CHEBI:139026 - AMCR277A

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ChEBI Name AMCR277A
ChEBI ID CHEBI:139026
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Ceri
Supplier Information
Download Molfile XML SDF
Formula C28H44O4
Net Charge 0
Average Mass 444.648
Monoisotopic Mass 444.32396
InChI InChI=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
InChIKey QFEREDUWILIRPI-VCQGKADLSA-N
SMILES C\1([C@H](C[C@@H](C/C1=C/C=C/2\CCC[C@]3([C@]2(CC[C@@]3([C@]4(C)C[C@@H](CO4)CC(O)(C)C)[H])[H])C)O)O)=C
Roles Classification
Biological Role(s): agonist
Substance which binds to cell receptors normally responding to naturally occurring substances and which produces a response of its own.
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ChEBI Ontology
Outgoing 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 Number Type Source
12849620 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
18420145 PubMed citation Europe PMC
20070104 PubMed citation Europe PMC
24936188 PubMed citation Europe PMC
Last Modified
16 November 2017