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Showing Compound Pregnanediol-3-glucuronide (FDB027470)

Record Information
Version1.0
Creation date2011-09-21 01:24:52 UTC
Update date2015-07-21 06:59:07 UTC
Primary IDFDB027470
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePregnanediol-3-glucuronide
DescriptionPregnanediol-3-glucuronide is a natural human metabolite of Pregnanediol 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 NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
5 beta-Pregnane-3 alpha, 20 alpha-diol-3 alpha-glucuronideHMDB
Pregnanediol-3 alpha-glucuronide, (3alpha,5alpha,20S)-isomerHMDB
20 alpha-Hydroxy-5 beta-pregnan-3 alpha-yl-beta-D-glucopyranosiduronic acidHMDB
Pregnanediol-3 alpha-glucuronideHMDB
(2S,3S,4S,5R,6R)-3,4,5-Trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}oxane-2-carboxylateHMDB
Pregnanediol-3-glucuronideHMDB
(3alpha,5beta,20S)-20-Hydroxypregnan-3-yl beta-D-glucopyranosiduronic acidHMDB
(3Α,5β,20S)-20-hydroxypregnan-3-yl β-D-glucopyranosiduronic acidHMDB
5beta-Pregnane-3alpha,20alpha-diol glucuronideHMDB
5Β-pregnane-3α,20α-diol glucuronideHMDB
Pregnanediol 3-glucuronideHMDB
Pregnanediol 3alpha-monoglucuronideHMDB
Pregnanediol 3α-monoglucuronideHMDB
Pregnanediol-3alpha-glucuronideHMDB
Pregnanediol-3alpha-glucuronosideHMDB
Pregnanediol-3α-glucuronideHMDB
Pregnanediol-3α-glucuronosideHMDB
Pregnanediol 3-O-glucuronideHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.35ALOGPS
logP2.33ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity126.22 m³·mol⁻¹ChemAxon
Polarizability54.34 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC27H44O8
IUPAC name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7R,10R,11S,14S,15S)-14-[(1S)-1-hydroxyethyl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C27H44O8/c1-13(28)17-6-7-18-16-5-4-14-12-15(8-10-26(14,2)19(16)9-11-27(17,18)3)34-25-22(31)20(29)21(30)23(35-25)24(32)33/h13-23,25,28-31H,4-12H2,1-3H3,(H,32,33)/t13-,14+,15+,16-,17+,18-,19-,20-,21-,22+,23-,25+,26-,27+/m0/s1
InChI KeyZFFFJLDTCLJDHL-JQYCEVDMSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@H](C)O
Average Molecular Weight496.6335
Monoisotopic Molecular Weight496.303618384
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
  • 20-hydroxysteroid
  • Pregnane-skeleton
  • Hydroxysteroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Organoheterocyclic compound
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
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-MS
TypeDescriptionSplash KeyView
Predicted GC-MSPregnanediol-3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-4122900000-3e5f97505fa59189dd8aSpectrum
Predicted GC-MSPregnanediol-3-glucuronide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-5415119000-90a0b62f2a718e2d1765Spectrum
Predicted GC-MSPregnanediol-3-glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0umj-0129800000-0d59ade653b8fb96b9bc2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-0229100000-4ecc43e457fb8862adc82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w90-0494000000-72359c56cb5b7db470362016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fr2-1106900000-08ac183a8e920e9b73ea2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-1219300000-b1547008deb27628e8042016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-4139000000-d9eee9323f0ccb5bc10f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000900000-3d0e31ca68d2b17484ea2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-054k-4103900000-b6501e5783bcc68f91e02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9006600000-90be1679288bfe26dfdb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-0000900000-b1d27679a5224a866ee62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f9i-0395400000-257423d4e5e3d5c223a72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06xt-1904000000-f4175cf3754ea7f7529f2021-09-24View Spectrum
NMRNot Available
ChemSpider ID110346
ChEMBL IDNot Available
KEGG Compound IDC03033
Pubchem Compound ID123796
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB10318
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 2B7UGT2B7P16662
UDP-glucuronosyltransferase 2B15UGT2B15P54855
UDP-glucuronosyltransferase 2A1UGT2A1Q9Y4X1
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-8UGT1A8Q9HAW9
UDP-glucuronosyltransferase 1-3UGT1A3P35503
UDP-glucuronosyltransferase 1-10UGT1A10Q9HAW8
UDP-glucuronosyltransferase 2B17UGT2B17O75795
UDP-glucuronosyltransferase 1-6UGT1A6P19224
UDP-glucuronosyltransferase 1-5UGT1A5P35504
UDP-glucuronosyltransferase 2B11UGT2B11O75310
UDP-glucuronosyltransferase 1-7UGT1A7Q9HAW7
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