NPASS Natural Product

Natural Product: NPC202495

Natural Product ID:	NPC202495
Common Name:	Papilistatin
IUPAC Name:	8-methoxynaphtho[2,1-g][1,3]benzodioxole-5,6-dicarboxylic acid
Synonyms:	Papilistatin
Molecular Formula:	C18H12O7
Standard InCHIKey:	KTEBZKXXNMHJFH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H12O7/c1-23-12-4-2-3-8-9(12)5-10(17(19)20)14-11(18(21)22)6-13-16(15(8)14)25-7-24-13/h2-6H,7H2,1H3,(H,19,20)(H,21,22)
Canonical SMILES:	COc1cccc2c1cc(C(=O)O)c1c2c2OCOc2cc1C(=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	Collection Location	Collection Time	Reference
NPO6170	Caulis akebiae	NA	NA	NA				TCMSP*

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Biological Activity

Activity Type	# Activity
GI50	2
MIC	5

Activity Type	# Activity
Cell Line	2
Organism	5

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1081	Cell Line	BXPC-3	Homo sapiens	GI50	=	0.093	ug/ml	20085286
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	32	ug/ml	20085286
NPT1522	Organism	Neisseria gonorrhoeae	Neisseria gonorrhoeae	MIC	=	8	ug/ml	20085286
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64	ug/ml	20085286
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	16	ug/ml	20085286
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	=	0.096	ug/ml	20085286
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	16	ug/ml	20085286

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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 NPC202495 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	295
0.1-0.2	1247
0.2-0.3	2163
0.3-0.4	5136
0.4-0.5	7612
0.5-0.6	2889
0.6-0.7	4705
0.7-0.8	6329
0.8-0.85	440
0.85-0.9	61
0.9-0.95	10
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.8253	Intermediate Similarity	NPC100425
0.8253	Intermediate Similarity	NPC308156
0.8255	Intermediate Similarity	NPC285776
0.8256	Intermediate Similarity	NPC329161
0.8256	Intermediate Similarity	NPC470091

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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 NPC202495 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	305
0.1-0.2	910
0.2-0.3	1435
0.3-0.4	2480
0.4-0.5	2172
0.5-0.6	1143
0.6-0.7	535
0.7-0.8	165
0.8-0.85	13
0.85-0.9	3
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6909	Remote Similarity	NPD2796	Approved
0.6909	Remote Similarity	NPD4476	Approved
0.6914	Remote Similarity	NPD4307	Phase 2
0.6914	Remote Similarity	NPD5402	Approved
0.6923	Remote Similarity	NPD8319	Approved

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Structure

CID202495 OpenBabel06191715592D 25 28 0 0 0 0 0 0 0 0999 V2000 5.2177 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 -0.5039 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 -0.0211 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9602 -0.1009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 2.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 2.8755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5454 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 2.3927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 1.4272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 0.9444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8731 4.8065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2007 3.8410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7092 5.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 5.2892 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0369 4.3237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6354 4.3237 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3816 1.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3529 0.7811 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 23 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 8 1 0 0 0 0 4 12 2 0 0 0 0 5 9 2 0 0 0 0 5 10 1 0 0 0 0 6 11 2 0 0 0 0 6 13 1 0 0 0 0 7 24 1 0 0 0 0 7 25 1 0 0 0 0 8 9 1 0 0 0 0 8 15 2 0 0 0 0 9 12 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 23 1 0 0 0 0 13 16 2 0 0 0 0 13 24 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 25 1 0 0 0 0 17 19 2 0 0 0 0 17 20 1 0 0 0 0 18 21 2 0 0 0 0 18 22 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	46184319
ChEMBL	CHEMBL1087295
ZINC

Physicochemical Properties

Molecular Weight:	340.06
ALogP:	-0.8341
MLogP:	2.67
XLogP:	2.14
# Rotatable Bonds:	6
Polar Surface Area:	102.29
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	25

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