5-alpha-Dihydrotestosterone glucuronide (CHEM022441)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:35:03 UTC
Update Date2016-11-09 01:17:30 UTC
Accession NumberCHEM022441
Identification
Common Name5-alpha-Dihydrotestosterone glucuronide
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(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
Chemical FormulaC25H38O8
Average Molecular Mass466.564 g/mol
Monoisotopic Mass466.257 g/mol
CAS Registry Number42037-24-1
IUPAC Name(2S,3S,4S,5R,6R)-6-{[(1S,2S,7S,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-6-{[(1S,2S,7S,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
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
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
Chemical Taxonomy
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
logP2.1ALOGPS
logP1.96ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity115.88 m³·mol⁻¹ChemAxon
Polarizability50.03 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-007a-6264900000-caa236f8fcb97291d23bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-1261029000-94f9c3d5903740431670Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r7-0190600000-74d7352cda2362ddb906Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0290000000-8dcf4c902df6743a8f9eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-0490000000-278db46d2af73936b3beSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bi-1260900000-3c796e68ff231c8976b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-f56012a4058dcff174caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4190000000-14bb869866e58062e6fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-8ccc8d81a1705cd514f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ara-9421500000-426185885a7fcd23f188Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9103100000-942b47d6aa0fb6b5c1acSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ba-0150900000-8a78977927165645dce7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01vk-0954600000-159af7866ca65a3c8336Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ap0-1911000000-5865b00a94ace6eedd9fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006203
FooDB IDFDB023835
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2423365
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID24850129
ChEBI ID89417
PubChem Compound ID44263365
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Choi MH, Kim JN, Chung BC: Rapid HPLC-electrospray tandem mass spectrometric assay for urinary testosterone and dihydrotestosterone glucuronides from patients with benign prostate hyperplasia. Clin Chem. 2003 Feb;49(2):322-5.
2. Murai T, Samata N, Iwabuchi H, Ikeda T: Human UDP-glucuronosyltransferase, UGT1A8, glucuronidates dihydrotestosterone to a monoglucuronide and further to a structurally novel diglucuronide. Drug Metab Dispos. 2006 Jul;34(7):1102-8. Epub 2006 Apr 4.
3. Prevost J, Brochu M, Belanger A, Lambert R: Conjugated and unconjugated C-21, C-19 and C-18 steroid concentrations in human follicular fluid from hyperstimulated follicles. Gynecol Endocrinol. 1987 Dec;1(4):331-8.
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=10624837
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=12560362
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16595710
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=263350
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=2747415
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=3140586