CHEBI:48530 - fumagalone

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ChEBI Name fumagalone
ChEBI ID CHEBI:48530
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C16H24O5
Net Charge 0
Average Mass 296.35876
Monoisotopic Mass 296.16237
InChI InChI=1S/C16H24O5/c1-10(2)5-6-12-15(3,21-12)14-13(20-4)11(18)7-8-16(14,19)9-17/h5,9,12-14,19H,6-8H2,1-4H3/t12-,13-,14-,15+,16+/m1/s1
InChIKey UKNNCBXEELDDCU-SUJAAXHWSA-N
SMILES [H]C(=O)[C@@]1(O)CCC(=O)[C@@H](OC)[C@]1([H])[C@@]1(C)O[C@@H]1CC=C(C)C
ChEBI Ontology
Outgoing fumagalone (CHEBI:48530) has functional parent cyclohexanone (CHEBI:17854)
fumagalone (CHEBI:48530) is a aldehyde (CHEBI:17478)
fumagalone (CHEBI:48530) is a sesquiterpenoid (CHEBI:26658)
Incoming (1R,2S,3S,4S)-4-formyl-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]cyclohexyl (2E)-3-(4-methoxyphenyl)acrylate (CHEBI:48414) has functional parent fumagalone (CHEBI:48530)
(1S,2S,3S)-3-methoxy-2-[(2E)-6-methylhept-2-en-2-yl]-4-oxocyclohexanecarbaldehyde (CHEBI:48411) has functional parent fumagalone (CHEBI:48530)
(2S,3S,4S)-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]-4-(trifluoroacetyl)cyclohexanone (CHEBI:48412) has functional parent fumagalone (CHEBI:48530)
(2S,3S,4S)-4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]cyclohexanone (CHEBI:48415) has functional parent fumagalone (CHEBI:48530)
(2S,3S,4S)-4-(hydroxymethyl)-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]cyclohexanone (CHEBI:48410) has functional parent fumagalone (CHEBI:48530)
(2S,3S,4S)-4-acetyl-2-methoxy-3-[(2E)-6-methylhept-2-en-2-yl]cyclohexanone (CHEBI:48413) has functional parent fumagalone (CHEBI:48530)
IUPAC Name
(1R,2S,3S)-1-hydroxy-3-methoxy-2-[(2R,3R)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-oxocyclohexanecarbaldehyde
Manual Xref Database
FR2872511 Patent
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Registry Number Type Source
9500651 Beilstein Registry Number Beilstein
Last Modified
17 October 2009
General Comment
2008-02-28 Zhou, G., Tsai, C.W. and Liu, J.O. (2003) Fumagalone, a reversible inhibitor of type 2 methionine aminopeptidase and angiogenesis. J. Med. Chem. 46, 3452-3454. [PMID:12877582]