NPASS Natural Product

Natural Product: NPC101012

Natural Product ID:	NPC101012
Common Name:	Rel-Plicatilisin B
IUPAC Name:	(3R,3aR,5aR,8S)-8,10-dihydroxy-9-(hydroxymethyl)-3a,5a-dimethyl-3-propan-2-yl-3,4,5,6,7,8-hexahydro-1H-benzo[f]azulen-2-one
Synonyms:	Rel-Plicatilisin B
Molecular Formula:	C20H30O4
Standard InCHIKey:	PCSZVWIDBZFNQB-QHERXFFYSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-11(2)16-15(23)9-13-18(24)17-12(10-21)14(22)5-6-19(17,3)7-8-20(13,16)4/h11,14,16,21-22,24H,5-10H2,1-4H3/t14-,16-,19-,20-/m0/s1
Canonical SMILES:	OCC1=C2C(=C3CC(=O)[C@@H]([C@]3(CC[C@@]2(CC[C@@H]1O)C)C)C(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
NPO32901	coprinus plicatilis	Species	Agaricaceae	Eukaryota				PMID[22749279]

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Biological Activity

Activity Type	# Activity
IC50	6

Activity Type	# Activity
Cell Line	6

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1045	Cell Line	U2OS	Homo sapiens	IC50	>	50000	nM	18183025
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	50000	nM	12502340
NPT393	Cell Line	HCT-116	Homo sapiens	IC50	=	38900	nM	18183025
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	>	50000	nM	18183025
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	25900	nM	11575942
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000	nM	PubChem BioAssay data set

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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 NPC101012 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	106
0.1-0.2	748
0.2-0.3	3340
0.3-0.4	9370
0.4-0.5	8215
0.5-0.6	5681
0.6-0.7	3116
0.7-0.8	313
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Natural Product ID
0.7113	Intermediate Similarity	NPC10364
0.7126	Intermediate Similarity	NPC472478
0.7128	Intermediate Similarity	NPC152897
0.7128	Intermediate Similarity	NPC109305
0.7128	Intermediate Similarity	NPC66429

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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 NPC101012 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	121
0.1-0.2	1331
0.2-0.3	3955
0.3-0.4	2607
0.4-0.5	692
0.5-0.6	206
0.6-0.7	240
0.7-0.8	9
0.8-0.85	0
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
0.6147	Remote Similarity	NPD5251	Approved
0.6147	Remote Similarity	NPD5248	Approved
0.6147	Remote Similarity	NPD6883	Approved
0.6147	Remote Similarity	NPD7290	Approved
0.6147	Remote Similarity	NPD5247	Approved

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Structure

NPC101012 OpenBabel07101718272D 24 26 0 0 1 0 0 0 0 0999 V2000 -4.8441 -0.1485 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5922 1.0484 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5633 -0.8262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5145 0.2368 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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 0.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7568 0.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4796 -2.0920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8727 0.0886 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 -1.7568 -1.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3601 -1.6182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1816 -0.6342 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7818 -1.6235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1906 -0.5000 0.0000 C 0 0 2 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 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2611 -2.0520 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5593 -2.5984 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 11 1 0 0 0 0 5 6 1 0 0 0 0 5 14 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 13 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 17 2 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 22 1 6 0 0 0 15 16 1 0 0 0 0 15 23 2 0 0 0 0 16 20 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 24 1 0 0 0 0 19 3 1 1 0 0 0 20 4 1 6 0 0 0 M END $$$$

External Identifiers

PubChem CID	62707592
ChEMBL	CHEMBL2057716
ZINC

Physicochemical Properties

Molecular Weight:	334.21
ALogP:	-0.5309
MLogP:	3.22
XLogP:	2.112
# Rotatable Bonds:	9
Polar Surface Area:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	24

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