Compound
calcitriol
The physiologically active form of vitamin D. It is formed primarily in the kidney by enzymatic hydroxylation of 25-hydroxycholecalciferol (calcifediol). Its production is stimulated by low blood calcium levels and parathyroid hormone. Calcitriol increases intestinal absorption of calcium and phosphorus, and in concert with parathyroid hormone increases bone resorption.
Structure
Loading the model…
- Class
- Organic compound
- Formula
- C27H44O3
- Mass
- 416.646 g/mol
- Charge
- 0
- InChIKey
- GMRQFYUYWCNGIN-NKMMMXOESA-N
- SMILES
- [H][C@@]12CC[C@]([H])([C@H](C)CCCC(C)(C)O)[C@@]1(C)CCC/C2=CC=C1C[C@@H](O)C[C@H](O)C1=C
- Look it up
- ChEBIPubChemBy InChIKey
Identity from ChEBI, geometry from PubChem. Not evidence.
What it touches on the way
Mechanistic reach
4 entities
4 entities reached.
0 reported hops4 assembled from the scaffold
What the reference databases state
Regulatory determinations
LiverTox likelihood score ELiverTox
LiverTox Likelihood Score E — despite extensive use, no evidence that the agent has caused liver injury. Chapter: "Vitamin D". Source: LiverTox Master List (NBK571102).
The document·Public Domain (NLM/NIH)·Transcribed, not assessed
Chemical structure
- calcitriol 25-O-(beta-D-glucuronide) has the functional parent calcitriolCompoundChEBI CHEBI:139274Inferred only
Statements
10 statements
10 statements · 2 reference databases · Subject: calcitriol · Sources: Human-GEM, Rhea
- calcidiol is converted to calcitriolCompoundHuman-GEM MAR08008Inferred only
- calcidiol is converted to calcitriolCompoundHuman-GEM MAR02118Inferred only
- calcitriol is converted to calcitetrolCompoundHuman-GEM MAR02141Inferred only
- calcitriol is converted to calcitriol 25-O-(beta-D-glucuronide)CompoundRhea RHEA:55836Inferred only
- calcitriol is metabolised by CYP24A1ProteinRhea RHEA:49192Inferred only
- calcitriol is metabolised by CYP24A1ProteinHuman-GEM MAR02141Inferred only
- calcitriol is metabolised by CYP24A1ProteinRhea RHEA:24964Inferred only
- calcitriol is metabolised by UGT1A4ProteinRhea RHEA:55836Inferred only
- calcitriol is transported by CD36ProteinHuman-GEM MAR11815Inferred only
- calcitriol is transported by SCARB1ProteinHuman-GEM MAR11815Inferred only
Reactions
15 reactions
calcidiol+proton+NADPH(4-)+dioxygencalcitriol+water+NADP(3-)
Catalysed by CYP27B1 & CUBN & GC & LRP2
Reaction pageLeft to rightBalancedEC 1.14.15.18cytosol
Human-GEM MAR02118CC BY 4.0Reference data
Reaction pageReversibleBalancedcytosol, mitochondrial matrix
Human-GEM MAR02127CC BY 4.0Reference data
calcitriol+proton+NADPH(4-)+dioxygencalcitetrol+water+NADP(3-)
Catalysed by CYP24A1
Reaction pageLeft to rightBalancedEC 1.14.15.16mitochondrial matrix
Human-GEM MAR02141CC BY 4.0Reference data
Reaction pageLeft to rightBalancedcytosol, nucleus
Human-GEM MAR07750CC BY 4.0Reference data
calcidiol+proton+NADPH(4-)+dioxygencalcitriol+water+NADP(3-)
Catalysed by CYP27B1 & CUBN & GC & LRP2
Reaction pageLeft to rightBalancedEC 1.14.15.18mitochondrial matrix
Human-GEM MAR08008CC BY 4.0Reference data
Reaction pageLeft to rightBalancedextracellular space, cytosol
Human-GEM MAR11815CC BY 4.0Reference data
Reaction pageLeft to rightBalancedcytosol, extracellular space
Human-GEM MAR11964CC BY 4.0Reference data
Reaction pageReversibleBalance undeterminableextracellular space
Human-GEM MAR11965CC BY 4.0Reference data
calcidiol+2reduced [adrenodoxin]+dioxygen+2hydroncalcitriol+2oxidized [adrenodoxin]+water
Catalysed by CYP27B1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:20573CC BY 4.0Reference data
calcitriol+2reduced [adrenodoxin]+dioxygen+2hydroncalcitetrol+2oxidized [adrenodoxin]+water
Catalysed by CYP24A1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:24964CC BY 4.0Reference data
alfacalcidol+2reduced [adrenodoxin]+dioxygen+2hydroncalcitriol+2oxidized [adrenodoxin]+water
Reaction pageDirection not assertedBalance undeterminable
Rhea RHEA:46592CC BY 4.0Reference data
calcitriol+2reduced [adrenodoxin]+dioxygen+2hydron1alpha,23S,25-trihydroxycholecalciferol+2oxidized [adrenodoxin]+water
Catalysed by CYP24A1
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:49192CC BY 4.0Reference data
Where it reaches
8 systems, 17 regions, 60 tissues, 60 transporter routes — routes, not measurements: transporters known to carry calcitriol are expressed there, and no source reports it arriving.
Loading the model…
Other names
18 names
Resolves to: calcitriol
- Also called
- (1alpha,3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol(1S,3R,5Z,7E)-9,10-secocholesta-5,7,10-triene-1,3,25-triol(1α,3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol(5Z,7E)-(1S,3R)-9,10-seco-5,7,10(19)-cholestatriene-1,3,25-triol(5Z,7E)-(1S,3R)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol1-alpha-25-Dihydroxyvitamin D31,25-DHCC1alpha,25-dihydroxycholecalciferol1alpha,25-dihydroxyvitamin D31alpha,25(OH)2D31α,25-dihydroxycholecalciferol1α,25-dihydroxyvitamin D31α,25(OH)2D35-{2-[1-(5-HYDROXY-1,5-DIMETHYL-HEXYL)-7A-METHYL-OCTAHYDRO-INDEN-4-YLIDENE]-ETHYLIDENE}-4-METHYLENE-CYCLOHEXANE-1,3-DIOL
- Systematic name
- (1S,3R,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
- Sold as
- CalcijexDecostriolRocaltrol