ChemFOnt: Showing chemical card for Thyrotropin releasing hormone (CFc000040543)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:42:06 UTC

Chemfont ID

CFc000040543

Molecule Identification

Common Name

Thyrotropin releasing hormone

Definition

This compound belongs to the family of N-acyl-alpha Amino Acids and Derivatives. These are compounds containing an alpha amino acid which bears an acyl group at his terminal nitrogen atom.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
L-Pyroglutamyl-L-histidyl-L-prolineamide	ChEBI
Thyroliberin	ChEBI
Thyrotropic releasing hormone	ChEBI
Thyrotropic-releasing factor	ChEBI
Thyrotropin-releasing factor	ChEBI
TRH	ChEBI
TSH-Releasing factor	ChEBI
TSH-Releasing hormone	ChEBI
Protirelin	Kegg
Relefact TRH	Kegg
Abbott brand OF protirelin	HMDB
Abbott-38579	HMDB
Antepan	HMDB
Aventis brand OF protirelin	HMDB
Novartis brand OF protirelin	HMDB
Proterelin tartrate	HMDB
Proterelin tartrate hydrate	HMDB
Protirelin abbott brand	HMDB
Protirelin aventis brand	HMDB
Stimu TSH	HMDB
Tartrate hydrate, proterelin	HMDB
Thypinone	HMDB
Abbott 38579	HMDB
Protirelin tartrate (1:1)	HMDB
TRH Ferring	HMDB
TRH Prem	HMDB
Thyrotropin-releasing hormone	HMDB
Thyrotropin-releasing hormone tartrate	HMDB
Abbott38579	HMDB
Ferring brand OF protirelin	HMDB
Henning berlin brand OF protirelin	HMDB
Hydrate, proterelin tartrate	HMDB
Merck brand OF protirelin	HMDB
Prem, TRH	HMDB
Protirelin ferring brand	HMDB
Protirelin merck brand	HMDB
Stimu-TSH	HMDB
Thyroliberin TRH merck	HMDB
Thyrotropin releasing factor	HMDB
Protirelin novartis brand	HMDB
StimuTSH	HMDB
TRH, Relefact	HMDB
Thyrotropin releasing hormone tartrate	HMDB
Thyrotropin releasing hormone	ChEBI

Chemical Formula

C₁₆H₂₂N₆O₄

Average Molecular Weight

362.3837

Monoisotopic Molecular Weight

362.170253222

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 Number

24305-27-9

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 Key

XNSAINXGIQZQOO-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0060080)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	4.18 g/L	ALOGPS
logP	-2.3	ALOGPS
logP	-3.3	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	11.15	ChemAxon
pKa (Strongest Basic)	6.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.28 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	89.76 m³·mol⁻¹	ChemAxon
Polarizability	35.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon