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Showing Compound (3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid (FDB023002)

Record Information
Version1.0
Creation date2011-09-21 00:23:07 UTC
Update date2015-07-21 06:57:28 UTC
Primary IDFDB023002
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid
Description(3a,5b,7a)-23-carboxy-7-hydroxy-24-norcholan-3-yl-b-D-Glucopyranosiduronic acid is a natural human metabolite of Chenodeoxycholic acid 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 Number58814-71-4
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.91ALOGPS
logP2.26ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)-0.61ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area173.98 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity141.55 m³·mol⁻¹ChemAxon
Polarizability62.68 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H48O10
IUPAC name(2S,3S,4S,5R)-6-{[(1S,2S,5R,7R,9R,10R,11S,14R,15R)-14-[(2R)-4-carboxybutan-2-yl]-9-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI IdentifierInChI=1S/C30H48O10/c1-14(4-7-21(32)33)17-5-6-18-22-19(9-11-30(17,18)3)29(2)10-8-16(12-15(29)13-20(22)31)39-28-25(36)23(34)24(35)26(40-28)27(37)38/h14-20,22-26,28,31,34-36H,4-13H2,1-3H3,(H,32,33)(H,37,38)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24+,25-,26+,28?,29+,30-/m1/s1
InChI KeyGDNGOAUIUTXUES-RWDHRDFGSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])C[C@@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)[C@H](C)CCC(O)=O
Average Molecular Weight568.6961
Monoisotopic Molecular Weight568.324747756
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
  • Hydroxy bile acid, alcohol, or derivatives
  • Monohydroxy bile acid, alcohol, or derivatives
  • Bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • Hydroxysteroid
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Pyran
  • Monosaccharide
  • Oxane
  • Cyclic alcohol
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Acetal
  • Carboxylic acid
  • Carboxylic acid derivative
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

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-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ug0-5435490000-ea2448ceaf4bb38dcc03Spectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0059-2637439000-07503a65be07e3a6e4afSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, "(3a,5b,7a)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-b-D-Glucopyranosiduronic acid,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha)-23-Carboxy-7-hydroxy-24-norcholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ugi-0007090000-254730663e45c40bc8bd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009010000-252cefe3d9408c7a26592017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01rt-0109000000-02d4a762628492f8776f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00xr-1104090000-a8b51e62c16844943d452017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fu-1109040000-316f20197091fcc5b6362017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-5109000000-a51c62af5341d33e4e8d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000090000-13858058d0b4374903da2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-2101190000-33fdddb30dbe23cc88ca2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06di-9102750000-b6dec0c21587c3213aac2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000090000-d003380ad0e3745b7c372021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi0-1039020000-f134855a9f2d87c282cc2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-5392400000-1a94d8b81b799eb51faa2021-09-24View Spectrum
NMRNot Available
ChemSpider ID13628354
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID21252299
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02430
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
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