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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:36 UTC
Update Date2022-03-07 02:49:12 UTC
HMDB IDHMDB0002103
Secondary Accession Numbers
  • HMDB0062328
  • HMDB02103
  • HMDB62328
Metabolite Identification
Common Name27-Hydroxycholesterol
Description27-Hydroxycholesterol (27-HC), also known as (25R)-cholest-5-ene-3β,26-diol or by its conventional name 26-hydroxycholesterol, is an oxygenated derivative of cholesterol and a major oxysterol in circulation (PMID: 7749852 ). 27-Hydroxycholesterol is the product of the enzyme sterol 27-hydroxylase. The enzyme is critical for the degradation of the steroid side-chain and a genetic deficiency of the enzyme leads to reduced formation of bile acids in humans. There is a correlation between 27-hydroxycholesterol and cholesterol in the circulation, and females have lower levels of 27-hydroxycholesterol than males. A strong correlation is observed between circulating levels of 27-hydroxycholesterol and cholesterol, in both healthy subjects and subjects with hypercholesterolemia and documented atherosclerosis. 27-Hydroxycholesterol is metabolized by an oxysterol 7alpha-hydroxylase in the liver. Changes in the activity of this enzyme may lead to the accumulation of 27-hydroxycholesterol in the circulation. It has been reported that patients with a genetic deficiency of oxysterol 7alpha-hydroxylase in the liver had markedly increased levels of 27-hydroxycholesterol in the circulation. However, under normal conditions and in the absence of liver or kidney disease, changes in the levels of 27-hydroxycholesterol in the circulation are likely to be caused by changes in the rate of synthesis of these steroids rather than by the rate of metabolism. There are three possible explanations for the high concentrations of 27-hydroxycholesterol found in the circulation of three subjects with atherosclerosis: (1) increased expression of sterol 27-hydroxylase owing to a genetic factor or some other factor completely unrelated to atherosclerosis, (2) the extrahepatic sterol 27-hydroxylase may be up-regulated by circulating factors (e.g. cytokines) that are directly or indirectly related to the development of atherosclerosis, and (3) the high amounts of cholesterol accumulating in macrophages in some patients with atherosclerosis may result in an increased flux of 27-hydroxycholesterol from the macrophages to the circulation. Since there is a close relation between levels of cholesterol and 27-hydroxycholesterol in the circulation, the possibility must be considered that the flux of 27-hydroxycholesterol into the brain may be part of the yet unexplained link between hypercholesterolemia and Alzheimer's disease. 27-Hydroxysterol is the most dominant oxysterol in human atheromas where it may reflect a mechanism for eliminating excessive cholesterol, and thus have a protective role. Hypercholesterolemia and chronic low-grade immunological activation are pivotal in the development of atherosclerosis. However, the interconnections between these two factors are not well known. The CD40 system, as measured by the plasma level of soluble CD40 (sCD40), is associated with cholesterol metabolism in hypercholesterolemic patients. When combined, a decreased cholesterol synthesis rate and increased levels of 27-hydroxycholesterol may be a consequence of high levels of cellular cholesterol, and therefore be related to sCD40. However, sCD40 had no significant correlation with total plasma cholesterol. This suggests that the cellular cholesterol synthesis rate and 27-hydroxycholesterol production are more importantly linked with the plasma levels of sCD40 than total cholesterol (PMID: 16081359 , 17012138 , 11504730 , 9144161 ).
Structure
Data?1582752229
Synonyms
ValueSource
(25R)-26-HydroxycholesterolChEBI
5-Cholestene-3beta,27-diolChEBI
Cholest-5-ene-3beta,27-diolChEBI
5-Cholestene-3b,27-diolGenerator
5-Cholestene-3β,27-diolGenerator
Cholest-5-ene-3b,27-diolGenerator
Cholest-5-ene-3β,27-diolGenerator
(25R)-Cholest-5-ene-3b,26-diolHMDB
(25R)-Cholest-5-ene-3beta,26-diolHMDB
(3-beta)-Cholest-5-ene-3,26-diolHMDB
(3b,25R)-Cholest-5-ene-3,26-diolHMDB
(3beta,25R)-Cholest-5-ene-3,26,diolHMDB
26-Hydroxycholesterol(25R)HMDB
Cholest-(25R)-5-en-3beta,26-diolHMDB
Cholest-5-ene-3-b,27-diolHMDB
Cholest-5-ene-3-beta,26-diolHMDB
Cholest-5-ene-3-beta,27-diolHMDB
Cholest-5-ene-3beta,26-diolHMDB
Cholest-5-ene-3 beta,27-diolHMDB
5-Cholestene-3 beta,27-diolHMDB
(25R)-Cholest-5-ene-3β,26-diolHMDB
(3Β,25R)-cholest-5-ene-3,26-diolHMDB
(3beta,25R)-Cholest-5-ene-3,26-diolHMDB
Cholest-5-ene-3β,26-diolHMDB
(3Β)-cholest-5-ene-3,26-diolHMDB
(3beta)-Cholest-5-ene-3,26-diolHMDB
26-HydroxycholesterolHMDB
(3 beta,25R)-Cholest-5-ene-3,26-diolHMDB
26-Hydroxycholesterol, (25R)HMDB
(25R)-Cholest-5-ene-3 beta,26-diolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,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-en-5-ol
Traditional Name(1S,2R,5S,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-en-5-ol
CAS Registry Number20380-11-4
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)CCC[C@@H](C)CO
InChI Identifier
InChI=1S/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyFYHRJWMENCALJY-YSQMORBQSA-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
  • 26-hydroxysteroid
  • Dihydroxy bile acid, alcohol, or derivatives
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • Delta-5-steroid
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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 Solubility0.00021 g/LALOGPS
logP6.21ALOGPS
logP5.75ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)17.42ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity122.47 m³·mol⁻¹ChemAxon
Polarizability51.56 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+195.49431661259
DarkChem[M-H]-195.66331661259
DeepCCS[M-2H]-235.12330932474
DeepCCS[M+Na]+209.51830932474
AllCCS[M+H]+206.132859911
AllCCS[M+H-H2O]+204.132859911
AllCCS[M+NH4]+208.032859911
AllCCS[M+Na]+208.532859911
AllCCS[M-H]-202.232859911
AllCCS[M+Na-2H]-204.232859911
AllCCS[M+HCOO]-206.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
27-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)CCC[C@@H](C)CO2586.1Standard polar33892256
27-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)CCC[C@@H](C)CO3366.6Standard non polar33892256
27-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)CCC[C@@H](C)CO3515.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
27-Hydroxycholesterol,1TMS,isomer #1C[C@@H](CO)CCC[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@@]21C3434.8Semi standard non polar33892256
27-Hydroxycholesterol,1TMS,isomer #2C[C@H](CCC[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)CO[Si](C)(C)C3438.4Semi standard non polar33892256
27-Hydroxycholesterol,2TMS,isomer #1C[C@H](CCC[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)CO[Si](C)(C)C3474.4Semi standard non polar33892256
27-Hydroxycholesterol,1TBDMS,isomer #1C[C@@H](CO)CCC[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@@]21C3652.3Semi standard non polar33892256
27-Hydroxycholesterol,1TBDMS,isomer #2C[C@H](CCC[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)CO[Si](C)(C)C(C)(C)C3697.6Semi standard non polar33892256
27-Hydroxycholesterol,2TBDMS,isomer #1C[C@H](CCC[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)CO[Si](C)(C)C(C)(C)C3962.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 27-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-0009000000-c409240ea9f4c08e2ba02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 27-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positivesplash10-001i-1211490000-d6f5e80defdccceda31c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 27-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 - 27-Hydroxycholesterol 10V, Positive-QTOFsplash10-0f79-0009200000-9ee1df2377674be6691c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 20V, Positive-QTOFsplash10-00kr-2109000000-2471d899cb75de6d36842016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 40V, Positive-QTOFsplash10-0r29-3139000000-969ef6deb6437f21d9ad2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0004900000-2045d37649040dcd2d052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 20V, Negative-QTOFsplash10-0ue9-0009500000-ac02d066655429b00b852016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 40V, Negative-QTOFsplash10-0a4r-3009000000-8b6280720e1ee0be80b42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 10V, Positive-QTOFsplash10-0f79-1209500000-a16dd407d41c22cc31442021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 20V, Positive-QTOFsplash10-0cdr-6479100000-db657345009052fe71e12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 40V, Positive-QTOFsplash10-0a4i-5910000000-84a62c4f6410b3c0eda92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0001900000-8975f0b18ceee10bde582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 20V, Negative-QTOFsplash10-0udi-0004900000-459f540b58ddc4074d2a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 27-Hydroxycholesterol 40V, Negative-QTOFsplash10-0002-0009000000-8268359a5f25a118a8c62021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
Tissue Locations
  • Brain
  • Fibroblasts
  • Neuron
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.538 +/- 0.04 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.013 +/- 0.001 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.3 +/- 0.074 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0013 +/- 0.0001 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.002 +/- 0.0004 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.0026 +/- 0.0002 uMAdult (>18 years old)Both
Multiple sclerosis
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0038 +/- 0.0003 uMElderly (>65 years old)BothAlzheimer's disease details
Cerebrospinal Fluid (CSF)Detected and Quantified0.01 +/- 0.001 uMAdult (>18 years old)BothAcute or chronic demyelinating polyneuropathies details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0058 +/- 0.0006 uMAdult (>18 years old)BothSubarachnoid hemorrhage details
Cerebrospinal Fluid (CSF)Detected and Quantified0.006 +/- 0.0006 uMAdult (>18 years old)Both
Meningitis
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0063 +/- 0.001 uMAdult (>18 years old)BothNeuroborreliosis details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0045 +/- 0.001 uMElderly (>65 years old)Both
Mild cognitive impairment
details
Cerebrospinal Fluid (CSF)Detected and Quantified0.003 +/- 0.0008 uMAdult (>18 years old)BothMultiple sclerosis details
Associated Disorders and Diseases
Disease References
Multiple sclerosis
  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. 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 ]
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, Shafaati M, Salomon A, Kivipelto M, Bjorkhem I, Wahlund LO: Are the CSF levels of 24S-hydroxycholesterol a sensitive biomarker for mild cognitive impairment? Neurosci Lett. 2006 Apr 10-17;397(1-2):83-7. Epub 2006 Jan 6. [PubMed:16406316 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022846
KNApSAcK IDNot Available
Chemspider ID110495
KEGG Compound IDC06340
BioCyc IDNot Available
BiGG ID48021
Wikipedia Link27-Hydroxycholesterol
METLIN ID6487
PubChem Compound123976
PDB IDNot Available
ChEBI ID76591
Food Biomarker OntologyNot Available
VMH IDXOL27OH
MarkerDB IDMDB00000377
Good Scents IDNot Available
References
Synthesis ReferenceHausheer, Frederick H.; Haridas, Kochat. Process for preparing 27-hydroxycholesterol and related derivatives. PCT Int. Appl. (1997), 38 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Summerfield JA, Billing BH, Shackleton CH: Identification of bile acids in the serum and urine in cholestasis. Evidence for 6alpha-hydroxylation of bile acids in man. Biochem J. 1976 Feb 15;154(2):507-16. [PubMed:938463 ]
  2. 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 ]
  3. Burkard I, Rentsch KM, von Eckardstein A: Determination of 24S- and 27-hydroxycholesterol in plasma by high-performance liquid chromatography-mass spectrometry. J Lipid Res. 2004 Apr;45(4):776-81. Epub 2004 Jan 16. [PubMed:14729854 ]
  4. Fu X, Menke JG, Chen Y, Zhou G, MacNaul KL, Wright SD, Sparrow CP, Lund EG: 27-hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J Biol Chem. 2001 Oct 19;276(42):38378-87. Epub 2001 Aug 14. [PubMed:11504730 ]
  5. Rajagopalon I, Kok E, Cohen BI, Javitt NB: 26-Hydroxycholesterol disulfate: metabolism and excretion in the normal neonate. J Steroid Biochem. 1986 Dec;25(6):991-4. [PubMed:3795956 ]
  6. Li S, Pang J, Jackson EM, Wilson WK, Mott GE, Schroepfer GJ Jr: Kinetics and plasma concentrations of 26-hydroxycholesterol in baboons. Biochim Biophys Acta. 2000 May 31;1485(2-3):173-84. [PubMed:10832098 ]
  7. Frolov A, Zielinski SE, Crowley JR, Dudley-Rucker N, Schaffer JE, Ory DS: NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols. J Biol Chem. 2003 Jul 11;278(28):25517-25. Epub 2003 Apr 28. [PubMed:12719428 ]
  8. Brown J 3rd, Theisler C, Silberman S, Magnuson D, Gottardi-Littell N, Lee JM, Yager D, Crowley J, Sambamurti K, Rahman MM, Reiss AB, Eckman CB, Wolozin B: Differential expression of cholesterol hydroxylases in Alzheimer's disease. J Biol Chem. 2004 Aug 13;279(33):34674-81. Epub 2004 May 17. [PubMed:15148325 ]
  9. Bellosta S, Corsini A, Bernini F, Granata A, Didoni G, Mazzotti M, Fumagalli R: 27-Hydroxycholesterol modulation of low density lipoprotein metabolism in cultured human hepatic and extrahepatic cells. FEBS Lett. 1993 Oct 11;332(1-2):115-8. [PubMed:8405424 ]
  10. Heverin M, Bogdanovic N, Lutjohann D, Bayer T, Pikuleva I, Bretillon L, Diczfalusy U, Winblad B, Bjorkhem I: Changes in the levels of cerebral and extracerebral sterols in the brain of patients with Alzheimer's disease. J Lipid Res. 2004 Jan;45(1):186-93. Epub 2003 Oct 1. [PubMed:14523054 ]
  11. Shoda J, Toll A, Axelson M, Pieper F, Wikvall K, Sjovall J: Formation of 7 alpha- and 7 beta-hydroxylated bile acid precursors from 27-hydroxycholesterol in human liver microsomes and mitochondria. Hepatology. 1993 Mar;17(3):395-403. [PubMed:8444412 ]
  12. Goldman M, Vlahcevic ZR, Schwartz CC, Gustafsson J, Swell L: Bile acid metabolism in cirrhosis. VIII. Quantitative evaluation of bile acid synthesis from [7 beta-3H]7 alpha-hydroxycholesterol and [G-3H]26-hydroxycholesterol. Hepatology. 1982 Jan-Feb;2(1):59-66. [PubMed:7054068 ]
  13. Lala DS, Syka PM, Lazarchik SB, Mangelsdorf DJ, Parker KL, Heyman RA: Activation of the orphan nuclear receptor steroidogenic factor 1 by oxysterols. Proc Natl Acad Sci U S A. 1997 May 13;94(10):4895-900. [PubMed:9144161 ]
  14. Norlin M, Andersson U, Bjorkhem I, Wikvall K: Oxysterol 7 alpha-hydroxylase activity by cholesterol 7 alpha-hydroxylase (CYP7A). J Biol Chem. 2000 Nov 3;275(44):34046-53. [PubMed:10882719 ]
  15. Babiker A, Dzeletovic S, Wiklund B, Pettersson N, Salonen J, Nyyssonen K, Eriksson M, Diczfalusy U, Bjorkhem I: Patients with atherosclerosis may have increased circulating levels of 27-hydroxycholesterol and cholestenoic acid. Scand J Clin Lab Invest. 2005;65(5):365-75. [PubMed:16081359 ]
  16. Luomala M, Paiva H, Laaksonen R, Thelen K, Lutjohann D, Peltonen N, Lehtimaki T: Plasma-soluble CD40 is related to cholesterol metabolism in patients with moderate hypercholesterolemia. Scand Cardiovasc J. 2006 Oct;40(5):280-4. [PubMed:17012138 ]
  17. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  18. 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 ]
  19. 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 ]
  20. 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 ]
  21. Corsini A, Verri D, Raiteri M, Quarato P, Paoletti R, Fumagalli R: Effects of 26-aminocholesterol, 27-hydroxycholesterol, and 25-hydroxycholesterol on proliferation and cholesterol homeostasis in arterial myocytes. Arterioscler Thromb Vasc Biol. 1995 Mar;15(3):420-8. [PubMed:7749852 ]
  22. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:
CYP7A1
Uniprot ID:
P22680
Molecular weight:
57660.155
Reactions
27-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28
Reactions
Cholesterol + Oxygen + NADPH + Hydrogen Ion → 27-Hydroxycholesterol + NADP + Waterdetails
27-Hydroxycholesterol + Oxygen + NADPH + Hydrogen Ion → 3beta-Hydroxy-5-cholestenoic acid + NADP + Waterdetails
General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
Reactions
27-Hydroxycholesterol + NADPH + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Waterdetails
27-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,27-Dihydroxycholesterol + NADP + Waterdetails