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CHEBI:32176 - tacalcitol

Default Structure
ChEBI IDCHEBI:32176
ChEBI Nametacalcitol
Stars
DefinitionA hydroxy seco-steroid that is calciol which carries hydroxy groups at positions 1S and 24R. It is a vitamin D3 analog which is used for the treatment of psoriasis vulgaris in adults, especially on the scalp.
Last Modified23 November 2020
DownloadsMolfile
FormulaC27H44O3
Net Charge0
Average Mass416.646
Monoisotopic Mass416.32905
SMILES[H][C@@]12CC[C@]([H])([C@H](C)CC[C@@H](O)C(C)C)[C@@]1(C)CCC/C2=C\C=C1\C[C@@H](O)C[C@H](O)C1=C
InChIInChI=1S/C27H44O3/c1-17(2)25(29)13-8-18(3)23-11-12-24-20(7-6-14-27(23,24)5)9-10-21-15-22(28)16-26(30)19(21)4/h9-10,17-18,22-26,28-30H,4,6-8,11-16H2,1-3,5H3/b20-9+,21-10-/t18-,22-,23-,24+,25-,26+,27-/m1/s1
InChIKeyBJYLYJCXYAMOFT-RSFVBTMBSA-N
Wikipedia
Roles Classification
Biological Roles:
vitamin D receptor agonist  An agonist that binds to and activates vitamin D receptors
fat-soluble vitamin (role)  Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess.
Applications:
antipsoriatic  A drug used to treat psoriasis.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
tacalcitol (CHEBI:32176) has functional parent calciol (CHEBI:28940)
tacalcitol (CHEBI:32176) has role antineoplastic agent (CHEBI:35610)
tacalcitol (CHEBI:32176) has role antipsoriatic (CHEBI:50748)
tacalcitol (CHEBI:32176) has role vitamin D receptor agonist (CHEBI:139503)
tacalcitol (CHEBI:32176) is a D3 vitamins (CHEBI:73558)
tacalcitol (CHEBI:32176) is a hydroxy seco-steroid (CHEBI:36853)
tacalcitol (CHEBI:32176) is a seco-cholestane (CHEBI:36818)
tacalcitol (CHEBI:32176) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
(1S,3R,5Z,7E,24R)-9,10-secocholesta-5,7,10-triene-1,3,24-triol
INNs  Source
tacalcitolWHO MedNet
tacalcitolWHO MedNet
tacalcitolWHO MedNet
tacalcitolumWHO MedNet
Synonyms  Source
(1α,24R)-1,24-dihydroxyvitamin D3KEGG COMPOUND
1-α,24(R)-dihydroxyvitamin D3ChemIDplus
PRI 2191ChemIDplus
PRI-2191ChEBI
TV 02ChemIDplus
TV-02ChemIDplus
Brand Name  Source
BonalfaKEGG DRUG
Manual XrefsDatabases
4446823ChemSpider
4727DrugCentral
C12919KEGG COMPOUND
D08554KEGG DRUG
DB13689DrugBank
TacalcitolWikipedia
Registry NumbersSources
CAS:57333-96-7ChemIDplus
Citations