NPASS Natural Product

Natural Product: NPC295650

Natural Product ID:	NPC295650
Common Name:	3-O-[(S)-2-Methylbutyroyl]Pinobanksin
IUPAC Name:	[(2R,3R)-5,7-dihydroxy-4-oxo-2-phenyl-2,3-dihydrochromen-3-yl] (2S)-2-methylbutanoate
Synonyms:
Molecular Formula:	C20H20O6
Standard InCHIKey:	ZDDSHWOLTYMTJG-SYURPWHHSA-N
Standard InCHI:	InChI=1S/C20H20O6/c1-3-11(2)20(24)26-19-17(23)16-14(22)9-13(21)10-15(16)25-18(19)12-7-5-4-6-8-12/h4-11,18-19,21-22H,3H2,1-2H3/t11-,18+,19-/m0/s1
Canonical SMILES:	CC[C@@H](C(=O)O[C@@H]1[C@H](Oc2c(C1=O)c(O)cc(c2)O)c1ccccc1)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
NPO32539	chinese propolis	Species	Rhytismataceae	Eukaryota				PMID[12027739]

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Biological Activity

Activity Type	# Activity
EC50	5

Activity Type	# Activity
Cell Line	3
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	EC50	=	116000	nM	22401866
NPT2	Others	Unspecified		EC50	=	185000	nM	19716307
NPT2	Others	Unspecified		EC50	=	78900	nM	DrugMatrix in vitro pharmacology data
NPT453	Cell Line	HT-1080	Homo sapiens	EC50	=	143000	nM	17125236
NPT81	Cell Line	A549	Homo sapiens	EC50	=	160000	nM	11975483

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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 NPC295650 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	248
0.1-0.2	1028
0.2-0.3	2169
0.3-0.4	4936
0.4-0.5	7625
0.5-0.6	3448
0.6-0.7	3631
0.7-0.8	4233
0.8-0.85	1926
0.85-0.9	1343
0.9-0.95	301
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.9097	High Similarity	NPC287246
0.9097	High Similarity	NPC13768
0.9097	High Similarity	NPC295261
0.9097	High Similarity	NPC296490
0.9097	High Similarity	NPC79943

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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 NPC295650 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	270
0.1-0.2	801
0.2-0.3	1480
0.3-0.4	2404
0.4-0.5	2112
0.5-0.6	1289
0.6-0.7	542
0.7-0.8	201
0.8-0.85	32
0.85-0.9	21
0.9-0.95	9
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7195	Intermediate Similarity	NPD4661	Approved
0.72	Intermediate Similarity	NPD7228	Approved
0.72	Intermediate Similarity	NPD1535	Discovery
0.7219	Intermediate Similarity	NPD5353	Approved
0.7226	Intermediate Similarity	NPD411	Approved

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Structure

NPC295650 OpenBabel07101718222D 26 28 0 0 1 0 0 0 0 0999 V2000 -3.4641 -2.0000 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 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -3.4641 -0.0000 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 -2.5981 -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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 1 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 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 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 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 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 3.4641 0.0000 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 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 3 11 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 8 2 0 0 0 0 7 12 2 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 2 1 1 0 0 0 11 20 1 0 0 0 0 13 21 1 0 0 0 0 14 16 2 0 0 0 0 14 22 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 18 12 1 1 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 26 1 6 0 0 0 20 24 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	636686
ChEMBL	CHEMBL464454
ZINC

Physicochemical Properties

Molecular Weight:	356.13
ALogP:	-1.579
MLogP:	3
XLogP:	3.584
# Rotatable Bonds:	9
Polar Surface Area:	93.06
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	26

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