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CHEBI:66028 - 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione

ChEBI IDCHEBI:66028
ChEBI Name5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione
Stars
ASCII Name5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione
DefinitionA naphthofuran that is naphtho[2,3-b]furan-4,9-dione substituted by a hydroxy group at position 5 and a 1-hydroxyethyl group at position 2 (the S stereoisomer). Isolated from Tabebuia impetiginosa and Tabebuia avellanedae, it exhibits antineoplastic activity.
Last Modified3 June 2016
DownloadsMolfile
FormulaC14H10O5
Net Charge0
Average Mass258.229
Monoisotopic Mass258.05282
SMILESC[C@H](O)c1cc2c(o1)C(=O)c1cccc(O)c1C2=O
InChIInChI=1S/C14H10O5/c1-6(15)10-5-8-12(17)11-7(3-2-4-9(11)16)13(18)14(8)19-10/h2-6,15-16H,1H3/t6-/m0/s1
InChIKeyXJGFVZBTNKODFQ-LURJTMIESA-N
Species of MetaboliteComponentSourceComments
Tabebuia incana (IPNI:248702-2) bark (BTO:0001301) DOI (10.1590/S0044-59672007000100011) Nonseperated mixture of 5- and 8-hydroxy regioisomers
Tabebuia avellanedae (IPNI:110853-1) bark (BTO:0001301) PubMed (17950604) (S)-stereoisomer
Tabebuia ochracea ssp neochrysantha (ncbitaxon:429707) stem (BTO:0001300) DOI (10.1076/phbi.35.4.227.13306) Nonseperated mixture of 5- and 8-hydroxy regioisomers
Tabebuia impetiginosa (ncbitaxon:429701) - DOI (10.1039/P19910002323) Mixture of 5- and 8-hydroxy regioisomers
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)
5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione (CHEBI:66028) has role antineoplastic agent (CHEBI:35610)
5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione (CHEBI:66028) has role metabolite (CHEBI:25212)
5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione (CHEBI:66028) is a p-quinones (CHEBI:25830)
5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione (CHEBI:66028) is a naphthofuran (CHEBI:39270)
5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione (CHEBI:66028) is a phenols (CHEBI:33853)
5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione (CHEBI:66028) is a secondary alcohol (CHEBI:35681)
IUPAC Name 
5-hydroxy-2-[(1S)-1-hydroxyethyl]naphtho[2,3-b]furan-4,9-dione
Synonyms  Source
5-hydroxy-2-(1-hydroxyethyl)benzo[f][1]benzofuran-4,9-dioneChEBI
(−)-5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dioneChEBI
Registry NumbersSources
Reaxys:5381025Reaxys
CAS:123297-90-5ChemIDplus
Citations