Livestock Metabolome Database: Showing metabocard for 4-methoxyestrone (LMDB00953)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-08-04 21:13:02 UTC

Update Date

2016-08-04 22:06:18 UTC

Lmdb

LMDB00953

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-methoxyestrone

Description

Thyrotropin releasing hormone, also known as TRH or protirelin, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Thyrotropin releasing hormone is a very strong basic compound (based on its pKa). A tripeptide composed of L-pyroglutamyl, L-histidyl and L-prolinamide residues joined in sequence.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

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

Chemical Formula

C₁₉H₂₄O₃

Average Molecular Weight

300.398

Monoisotopic Molecular Weight

300.172544633

IUPAC Name

(1S,10R,11S,15R)-5-hydroxy-6-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

Traditional Name

(1S,10R,11S,15R)-5-hydroxy-6-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])C3=C(CC[C@]21[H])C(OC)=C(O)C=C3

InChI Identifier

InChI=1S/C19H24O3/c1-19-10-9-12-11-5-7-16(20)18(22-2)14(11)4-3-13(12)15(19)6-8-17(19)21/h5,7,12-13,15,20H,3-4,6,8-10H2,1-2H3/t12-,13-,15+,19-/m0/s1

InChI Key

PUEXVLNGOBYUEW-AEVLCDIHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Histidine or derivatives
N-acyl-alpha amino acid or derivatives
Proline or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
N-acylpyrrolidine
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine-2-carboxamide
Pyrrolidone
2-pyrrolidone
Azole
Imidazole
Heteroaromatic compound
Pyrrolidine
Tertiary carboxylic acid amide
Primary carboxylic acid amide
Lactam
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tripeptide (CHEBI:35940 )
peptide hormone (CHEBI:35940 )
Thyrotropin-releasing hormone [KO:K05253] (C03958 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.48	ALOGPS
logP	4.15	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	10.34	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	85.55 m³·mol⁻¹	ChemAxon
Polarizability	33.98 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fe0-0490000000-e0b809016b8c8bad412a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-08ou-1059000000-fc0f62cbcdf1d5df5108	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0029000000-d7fd1e3ab4e4be728914	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0v4i-0792000000-557e318f749c8060ba9b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pi9-5490000000-42c39c3194e527bdc751	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-0655540f59ad5c8c43a0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0090000000-5f7c58555ff69013e200	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kec-1090000000-461b8b04617809255fd7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-dd82c6133109d0e6e28e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00l2-0090000000-66e609af1e31bb237106	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kb-0090000000-fc050b7ed710552a3f97	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-0049000000-98a596f43e468044b417	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f89-5794000000-a3bbd4498b460f1ededa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-0960000000-f8b5386627dfc6028664	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected and Quantified	0.000769 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	0.0038 uM	Not Available	Bovine	21172370	details
Serum	Detected and Quantified	<0.000736 uM	Not Available	Bovine	21172370	details