ChemFOnt: Showing chemical card for Pregnanediol 3-O-glucuronide (CFc000006326)

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

CFc000006326

Molecule Identification

Common Name

Pregnanediol 3-O-glucuronide

Definition

Pregnanediol 3-O-glucuronide is a natural human metabolite of pregnanediol generated in the liver by UDP glucuronyltransferase. 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. Pregnanediol 3-O-glucuronide has been identified in the human placenta (PMID: 32033212 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
5 beta-Pregnane-3 alpha, 20 alpha-diol-3 alpha-glucuronide	HMDB
Pregnanediol-3 alpha-glucuronide, (3alpha,5alpha,20S)-isomer	HMDB
20 alpha-Hydroxy-5 beta-pregnan-3 alpha-yl-beta-D-glucopyranosiduronic acid	HMDB
Pregnanediol-3 alpha-glucuronide	HMDB
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}oxane-2-carboxylate	HMDB
Pregnanediol-3-glucuronide	HMDB
(3alpha,5beta,20S)-20-Hydroxypregnan-3-yl beta-D-glucopyranosiduronic acid	HMDB
(3Α,5β,20S)-20-hydroxypregnan-3-yl β-D-glucopyranosiduronic acid	HMDB
5beta-Pregnane-3alpha,20alpha-diol glucuronide	HMDB
5Β-pregnane-3α,20α-diol glucuronide	HMDB
Pregnanediol 3-glucuronide	HMDB
Pregnanediol 3alpha-monoglucuronide	HMDB
Pregnanediol 3α-monoglucuronide	HMDB
Pregnanediol-3alpha-glucuronide	HMDB
Pregnanediol-3alpha-glucuronoside	HMDB
Pregnanediol-3α-glucuronide	HMDB
Pregnanediol-3α-glucuronoside	HMDB
Pregnanediol 3-O-glucuronide	HMDB

Chemical Formula

C₂₇H₄₄O₈

Average Molecular Weight

496.6335

Monoisotopic Molecular Weight

496.303618384

IUPAC Name

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}oxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

1852-49-9

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@]1([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@H](C)O

InChI Identifier

InChI=1S/C27H44O8/c1-13(28)17-6-7-18-16-5-4-14-12-15(8-10-26(14,2)19(16)9-11-27(17,18)3)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h13-23,25,28-31H,4-12H2,1-3H3,(H,32,33)/t13-,14+,15+,16-,17+,18-,19-,20-,21-,22+,23-,25+,26-,27+/m0/s1

InChI Key

ZFFFJLDTCLJDHL-JQYCEVDMSA-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
20-hydroxysteroid
Pregnane-skeleton
Hydroxysteroid
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Glycosyl compound
O-glycosyl compound
Beta-hydroxy acid
Pyran
Oxane
Hydroxy acid
Monosaccharide
Secondary alcohol
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Carboxylic acid
Acetal
Oxacycle
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Organic oxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
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: HMDB0010318)

Cellular substructure

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 9851755)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0010318)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0010318)

Source

Endogenous

Endogenous (HMDB: HMDB0010318)

Animal

Animal (HMDB: HMDB0010318)

Exogenous

Food

Food (HMDB: HMDB0010318)

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)

Exogenous (HMDB: HMDB0010318)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0010318)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0010318)

Lipid metabolism pathway (HMDB: HMDB0010318)

Cellular process

Cell signaling (HMDB: HMDB0010318)

Biochemical process

Lipid transport (HMDB: HMDB0010318)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0010318)

Molecular messenger

Signaling molecule (HMDB: HMDB0010318)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0010318)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.35	ALOGPS
logP	2.33	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.47	ChemAxon
pKa (Strongest Basic)	-1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.22 m³·mol⁻¹	ChemAxon
Polarizability	54.34 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

HMDB0010318

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027470

KNApSAcK ID

Not Available

Chemspider ID

110346

KEGG Compound ID

C03033

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

123796

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Pregnanediol 3-O-glucuronide (CFc000006326)

MOL for CFc000006326 (Pregnanediol 3-O-glucuronide)

3D MOL for CFc000006326 (Pregnanediol 3-O-glucuronide)

3D SDF for CFc000006326 (Pregnanediol 3-O-glucuronide)

3D-SDF for CFc000006326 (Pregnanediol 3-O-glucuronide)

PDB for CFc000006326 (Pregnanediol 3-O-glucuronide)

3D PDB for CFc000006326 (Pregnanediol 3-O-glucuronide)

SMILES for CFc000006326 (Pregnanediol 3-O-glucuronide)

INCHI for CFc000006326 (Pregnanediol 3-O-glucuronide)

Structure for CFc000006326 (Pregnanediol 3-O-glucuronide)

3D Structure for CFc000006326 (Pregnanediol 3-O-glucuronide)