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Record Information
Version1.0
Creation Date2016-09-30 22:19:13 UTC
Update Date2020-06-04 22:59:16 UTC
BMDB IDBMDB0000067
Secondary Accession Numbers
  • BMDB00067
Metabolite 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.
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 Weight386.6535
Monoisotopic Molecular Weight386.354866094
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number57-88-5
SMILESNot Available
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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Lysosome
  • Membrane
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Endoplasmic reticulum
  • Golgi
  • Lysosome
  • Membrane
  • Mitochondria
Biospecimen Locations
  • All Tissues
  • Blood
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Semen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
BloodDetected and Quantified3341.493 +/- 370.616 uMNot SpecifiedNot Specified
Normal
    • Abdullah BASOGLU,...
details
BloodDetected and Quantified3290 uMNot SpecifiedNot Specified
Normal
details
BloodDetected and Quantified775.888 uMNot SpecifiedNot Specified
Normal
    • Arthur K. Anderso...
details
BloodDetected and Quantified5560534.173 uMNot SpecifiedNot Specified
Normal
    • M.J. Abarghuei, Y...
details
BloodDetected and Quantified4189797.842 uMNot SpecifiedNot Specified
Normal
    • M.J. Abarghuei, Y...
details
BloodDetected and Quantified4138071.943 uMNot SpecifiedNot Specified
Normal
    • M.J. Abarghuei, Y...
details
BloodDetected and Quantified5431219.425 uMNot SpecifiedNot Specified
Normal
    • M.J. Abarghuei, Y...
details
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Trabi M, Keller M...
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified129.315 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified51.726 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified362.0813 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified103.452 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified103.452 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified129.315 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified51.726 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified51.726 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified51.726 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified51.726 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified155.178 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified155.178 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified362.0813 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified206.904 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified206.904 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified206.904 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified206.904 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified206.904 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified77.589 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified89.744 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified77.589 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified258.629 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified258.629 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified362.0813 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified362.0813 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified362.0813 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified362.0813 uMNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified101.383 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified51.726 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified51.726 uMNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Hanne Christine B...
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
SemenDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified1815.838 +/- 142.505 uMNot SpecifiedNot Specified
Left displaced abomasum (LDA)
    • Abdullah BASOGLU,...
details
BloodDetected and Quantified2317.320 +/- 236.387 uMNot SpecifiedNot Specified
Right displaced abomasum (RDA)
    • Abdullah BASOGLU,...
details
BloodDetected and Quantified2910 uMNot SpecifiedNot Specified
Treated with bovine somatotropin
details
HMDB IDHMDB0000067
DrugBank IDDB04540
Phenol Explorer Compound IDNot Available
FooDB 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]

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP3A28
Uniprot ID:
P79102
Molecular weight:
58152.0
Reactions
Cholesterol + NADPH + Oxygen → 24-Hydroxycholesterol + NADP + Waterdetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name:
PTGIS
Uniprot ID:
Q29626
Molecular weight:
56629.0
Reactions
Cholesterol + 3 NADPH + 3 Oxygen → 27-Hydroxycholesterol +3 NADP +4 Waterdetails
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
A cytochrome P450 monooxygenase that catalyzes the side-chain hydroxylation and cleavage of cholesterol to pregnenolone, the precursor of most steroid hormones (PubMed:11412116). Catalyzes three sequential oxidation reactions of cholesterol, namely the hydroxylation at C22 followed with the hydroxylation at C20 to yield 20R,22R-hydroxycholesterol that is further cleaved between C20 and C22 to yield the C21-steroid pregnenolone and 4-methylpentanal (PubMed:11412116). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate and reducing the second into a water molecule. Two electrons are provided by NADPH via a two-protein mitochondrial transfer system comprising flavoprotein FDXR (adrenodoxin/ferredoxin reductase) and nonheme iron-sulfur protein FDX1 or FDX2 (adrenodoxin/ferredoxin) (PubMed:11412116).
Gene Name:
CYP11A1
Uniprot ID:
P00189
Molecular weight:
60333.0
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:
Q5E9J5
Molecular weight:
54271.0
General function:
Involved in C-8 sterol isomerase activity
Specific function:
Not Available
Gene Name:
EBP
Uniprot ID:
Q3ZBT8
Molecular weight:
26480.0
Reactions
7-Dehydrocholesterol + NADPH → Cholesterol + NADPdetails
General function:
Signal transduction mechanisms
Specific function:
Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism, but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1649835).
Gene Name:
TSPO
Uniprot ID:
P30535
Molecular weight:
18927.0
General function:
Involved in sequence-specific DNA binding
Specific function:
Ligand-activated transcription factor. Receptor for bile acids (BAs) such as chenodeoxycholic acid (CDCA), lithocholic acid, deoxycholic acid (DCA) and allocholic acid (ACA). Plays a essential role in BA homeostasis through the regulation of genes involved in BA synthesis, conjugation and enterohepatic circulation. Also regulates lipid and glucose homeostasis and is involved innate immune response. The FXR-RXR heterodimer binds predominantly to farnesoid X receptor response elements (FXREs) containing two inverted repeats of the consensus sequence 5'-AGGTCA-3' in which the monomers are spaced by 1 nucleotide (IR-1) but also to tandem repeat DR1 sites with lower affinity, and can be activated by either FXR or RXR-specific ligands. It is proposed that monomeric nuclear receptors such as NR5A2/LRH-1 bound to coregulatory nuclear responsive element (NRE) halfsites located in close proximity to FXREs modulate transcriptional activity. In the liver activates transcription of the corepressor NR0B2 thereby indirectly inhibiting CYP7A1 and CYP8B1 (involved in BA synthesis) implicating at least in part histone demethylase KDM1A resulting in epigenomic repression, and SLC10A1/NTCP (involved in hepatic uptake of conjugated BAs). Activates transcription of the repressor MAFG (involved in regulation of BA synthesis). Activates transcription of SLC27A5/BACS and BAAT (involved in BA conjugation), ABCB11/BSEP (involved in bile salt export) by directly recruiting histone methyltransferase CARM1, and ABCC2/MRP2 (involved in secretion of conjugated BAs) and ABCB4 (involved in secretion of phosphatidylcholine in the small intestine). Activates transcription of SLC27A5/BACS and BAAT (involved in BA conjugation), ABCB11/BSEP (involved in bile salt export) by directly recruiting histone methyltransferase CARM1, and ABCC2/MRP2 (involved in secretion of conjugated BAs) and ABCB4 (involved in secretion of phosphatidylcholine in the small intestine). In the intestine activates FGF19 expression and secretion leading to hepatic CYP7A1 repression. The function also involves the coordinated induction of hepatic KLB/beta-klotho expression. Regulates transcription of liver UGT2B4 and SULT2A1 involved in BA detoxification; binding to the UGT2B4 promoter seems to imply a monomeric transactivation independent of RXRA. Modulates lipid homeostasis by activating liver NR0B2/SHP-mediated repression of SREBF1 (involved in de novo lipogenesis), expression of PLTP (involved in HDL formation), SCARB1 (involved in HDL hepatic uptake), APOE, APOC1, APOC4, PPARA (involved in beta-oxidation of fatty acids), VLDLR and SDC1 (involved in the hepatic uptake of LDL and IDL remnants), and inhibiting expression of MTTP (involved in VLDL assembly). Increases expression of APOC2 (promoting lipoprotein lipase activity implicated in triglyceride clearance). Transrepresses APOA1 involving a monomeric competition with NR2A1 for binding to a DR1 element. Also reduces triglyceride clearance by inhibiting expression of ANGPTL3 and APOC3 (both involved in inhibition of lipoprotein lipase). Involved in glucose homeostasis by modulating hepatic gluconeogenesis through activation of NR0B2/SHP-mediated repression of respective genes. Modulates glycogen synthesis (inducing phosphorylation of glycogen synthase kinase-3). Modulates glucose-stimulated insulin secretion and is involved in insulin resistance. Involved in intestinal innate immunity. Plays a role in protecting the distal small intestine against bacterial overgrowth and preservation of the epithelial barrier. Down-regulates inflammatory cytokine expression in several types of immune cells including macrophages and mononuclear cells. Mediates trans-repression of TLR4-induced cytokine expression; the function seems to require its sumoylation and prevents N-CoR nuclear receptor corepressor clearance from target genes such as IL1B and NOS2. Involved in the TLR9-mediated protective mechanism in intestinal inflammation. Plays an anti-inflammatory role in liver inflammation; proposed to inhibit proinflammatory (but not antiapoptotic) NF-kappa-B signaling.
Gene Name:
NR1H4
Uniprot ID:
Q3SZL0
Molecular weight:
55460.0
General function:
Energy production and conversion
Specific function:
Not Available
Gene Name:
DHCR24
Uniprot ID:
A6QR14
Molecular weight:
60173.0
Reactions
Desmosterol + NADPH → Cholesterol + NADPdetails
General function:
Cell cycle control, cell division, chromosome partitioning
Specific function:
Participates in the reverse transport of cholesterol from tissues to the liver for excretion by promoting cholesterol efflux from tissues and by acting as a cofactor for the lecithin cholesterol acyltransferase (LCAT). As part of the SPAP complex, activates spermatozoa motility.
Gene Name:
APOA1
Uniprot ID:
P15497
Molecular weight:
30276.0
General function:
Involved in high-density lipoprotein binding
Specific function:
Not Available
Gene Name:
SCARB1
Uniprot ID:
A4IFC6
Molecular weight:
56916.0
General function:
Involved in chloride channel activity
Specific function:
Not Available
Gene Name:
CFTR
Uniprot ID:
Q9TSX2
Molecular weight:
5369.0
General function:
Not Available
Specific function:
Escort protein required for cholesterol as well as lipid homeostasis. Regulates export of the SCAP/SREBF complex from the ER upon low cholesterol. Formation of a ternary complex with INSIG at high sterol concentrations leads to masking of an ER-export signal in SCAP and retention of the complex in the ER. Low sterol concentrations trigger release of INSIG, a conformational change in the SSC domain of SCAP, unmasking of the ER export signal, recruitment into COPII-coated vesicles, transport to the Golgi complex, proteolytic cleavage of SREBF in the Golgi, release of the transcription factor fragment of SREBF from the membrane, its import into the nucleus and up-regulation of LDLR, INSIG1 and the mevalonate pathway (By similarity).
Gene Name:
SCAP
Uniprot ID:
A6QM06
Molecular weight:
139701.0
General function:
Not Available
Specific function:
May be involved in the intracellular transport of sterols or other lipids. May bind cholesterol or other sterols (By similarity).
Gene Name:
STARD5
Uniprot ID:
A1A4M6
Molecular weight:
23573.0
General function:
Involved in lipoprotein metabolic process
Specific function:
Not Available
Gene Name:
APOM
Uniprot ID:
Q3ZBQ9
Molecular weight:
13027.0
General function:
Involved in cholesterol binding
Specific function:
Plays a key role in steroid hormone synthesis by enhancing the metabolism of cholesterol into pregnenolone. Mediates the transfer of cholesterol from the outer mitochondrial membrane to the inner mitochondrial membrane where it is cleaved to pregnenolone (By similarity).
Gene Name:
STAR
Uniprot ID:
Q28918
Molecular weight:
31871.0
General function:
Cell cycle control, cell division, chromosome partitioning
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q0ZCB4
Molecular weight:
27074.0
General function:
Cell cycle control, cell division, chromosome partitioning
Specific function:
Not Available
Gene Name:
APOE
Uniprot ID:
A7YWR0
Molecular weight:
36073.0
General function:
Involved in receptor activity
Specific function:
Receptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Receptor for HDL, mediating selective uptake of cholesteryl ether and HDL-dependent cholesterol efflux. Also facilitates the flux of free and esterified cholesterol between the cell surface and apoB-containing lipoproteins and modified lipoproteins, although less efficiently than HDL. May be involved in the phagocytosis of apoptotic cells, via its phosphatidylserine binding activity.
Gene Name:
SCARB1
Uniprot ID:
O18824
Molecular weight:
57610.0
General function:
Posttranslational modification, protein turnover, chaperones
Specific function:
A scaffold protein that connects plasma membrane proteins and regulatory components, regulating their surface expression in epithelial cells apical domains. May be involved in the coordination of a diverse range of regulatory processes for ion transport and second messenger cascades. In complex with SLC9A3R1, may cluster proteins that are functionally dependent in a mutual fashion and modulate the trafficking and the activity of the associated membrane proteins. May play a role in the cellular mechanisms associated with multidrug resistance through its interaction with ABCC2 and PDZK1IP1. May potentiate the CFTR chloride channel activity. Required for normal cell-surface expression of SCARB1. Plays a role in maintaining normal plasma cholesterol levels via its effects on SCARB1. Plays a role in the normal localization and function of the chloride-anion exchanger SLC26A6 to the plasma membrane in the brush border of the proximal tubule of the kidney. May be involved in the regulation of proximal tubular Na(+)-dependent inorganic phosphate cotransport therefore playing an important role in tubule function (By similarity).
Gene Name:
PDZK1
Uniprot ID:
Q3T0X8
Molecular weight:
57175.0
General function:
Not Available
Specific function:
Not Available
Gene Name:
LIPF
Uniprot ID:
Q29458
Molecular weight:
45231.0
Reactions
CE(22:2) + Water → Cholesterol + Palmitic aciddetails