CHEBI:66044 - trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid
ChEBI ID CHEBI:66044
ChEBI ASCII Name trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid
Definition A member of the class of 1-benzofurans that is 2,3-dihydro-1-benzofuran substituted by a hydroxy group at position 3, a hydroxyisopropyl group at position 2, a carboxy group at position 5 and a prenyl group at position 7 (the 2S,3S stereoisomer) . Isolated from the rhizomes of Atractylodes lancea, it exhibits cytotoxicity against cancer cell lines HCT-116 and MKN-45.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C17H22O5
Net Charge 0
Average Mass 306.35360
Monoisotopic Mass 306.14672
InChI InChI=1S/C17H22O5/c1-9(2)5-6-10-7-11(16(19)20)8-12-13(18)15(17(3,4)21)22-14(10)12/h5,7-8,13,15,18,21H,6H2,1-4H3,(H,19,20)/t13-,15-/m0/s1
InChIKey AYTRSZSGVDVZHC-ZFWWWQNUSA-N
SMILES CC(C)=CCc1cc(cc2[C@H](O)[C@H](Oc12)C(C)(C)O)C(O)=O
Metabolite of Species Details
Atractylodes lancea (NCBI:txid69406) Found in rhizome (BTO:0001181). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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 trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid (CHEBI:66044) has role antineoplastic agent (CHEBI:35610)
trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid (CHEBI:66044) has role metabolite (CHEBI:25212)
trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid (CHEBI:66044) is a 1-benzofurans (CHEBI:38830)
trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid (CHEBI:66044) is a hydroxy monocarboxylic acid (CHEBI:35868)
trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid (CHEBI:66044) is a secondary alcohol (CHEBI:35681)
trans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid (CHEBI:66044) is a tertiary alcohol (CHEBI:26878)
IUPAC Name
(2S,3S)-3-hydroxy-2-(2-hydroxypropan-2-yl)-7-(3-methylbut-2-en-1-yl)-2,3-dihydro-1-benzofuran-5-carboxylic acid
Citation Waiting for Citations Type Source
18787781 PubMed citation Europe PMC
Last Modified
26 February 2013