You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2008-08-14 18:08:34 UTC
Update Date2017-09-21 21:39:17 UTC
HMDB IDHMDB0006891
Secondary Accession Numbers
  • HMDB06891
Metabolite Identification
Common Name3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA
Description3alpha,7alpha,12alpha-Trihydroxy-5beta-24-oxocholestanoyl-CoA is an intermediate in bile acid synthesis. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 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
Thumb
Synonyms
ValueSource
(24R,25R)-3-alpha,7-alpha,12-alpha,24-Tetrahydroxy-5-beta-cholestan-26-oyl-CoAHMDB
(24R,25R)-3-alpha,7-alpha,12-alpha,24-Tetrahydroxy-5-beta-cholestan-26-oyl-coenzyme AHMDB
24-oxo-25(R)-Trihydroxycoprostanoyl-CoAHMDB
24-oxo-25(R)-Trihydroxycoprostanoyl-coenzyme AHMDB
25(R)-24-oxo-3alpha,7alpha,12alpha-Trihydroxycoprostanoyl-CoAHMDB
25(R)-24-oxo-3alpha,7alpha,12alpha-Trihydroxycoprostanoyl-coenzyme AHMDB
25(R)-3alpha,7alpha,12alpha-Trihydroxy-24-oxo-5beta-cholestanoyl-CoAHMDB
25(R)-3alpha,7alpha,12alpha-Trihydroxy-24-oxo-5beta-cholestanoyl-coenzyme AHMDB
25(R)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-24-on-26-oyl-CoAHMDB
25(R)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-24-on-26-oyl-coenzyme AHMDB
25(R)-5beta-Cholestane-3alpha,7alpha,12alpha-triol-24-on-26-oyl-CoAHMDB
25(R)-5beta-Cholestane-3alpha,7alpha,12alpha-triol-24-on-26-oyl-coenzyme AHMDB
3-alpha,7-alpha,12-alpha,24-Tetrahydroxy-5-beta-cholestan-26-oyl-CoAHMDB
3-alpha,7-alpha,12-alpha,24-Tetrahydroxy-5-beta-cholestan-26-oyl-coenzyme AHMDB
3-alpha,7-alpha,12-alpha-Trihydroxy-24-oxo-5-beta-cholestanoyl-CoAHMDB
3-alpha,7-alpha,12-alpha-Trihydroxy-24-oxo-5-beta-cholestanoyl-coenzyme AHMDB
3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-coenzyme AHMDB
3alpha,7alpha,12alpha-Trihydroxy-24-oxo-5beta-cholestanoyl-CoAHMDB
3alpha,7alpha,12alpha-Trihydroxy-24-oxo-5beta-cholestanoyl-coenzyme AHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-24-oxocholestanoyl-CoAHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-24-oxocholestanoyl-coenzyme AHMDB
R-TrHOCCoAHMDB
R-TrHOCcoenzyme AHMDB
Chemical FormulaC48H78N7O21P3S
Average Molecular Weight1214.154
Monoisotopic Molecular Weight1213.418432819
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({3-hydroxy-2,2-dimethyl-3-[(2-{[2-({2-methyl-3-oxo-6-[(1S,5R,7S,9R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy})phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-({2-methyl-3-oxo-6-[(1S,5R,7S,9R,11S,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC(C(C)CCC(=O)C(C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3OP(O)(O)=O)N3C=NC4=C3N=CN=C4N)C1(C)[C@@H](O)C[C@@]1([H])C2[C@H](O)C[C@]2([H])C[C@H](O)CCC12C
InChI Identifier
InChI=1S/C48H78N7O21P3S/c1-24(28-8-9-29-36-30(19-34(59)48(28,29)6)47(5)13-11-27(56)17-26(47)18-32(36)58)7-10-31(57)25(2)45(64)80-16-15-50-35(60)12-14-51-43(63)40(62)46(3,4)21-73-79(70,71)76-78(68,69)72-20-33-39(75-77(65,66)67)38(61)44(74-33)55-23-54-37-41(49)52-22-53-42(37)55/h22-30,32-34,36,38-40,44,56,58-59,61-62H,7-21H2,1-6H3,(H,50,60)(H,51,63)(H,68,69)(H,70,71)(H2,49,52,53)(H2,65,66,67)/t24?,25?,26-,27+,28?,29-,30-,32+,33+,34-,36?,38+,39+,40?,44+,47?,48?/m0/s1
InChI KeyAWLXQJGPNLCTLM-XFQWJXLTSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 3-oxo-acyl coas. These are organic compounds containing a 3-oxo acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-oxo-acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Steroidal glycoside
  • Trihydroxy bile acid, alcohol, or derivatives
  • 24-oxosteroid
  • Hydroxy bile acid, alcohol, or derivatives
  • Cholane-skeleton
  • Bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Steroid
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Phosphoric acid ester
  • Pyrimidine
  • Fatty amide
  • 1,3-dicarbonyl compound
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Imidolactam
  • Azole
  • Cyclic alcohol
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • Thiocarboxylic acid ester
  • Ketone
  • Amino acid or derivatives
  • Secondary alcohol
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carbothioic s-ester
  • Polyol
  • Organoheterocyclic compound
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Oxacycle
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary amine
  • Amine
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 mg/mLALOGPS
logP0.82ALOGPS
logP-3.5ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count21ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area441.39 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity284.82 m3·mol-1ChemAxon
Polarizability119.51 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
27-Hydroxylase DeficiencyPw000697Pw000697 greyscalePw000697 simpleNot Available
Bile Acid BiosynthesisPw000145Pw000145 greyscalePw000145 simpleMap00120
Cerebrotendinous Xanthomatosis (CTX)Pw000196Pw000196 greyscalePw000196 simpleNot Available
Congenital Bile Acid Synthesis Defect Type IIPw000192Pw000192 greyscalePw000192 simpleNot Available
Congenital Bile Acid Synthesis Defect Type IIIPw000193Pw000193 greyscalePw000193 simpleNot Available
Displaying entries 1 - 5 of 7 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024138
KNApSAcK IDNot Available
Chemspider ID389566
KEGG Compound IDC05467
BioCyc IDNot Available
BiGG ID45868
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0006891
METLIN IDNot Available
PubChem Compound440690
PDB IDNot Available
ChEBI ID27379
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]

Enzymes

General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:
ACAA2
Uniprot ID:
P42765
Molecular weight:
41923.82
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
ACAA1
Uniprot ID:
P09110
Molecular weight:
34664.46
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Not Available
Gene Name:
HADHB
Uniprot ID:
P55084
Molecular weight:
51293.955
General function:
Involved in oxidoreductase activity
Specific function:
Mediates in vitro the transfer of all common phospholipids, cholesterol and gangliosides between membranes. May play a role in regulating steroidogenesis.
Gene Name:
SCP2
Uniprot ID:
P22307
Molecular weight:
34974.505
Reactions
Propionyl-CoA + Choloyl-CoA → Coenzyme A + 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoAdetails
General function:
Involved in oxidoreductase activity
Specific function:
Bifunctional enzyme acting on the peroxisomal beta-oxidation pathway for fatty acids. Catalyzes the formation of 3-ketoacyl-CoA intermediates from both straight-chain and 2-methyl-branched-chain fatty acids.
Gene Name:
HSD17B4
Uniprot ID:
P51659
Molecular weight:
79685.715
Reactions
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoyl-CoA + NAD → 3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Does not exhibit retinol dehydrogenase (RDH) activity in vitro
Gene Name:
RDH13
Uniprot ID:
Q8NBN7
Molecular weight:
35931.8