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5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone
An extended flavonoid that consists of (2S)-flavanone substituted by hydroxy groups at positions 5, 7 and 3', prenyl groups at positions 8 and 2' and a gem-dimethyl pyran ring fused across positions 4' and 5'. Isolated from Dendrolobium lanceolatum, it exhibits antimalarial activity.

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03. Biological Effects of Specific Chemicals

			biochemical uses [CHEBI:52206] (3306)

					metabolite [CHEBI:25212] (2692)

						secondary metabolite [CHEBI:26619] (2225)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

			antimicrobial agent [CHEBI:33281] (927)

				antimicrobial drug [CHEBI:36043] (169)

					antiprotozoal drug [CHEBI:35820] (168)

						antimalarial [CHEBI:38068] (89)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

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)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (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)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

organooxygen compound [CHEBI:36963] (11352)

carbonyl compound [CHEBI:36586] (5928)

ketone [CHEBI:17087] (1288)

cyclic ketone [CHEBI:3992] (644)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

oxacycle [CHEBI:38104] (2002)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

flavonoids [CHEBI:72544] (433)

flavonoid [CHEBI:47916] (301)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

extended flavonoid [CHEBI:71037] (20)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (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)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

oxacycle [CHEBI:38104] (2002)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (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)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (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)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

oxacycle [CHEBI:38104] (2002)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

								organic hydroxy compound [CHEBI:33822] (3050)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

								flavonoids [CHEBI:72544] (433)

flavonoid [CHEBI:47916] (301)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

extended flavonoid [CHEBI:71037] (20)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

								organic molecule [CHEBI:72695] (11399)

									organic cyclic compound [CHEBI:33832] (7633)

organic heterocyclic compound [CHEBI:24532] (5243)

oxacycle [CHEBI:38104] (2002)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

organic aromatic compound [CHEBI:33659] (3593)

phenylpropanoid [CHEBI:26004] (374)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

									organic oxo compound [CHEBI:36587] (5932)

carbonyl compound [CHEBI:36586] (5928)

ketone [CHEBI:17087] (1288)

cyclic ketone [CHEBI:3992] (644)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (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)

organic heteropolycyclic compound [CHEBI:38166] (2613)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

								aromatic compound [CHEBI:33655] (3799)

organic aromatic compound [CHEBI:33659] (3593)

phenylpropanoid [CHEBI:26004] (374)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

								organic cyclic compound [CHEBI:33832] (7633)

organic heterocyclic compound [CHEBI:24532] (5243)

oxacycle [CHEBI:38104] (2002)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

organic aromatic compound [CHEBI:33659] (3593)

phenylpropanoid [CHEBI:26004] (374)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

								heterocyclic compound [CHEBI:5686] (5275)

									organic heterocyclic compound [CHEBI:24532] (5243)

oxacycle [CHEBI:38104] (2002)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

									heteropolycyclic compound [CHEBI:33671] (2613)

organic heteropolycyclic compound [CHEBI:38166] (2613)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

						organic molecule [CHEBI:72695] (11399)

							organic cyclic compound [CHEBI:33832] (7633)

									organic heterocyclic compound [CHEBI:24532] (5243)

oxacycle [CHEBI:38104] (2002)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

organic heteropolycyclic compound [CHEBI:38166] (2613)

benzopyran [CHEBI:22727] (349)

1-benzopyran [CHEBI:38443] (328)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

									organic aromatic compound [CHEBI:33659] (3593)

phenylpropanoid [CHEBI:26004] (374)

flavans [CHEBI:38672] (124)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

							organic oxo compound [CHEBI:36587] (5932)

								carbonyl compound [CHEBI:36586] (5928)

									ketone [CHEBI:17087] (1288)

cyclic ketone [CHEBI:3992] (644)

flavanones [CHEBI:28863] (98)

hydroxyflavanone [CHEBI:24697] (90)

trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

				heteroatomic molecular entity [CHEBI:37577] (13672)

					hydroxides [CHEBI:24651] (5641)

						organic hydroxy compound [CHEBI:33822] (3050)

							hydroxyflavanone [CHEBI:24697] (90)

								trihydroxyflavanone [CHEBI:38739] (28)

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone [CHEBI:66267] (1)

ChEBI Compound Accession Identifier:

[CHEBI:66267]

ChEBI Compound Description:

An extended flavonoid that consists of (2S)-flavanone substituted by hydroxy groups at positions 5, 7 and 3', prenyl groups at positions 8 and 2' and a gem-dimethyl pyran ring fused across positions 4' and 5'. Isolated from Dendrolobium lanceolatum, it exhibits antimalarial activity.

ChEBI Compound Identification Number:

66267

ChEBI InChI Value:

InChI=1S/C30H34O6/c1-16(2)7-9-19-21(13-18-11-12-30(5,6)36-28(18)27(19)34)25-15-24(33)26-23(32)14-22(31)20(29(26)35-25)10-8-17(3)4/h7-8,11-14,25,31-32,34H,9-10,15H2,1-6H3/t25-/m0/s1

ChEBI InChIKey Value:

WHMJSNMIIPVCHC-VWLOTQADSA-N

ChEBI Compound Name:

5,7,3'-trihydroxy-4',5'-(2'''',2''''-dimethylpyran)-8,2'-di(3-methyl-2-butenyl)-(2S)-flavanone

ChEBI SMILES Value:

CC(C)=CCc1c(O)c2OC(C)(C)C=Cc2cc1[C@@H]1CC(=O)c2c(O)cc(O)c(CC=C(C)C)c2O1

ChEBI Substance ID:

160709815

ChEBI URL:

ChEBI:66267

ChemSpider ID:

2281395

Ontomatica Chemical Accession Key (OnChAKey):

WHMJSNMIIPVCHC_VWLOTQADSA_N_000_000000

PubChem Compound ID:

3012485