NPASS Natural Product

Natural Product: NPC160951

Natural Product ID:	NPC160951
Common Name:	Eupatorin
IUPAC Name:	5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-6,7-dimethoxychromen-4-one
Synonyms:	Eupatorin
Molecular Formula:	C18H16O7
Standard InCHIKey:	KLAOKWJLUQKWIF-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O7/c1-22-12-5-4-9(6-10(12)19)13-7-11(20)16-14(25-13)8-15(23-2)18(24-3)17(16)21/h4-8,19,21H,1-3H3
Canonical SMILES:	COc1cc2oc(cc(=O)c2c(c1OC)O)c1ccc(c(c1)O)OC
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO10073	Clusia torresii	Species	Clusiaceae	Eukaryota	UNPD*
NPO10353	Rauvolfia tetraphylla	Species	Apocynaceae	Eukaryota	UNPD*
NPO10412	Aglaia erythrosperma	Species	Meliaceae	Eukaryota	UNPD*
NPO10436	Aristolochia maxima	Species	Aristolochiaceae	Eukaryota	UNPD*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	TCMID*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	HerDing*
NPO10996	Ferula assa-foetida	Species	Apiaceae	Eukaryota	UNPD*
NPO11020	Streptomyces purpeofuscus	Species	Streptomycetaceae	Bacteria	UNPD*
NPO11112	Inulanthera nuda	Species	Asteraceae	Eukaryota	UNPD*
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
ED50	3
IC50	1
Ki	5
MIC	2
Others	7

Activity Type	# Activity
Cell Line	4
Individual Protein	8
Organism	4
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1432	Individual Protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	Ki	=	1000	nM	PubChem BioAssay data set
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	Ki	=	39.81	nM	PubChem BioAssay data set
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	Ki	=	794.33	nM	PubChem BioAssay data set
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Ki	=	210	nM	21482471
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Activity	=	47.8	%	21482471
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	Ki	=	35	nM	21482471
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	187.5	ug/ml	6512542
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	>	375	ug/ml	6512542
NPT2	Others	Unspecified		ED50	=	3.7	ug/ml	11374950
NPT2	Others	Unspecified		Activity	=	0		8882428

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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 NPC160951 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	301
0.1-0.2	1271
0.2-0.3	2790
0.3-0.4	6806
0.4-0.5	6124
0.5-0.6	2336
0.6-0.7	3453
0.7-0.8	4056
0.8-0.85	1762
0.85-0.9	1198
0.9-0.95	553
0.95-1	239

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Similarity Score	Similarity Level	Natural Product ID
0.9536	High Similarity	NPC241904
0.9536	High Similarity	NPC476981
0.9536	High Similarity	NPC469584
0.9536	High Similarity	NPC262286
0.9536	High Similarity	NPC36852

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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 NPC160951 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	885
0.2-0.3	1656
0.3-0.4	2653
0.4-0.5	1834
0.5-0.6	1082
0.6-0.7	529
0.7-0.8	139
0.8-0.85	32
0.85-0.9	15
0.9-0.95	6
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6979	Remote Similarity	NPD7697	Approved
0.6979	Remote Similarity	NPD7696	Phase 3
0.699	Remote Similarity	NPD7783	Phase 2
0.699	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1535	Discovery

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Structure

CID160951 OpenBabel06191715532D 25 27 0 0 0 0 0 0 0 0999 V2000 7.7942 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 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 6.0622 2.5000 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 5 2 0 0 0 0 4 9 1 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 13 1 0 0 0 0 10 12 2 0 0 0 0 10 19 1 0 0 0 0 11 16 1 0 0 0 0 11 20 2 0 0 0 0 12 22 1 0 0 0 0 13 25 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 18 2 0 0 0 0 15 23 1 0 0 0 0 16 17 2 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	97214
ChEMBL	CHEMBL487402
ZINC

Physicochemical Properties

Molecular Weight:	344.09
ALogP:	-1.5796
MLogP:	2.67
XLogP:	1.198
# Rotatable Bonds:	9
Polar Surface Area:	94.45
# H-Bond Aceptor:	1
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	25

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