NPASS Natural Product

Natural Product: NPC274730

Natural Product ID:	NPC274730
Common Name:	1,3,5,7-Tetrahydroxy-8-Isoprenylxanthone
IUPAC Name:	2,4,6,8-tetrahydroxy-1-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:
Molecular Formula:	C18H16O6
Standard InCHIKey:	BRERQMIMCLBRCS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-8(2)3-4-10-11(20)7-13(22)18-15(10)17(23)16-12(21)5-9(19)6-14(16)24-18/h3,5-7,19-22H,4H2,1-2H3
Canonical SMILES:	CC(=CCc1c(O)cc(c2c1c(=O)c1c(o2)cc(cc1O)O)O)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	Reference
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota		UNPD*
NPO16291	Leptochloa digitata	Species	Poaceae	Eukaryota		UNPD*
NPO1755	Pinus heldreichii	Species	Pinaceae	Eukaryota		UNPD*
NPO17885	Eupatorium sachalinense	Species	Asteraceae	Eukaryota		UNPD*
NPO18013	Sceletium subvelutinum	NA	NA	NA		UNPD*
NPO18412	Lobophytum microlobulatum	Species	Alcyoniidae	Eukaryota		UNPD*
NPO18911	Piper umbellatum	Species	Piperaceae	Eukaryota		UNPD*
NPO19563	Gyrophora hyperborea	NA	NA	NA		UNPD*
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota		UNPD*
NPO32711	garcinia esculenta	Species	Clusiaceae	Eukaryota	Twigs	PMID[24960143]

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Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	4
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	=	6400	nM	24960143
NPT2	Others	Unspecified		IC50	>	10000	nM	24960143
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000	nM	24960143
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000	nM	24960143
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000	nM	24960143

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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 NPC274730 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	334
0.1-0.2	1252
0.2-0.3	2603
0.3-0.4	6643
0.4-0.5	6444
0.5-0.6	2337
0.6-0.7	3483
0.7-0.8	4214
0.8-0.85	2007
0.85-0.9	957
0.9-0.95	548
0.95-1	67

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Similarity Score	Similarity Level	Natural Product ID
0.9338	High Similarity	NPC149614
0.9342	High Similarity	NPC273462
0.9342	High Similarity	NPC472915
0.9342	High Similarity	NPC33051
0.9342	High Similarity	NPC227337

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 NPC274730 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	346
0.1-0.2	920
0.2-0.3	1631
0.3-0.4	2671
0.4-0.5	1855
0.5-0.6	1039
0.6-0.7	502
0.7-0.8	149
0.8-0.85	29
0.85-0.9	15
0.9-0.95	4
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6993	Remote Similarity	NPD17	Approved
0.6994	Remote Similarity	NPD7033	Discontinued
0.6994	Remote Similarity	NPD4308	Phase 3
0.7	Intermediate Similarity	NPD7699	Phase 2
0.7	Intermediate Similarity	NPD6233	Phase 2

Showing 1 to 5 of 200 entries

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Structure

CID274730 OpenBabel06191716082D 24 26 0 0 0 0 0 0 0 0999 V2000 -1.7321 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 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 1.7321 -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 -2.5981 4.5000 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 -1.7321 2.0000 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 1.7321 2.0000 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 -0.8660 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 0.0000 2.0000 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 3.4641 -0.0000 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 3.0000 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 3.0000 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 8 1 0 0 0 0 2 8 1 0 0 0 0 3 4 1 0 0 0 0 3 8 2 0 0 0 0 4 10 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 9 1 0 0 0 0 6 14 2 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 15 2 0 0 0 0 11 20 1 0 0 0 0 12 16 2 0 0 0 0 12 21 1 0 0 0 0 13 18 2 0 0 0 0 13 22 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 18 1 0 0 0 0 16 17 1 0 0 0 0 17 23 2 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5493670
ChEMBL	CHEMBL3314605
ZINC

Physicochemical Properties

Molecular Weight:	328.09
ALogP:	-0.3817
MLogP:	2.78
XLogP:	1.121
# Rotatable Bonds:	8
Polar Surface Area:	107.22
# H-Bond Aceptor:	1
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	24

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