Showing Compound 27-Hydroxycholesterol (FDB022846)

Record Information

Version

1.0

Creation date

2011-09-21 00:20:29 UTC

Update date

2015-07-21 06:57:24 UTC

Primary ID

FDB022846

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

27-Hydroxycholesterol

Description

27-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 Number

20380-11-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(25R)-26-Hydroxycholesterol	hmdb
(25R)-Cholest-5-ene-3b,26-diol	hmdb
(25R)-Cholest-5-ene-3beta,26-diol	hmdb
(25R)-Cholest-5-ene-3β,26-diol	Generator
(3-beta)-cholest-5-ene-3,26-diol	hmdb
(3b,25R)-Cholest-5-ene-3,26-diol	hmdb
(3beta,25R)-Cholest-5-ene-3,26,diol	hmdb
26-hydroxycholesterol(25R)	hmdb
5-Cholestene-3b,27-diol	Generator
5-Cholestene-3beta,27-diol	ChEBI

Showing 1 to 10 of 19 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00021 g/L	ALOGPS
logP	6.21	ALOGPS
logP	5.75	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	17.42	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	122.47 m³·mol⁻¹	ChemAxon
Polarizability	51.38 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C27H46O2

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

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 Key

FYHRJWMENCALJY-JRBXREGASA-N

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 Weight

402.6529

Monoisotopic Molecular Weight

402.349780716

Classification

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Bile acids, alcohols and derivatives

Direct Parent

Dihydroxy bile acids, alcohols and derivatives

Alternative Parents

Substituents

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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16546

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB02103

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

48021

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound 27-Hydroxycholesterol (FDB022846)

Structure for FDB022846 (27-Hydroxycholesterol)