NPASS Natural Product

Natural Product: NPC470618

Natural Product ID:	NPC470618
Common Name:	Leonurusoleanolide C
IUPAC Name:	[(1R,2R,3R,4aR,4bS,7S,8R,10aS,10bR,12aR)-3,7-dihydroxy-1-(hydroxymethyl)-1,1',1',4a,10b-pentamethylspiro[2,3,4,4b,5,7,9,10,10a,11,12,12a-dodecahydrochrysene-8,3'-cyclopentane]-2-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms:	leonurusoleanolide C
Molecular Formula:	C38H54O7
Standard InCHIKey:	MUHWBCWYHNOFPM-MHYPQKQYSA-N
Standard InCHI:	InChI=1S/C38H54O7/c1-34(2)17-18-38(21-34)16-13-25-24(32(38)43)9-11-29-35(25,3)15-14-30-36(29,4)20-27(41)33(37(30,5)22-39)45-31(42)12-8-23-7-10-26(40)28(19-23)44-6/h7-10,12,19,25,27,29-30,32-33,39-41,43H,11,13-18,20-22H2,1-6H3/b12-8+/t25-,27-,29+,30-,32-,33+,35+,36-,37+,38-/m1/s1
Canonical SMILES:	OC[C@]1(C)[C@@H](OC(=O)/C=C/c2ccc(c(c2)OC)O)[C@H](O)C[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@H]1CC[C@@]1([C@@H]2O)CCC(C1)(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	Collection Location	Collection Time	Reference
NPO23548	Leonurus japonicus	Species	Lamiaceae	Eukaryota	Fruits			PMID[24328283]

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Biological Activity

Activity Type	# Activity
IC50	5
Others	3

Activity Type	# Activity
Cell Line	6
Others	2

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1229	Cell Line	Huh-7	Homo sapiens	IC50	>	10000	nM	25462271
NPT15	Cell Line	Jurkat	Homo sapiens	IC50	>	10000	nM	25462271
NPT2	Others	Unspecified		IC50	>	10000	nM	18625771
NPT2	Others	Unspecified		IC50	>	10000	nM	2691635
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	42	um	26814680
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	55.1	um	26689485
NPT681	Cell Line	PC-12	Rattus norvegicus	Activity	=	32.1	um	15711537
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000	nM	25462271

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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 NPC470618 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	244
0.1-0.2	1002
0.2-0.3	2011
0.3-0.4	3640
0.4-0.5	6666
0.5-0.6	5717
0.6-0.7	7266
0.7-0.8	4060
0.8-0.85	213
0.85-0.9	32
0.9-0.95	26
0.95-1	12

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Similarity Score	Similarity Level	Natural Product ID
0.8089	Intermediate Similarity	NPC257970
0.8089	Intermediate Similarity	NPC470927
0.8089	Intermediate Similarity	NPC195561
0.8092	Intermediate Similarity	NPC470372
0.8092	Intermediate Similarity	NPC78987

Showing 1 to 5 of 200 entries

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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 NPC470618 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	832
0.2-0.3	1524
0.3-0.4	2502
0.4-0.5	2063
0.5-0.6	1202
0.6-0.7	672
0.7-0.8	108
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6732	Remote Similarity	NPD1611	Approved
0.674	Remote Similarity	NPD6559	Discontinued
0.674	Remote Similarity	NPD6764	Approved
0.674	Remote Similarity	NPD6765	Approved
0.6743	Remote Similarity	NPD4666	Phase 3

Showing 1 to 5 of 200 entries

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Structure

NPC470618 OpenBabel07101718242D 45 50 0 0 1 0 0 0 0 0999 V2000 7.0878 -4.7902 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1743 -5.1970 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 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 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 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 -0.0000 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 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 4.3301 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7788 -3.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1097 -2.5933 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 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3007 -3.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 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 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 2.5981 -0.5000 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 -1.7321 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 2 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2788 -4.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 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 5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 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 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 34 1 0 0 0 0 2 34 1 0 0 0 0 6 44 1 0 0 0 0 7 10 2 0 0 0 0 7 23 1 0 0 0 0 8 12 2 0 0 0 0 8 23 1 0 0 0 0 9 11 1 0 0 0 0 9 24 2 0 0 0 0 10 26 1 0 0 0 0 11 29 1 0 0 0 0 12 31 1 0 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 30 1 0 0 0 0 15 35 1 0 0 0 0 17 18 1 0 0 0 0 17 34 1 0 0 0 0 18 38 1 0 0 0 0 19 23 2 0 0 0 0 19 28 1 0 0 0 0 20 27 1 0 0 0 0 20 36 1 0 0 0 0 21 34 1 0 0 0 0 21 38 1 0 0 0 0 22 37 1 0 0 0 0 22 39 1 0 0 0 0 24 25 1 0 0 0 0 24 32 1 0 0 0 0 25 35 1 1 0 0 0 26 28 2 0 0 0 0 26 40 1 0 0 0 0 27 33 1 0 0 0 0 27 41 1 6 0 0 0 28 44 1 0 0 0 0 29 35 1 1 0 0 0 29 36 1 0 0 0 0 30 36 1 1 0 0 0 30 37 1 0 0 0 0 31 42 2 0 0 0 0 31 45 1 0 0 0 0 32 38 1 1 0 0 0 32 43 1 0 0 0 0 33 37 1 1 0 0 0 33 45 1 0 0 0 0 35 3 1 1 0 0 0 36 4 1 1 0 0 0 37 5 1 1 0 0 0 38 16 1 1 0 0 0 M END $$$$

External Identifiers

PubChem CID	70697407
ChEMBL	CHEMBL2088296
ZINC

Physicochemical Properties

Molecular Weight:	622.39
ALogP:	0.8197
MLogP:	4.87
XLogP:	7.856
# Rotatable Bonds:	16
Polar Surface Area:	116.45
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	45

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