ChemFOnt: Showing chemical card for (23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide) (CFc000006369)

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

CFc000006369

Molecule Identification

Common Name

(23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide)

Definition

(23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide) is a natural human metabolite of (23S)-23,25-dihdroxy-24-oxovitamine D3 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
(23S)-23,25-Dihydroxy-24-oxovitamine D3 23-(b-glucuronide)	Generator
(23S)-23,25-Dihydroxy-24-oxovitamine D3 23-(β-glucuronide)	Generator

Chemical Formula

C₃₃H₅₀O₁₀

Average Molecular Weight

606.7441

Monoisotopic Molecular Weight

606.34039782

IUPAC Name

(2S,3S,4S,5R)-6-{[(4S,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-octahydro-1H-inden-1-yl]-2-hydroxy-2-methyl-3-oxoheptan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R)-6-{[(4S,6R)-6-[(1R,3aS,7aR)-4-{2-[(5S)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene}-7a-methyl-hexahydro-1H-inden-1-yl]-2-hydroxy-2-methyl-3-oxoheptan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

None

SMILES

[H][C@@](C)(C[C@]([H])(OC1O[C@]([H])(C(O)=O)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O)C(=O)C(C)(C)O)[C@@]1([H])CC[C@@]2([H])C(CCC[C@]12C)=CC=C1C[C@@]([H])(O)CCC1=C

InChI Identifier

InChI=1S/C33H50O10/c1-17-8-11-21(34)16-20(17)10-9-19-7-6-14-33(5)22(12-13-23(19)33)18(2)15-24(29(38)32(3,4)41)42-31-27(37)25(35)26(36)28(43-31)30(39)40/h9-10,18,21-28,31,34-37,41H,1,6-8,11-16H2,2-5H3,(H,39,40)/t18-,21+,22-,23+,24+,25+,26+,27-,28+,31?,33-/m1/s1

InChI Key

USYNZBLVOOXNSN-FACJVLNVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-(1z-alkenyl),2-acylglycerophosphoethanolamines. These are glycerophosphoethanolamines that carry exactly one acyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one 1Z-alkenyl chain attached through an ether linkage at the O1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

1-(1Z-alkenyl),2-acylglycerophosphoethanolamines

Alternative Parents

Substituents

1-(1z-alkenyl),2-acylglycerophosphoethanolamine
Glycerol vinyl ether
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Fatty acyl
Alkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary amine
Primary aliphatic amine
Organic oxygen compound
Amine
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0010361)

Organ

Liver (HMDB: HMDB0010361)
Kidney (HMDB: HMDB0010361)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0010361)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0010361)

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

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.082 g/L	ALOGPS
logP	2.73	ALOGPS
logP	2.82	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	173.98 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	159.37 m³·mol⁻¹	ChemAxon
Polarizability	65.58 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027513

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide) (CFc000006369)

MOL for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))

3D MOL for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))

3D SDF for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))

3D-SDF for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))

PDB for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))

3D PDB for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))

SMILES for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))

INCHI for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))

Structure for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))

3D Structure for CFc000006369 ((23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide))