Record Information
Creation date2011-09-21 00:20:29 UTC
Update date2015-07-21 06:57:24 UTC
Primary IDFDB022846
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name27-Hydroxycholesterol
Description27-hydroxycholesterol is an oxygenated derivative of cholesterol and a major oxysterol in circulation. 27-hydroxycholesterol is the product of the enzyme sterol 27-hydroxylase. The enzyme is critical for 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 7a-hydroxylase in the liver, and changes in the activity of this enzyme may lead to accumulation of 27-hydroxycholesterol in the circulation. It has been reported that patients with a genetic deficiency of oxysterol 7a-hydroxylase in the liver had markedly increased levels of 27-hydroxycholesterol in the circulation. Under normal conditions, however, 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. Three possible explanations for the high concentrations of 27-hydroxycholesterol found in the circulation of the three subjects with atherosclerosis could be: 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. 3) The high amounts of cholesterol accumulating in macrophages in some patients with atherosclerosis may result in 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 ateromas 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) [HMDB]
CAS Number20380-11-4
Predicted Properties
Water Solubility0.00021 g/LALOGPS
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
Polarizability51.38 ųChemAxon
Number of Rings4ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC27H46O2
IUPAC name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[^{2,7}.0^{11,15}]heptadec-7-en-5-ol
InChI IdentifierInChI=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
Isomeric SMILES[H][C@](C)(CO)CCC[C@@]([H])(C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@@]([H])(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
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
  • 26-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
  • Fatty alcohol
  • Fatty acyl
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
SpectraNot Available
ChemSpider ID110495
KEGG Compound IDC06340
Pubchem Compound ID123976
Pubchem Substance IDNot Available
ChEBI ID16546
Phenol-Explorer IDNot Available
DrugBank IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID48021
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Bile Acid BiosynthesisSMP00035 map00120
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
MSDSNot Available
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference