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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-13 13:21:08 UTC
Update Date2022-03-07 02:51:26 UTC
HMDB IDHMDB0012456
Secondary Accession Numbers
  • HMDB12456
Metabolite Identification
Common Name3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA
Description3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA is found in the primary bile acid biosynthesis pathway. 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA is created from 3 alpha,7 alpha-Dihydroxy-5beta-cholest-24-enoyl-CoA through the action of HSD17B4 (EC4.2.1.107). 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA is then converted to 3 alpha,7 alpha-Dihydroxy-5beta-24-oxocholestanoyl-CoA by HSD17B4 (EC1.1.1.35).
Structure
Data?1582753057
Synonyms
ValueSource
3alpha,7alpha,24-Trihydroxy-5beta-cholestan-26-oyl-coenzyme AChEBI
3alpha,7alpha,24-Trihydroxy-5beta-cholestanoyl-CoAChEBI
(24R,25R)-3alpha,7alpha,24-Trihydroxy-5beta-cholestan-26-oyl-CoAKegg
3a,7a,24-Trihydroxy-5b-cholestan-26-oyl-coenzyme AGenerator
3Α,7α,24-trihydroxy-5β-cholestan-26-oyl-coenzyme AGenerator
3a,7a,24-Trihydroxy-5b-cholestanoyl-CoAGenerator
3Α,7α,24-trihydroxy-5β-cholestanoyl-CoAGenerator
(24R,25R)-3a,7a,24-Trihydroxy-5b-cholestan-26-oyl-CoAGenerator
(24R,25R)-3Α,7α,24-trihydroxy-5β-cholestan-26-oyl-CoAGenerator
3 a,7 a,24-Trihydroxy-5b-cholestanoyl-CoAGenerator
3 Α,7 α,24-trihydroxy-5β-cholestanoyl-CoAGenerator
Chemical FormulaC48H80N7O20P3S
Average Molecular Weight1200.17
Monoisotopic Molecular Weight1199.439168261
IUPAC Name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-3-hydroxy-2-methylheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-({6-[(2S,5R,7S,9R,15R)-5,9-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]-3-hydroxy-2-methylheptanoyl}sulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]12C[C@H](O)CC[C@]1(C)C1CC[C@]3(C)C(CCC3C1[C@H](O)C2)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]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C48H80N7O20P3S/c1-25(29-8-9-30-36-31(12-15-48(29,30)6)47(5)14-11-28(56)19-27(47)20-33(36)58)7-10-32(57)26(2)45(63)79-18-17-50-35(59)13-16-51-43(62)40(61)46(3,4)22-72-78(69,70)75-77(67,68)71-21-34-39(74-76(64,65)66)38(60)44(73-34)55-24-54-37-41(49)52-23-53-42(37)55/h23-34,36,38-40,44,56-58,60-61H,7-22H2,1-6H3,(H,50,59)(H,51,62)(H,67,68)(H,69,70)(H2,49,52,53)(H2,64,65,66)/t25?,26?,27-,28+,29?,30?,31?,32?,33+,34+,36?,38+,39+,40?,44+,47-,48+/m0/s1
InChI KeySZBMUAIJWNJARR-ATZLTZGYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent3-hydroxyacyl 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-hydroxysteroid
  • Hydroxy bile acid, alcohol, or derivatives
  • Cholane-skeleton
  • Bile acid, alcohol, or derivatives
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 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
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Pyrimidine
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • Phosphoric acid ester
  • N-substituted imidazole
  • Imidolactam
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Azole
  • Tetrahydrofuran
  • Cyclic alcohol
  • Imidazole
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Carbothioic s-ester
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Thiocarboxylic acid ester
  • Oxacycle
  • Azacycle
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Primary amine
  • Alcohol
  • Organosulfur compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.71 g/LALOGPS
logP1.24ALOGPS
logP-2.8ChemAxon
logS-3.2ALOGPS
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 Count26ChemAxon
Refractivity284.13 m³·mol⁻¹ChemAxon
Polarizability119.5 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-330.30830932474
DeepCCS[M+Na]+304.83930932474
AllCCS[M+H]+320.632859911
AllCCS[M+H-H2O]+321.332859911
AllCCS[M+NH4]+320.132859911
AllCCS[M+Na]+319.932859911
AllCCS[M-H]-267.332859911
AllCCS[M+Na-2H]-272.632859911
AllCCS[M+HCOO]-278.432859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 10V, Positive-QTOFsplash10-01p9-1900012000-622aba437f7430e017fb2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 20V, Positive-QTOFsplash10-000i-0900225000-2ec5547c65b2f24e0c942017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 40V, Positive-QTOFsplash10-000i-1900011000-ed3cd21797c8357fb61c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 10V, Negative-QTOFsplash10-001i-2900432410-2a5b364cc28a01f6501b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 20V, Negative-QTOFsplash10-001i-3900121010-4fe3346cb382c95a93b62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-fd2f0a5af0fa8cb2631c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 10V, Negative-QTOFsplash10-0002-0900000000-65cf19f1888cb6ceb8382021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 20V, Negative-QTOFsplash10-000t-1900301100-c1a7499a6c8ed6e7c77c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 40V, Negative-QTOFsplash10-05ra-5603903700-dc786a780fcf9d33e01b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 10V, Positive-QTOFsplash10-0ue9-0890000000-de8bcb28860c798ed88e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 20V, Positive-QTOFsplash10-03el-0910000030-ef9afdd365f76dc605db2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA 40V, Positive-QTOFsplash10-0006-0000019000-74c41a4f5ab647d8c2772021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID26333133
KEGG Compound IDC05448
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound46224536
PDB IDNot Available
ChEBI ID27403
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

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-Dihydroxy-5b-cholest-24-enoyl-CoA + Water → 3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoAdetails
3 alpha,7 alpha,24-Trihydroxy-5beta-cholestanoyl-CoA + NAD → 3a,7a-Dihydroxy-5b-24-oxocholestanoyl-CoA + NADH + Hydrogen Iondetails