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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:19:04 UTC
HMDB IDHMDB0000502
Secondary Accession Numbers
  • HMDB00502
  • HMDB0062680
  • HMDB62680
Metabolite Identification
Common Name3-Oxocholic acid
Description3-Oxocholic acid, also known as 7alpha,12alpha-dihydroxy-3-oxo-5beta-cholan-24-oic acid, is a bile acid. Bile acids are steroid acids found predominantly in the bile of mammals. The distinction between different bile acids is minute, depending only on the presence or absence of hydroxyl groups on positions 3, 7, and 12. 3-Oxocholic acid is considered to be practically insoluble (in water) and acidic.
Structure
Data?1582752135
Synonyms
ValueSource
(5beta,7alpha,12alpha)-7,12-Dihydroxy-3-oxocholan-24-Oic acidChEBI
3-Dehydrocholic acidChEBI
3-Ketocholic acidChEBI
3-Oxocholic acidChEBI
7,12-Dihydroxy-3-oxocholanic acidChEBI
7alpha,12alpha-Dihydroxy-3-oxo-cholanoic acidChEBI
(5b,7a,12a)-7,12-Dihydroxy-3-oxocholan-24-OateGenerator
(5b,7a,12a)-7,12-Dihydroxy-3-oxocholan-24-Oic acidGenerator
(5beta,7alpha,12alpha)-7,12-Dihydroxy-3-oxocholan-24-OateGenerator
(5Β,7α,12α)-7,12-dihydroxy-3-oxocholan-24-OateGenerator
(5Β,7α,12α)-7,12-dihydroxy-3-oxocholan-24-Oic acidGenerator
3-DehydrocholateGenerator
3-KetocholateGenerator
3-OxocholateGenerator
7,12-Dihydroxy-3-oxocholanateGenerator
7a,12a-Dihydroxy-3-oxo-cholanoateGenerator
7a,12a-Dihydroxy-3-oxo-cholanoic acidGenerator
7alpha,12alpha-Dihydroxy-3-oxo-cholanoateGenerator
7Α,12α-dihydroxy-3-oxo-cholanoateGenerator
7Α,12α-dihydroxy-3-oxo-cholanoic acidGenerator
7a,12a-Dihydroxy-3-oxo-5b-cholan-24-OateGenerator
7a,12a-Dihydroxy-3-oxo-5b-cholan-24-Oic acidGenerator
7alpha,12alpha-Dihydroxy-3-oxo-5beta-cholan-24-OateGenerator
7Α,12α-dihydroxy-3-oxo-5β-cholan-24-OateGenerator
7Α,12α-dihydroxy-3-oxo-5β-cholan-24-Oic acidGenerator
7alpha,12alpha-Dihydroxy-3-oxo-5beta-cholan-24-oic acidHMDB
Chemical FormulaC24H38O5
Average Molecular Weight406.563
Monoisotopic Molecular Weight406.271924324
IUPAC Name(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2S,7R,9R,10R,11S,14R,15R,16S)-9,16-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number2304-89-4
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O
InChI Identifier
InChI=1S/C24H38O5/c1-13(4-7-21(28)29)16-5-6-17-22-18(12-20(27)24(16,17)3)23(2)9-8-15(25)10-14(23)11-19(22)26/h13-14,16-20,22,26-27H,4-12H2,1-3H3,(H,28,29)/t13-,14+,16-,17+,18+,19-,20+,22+,23+,24-/m1/s1
InChI KeyOEKUSRBIIZNLHZ-DJDNIQJZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-oxosteroid
  • 12-hydroxysteroid
  • 3-oxo-5-beta-steroid
  • 7-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point218 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.041 g/LALOGPS
logP10(2.24) g/LALOGPS
logP10(2.69) g/LChemAxon
logS10(-4) g/LALOGPS
pKa (Strongest Acidic)4.48ChemAxon
pKa (Strongest Basic)-0.18ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity109.76 m³·mol⁻¹ChemAxon
Polarizability46.23 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.89231661259
DarkChem[M-H]-186.87531661259
AllCCS[M+H]+201.84332859911
AllCCS[M-H]-201.13932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Oxocholic acid[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O4130.7Standard polar33892256
3-Oxocholic acid[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O3461.2Standard non polar33892256
3-Oxocholic acid[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C[C@]4([H])CC(=O)CC[C@]4(C)[C@@]3([H])C[C@H](O)[C@]12C)[C@H](C)CCC(O)=O3700.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Oxocholic acid,1TMS,isomer #1C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C3390.6Semi standard non polar33892256
3-Oxocholic acid,1TMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O3445.2Semi standard non polar33892256
3-Oxocholic acid,1TMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O3467.3Semi standard non polar33892256
3-Oxocholic acid,1TMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O3438.1Semi standard non polar33892256
3-Oxocholic acid,1TMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O3399.3Semi standard non polar33892256
3-Oxocholic acid,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C3342.2Semi standard non polar33892256
3-Oxocholic acid,2TMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C3351.9Semi standard non polar33892256
3-Oxocholic acid,2TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C3328.2Semi standard non polar33892256
3-Oxocholic acid,2TMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3347.5Semi standard non polar33892256
3-Oxocholic acid,2TMS,isomer #5C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O3404.5Semi standard non polar33892256
3-Oxocholic acid,2TMS,isomer #6C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O3353.7Semi standard non polar33892256
3-Oxocholic acid,2TMS,isomer #7C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O3370.7Semi standard non polar33892256
3-Oxocholic acid,2TMS,isomer #8C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O3365.4Semi standard non polar33892256
3-Oxocholic acid,2TMS,isomer #9C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O3398.5Semi standard non polar33892256
3-Oxocholic acid,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C3340.7Semi standard non polar33892256
3-Oxocholic acid,3TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C3314.6Semi standard non polar33892256
3-Oxocholic acid,3TMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3332.7Semi standard non polar33892256
3-Oxocholic acid,3TMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C3318.8Semi standard non polar33892256
3-Oxocholic acid,3TMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3336.4Semi standard non polar33892256
3-Oxocholic acid,3TMS,isomer #6C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O3334.1Semi standard non polar33892256
3-Oxocholic acid,3TMS,isomer #7C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O3350.1Semi standard non polar33892256
3-Oxocholic acid,4TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C3313.6Semi standard non polar33892256
3-Oxocholic acid,4TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C3363.7Standard non polar33892256
3-Oxocholic acid,4TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C3502.5Standard polar33892256
3-Oxocholic acid,4TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3339.4Semi standard non polar33892256
3-Oxocholic acid,4TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3344.3Standard non polar33892256
3-Oxocholic acid,4TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C3506.3Standard polar33892256
3-Oxocholic acid,1TBDMS,isomer #1C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3606.6Semi standard non polar33892256
3-Oxocholic acid,1TBDMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O3665.5Semi standard non polar33892256
3-Oxocholic acid,1TBDMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O3714.0Semi standard non polar33892256
3-Oxocholic acid,1TBDMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3673.8Semi standard non polar33892256
3-Oxocholic acid,1TBDMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O3629.9Semi standard non polar33892256
3-Oxocholic acid,2TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3789.9Semi standard non polar33892256
3-Oxocholic acid,2TBDMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3785.2Semi standard non polar33892256
3-Oxocholic acid,2TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3743.6Semi standard non polar33892256
3-Oxocholic acid,2TBDMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3768.7Semi standard non polar33892256
3-Oxocholic acid,2TBDMS,isomer #5C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O3867.5Semi standard non polar33892256
3-Oxocholic acid,2TBDMS,isomer #6C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O3769.3Semi standard non polar33892256
3-Oxocholic acid,2TBDMS,isomer #7C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3804.8Semi standard non polar33892256
3-Oxocholic acid,2TBDMS,isomer #8C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O3808.7Semi standard non polar33892256
3-Oxocholic acid,2TBDMS,isomer #9C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3850.5Semi standard non polar33892256
3-Oxocholic acid,3TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(=O)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3993.8Semi standard non polar33892256
3-Oxocholic acid,3TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3923.3Semi standard non polar33892256
3-Oxocholic acid,3TBDMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3946.1Semi standard non polar33892256
3-Oxocholic acid,3TBDMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3937.7Semi standard non polar33892256
3-Oxocholic acid,3TBDMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3966.5Semi standard non polar33892256
3-Oxocholic acid,3TBDMS,isomer #6C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O3952.2Semi standard non polar33892256
3-Oxocholic acid,3TBDMS,isomer #7C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O3982.3Semi standard non polar33892256
3-Oxocholic acid,4TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4122.7Semi standard non polar33892256
3-Oxocholic acid,4TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4013.3Standard non polar33892256
3-Oxocholic acid,4TBDMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CCC(O[Si](C)(C)C(C)(C)C)=C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3795.7Standard polar33892256
3-Oxocholic acid,4TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C4144.8Semi standard non polar33892256
3-Oxocholic acid,4TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3932.6Standard non polar33892256
3-Oxocholic acid,4TBDMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C(C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](C[C@H](O[Si](C)(C)C(C)(C)C)[C@@]21C)[C@@]1(C)CC=C(O[Si](C)(C)C(C)(C)C)C[C@H]1C[C@H]3O[Si](C)(C)C(C)(C)C3799.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0449000000-a048d1efc6c00034ad572017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-2231189000-30c1ecbaf9541625b7542017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_3_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_3_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TMS_3_7) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Oxocholic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 10V, Positive-QTOFsplash10-0079-0009000000-64f2f2abc7d1633027d52017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 20V, Positive-QTOFsplash10-00dr-0009000000-bcfa1c4097826adbabd92017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 40V, Positive-QTOFsplash10-056u-2109000000-fe0a92a5f377efc3a7ae2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 10V, Negative-QTOFsplash10-0a4r-0008900000-dd8b045786455a7b2b5f2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 20V, Negative-QTOFsplash10-052r-1009300000-40bda8fb29d7dc21b6442017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 40V, Negative-QTOFsplash10-0a4l-9006000000-15440129ab1b7eb75b362017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 10V, Positive-QTOFsplash10-0ab9-0009600000-267c1c0d5a13c4bebc102021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 20V, Positive-QTOFsplash10-052r-2159000000-97af577c50737e77d1522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 40V, Positive-QTOFsplash10-0a4l-9232000000-99073abfe404b118814d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 10V, Negative-QTOFsplash10-0a4i-0000900000-f0b489debf71eabc30f82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 20V, Negative-QTOFsplash10-0a4r-0008900000-e453fd1548d30dd5bb332021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxocholic acid 40V, Negative-QTOFsplash10-0udi-1029400000-c23a051d71ab55c9d40e2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Feces
Tissue Locations
  • Gall Bladder
  • Intestine
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283956
PDB IDNot Available
ChEBI ID88108
Food Biomarker OntologyNot Available
VMH ID3DHCHOL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceProduction of 7a,12a-dihydroxy-3-keto-5b-cholanic acid. Jpn. Kokai Tokkyo Koho (1981), 12 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. [PubMed:12829005 ]
  2. Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. [PubMed:10203155 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in binding
Specific function:
Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
Gene Name:
FABP6
Uniprot ID:
P51161
Molecular weight:
14371.2
References
  1. Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
Gene Name:
SLCO1B3
Uniprot ID:
Q9NPD5
Molecular weight:
77402.2
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
Gene Name:
SLCO1B1
Uniprot ID:
Q9Y6L6
Molecular weight:
76448.0
References
  1. Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]
General function:
Involved in ATP binding
Specific function:
May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
Gene Name:
ABCC3
Uniprot ID:
O15438
Molecular weight:
169341.1
General function:
Involved in ATP binding
Specific function:
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
Gene Name:
ABCB11
Uniprot ID:
O95342
Molecular weight:
146405.8
General function:
Involved in bile acid:sodium symporter activity
Specific function:
Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
Gene Name:
SLC10A2
Uniprot ID:
Q12908
Molecular weight:
37697.4
References
  1. Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]
General function:
Involved in bile acid:sodium symporter activity
Specific function:
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
Gene Name:
SLC10A1
Uniprot ID:
Q14973
Molecular weight:
38118.64
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
Gene Name:
SLCO1A2
Uniprot ID:
P46721
Molecular weight:
74144.1
General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
Gene Name:
SLCO4A1
Uniprot ID:
Q96BD0
Molecular weight:
77192.5