Record Information
Version1.0
Created at2020-04-17 18:37:27 UTC
Updated at2020-12-07 19:10:57 UTC
CannabisDB IDCDB004794
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameCholesterol
DescriptionCholesterol, also known as cholesterin or cordulan, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, cholesterol is considered to be a sterol lipid molecule. Cholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cholesterol is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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
delta5-Cholesten-3beta-olPhytoBank
Δ5-Cholesten-3β-olPhytoBank
Chemical FormulaC27H46O
Average Molecular Weight386.65
Monoisotopic Molecular Weight386.3549
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 Number80356-14-5
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point148 °CNot Available
Boiling Point360 °CWikipedia
Water Solubility9.5e-05 mg/mLNot 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
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0a4l-7922000000-36e8a5e1a77d2e71d1d1Spectrum
GC-MSCholesterol, 1 TMS, GC-MS Spectrumsplash10-004i-3911000000-52f5261007adc218f8f8Spectrum
GC-MSCholesterol, non-derivatized, GC-MS Spectrumsplash10-052b-2932000000-1667c83d002043a59fffSpectrum
GC-MSCholesterol, non-derivatized, GC-MS Spectrumsplash10-000l-9527000000-5529a262047f5369c9c1Spectrum
GC-MSCholesterol, non-derivatized, GC-MS Spectrumsplash10-0mkr-2954000000-60e7d1f5973e4de33decSpectrum
GC-MSCholesterol, non-derivatized, GC-MS Spectrumsplash10-014i-1009000000-e82b8e23dedb45ce70e6Spectrum
GC-MSCholesterol, non-derivatized, GC-MS Spectrumsplash10-056v-2900000000-04687c9f19ff52ba4654Spectrum
Predicted GC-MSCholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i3-1109000000-8cd386b595bd5151c5a2Spectrum
Predicted GC-MSCholesterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-3104900000-698223f49da0b0c1cf81Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - n/a 27V, positivesplash10-052u-0690000000-36b4aea6637bdf069b5dSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-014i-3639000000-18a9275beb9bae48c1d7Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-014j-4934000000-f755ada933cfcf53c303Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-0002-5921000000-e7d43c825b9f6d45e679Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 20V, positivesplash10-0532-5910000000-ce90c49b7429a03a65daSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 30V, positivesplash10-05nb-8900000000-2e8913fec7126b5b2a62Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 40V, positivesplash10-0apl-9600000000-3096c7a78c3dd2e6a538Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 50V, positivesplash10-067l-9400000000-1b57543b4cd0a05b9b3fSpectrum
MS/MSLC-MS/MS Spectrum - QTOF 60V, positivesplash10-0aru-9300000000-45a29b76dfefce3f01caSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0009000000-dccd68f70545aeac4fabSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05p9-3149000000-7f25daf2b709c7e0d177Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c00-6269000000-5333d0216e01a3e43367Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-dc853b29b9e884bbb03bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-09d9608700564a6fef78Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ldi-1009000000-96f6e67651380e1c959eSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Phosphatidylcholine-sterol acyltransferaseLCAT16q22.1P04180 details
Lysosomal acid lipase/cholesteryl ester hydrolaseLIPA10q23.2-q23.3P38571 details
Bile salt-activated lipaseCEL9q34.3P19835 details
Sulfotransferase family cytosolic 2B member 1SULT2B119q13.3O00204 details
Steryl-sulfataseSTSXp22.32P08842 details
Sterol O-acyltransferase 2SOAT212q13.13O75908 details
Cholesterol 7-alpha-monooxygenaseCYP7A18q11-q12P22680 details
Sterol O-acyltransferase 1SOAT11q25P35610 details
7-dehydrocholesterol reductaseDHCR711q13.4Q9UBM7 details
Sterol 26-hydroxylase, mitochondrialCYP27A12q33-qterQ02318 details
Apolipoprotein A-IAPOA111q23-q24P02647 details
Delta(24)-sterol reductaseDHCR241p32.3Q15392 details
Nuclear receptor ROR-alphaRORA15q22.2P35398 details
Cholesterol 25-hydroxylaseCH25H10q23O95992 details
Cholesterol 24-hydroxylaseCYP46A114q32.1Q9Y6A2 details
Transporters
Protein NameGene NameLocusUniprot IDDetails
Multidrug resistance protein 1ABCB17q21.12P08183 details
ATP-binding cassette sub-family G member 2ABCG24q22Q9UNQ0 details
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Steryl-sulfataseSTSXp22.32P08842 details
Cholesterol 7-alpha-monooxygenaseCYP7A18q11-q12P22680 details
Cholesterol side-chain cleavage enzyme, mitochondrialCYP11A115q23-q24P05108 details
Sterol 26-hydroxylase, mitochondrialCYP27A12q33-qterQ02318 details
Nuclear receptor ROR-alphaRORA15q22.2P35398 details
Cholesterol 25-hydroxylaseCH25H10q23O95992 details
Cholesterol 24-hydroxylaseCYP46A114q32.1Q9Y6A2 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Nuclear receptor ROR-alphaRORA15q22.2P35398 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Nuclear receptor ROR-alphaRORA15q22.2P35398 details
Concentrations Data
Not Available
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
General ReferencesNot Available

Only showing the first 10 proteins. There are 26 proteins in total.

Enzymes

General function:
Involved in phosphatidylcholine-sterol O-acyltransferase activity
Specific function:
Central enzyme in the extracellular metabolism of plasma lipoproteins. Synthesized mainly in the liver and secreted into plasma where it converts cholesterol and phosphatidylcholines (lecithins) to cholesteryl esters and lysophosphatidylcholines on the surface of high and low density lipoproteins (HDLs and LDLs). The cholesterol ester is then transported back to the liver. Has a preference for plasma 16:0-18:2 or 18:O-18:2 phosphatidylcholines. Also produced in the brain by primary astrocytes, and esterifies free cholesterol on nascent APOE-containing lipoproteins secreted from glia and influences cerebral spinal fluid (CSF) APOE- and APOA1 levels. Together with APOE and the cholesterol transporter ABCA1, plays a key role in the maturation of glial-derived, nascent lipoproteins. Required for remodeling high-density lipoprotein particles into their spherical forms.
Gene Name:
LCAT
Uniprot ID:
P04180
Molecular weight:
49577.545
General function:
Involved in lipid metabolic process
Specific function:
Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:
LIPA
Uniprot ID:
P38571
Molecular weight:
45418.71
General function:
Lipid transport and metabolism
Specific function:
Catalyzes fat and vitamin absorption. Acts in concert with pancreatic lipase and colipase for the complete digestion of dietary triglycerides.
Gene Name:
CEL
Uniprot ID:
P19835
Molecular weight:
79666.385
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
General function:
Involved in catalytic activity
Specific function:
Conversion of sulfated steroid precursors to estrogens during pregnancy.
Gene Name:
STS
Uniprot ID:
P08842
Molecular weight:
65491.72
General function:
Involved in acyl-CoA binding
Specific function:
Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase. May provide cholesteryl esters for lipoprotein secretion from hepatocytes and intestinal mucosa.
Gene Name:
SOAT2
Uniprot ID:
O75908
Molecular weight:
59895.735
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes a rate-limiting step in cholesterol catabolism and bile acid biosynthesis by introducing a hydrophilic moiety at position 7 of cholesterol. Important for cholesterol homeostasis.
Gene Name:
CYP7A1
Uniprot ID:
P22680
Molecular weight:
57660.155
General function:
Involved in acyl-CoA binding
Specific function:
Catalyzes the formation of fatty acid-cholesterol esters. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:
SOAT1
Uniprot ID:
P35610
Molecular weight:
58130.665
General function:
Involved in 7-dehydrocholesterol reductase activity
Specific function:
Production of cholesterol by reduction of C7-C8 double bond of 7-dehydrocholesterol (7-DHC).
Gene Name:
DHCR7
Uniprot ID:
Q9UBM7
Molecular weight:
54488.98
General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the first step in the oxidation of the side chain of sterol intermediates; the 27-hydroxylation of 5-beta-cholestane-3-alpha,7-alpha,12-alpha-triol. Has also a vitamin D3-25-hydroxylase activity.
Gene Name:
CYP27A1
Uniprot ID:
Q02318
Molecular weight:
60234.28

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
General function:
Involved in ATP binding
Specific function:
Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from the brain. May be involved in brain-to-blood efflux. Appears to play a major role in the multidrug resistance phenotype of several cancer cell lines. When overexpressed, the transfected cells become resistant to mitoxantrone, daunorubicin and doxorubicin, display diminished intracellular accumulation of daunorubicin, and manifest an ATP- dependent increase in the efflux of rhodamine 123
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular weight:
72313.5

Only showing the first 10 proteins. There are 26 proteins in total.