Showing Compound Estriol 3-sulfate 16-glucuronide (FDB027508)

Record Information

Version

1.0

Creation date

2011-09-21 01:25:30 UTC

Update date

2015-07-21 06:59:08 UTC

Primary ID

FDB027508

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Estriol 3-sulfate 16-glucuronide

Description

Estriol 3-sulfate 16-glucuronide is a natural human metabolite of Estriol 3-sulfate generated in the liver by UDP glucuonyltransferase. Glucuronidation is used to assist in the excretion of toxic substances, drugs or other substances that cannot be used as an energy source. Glucuronic acid is attached via a glycosidic bond to the substance, and the resulting glucuronide, which has a much higher water solubility than the original substance, is eventually excreted by the kidneys. [HMDB]

CAS Number

4661-65-8

Structure

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

Synonyms

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Synonym	Source
(16alpha,17beta)-17-Hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16-yl-beta-D-glucopyranosiduronic acid	HMDB
(16alpha,17beta)-17-hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16-yl-beta-D-Glucopyranosiduronic acid	hmdb
(16alpha,17beta)-17-Hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16-yl-beta-delta-glucopyranosiduronic acid	HMDB
(16alpha,17beta)-17-hydroxy-3-(sulfooxy)estra-1,3,5(10)-trien-16-yl-beta-delta-Glucopyranosiduronic acid	hmdb
(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-13-yl]oxy}oxane-2-carboxylate	Generator
(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-13-yl]oxy}oxane-2-carboxylate	Generator
(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulphooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2,4,6-trien-13-yl]oxy}oxane-2-carboxylic acid	Generator
Estriol 3-sulfate 16-glucuronide	MeSH
Estriol 3-sulfate 16-glucuronide, (16beta,17beta)-isomer	MeSH
Estriol 3-sulfate 16-glucuronoside	HMDB

Showing 1 to 10 of 19 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.83 g/L	ALOGPS
logP	0.01	ALOGPS
logP	-0.92	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	200.28 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	123.54 m³·mol⁻¹	ChemAxon
Polarizability	54.16 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C24H32O12S

IUPAC name

(2S,3S,4S,5R)-3,4,5-trihydroxy-6-{[(1S,10R,11S,13R,14R,15S)-14-hydroxy-15-methyl-5-(sulfooxy)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-13-yl]oxy}oxane-2-carboxylic acid

InChI Identifier

InChI=1S/C24H32O12S/c1-24-7-6-13-12-5-3-11(36-37(31,32)33)8-10(12)2-4-14(13)15(24)9-16(21(24)28)34-23-19(27)17(25)18(26)20(35-23)22(29)30/h3,5,8,13-21,23,25-28H,2,4,6-7,9H2,1H3,(H,29,30)(H,31,32,33)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23?,24+/m1/s1

InChI Key

ATNWFRGUDKUYOG-SUPAOECSSA-N

Isomeric SMILES

[H][C@@]12C[C@@H](OC3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@H](O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(OS(O)(=O)=O)C=C3

Average Molecular Weight

544.569

Monoisotopic Molecular Weight

544.161447178

Classification

Description

Belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically 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

Steroidal glycosides

Alternative Parents

Substituents

Steroidal glycoside
Sulfated steroid skeleton
Estrane-skeleton
Hydroxysteroid
17-hydroxysteroid
1-o-glucuronide
O-glucuronide
Phenanthrene
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Arylsulfate
Tetralin
Beta-hydroxy acid
Hydroxy acid
Monosaccharide
Benzenoid
Sulfuric acid ester
Sulfate-ester
Oxane
Sulfuric acid monoester
Pyran
Cyclic alcohol
Organic sulfuric acid or derivatives
Secondary alcohol
Polyol
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Health effect:

Health condition:

Pregnancy

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Hepatic tissue

Organ and components:

Subcellular:

Biofluid and excreta:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Molecular messenger:

Signaling molecule

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0570-6249350000-317fea4e7b62a27fcd79	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-3339016000-1e8cf725fc89c11b2b94	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, "Estriol 3-sulfate 16-glucuronide,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Estriol 3-sulfate 16-glucuronide, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gdj-0009070000-daa124cbb6b8e2e3b51f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uy0-0159010000-937b11197960c05e4432	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uxr-0394000000-3dec314342d2e27ab531	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kg-3306490000-5cba7d5ffaec99310c8f	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-2239510000-640e9973f8698cd53bd5	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-015i-9258000000-7173317347e8b38f90ca	2016-08-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-0004290000-7f3c2c1fe22da320763b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0faj-0249440000-79fdd3e3df637d7b9f04	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1010-1449000000-608a5a907f7c557f1438	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000090000-94647094a081d0834b7c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-054n-6809470000-f3ab21d831082994a542	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014j-4109000000-6220626ca9f4cbb35b0f	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

133283

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

151223

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB10356

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Beta-glucuronidase	GUSB	P08236
UDP-glucuronosyltransferase 1-1	UGT1A1	P22309
UDP-glucuronosyltransferase 1-10	UGT1A10	Q9HAW8
UDP-glucuronosyltransferase 1-3	UGT1A3	P35503
UDP-glucuronosyltransferase 1-4	UGT1A4	P22310
UDP-glucuronosyltransferase 1-5	UGT1A5	P35504
UDP-glucuronosyltransferase 1-6	UGT1A6	P19224
UDP-glucuronosyltransferase 1-7	UGT1A7	Q9HAW7
UDP-glucuronosyltransferase 1-8	UGT1A8	Q9HAW9
UDP-glucuronosyltransferase 1-9	UGT1A9	O60656