NPASS Natural Product

Natural Product: NPC20360

Natural Product ID:	NPC20360
Common Name:	1-O-Acetylrocaglaol
IUPAC Name:	[(1R,3S,3aR,8bS)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3-dihydro-1H-cyclopenta[b][1]benzofuran-1-yl] acetate
Synonyms:	1-O-Acetylrocaglaol
Molecular Formula:	C28H28O7
Standard InCHIKey:	CGFKKPRGWNMNFP-CEYYOHNYSA-N
Standard InCHI:	InChI=1S/C28H28O7/c1-17(29)34-25-16-22(18-8-6-5-7-9-18)28(19-10-12-20(31-2)13-11-19)27(25,30)26-23(33-4)14-21(32-3)15-24(26)35-28/h5-15,22,25,30H,16H2,1-4H3/t22-,25+,27+,28-/m0/s1
Canonical SMILES:	COc1ccc(cc1)[C@]12Oc3c([C@]2(O)[C@@H](C[C@H]1c1ccccc1)OC(=O)C)c(OC)cc(c3)OC
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
NPO3427	Aglaia rubiginosa	Species	Meliaceae	Eukaryota	twigs and leaves			PMID[15043407]

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Biological Activity

Activity Type	# Activity
ED50	6

Activity Type	# Activity
Cell Line	5
Others	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	210	nM	18494522
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	189	nM	19691309
NPT2	Others	Unspecified		ED50	=	210	nM	20815366
NPT737	Cell Line	HUVEC	Homo sapiens	ED50	=	231	nM	20149496
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	273	nM	19691309
NPT91	Cell Line	KB	Homo sapiens	ED50	=	147	nM	20420370

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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 NPC20360 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	233
0.1-0.2	1020
0.2-0.3	2151
0.3-0.4	4703
0.4-0.5	8151
0.5-0.6	3791
0.6-0.7	5976
0.7-0.8	4542
0.8-0.85	298
0.85-0.9	17
0.9-0.95	5
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.8095	Intermediate Similarity	NPC67247
0.8095	Intermediate Similarity	NPC213173
0.8095	Intermediate Similarity	NPC204353
0.8095	Intermediate Similarity	NPC55149
0.8095	Intermediate Similarity	NPC307412

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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 NPC20360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	234
0.1-0.2	807
0.2-0.3	1529
0.3-0.4	2515
0.4-0.5	2162
0.5-0.6	1159
0.6-0.7	603
0.7-0.8	141
0.8-0.85	11
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
0.6835	Remote Similarity	NPD2157	Approved
0.6836	Remote Similarity	NPD7472	Approved
0.6842	Remote Similarity	NPD6971	Discontinued
0.6845	Remote Similarity	NPD6072	Discontinued
0.6846	Remote Similarity	NPD1778	Approved

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Structure

NPC20360 OpenBabel07101718272D 35 39 0 0 1 0 0 0 0 0999 V2000 -1.7885 3.6338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3513 -3.1020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0998 0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4915 3.0727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9363 -2.2366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 -2.6143 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0334 -1.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3368 -2.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2821 -0.7673 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0151 0.0971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7139 -0.8483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5609 -0.6542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2597 -1.5995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4915 1.2155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6873 -0.1773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4289 1.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8802 3.8269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4338 -1.1450 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0916 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1832 -1.5025 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4915 0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4289 1.0382 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6873 1.6798 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8831 0.2869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5458 2.2537 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8831 1.2155 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.5025 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5458 0.7512 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5932 4.7100 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5458 2.2537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7290 -2.2537 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2956 -0.1773 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6873 2.6084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2589 3.1368 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 17 1 0 0 0 0 2 31 1 0 0 0 0 3 32 1 0 0 0 0 4 33 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 9 2 0 0 0 0 8 18 2 0 0 0 0 9 18 1 0 0 0 0 10 12 1 0 0 0 0 10 19 2 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 20 2 0 0 0 0 13 20 1 0 0 0 0 14 21 2 0 0 0 0 14 23 1 0 0 0 0 15 21 1 0 0 0 0 15 24 2 0 0 0 0 16 22 1 0 0 0 0 16 25 1 0 0 0 0 17 29 2 0 0 0 0 17 34 1 0 0 0 0 18 22 1 0 0 0 0 20 31 1 0 0 0 0 21 32 1 0 0 0 0 22 28 1 6 0 0 0 23 26 2 0 0 0 0 23 33 1 0 0 0 0 24 26 1 0 0 0 0 24 35 1 0 0 0 0 25 27 1 1 0 0 0 25 34 1 0 0 0 0 26 27 1 0 0 0 0 27 28 1 6 0 0 0 27 30 1 0 0 0 0 28 19 1 6 0 0 0 28 35 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	11363545
ChEMBL	CHEMBL476922
ZINC

Physicochemical Properties

Molecular Weight:	476.18
ALogP:	-1.2499
MLogP:	3.77
XLogP:	5.905
# Rotatable Bonds:	12
Polar Surface Area:	83.45
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	35

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