Record Information
Version1.0
Creation date2011-09-21 00:35:31 UTC
Update date2015-07-21 06:57:53 UTC
Primary IDFDB023835
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name5-alpha-Dihydrotestosterone glucuronide
Description5-alpha-Dihydrotestosterone glucuronide is a natural human metabolite of 5alpha-Dihydrotestosterone 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 Number42037-24-1
Structure
Thumb
Synonyms
SynonymSource
(5alpha,17beta)-3-Oxoandrostan-17-yl beta-D-glucopyranosiduronic acidChEBI
17beta-Hydroxy-5alpha-androstan-3-one glucuronideChEBI
5alpha-Dihydrotestosterone 17-(beta-D-glucuronide)ChEBI
5alpha-Dihydrotestosterone 17-beta-glucuronideChEBI
5alpha-Dihydrotestosterone 17-O-(beta-D-glucuronic acid)ChEBI
5alpha-Dihydrotestosterone glucuronideChEBI
5alpha-Dihydrotestosterone-17gChEBI
Dihydrotestosterone 17-glucuronideChEBI
Dihydrotestosterone glucuronideChEBI
Stanolone 17-glucuronideChEBI
Stanolone glucuronateChEBI
(5a,17b)-3-Oxoandrostan-17-yl b-D-glucopyranosiduronateGenerator
(5a,17b)-3-Oxoandrostan-17-yl b-D-glucopyranosiduronic acidGenerator
(5alpha,17beta)-3-Oxoandrostan-17-yl beta-D-glucopyranosiduronateGenerator
(5Α,17β)-3-oxoandrostan-17-yl β-D-glucopyranosiduronateGenerator
(5Α,17β)-3-oxoandrostan-17-yl β-D-glucopyranosiduronic acidGenerator
17b-Hydroxy-5a-androstan-3-one glucuronideGenerator
17Β-hydroxy-5α-androstan-3-one glucuronideGenerator
5a-Dihydrotestosterone 17-(b-D-glucuronide)Generator
5Α-dihydrotestosterone 17-(β-D-glucuronide)Generator
5a-Dihydrotestosterone 17-b-glucuronideGenerator
5Α-dihydrotestosterone 17-β-glucuronideGenerator
5a-Dihydrotestosterone 17-O-(b-D-glucuronate)Generator
5a-Dihydrotestosterone 17-O-(b-D-glucuronic acid)Generator
5alpha-Dihydrotestosterone 17-O-(beta-D-glucuronate)Generator
5Α-dihydrotestosterone 17-O-(β-D-glucuronate)Generator
5Α-dihydrotestosterone 17-O-(β-D-glucuronic acid)Generator
5a-Dihydrotestosterone glucuronideGenerator
5Α-dihydrotestosterone glucuronideGenerator
5a-Dihydrotestosterone-17gGenerator
5Α-dihydrotestosterone-17gGenerator
Stanolone glucuronic acidGenerator
5-a-Dihydrotestosterone glucuronideGenerator
5-Α-dihydrotestosterone glucuronideGenerator
Dihydrotestosterone diglucuronideHMDB
Dihydrotestosterone glucuronide, (5beta,17beta)-isomerHMDB
5-alpha-Dihydrotestosterone glucuronidehmdb
Predicted PropertiesNot Available
Chemical FormulaC25H38O8
IUPAC name
InChI IdentifierInChI=1S/C25H38O8/c1-24-9-7-13(26)11-12(24)3-4-14-15-5-6-17(25(15,2)10-8-16(14)24)32-23-20(29)18(27)19(28)21(33-23)22(30)31/h12,14-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,14-,15-,16-,17-,18-,19-,20+,21-,23+,24-,25-/m0/s1
InChI KeyCLQMBSSRTBUNDV-CPKOJWPQSA-N
Isomeric SMILES[H][C@@]12CC[C@H](O[C@]3([H])O[C@@H]([C@@H](O)[C@H](O)[C@H]3O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)CC[C@]12C
Average Molecular Weight466.5644
Monoisotopic Molecular Weight466.256668192
Classification
Description Belongs to the class of organic compounds known as steroid glucuronide conjugates. These are sterol lipids containing a glucuronide moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroidal glycosides
Direct ParentSteroid glucuronide conjugates
Alternative Parents
Substituents
  • Steroid-glucuronide-skeleton
  • Androgen-skeleton
  • Androstane-skeleton
  • 3-oxosteroid
  • 3-oxo-5-alpha-steroid
  • Oxosteroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Beta-hydroxy acid
  • Hydroxy acid
  • Oxane
  • Monosaccharide
  • Pyran
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Polyol
  • Acetal
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • 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
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID24850129
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID44263365
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06203
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2423365
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