NPASS Natural Product

Natural Product: NPC166184

Natural Product ID:	NPC166184
Common Name:	Denudatin A
IUPAC Name:	(2S,3R,3aR)-2-(1,3-benzodioxol-5-yl)-3a-methoxy-3-methyl-5-prop-2-enyl-2,3-dihydro-1-benzofuran-6-one
Synonyms:
Molecular Formula:	C20H20O5
Standard InCHIKey:	GGRIWHJBFXFKGS-OITMNORJSA-N
Standard InCHI:	InChI=1S/C20H20O5/c1-4-5-14-10-20(22-3)12(2)19(25-18(20)9-15(14)21)13-6-7-16-17(8-13)24-11-23-16/h4,6-10,12,19H,1,5,11H2,2-3H3/t12-,19+,20-/m1/s1
Canonical SMILES:	C=CCC1=C[C@]2(OC)C(=CC1=O)O[C@@H]([C@H]2C)c1ccc2c(c1)OCO2
First Find Year:
Max Developmental Stage:
Synthetic Gene Cluster:	;

Species Source

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Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Reference
NPO2639	Caulis piperis kadsurae	NA	NA	NA	TCMSP*
NPO27952	Rhizoma dioscoreae	NA	NA	NA	TCMSP*
NPO29571	Magnoliae flos	NA	NA	NA	TCMSP*
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	PMID[19900811]
NPO4865	Piper kadsura	Species	Piperaceae	Eukaryota	TM-MC*

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Biological Activity

Activity Type	# Activity
Others	1

Activity Type	# Activity
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Inhibition	=	23.2	%	19900811

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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 NPC166184 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	259
0.1-0.2	1046
0.2-0.3	2011
0.3-0.4	4950
0.4-0.5	8007
0.5-0.6	3482
0.6-0.7	7273
0.7-0.8	3451
0.8-0.85	330
0.85-0.9	66
0.9-0.95	13
0.95-1	1

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Similarity Score	Similarity Level	Natural Product ID
0.8235	Intermediate Similarity	NPC220462
0.8239	Intermediate Similarity	NPC471988
0.8239	Intermediate Similarity	NPC209229
0.8243	Intermediate Similarity	NPC473428
0.8247	Intermediate Similarity	NPC476337

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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 NPC166184 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	833
0.2-0.3	1496
0.3-0.4	2612
0.4-0.5	2078
0.5-0.6	1197
0.6-0.7	615
0.7-0.8	73
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6707	Remote Similarity	NPD5090	Approved
0.6707	Remote Similarity	NPD5089	Approved
0.6708	Remote Similarity	NPD6273	Approved
0.6708	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD3750	Approved

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Structure

CID166184 OpenBabel06191715542D 25 28 0 0 1 0 0 0 0 0999 V2000 -2.6831 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7700 3.0316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6705 2.0115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 1.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 -0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3578 2.2226 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5659 1.0169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7569 2.4182 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 4 2 0 0 0 0 2 12 1 0 0 0 0 3 22 1 0 0 0 0 4 5 1 0 0 0 0 5 14 1 0 0 0 0 6 7 2 0 0 0 0 6 13 1 0 0 0 0 7 16 1 0 0 0 0 8 13 2 0 0 0 0 8 17 1 0 0 0 0 9 15 1 0 0 0 0 9 18 2 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 23 1 0 0 0 0 11 24 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 6 0 0 0 14 15 1 0 0 0 0 15 21 2 0 0 0 0 16 17 2 0 0 0 0 16 23 1 0 0 0 0 17 24 1 0 0 0 0 18 20 1 0 0 0 0 18 25 1 0 0 0 0 19 13 1 1 0 0 0 19 25 1 0 0 0 0 20 22 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	13336517
ChEMBL	CHEMBL606463
ZINC

Physicochemical Properties

Molecular Weight:	340.13
ALogP:	0.2409
MLogP:	3.11
XLogP:	2.992
# Rotatable Bonds:	6
Polar Surface Area:	53.99
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	25

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