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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-14 18:03:00 UTC
Update Date2021-09-14 15:37:24 UTC
HMDB IDHMDB0006889
Secondary Accession Numbers
  • HMDB06889
Metabolite Identification
Common Name3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA
Description3alpha,7alpha,12alpha-Trihydroxy-5beta-cholest-24-enoyl-CoA is an intermediate in bile acid synthesis. 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. 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?1582752413
Synonyms
ValueSource
(24E)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholest-24-enoyl-CoAHMDB
(24E)-3-alpha,7-alpha,12-alpha-Trihydroxy-5-beta-cholest-24-enoyl-coenzyme AHMDB
3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl CoAHMDB
3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl coenzyme AHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholest-24-enoyl CoAHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholest-24-enoyl coenzyme AHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholest-24-enoyl-CoAHMDB
3alpha,7alpha,12alpha-Trihydroxy-5beta-cholest-24-enoyl-coenzyme AHMDB
Chemical FormulaC48H78N7O20P3S
Average Molecular Weight1198.154
Monoisotopic Molecular Weight1197.423518197
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-{[(2E)-2-methyl-6-[(5R,7S,9R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]hept-2-enoyl]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-{[(2E)-2-methyl-6-[(5R,7S,9R,16S)-5,9,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]hept-2-enoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CC(CC\C=C(/C)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N)C1CCC2C3[C@H](O)C[C@]4([H])C[C@H](O)CCC4(C)C3C[C@H](O)C12C
InChI Identifier
InChI=1S/C48H78N7O20P3S/c1-25(29-10-11-30-36-31(20-34(58)48(29,30)6)47(5)14-12-28(56)18-27(47)19-32(36)57)8-7-9-26(2)45(63)79-17-16-50-35(59)13-15-51-43(62)40(61)46(3,4)22-72-78(69,70)75-77(67,68)71-21-33-39(74-76(64,65)66)38(60)44(73-33)55-24-54-37-41(49)52-23-53-42(37)55/h9,23-25,27-34,36,38-40,44,56-58,60-61H,7-8,10-22H2,1-6H3,(H,50,59)(H,51,62)(H,67,68)(H,69,70)(H2,49,52,53)(H2,64,65,66)/b26-9+/t25?,27-,28+,29?,30?,31?,32+,33+,34-,36?,38+,39+,40?,44+,47?,48?/m0/s1
InChI KeyQVDPWQVOSKJUES-WYOYJMLVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Steroidal glycoside
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • Trihydroxy bile acid, alcohol, or derivatives
  • Hydroxy bile acid, alcohol, or derivatives
  • Cholane-skeleton
  • Bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • 12-hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • Steroid
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • 6-aminopurine
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Pyrimidine
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Imidolactam
  • Tetrahydrofuran
  • Imidazole
  • Cyclic alcohol
  • Azole
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Thiocarboxylic acid ester
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Thiocarboxylic acid or derivatives
  • Polyol
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.52 g/LALOGPS
logP10(1.22) g/LALOGPS
logP10(-2.8) g/LChemAxon
logS10(-3.4) g/LALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area424.32 ŲChemAxon
Rotatable Bond Count25ChemAxon
Refractivity285.01 m³·mol⁻¹ChemAxon
Polarizability118.38 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 10V, Positive-QTOFsplash10-01p9-1900011000-917cfa4c7b116561ee572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 20V, Positive-QTOFsplash10-000i-0900225000-6e0ac93627398227776b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 40V, Positive-QTOFsplash10-000i-1900011000-2e57b689af259bc8051e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 10V, Negative-QTOFsplash10-0059-2900431400-0bd7bf13fa651accbe162017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 20V, Negative-QTOFsplash10-003r-3900221010-850345d2152a4932c39f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-337254c96245435a4dd92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 10V, Negative-QTOFsplash10-0002-0900000000-2b1caba33cb107587cc82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 20V, Negative-QTOFsplash10-004j-3600902200-466a26d0fe4dcf607a852021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 40V, Negative-QTOFsplash10-014r-6204604900-3fefff921e645cdbdc792021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 10V, Positive-QTOFsplash10-0002-0900000000-5bf7a798fa3aed31bdf42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 20V, Positive-QTOFsplash10-000i-0910001300-e71d11466a64ae6f0ad22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA 40V, Positive-QTOFsplash10-0006-0000119000-4a24adf2255bd4e3a5ae2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024136
KNApSAcK IDNot Available
Chemspider ID4444355
KEGG Compound IDC05460
BioCyc IDNot Available
BiGG ID45854
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5280797
PDB IDNot Available
ChEBI ID27505
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 acyl-CoA dehydrogenase activity
Specific function:
Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:
ACOX2
Uniprot ID:
Q99424
Molecular weight:
76826.14
Reactions
(25S)-3alpha,7alpha,12alpha-Trihydroxy-5beta-cholestan-26-oyl-CoA + Acceptor → 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA + Reduced acceptordetails
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 → 3a,7a,12a-Trihydroxy-5b-cholest-24-enoyl-CoA + Waterdetails