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Showing metabocard for Cholesterol (BMDB0000067)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:19:13 UTC
Update Date2020-06-04 22:59:16 UTC
MCDB ID BMDB0000067
Secondary Accession Numbers
  • BMDB00067
Metabolite Identification
Common NameCholesterol
DescriptionCholesterol belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Cholesterol is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Cholesterol is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(3beta,14beta,17alpha)-Cholest-5-en-3-olChEBI
Cholest-5-en-3beta-olChEBI
CholesterinChEBI
(3b,14b,17a)-Cholest-5-en-3-olGenerator
(3Β,14β,17α)-cholest-5-en-3-olGenerator
Cholest-5-en-3b-olGenerator
Cholest-5-en-3β-olGenerator
(3Β)-cholest-5-en-3-olHMDB
(3beta)-Cholest-5-en-3-olHMDB
3Β-hydroxycholest-5-eneHMDB
3beta-Hydroxycholest-5-eneHMDB
5:6-Cholesten-3β-olHMDB
5:6-Cholesten-3beta-olHMDB
(-)-CholesterolHMDB
CholesterineHMDB
Cholesterol base HHMDB
Cholesteryl alcoholHMDB
CholestrinHMDB
CholestrolHMDB
CordulanHMDB
DastarHMDB
DusolineHMDB
DusoranHMDB
DytholHMDB
Fancol CHHMDB
HydrocerinHMDB
KathroHMDB
LanolHMDB
Super hartolanHMDB
TegolanHMDB
CholesterolHMDB
Chemical FormulaC27H46O
Average Molecular Weight386.6535
Monoisotopic Molecular Weight386.354866094
IUPAC Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
Traditional Name(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol
CAS Registry Number57-88-5
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)CCCC(C)C
InChI Identifier
InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
InChI KeyHVYWMOMLDIMFJA-DPAQBDIFSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives 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
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP7.02ALOGPS
logP7.11ChemAxon
logS-7.1ALOGPS
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
Refractivity120.62 m³·mol⁻¹ChemAxon
Polarizability50.64 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected and Quantified101 uM details
Detected and Quantified362 uM details
Detected but not QuantifiedNot Applicable details
Detected and Quantified52 uM details
Detected and Quantified52 uM details
Detected and Quantified129 uM details
Detected and Quantified52 uM details
Detected and Quantified362 uM details
Detected and Quantified103 uM details
Detected and Quantified103 uM details
Detected and Quantified129 uM details
Detected and Quantified52 uM details
Detected and Quantified52 uM details
Detected and Quantified52 uM details
Detected and Quantified52 uM details
Detected and Quantified155 uM details
Detected and Quantified155 uM details
Detected and Quantified362 uM details
Detected and Quantified206 uM details
Detected and Quantified206 uM details
Detected and Quantified206 uM details
Detected and Quantified206 uM details
Detected and Quantified206 uM details
Detected and Quantified78 uM details
Detected and Quantified90 uM details
Detected and Quantified78 uM details
Detected and Quantified258 uM details
Detected and Quantified258 uM details
Detected and Quantified362 uM details
Detected and Quantified362 uM details
Detected and Quantified362 uM details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
HMDB IDHMDB0000067
DrugBank IDDB04540
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013269
KNApSAcK IDC00003648
Chemspider IDNot Available
KEGG Compound IDC00187
BioCyc IDCHOLESTEROL
BiGG IDNot Available
Wikipedia LinkCholesterol
METLIN IDNot Available
PubChem Compound5997
PDB IDNot Available
ChEBI ID16113
References
Synthesis ReferenceZhu, Yongming; Qin, Liena; Liu, Rui. Simple method for synthesis cholesterol from Diosgenin. Faming Zhuanli Shenqing Gongkai Shuomingshu (2006), 9 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shi Y, Zhang JH, Shi D, Jiang M, Zhu YX, Mei SR, Zhou YK, Dai K, Lu B: Selective solid-phase extraction of cholesterol using molecularly imprinted polymers and its application in different biological samples. J Pharm Biomed Anal. 2006 Nov 16;42(5):549-55. doi: 10.1016/j.jpba.2006.05.022. Epub 2006 Jul 21. [PubMed:16859856 ]
  2. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  3. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  5. USDA Food Composition Databases [Link]
  6. Fooddata+, The Technical University of Denmark (DTU) [Link]