CHEBI:65568 - calotropone

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ChEBI Name calotropone
ChEBI ID CHEBI:65568
Definition A 20-oxo steroid that is 17α-pregn-5-en-20-one substituted by a benzoyloxy group at position 12 and hydroxy groups at positions 3, 14 and 17 (the 3β,12β,14β stereoisomer). It is isolated from the roots of Calotropis gigantea and displays inhibitory effects towards chronic myelogenous leukemia K562 and human gastric cancer SGC-7901 cell lines.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C28H36O6
Net Charge 0
Average Mass 468.58180
Monoisotopic Mass 468.25119
InChI InChI=1S/C28H36O6/c1-17(29)27(32)13-14-28(33)21-10-9-19-15-20(30)11-12-25(19,2)22(21)16-23(26(27,28)3)34-24(31)18-7-5-4-6-8-18/h4-9,20-23,30,32-33H,10-16H2,1-3H3/t20-,21+,22-,23+,25-,26+,27+,28-/m0/s1
InChIKey LFDIXHMYXFFMFD-QQYZDZQSSA-N
SMILES [H][C@]12C[C@@H](OC(=O)c3ccccc3)[C@]3(C)[C@@](O)(CC[C@]3(O)[C@]1([H])CC=C1C[C@@H](O)CC[C@]21C)C(C)=O
Metabolite of Species Details
Calotropis gigantea (NCBI:txid4066) Found in root (BTO:0001188). See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing calotropone (CHEBI:65568) has parent hydride pregnane (CHEBI:8386)
calotropone (CHEBI:65568) has role antineoplastic agent (CHEBI:35610)
calotropone (CHEBI:65568) has role metabolite (CHEBI:25212)
calotropone (CHEBI:65568) is a 14β-hydroxy steroid (CHEBI:36862)
calotropone (CHEBI:65568) is a 17β-hydroxy steroid (CHEBI:35343)
calotropone (CHEBI:65568) is a 20-oxo steroid (CHEBI:36885)
calotropone (CHEBI:65568) is a 3β-hydroxy-Δ5-steroid (CHEBI:1722)
calotropone (CHEBI:65568) is a benzoate ester (CHEBI:36054)
calotropone (CHEBI:65568) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name
3β,14β,17-trihydroxy-20-oxo-17α-pregn-5-en-12β-yl benzoate
Synonyms Sources
(3β,12β,14β,17α)-3,14,17-trihydroxy-20-oxopregn-5-en-12-yl benzoate IUPAC
12β-benzoyloxy-3β,14β,17β-trihydroxypregnane-20-one ChEBI
12β-O-benzoyl-3β,14β,17β-trihydroxypregnane-20-one
Note: (2012-12-04) The synonym is a misnomer. The name does not include the oxygen atom at position 12 to which the benzoyl group is attached. It should be 12β-benzoyloxy-3β,14β,17β-trihydroxypregnane-20-one.
 ChEBI
Registry Number Type Source
18872733 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
19052526 PubMed citation Europe PMC
Last Modified
07 February 2018