Cannabis Compound Database: Showing Compound Card for Cholesterol (CDB004794)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (15)transporters (2) Show 26 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:37:27 UTC

Updated at

2020-12-07 19:10:57 UTC

CannabisDB ID

CDB004794

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Cholesterol

Description

Cholesterol, 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(3beta,14beta,17alpha)-Cholest-5-en-3-ol	ChEBI
Cholest-5-en-3beta-ol	ChEBI
Cholesterin	ChEBI
(3b,14b,17a)-Cholest-5-en-3-ol	Generator
(3Β,14β,17α)-cholest-5-en-3-ol	Generator
Cholest-5-en-3b-ol	Generator
Cholest-5-en-3β-ol	Generator
(3Β)-cholest-5-en-3-ol	HMDB
(3beta)-Cholest-5-en-3-ol	HMDB
3Β-hydroxycholest-5-ene	HMDB
3beta-Hydroxycholest-5-ene	HMDB
5:6-Cholesten-3β-ol	HMDB
5:6-Cholesten-3beta-ol	HMDB
(-)-Cholesterol	HMDB
Cholesterine	HMDB
Cholesterol base H	HMDB
Cholesteryl alcohol	HMDB
Cholestrin	HMDB
Cholestrol	HMDB
Cordulan	HMDB
Dastar	HMDB
Dusoline	HMDB
Dusoran	HMDB
Dythol	HMDB
Fancol CH	HMDB
Hydrocerin	HMDB
Kathro	HMDB
Lanol	HMDB
Super hartolan	HMDB
Tegolan	HMDB
Cholesterol	HMDB
delta5-Cholesten-3beta-ol	PhytoBank
Δ5-Cholesten-3β-ol	PhytoBank

Chemical Formula

C₂₇H₄₆O

Average Molecular Weight

386.65

Monoisotopic Molecular Weight

386.3549

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 Number

80356-14-5

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 Key

HVYWMOMLDIMFJA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Cholestane steroids

Direct Parent

Cholesterols 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 Framework

Aliphatic homopolycyclic compounds

External Descriptors

cholestanoid (CHEBI:16113 )
3beta-sterol (CHEBI:16113 )
cholestane (C00187 )
Cholesterol and derivatives (C00187 )
Cholestane and derivatives (C00187 )
Cholesterol and derivatives (LMST01010001 )

Ontology

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Role

Indirect biological role:

Atherogen

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Biological role:

Molecular messenger:

Signaling molecule

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	148 °C	Not Available
Boiling Point	360 °C	Wikipedia
Water Solubility	9.5e-05 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.02	ALOGPS
logP	7.11	ChemAxon
logS	-7.1	ALOGPS
pKa (Strongest Acidic)	18.2	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	120.62 m³·mol⁻¹	ChemAxon
Polarizability	50.64 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0a4l-7922000000-36e8a5e1a77d2e71d1d1	2014-09-20	View Spectrum
GC-MS	Cholesterol, 1 TMS, GC-MS Spectrum	splash10-004i-3911000000-52f5261007adc218f8f8	Spectrum
GC-MS	Cholesterol, non-derivatized, GC-MS Spectrum	splash10-052b-2932000000-1667c83d002043a59fff	Spectrum
GC-MS	Cholesterol, non-derivatized, GC-MS Spectrum	splash10-000l-9527000000-5529a262047f5369c9c1	Spectrum
GC-MS	Cholesterol, non-derivatized, GC-MS Spectrum	splash10-0mkr-2954000000-60e7d1f5973e4de33dec	Spectrum
GC-MS	Cholesterol, non-derivatized, GC-MS Spectrum	splash10-014i-1009000000-e82b8e23dedb45ce70e6	Spectrum
GC-MS	Cholesterol, non-derivatized, GC-MS Spectrum	splash10-056v-2900000000-04687c9f19ff52ba4654	Spectrum
Predicted GC-MS	Cholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05i3-1109000000-8cd386b595bd5151c5a2	Spectrum
Predicted GC-MS	Cholesterol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-3104900000-698223f49da0b0c1cf81	Spectrum
Predicted GC-MS	Cholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cholesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cholesterol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 27V, positive	splash10-052u-0690000000-36b4aea6637bdf069b5d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-014i-3639000000-18a9275beb9bae48c1d7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-014j-4934000000-f755ada933cfcf53c303	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0002-5921000000-e7d43c825b9f6d45e679	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0532-5910000000-ce90c49b7429a03a65da	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-05nb-8900000000-2e8913fec7126b5b2a62	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0apl-9600000000-3096c7a78c3dd2e6a538	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 50V, positive	splash10-067l-9400000000-1b57543b4cd0a05b9b3f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 60V, positive	splash10-0aru-9300000000-45a29b76dfefce3f01ca	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014r-0009000000-dccd68f70545aeac4fab	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05p9-3149000000-7f25daf2b709c7e0d177	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0c00-6269000000-5333d0216e01a3e43367	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-dc853b29b9e884bbb03b	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-09d9608700564a6fef78	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ldi-1009000000-96f6e67651380e1c959e	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0009000000-2d9cbc8b5b1fa392fb9b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abj-9173000000-9086873e4b65db1ced63	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8920000000-bd94fa538afb75d04765	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-c037f2d2f217e99b79ac	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0009000000-7de5154056e69e7319e1	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0009000000-96c53273291d4857bde4	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Steroidogenesis
Bile Acid Biosynthesis
Steroid Biosynthesis
Smith-Lemli-Opitz Syndrome (SLOS)		Not Available
CHILD Syndrome		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Phosphatidylcholine-sterol acyltransferase	LCAT	16q22.1	P04180	details
Lysosomal acid lipase/cholesteryl ester hydrolase	LIPA	10q23.2-q23.3	P38571	details
Bile salt-activated lipase	CEL	9q34.3	P19835	details
Sulfotransferase family cytosolic 2B member 1	SULT2B1	19q13.3	O00204	details
Steryl-sulfatase	STS	Xp22.32	P08842	details
Sterol O-acyltransferase 2	SOAT2	12q13.13	O75908	details
Cholesterol 7-alpha-monooxygenase	CYP7A1	8q11-q12	P22680	details
Sterol O-acyltransferase 1	SOAT1	1q25	P35610	details
7-dehydrocholesterol reductase	DHCR7	11q13.4	Q9UBM7	details
Sterol 26-hydroxylase, mitochondrial	CYP27A1	2q33-qter	Q02318	details
Apolipoprotein A-I	APOA1	11q23-q24	P02647	details
Delta(24)-sterol reductase	DHCR24	1p32.3	Q15392	details
Nuclear receptor ROR-alpha	RORA	15q22.2	P35398	details
Cholesterol 25-hydroxylase	CH25H	10q23	O95992	details
Cholesterol 24-hydroxylase	CYP46A1	14q32.1	Q9Y6A2	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Multidrug resistance protein 1	ABCB1	7q21.12	P08183	details
ATP-binding cassette sub-family G member 2	ABCG2	4q22	Q9UNQ0	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Steryl-sulfatase	STS	Xp22.32	P08842	details
Cholesterol 7-alpha-monooxygenase	CYP7A1	8q11-q12	P22680	details
Cholesterol side-chain cleavage enzyme, mitochondrial	CYP11A1	15q23-q24	P05108	details
Sterol 26-hydroxylase, mitochondrial	CYP27A1	2q33-qter	Q02318	details
Nuclear receptor ROR-alpha	RORA	15q22.2	P35398	details
Cholesterol 25-hydroxylase	CH25H	10q23	O95992	details
Cholesterol 24-hydroxylase	CYP46A1	14q32.1	Q9Y6A2	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Nuclear receptor ROR-alpha	RORA	15q22.2	P35398	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Nuclear receptor ROR-alpha	RORA	15q22.2	P35398	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000067

DrugBank ID

DB04540

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013269

KNApSAcK ID

C00003648

Chemspider ID

Not Available

KEGG Compound ID

C00187

BioCyc ID

CHOLESTEROL

BiGG ID

Not Available

Wikipedia Link

Cholesterol

METLIN ID

Not Available

PubChem Compound

5997

PDB ID

Not Available

ChEBI ID

16113

References

General References

Not Available

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

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Enzymes

Enzyme Details

1. Phosphatidylcholine-sterol acyltransferase

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

Enzyme Details

2. Lysosomal acid lipase/cholesteryl ester hydrolase

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

Enzyme Details

3. Bile salt-activated lipase

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

Enzyme Details

4. Sulfotransferase family cytosolic 2B member 1

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

Enzyme Details

5. Steryl-sulfatase

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

Enzyme Details

6. Sterol O-acyltransferase 2

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

Enzyme Details

7. Cholesterol 7-alpha-monooxygenase

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

Enzyme Details

8. Sterol O-acyltransferase 1

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

Enzyme Details

9. 7-dehydrocholesterol reductase

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

Enzyme Details

10. Sterol 26-hydroxylase, mitochondrial

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

Enzyme Details

1. Multidrug resistance protein 1

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

Enzyme Details

2. ATP-binding cassette sub-family G member 2

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.

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Showing Compound Card for Cholesterol (CDB004794)

Structure for CDB004794 (Cholesterol)

Enzymes

Transporters