NPASS Natural Product

Natural Product: NPC471976

Natural Product ID:	NPC471976
Common Name:	3,5,8-Trihydroxy-2,2-Dimethyl-3,4-Dihydropyrano[3,2-B]Xanthen-6-One
IUPAC Name:	3,5,8-trihydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-b]xanthen-6-one
Synonyms:
Molecular Formula:	C18H16O6
Standard InCHIKey:	RRMPIEAXERVWKC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O6/c1-18(2)14(20)6-10-12(24-18)7-13-15(17(10)22)16(21)9-5-8(19)3-4-11(9)23-13/h3-5,7,14,19-20,22H,6H2,1-2H3
Canonical SMILES:	Oc1ccc2c(c1)c(=O)c1c(o2)cc2c(c1O)CC(C(O2)(C)C)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
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	=	15900	nM	25036789
NPT2	Others	Unspecified		IC50	>	10000	nM	DrugMatrix in vitro pharmacology data
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	10000	nM	22037378
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	10000	nM	18061460
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000	nM	18163588

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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 NPC471976 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	315
0.1-0.2	1123
0.2-0.3	2297
0.3-0.4	5279
0.4-0.5	7276
0.5-0.6	3178
0.6-0.7	3346
0.7-0.8	4188
0.8-0.85	1746
0.85-0.9	1643
0.9-0.95	482
0.95-1	16

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Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC255106
0.9167	High Similarity	NPC278778
0.9167	High Similarity	NPC472916
0.9167	High Similarity	NPC68093
0.9167	High Similarity	NPC291878

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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 NPC471976 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	316
0.1-0.2	851
0.2-0.3	1587
0.3-0.4	2523
0.4-0.5	2005
0.5-0.6	1134
0.6-0.7	504
0.7-0.8	184
0.8-0.85	25
0.85-0.9	30
0.9-0.95	2
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7135	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4060	Phase 1
0.7151	Intermediate Similarity	NPD4287	Approved
0.7152	Intermediate Similarity	NPD9494	Approved

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Structure

NPC471976 OpenBabel07101719242D 24 27 0 0 1 0 0 0 0 0999 V2000 -1.1248 -0.4659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6594 1.1088 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 0.0000 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 -0.0000 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 6.0622 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 0.8660 1.5000 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 0.8660 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 1.5000 0.0000 C 0 0 3 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 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 -0.8660 0.5000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 3.4641 -0.0000 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 8 1 0 0 0 0 4 11 1 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 6 14 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 12 1 0 0 0 0 10 17 2 0 0 0 0 11 23 1 0 0 0 0 12 24 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 17 1 0 0 0 0 16 21 2 0 0 0 0 17 22 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	46872919
ChEMBL	CHEMBL3314606
ZINC

Physicochemical Properties

Molecular Weight:	328.09
ALogP:	-1.3468
MLogP:	2.78
XLogP:	1.175
# Rotatable Bonds:	5
Polar Surface Area:	96.22
# H-Bond Aceptor:	2
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	24

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