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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-23 04:39:03 UTC
Update Date2022-03-07 03:17:57 UTC
HMDB IDHMDB0062607
Secondary Accession Numbers
  • HMDB62607
Metabolite Identification
Common Name(25R)-4beta,26-dihydroxycholesterol
Description(25R)-4beta,26-dihydroxycholesterol, also known as (3b,4b,25R)-cholest-5-ene-3,4,26-triol, belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups (25R)-4beta,26-dihydroxycholesterol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563866335
Synonyms
ValueSource
(3beta,4beta,25R)-Cholest-5-ene-3,4,26-triolChEBI
(3b,4b,25R)-Cholest-5-ene-3,4,26-triolGenerator
(3Β,4β,25R)-cholest-5-ene-3,4,26-triolGenerator
(25R)-4b,26-DihydroxycholesterolGenerator
(25R)-4Β,26-dihydroxycholesterolGenerator
Chemical FormulaC27H46O3
Average Molecular Weight418.662
Monoisotopic Molecular Weight418.344695341
IUPAC Name(1S,2R,5S,6R,10S,11S,14R,15R)-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,6-diol
Traditional Name(1S,2R,5S,6R,10S,11S,14R,15R)-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,6-diol
CAS Registry NumberNot Available
SMILES
[H][C@](C)(CO)CCC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4[C@@]([H])(O)[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
InChI Identifier
InChI=1S/C27H46O3/c1-17(16-28)6-5-7-18(2)20-10-11-21-19-8-9-23-25(30)24(29)13-15-27(23,4)22(19)12-14-26(20,21)3/h9,17-22,24-25,28-30H,5-8,10-16H2,1-4H3/t17-,18-,19+,20-,21+,22+,24+,25-,26-,27-/m1/s1
InChI KeyIDLRVFXWSUWMHI-KUYJPBLDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 26-hydroxysteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 4-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Delta-5-steroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0032 g/lALOGPS
LogP5.28ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP5.28ALOGPS
logP4.84ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.5ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity123.68 m³·mol⁻¹ChemAxon
Polarizability52.52 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.8931661259
DarkChem[M-H]-200.88631661259
DeepCCS[M-2H]-225.66330932474
DeepCCS[M+Na]+199.71630932474
AllCCS[M+H]+208.632859911
AllCCS[M+H-H2O]+206.632859911
AllCCS[M+NH4]+210.332859911
AllCCS[M+Na]+210.832859911
AllCCS[M-H]-204.032859911
AllCCS[M+Na-2H]-206.132859911
AllCCS[M+HCOO]-208.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(25R)-4beta,26-dihydroxycholesterol[H][C@](C)(CO)CCC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4[C@@]([H])(O)[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C2757.3Standard polar33892256
(25R)-4beta,26-dihydroxycholesterol[H][C@](C)(CO)CCC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4[C@@]([H])(O)[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C3569.1Standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol[H][C@](C)(CO)CCC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4[C@@]([H])(O)[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C3653.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(25R)-4beta,26-dihydroxycholesterol,1TMS,isomer #1C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C3571.8Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,1TMS,isomer #2C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3484.5Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,1TMS,isomer #3C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3519.9Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,2TMS,isomer #1C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C3485.3Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,2TMS,isomer #2C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C3528.7Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,2TMS,isomer #3C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3430.5Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,3TMS,isomer #1C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C3452.3Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,1TBDMS,isomer #1C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C3829.8Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,1TBDMS,isomer #2C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C3726.4Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,1TBDMS,isomer #3C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3741.2Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,2TBDMS,isomer #1C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C3976.4Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,2TBDMS,isomer #2C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C4000.2Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,2TBDMS,isomer #3C[C@@H](CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3868.0Semi standard non polar33892256
(25R)-4beta,26-dihydroxycholesterol,3TBDMS,isomer #1C[C@H](CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)CO[Si](C)(C)C(C)(C)C4109.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (25R)-4beta,26-dihydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0k9i-0009200000-d93e1c414854aa50ceb02017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (25R)-4beta,26-dihydroxycholesterol GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-1200149000-54e7c684d5212de100202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (25R)-4beta,26-dihydroxycholesterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 10V, Positive-QTOFsplash10-0uxr-0003900000-880dde1d8f940fa8a49c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 20V, Positive-QTOFsplash10-0ue9-2109400000-35e10c2e3d6c33f417ea2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 40V, Positive-QTOFsplash10-066r-4229100000-fed098f417df535abe722017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0003900000-d06172d5c6dcfa8ed5682017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 20V, Negative-QTOFsplash10-014j-0009700000-98f1250d2989694982972017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 40V, Negative-QTOFsplash10-05g0-2009100000-452630452c3b7991905a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 10V, Positive-QTOFsplash10-0gc0-1004900000-6926c7d49d034235f86f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 20V, Positive-QTOFsplash10-001i-9237300000-428551f4a4c2435f43a72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 40V, Positive-QTOFsplash10-0a6r-9630000000-8ae927dd6843bcc0eb662021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 10V, Negative-QTOFsplash10-014i-0001900000-16e558fdd81b58b0dee82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 20V, Negative-QTOFsplash10-014i-0004900000-05c63be805106eccc9c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (25R)-4beta,26-dihydroxycholesterol 40V, Negative-QTOFsplash10-014i-0001900000-d8eadcf03e567a7a3db52021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound91825745
PDB IDNot Available
ChEBI ID86113
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. Bodin K, Andersson U, Rystedt E, Ellis E, Norlin M, Pikuleva I, Eggertsen G, Bjorkhem I, Diczfalusy U: Metabolism of 4 beta -hydroxycholesterol in humans. J Biol Chem. 2002 Aug 30;277(35):31534-40. Epub 2002 Jun 20. [PubMed:12077124 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.