Record Information
Version1.0
Creation date2011-09-21 00:23:13 UTC
Update date2015-07-21 06:57:28 UTC
Primary IDFDB023010
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid
Descriptionb-D-GlucopyranosIduronic acid, (3a,5b,7a,12a)-24-[(carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl is found in the urine of leprosy patients. It is red in color similar to clofazimine. It is considered more polar than the parent drug. It is formed by hydrolytic deamination followed by glucuronidation.(PMID: 6120809) [HMDB]
CAS Number99794-78-2
Structure
Thumb
Synonyms
SynonymSource
Glycocholic acid 3-glucuronidehmdb
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP0.76ALOGPS
logP-0.073ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.29ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area223.31 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity155.87 m³·mol⁻¹ChemAxon
Polarizability66.73 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC32H51NO12
IUPAC name(2S,3S,4S,5R,6R)-6-{[(1S,2S,5R,7R,9R,10R,11S,15R,16S)-14-[(2R)-4-[(carboxymethyl)carbamoyl]butan-2-yl]-9,16-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
InChI IdentifierInChI=1S/C32H51NO12/c1-14(4-7-22(36)33-13-23(37)38)17-5-6-18-24-19(12-21(35)32(17,18)3)31(2)9-8-16(10-15(31)11-20(24)34)44-30-27(41)25(39)26(40)28(45-30)29(42)43/h14-21,24-28,30,34-35,39-41H,4-13H2,1-3H3,(H,33,36)(H,37,38)(H,42,43)/t14-,15+,16-,17?,18+,19+,20-,21+,24+,25+,26+,27-,28+,30-,31+,32-/m1/s1
InChI KeyBWWWIHHYPYDOJQ-BSGVGGAOSA-N
Isomeric SMILES[H][C@@]12CCC([C@H](C)CCC(=O)NCC(O)=O)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[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 Weight641.7468
Monoisotopic Molecular Weight641.341126101
Classification
ClassificationNot classified
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
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-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00r2-5182579000-392cd6c4338e0f9ae70aSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(3alpha,5beta,7alpha,12alpha)-24-[(Carboxymethyl)amino]-1,12-dihydroxy-24-oxocholan-3-yl-beta-D-glucopyranosiduronic acid, TMS_2_16, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-8000819000-b5a6fe5c16743fbb6a04Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-9000400000-127b3789cd584c94c599Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9001100000-49290a85b0f67fda39c8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-1200869000-a997d036227b3c39b543Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ot-2200921000-7acb6a79617c0cf6cbc6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03k9-7402900000-733105210d79eb151325Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006x-0000019000-f2047bcf685fe140d997Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff1-0023954000-97b9ffeb8f0e49f899b2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9134330000-761c503592e8a47d43f5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000019000-01043e8c2d7c4af029adSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0kkd-7100389000-8d5bc9db65f97b1dd280Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-9000230000-0a303b84e5d78963e09bSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477752
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02472
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 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-6UGT1A6P19224
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference