Human Metabolome Database Version 3.5

Showing metabocard for Ethyl glucuronide (HMDB10325)

Record Information
Version 3.5
Creation Date 2008-09-15 10:58:31 -0600
Update Date 2013-06-10 11:02:05 -0600
HMDB ID HMDB10325
Secondary Accession Numbers None
Metabolite Identification
Common Name Ethyl glucuronide
Description Ethyl glucuronide is a natural human metabolite of Ethanol 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. beta-D-Ethyl glucuronide
  2. D-Ethyl glucuronide
  3. Ethyl beta-D-glucopyranosiduronate
  4. Ethyl beta-D-glucopyranosiduronic acid
  5. Ethylglucuronide
Chemical Formula C8H14O7
Average Molecular Weight 222.1926
Monoisotopic Molecular Weight 222.073952802
IUPAC Name (2S,3S,4S,5R,6R)-6-ethoxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional IUPAC Name (2S,3S,4S,5R,6R)-6-ethoxy-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number 17685-04-0
SMILES CCO[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier InChI=1S/C8H14O7/c1-2-14-8-5(11)3(9)4(10)6(15-8)7(12)13/h3-6,8-11H,2H2,1H3,(H,12,13)/t3-,4-,5+,6-,8+/m0/s1
InChI Key IWJBVMJWSPZNJH-UQGZVRACSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Sugar Acids and Derivatives
Sub Class Glucuronic Acid Derivatives
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • Glucuronic Acid Derivatives
  • O-glycosyl Compounds
Substituents
  • 1,2 Diol
  • Acetal
  • Beta Hydroxy Acid
  • Carboxylic Acid
  • Hexose Monosaccharide
  • Oxane
  • Secondary Alcohol
Direct Parent Glucuronides
Ontology
Status Detected and Quantified
Origin
  • Drug metabolite
  • Endogenous
Biofunction
  • Waste products
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 281 g/L ALOGPS
LogP -1.84 ALOGPS
LogP -1.6 ChemAxon
LogS 0.10 ALOGPS
pKa (strongest acidic) 3.45 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 7 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 116.45 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 45.29 ChemAxon
Polarizability 20.6 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
2.9 +/- 1.3 uM Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
26.38 +/- 15.26 umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
8.2 umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID DBMET00585 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB027477
KNApSAcK ID Not Available
Chemspider ID 19355701 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB10325 Link_out
Metagene Link HMDB10325 Link_out
METLIN ID Not Available
PubChem Compound 18392195 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References Not Available

Enzymes
Name: UDP-glucuronosyltransferase 2B4
Reactions: Not Available
Gene Name: UGT2B4
Uniprot ID: P06133 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-4
Reactions: Not Available
Gene Name: UGT1A4
Uniprot ID: P22310 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B7
Reactions: Not Available
Gene Name: UGT2B7
Uniprot ID: P16662 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B15
Reactions: Not Available
Gene Name: UGT2B15
Uniprot ID: P54855 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-1
Reactions: Not Available
Gene Name: UGT1A1
Uniprot ID: P22309 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-9
Reactions: Not Available
Gene Name: UGT1A9
Uniprot ID: O60656 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-8
Reactions: Not Available
Gene Name: UGT1A8
Uniprot ID: Q9HAW9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-3
Reactions: Not Available
Gene Name: UGT1A3
Uniprot ID: P35503 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-10
Reactions: Not Available
Gene Name: UGT1A10
Uniprot ID: Q9HAW8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 2B17
Reactions: Not Available
Gene Name: UGT2B17
Uniprot ID: O75795 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-6
Reactions: Not Available
Gene Name: UGT1A6
Uniprot ID: P19224 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: UDP-glucuronosyltransferase 1-7
Reactions: Not Available
Gene Name: UGT1A7
Uniprot ID: Q9HAW7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-glucuronidase
Reactions: Not Available
Gene Name: GUSB
Uniprot ID: P08236 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA