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	ChemicalBook:CB6134417, eMolecules:532057, eMolecules:28206777, ZINC000000025672

Download	Molfile XML SDF

more structures >>

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21.7304 -13.5716 4.0077 C 0 0 2 0 0 0 0 0 0 0 0 0

20.5223 -12.6721 4.3614 C 0 0 0 0 0 0 0 0 0 0 0 0

22.5108 -13.7642 5.2417 C 0 0 0 0 0 0 0 0 0 0 0 0

18.1242 -24.6623 4.7927 O 0 0 0 0 0 0 0 0 0 0 0 0

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15.9351 -26.2824 4.7615 H 0 0 0 0 0 0 0 0 0 0 0 0

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16.8661 -17.5403 2.6758 H 0 0 0 0 0 0 0 0 0 0 0 0

18.6464 -17.3106 2.4116 H 0 0 0 0 0 0 0 0 0 0 0 0

17.9518 -18.9848 2.5136 H 0 0 0 0 0 0 0 0 0 0 0 0

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32 2 1 0 0 0 0

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M END): 67 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.

Default Van der Waals type for model set to Babel

74 atoms created

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

Script completed

Jmol script terminated

Molfile expand

Wikipedia	License
Thymidine (symbol dT or dThd), also known as deoxythymidine, deoxyribosylthymine, or thymine deoxyriboside, is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in G1/early S phase. The prefix deoxy- is often left out since there are no precursors of thymine nucleotides involved in RNA synthesis. Before the boom in thymidine use caused by the need for thymidine in the production of the antiretroviral drug azidothymidine (AZT), much of the world's thymidine production came from herring sperm. Thymidine occurs almost exclusively in DNA but it also occurs in the T-loop of tRNA.
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	Types	Sources
10217585	PubMed citation	Europe PMC
15928596	PubMed citation	Europe PMC
19429426	PubMed citation	Europe PMC
20599255	PubMed citation	Europe PMC
22905919	PubMed citation	Europe PMC
23103122	PubMed citation	Europe PMC
23144765	PubMed citation	Europe PMC
6687801	PubMed citation	Europe PMC

Last Modified

04 August 2021

CHEBI:17823 - calcitriol

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