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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-16 08:45:43 UTC
Update Date2017-12-07 02:25:18 UTC
HMDB IDHMDB0010366
Secondary Accession Numbers
  • HMDB10366
Metabolite Identification
Common NameHyaluronan
DescriptionEtiocholanolone glucuronide is a natural human metabolite of etiocholanolone generated in the liver by UDP glucuonyltransferase. Etiocholanolone (or 5-isoandrosterone) is a metabolite of testosterone. Classified a ketosteroid, it causes fever, immunostimulation and leukocytosis. 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
ValueSource
HyaluronateHMDB
Hyaluronic acidHMDB
HylartilHMDB
Hyruan plusHMDB
LuronitHMDB
MacronanHMDB
MucoitinHMDB
Nutra-hafHMDB
Q 5AQHMDB
SepracoatHMDB
Sepragel sinusHMDB
SofastHMDB
SynviscHMDB
Acid, hyaluronicMeSH
Akorn, inc. brand OF sodium hyaluronateMeSH
Anika therapeutics brand OF sodium hyaluronidateMeSH
Hyaluronate, sodiumMeSH
amo VitraxMeSH
Bausch and lomb brand OF sodium hyaluronateMeSH
BiolonMeSH
EtamucineMeSH
HealonMeSH
AmviscMeSH
HyviscMeSH
Advanced medical optics brand OF sodium hyaluronidateMeSH
Advanced medical optics, inc. brand OF sodium hyaluronateMeSH
Hyaluronate sodiumMeSH
Sodium hyaluronateMeSH
Vitrax, amoMeSH
Chemical FormulaC28H44N2O23
Average Molecular Weight776.6486
Monoisotopic Molecular Weight776.233485724
IUPAC Name(2S,3S,4R,5R,6R)-3-{[(2S,3R,5S,6R)-4-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4R,5R,6R)-3-{[(2S,3R,5S,6R)-4-{[(2R,3R,4S,5S,6S)-6-carboxy-3,4,5-trihydroxyoxan-2-yl]oxy}-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-6-{[(2R,3R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4,5-dihydroxyoxane-2-carboxylic acid
CAS Registry Number9004-61-9
SMILES
CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@@H]1O[C@@H]([C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)C(O[C@@H]3O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@H]2NC(C)=O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C28H44N2O23/c1-5(33)29-9-18(11(35)7(3-31)47-25(9)46)49-28-17(41)15(39)20(22(53-28)24(44)45)51-26-10(30-6(2)34)19(12(36)8(4-32)48-26)50-27-16(40)13(37)14(38)21(52-27)23(42)43/h7-22,25-28,31-32,35-41,46H,3-4H2,1-2H3,(H,29,33)(H,30,34)(H,42,43)(H,44,45)/t7-,8-,9-,10-,11-,12-,13+,14+,15-,16-,17-,18?,19?,20+,21+,22+,25-,26+,27-,28-/m1/s1
InChI KeyKIUKXJAPPMFGSW-MNSSHETKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAcylaminosugars
Alternative Parents
Substituents
  • Oligosaccharide
  • Acylaminosugar
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Hydroxy acid
  • Pyran
  • Oxane
  • Acetamide
  • Carboxamide group
  • Hemiacetal
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Primary alcohol
  • Organonitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 Solubility46.6 g/LALOGPS
logP-1.8ALOGPS
logP-8.2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.87ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count14ChemAxon
Polar Surface Area399.71 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity155.1 m³·mol⁻¹ChemAxon
Polarizability70.56 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kh9-0161041900-23dbeae71feb68faba23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ul0-0393061200-98666fd29b2d88284aeeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fl0-2293030100-1541dad352da9d355ce7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-055r-2201024900-d62ed872f6e6d1ec5742View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-2262143900-e0a1be3ef6be58bedad9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fk9-5791400000-ff79477bea6365468e55View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.053 +/- 0.015 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0644 +/- 0.0528 uMNot SpecifiedNot SpecifiedNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.214 +/- 0.0992 uMNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 +/- 0.013 uMAdult (>18 years old)Both
Diabetes
details
Cerebrospinal Fluid (CSF)Detected and Quantified>10.306 uMNot SpecifiedNot SpecifiedMeningitis details
Cerebrospinal Fluid (CSF)Detected and Quantified>5.153 uMNot SpecifiedNot Specified
Colon carcinoma
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0593-0.995 uMNot SpecifiedNot SpecifiedHead injury details
Associated Disorders and Diseases
Disease References
Diabetes mellitus type 2
  1. Mine S, Okada Y, Kawahara C, Tabata T, Tanaka Y: Serum hyaluronan concentration as a marker of angiopathy in patients with diabetes mellitus. Endocr J. 2006 Dec;53(6):761-6. Epub 2006 Sep 12. [PubMed:16966827 ]
Associated OMIM IDs
DrugBank IDDB08818
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027518
KNApSAcK IDNot Available
Chemspider ID23145
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHyaluronic acid
METLIN IDNot Available
PubChem Compound24759
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 14 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Plays a role in hyaluronan/hyaluronic acid (HA) synthesis. Also able to catalyze the synthesis of chito-oligosaccharide depending on the substrate.
Gene Name:
HAS1
Uniprot ID:
Q92839
Molecular weight:
64831.425
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
Plays a role in hyaluronan/hyaluronic acid (HA) synthesis.
Gene Name:
HAS3
Uniprot ID:
O00219
Molecular weight:
62997.73
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Plays a role in hyaluronan/hyaluronic acid (HA) synthesis.
Gene Name:
HAS2
Uniprot ID:
Q92819
Molecular weight:
63565.845
General function:
Involved in ubiquitin thiolesterase activity
Specific function:
Functions in cell apoptosis. Cleaves ubiquitin fusion protein substrates. May also bind hyaluronan and RNA
Gene Name:
USP17A
Uniprot ID:
Q0WX57
Molecular weight:
59710.3

Only showing the first 10 proteins. There are 14 proteins in total.