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

ChEBI IDCHEBI:66044
ChEBI Nametrans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid
Stars
ASCII Nametrans-2-hydroxyisoxypropyl-3-hydroxy-7-isopentene-2,3-dihydrobenzofuran-5-carboxylic acid
DefinitionA 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.
Last Modified26 February 2013
DownloadsMolfile
FormulaC17H22O5
Net Charge0
Average Mass306.358
Monoisotopic Mass306.14672
SMILESCC(C)=CCc1cc(C(=O)O)cc2c1O[C@H](C(C)(C)O)[C@H]2O
InChIInChI=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
InChIKeyAYTRSZSGVDVZHC-ZFWWWQNUSA-N
Species of MetaboliteComponentSourceComments
Atractylodes lancea (ncbitaxon:69406) rhizome (BTO:0001181) PubMed (18787781)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
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)
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
Citations