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CHEBI:139026 - AMCR277A

ChEBI IDCHEBI:139026
ChEBI NameAMCR277A
Stars
DefinitionA hydroxycalciol that is calcitriol which has undergone formal oxidative coupling at positions 20 and 23 to the hydroxy group and methyl group, respectively, of methanol to afford the corresponding oxolane ring (the 20S,23S stereoisomer). It is a superagonist of the vitamin D nuclear receptor in vitro, but is as calcemic in vivo as the natural ligand.
Last Modified16 November 2017
SubmitterCeri
DownloadsMolfile
FormulaC28H44O4
Net Charge0
Average Mass444.656
Monoisotopic Mass444.32396
SMILES[H][C@]1([C@]2(C)C[C@H](CC(C)(C)O)CO2)CC[C@@]2([H])/C(=C/C=C3/C[C@@H](O)C[C@H](O)C3=C)CCC[C@]12C
InChIInChI=1S/C28H44O4/c1-18-21(13-22(29)14-24(18)30)9-8-20-7-6-12-27(4)23(20)10-11-25(27)28(5)16-19(17-32-28)15-26(2,3)31/h8-9,19,22-25,29-31H,1,6-7,10-17H2,2-5H3/b20-8+,21-9-/t19-,22+,23-,24-,25-,27-,28-/m0/s1
InChIKeyQFEREDUWILIRPI-VCQGKADLSA-N
Roles Classification
Biological Role:
agonist  Substance which binds to cell receptors normally responding to naturally occurring substances and which produces a response of its own.
ChEBI Ontology
Outgoing Relation(s)
AMCR277A (CHEBI:139026) has functional parent calcitriol (CHEBI:17823)
AMCR277A (CHEBI:139026) has role agonist (CHEBI:48705)
AMCR277A (CHEBI:139026) is a hydroxycalciol (CHEBI:47042)
AMCR277A (CHEBI:139026) is a oxolanes (CHEBI:26912)
IUPAC Name 
(1S,3R,5Z,7E,23S)-23-(2-hydroxy-2-methylpropyl)-20,24-epoxy-9,10-secochola-5,7,10-triene-1,3-diol
Registry NumbersSources
Reaxys:12849620Reaxys
Citations