RefMet Compound Details

RefMet ID, RefMet name, exact mass and formula
RefMet ID	RM0135639
RefMet name	Cholesterol
Systematic name	cholest-5-en-3beta-ol
Synonyms	PubChem Synonyms
Sum Composition	ST 27:1;O	View other entries in RefMet with this sum composition
Exact mass	386.354865 (neutral)	Calculate m/z: (Choose adduct) [M+H]+ [M+H-H2O]+ [M.]+ [M+2H]2+ [M+3H]3+ [M+4H]4+ [M+K]+ [M+2K]2+ [M+2K-H]+ [M+Na]+ [M+2Na]2+ [M+2Na-H]+ [M+Li]+ [M+2Li]2+ [M+NH4]+ [M.CH3]+ [M+Ag]+ [M+H+CH3OH]+ [M+H+CH3CN]+ [M+H+2CH3CN]+ [M+Na+CH3CN]+ [M.NaFormate+H]+ [M.NH4Formate+H]+ [M.TMSi]+ [M.tBuDMSi]+ [M+H-Hexose]+ [M+H-EtnP]+ [M+H-SerP]+ [M-H]- [M-H-H2O]- [M-CH3]- [M-2H]2- [M-3H]3- [M-4H]4- [M+Cl]- [M+OAc]- [M+Na-2H]- [M+K-2H]- [M.Formate]- [M.NaFormate-H]- [M.NH4Formate-H]- [M.F]- [M-H-Ser]- [M.HF2]- M(neutral)    View other RefMet entries with this exact (neutral) mass:   +/- 0.05 amu   +/- 0.1 amu   +/- 0.2 amu   +/- 0.5 amu
Formula	C27H46O	View other entries in RefMet with this formula
Molecular descriptors
Molfile	34361 (Download molfile/View MW Metabolite Database details)
InChI	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
InChIKey	HVYWMOMLDIMFJA-DPAQBDIFSA-N	View other enantiomers/diastereomers of this metabolite in RefMet
SMILES	CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O Run Tanimoto similarity search (with similarity coefficient >=0.6)
Chemical/Biochemical Classification
Super Class	Sterol Lipids
Main Class	Sterols
Sub Class	Cholesterols
Distribution of Cholesterol in NMDR studies
Species	Plot Species distribution
Sample source	Plot Sample source(tissue) distribution
Platform	Platform (MS/NMR) used for detection
Chromatography	Chromatography methods used for detection
Studies	NMDR Studies reporting Cholesterol
External Links
Pubchem CID	5997
LIPID MAPS	LMST01010001
ChEBI ID	16113
KEGG ID	C00187
HMDB ID	HMDB0000067
MetaCyc ID	CHOLESTEROL
EPA CompTox	DTXCID60204224
Spectral data for Cholesterol standards
MassBank(EU)	View MS spectra
Structural annotation level
Annotation level	1   (1:Known structure; 2:Known regiochemistry; 3:Partial structure; 4:Sum-composition)

Table of KEGG reactions in human pathways involving Cholesterol

Rxn ID	KEGG Reaction	Enzyme
R01451	Cholesterol + NAD+ <=> 7-Dehydrocholesterol + NADH + H+	Cholesterol:NAD+ delta7-oxidoreductase
R01454	Cholesterol + Oxygen + 2 H+ + 2 Reduced adrenal ferredoxin <=> 20alpha-Hydroxycholesterol + H2O + 2 Oxidized adrenal ferredoxin	Cholesterol:oxygen oxidoreductase (side-chain-cleaving)
R01456	Cholesterol + NADP+ <=> 7-Dehydrocholesterol + NADPH + H+	cholesterol:NADP+ delta7-oxidoreductase
R01457	Cholesterol + NADP+ <=> Desmosterol + H+ + NADPH	cholesterol:NADP+ Delta24-oxidoreductase
R01461	Acyl-CoA + Cholesterol <=> CoA + Cholesterol ester	Acyl-CoA:cholesterol O-acyltransferase
R01462	Cholesterol ester + H2O <=> Cholesterol + Fatty acid	cholesterol ester acylhydrolase
R01463	Cholesterol + Oxygen + [Reduced NADPH---hemoprotein reductase] <=> 7alpha-Hydroxycholesterol + [Oxidized NADPH---hemoprotein reductase] + H2O	cholesterol,NADPH-hemoprotein reductase:oxygen oxidoreductase (7alpha-hydroxylating)
R02723	Cholesterol + Oxygen + 2 Reduced adrenal ferredoxin + 2 H+ <=> 22(R)-Hydroxycholesterol + H2O + 2 Oxidized adrenal ferredoxin	Cholesterol + Oxygen + 2 Reduced adrenal ferredoxin + 2 H+ <=> 22(R)-Hydroxycholesterol + H2O + 2 Oxidized adrenal ferredoxin
R07207	Cholesterol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> Cerebrosterol + [Oxidized NADPH---hemoprotein reductase] + H2O	cholesterol,NADPH-hemoprotein reductase:oxygen oxidoreductase (24-hydroxylating)
R07218	Cholesterol + Reduced acceptor + Oxygen <=> 25-Hydroxycholesterol + Acceptor + H2O	cholesterol,hydrogen-donor:oxygen oxidoreductase (25-hydroxylating)
R08505	Cholesterol + Oxygen + 2 H+ + 2 Reduced adrenal ferredoxin <=> Cholest-5-ene-3beta,26-diol + H2O + 2 Oxidized adrenal ferredoxin	cholesterol 26-hydroxylase
R08941	Cholesterol + Sulfate <=> Cholesterol sulfate + H2O	Cholesterol-sulfate sulfohydrolase
R08977	Cholesterol + 3'-Phosphoadenylyl sulfate <=> Cholesterol sulfate + Adenosine 3',5'-bisphosphate	3'-phosphoadenylyl-sulfate:cholesterol sulfotransferase

Table of KEGG human pathways containing Cholesterol

Pathway ID	Human Pathway	# of reactions
hsa00100	Steroid biosynthesis	5
hsa00120	Primary bile acid biosynthesis	4
hsa00140	Steroid hormone biosynthesis	4
hsa01100	Metabolic pathways	2