calotropone (CHEBI:65568)

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CHEBI:65568 - calotropone

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ChEBI ID	CHEBI:65568
ChEBI Name	calotropone
Stars
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.
Last Modified	7 February 2018
Downloads	Molfile

Formula	C28H36O6
Net Charge	0
Average Mass	468.590
Monoisotopic Mass	468.25119
SMILES	[H][C@]12C[C@@H](OC(=O)c3ccccc3)[C@@]3(C)[C@](O)(CC[C@@]3(O)C(C)=O)[C@]1([H])CC=C1C[C@@H](O)CC[C@@]12C
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

Species of Metabolite	Component	Source	Comments
Calotropis gigantea (ncbitaxon:4066)	root (BTO:0001188)	PubMed (19052526)

Roles Classification

Biological Role:	metabolite Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology

Outgoing Relation(s)
	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	Source
12β-benzoyloxy-3β,14β,17β-trihydroxypregnane-20-one	ChEBI
12β-O-benzoyl-3β,14β,17β-trihydroxypregnane-20-one	ChEBI
(3β,12β,14β,17α)-3,14,17-trihydroxy-20-oxopregn-5-en-12-yl benzoate	IUPAC

Registry Numbers	Sources
Reaxys:18872733	Reaxys

Citations