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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:40:07 UTC
HMDB IDHMDB0000415
Secondary Accession Numbers
  • HMDB00415
Metabolite Identification
Common Name3a,6b,7b-Trihydroxy-5b-cholanoic acid
Description3a,6b,7b-Trihydroxy-5b-cholanoic acid, also known as beta-muricholic acid, is a bile acid. 3a,6b,7b-Trihydroxy-5b-cholanoic acid belongs to the class of compounds known muricholic acids in which the hydroxy groups at positions 6 and 7 both have a beta configuration. It is also classified as a 6beta-hydroxy steroid, a 7beta-hydroxy steroid, a steroid acid and a bile acid. Muricholic acids are a group of bile acids that are particularly abundant in mice, which gives them their name. Muricholic acids are also found at low concentrations in other mammalian species, including humans (PMID: 12543708 ). Muricholic acids differ from the primary bile acids found in humans (which are cholic acid and chenodeoxycholic acid) by having a hydroxyl group in the beta-conformation at the 6-position. The orientation of the hydroxyl group at the 7 position defines alpha- or beta-muricholic acid. Muricholic acids are detectable at low concentrations in human urine (PMIDL 1629271). The enzyme responsible for the 6-hydroxylation reactions forming muricholates in rodents is the cytochrome P450 Cyp2c70. This produces alpha-muricholic acid from chenodeoxycholic acid, and beta-muricholic acid from ursodeoxycholic acid. Bile acids, such as muricholic acid, 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, 6, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g. membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues (PMID: 11316487 , 16037564 , 12576301 , 11907135 ).
Structure
Data?1582752130
Synonyms
ValueSource
(3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-Oic acidChEBI
3,6,7-Trihydroxy-5beta-cholan-24-Oic acidChEBI
5beta-Cholanic acid-3alpha,6beta,7beta-triolChEBI
beta-MCAChEBI
beta-Muricholic acidKegg
3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-Oic acidKegg
(3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-OateGenerator
(3a,5b,6b,7b)-3,6,7-Trihydroxycholan-24-Oic acidGenerator
(3alpha,5beta,6beta,7beta)-3,6,7-Trihydroxycholan-24-OateGenerator
(3Α,5β,6β,7β)-3,6,7-trihydroxycholan-24-OateGenerator
(3Α,5β,6β,7β)-3,6,7-trihydroxycholan-24-Oic acidGenerator
3,6,7-Trihydroxy-5b-cholan-24-OateGenerator
3,6,7-Trihydroxy-5b-cholan-24-Oic acidGenerator
3,6,7-Trihydroxy-5beta-cholan-24-OateGenerator
3,6,7-Trihydroxy-5β-cholan-24-OateGenerator
3,6,7-Trihydroxy-5β-cholan-24-Oic acidGenerator
5b-Cholanate-3a,6b,7b-triolGenerator
5b-Cholanic acid-3a,6b,7b-triolGenerator
5beta-Cholanate-3alpha,6beta,7beta-triolGenerator
5Β-cholanate-3α,6β,7β-triolGenerator
5Β-cholanic acid-3α,6β,7β-triolGenerator
b-MCAGenerator
Β-mcaGenerator
b-MuricholateGenerator
b-Muricholic acidGenerator
beta-MuricholateGenerator
Β-muricholateGenerator
Β-muricholic acidGenerator
3a,6b,7b-Trihydroxy-5b-cholan-24-OateGenerator
3a,6b,7b-Trihydroxy-5b-cholan-24-Oic acidGenerator
3alpha,6beta,7beta-Trihydroxy-5beta-cholan-24-OateGenerator
3Α,6β,7β-trihydroxy-5β-cholan-24-OateGenerator
3Α,6β,7β-trihydroxy-5β-cholan-24-Oic acidGenerator
3a,6b,7b-Trihydroxy-5b-cholanoateGenerator
3a,6b,7b-Trihydroxy-5b-cholanateHMDB
3a,6b,7b-Trihydroxy-5b-cholanic acidHMDB
3 alpha,6 alpha,7 beta-Trihydroxy-5 beta-cholanoic acidHMDB
3,6,7-Trihydroxy-5-cholanoic acidHMDB
alpha-Muricholic acidHMDB
Hyocholic acidHMDB
Muricholic acidHMDB
Muricholic acid, (3alpha,5alpha,6alpha,7alpha)-isomerHMDB
Muricholic acid, (3alpha,5beta,6alpha,7alpha)-isomerHMDB
Muricholic acid, (3alpha,5beta,6alpha,7beta)-isomerHMDB
Muricholic acid, (3alpha,5beta,6beta,7alpha)-isomerHMDB
Muricholic acid, (3alpha,5beta,6beta,7beta)-isomerHMDB
Muricholic acid, sodium saltHMDB
Omega-muricholic acidHMDB
Trihydroxy-5 alpha-cholanoic acidHMDB
Chemical FormulaC24H40O5
Average Molecular Weight408.5714
Monoisotopic Molecular Weight408.28757439
IUPAC Name(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
Traditional Name(4R)-4-[(1S,2R,5R,7R,8S,9R,10S,11S,14R,15R)-5,8,9-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
CAS Registry Number2393-59-1
SMILES
[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C24H40O5/c1-13(4-7-19(26)27)15-5-6-16-20-17(9-11-23(15,16)2)24(3)10-8-14(25)12-18(24)21(28)22(20)29/h13-18,20-22,25,28-29H,4-12H2,1-3H3,(H,26,27)/t13-,14-,15-,16+,17+,18+,20+,21+,22-,23-,24-/m1/s1
InChI KeyDKPMWHFRUGMUKF-CRKPLTDNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 6-hydroxysteroid
  • 7-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available203.019http://allccs.zhulab.cn/database/detail?ID=AllCCS00001889
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.069 g/LALOGPS
logP10(2.16) g/LALOGPS
logP10(2.72) g/LChemAxon
logS10(-3.8) g/LALOGPS
pKa (Strongest Acidic)4.6ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.56 m³·mol⁻¹ChemAxon
Polarizability47.31 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]+31661259
DarkChem[M-H]-31661259
AllCCS[M+H]+203.27232859911
AllCCS[M-H]-201.03632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3a,6b,7b-Trihydroxy-5b-cholanoic acid[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C3746.2Standard polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C3502.6Standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid[H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](O)[C@@H](O)[C@]2([H])C[C@H](O)CC[C@]12C3627.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3a,6b,7b-Trihydroxy-5b-cholanoic acid,1TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O)[C@@H]3O3405.9Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,1TMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O)[C@@H]3O[Si](C)(C)C3355.8Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,1TMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O[Si](C)(C)C)[C@@H]3O3361.8Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,1TMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1[C@H](O)[C@@H]3O3431.5Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1[C@H](O)[C@@H]3O3381.3Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O[Si](C)(C)C)[C@@H]3O3310.4Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O)[C@@H]3O[Si](C)(C)C3308.0Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1[C@H](O)[C@@H]3O[Si](C)(C)C3309.3Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O[Si](C)(C)C)[C@@H]3O[Si](C)(C)C3282.7Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TMS,isomer #6C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1[C@H](O[Si](C)(C)C)[C@@H]3O3319.8Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1[C@H](O[Si](C)(C)C)[C@@H]3O3304.1Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #2C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1[C@H](O)[C@@H]3O[Si](C)(C)C3299.1Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #3C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O[Si](C)(C)C)[C@@H]3O[Si](C)(C)C3275.9Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,3TMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1[C@H](O[Si](C)(C)C)[C@@H]3O[Si](C)(C)C3299.0Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,4TMS,isomer #1C[C@H](CCC(=O)O[Si](C)(C)C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C)C[C@H]1[C@H](O[Si](C)(C)C)[C@@H]3O[Si](C)(C)C3314.0Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,1TBDMS,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](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O)[C@@H]3O3673.9Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #2C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O)[C@@H]3O[Si](C)(C)C(C)(C)C3574.1Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #3C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]3O3584.0Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,1TBDMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H](O)[C@@H]3O3653.3Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H](O)[C@@H]3O3863.3Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,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](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]3O3773.1Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,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](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O)[C@@H]3O[Si](C)(C)C(C)(C)C3754.0Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H](O)[C@@H]3O[Si](C)(C)C(C)(C)C3733.5Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #5C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]3O[Si](C)(C)C(C)(C)C3703.1Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,2TBDMS,isomer #6C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]3O3758.7Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]3O3949.2Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H](O)[C@@H]3O[Si](C)(C)C(C)(C)C3932.5Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](O)C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]3O[Si](C)(C)C(C)(C)C3895.8Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic acid,3TBDMS,isomer #4C[C@H](CCC(=O)O)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]3O[Si](C)(C)C(C)(C)C3911.7Semi standard non polar33892256
3a,6b,7b-Trihydroxy-5b-cholanoic 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](CC[C@@]21C)[C@@]1(C)CC[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]3O[Si](C)(C)C(C)(C)C4116.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-004l-0329000000-fed34af3d93baa3f73672017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (4 TMS) - 70eV, Positivesplash10-001i-1010029000-e5824ce563bff12a309c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 10V, Positive-QTOFsplash10-006x-0009100000-aeaf5bcdde74fe1ddf762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 20V, Positive-QTOFsplash10-00dm-0009000000-4af1ebd01d1d670d4f422017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 40V, Positive-QTOFsplash10-003u-2209000000-454d741b691e592d251a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 10V, Negative-QTOFsplash10-0a4i-0007900000-e501198616f74730538f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 20V, Negative-QTOFsplash10-052r-1009300000-9efc23876fa89e243bc62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 40V, Negative-QTOFsplash10-0a4l-9007000000-e5bd870e3f9870c89a142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 10V, Positive-QTOFsplash10-0ab9-0009600000-56beda528763ce5ae6df2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 20V, Positive-QTOFsplash10-059j-3449200000-98d256091462f2bbd8822021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 40V, Positive-QTOFsplash10-052u-4951000000-c203ad5efbf5e653aa092021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 10V, Negative-QTOFsplash10-0a4i-0001900000-68e3200734e1d0985f372021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 20V, Negative-QTOFsplash10-0a4r-0009800000-a11781ffcf06d8bb288c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,6b,7b-Trihydroxy-5b-cholanoic acid 40V, Negative-QTOFsplash10-0a4j-3009300000-d354f18e540a94d7dfe12021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)2012-12-05Wishart 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
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022031
KNApSAcK IDNot Available
Chemspider ID4446941
KEGG Compound IDC17726
BioCyc IDCPD-16583
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5404
PubChem Compound5283853
PDB IDNot Available
ChEBI ID81298
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceHsia, S. L.; Matschiner, John T.; Mahowald, Theodore A.; Elliott, Wm. H.; Doisy, E. A., Jr.; Thayer, Sidney A.; Doisy, Edward A. Bile acids. VII. Structure of acid I. Journal of Biological Chemistry (1958), 230 573-80.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Sacquet E, Parquet M, Riottot M, Raizman A, Nordlinger B, Infante R: Metabolism of beta-muricholic acid in man. Steroids. 1985 May;45(5):411-26. [PubMed:3834660 ]
  2. St-Pierre MV, Kullak-Ublick GA, Hagenbuch B, Meier PJ: Transport of bile acids in hepatic and non-hepatic tissues. J Exp Biol. 2001 May;204(Pt 10):1673-86. [PubMed:11316487 ]
  3. Claudel T, Staels B, Kuipers F: The Farnesoid X receptor: a molecular link between bile acid and lipid and glucose metabolism. Arterioscler Thromb Vasc Biol. 2005 Oct;25(10):2020-30. Epub 2005 Jul 21. [PubMed:16037564 ]
  4. Chiang JY: Bile acid regulation of hepatic physiology: III. Bile acids and nuclear receptors. Am J Physiol Gastrointest Liver Physiol. 2003 Mar;284(3):G349-56. [PubMed:12576301 ]
  5. Davis RA, Miyake JH, Hui TY, Spann NJ: Regulation of cholesterol-7alpha-hydroxylase: BAREly missing a SHP. J Lipid Res. 2002 Apr;43(4):533-43. [PubMed:11907135 ]
  6. Russell DW: The enzymes, regulation, and genetics of bile acid synthesis. Annu Rev Biochem. 2003;72:137-74. doi: 10.1146/annurev.biochem.72.121801.161712. Epub 2003 Jan 16. [PubMed:12543708 ]

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