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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:03 UTC
HMDB IDHMDB0000534
Secondary Accession Numbers
  • HMDB00534
Metabolite Identification
Common NameCampestanol
DescriptionCampestanol, also known as chalinastanol, 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. Campestanol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752137
Synonyms
ValueSource
(24R)-5a-Ergostan-3b-olHMDB
24b-EthylcholestanolHMDB
24b-MethylcholestanolHMDB
5a-DihydrocampesterolHMDB
ChalinastanolHMDB
Dihydro-neospongosterolHMDB
DihydrocampesterinHMDB
Chemical FormulaC28H50O
Average Molecular Weight402.696
Monoisotopic Molecular Weight402.386166222
IUPAC Name(1S,2S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
Traditional Name(1S,2S,10R,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-ol
CAS Registry Number474-60-2
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])CCC2CC(O)CC[C@]12C
InChI Identifier
InChI=1S/C28H50O/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/h18-26,29H,7-17H2,1-6H3/t19-,20-,21?,22?,23+,24-,25+,26+,27+,28-/m1/s1
InChI KeyARYTXMNEANMLMU-XKPVSPJHSA-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.3e-05 g/LALOGPS
logP6.86ALOGPS
logP7.81ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)18.3ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity124.32 m³·mol⁻¹ChemAxon
Polarizability52.93 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.35131661259
DarkChem[M-H]-197.58531661259
AllCCS[M+H]+207.44832859911
AllCCS[M-H]-204.22532859911
DeepCCS[M-2H]-252.21330932474
DeepCCS[M+Na]+227.60630932474
AllCCS[M+H]+207.432859911
AllCCS[M+H-H2O]+205.532859911
AllCCS[M+NH4]+209.332859911
AllCCS[M+Na]+209.832859911
AllCCS[M-H]-204.232859911
AllCCS[M+Na-2H]-206.332859911
AllCCS[M+HCOO]-208.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Campestanol[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])CCC2CC(O)CC[C@]12C2177.9Standard polar33892256
Campestanol[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])CCC2CC(O)CC[C@]12C3218.7Standard non polar33892256
Campestanol[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])CCC2CC(O)CC[C@]12C3313.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Campestanol,1TMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3255.4Semi standard non polar33892256
Campestanol,1TBDMS,isomer #1CC(C)[C@H](C)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CCC4CC(O[Si](C)(C)C(C)(C)C)CC[C@]4(C)[C@H]3CC[C@@]21C3489.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Campestanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-007c-1109000000-8ef40d9b3bd55f00db252017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campestanol GC-MS (1 TMS) - 70eV, Positivesplash10-0a4m-3103900000-9678b7561737676bad6e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campestanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Campestanol GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 10V, Positive-QTOFsplash10-0f79-1019500000-03cdd9e8dc25a947273d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 20V, Positive-QTOFsplash10-000j-4049100000-ec9628a0bb11615fce522017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 40V, Positive-QTOFsplash10-000i-8097000000-87748227ade42491b7202017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 10V, Negative-QTOFsplash10-0udi-0001900000-cd6aad7ef1ded3e1c0502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 20V, Negative-QTOFsplash10-0udi-0004900000-65f83046cac75532eea12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 40V, Negative-QTOFsplash10-00kr-2009000000-1d136880e7b1c591672c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 10V, Positive-QTOFsplash10-0udi-1013900000-1e30ba588e54886623462021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 20V, Positive-QTOFsplash10-052s-9850100000-0d27950a08da4a7b75d72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 40V, Positive-QTOFsplash10-000m-9540000000-0b755f71588d78783ef62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 10V, Negative-QTOFsplash10-0udi-0000900000-f6441655e590f9a4f0c22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 20V, Negative-QTOFsplash10-0udi-0000900000-f6441655e590f9a4f0c22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Campestanol 40V, Negative-QTOFsplash10-0udj-0009600000-1e70046fe536fce831bc2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.5 +/- 2.5 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified4.967 +/- 2.483 uMAdult (>18 years old)Not SpecifiedNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified96.9 +/- 4.9 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. [PubMed:7595097 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001925
KNApSAcK IDC00007516
Chemspider ID17215967
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCampestanol
METLIN ID5519
PubChem Compound22833530
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceKircher, Henry W.; Rosenstein, Fumiko U. Purification of campesterol and preparation of 7-dehydrocampesterol, 7-campestenol, and campestanol. Lipids (1974), 9(5), 333-7.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shoemaker JD, Elliott WH: Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease. J Chromatogr. 1991 Jan 2;562(1-2):125-38. [PubMed:2026685 ]
  2. Hoffmann GF, Seppel CK, Holmes B, Mitchell L, Christen HJ, Hanefeld F, Rating D, Nyhan WL: Quantitative organic acid analysis in cerebrospinal fluid and plasma: reference values in a pediatric population. J Chromatogr. 1993 Jul 23;617(1):1-10. [PubMed:8376520 ]
  3. 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 ]
  4. Heinemann T, Axtmann G, von Bergmann K: Comparison of intestinal absorption of cholesterol with different plant sterols in man. Eur J Clin Invest. 1993 Dec;23(12):827-31. [PubMed:8143759 ]
  5. Plat J, Mensink RP: Effects of plant sterols and stanols on lipid metabolism and cardiovascular risk. Nutr Metab Cardiovasc Dis. 2001 Feb;11(1):31-40. [PubMed:11383323 ]