NPASS Natural Product

Natural Product: NPC139036

Natural Product ID:	NPC139036
Common Name:	Toxyloxanthone B
IUPAC Name:	5,9,11-trihydroxy-3,3-dimethylpyrano[3,2-a]xanthen-12-one
Synonyms:
Molecular Formula:	C18H14O6
Standard InCHIKey:	MFKYNKVEQUTJEH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O6/c1-18(2)4-3-9-14-13(7-11(21)17(9)24-18)23-12-6-8(19)5-10(20)15(12)16(14)22/h3-7,19-21H,1-2H3
Canonical SMILES:	Oc1cc(O)c2c(c1)oc1c(c2=O)c2C=CC(Oc2c(c1)O)(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
NPO11713	Hypericum scabrum	Species	Hypericaceae	Eukaryota		Uzbekistan		PMID[15568778]
NPO32711	garcinia esculenta	Species	Clusiaceae	Eukaryota	Twigs			PMID[24960143]

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Biological Activity

Activity Type	# Activity
IC50	7
Others	2

Activity Type	# Activity
Cell Line	8
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	50000	nM	25082126
NPT2	Others	Unspecified		IC50	>	10000	nM	DrugMatrix in vitro pharmacology data
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000	nM	19783438
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20000	ug/ml	10.6019/CHEMBL1201861
NPT81	Cell Line	A549	Homo sapiens	Inhibition	=	28	%	PubChem BioAssay data set
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000	nM	18061460
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20000	ug/ml	21524583
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000	nM	18163588
NPT83	Cell Line	MCF7	Homo sapiens	Inhibition	=	17	%	19902967

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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 NPC139036 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	355
0.1-0.2	1326
0.2-0.3	2787
0.3-0.4	6938
0.4-0.5	5926
0.5-0.6	2454
0.6-0.7	3601
0.7-0.8	4140
0.8-0.85	1903
0.85-0.9	920
0.9-0.95	510
0.95-1	29

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Similarity Score	Similarity Level	Natural Product ID
0.9286	High Similarity	NPC280530
0.9286	High Similarity	NPC250822
0.9286	High Similarity	NPC75279
0.9286	High Similarity	NPC178964
0.929	High Similarity	NPC471985

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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 NPC139036 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	924
0.2-0.3	1637
0.3-0.4	2686
0.4-0.5	1884
0.5-0.6	1007
0.6-0.7	454
0.7-0.8	153
0.8-0.85	29
0.85-0.9	14
0.9-0.95	3
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6995	Remote Similarity	NPD4665	Approved
0.701	Intermediate Similarity	NPD7907	Approved
0.7016	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3267	Approved
0.7025	Intermediate Similarity	NPD3266	Approved

Showing 1 to 5 of 200 entries

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Structure

NPC139036 OpenBabel07101718332D 24 27 0 0 0 0 0 0 0 0999 V2000 -0.2588 -1.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7934 -0.3912 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 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 6.0622 1.5000 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 5.1962 -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 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 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 0.8660 0.5000 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 6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 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 3.4641 -1.0000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 18 1 0 0 0 0 5 8 2 0 0 0 0 5 10 1 0 0 0 0 6 8 1 0 0 0 0 6 12 2 0 0 0 0 7 11 1 0 0 0 0 7 13 2 0 0 0 0 8 19 1 0 0 0 0 9 14 2 0 0 0 0 9 17 1 0 0 0 0 10 15 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 15 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 15 16 1 0 0 0 0 16 22 2 0 0 0 0 17 24 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	14886044
ChEMBL	CHEMBL482997
ZINC

Physicochemical Properties

Molecular Weight:	326.08
ALogP:	-0.891
MLogP:	2.78
XLogP:	1.051
# Rotatable Bonds:	5
Polar Surface Area:	96.22
# H-Bond Aceptor:	1
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	24

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