CHEBI:17823 - calcitriol

Main ChEBI Ontology Automatic Xrefs
ChEBI Name calcitriol
ChEBI ID CHEBI:17823
Definition A hydroxycalciol that is calcidiol in which the pro-S hydrogen of calcidiol is replaced by a hydroxy group. It is the active form of vitamin D3, produced fom calciol via hydoxylation in the liver to form calcidiol, which is subsequently oxidised in the kidney to give calcitriol.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:19209, CHEBI:46435, CHEBI:3307, CHEBI:13932
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Formula C27H44O3
Net Charge 0
Average Mass 416.63646
InChI InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18-,22-,23-,24+,25+,27-/m1/s1
InChIKey GMRQFYUYWCNGIN-NKMMMXOESA-N
SMILES [H][C@@]1(CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C)[C@H](C)CCCC(C)(C)O
Metabolite of Species Details
Homo sapiens (NCBI:9606) See: DOI
Roles Classification
Biological Role(s): immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
calcium channel modulator
A membrane transport modulator that is able to regulate intracellular calcium levels.
vitamin
An organic substance that is distributed in foodstuffs, is distinct from the main organic components of food (protein, carbohydrate and fat) and is needed for the normal nutrition of the organism in question. The term "vitamines" (from vita + amines) was coined in 1912 by Casimir Funk, who believed that these compounds were amines.
calcium channel agonist
Agents that increase calcium influx into calcium channels of excitable tissues.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
hormone
Originally referring to an endogenous compound that is formed in specialized organ or group of cells and carried to another organ or group of cells, in the same organism, upon which it has a specific regulatory function, the term is now commonly used to include non-endogenous, semi-synthetic and fully synthetic analogues of such compounds.
fat-soluble vitamin
Vitamins like A, D, E and K that dissolve in fats and are stored in body tissues. Unlike the water-soluble vitamins, these are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess.
(via vitamin D )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
antipsoriatic
A drug used to treat psoriasis.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
bone density conservation agent
An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing calcitriol (CHEBI:17823) has role antineoplastic agent (CHEBI:35610)
calcitriol (CHEBI:17823) has role antipsoriatic (CHEBI:50748)
calcitriol (CHEBI:17823) has role bone density conservation agent (CHEBI:50646)
calcitriol (CHEBI:17823) has role calcium channel agonist (CHEBI:38807)
calcitriol (CHEBI:17823) has role calcium channel modulator (CHEBI:38808)
calcitriol (CHEBI:17823) has role hormone (CHEBI:24621)
calcitriol (CHEBI:17823) has role human metabolite (CHEBI:77746)
calcitriol (CHEBI:17823) has role immunomodulator (CHEBI:50846)
calcitriol (CHEBI:17823) has role metabolite (CHEBI:25212)
calcitriol (CHEBI:17823) has role nutraceutical (CHEBI:50733)
calcitriol (CHEBI:17823) has role vitamin (CHEBI:33229)
calcitriol (CHEBI:17823) is a D3 vitamins (CHEBI:73558)
calcitriol (CHEBI:17823) is a hydroxycalciol (CHEBI:47042)
calcitriol (CHEBI:17823) is a triol (CHEBI:27136)
Incoming 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (CHEBI:73927) has functional parent calcitriol (CHEBI:17823)
1α,25-dihydroxy-2β-(4-hydroxybutoxy)vitamin D3 (CHEBI:73929) has functional parent calcitriol (CHEBI:17823)
18-acetoxy-1α,25-dihydroxyvitamin D3 (CHEBI:73917) has functional parent calcitriol (CHEBI:17823)
calcitriol 26,23-lactone (CHEBI:47837) has functional parent calcitriol (CHEBI:17823)
IUPAC Name
(1S,3R,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
INNs Sources
calcitriol ChEBI
calcitriol WHO MedNet
calcitriol WHO MedNet
calcitriolum ChEBI
Synonyms Sources
(1α,3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol ChemIDplus
(1S,3R,5Z,7E)-9,10-secocholesta-5,7,10-triene-1,3,25-triol PDBeChem
(5Z,7E)-(1S,3R)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol JCBN
1,25-DHCC ChemIDplus
1-alpha-25-Dihydroxyvitamin D3 KEGG COMPOUND
1α,25(OH)2D3 ChEBI
1α,25-dihydroxycholecalciferol JCBN
1α,25-dihydroxyvitamin D3 ChemIDplus
5-{2-[1-(5-HYDROXY-1,5-DIMETHYL-HEXYL)-7A-METHYL-OCTAHYDRO-INDEN-4-YLIDENE]-ETHYLIDENE}-4-METHYLENE-CYCLOHEXANE-1,3-DIOL PDBeChem
Calcitriol KEGG COMPOUND
calcitriol UniProt
Brand Names Sources
Calcijex DrugBank
Decostriol DrugBank
Rocaltrol KEGG DRUG
Database Links Databases
C01673 KEGG COMPOUND
Calcitriol Wikipedia
CALCITRIOL MetaCyc
D00129 KEGG DRUG
DB00136 DrugBank
LMST03020258 LIPID MAPS
VDX PDBeChem
View more database links
Registry Numbers Types Sources
2227647 Beilstein Registry Number Beilstein
2227647 Reaxys Registry Number Reaxys
32222-06-3 CAS Registry Number KEGG COMPOUND
32222-06-3 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10217585 PubMed citation CiteXplore
15928596 PubMed citation CiteXplore
19429426 PubMed citation CiteXplore
20599255 PubMed citation CiteXplore
22905919 PubMed citation CiteXplore
23103122 PubMed citation CiteXplore
23144765 PubMed citation CiteXplore
Last Modified
20 April 2015