CHEBI:32176 - tacalcitol

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ChEBI Name tacalcitol
ChEBI ID CHEBI:32176
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C27H44O3
Net Charge 0
Average Mass 416.646
Monoisotopic Mass 416.32905
InChI InChI=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
InChIKey BJYLYJCXYAMOFT-RSFVBTMBSA-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)CC[C@@H](O)C(C)C
Roles Classification
Biological Role(s): 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.
(via vitamin D )
Application(s): antipsoriatic
A drug used to treat psoriasis.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 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 Sources
tacalcitol WHO MedNet
tacalcitol WHO MedNet
tacalcitol WHO MedNet
tacalcitolum WHO MedNet
Synonyms Sources
(1α,24R)-1,24-dihydroxyvitamin D3 KEGG COMPOUND
1-α,24(R)-dihydroxyvitamin D3 ChemIDplus
PRI 2191 ChemIDplus
PRI-2191 ChEBI
TV 02 ChemIDplus
TV-02 ChemIDplus
Brand Name Source
Bonalfa KEGG DRUG
Manual Xrefs Databases
4446823 ChemSpider
4727 DrugCentral
C12919 KEGG COMPOUND
D08554 KEGG DRUG
DB13689 DrugBank
Tacalcitol Wikipedia
View more database links
Registry Number Type Source
57333-96-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
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Last Modified
23 November 2020