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Record Information
Version3.6
Creation Date2006-05-22 15:12:16 UTC
Update Date2016-02-11 01:05:50 UTC
HMDB IDHMDB02869
Secondary Accession Numbers
  • HMDB06850
Metabolite Identification
Common NameCampesterol
DescriptionCampesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia.
Structure
Thumb
Synonyms
ValueSource
(3beta)-Ergost-5-en-3-olChEBI
22,23-DihydrobrassicasterolChEBI
(3b)-Ergost-5-en-3-olGenerator
(3β)-ergost-5-en-3-olGenerator
(24R)-5-Ergosten-3-beta-olHMDB
(24R)-5-Ergosten-3b-olHMDB
(24R)-Ergost-5-en-3-beta-olHMDB
(24R)-Ergost-5-en-3b-olHMDB
(24R)-Methylcholest-5-en-3b-olHMDB
(24S)-beta-Methyl cholesterolHMDB
(3-beta)-Ergost-5-en-3-olHMDB
(3-beta-24R)-Ergost-5-en-3-olHMDB
(3b,24R)-Ergost-5-en-3-olHMDB
24-alpha-MethylcholesterolHMDB
24-Methyl-5-cholestene-3-olHMDB
24-Methylcholest-5-en-3beta-olHMDB
24a-Methyl-5-cholesten-3b-olHMDB
24a-MethylcholesterolHMDB
CampesterinHMDB
CampestrolHMDB
Ergost-5-en-3-beta-olHMDB
Ergost-5-en-3-olHMDB
Chemical FormulaC28H48O
Average Molecular Weight400.6801
Monoisotopic Molecular Weight400.370516158
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5S)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol
Traditional Name22,23-dihydrobrassicasterol
CAS Registry Number474-62-4
SMILES
[H][C@@]12CC[C@H]([C@H](C)CC[C@H](C)C(C)C)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier
InChI=1S/C28H48O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h9,18-20,22-26,29H,7-8,10-17H2,1-6H3/t19-,20+,22-,23-,24+,25-,26-,27-,28+/m0/s1
InChI KeyInChIKey=SGNBVLSWZMBQTH-ZRUUVFCLSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • 3-hydroxysteroid
  • 3-hydroxy-delta-5-steroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Food
  • Plant
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 (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point157.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.19e-05 mg/mLALOGPS
logP6.81ALOGPS
logP7.4ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)18.2ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.17 m3·mol-1ChemAxon
Polarizability52.45 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Muscle
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified17.23 (0.24-87.0) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
BloodDetected and Quantified6.46 +/- 0.051 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.35 +/- 0.014 uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00013 +/- 0.000049 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified601.94 +/- 6.49 uMAdult (>18 years old)BothPhytosterolemia details
Associated Disorders and Diseases
Disease References
Sitosterolemia
  1. Lutjohann D, Bjorkhem I, Beil UF, von Bergmann K: Sterol absorption and sterol balance in phytosterolemia evaluated by deuterium-labeled sterols: effect of sitostanol treatment. J Lipid Res. 1995 Aug;36(8):1763-73. [7595097 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012521
KNApSAcK IDC00003647
Chemspider ID4446730
KEGG Compound IDC01789
BioCyc IDCPD-3943
BiGG IDNot Available
Wikipedia LinkCampesterol
NuGOwiki LinkHMDB02869
Metagene LinkHMDB02869
METLIN ID167
PubChem Compound5283637
PDB IDNot Available
ChEBI ID19809
References
Synthesis ReferenceZhou, Yu-jie; Dai, Ling-mei; Chen, Fu-ming; Li, Zong-cheng. Separation of b-sitosterol and campesterol by high-speed countercurrent chromatography. Jingxi Huagong (2002), 19(3), 183-185.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Miettinen TE, Kesaniemi YA, Gylling H, Jarvinen H, Silvennoinen E, Miettinen TA: Noncholesterol sterols in bile and stones of patients with cholesterol and pigment stones. Hepatology. 1996 Feb;23(2):274-80. [8591852 ]
  2. Phillips KM, Ruggio DM, Bailey JA: Precise quantitative determination of phytosterols, stanols, and cholesterol metabolites in human serum by capillary gas-liquid chromatography. J Chromatogr B Biomed Sci Appl. 1999 Sep 10;732(1):17-29. [10517218 ]
  3. Siirtola A, Ketomaki A, Miettinen TA, Gylling H, Lehtimaki T, Holmberg C, Salo MK, Antikainen M: Cholesterol absorption and synthesis in pediatric kidney, liver, and heart transplant recipients. Transplantation. 2006 Feb 15;81(3):327-34. [16477216 ]
  4. Paiva H, Thelen KM, Van Coster R, Smet J, De Paepe B, Mattila KM, Laakso J, Lehtimaki T, von Bergmann K, Lutjohann D, Laaksonen R: High-dose statins and skeletal muscle metabolism in humans: a randomized, controlled trial. Clin Pharmacol Ther. 2005 Jul;78(1):60-8. [16003294 ]
  5. Dayal B, Tint GS, Batta AK, Speck J, Khachadurian AK, Shefer S, Salen G: Identification of 5 alpha-stanols in patients with sitosterolemia and xanthomatosis: stereochemistry of the protonolysis of steroidal organoboranes. Steroids. 1982 Aug;40(2):233-43. [6297129 ]
  6. Kuriyama M, Fujiyama J, Kasama T, Osame M: High levels of plant sterols and cholesterol precursors in cerebrotendinous xanthomatosis. J Lipid Res. 1991 Feb;32(2):223-9. [2066659 ]
  7. Locker PK, Jungbluth GL, Francom SF, Hughes GS Jr: Lifibrol: a novel lipid-lowering drug for the therapy of hypercholesterolemia. Lifibrol Study Group. Clin Pharmacol Ther. 1995 Jan;57(1):73-88. [7828385 ]

Enzymes

General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
24-Methylenecholesterol + NADPH + Hydrogen Ion → Campesterol + NADPdetails
General function:
Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity
Specific function:
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system plays a crucial role in the biosynthesis of all classes of hormonal steroids.
Gene Name:
HSD3B2
Uniprot ID:
P26439
Molecular weight:
42051.845