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Record Information
Version2.0
Created at2022-05-11 16:33:22 UTC
Updated at2022-05-11 16:33:22 UTC
NP-MRD IDNP0086872
Secondary Accession NumbersNone
Natural Product Identification
Common Name27-Hydroxycholesterol
Description27-Hydroxycholesterol, also known as cholest-5-ene-3b,27-diol, 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. Thus, 27-hydroxycholesterol is considered to be a sterol lipid molecule. 27-Hydroxycholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Within humans, 27-hydroxycholesterol participates in a number of enzymatic reactions. In particular, 27-hydroxycholesterol can be biosynthesized from cholesterol through the action of the enzyme 25-hydroxycholesterol 7-alpha-hydroxylase. In addition, 27-hydroxycholesterol can be converted into 7-a,27-dihydroxycholesterol through the action of the enzyme cholesterol 7-alpha-monooxygenase. In humans, 27-hydroxycholesterol is involved in the metabolic disorder called familial hypercholanemia (fhca). 27-Hydroxycholesterol is a potentially toxic compound. 27-Hydroxycholesterol was first documented in 1986 (PMID: 3795956). A 27-Hydroxycholesterol in which the 25-position has R-configuration (PMID: 14729854) (PMID: 11504730) (PMID: 10832098) (PMID: 12719428).
Structure
Thumb
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 Mass402.6529 Da
Monoisotopic Mass402.34978 Da
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 NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
HMDB IDHMDB0002103
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
General References
  1. 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. doi: 10.1194/jlr.D300036-JLR200. Epub 2004 Jan 16. [PubMed:14729854 ]
  2. 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. doi: 10.1074/jbc.M105805200. Epub 2001 Aug 14. [PubMed:11504730 ]
  3. 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. doi: 10.1016/0022-4731(86)90334-1. [PubMed:3795956 ]
  4. 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. doi: 10.1016/s1388-1981(00)00058-5. [PubMed:10832098 ]
  5. 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. doi: 10.1074/jbc.M302588200. Epub 2003 Apr 28. [PubMed:12719428 ]