RefMet Compound Details

RefMet ID, RefMet name, exact mass and formula
RefMet ID	RM0135688
RefMet name	20-Hydroxycholesterol
Systematic name	cholest-5-en-3beta,20-diol
Synonyms	PubChem Synonyms
Sum Composition	ST 27:1;O2	View other entries in RefMet with this sum composition
Exact mass	402.349780 (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	C27H46O2	View other entries in RefMet with this formula
Molecular descriptors
Molfile	34489 (Download molfile/View MW Metabolite Database details)
InChI	InChI=1S/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6- 7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27-/m0/s1
InChIKey	MCKLJFJEQRYRQT-APGJSSKUSA-N	View other enantiomers/diastereomers of this metabolite in RefMet
SMILES	CC(C)CCC[C@@](C)([C@H]1CC[C@H]2[C@@H]3CC=C4C[C@H](CC[C@]4(C)[C@H]3CC[C@]12C)O)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 20-Hydroxycholesterol 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 20-Hydroxycholesterol
External Links
Pubchem CID	121935
LIPID MAPS	LMST01010201
ChEBI ID	1296
KEGG ID	C05500
MetaCyc ID	2-HYDROXY-CHOLESTEROL
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 20-Hydroxycholesterol

Rxn ID	KEGG Reaction	Enzyme
R01454	Cholesterol + Oxygen + 2 H+ + 2 Reduced adrenal ferredoxin <=> 20alpha-Hydroxycholesterol + H2O + 2 Oxidized adrenal ferredoxin	Cholesterol:oxygen oxidoreductase (side-chain-cleaving)
R04853	20alpha-Hydroxycholesterol + [Reduced NADPH---hemoprotein reductase] + Oxygen <=> 17alpha,20alpha-Dihydroxycholesterol + [Oxidized NADPH---hemoprotein reductase] + H2O	20alpha-hydroxycholesterol,NADPH-hemoprotein reductase:oxygen oxidoreductase (17alpha-hydroxylating)
R04854	20alpha-Hydroxycholesterol + Oxygen + 2 Reduced adrenal ferredoxin + 2 H+ <=> 20alpha,22beta-Dihydroxycholesterol + H2O + 2 Oxidized adrenal ferredoxin	20alpha-Hydroxycholesterol:oxygen oxidoreductase (side-chain-cleaving)

Table of KEGG human pathways containing 20-Hydroxycholesterol

Pathway ID	Human Pathway	# of reactions
hsa00140	Steroid hormone biosynthesis	3