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calciol

Go to external page http://purl.obolibrary.org/obo/CHEBI_28940

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hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group.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.

Term info

Label

calciol

Synonyms
  • (3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol
  • calciol
database cross reference
Subsets

3_STAR

IUPAC NAME
(3S,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol [ IUPAC ]

BRAND NAME
Delta-D [ KEGG_DRUG ]

charge

0

formula

C27H44O

has alternative id

CHEBI:46283, CHEBI:23170, CHEBI:10008

has obo namespace

chebi_ontology

has related synonym

CC, Vitamin D3, (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, Cholecalciferol, colecalciferol, Delta-D, vitamin D3, (3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-trien-3-ol, activated 7-dehydrocholesterol, (5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-ol, oleovitamin D3, (+)-vitamin D3

id

CHEBI:28940

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

mass

384.63766

monoisotopicmass

384.33922

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