3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA (CHEM036296)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:21:33 UTC
Update Date2016-11-09 01:21:28 UTC
Accession NumberCHEM036296
Identification
Common Name3a,7a,12a-Trihydroxy-5b-24-oxocholestanoyl-CoA
ClassSmall Molecule
Description3a,7a,12a-Trihydroxy-5b-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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass1214.154 g/mol
Monoisotopic Mass1213.418 g/mol
CAS Registry NumberNot Available
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
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 IdentifierInChI=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
Description 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity284.82 m³·mol⁻¹ChemAxon
Polarizability119.51 ųChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900021100-1fa27e81efdfbc149a98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0901132200-5bfed04a7e4f8df63c6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900010100-143578d6a5db8c5e2f2aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00o3-2920642500-18048f2816bacc2e9219Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3900221010-e4389ba87591b7d47d8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-52d44b7b806816c6bd25Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0290000000-b7a8c3cc183e58c433cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fu-4770903201-11227f4a396a48a9490fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0170-5122603900-a7af28ea3503a097e921Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0691000000-af68373f9dfb1b8e7ba0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-0951000001-1bcadd0a7e2bbc25d9b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0100000900-226355700f943a61d138Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006891
FooDB IDFDB024138
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID45868
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID389566
ChEBI ID27379
PubChem Compound ID440690
Kegg Compound IDC05467
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot 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.
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.
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.
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.