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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-05-11 14:21:33 UTC
Update Date2021-09-14 15:19:06 UTC
HMDB IDHMDB0006119
Secondary Accession Numbers
  • HMDB06119
Metabolite Identification
Common Name7beta-Hydroxycholesterol
Description7beta-Hydroxycholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7beta-hydroxycholesterol is considered to be a sterol lipid molecule. 7beta-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 7beta-Hydroxycholesterol has been identified in atheromatous plaques and in plasma of atherosclerotic patients (PMID: 16604541 ). 7beta-Hydroxycholesterol induces apoptosis in Caco-2 cells and alters lysosomal membrane integrity. It exhibits a specific enhancement of oxidative stress and of endonuclease G expression (PMID: 17136497 ).
Structure
Data?1582752374
Synonyms
ValueSource
(3beta,7beta)-Cholest-5-ene-3,7-diolChEBI
7-HYDROXYCHOLESTEROLChEBI
(3b,7b)-Cholest-5-ene-3,7-diolGenerator
(3Β,7β)-cholest-5-ene-3,7-diolGenerator
7b-HydroxycholesterolGenerator
7Β-hydroxycholesterolGenerator
7 beta-HydroxycholesterolMeSH
Cholest-5-en-3beta,7beta-diolMeSH
5-Cholestene-3beta,7beta-diolHMDB
7beta-HydroxycholesterolHMDB
Cholest-5-ene-3beta,7beta-diolHMDB
7beta-Hydroxycholest-5-en-3beta-olHMDB
7β-Hydroxycholest-5-en-3β-olHMDB
Cholest-5-ene-3β,7β-diolHMDB
delta5-Cholestene-3beta,7beta-diolHMDB
Δ5-Cholestene-3β,7β-diolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(1S,2R,5S,9R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol
Traditional Name(1S,2R,5S,9R,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-ene-5,9-diol
CAS Registry Number566-27-8
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI Identifier
InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h16-18,20-25,28-29H,6-15H2,1-5H3/t18-,20+,21-,22+,23+,24+,25+,26+,27-/m1/s1
InChI KeyOYXZMSRRJOYLLO-KGZHIOMZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • 3-beta-hydroxysteroid
  • 7-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

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 Solubility0.00048 g/LALOGPS
logP10(5.61) g/LALOGPS
logP10(5.96) g/LChemAxon
logS10(-5.9) g/LALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.06 m³·mol⁻¹ChemAxon
Polarizability51.12 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]+200.38231661259
DarkChem[M-H]-196.97231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7beta-Hydroxycholesterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C2676.9Standard polar33892256
7beta-Hydroxycholesterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C3303.5Standard non polar33892256
7beta-Hydroxycholesterol[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C3367.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7beta-Hydroxycholesterol,1TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O)CC1=C[C@@H]3O[Si](C)(C)C3261.5Semi standard non polar33892256
7beta-Hydroxycholesterol,1TMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)CC1=C[C@@H]3O3256.5Semi standard non polar33892256
7beta-Hydroxycholesterol,2TMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C)CC1=C[C@@H]3O[Si](C)(C)C3162.3Semi standard non polar33892256
7beta-Hydroxycholesterol,1TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O)CC1=C[C@@H]3O[Si](C)(C)C(C)(C)C3509.7Semi standard non polar33892256
7beta-Hydroxycholesterol,1TBDMS,isomer #2CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)CC1=C[C@@H]3O3482.4Semi standard non polar33892256
7beta-Hydroxycholesterol,2TBDMS,isomer #1CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@H]3[C@H](CC[C@@]21C)[C@@]1(C)CC[C@H](O[Si](C)(C)C(C)(C)C)CC1=C[C@@H]3O[Si](C)(C)C(C)(C)C3655.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7beta-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-1229000000-8b7536c0aaf1a204c4852017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7beta-Hydroxycholesterol GC-MS (2 TMS) - 70eV, Positivesplash10-001i-6110590000-3008d2fd9fd93235cd842017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7beta-Hydroxycholesterol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7beta-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 - 7beta-Hydroxycholesterol 10V, Positive-QTOFsplash10-0f79-0009200000-dd83a63fa5280b1a0a322017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 20V, Positive-QTOFsplash10-05n0-2129100000-d4fcf32706fb430f9b9f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 40V, Positive-QTOFsplash10-0a4i-7369000000-3cb2e62a7e2f2c82bd312017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0003900000-631080b9e26008e235d22017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 20V, Negative-QTOFsplash10-0ue9-0009800000-c89cf39b6f8d49fe8f542017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 40V, Negative-QTOFsplash10-00kr-1009000000-2c0cdf0af0d6dd2fad2f2017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 10V, Negative-QTOFsplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 20V, Negative-QTOFsplash10-0udi-0000900000-079f76b4d985e4b92c9d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 40V, Negative-QTOFsplash10-0002-0009100000-71906a2df9357f22bb562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 10V, Positive-QTOFsplash10-0udi-1003900000-28bc1d0c38885b76f1022021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 20V, Positive-QTOFsplash10-0l6r-9134200000-b6e1e10244022e0b9cce2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7beta-Hydroxycholesterol 40V, Positive-QTOFsplash10-0a4i-9740000000-f4f3165be03261bd2bd92021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.011 +/- 0.0027 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.003 +/- 0.0006 uMAdult (>18 years old)Not SpecifiedNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.004 +/- 0.0017 uMAdult (>18 years old)BothMultiple Sclerosis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
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 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDDB04706
Phenol Explorer Compound IDNot Available
FooDB IDFDB023832
KNApSAcK IDNot Available
Chemspider ID415508
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound473141
PDB IDHCR
ChEBI ID42989
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. Prunet C, Montange T, Vejux A, Laubriet A, Rohmer JF, Riedinger JM, Athias A, Lemaire-Ewing S, Neel D, Petit JM, Steinmetz E, Brenot R, Gambert P, Lizard G: Multiplexed flow cytometric analyses of pro- and anti-inflammatory cytokines in the culture media of oxysterol-treated human monocytic cells and in the sera of atherosclerotic patients. Cytometry A. 2006 May;69(5):359-73. [PubMed:16604541 ]
  2. Roussi S, Gosse F, Aoude-Werner D, Zhang X, Marchioni E, Geoffroy P, Miesch M, Raul F: Mitochondrial perturbation, oxidative stress and lysosomal destabilization are involved in 7beta-hydroxysitosterol and 7beta-hydroxycholesterol triggered apoptosis in human colon cancer cells. Apoptosis. 2007 Jan;12(1):87-96. [PubMed:17136497 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]