Compound
lanosterol
A triterpene that derives from the chair-boat-chair-boat folding of 2,3-oxidosqualene. It is metabolized to cholesterol and cucurbitacins.
Structure
Loading the model…
- Class
- Organic compound
- Formula
- C30H50O
- Mass
- 426.729 g/mol
- Charge
- 0
- InChIKey
- CAHGCLMLTWQZNJ-BQNIITSRSA-N
- SMILES
- [H][C@@]12CCC3=C(CC[C@@]4(C)[C@@]3(C)CC[C@]4([H])[C@H](C)CCC=C(C)C)[C@@]1(C)CC[C@H](O)C2(C)C
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
3 entities
3 entities reached.
What the reference databases state
Chemical structure
- 24,25-dihydrolanosterol has the functional parent lanosterolCompoundChEBI CHEBI:28113Inferred only
- 4,4-dimethyl-5alpha-cholesta-8,24-dien-3beta-ol has the functional parent lanosterolCompoundChEBI CHEBI:18364Inferred only
Statements
9 statements
9 statements · 2 reference databases · Subject: lanosterol · Sources: Human-GEM, Rhea
- (S)-2,3-epoxysqualene is converted to lanosterolCompoundHuman-GEM MAR01473Inferred only
- (S)-2,3-epoxysqualene is converted to lanosterolCompoundHuman-GEM MAR01498Inferred only
- lanosterol is converted to 24,25-dihydrolanosterolCompoundHuman-GEM MAR01535Inferred only
- lanosterol is converted to 4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-olCompoundHuman-GEM MAR03598Inferred only
- lanosterol is metabolised by CYP4F8ProteinHuman-GEM MAR01497Inferred only
- lanosterol is metabolised by CYP51A1ProteinRhea RHEA:25286Inferred only
- lanosterol is metabolised by CYP51A1ProteinHuman-GEM MAR01477Inferred only
- lanosterol is metabolised by CYP51A1ProteinHuman-GEM MAR02200Inferred only
- lanosterol is a substrate of DHCR24ProteinHuman-GEM MAR01535Inferred only
Reactions
20 reactions
(S)-2,3-epoxysqualenelanosterol
Catalysed by LSS
Reaction pageLeft to rightBalancedEC 5.4.99.7GO:0005829
Human-GEM MAR01473CC BY 4.0Reference data
proton+lanosterol+NADPH(4-)+dioxygenMAM00939c+water+NADP(3-)
Catalysed by CYP51A1
Reaction pageLeft to rightBalancedEC 1.14.14.154GO:0005829
Human-GEM MAR01477CC BY 4.0Reference data
2proton+lanosterol+3NADPH(4-)+3dioxygen4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol+formic acid+4water+3NADP(3-)
Catalysed by CYP4F8
Reaction pageLeft to rightBalancedEC 1.14.14.1GO:0005829
Human-GEM MAR01497CC BY 4.0Reference data
(S)-2,3-epoxysqualenelanosterol
Catalysed by LSS
Reaction pageLeft to rightBalancedEC 5.4.99.7GO:0005783
Human-GEM MAR01498CC BY 4.0Reference data
proton+lanosterol+NADPH(4-)24,25-dihydrolanosterol+NADP(3-)
Catalysed by DHCR24
Reaction pageLeft to rightBalancedEC 1.3.1.72GO:0005829
Human-GEM MAR01535CC BY 4.0Reference data
2proton+lanosterol+3NADPH(4-)+3dioxygen4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol+formic acid+4water+3NADP(3-)
Catalysed by CYP51A1
Reaction pageLeft to rightBalancedEC 1.14.14.154GO:0005783
Human-GEM MAR02200CC BY 4.0Reference data
Reaction pageLeft to rightBalancedGO:0005783, GO:0005777
Human-GEM MAR02274CC BY 4.0Reference data
carbon dioxide+3lanosterol34,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol+2water+4MAM03357c
Reaction pageLeft to rightBalancedGO:0005829
Human-GEM MAR03598CC BY 4.0Reference data
Reaction pageReversibleBalance undeterminableGO:0005615
Human-GEM MAR11441CC BY 4.0Reference data
Reaction pageLeft to rightBalancedGO:0005829, GO:0005615
Human-GEM MAR11972CC BY 4.0Reference data
Reaction pageLeft to rightBalancedGO:0005783, GO:0005829
Human-GEM MAR11981CC BY 4.0Reference data
(S)-2,3-epoxysqualenelanosterol
Catalysed by LSS
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:14621CC BY 4.0Reference data
Other names
9 names
Resolves to: lanosterol
- Also called
- (3beta,5alpha)-4,4,14-trimethylcholesta-8,24-dien-3-ol(3beta)-lanosta-8,24-dien-3-ol(3β,5α)-4,4,14-trimethylcholesta-8,24-dien-3-ol(3β)-lanosta-8,24-dien-3-ol4,4',14alpha-Trimethyl-5alpha-cholesta-8,24-dien-3beta-olLanosterinST 30:2;O
- Systematic name
- lanosta-8,24-dien-3beta-ollanosta-8,24-dien-3β-ol