NPASS Natural Product

Natural Product: NPC262286

Natural Product ID:	NPC262286
Common Name:	Cowaxanthone
IUPAC Name:	2-[(2E)-3,7-dimethylocta-2,6-dienyl]-1,3,6-trihydroxy-7-methoxyxanthen-9-one
Synonyms:	Cowaxanthone
Molecular Formula:	C24H26O6
Standard InCHIKey:	VEGUCVDYIMCIAZ-RIYZIHGNSA-N
Standard InCHI:	InChI=1S/C24H26O6/c1-13(2)6-5-7-14(3)8-9-15-17(25)11-21-22(23(15)27)24(28)16-10-20(29-4)18(26)12-19(16)30-21/h6,8,10-12,25-27H,5,7,9H2,1-4H3/b14-8+
Canonical SMILES:	COc1cc2c(cc1O)oc1c(c2=O)c(O)c(c(c1)O)C/C=C(/CCC=C(C)C)C
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	Collection Location	Collection Time	Reference
NPO18783	Garcinia fusca	Species	Clusiaceae	Eukaryota				PMID[12608849]
NPO22337	Garcinia dulcis	Species	Clusiaceae	Eukaryota				TCMID*
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-AUG	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota				PMID[19299148]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota				TCMID*

Showing 1 to 5 of 5 entries

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Biological Activity

Activity Type	# Activity
IC50	2
MIC	6
Others	9

Activity Type	# Activity
Cell Line	4
Organism	7
Others	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	128	ug/ml	25651042
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128	ug/ml	25651042
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128	ug/ml	25651042
NPT2	Others	Unspecified		Inhibition	=	0	%	12608849
NPT2	Others	Unspecified		Inhibition	=	40.6	%	12608849
NPT2	Others	Unspecified		Inhibition	=	76.6	%	12608849
NPT2	Others	Unspecified		Inhibition	=	97.5	%	12608849
NPT2	Others	Unspecified		IC50	=	398	molar ratio	12608849
NPT2	Others	Unspecified		Inhibition	>	100	%	25651042
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	64	ug/ml	25651042

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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 NPC262286 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	325
0.1-0.2	1251
0.2-0.3	2593
0.3-0.4	6546
0.4-0.5	6500
0.5-0.6	2393
0.6-0.7	3343
0.7-0.8	4118
0.8-0.85	1803
0.85-0.9	1237
0.9-0.95	651
0.95-1	129

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Similarity Score	Similarity Level	Natural Product ID
0.947	High Similarity	NPC275722
0.947	High Similarity	NPC301323
0.947	High Similarity	NPC188203
0.947	High Similarity	NPC106976
0.947	High Similarity	NPC83508

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 NPC262286 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	918
0.2-0.3	1653
0.3-0.4	2645
0.4-0.5	1855
0.5-0.6	1050
0.6-0.7	491
0.7-0.8	151
0.8-0.85	34
0.85-0.9	18
0.9-0.95	3
0.95-1	1

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7012	Intermediate Similarity	NPD5405	Approved
0.7017	Intermediate Similarity	NPD1729	Discontinued
0.7019	Intermediate Similarity	NPD4060	Phase 1
0.7025	Intermediate Similarity	NPD3018	Phase 2
0.7032	Intermediate Similarity	NPD1608	Approved

Showing 1 to 5 of 200 entries

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Structure

CID262286 OpenBabel06191716062D 30 32 0 0 0 0 0 0 0 0999 V2000 6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -3.5000 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 -4.3301 -0.5000 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 6.9282 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 -1.7321 0.0000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 -0.5000 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 -1.5000 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 -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 0.8660 -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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 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 -0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 29 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 2 0 0 0 0 7 14 1 0 0 0 0 8 9 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 10 16 2 0 0 0 0 10 20 1 0 0 0 0 11 17 2 0 0 0 0 11 21 1 0 0 0 0 12 18 1 0 0 0 0 12 19 2 0 0 0 0 15 17 1 0 0 0 0 15 23 2 0 0 0 0 16 19 1 0 0 0 0 16 24 1 0 0 0 0 17 25 1 0 0 0 0 18 20 2 0 0 0 0 18 26 1 0 0 0 0 19 30 1 0 0 0 0 20 29 1 0 0 0 0 21 22 2 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 27 1 0 0 0 0 24 28 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	10386850
ChEMBL	CHEMBL517161
ZINC

Physicochemical Properties

Molecular Weight:	410.17
ALogP:	1.259
MLogP:	3.44
XLogP:	3.462
# Rotatable Bonds:	13
Polar Surface Area:	96.22
# H-Bond Aceptor:	1
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	30

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