:35940
Tox21_111939
EINECS 246-143-4
SCHEMBL33419
SCHEMBL19825647

Physico-Chemical properties

IUPAC name	(2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
Molecular formula	C₁₆H₂₂N₆O₄
Molecular weight	362.384
Melting point (ºC)
Boiling point (ºC)
Density (g/cm³)
Molar refractivity	96.85
LogP	-0.5
Topological polar surface area	150.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (K_ow) data is applied in toxicology and drug research. K_ow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(K_ow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å² are required. Thus, molecules with a polar surface area greater than 140 Å² tend to be poorly permeable to cell membranes.