Milk Composition Database: Showing metabocard for Estrone glucuronide (BMDB0004483)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:09:37 UTC

Update Date

2020-06-04 18:59:03 UTC

MCDB ID

BMDB0004483

Secondary Accession Numbers

BMDB04483

Metabolite Identification

Common Name

Estrone glucuronide

Description

Estrone glucuronide belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton. Thus, estrone glucuronide is considered to be a steroid conjugate lipid molecule. Estrone glucuronide exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. In cattle, estrone glucuronide is involved in the metabolic pathway called the estrone metabolism pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Estrone 3-glucosiduronic acid	ChEBI
Estrone 3-glucuronide	ChEBI
Estrone beta-D-glucuronide	ChEBI
Estrone 3-glucosiduronate	Generator
Estrone b-D-glucuronide	Generator
Estrone β-D-glucuronide	Generator
Estrone beta-delta-glucuronide	HMDB
Estrone-3-glucosiduronic acid	HMDB
Estrone-3-glucuronide	HMDB
Estrone-3-glucosiduronate	HMDB

Chemical Formula

C₂₄H₃₀O₈

Average Molecular Weight

446.4902

Monoisotopic Molecular Weight

446.194067936

IUPAC Name

(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{[(1S,10R,11S,15S)-15-methyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-5-yl]oxy}oxane-2-carboxylic acid

Traditional Name

estrone-3-glucuronide

CAS Registry Number

2479-90-5

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=CC=C(O[C@@H]4O[C@@H]([C@@H](O)[C@H](O)[C@H]4O)C(O)=O)C=C3CC[C@@]21[H]

InChI Identifier

InChI=1S/C24H30O8/c1-24-9-8-14-13-5-3-12(10-11(13)2-4-15(14)16(24)6-7-17(24)25)31-23-20(28)18(26)19(27)21(32-23)22(29)30/h3,5,10,14-16,18-21,23,26-28H,2,4,6-9H2,1H3,(H,29,30)/t14-,15-,16+,18+,19+,20-,21+,23-,24+/m1/s1

InChI Key

FJAZVHYPASAQKM-JBAURARKSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroid glucuronide conjugates

Alternative Parents

Substituents

Steroid-glucuronide-skeleton
Estrane-skeleton
17-oxosteroid
Oxosteroid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Phenanthrene
Glucuronic acid or derivatives
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Tetralin
Beta-hydroxy acid
Pyran
Fatty acyl
Oxane
Benzenoid
Monosaccharide
Hydroxy acid
Ketone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C18 steroids (estrogens) and derivatives (C11133 )
Glucuronides (C11133 )
Glucuronides (LMST05010011 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	254.5 °C	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	1.92	ALOGPS
logP	2.36	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	111.09 m³·mol⁻¹	ChemAxon
Polarizability	46.77 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-8219500000-6befcfde02b865659c65	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-0002-4222229000-9df02b5eaa81482e1d84	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-00kb-0150900000-dbbdbeaeaa0fb7b65b0c	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00kb-0150900000-78a9ec4beb4fe22a8735	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00fs-0190700000-ab622d54514a7c8dd7bb	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0390000000-0ca06f8d5f8e2266eca1	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fmi-0890000000-33ca823ccbdc77eec8b9	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kb-1252900000-1603a7df81c822d36ace	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1291100000-aea6098c09be50c7aeb7	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-3190000000-c37a96962dc8073839bc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006t-0090800000-ac0903dfe69104eaa019	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01xt-0333900000-4ad5c8540eff279f8192	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0cg0-2934000000-4ee88a34dbe6cd0e8b57	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000900000-dfac460c786c0c82c3be	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-6591800000-28870ff9517fe62979be	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-7091200000-0d8562a190cdb0c97cc6	2021-09-22	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	0.00002 +/- 0.00001 uM	PMID: 20541211	details
Detected and Quantified	0.0001 +/- 0.00002 uM	PMID: 20541211	details
Detected and Quantified	0.00002 +/- 0.00001 uM	PMID: 20541211	details
Detected and Quantified	0.00003 +/- 0.00002 uM	PMID: 20541211	details
Detected and Quantified	0.00002 +/- 0.00002 uM	PMID: 20541211	details
Detected and Quantified	0.00003 +/- 0.00001 uM	PMID: 20541211	details

External Links

HMDB ID

HMDB0004483

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021803

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

Synthesis Reference

Werschkun, Barbara; Gorziza, Karin; Thiem, Joachim. Synthesis of b-glucuronides of estradiol, ethynylestradiol and estrone. Journal of Carbohydrate Chemistry (1999), 18(6), 629-637.

Material Safety Data Sheet (MSDS)

Not Available

General References

Tso J, Aga DS: A systematic investigation to optimize simultaneous extraction and liquid chromatography tandem mass spectrometry analysis of estrogens and their conjugated metabolites in milk. J Chromatogr A. 2010 Jul 16;1217(29):4784-95. doi: 10.1016/j.chroma.2010.05.024. Epub 2010 May 25. [PubMed:20541211 ]

Showing metabocard for Estrone glucuronide (BMDB0004483)

Structure for BMDB0004483 (Estrone glucuronide)