Livestock Metabolome Database: Showing metabocard for Etiocholanolone glucuronide (LMDB00777)

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

Record Information

Version

1.0

Creation Date

2016-07-30 18:17:57 UTC

Update Date

2016-08-01 19:17:23 UTC

Lmdb

LMDB00777

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Etiocholanolone glucuronide

Description

Etiocholanolone glucuronide, also known as androsterone glucosiduronate, 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, etiocholanolone glucuronide is considered to be a steroid conjugate lipid molecule. Etiocholanolone glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3alpha-Hydroxyetiocholan-17-one 3-glucosiduronic acid	ChEBI
3alpha-Hydroxyetiocholan-17-one 3-glucuronide	ChEBI
Etiocholan-3alpha-ol-17-one 3-glucuronide	ChEBI
Etiocholan-3alpha-ol-17-one 3-glucuronoside	ChEBI
3a-Hydroxyetiocholan-17-one 3-glucosiduronate	Generator
3a-Hydroxyetiocholan-17-one 3-glucosiduronic acid	Generator
3alpha-Hydroxyetiocholan-17-one 3-glucosiduronate	Generator
3Α-hydroxyetiocholan-17-one 3-glucosiduronate	Generator
3Α-hydroxyetiocholan-17-one 3-glucosiduronic acid	Generator
3a-Hydroxyetiocholan-17-one 3-glucuronide	Generator
3Α-hydroxyetiocholan-17-one 3-glucuronide	Generator
Etiocholan-3a-ol-17-one 3-glucuronide	Generator
Etiocholan-3α-ol-17-one 3-glucuronide	Generator
Etiocholan-3a-ol-17-one 3-glucuronoside	Generator
Etiocholan-3α-ol-17-one 3-glucuronoside	Generator
17-Oxoandrostan-3-yl hexopyranosiduronic acid	HMDB
3alpha-Hydroxy-5beta-androstan-17-one 3-glucuronide	HMDB
5Alpha.-androstan-3.alpha.-ol-17-one glucoronide	HMDB
5beta-Androstan-3alpha-ol-17-one 3-glucuronide	HMDB
Etiocholanolone 3-glucuronide	HMDB
Androsterone glucosiduronate	HMDB
Androsterone glucuronide	HMDB
Androsterone glucuronide, (3beta,5alpha)-isomer	HMDB
Androsterone glucuronide, (beta-D)-isomer	HMDB
Androsterone glucuronide, sodium salt, (3alpha,5alpha)-isomer	HMDB
Androsterone glucuronide, sodium salt, (3alpha,5beta)-isomer	HMDB
(3alpha,5alpha)-17-Oxoandrostan-3-yl beta-D-glucopyranosiduronic acid	HMDB

Chemical Formula

C₂₅H₃₈O₈

Average Molecular Weight

466.5644

Monoisotopic Molecular Weight

466.256668192

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

androsterone glucuronide

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13-,14+,15+,16+,18+,19+,20-,21+,23-,24+,25+/m1/s1

InChI Key

VFUIRAVTUVCQTF-SDHZCXLISA-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
Androstane-skeleton
Oxosteroid
17-oxosteroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Monosaccharide
Pyran
Oxane
Hydroxy acid
Ketone
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

steroid glucosiduronic acid (CHEBI:37451 )
Glucuronides (C11136 )
Glucuronides (LMST05010014 )

Ontology

Status

Detected but not 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	2.06	ALOGPS
logP	2.32	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.47	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	116.09 m³·mol⁻¹	ChemAxon
Polarizability	50.37 Å³	ChemAxon
Number of Rings	5	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	splash10-007a-6254900000-3224ce201f4200b35e4c	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	splash10-00r7-0190600000-3fdda78a1e92f8b5b7b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-006x-0290000000-51d6fe94f1974c92c97f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00ec-0590000000-71f03526102b61380a88	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01bi-1260900000-703dccf114629fa639b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-1290200000-1db7014540df9034a06e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-4190000000-b2d4d7c7847df524456f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000900000-a63f64862ace09c4006b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-5241900000-384ea6662fc4abc18a4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9032100000-351b0f7123639e6a7443	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000900000-80c326e64042176a4be8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fs-0792300000-a93b9d1cdd42d4c7cde2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05bb-1904000000-0daa4e3ba6eed62c511b	Spectrum