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Record Information
Version2.0
Created at2022-05-11 16:50:13 UTC
Updated at2022-05-11 16:50:14 UTC
NP-MRD IDNP0087458
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-alpha-Dihydrotestosterone glucuronide
Description5-Alpha-Dihydrotestosterone glucuronide, also known as stanolone glucuronate or 17b-hydroxy-5a-androstan-3-one glucuronide, 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. Thus, 5-alpha-dihydrotestosterone glucuronide is considered to be a steroid conjugate lipid molecule. 5-alpha-Dihydrotestosterone glucuronide was first documented in 1978 (PMID: 263350). 5-Alpha-Dihydrotestosterone glucuronide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 12560362) (PMID: 3140586).
Structure
Thumb
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 Mass466.5644 Da
Monoisotopic Mass466.25667 Da
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
CAS Registry NumberNot Available
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 Identifier
InChI=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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0006203
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023835
KNApSAcK IDNot Available
Chemspider ID24850129
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2423365
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44263365
PDB IDNot Available
ChEBI ID89417
Good Scents IDNot Available
References
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. [PubMed:12560362 ]
  2. 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. doi: 10.3109/09513598709082705. [PubMed:3140586 ]
  3. Ishimaru T, Edmiston A, Pages L, Horton R: Direct conversion of testosterone to dihydrotestosterone glucuronide in man. J Clin Endocrinol Metab. 1978 Dec;47(6):1282-6. doi: 10.1210/jcem-47-6-1282. [PubMed:263350 ]