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CHEBI:28940 - calciol

ChEBI IDCHEBI:28940
ChEBI Namecalciol
Stars
DefinitionA hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone.
Secondary ChEBI IDsCHEBI:10008, CHEBI:23170, CHEBI:46283
Last Modified28 October 2021
DownloadsMolfile
FormulaC27H44O
Net Charge0
Average Mass384.648
Monoisotopic Mass384.33922
SMILES[H][C@@]12CC[C@]([H])([C@H](C)CCCC(C)C)[C@@]1(C)CCC/C2=C\C=C1\C[C@@H](O)CCC1=C
InChIInChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1
InChIKeyQYSXJUFSXHHAJI-YRZJJWOYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - DOI (10.1038/nbt.2488)
Roles Classification
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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 (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.
Application:
geroprotector  Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
ChEBI Ontology
Outgoing Relation(s)
calciol (CHEBI:28940) has role geroprotector (CHEBI:176497)
calciol (CHEBI:28940) has role human metabolite (CHEBI:77746)
calciol (CHEBI:28940) is a D3 vitamins (CHEBI:73558)
calciol (CHEBI:28940) is a hydroxy seco-steroid (CHEBI:36853)
calciol (CHEBI:28940) is a seco-cholestane (CHEBI:36818)
calciol (CHEBI:28940) is a secondary alcohol (CHEBI:35681)
calciol (CHEBI:28940) is a steroid hormone (CHEBI:26764)
Incoming Relation(s)
(24R)-1α,24-dihydroxy-22-oxavitamin D3 (CHEBI:73923) has functional parent calciol (CHEBI:28940)
1α,23(S),25-trihydroxyvitamin D3 (CHEBI:90970) has functional parent calciol (CHEBI:28940)
1α,2β,25-trihydroxy vitamin D3 (CHEBI:87395) has functional parent calciol (CHEBI:28940)
5,6-trans-vitamin D3 (CHEBI:145213) has functional parent calciol (CHEBI:28940)
alfacalcidol (CHEBI:31186) has functional parent calciol (CHEBI:28940)
hydroxycalciol (CHEBI:47042) has functional parent calciol (CHEBI:28940)
oxocalciol (CHEBI:47806) has functional parent calciol (CHEBI:28940)
tacalcitol (CHEBI:32176) has functional parent calciol (CHEBI:28940)
IUPAC Name 
(3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol
Synonyms  Source
(1S,3Z)-3-[(2E)-2-[(1R,3AR,7AS)-7A-METHYL-1-[(2R)-6-METHYLHEPTAN-2-YL]-2,3,3A,5,6,7-HEXAHYDRO-1H-INDEN-4-YLIDENE]ETHYLIDENE]-4-METHYLIDENE-CYCLOHEXAN-1-OLPDBeChem
(3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-olNIST Chemistry WebBook
(5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-olJCBN
activated 7-dehydrocholesterolChemIDplus
calciolJCBN
CCChemIDplus
Brand Name  Source
Delta-DKEGG DRUG
UniProt Name  Source
calciolUniProt
Manual XrefsDatabases
160PPDB
2840DrugCentral
C05443KEGG COMPOUND
C05443KEGG COMPOUND
CholecalciferolWikipedia
D00188KEGG DRUG
DB00169DrugBank
HMDB0000876HMDB
LMST03020000LIPID MAPS
LMST03020001LIPID MAPS
VD3PDBeChem
Registry NumbersSources
Gmelin:1267613Gmelin
Reaxys:2339331Reaxys
CAS:67-97-0KEGG COMPOUND
CAS:67-97-0ChemIDplus
CAS:67-97-0NIST Chemistry WebBook
Citations