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

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03. Biological Effects of Specific Chemicals: biochemical uses [CHEBI:52206] > metabolite [CHEBI:25212] > secondary metabolite [CHEBI:26619] > 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028]
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03. Biological Effects of Specific Chemicals 
03. Biological Effects of Specific Chemicals
 biochemical uses [CHEBI:52206] (3306) 
 metabolite [CHEBI:25212] (2692) 
 secondary metabolite [CHEBI:26619] (2225) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
05. Industrial Uses 
05. Industrial Uses
 pharmaceutical [CHEBI:52217] (1978) 
 drug [CHEBI:23888] (1930) 
 antineoplastic agent [CHEBI:35610] (760) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
06. Name of Biological Source of Chemical 
06. Name of Biological Source of Chemical
 Plantae (1926) 
 Magnoliophyta (1872) 
 Magnoliopsida (1649) 
 Lamiales (196) 
 Bignoniaceae (2) 
 Tabebuia (2) 
 Tabebuia impetiginosa (2)
07. Part of Biological Source of Chemical 
07. Part of Biological Source of Chemical
 unspecified structure [PO:0000004] (703)
08. Chemical Category 
08. Chemical Category
 main group molecular entity [CHEBI:33579] (25650) 
 s-block molecular entity [CHEBI:33674] (7287) 
 hydrogen molecular entity [CHEBI:33608] (6932) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 secondary alcohol [CHEBI:35681] (342) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 phenols [CHEBI:33853] (868) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 p-block molecular entity [CHEBI:33675] (25343) 
 chalcogen molecular entity [CHEBI:33304] (15225) 
 oxygen molecular entity [CHEBI:25806] (14414) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 secondary alcohol [CHEBI:35681] (342) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 phenols [CHEBI:33853] (868) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 oxacycle [CHEBI:38104] (2002) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 oxacycle [CHEBI:38104] (2002) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 carbon group molecular entity [CHEBI:33582] (23847) 
 organic molecular entity [CHEBI:50860] (23769) 
 heteroorganic entity [CHEBI:33285] (15197) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organochalcogen compound [CHEBI:36962] (11874) 
 organooxygen compound [CHEBI:36963] (11352) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 oxacycle [CHEBI:38104] (2002) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 secondary alcohol [CHEBI:35681] (342) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 phenols [CHEBI:33853] (868) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 quinone [CHEBI:36141] (209) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic polycyclic compound [CHEBI:51958] (1654) 
 organic tricyclic compound [CHEBI:51959] (755) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 polyatomic entity [CHEBI:36357] (18777) 
 molecule [CHEBI:25367] (11520) 
 cyclic compound [CHEBI:33595] (7817) 
 polycyclic compound [CHEBI:33635] (4078) 
 heteropolycyclic compound [CHEBI:33671] (2613) 
 heterotricyclic compound [CHEBI:36688] (541) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic polycyclic compound [CHEBI:51958] (1654) 
 organic tricyclic compound [CHEBI:51959] (755) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 aromatic compound [CHEBI:33655] (3799) 
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic polycyclic compound [CHEBI:51958] (1654) 
 organic tricyclic compound [CHEBI:51959] (755) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 heterocyclic compound [CHEBI:5686] (5275) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 heteropolycyclic compound [CHEBI:33671] (2613) 
 heterotricyclic compound [CHEBI:36688] (541) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic molecule [CHEBI:72695] (11399) 
 organic cyclic compound [CHEBI:33832] (7633) 
 organic heterocyclic compound [CHEBI:24532] (5243) 
 oxacycle [CHEBI:38104] (2002) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic heteropolycyclic compound [CHEBI:38166] (2613) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic aromatic compound [CHEBI:33659] (3593) 
 phenols [CHEBI:33853] (868) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic polycyclic compound [CHEBI:51958] (1654) 
 organic tricyclic compound [CHEBI:51959] (755) 
 organic heterotricyclic compound [CHEBI:26979] (541) 
 naphthofuran [CHEBI:39270] (11) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 organic oxo compound [CHEBI:36587] (5932) 
 carbonyl compound [CHEBI:36586] (5928) 
 ketone [CHEBI:17087] (1288) 
 cyclic ketone [CHEBI:3992] (644) 
 quinone [CHEBI:36141] (209) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 heteroatomic molecular entity [CHEBI:37577] (13672) 
 hydroxides [CHEBI:24651] (5641) 
 organic hydroxy compound [CHEBI:33822] (3050) 
 alcohol [CHEBI:30879] (1371) 
 secondary alcohol [CHEBI:35681] (342) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
 phenols [CHEBI:33853] (868) 
 5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione [CHEBI:66028] (1)
ChEBI Compound Accession Identifier:   [CHEBI:66028]
ChEBI Compound Description:   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.
ChEBI Compound Identification Number:   66028
ChEBI InChI Value:   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
ChEBI InChIKey Value:   XJGFVZBTNKODFQ-LURJTMIESA-N
ChEBI Compound Name:   5-hydroxy-2-(1'-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione
ChEBI SMILES Value:   C[C@H](O)c1cc2C(=O)c3c(O)cccc3C(=O)c2o1
ChEBI Substance ID:   160709703
ChEBI URL:   ChEBI:66028
ChemSpider ID:   19985759
Ontomatica Chemical Accession Key (OnChAKey):   XJGFVZBTNKODFQ_LURJTMIESA_N_000_000000
PubChem Compound ID:   14159819