Record Information
Version3.6
Creation Date2008-09-16 08:36:50 UTC
Update Date2013-06-10 17:20:18 UTC
HMDB IDHMDB10361
Secondary Accession NumbersNone
Metabolite Identification
Common Name(23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronide)
Description(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
Thumb
Synonyms
  1. (23S)-23,25-dihdroxy-24-oxovitamine D3 23-(beta-glucuronoside)
  2. (23S)-23,25-dihydroxy-24-oxocholecalciferol 23-(beta-glucuronide)
  3. (23S)-23,25-dihydroxy-24-oxovitamin D3 23-(beta-glucuronide)
  4. (5Z,7E)-(3S,23S)-24-oxo-9,10-seco-5,7,10(19)-cholestatriene-3,23,25-triol 23-D-glucuronide
  5. (5Z,7E)-(3S,23S)-24-oxo-9,10-seco-5,7,10(19)-cholestatriene-3,23,25-triol 23-delta-glucuronide
Chemical FormulaC33H50O10
Average Molecular Weight606.7441
Monoisotopic Molecular Weight606.34039782
IUPAC Name(2S,3S,4S,5R)-6-{[(4S,6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,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 IUPAC Name(2S,3S,4S,5R)-6-{[(4S,6R)-6-[(1R,3aS,4E,7aR)-4-{2-[(1Z,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 NumberNot Available
SMILES
C[C@H](C[C@H](OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O)C(=O)C(O)(C)C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[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)/b19-9+,20-10-/t18-,21+,22-,23+,24+,25+,26+,27-,28+,31?,33-/m1/s1
InChI KeyUSYNZBLVOOXNSN-ARRWHRBTSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassSteroids and Steroid Derivatives
Sub ClassSteroidal Glycosides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
  • Vitamin D and Derivatives
Substituents
  • 1,2 Diol
  • Acetal
  • Acyloin
  • Alpha Ketoaldehyde
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Glucuronic Acid Or Derivative
  • Glucuronide
  • Glycosyl Compound
  • Hexose Monosaccharide
  • Ketone
  • O Glycosyl Compound
  • Oxane
  • Saccharide
  • Secondary Alcohol
  • Sesterterpene
  • Sugar Acid
  • Terpene Glycoside
  • Tertiary Alcohol
Direct ParentSteroidal Glycosides
Ontology
StatusExpected and Not Quantified
Origin
  • Drug metabolite
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Waste products
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.082 g/LALOGPS
logP2.73ALOGPS
logP2.82ChemAxon
logS-3.9ALOGPS
pKa (strongest acidic)3.53ChemAxon
pKa (strongest basic)-1.3ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count10ChemAxon
hydrogen donor count6ChemAxon
polar surface area173.98ChemAxon
rotatable bond count9ChemAxon
refractivity159.37ChemAxon
polarizability66.33ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDDBMET00609
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027513
KNApSAcK IDNot Available
Chemspider ID7826573
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB10361
Metagene LinkHMDB10361
METLIN IDNot Available
PubChem Compound9547634
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Gene Name:
UGT2B4
Uniprot ID:
P06133
Gene Name:
UGT1A4
Uniprot ID:
P22310
Gene Name:
UGT2B7
Uniprot ID:
P16662
Gene Name:
UGT2B15
Uniprot ID:
P54855
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Gene Name:
UGT1A1
Uniprot ID:
P22309
Gene Name:
UGT1A9
Uniprot ID:
O60656
Gene Name:
UGT1A3
Uniprot ID:
P35503
Gene Name:
UGT2B17
Uniprot ID:
O75795
Gene Name:
UGT1A6
Uniprot ID:
P19224
Gene Name:
UGT1A5
Uniprot ID:
P35504
Gene Name:
UGT2B11
Uniprot ID:
O75310
Gene Name:
GUSB
Uniprot ID:
P08236
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Gene Name:
UGT1A10
Uniprot ID:
Q5DT02
Gene Name:
UGT1A8
Uniprot ID:
Q5DSZ6