NPASS Natural Product

Natural Product: NPC30102

Natural Product ID:	NPC30102
Common Name:	Artesunate
IUPAC Name:
Synonyms:	Arsumax; Artesunate
Molecular Formula:	C19H28O8
Standard InCHIKey:	FIHJKUPKCHIPAT-AHIGJZGOSA-N
Standard InCHI:	InChI=1S/C19H28O8/c1-10-4-5-13-11(2)16(23-15(22)7-6-14(20)21)24-17-19(13)12(10)8-9-18(3,25-17)26-27-19/h10-13,16-17H,4-9H2,1-3H3,(H,20,21)/t10-,11-,12+,13+,16-,17-,18-,19-/m1/s1
Canonical SMILES:	OC(=O)CCC(=O)O[C@@H]1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H]([C@H]1C)CC[C@H]4C)OO3
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
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota				TM-MC*
NPO26589	Artemisia annua	Species	Asteraceae	Eukaryota				TM-MC*

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Biological Activity

Activity Type	# Activity
EC50	4
ED50	18
IC50	183
Others	146

Activity Type	# Activity
Cell Line	28
Individual Protein	2
Organism	278
Others	41
Protein Complex	1
Subcellular	1

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Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1086	Cell Line	SK-HEP1	Homo sapiens	IC50	=	10000	nM	23685181
NPT111	Cell Line	K562	Homo sapiens	IC50	=	5999	nM	26615886
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2000	nM	24148834
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	3200	nM	23013253
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	19014	nM	26615886
NPT171	Cell Line	MRC5	Homo sapiens	Ratio IC50	=	2		23013253
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	6800	nM	23013253
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	36000	nM	25089179
NPT2	Others	Unspecified		IC50	=	989	nM	15999998
NPT2	Others	Unspecified		IC50	=	2.1	nM	19908867

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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 NPC30102 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	215
0.1-0.2	2068
0.2-0.3	5764
0.3-0.4	11431
0.4-0.5	5506
0.5-0.6	4278
0.6-0.7	1540
0.7-0.8	73
0.8-0.85	4
0.85-0.9	8
0.9-0.95	0
0.95-1	2

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Similarity Score	Similarity Level	Natural Product ID
0.6733	Remote Similarity	NPC41843
0.6735	Remote Similarity	NPC267238
0.6735	Remote Similarity	NPC252253
0.6735	Remote Similarity	NPC253611
0.6735	Remote Similarity	NPC77717

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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 NPC30102 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	271
0.1-0.2	3213
0.2-0.3	3807
0.3-0.4	1181
0.4-0.5	464
0.5-0.6	185
0.6-0.7	31
0.7-0.8	0
0.8-0.85	3
0.85-0.9	4
0.9-0.95	0
0.95-1	2

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Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.5607	Remote Similarity	NPD7902	Approved
0.5614	Remote Similarity	NPD8087	Discontinued
0.5618	Remote Similarity	NPD897	Approved
0.5618	Remote Similarity	NPD896	Approved
0.5618	Remote Similarity	NPD898	Approved

Showing 1 to 5 of 82 entries

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Structure

CID30102 OpenBabel06191715352D 27 30 0 0 1 0 0 0 0 0999 V2000 -2.0046 -2.5509 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2786 -0.2186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9340 -1.3103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1550 -1.1708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1360 -0.6179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7571 -3.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7398 -3.6458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6619 -2.2022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2751 -2.2724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7345 -1.5303 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3643 -0.7464 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1913 -1.4258 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6919 -0.2880 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9317 -3.9183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5652 -2.9875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4251 -1.5579 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9143 -1.5836 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9143 -1.5836 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9143 -0.5279 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0890 -4.9622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 -3.5326 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5479 -3.3732 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4078 -1.9436 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8286 -2.1114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.1114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9143 -0.5279 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 4 5 1 0 0 0 0 4 10 1 0 0 0 0 5 13 1 0 0 0 0 6 7 1 0 0 0 0 6 14 1 0 0 0 0 7 15 1 0 0 0 0 8 9 1 0 0 0 0 8 12 1 0 0 0 0 9 18 1 0 0 0 0 10 1 1 6 0 0 0 10 12 1 0 0 0 0 11 2 1 6 0 0 0 11 13 1 0 0 0 0 11 16 1 0 0 0 0 12 19 1 1 0 0 0 13 19 1 1 0 0 0 14 20 2 0 0 0 0 14 21 1 0 0 0 0 15 22 2 0 0 0 0 15 23 1 0 0 0 0 16 23 1 1 0 0 0 16 24 1 0 0 0 0 17 19 1 1 0 0 0 17 24 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 1 0 0 0 18 25 1 0 0 0 0 18 26 1 0 0 0 0 19 27 1 6 0 0 0 26 27 1 0 0 0 0 M END $$$$

External Identifiers

PubChem CID	6917864
ChEMBL	CHEMBL361497
ZINC

Physicochemical Properties

Molecular Weight:	384.18
ALogP:	0.4477
MLogP:	2.67
XLogP:	2.925
# Rotatable Bonds:	9
Polar Surface Area:	100.52
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	27

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