NPASS Natural Product

Natural Product: NPC287328

Natural Product ID:	NPC287328
Common Name:	3'-O-Methyldiplacol
IUPAC Name:	(2R,3R)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-2,3-dihydrochromen-4-one
Synonyms:	3'-O-Methyldiplacol
Molecular Formula:	C26H30O7
Standard InCHIKey:	YHOYRZLJSAAOGW-WFQOKMFZSA-N
Standard InCHI:	InChI=1S/C26H30O7/c1-14(2)6-5-7-15(3)8-10-17-19(28)13-21-22(23(17)29)24(30)25(31)26(33-21)16-9-11-18(27)20(12-16)32-4/h6,8-9,11-13,25-29,31H,5,7,10H2,1-4H3/b15-8+/t25-,26+/m0/s1
Canonical SMILES:	COc1cc(ccc1O)[C@H]1Oc2cc(O)c(c(c2C(=O)[C@@H]1O)O)C/C=C(/CCC=C(C)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	Reference
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	PMID[22445674]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	PMID[23623680]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	fruits	PMID[25735399]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota	Fruits	PMID[18293924]
NPO22079	Paulownia tomentosa	Species	Paulowniaceae	Eukaryota		PMID[20192247]

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Biological Activity

Activity Type	# Activity
EC50	7
IC50	4
Ki	3
MIC	10

Activity Type	# Activity
Cell Line	8
Individual Protein	4
Organism	10
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1160	Cell Line	BJ	Homo sapiens	EC50	>	10000	nM	9514009
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2	ug/ml	21761866
NPT165	Cell Line	HeLa	Homo sapiens	EC50	>	10000	nM	19908853
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	2	ug/ml	21761866
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4	ug/ml	22206869
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	32	ug/ml	DrugMatrix in vitro pharmacology data
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32	ug/ml	20594858
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	<	10000	nM	19220033
NPT1970	Cell Line	THP-1	Homo sapiens	EC50	>	10000	nM	12408708
NPT2	Others	Unspecified		IC50	=	9500	nM	26147490

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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 NPC287328 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	316
0.1-0.2	1123
0.2-0.3	2409
0.3-0.4	5753
0.4-0.5	7118
0.5-0.6	2686
0.6-0.7	3192
0.7-0.8	4204
0.8-0.85	1836
0.85-0.9	1354
0.9-0.95	808
0.95-1	90

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Similarity Score	Similarity Level	Natural Product ID
0.9355	High Similarity	NPC470402
0.9355	High Similarity	NPC472911
0.9355	High Similarity	NPC472910
0.9355	High Similarity	NPC262286
0.9355	High Similarity	NPC299520

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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 NPC287328 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	319
0.1-0.2	854
0.2-0.3	1620
0.3-0.4	2567
0.4-0.5	1949
0.5-0.6	1080
0.6-0.7	540
0.7-0.8	173
0.8-0.85	26
0.85-0.9	23
0.9-0.95	8
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7095	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7098	Intermediate Similarity	NPD6823	Phase 2
0.7101	Intermediate Similarity	NPD4662	Approved
0.7101	Intermediate Similarity	NPD4661	Approved
0.7108	Intermediate Similarity	NPD6674	Discontinued

Showing 1 to 5 of 200 entries

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Structure

NPC287328 OpenBabel07101719252D 33 35 0 0 1 0 0 0 0 0999 V2000 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 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 -2.5981 0.5000 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 -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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 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 -1.7321 -0.0000 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 -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 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 1.7321 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 -0.8660 1.5000 0.0000 C 0 0 1 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 -4.3301 -1.5000 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 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 4 32 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 15 1 0 0 0 0 8 10 1 0 0 0 0 8 15 2 0 0 0 0 9 11 2 0 0 0 0 9 16 1 0 0 0 0 10 17 1 0 0 0 0 11 18 1 0 0 0 0 12 16 2 0 0 0 0 12 20 1 0 0 0 0 13 19 2 0 0 0 0 13 21 1 0 0 0 0 17 19 1 0 0 0 0 17 23 2 0 0 0 0 18 20 2 0 0 0 0 18 27 1 0 0 0 0 19 28 1 0 0 0 0 20 32 1 0 0 0 0 21 22 2 0 0 0 0 21 33 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 23 29 1 0 0 0 0 24 25 1 0 0 0 0 24 30 2 0 0 0 0 25 26 1 0 0 0 0 25 31 1 1 0 0 0 26 16 1 6 0 0 0 26 33 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	21607150
ChEMBL	CHEMBL459258
ZINC

Physicochemical Properties

Molecular Weight:	454.20
ALogP:	0.5912
MLogP:	3.55
XLogP:	3.41
# Rotatable Bonds:	15
Polar Surface Area:	116.45
# H-Bond Aceptor:	2
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	33

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