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Record Information
Version3.6
Creation Date2007-05-22 19:16:51 UTC
Update Date2016-02-11 01:07:26 UTC
HMDB IDHMDB06247
Secondary Accession NumbersNone
Metabolite Identification
Common Name25-Hydroxycholesterol
Description25-Hydroxycholesterol is steroid derivative that suppresses the cleavage of sterol regulatory element binding proteins (SREBPs). It also induces apoptosis through down-regulation of Bcl-2 expression and activation of caspases. 25-Hydroxycholesterol also enhances Interleukin-1 beta (IL-1beta-induced) IL-8 production.(PMID: 17086498 ). 25-hydroxycholesterol is endogenously produced from cholesterol at early time intervals after cholesterol ingestion. It inhibits HMG-CoA reductase and so it also plays a significant role in the in vivo regulation of cholesterol biosynthesis after an acute dietary cholesterol challenge.
Structure
Thumb
Synonyms
ValueSource
(beta)-Cholest-5-ene-3-25-diolHMDB
25-Hydroxy-cholesterolHMDB
25-Hydroxycholest-5-en-3-olHMDB
5-Cholestene-3beta-25-diolHMDB
Cholest-5-en-3beta-25-diolHMDB
Cholest-5-ene-3-b,25-diolHMDB
Cholest-5-ene-3-beta,25-diolHMDB
Cholest-5-ene-3beta-25-diolHMDB
Chemical FormulaC27H46O2
Average Molecular Weight402.6529
Monoisotopic Molecular Weight402.349780716
IUPAC Name(2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name(2R,5S,10S,14R,15R)-14-[(2R)-6-hydroxy-6-methylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
CAS Registry Number2140-46-7
SMILES
[H]C12CC[C@H]([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23?,24?,26+,27-/m1/s1
InChI KeyInChIKey=INBGSXNNRGWLJU-POAVOMIWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cholesterols and derivatives. These 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-skeleton
  • Cholesterol
  • 25-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Hormones, Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point172 - 173 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.000244 mg/mLALOGPS
logP5.95ALOGPS
logP5.64ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity122.45 m3·mol-1ChemAxon
Polarizability50.21 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
27-Hydroxylase DeficiencySMP00720Not Available
Bile Acid BiosynthesisSMP00035map00120
Cerebrotendinous Xanthomatosis (CTX)SMP00315Not Available
Congenital Bile Acid Synthesis Defect Type IISMP00314Not Available
Congenital Bile Acid Synthesis Defect Type IIISMP00318Not Available
Familial Hypercholanemia (FHCA)SMP00317Not Available
Zellweger SyndromeSMP00316Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.02 +/- 0.003 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.001 +/- 0.0001 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023859
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15519
BioCyc IDCPD-7241
BiGG ID2197441
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06247
Metagene LinkHMDB06247
METLIN ID3899
PubChem Compound53477807
PDB IDNot Available
ChEBI ID37616
References
Synthesis ReferenceRyer, August I.; Gebert, Wm. H. Steroids. (1954), US 2673206 19540323 CAN 49:8565 AN 1955:8565
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Bai B, Yamamoto K, Sato H, Sugiura H, Tanaka T: Combined effect of 25-hydroxycholesterol and IL-1beta on IL-8 production in human colon carcinoma cell line (Caco-2). Inflammation. 2005 Dec;29(4-6):141-6. [17086498 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Not Available
Gene Name:
CYP7B1
Uniprot ID:
O75881
Molecular weight:
58255.325
Reactions
25-Hydroxycholesterol + NADPH + Oxygen → 7-a,25-Dihydroxycholesterol + NADP + Waterdetails
25-Hydroxycholesterol + NADPH + Hydrogen Ion + Oxygen → 7-a,25-Dihydroxycholesterol + NADP + Waterdetails
General function:
Involved in steroid metabolic process
Specific function:
Binds cholesterol and a range of oxysterols. Cholesterol binding promotes the formation of a complex with PP2A and a tyrosine phosphatase which dephosphorylate ERK1/2, whereas 25- hydroxycholesterol causes its disassembly. Regulates cholesterol efflux by decreasing ABCA1 stability
Gene Name:
OSBP
Uniprot ID:
P22059
Molecular weight:
89419.9
General function:
Involved in iron ion binding
Specific function:
Catalyzes the formation of 25-hydroxycholesterol from cholesterol, leading to repress cholesterol biosynthetic enzymes. May play an important role in regulating lipid metabolism by synthesizing a corepressor that blocks sterol regulatory element binding protein (SREBP) processing. In testis, production of 25-hydroxycholesterol by macrophages may play a role in Leydig cell differentiation.
Gene Name:
CH25H
Uniprot ID:
O95992
Molecular weight:
31744.755
Reactions
Cholesterol + AH(2) + Oxygen → 25-Hydroxycholesterol + A + Waterdetails
Cholesterol + Reduced acceptor + Oxygen → 25-Hydroxycholesterol + Acceptor + Waterdetails