calcitriol (CHEBI:17823)

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CHEBI:17823 - calcitriol

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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

Supplier Information	eMolecules:29541527, eMolecules:485907, Selleckchem:Calcitriol-(Rocaltrol), ZINC000100015048

Download	Molfile XML SDF

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M END): 25 ms

reading 74 atoms

ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false

1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them.

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74 atoms created

ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation

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Wikipedia	License
Calcitriol is a hormone and the active form of vitamin D, normally made in the kidney. It is also known as 1,25-dihydroxycholecalciferol. It binds to and activates the vitamin D receptor in the nucleus of the cell, which then increases the expression of many genes. Calcitriol increases blood calcium mainly by increasing the uptake of calcium from the intestines. It can be given as a medication for the treatment of low blood calcium and hyperparathyroidism due to kidney disease, low blood calcium due to hypoparathyroidism, osteoporosis, osteomalacia, and familial hypophosphatemia, and can be taken by mouth or by injection into a vein. Excessive amounts or intake can result in weakness, headache, nausea, constipation, urinary tract infections, and abdominal pain. Serious side effects may include high blood calcium and anaphylaxis. Calcitriol was identified as the active form of vitamin D in 1971 and the drug was approved for medical use in the United States in 1978. It is available as a generic medication. In 2022, it was the 254th most commonly prescribed medication in the United States, with more than 1 million prescriptions. It is on the World Health Organization's List of Essential Medicines.
Read full article at Wikipedia

Formula

C27H44O3

Net Charge

Average Mass

416.63646

Monoisotopic Mass

416.32905

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
Mus musculus (NCBI:txid10090)	Source: BioModels - MODEL1507180067 See: PubMed
Homo sapiens (NCBI:txid9606)	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. 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. mouse metabolite Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus). 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):	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 mouse metabolite (CHEBI:75771) calcitriol (CHEBI:17823) has role nutraceutical (CHEBI:50733) 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) AMCR277A (CHEBI:139026) has functional parent calcitriol (CHEBI:17823) AMCR277B (CHEBI:139027) has functional parent calcitriol (CHEBI:17823) calcitriol 25-O-(β-D-glucuronate) (CHEBI:139274) has functional parent calcitriol (CHEBI:17823) calcitriol 25-O-(β-D-glucuronide) (CHEBI:139600) 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

Manual Xrefs	Databases
466	DrugCentral
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	Reaxys Registry Number	Reaxys
32222-06-3	CAS Registry Number	KEGG COMPOUND
32222-06-3	CAS Registry Number	ChemIDplus

Citations

Alkharfy KM, Al-Daghri NM, Yakout SM, Ahmed M (2013)
Calcitriol attenuates weight-related systemic inflammation and ultrastructural changes in the liver in a rodent model.
Basic & clinical pharmacology & toxicology 112, 42-49 [PubMed:22905919]
[show Abstract]

Noyola-Martínez N, Díaz L, Avila E, Halhali A, Larrea F, Barrera D (2013)
Calcitriol downregulates TNF-α and IL-6 expression in cultured placental cells from preeclamptic women.
Cytokine 61, 245-250 [PubMed:23103122]
[show Abstract]

Kickler K, Ni Choileain S, Williams A, Richards A, Astier AL (2012)
Calcitriol modulates the CD46 pathway in T cells.
PloS one 7, e48486 [PubMed:23144765]
[show Abstract]

Kimura M, Rabbani Z, Mouraviev V, Tsivian M, Caso J, Satoh T, Baba S, Vujaskovic Z, Baust JM, Baust JG, Polascik TJ (2010)
Role of vitamin D(3) as a sensitizer to cryoablation in a murine prostate cancer model: preliminary in vivo study.
Urology 76, 764.e14-20 [PubMed:20599255]
[show Abstract]

Marchionatti AM, Picotto G, Narvaez CJ, Welsh J, Tolosa de Talamoni NG (2009)
Antiproliferative action of menadione and 1,25(OH)2D3 on breast cancer cells.
The Journal of steroid biochemistry and molecular biology 113, 227-232 [PubMed:19429426]
[show Abstract]

Pełczyńska K, Jaroszewicz I, Switalska M, Opolski A (2005)
[Biological activity of calcitriol and its new analogues -- potential therapeutic applications].
Postepy higieny i medycyny doswiadczalnej (Online) 59, 129-139 [PubMed:15928596]
[show Abstract]

Kriesel JD, Spruance J (1999)
Calcitriol (1,25-dihydroxy-vitamin D3) coadministered with influenza vaccine does not enhance humoral immunity in human volunteers.
Vaccine 17, 1883-1888 [PubMed:10217585]
[show Abstract]

Perry HM, Chappel JC, Clevinger BL, Haddad JG, Teitelbaum SL (1983)
Monoclonal antibody with high affinity for 1,25-dihydroxycholecalciferol.
Biochemical and biophysical research communications 112, 431-436 [PubMed:6687801]
[show Abstract]

Last Modified

04 August 2021

ChEBI

CHEBI:17823 - calcitriol

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