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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-05-22 15:12:16 UTC
Update Date2020-05-01 17:28:02 UTC
HMDB IDHMDB0002869
Secondary Accession Numbers
  • HMDB0006850
  • HMDB02869
  • 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
Data?1588354082
Synonyms
ValueSource
(24R)Ergost-5-en-3beta-olChEBI
(24R)Ergost-5-en-3b-olGenerator
(24R)Ergost-5-en-3β-olGenerator
22,23-DihydrobrassicasterolMeSH, HMDB
Campesterol, (3beta)-isomerMeSH, HMDB
Ergost-5-en-3 beta- ol, 24 epimerMeSH, HMDB
24 alpha-Methylcholest-5-en-3 beta-olMeSH, HMDB
24-MethylcholesterolMeSH, HMDB
Campesterol, (3beta,24xi)-isomerMeSH, HMDB
(24R)-24-Methylcholest-5-en-3beta-olHMDB
(24R)-24-Methylcholest-5-en-3β-olHMDB
(24R)-5-Ergosten-3beta-olHMDB
(24R)-5-Ergosten-3β-olHMDB
(24R)-Methylcholest-5-en-3beta-olHMDB
(24R)-Methylcholest-5-en-3β-olHMDB
(3beta,24R)-Ergost-5-en-3-olHMDB
(3β,24R)-Ergost-5-en-3-olHMDB
24(R)-MethylcholesterolHMDB
24alpha-Methyl-5-cholesten-3beta-olHMDB
24alpha-MethylcholesterolHMDB
24α-Methyl-5-cholesten-3β-olHMDB
24α-MethylcholesterolHMDB
CampasterolHMDB
CampesterinHMDB
CampesterolHMDB
delta5-24-Isoergosten-3beta-olHMDB
Δ5-24-Isoergosten-3β-olHMDB
Chemical FormulaC28H48O
Average Molecular Weight400.691
Monoisotopic Molecular Weight400.370516166
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-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,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number474-62-4
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)CC[C@@H](C)C(C)C
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-/m1/s1
InChI KeySGNBVLSWZMBQTH-PODYLUTMSA-N
Chemical Taxonomy
Description 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
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

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 Solubility2.2e-05 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity125.17 m³·mol⁻¹ChemAxon
Polarizability52.31 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-05e9-4911000000-875cf823819e0cce5862Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-2009000000-2550db029fd542f67e17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-3003900000-507d30a41b66acb01111Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-1019500000-847aedbaa12e54dfba2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001a-7039100000-37d6bffa6947a8543503Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-9086000000-ab8fc0d2e66c929b57d5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-262b69e7e0c3c62469f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-c1bc60a76f16fac8a564Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-2019000000-048057355ee14dde6999Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Kidney
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified7.462 +/- 7.487 uMAdult (>18 years old)Female
Normal
details
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
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.00013 +/- 0.000049 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified601.94 +/- 6.49 uMAdult (>18 years old)BothPhytosterolemia details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer 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. [PubMed:7595097 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012521
KNApSAcK IDC00003647
Chemspider ID151215
KEGG Compound IDC01789
BioCyc IDCPD-707
BiGG IDNot Available
Wikipedia LinkCampesterol
METLIN IDNot Available
PubChem Compound173183
PDB IDNot Available
ChEBI ID28623
Food Biomarker OntologyNot Available
VMH IDNot Available
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. 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. [PubMed:16003294 ]
  2. 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. [PubMed:6297129 ]
  3. 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. [PubMed:2066659 ]
  4. 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. [PubMed:16477216 ]
  5. 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. [PubMed:8591852 ]
  6. 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. [PubMed:7828385 ]
  7. 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. [PubMed:10517218 ]

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