CHEBI:28940 - calciol

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ChEBI Name calciol
ChEBI ID CHEBI:28940
Definition A hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group.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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46283, CHEBI:10008, CHEBI:23170
Supplier Information ChemicalBook:CB6104867, ChemicalBook:CB15477624, ChemicalBook:CB6889016, ChemicalBook:CB01235577, eMolecules:17498063, eMolecules:25692852, Selleckchem:vitamin-d3-cholecalciferol, ZINC000004474460
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Formula C27H44O
Net Charge 0
Average Mass 384.63766
Monoisotopic Mass 384.33922
InChI InChI=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
InChIKey QYSXJUFSXHHAJI-YRZJJWOYSA-N
SMILES [H][C@@]1(CC[C@]2([H])[C@]1(C)CCC\C2=C/C=C1/C[C@@H](O)CCC1=C)[C@H](C)CCCC(C)C
Metabolite of Species Details
Homo sapiens (NCBI:txid9606) See: DOI
Roles Classification
Biological Role(s): human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
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 )
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.
(via steroid hormone )
Application(s): geroprotector
Any compound that supports healthy aging, slows the biological aging process, or extends lifespan.
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ChEBI Ontology
Outgoing 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 (24R)-1α,24-dihydroxy-22-oxavitamin D3 (CHEBI:73923) has functional parent calciol (CHEBI:28940)
1α,2β,25-trihydroxy vitamin D3 (CHEBI:87395) has functional parent calciol (CHEBI:28940)
1α,23(S),25-trihydroxyvitamin D3 (CHEBI:90970) 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 Sources
(+)-vitamin D3 NIST Chemistry WebBook
(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-OL PDBeChem
(3β,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol NIST Chemistry WebBook
(5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-ol JCBN
activated 7-dehydrocholesterol ChemIDplus
calciol UniProt
calciol JCBN
CC ChemIDplus
Cholecalciferol KEGG COMPOUND
colecalciferol ChemIDplus
oleovitamin D3 NIST Chemistry WebBook
Vitamin D3 KEGG COMPOUND
vitamin D3 ChEBI
Vitamin D3 LIPID MAPS
Brand Name Source
Delta-D KEGG DRUG
Manual Xrefs Databases
160 PPDB
2840 DrugCentral
C05443 KEGG COMPOUND
Cholecalciferol Wikipedia
D00188 KEGG DRUG
DB00169 DrugBank
HMDB0000876 HMDB
LMST03020000 LIPID MAPS
LMST03020001 LIPID MAPS
VD3 PDBeChem
View more database links
Registry Numbers Types Sources
1267613 Gmelin Registry Number Gmelin
2339331 Reaxys Registry Number Reaxys
67-97-0 CAS Registry Number KEGG COMPOUND
67-97-0 CAS Registry Number ChemIDplus
67-97-0 CAS Registry Number NIST Chemistry WebBook
Citations Waiting for Citations
Last Modified
28 October 2021