ChemFOnt: Showing chemical card for 16-alpha,17-beta-estriol 17-beta-D-glucuronide (CFc000006362)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:20 UTC

Chemfont ID

CFc000006362

Molecule Identification

Common Name

16-alpha,17-beta-estriol 17-beta-D-glucuronide

Definition

16-alpha,17-beta-estriol 17-beta-D-glucuronide is a natural human metabolite of 16alpha,17beta-estriol 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
16-a,17-b-Estriol 17-b-D-glucuronide	Generator
16-Α,17-β-estriol 17-β-D-glucuronide	Generator
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 17-D-glucuronide	HMDB
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 17-D-glucuronoside	HMDB
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 17-delta-glucuronide	HMDB
Estra-1,3,5(10)-triene-3,16alpha,17beta-triol 17-delta-glucuronoside	HMDB
Estriol 17beta-(beta-D-glucuronide)	HMDB
Estriol 17beta-(beta-delta-glucuronide)	HMDB
Estriol 17beta-monoglucuronide	HMDB

Chemical Formula

C₂₄H₃₂O₉

Average Molecular Weight

464.5055

Monoisotopic Molecular Weight

464.204632622

IUPAC Name

(2S,3S,4S,5R,6S)-6-{[(1S,10R,11S,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6S)-6-{[(1S,10R,11S,13R,14R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-trien-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

7219-89-8

SMILES

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

InChI Identifier

InChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)15(24)9-16(26)21(24)33-23-19(29)17(27)18(28)20(32-23)22(30)31/h3,5,8,13-21,23,25-29H,2,4,6-7,9H2,1H3,(H,30,31)/t13-,14-,15+,16-,17+,18+,19-,20+,21+,23-,24+/m1/s1

InChI Key

CZGFLAQOJPXVRV-JRSYHJKYSA-N

Chemical Taxonomy

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
Estrogen-skeleton
3-hydroxysteroid
Estrane-skeleton
Hydroxysteroid
16-alpha-hydroxysteroid
16-hydroxysteroid
1-o-glucuronide
O-glucuronide
Phenanthrene
Glucuronic acid or derivatives
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Tetralin
Beta-hydroxy acid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Oxane
Monosaccharide
Hydroxy acid
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organ

Liver (HMDB: HMDB0010354)
Kidney (HMDB: HMDB0010354)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0010354)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010354)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0010354)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0010354)

Source

Endogenous

Endogenous (HMDB: HMDB0010354)

Animal

Animal (HMDB: HMDB0010354)

Exogenous

Food

Food (HMDB: HMDB0010354)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0010354)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0010354)

Lipid metabolism pathway (HMDB: HMDB0010354)

Cellular process

Cell signaling (HMDB: HMDB0010354)

Biochemical process

Lipid transport (HMDB: HMDB0010354)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0010354)

Molecular messenger

Signaling molecule (HMDB: HMDB0010354)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0010354)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.07 g/L	ALOGPS
logP	1.01	ALOGPS
logP	1.22	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	113.55 m³·mol⁻¹	ChemAxon
Polarizability	48.84 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0010354

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027506

KNApSAcK ID

Not Available

Chemspider ID

28476727

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53480453

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 16-alpha,17-beta-estriol 17-beta-D-glucuronide (CFc000006362)

MOL for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)

3D MOL for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)

3D SDF for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)

3D-SDF for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)

PDB for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)

3D PDB for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)

SMILES for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)

INCHI for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)

Structure for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)

3D Structure for CFc000006362 (16-alpha,17-beta-estriol 17-beta-D-glucuronide)