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
StatusExpected but not Quantified
Creation Date2009-07-13 13:21:08 UTC
Update Date2017-12-07 02:37:49 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
Thumb
SynonymsNot Available
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
DescriptionThis compound belongs to the class of chemical entities known as 3-hydroxyacyl coas. These are organic compounds containing a 3-hydroxyl acylated coenzyme A derivative.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct Parent3-hydroxyacyl 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
  • 24-hydroxysteroid
  • Hydroxy bile acid, alcohol, or derivatives
  • Cholane-skeleton
  • Bile acid, alcohol, or derivatives
  • 7-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 3-hydroxysteroid
  • Steroid
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Fatty amide
  • Alkyl phosphate
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Phosphoric acid ester
  • Primary aromatic amine
  • Imidolactam
  • Azole
  • Tetrahydrofuran
  • Cyclic alcohol
  • Imidazole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Thiocarboxylic acid ester
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Thiocarboxylic acid or derivatives
  • Sulfenyl compound
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Organooxygen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

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 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
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, Positivesplash10-01p9-1900012000-622aba437f7430e017fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900225000-2ec5547c65b2f24e0c94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900011000-ed3cd21797c8357fb61cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2900432410-2a5b364cc28a01f6501bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3900121010-4fe3346cb382c95a93b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900100000-fd2f0a5af0fa8cb2631cView in MoNA
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
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 IDFDB029072
KNApSAcK IDNot Available
Chemspider ID389554
KEGG Compound IDC05448
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440675
PDB IDNot Available
ChEBI ID27403
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