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Showing Compound Androsterone glucuronide (FDB023070)

Record Information
Version1.0
Creation date2011-09-21 00:24:14 UTC
Update date2015-07-21 06:57:29 UTC
Primary IDFDB023070
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAndrosterone glucuronide
DescriptionAndrosterone glucuronide (ADT-G) is one of the major circulating C19-steroid metabolites in humans. Human and monkey are unique in having high levels of circulating ADT-G. Furthermore, the plasma levels of these glucuronide derivatives reflect the peripheral tissue conversion of adrenal and gonadal precursor C19-steroids to active androgens in various pathophysiological conditions. Identification and characterization of human UDP-glucuronosyltransferase 2B (UGT2Bs) demonstrated the major role that these enzymes play in androgen conjugation, with UGT2B15 and UGT2B17 (EC 2.4.1.17) being the major androsterone-conjugating isoforms. Exaggerated androsterone metabolism, is observed in hyper-androgenic as well as in some normo-androgenic women with acne and androsterone glucuronide could be a marker in differentiating acne and hirsutism in hyperandrogenic women. Present data shows that the most practical and probably only valid means of assessing androgenic activity in women is to measure ADT-G, the metabolite that accounts for 93% of the total androgen glucuronide derivatives. (PMID: 12943709, 12445184, 16621522) [HMDB]
CAS Number1852-43-3
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP2.06ALOGPS
logP2.32ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity116.09 m³·mol⁻¹ChemAxon
Polarizability50.56 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC25H38O8
IUPAC name(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7S,10R,11S,15S)-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI IdentifierInChI=1S/C25H38O8/c1-24-9-7-13(32-23-20(29)18(27)19(28)21(33-23)22(30)31)11-12(24)3-4-14-15-5-6-17(26)25(15,2)10-8-16(14)24/h12-16,18-21,23,27-29H,3-11H2,1-2H3,(H,30,31)/t12-,13+,14-,15-,16-,18-,19-,20+,21-,23+,24-,25-/m0/s1
InChI KeyVFUIRAVTUVCQTF-BSOWLZGZSA-N
Isomeric SMILES[H][C@@]12CCC(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
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
  • Androstane-skeleton
  • Oxosteroid
  • 17-oxosteroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Monosaccharide
  • Pyran
  • Oxane
  • Hydroxy acid
  • Ketone
  • Secondary alcohol
  • Acetal
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • 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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAndrosterone glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007a-6254900000-3224ce201f4200b35e4cSpectrum
Predicted GC-MSAndrosterone glucuronide, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-2335019000-fb5b67aba04100369c5bSpectrum
Predicted GC-MSAndrosterone glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSAndrosterone glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r7-0190600000-3fdda78a1e92f8b5b7b22016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-0290000000-51d6fe94f1974c92c97f2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ec-0590000000-71f03526102b61380a882016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01bi-1260900000-703dccf114629fa639b72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1290200000-1db7014540df9034a06e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-4190000000-b2d4d7c7847df524456f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000900000-80c326e64042176a4be82021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fs-0792300000-a93b9d1cdd42d4c7cde22021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05bb-1904000000-0daa4e3ba6eed62c511b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-a63f64862ace09c4006b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-5241900000-384ea6662fc4abc18a4b2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9032100000-351b0f7123639e6a74432021-09-24View Spectrum
NMRNot Available
ChemSpider ID102793
ChEMBL IDNot Available
KEGG Compound IDC11135
Pubchem Compound ID114833
Pubchem Substance IDNot Available
ChEBI ID28832
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02829
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID2304839
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference