Record Information
Version1.0
Creation date2011-09-21 01:25:27 UTC
Update date2015-07-21 06:59:08 UTC
Primary IDFDB027505
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name15-Hydroxynorandrostene-3,17-dione glucuronide
Description15-Hydroxynorandrostene-3,17-dione glucuronide is a natural human metabolite of 15-hydroxynorandrostene-3,17-dione 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. [HMDB]
CAS Number131749-23-0
Structure
Thumb
Synonyms
SynonymSource
15-HNADGHMDB
15-Hydroxynorandrostene-3,17-dione glucuronosideHMDB
15alpha-Hydroxynorandrost-4-ene-3,17-dione glucuronideHMDB
15alpha-Hydroxynorandrost-4-ene-3,17-dione glucuronosideHMDB
Androst-4-ene-3,17-dione, 15-hydroxy glucuronideHMDB
15 alpha-Hydroxynorandrost-4-ene-3,17-dione glucuronideHMDB
Predicted Properties
PropertyValueSource
Water Solubility1.44 g/LALOGPS
logP0.75ALOGPS
logP1.03ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.46ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.59 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity112.85 m³·mol⁻¹ChemAxon
Polarizability47.39 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H32O9
IUPAC name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2R,10R,11S,12S,15S)-15-methyl-5,14-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-12-yl]oxy}oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C24H32O9/c1-24-7-6-13-12-5-3-11(25)8-10(12)2-4-14(13)17(24)15(9-16(24)26)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h8,12-15,17-21,23,27-29H,2-7,9H2,1H3,(H,30,31)/t12-,13+,14+,15-,17+,18-,19-,20+,21-,23+,24+/m0/s1
InChI KeyADQUXZRKOKKULD-CZOXBATISA-N
Isomeric SMILES[H][C@@]12[C@H](CC(=O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H])O[C@]1([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
Average Molecular Weight464.5055
Monoisotopic Molecular Weight464.204632622
Classification
Description belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroidal glycosides
Alternative Parents
Substituents
  • Steroidal glycoside
  • Estrogen-skeleton
  • 3-oxo-delta-4-steroid
  • 3-oxosteroid
  • Estrane-skeleton
  • 17-oxosteroid
  • Oxosteroid
  • Delta-4-steroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Glycosyl compound
  • Cyclohexenone
  • Beta-hydroxy acid
  • Oxane
  • Pyran
  • Monosaccharide
  • Hydroxy acid
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Monocarboxylic acid or derivatives
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00tk-8764900000-9d1700547e803a766196JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-5350149000-63cc24f16a329c89582dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00rj-0090600000-68af45cf152f42f52e73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0190000000-16118d41aa69e2a211a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0300-0590000000-3c155876f3cb4e0de947JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03y0-1270900000-01440b9d0a4899b117a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-bc00e5c7bd83641c7737JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-3190000000-d4f1dc5c1a6ba1ab7a4eJSpectraViewer
ChemSpider ID24850124
ChEMBL IDNot Available
KEGG Compound IDC03033
Pubchem Compound ID44263360
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10353
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
UDP-glucuronosyltransferase 2B28UGT2B28Q9BY64
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B10UGT2B10P36537
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 2A3UGT2A3Q6UWM9
Beta-glucuronidaseGUSBP08236
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference