ChemFOnt: Showing chemical card for 3,17-Androstanediol glucuronide (CFc000006329)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:17 UTC

Chemfont ID

CFc000006329

Molecule Identification

Common Name

3,17-Androstanediol glucuronide

Definition

3,17-Androstanediol glucuronide is a natural human metabolite of 3,17-Androstanediol 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
3-alpha-Androstanediol glucuronide	MeSH
Androstane-3,17-diol glucuronide, (3beta,5alpha,17beta)-isomer	MeSH
3-Hydroxyandrostan-17-yl-glucopyranosiduronic acid	MeSH
5-alpha-Androstane-3 alpha,17 beta-diol glucuronide	MeSH
Androstane-3,17-diol glucuronide, (3alpha,5beta,17beta)-isomer	MeSH
3 alpha-Diol g	MeSH
Androstane-3,17-diol glucuronide	MeSH
(1S,2S,5R,7S,10R,11S,14S,15S)-14-Hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylic acid	Generator
3,17-Androstanediol glucuronide	MeSH

Chemical Formula

C₂₅H₄₀O₈

Average Molecular Weight

468.5803

Monoisotopic Molecular Weight

468.272318256

IUPAC Name

(1S,2S,5R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

Traditional Name

(1S,2S,5R,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl (2S,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C25H40O8/c1-24-9-7-13(32-23(31)21-19(28)18(27)20(29)22(30)33-21)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-22,26-30H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,17-,18-,19-,20+,21-,22+,24-,25-/m0/s1

InChI Key

TWDCYBTXSUNASK-WGGIPMEBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
Androstane-skeleton
Hydroxysteroid
17-hydroxysteroid
Glucuronic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Monosaccharide
Oxane
Pyran
Cyclic alcohol
Hemiacetal
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Polyol
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0010321)

Cellular substructure

Organ

Liver (HMDB: HMDB0010321)
Kidney (HMDB: HMDB0010321)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010321)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0010321)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0010321)

Source

Endogenous

Endogenous (HMDB: HMDB0010321)

Animal

Animal (HMDB: HMDB0010321)

Exogenous

Food

Food (HMDB: HMDB0010321)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0010321)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0010321)

Lipid metabolism pathway (HMDB: HMDB0010321)

Cellular process

Cell signaling (HMDB: HMDB0010321)

Biochemical process

Lipid transport (HMDB: HMDB0010321)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0010321)

Molecular messenger

Signaling molecule (HMDB: HMDB0010321)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0010321)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	1.53	ALOGPS
logP	1.26	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	11.28	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	116.93 m³·mol⁻¹	ChemAxon
Polarizability	51.3 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0010321

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027473

KNApSAcK ID

Not Available

Chemspider ID

116053

KEGG Compound ID

Not Available

BioCyc ID

Beta-D-Glucuronides

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3034755

PDB ID

Not Available

ChEBI ID

172699

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3,17-Androstanediol glucuronide (CFc000006329)

MOL for CFc000006329 (3,17-Androstanediol glucuronide)

3D MOL for CFc000006329 (3,17-Androstanediol glucuronide)

3D SDF for CFc000006329 (3,17-Androstanediol glucuronide)

3D-SDF for CFc000006329 (3,17-Androstanediol glucuronide)

PDB for CFc000006329 (3,17-Androstanediol glucuronide)

3D PDB for CFc000006329 (3,17-Androstanediol glucuronide)

SMILES for CFc000006329 (3,17-Androstanediol glucuronide)

INCHI for CFc000006329 (3,17-Androstanediol glucuronide)

Structure for CFc000006329 (3,17-Androstanediol glucuronide)

3D Structure for CFc000006329 (3,17-Androstanediol glucuronide)