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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-08-16 14:44:11 UTC
Update Date2022-03-07 02:49:09 UTC
HMDB IDHMDB0001419
Secondary Accession Numbers
  • HMDB01419
Metabolite Identification
Common Name24-Hydroxycholesterol
Description24-Hydroxycholesterol (24OHC) is almost exclusively formed in the brain. The enzymatic conversion of CNS cholesterol to 24OHC, which readily crosses the blood-brain barrier, is the major pathway for brain cholesterol elimination and brain cholesterol homeostasis maintenance. The enzyme mediating this conversion has been characterized at the molecular level as cholesterol 24-hydroxylase (EC 1.14.13.98, CYP46) and is mainly located in neurons. Like other oxysterols, 24OHC is efficiently converted into normal bile acids or excreted in bile in its sulfated and glucuronidated form. Levels of 24OHC in the circulation decrease with age in infants and children. In adults, however, the levels appear to be stable. There is accumulating evidence pointing toward a potentially important link between cholesterol, beta-amyloid, and Alzheimer's disease. Patients with active demyelinating diseases had increased levels of 24OHC in cerebrospinal fluid (CSF). Patients with Alzheimer's disease have slightly increased levels of 24OHC in CSF. Patients with multiple sclerosis have a tendency to have higher levels of 24OHC during active periods. (PMID: 15061359 , 14574622 ). 24-Hydroxycholesterol has been found to accumulate in hereditary hypercholesterolemia, an inborn error of metabolism.
Structure
Data?1582752199
Synonyms
ValueSource
(24S)-HydroxycholesterolChEBI
24S-Hydroxy-cholesterolChEBI
CerebrosterolChEBI
Cholest-5-en-3beta,24S-diolChEBI
Cholest-5-ene-3,24-diolChEBI
(24S)-24-HydroxycholesterolKegg
(24S)-Cholest-5-ene-3beta,24-diolKegg
Cholest-5-en-3b,24S-diolGenerator
Cholest-5-en-3β,24S-diolGenerator
(24S)-Cholest-5-ene-3b,24-diolGenerator
(24S)-Cholest-5-ene-3β,24-diolGenerator
24(S)-HydroxycholesterolHMDB
24S-Cholest-5-ene-3b,24-diolHMDB
24S-HydroxycholesterolHMDB
CerebrosterinHMDB
Cholest-5-ene-3b,24b-diolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name24(S)-hydroxycholesterol
CAS Registry Number474-73-7
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C
InChI Identifier
InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1
InChI KeyIOWMKBFJCNLRTC-XWXSNNQWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydroxy bile acids, alcohols and derivatives. Dihydroxy bile acids, alcohols and derivatives are compounds containing or derived from a bile acid or alcohol, and which bears exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentDihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • 24-hydroxysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Biological locationRoute of exposureSource
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 Solubility0.0004 g/LALOGPS
logP5.7ALOGPS
logP5.8ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.95ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.21 m³·mol⁻¹ChemAxon
Polarizability51.14 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+197.43231661259
DarkChem[M-H]-192.66631661259
AllCCS[M+H]+206.49932859911
AllCCS[M-H]-203.36832859911
DeepCCS[M-2H]-237.52130932474
DeepCCS[M+Na]+211.72330932474
AllCCS[M+H]+206.532859911
AllCCS[M+H-H2O]+204.432859911
AllCCS[M+NH4]+208.432859911
AllCCS[M+Na]+209.032859911
AllCCS[M-H]-203.432859911
AllCCS[M+Na-2H]-205.332859911
AllCCS[M+HCOO]-207.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
24-Hydroxycholesterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C2662.9Standard polar33892256
24-Hydroxycholesterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C3293.8Standard non polar33892256
24-Hydroxycholesterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CC[C@H](O)C(C)C3443.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
24-Hydroxycholesterol,1TMS,isomer #1CC(C)[C@@H](O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3400.9Semi standard non polar33892256
24-Hydroxycholesterol,1TMS,isomer #2CC(C)[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)O[Si](C)(C)C3376.0Semi standard non polar33892256
24-Hydroxycholesterol,2TMS,isomer #1CC(C)[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)O[Si](C)(C)C3407.5Semi standard non polar33892256
24-Hydroxycholesterol,1TBDMS,isomer #1CC(C)[C@@H](O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3618.3Semi standard non polar33892256
24-Hydroxycholesterol,1TBDMS,isomer #2CC(C)[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]21C)O[Si](C)(C)C(C)(C)C3630.0Semi standard non polar33892256
24-Hydroxycholesterol,2TBDMS,isomer #1CC(C)[C@H](CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C)O[Si](C)(C)C(C)(C)C3901.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 24-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0076-1009000000-ab69a48110c4082d2ca72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positivesplash10-001i-2111290000-94668570804377216a372017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 24-Hydroxycholesterol 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 - 24-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0003900000-db2e1b276e6052150b6f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 20V, Negative-QTOFsplash10-0ue9-0009700000-55fe1a48489ad8aa8bb62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 40V, Negative-QTOFsplash10-00ri-7009000000-7a2a5d9fa1c30ba0c55b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 20V, Negative-QTOFsplash10-0udi-0003900000-390ce6ee953a3d06105b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 40V, Negative-QTOFsplash10-0002-0009000000-b4881863f9f5f7cd22232021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 10V, Positive-QTOFsplash10-0f79-0009200000-0f92e092c978feb7ef4a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 20V, Positive-QTOFsplash10-00kr-4119100000-6a8569b9873ebded521a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 40V, Positive-QTOFsplash10-0c01-5049000000-3466fdb5c0a23399bea32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 10V, Positive-QTOFsplash10-00ku-0209100000-bfd7a93b49439544b96f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 20V, Positive-QTOFsplash10-090u-5459000000-c9b30378df2d7c3e159c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 24-Hydroxycholesterol 40V, Positive-QTOFsplash10-0a4l-6940000000-78cdb9ace90e3772c7c22021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.049 +/- 0.002 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.006 +/- 0.0003 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0018 +/- 0.00052 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.191 +/- 0.00993 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0034 (0.0033-0.0036) uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.11 +/- 0.03 uMAdult (>18 years old)Not Specified
Hypercholesterolemia
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0061 (0.0058-0.0064) uMElderly (>65 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.016 (0.014-0.017) uMAdult (>18 years old)BothAcute or chronic demyelinating polyneuropathies details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0045 (0.0041-0.0050) uMAdult (>18 years old)BothSubarachnoid hemorrhage details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0086 (0.0076-0.0096) uMAdult (>18 years old)Both
Meningitis
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0062 (0.0057-0.0068) uMAdult (>18 years old)BothNeuroborreliosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0077 (0.0066-0.0093) uMAdult (>18 years old)Not Specified
Mild cognitive impairment
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.004 +/- 0.0013 uMAdult (>18 years old)BothMultiple Sclerosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothInflammatory bowel disease details
Associated Disorders and Diseases
Disease References
Hypercholesterolemia
  1. Thelen KM, Laaksonen R, Paiva H, Lehtimaki T, Lutjohann D: High-dose statin treatment does not alter plasma marker for brain cholesterol metabolism in patients with moderately elevated plasma cholesterol levels. J Clin Pharmacol. 2006 Jul;46(7):812-6. [PubMed:16809807 ]
Alzheimer's disease
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Demyelinating polyneuropathy
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Subarachnoid hemorrhage
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Meningitis
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Neuroborreliosis
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Mild cognitive impairment
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
Multiple sclerosis
  1. Leoni V, Lutjohann D, Masterman T: Levels of 7-oxocholesterol in cerebrospinal fluid are more than one thousand times lower than reported in multiple sclerosis. J Lipid Res. 2005 Feb;46(2):191-5. Epub 2004 Dec 1. [PubMed:15576852 ]
Inflammatory bowel disease
  1. Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022611
KNApSAcK IDNot Available
Chemspider ID108790
KEGG Compound IDC13550
BioCyc IDNot Available
BiGG ID2197434
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound121948
PDB IDNot Available
ChEBI ID34310
Food Biomarker OntologyNot Available
VMH IDXOL24OH
MarkerDB IDMDB00000322
Good Scents IDNot Available
References
Synthesis ReferencePrasad V V; Ponticorvo L; Lieberman S Identification of 24-hydroxycholesterol in bovine adrenals in both free and esterified forms and in bovine brains as its sulfate ester. Journal of steroid biochemistry (1984), 21(6), 733-6.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Leoni V, Masterman T, Mousavi FS, Wretlind B, Wahlund LO, Diczfalusy U, Hillert J, Bjorkhem I: Diagnostic use of cerebral and extracerebral oxysterols. Clin Chem Lab Med. 2004 Feb;42(2):186-91. [PubMed:15061359 ]
  2. Lutjohann D, von Bergmann K: 24S-hydroxycholesterol: a marker of brain cholesterol metabolism. Pharmacopsychiatry. 2003 Sep;36 Suppl 2:S102-6. [PubMed:14574622 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Involved in the turnover of cholesterol. It converts cholesterol into 24S-hydroxycholesterol and, to a lesser extent, 25-hydroxycholesterol.
Gene Name:
CYP46A1
Uniprot ID:
Q9Y6A2
Molecular weight:
56820.535
Reactions
Cholesterol + NADPH + Oxygen → 24-Hydroxycholesterol + NADP + Waterdetails