NPASS Natural Product

Natural Product: NPC50535

Natural Product ID:	NPC50535
Common Name:	Adenanthin J
IUPAC Name:
Synonyms:	Adenanthin B; Adenanthin J
Molecular Formula:	C26H36O9
Standard InCHIKey:	MSZRIKPXGUMGBV-PMFMSTFJSA-N
Standard InCHI:	InChI=1S/C26H36O9/c1-11-15-8-16(33-12(2)27)20-25(7)18(34-13(3)28)9-17(30)24(5,6)21(25)19(31)23(35-14(4)29)26(20,10-15)22(11)32/h15-18,20-23,30,32H,1,8-10H2,2-7H3/t15-,16+,17+,18+,20+,21-,22-,23+,25+,26+/m1/s1
Canonical SMILES:	CC(=O)O[C@H]1C[C@@H]2C[C@]3([C@@H]1[C@]1(C)[C@@H](OC(=O)C)C[C@@H](C([C@H]1C(=O)[C@@H]3OC(=O)C)(C)C)O)[C@@H](C2=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	Reference
NPO15942	Isodon wikstroemioides	Species	Lamiaceae	Eukaryota	PMID[24697496]
NPO33364	isodon tenuifolius	Species	Lamiaceae	Eukaryota	PMID[23327668]
NPO6720	Rabdosia adenantha	Species	Lamiaceae	Eukaryota	TCMID*
NPO8269	Isodon nervosus	Species	Lamiaceae	Eukaryota	PMID[18345641]

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Biological Activity

Activity Type	# Activity
IC50	14

Activity Type	# Activity
Cell Line	14

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	>	100000	nM	18345641
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000	nM	23327668
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000	nM	23327668
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	10000	nM	24697496
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	100000	nM	18345641
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000	nM	23327668
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000	nM	24697496
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000	nM	23327668
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000	nM	24697496
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000	nM	18345641

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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 NPC50535 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	165
0.1-0.2	1088
0.2-0.3	3409
0.3-0.4	5921
0.4-0.5	9516
0.5-0.6	4123
0.6-0.7	4271
0.7-0.8	2169
0.8-0.85	161
0.85-0.9	53
0.9-0.95	7
0.95-1	6

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Similarity Score	Similarity Level	Natural Product ID
0.8037	Intermediate Similarity	NPC202793
0.8037	Intermediate Similarity	NPC13149
0.8037	Intermediate Similarity	NPC96268
0.8039	Intermediate Similarity	NPC261333
0.8039	Intermediate Similarity	NPC215271

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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 NPC50535 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	173
0.1-0.2	1881
0.2-0.3	3816
0.3-0.4	2096
0.4-0.5	659
0.5-0.6	247
0.6-0.7	168
0.7-0.8	103
0.8-0.85	18
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
0.6509	Remote Similarity	NPD4197	Approved
0.6531	Remote Similarity	NPD4244	Approved
0.6531	Remote Similarity	NPD4789	Approved
0.6531	Remote Similarity	NPD4245	Approved
0.6545	Remote Similarity	NPD5284	Approved

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Structure

CID50535 OpenBabel06191715382D 35 38 0 0 1 0 0 0 0 0999 V2000 2.1428 -0.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0712 -3.3320 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9086 -1.3432 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5352 2.6863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9303 2.1379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8166 2.1379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.8864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1646 -0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7912 -0.4568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2480 -0.5792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3923 -2.7207 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1410 -1.7864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7676 2.2431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7912 -1.3703 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7911 -1.3703 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1646 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3734 -0.4568 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7912 1.3703 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7911 -0.4568 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5823 0.9135 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9136 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9135 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3735 1.3702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -0.0000 0.0000 C 0 0 2 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 -0.5234 -3.0030 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1410 -2.6727 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0001 2.6863 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9322 1.3566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7912 2.2566 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3620 0.7768 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5823 -1.8271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3734 -1.3432 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7676 1.3567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 24 1 0 0 0 0 6 24 1 0 0 0 0 8 16 1 0 0 0 0 9 17 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 11 15 1 0 0 0 0 11 22 1 0 0 0 0 12 27 2 0 0 0 0 12 33 1 0 0 0 0 13 28 2 0 0 0 0 13 34 1 0 0 0 0 14 29 2 0 0 0 0 14 35 1 0 0 0 0 15 8 1 6 0 0 0 16 20 1 0 0 0 0 16 33 1 6 0 0 0 17 24 1 0 0 0 0 17 30 1 6 0 0 0 18 25 1 1 0 0 0 18 34 1 0 0 0 0 19 21 1 0 0 0 0 19 23 1 0 0 0 0 19 31 2 0 0 0 0 20 25 1 1 0 0 0 20 26 1 0 0 0 0 21 24 1 0 0 0 0 21 25 1 1 0 0 0 22 26 1 6 0 0 0 22 32 1 0 0 0 0 23 26 1 6 0 0 0 23 35 1 0 0 0 0 25 7 1 1 0 0 0 26 10 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	11081505
ChEMBL	CHEMBL468391
ZINC

Physicochemical Properties

Molecular Weight:	492.24
ALogP:	-0.7511
MLogP:	3.33
XLogP:	1.062
# Rotatable Bonds:	14
Polar Surface Area:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	35

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