NPASS Natural Product

Natural Product: NPC51443

Natural Product ID:	NPC51443
Common Name:	Fisetin
IUPAC Name:	2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one
Synonyms:	NSC-407010
Molecular Formula:	C15H10O6
Standard InCHIKey:	XHEFDIBZLJXQHF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H
Canonical SMILES:	Oc1ccc2c(c1)oc(c(c2=O)O)c1ccc(c(c1)O)O
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10026	Mitracarpus scaber	Species	Rubiaceae	Eukaryota	UNPD*
NPO10325	Boletus pini	Species	Boletaceae	Eukaryota	UNPD*
NPO11174	Hemsleya graciliflora	Species	Cucurbitaceae	Eukaryota	UNPD*
NPO12021	Artemisia incanescens	Species	Asteraceae	Eukaryota	UNPD*
NPO12213	Perriera orientalis	Species	Simaroubaceae	Eukaryota	UNPD*
NPO1245	Eunicella cavolinii	Species	Gorgoniidae	Eukaryota	UNPD*
NPO12564	Sinularia facile	Species	Alcyoniidae	Eukaryota	UNPD*
NPO12716	Stocksia brahuica	NA	NA	NA	UNPD*
NPO13600	Ichthyothere latifolia	Species	Asteraceae	Eukaryota	UNPD*
NPO13685	Scrophularia umbrosa	Species	Scrophulariaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
EC50	6
ED50	1
GI50	59
IC50	57
Ki	4
MIC	10
Others	61
Potency	59

Activity Type	# Activity
Cell Line	79
Individual Protein	88
Organism	25
Others	54
Protein Complex	6
Protein Family	1
Protein-Protein Interaction	4

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC25	=	7.9	nM	17166721
NPT1	Others	Radical scavenging activity		Inhibition	=	79	%	10.1007/s00044-007-9060-5
NPT1	Others	Radical scavenging activity		IC50	=	9.26	ug/ml	24727463
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	Activity	<	50	%	7769390
NPT1044	Individual Protein	DNA topoisomerase II alpha	Homo sapiens	IC50	=	8.2	ug/ml	7769390
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	25118.9	nM	PubChem BioAssay data set
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	39810.7	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	GI50		25003.45	nM	PubChem BioAssay data set
NPT111	Cell Line	K562	Homo sapiens	Activity	=	33.7	%	24727463
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	=	950	nM	17869117

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Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC51443 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	1398
0.2-0.3	3474
0.3-0.4	7629
0.4-0.5	4670
0.5-0.6	2521
0.6-0.7	3751
0.7-0.8	3970
0.8-0.85	1681
0.85-0.9	1032
0.9-0.95	384
0.95-1	39

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Similarity Score	Similarity Level	Natural Product ID
0.9205	High Similarity	NPC288669
0.9205	High Similarity	NPC204854
0.9205	High Similarity	NPC191459
0.9205	High Similarity	NPC193842
0.9205	High Similarity	NPC130894

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Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC51443 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	370
0.1-0.2	937
0.2-0.3	1742
0.3-0.4	2653
0.4-0.5	1766
0.5-0.6	1086
0.6-0.7	441
0.7-0.8	111
0.8-0.85	33
0.85-0.9	16
0.9-0.95	4
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6906	Remote Similarity	NPD8150	Discontinued
0.6909	Remote Similarity	NPD5049	Phase 3
0.6911	Remote Similarity	NPD7584	Approved
0.6919	Remote Similarity	NPD4361	Phase 2
0.6919	Remote Similarity	NPD4362	Clinical (unspecified phase)

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Structure

CID51443 OpenBabel06191715382D 21 23 0 0 0 0 0 0 0 0999 V2000 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 7 1 0 0 0 0 2 3 2 0 0 0 0 2 8 1 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 7 2 0 0 0 0 5 11 1 0 0 0 0 6 8 2 0 0 0 0 6 12 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 9 12 2 0 0 0 0 9 13 1 0 0 0 0 10 11 2 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 21 1 0 0 0 0 13 14 1 0 0 0 0 13 19 2 0 0 0 0 14 15 2 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5281614
ChEMBL	CHEMBL31574
ZINC

Physicochemical Properties

Molecular Weight:	286.05
ALogP:	-2.3409
MLogP:	2.45
XLogP:	2.344
# Rotatable Bonds:	5
Polar Surface Area:	107.22
# H-Bond Aceptor:	2
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	21

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