NPASS Natural Product

Natural Product: NPC25270

Natural Product ID:	NPC25270
Common Name:	Cirsiliol
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one
Synonyms:	Cirsiliol
Molecular Formula:	C17H14O7
Standard InCHIKey:	IMEYGBIXGJLUIS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3
Canonical SMILES:	COc1cc2oc(cc(=O)c2c(c1OC)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	Isolation Part	Reference
NPO10051	Phyla nodiflora	Species	Verbenaceae	Eukaryota	Aerial parts	PMID[25140335]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota		TM-MC*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota		HerDing*
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota		TCMID*
NPO11100	Artemisia capillaris	Species	Asteraceae	Eukaryota		TM-MC*
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota		UNPD*
NPO14027	Dacryodes normandii	Species	Burseraceae	Eukaryota		UNPD*
NPO14039	Leucaena leucocephala	Species	Fabaceae	Eukaryota		UNPD*
NPO14201	Riccia fluitans	Species	Ricciaceae	Eukaryota		UNPD*
NPO14775	Penicillium javanicum	Species	Aspergillaceae	Eukaryota		UNPD*

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Biological Activity

Activity Type	# Activity
IC50	4
Ki	2
Others	6

Activity Type	# Activity
Cell Line	5
Individual Protein	6
Organism	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	0.5	%	3379415
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IZ	=	10.3	mm	25524452
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Ki	>	800	nM	21482471
NPT1603	Individual Protein	Cytochrome P450 1A1	Homo sapiens	Activity	=	16.7	%	21482471
NPT1604	Individual Protein	Cytochrome P450 1B1	Homo sapiens	Ki	>	800	nM	21482471
NPT183	Individual Protein	Arachidonate 5-lipoxygenase	Rattus norvegicus	IC50	=	95	nM	3783588
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	=	169.82	nM	18585047
NPT784	Cell Line	MDA-MB-468	Homo sapiens	Ratio IC50	=	8		21482471
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	8000	nM	19601638
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15000	nM	19601638

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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 NPC25270 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	318
0.1-0.2	1295
0.2-0.3	3014
0.3-0.4	7108
0.4-0.5	5632
0.5-0.6	2372
0.6-0.7	3515
0.7-0.8	4020
0.8-0.85	1757
0.85-0.9	1122
0.9-0.95	508
0.95-1	228

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Similarity Score	Similarity Level	Natural Product ID
0.9533	High Similarity	NPC191146
0.9533	High Similarity	NPC100916
0.9533	High Similarity	NPC55619
0.9533	High Similarity	NPC200388
0.9533	High Similarity	NPC268161

Showing 1 to 5 of 200 entries

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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 NPC25270 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	343
0.1-0.2	898
0.2-0.3	1707
0.3-0.4	2679
0.4-0.5	1791
0.5-0.6	1058
0.6-0.7	494
0.7-0.8	135
0.8-0.85	33
0.85-0.9	17
0.9-0.95	5
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6962	Remote Similarity	NPD1296	Phase 2
0.697	Remote Similarity	NPD2354	Approved
0.6977	Remote Similarity	NPD2296	Approved
0.698	Remote Similarity	NPD9493	Approved
0.6981	Remote Similarity	NPD1558	Phase 1

Showing 1 to 5 of 200 entries

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Structure

CID25270 OpenBabel06191715352D 24 26 0 0 0 0 0 0 0 0999 V2000 -0.8660 2.5000 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 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 2.5000 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 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 3.0000 0.0000 O 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 -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 4 2 0 0 0 0 3 8 1 0 0 0 0 4 9 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 6 12 2 0 0 0 0 7 13 2 0 0 0 0 7 14 1 0 0 0 0 8 12 1 0 0 0 0 9 10 2 0 0 0 0 9 18 1 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 11 20 2 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 17 2 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	160237
ChEMBL	CHEMBL72637
ZINC

Physicochemical Properties

Molecular Weight:	330.07
ALogP:	-1.9881
MLogP:	2.56
XLogP:	1.108
# Rotatable Bonds:	8
Polar Surface Area:	105.45
# H-Bond Aceptor:	1
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	24

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