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

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ChEBI Name	5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione

ChEBI ID	CHEBI:66028

ChEBI ASCII Name	5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Supplier Information

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Formula

C14H10O5

Net Charge

Average Mass

258.22620

Monoisotopic Mass

258.05282

InChI

InChI=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

InChIKey

XJGFVZBTNKODFQ-LURJTMIESA-N

SMILES

C[C@H](O)c1cc2C(=O)c3c(O)cccc3C(=O)c2o1

Metabolite of Species	Details
Tabebuia avellanedae (IPNI:110853-1)	Found in bark (BTO:0001301). (S)-stereoisomer See: PubMed
Tabebuia incana (IPNI:248702-2)	Found in bark (BTO:0001301). Nonseperated mixture of 5- and 8-hydroxy regioisomers See: DOI
Tabebuia impetiginosa (NCBI:txid429701)	Mixture of 5- and 8-hydroxy regioisomers See: DOI
Tabebuia ochracea ssp neochrysantha (NCBI:txid429707)	Found in stem (BTO:0001300). Nonseperated mixture of 5- and 8-hydroxy regioisomers See: DOI

Roles Classification
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.

ChEBI Ontology
Outgoing	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	Sources
(−)-5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione	ChEBI
5-hydroxy-2-(1-hydroxyethyl)benzo[f][1]benzofuran-4,9-dione	ChEBI

Citation	Type	Source
17950604	PubMed citation	Europe PMC

Last Modified

03 June 2016