NPASS Natural Product

Natural Product: NPC186397

Natural Product ID:	NPC186397
Common Name:	1,3,7-Trihydroxy-2-Prenylxanthone
IUPAC Name:	1,3,7-trihydroxy-2-(3-methylbut-2-enyl)xanthen-9-one
Synonyms:
Molecular Formula:	C18H16O5
Standard InCHIKey:	FLWKTILHZPCXDW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O5/c1-9(2)3-5-11-13(20)8-15-16(17(11)21)18(22)12-7-10(19)4-6-14(12)23-15/h3-4,6-8,19-21H,5H2,1-2H3
Canonical SMILES:	CC(=CCc1c(O)cc2c(c1O)c(=O)c1c(o2)ccc(c1)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	Reference
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	UNPD*
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	UNPD*
NPO10228	Ascochyta viciae	Species	Didymellaceae	Eukaryota	UNPD*
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	UNPD*
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	UNPD*
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	UNPD*
NPO11057	Artocarpus integra	Species	Moraceae	Eukaryota	UNPD*
NPO11471	Garcinia oblongifolia	Species	Clusiaceae	Eukaryota	UNPD*
NPO1154	Neomeris annulata	Species	Dasycladaceae	Eukaryota	UNPD*
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	UNPD*

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Biological Activity

Activity Type	# Activity
IC50	5
MIC	8
Others	2

Activity Type	# Activity
Cell Line	5
Organism	9
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	=	21300	nM	24960143
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	>	128	ug/ml	12932139
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	>	128	ug/ml	12932139
NPT2	Others	Unspecified		IC50	>	10000	nM	24960143
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128	ug/ml	12932139
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	9	mm	12932139
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	128	ug/ml	12932139
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 NPC186397 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	299
0.1-0.2	1273
0.2-0.3	2494
0.3-0.4	6197
0.4-0.5	6835
0.5-0.6	2424
0.6-0.7	3790
0.7-0.8	3961
0.8-0.85	1536
0.85-0.9	1497
0.9-0.95	570
0.95-1	13

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Similarity Score	Similarity Level	Natural Product ID
0.9178	High Similarity	NPC5820
0.9178	High Similarity	NPC124729
0.9178	High Similarity	NPC178343
0.9178	High Similarity	NPC469758
0.9178	High Similarity	NPC306488

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 NPC186397 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	941
0.2-0.3	1406
0.3-0.4	2511
0.4-0.5	2033
0.5-0.6	1212
0.6-0.7	496
0.7-0.8	175
0.8-0.85	47
0.85-0.9	22
0.9-0.95	3
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7169	Intermediate Similarity	NPD5889	Approved
0.7169	Intermediate Similarity	NPD5890	Approved
0.717	Intermediate Similarity	NPD2424	Discontinued
0.7172	Intermediate Similarity	NPD9493	Approved
0.7173	Intermediate Similarity	NPD7783	Phase 2

Showing 1 to 5 of 200 entries

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Structure

CID186397 OpenBabel06191715562D 23 25 0 0 0 0 0 0 0 0999 V2000 -5.1962 1.0000 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 2.5981 -1.5000 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 -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 -1.7321 -2.0000 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 -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 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 -0.8660 -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 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 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 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 5 1 0 0 0 0 3 9 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 1 0 0 0 0 6 14 1 0 0 0 0 7 10 2 0 0 0 0 7 12 1 0 0 0 0 8 13 2 0 0 0 0 8 15 1 0 0 0 0 10 19 1 0 0 0 0 11 13 1 0 0 0 0 11 17 2 0 0 0 0 12 14 2 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 23 1 0 0 0 0 15 16 2 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 2 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	5495920
ChEMBL	CHEMBL506229
ZINC

Physicochemical Properties

Molecular Weight:	312.10
ALogP:	0.0786
MLogP:	2.89
XLogP:	2.084
# Rotatable Bonds:	7
Polar Surface Area:	86.99
# H-Bond Aceptor:	1
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	23

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