NPASS Compound

Natural Product: NPC285480

Natural Product ID	NPC285480
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Artemisin
IUPAC Name	n.a.
Synonyms	GNF-Pf-5341
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL77
PubChem CID	44266427
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 42 45 0 0 0 0 0 0 0 0999 V2000 1.1183 3.0491 -0.9951 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4478 2.2129 0.0629 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4051 1.7188 1.1098 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3005 0.6168 0.6149 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5005 -0.2391 -0.2893 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1012 -1.6015 -0.4452 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0722 -2.4656 0.7380 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4818 -2.1923 -1.6739 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0853 -2.9547 -2.4669 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1559 -1.8261 -1.8792 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5358 -1.3910 -0.7608 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0236 -0.2148 -0.0359 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4486 1.1344 -0.5147 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8403 1.5069 -0.2828 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7695 0.5517 0.3466 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3276 -0.8721 0.3783 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5271 -1.7428 0.6423 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8877 -1.1642 -0.9350 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3860 -1.1394 1.3546 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3373 -0.3327 1.2925 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5348 3.9411 -0.4753 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9086 2.5660 -1.5452 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3363 3.3926 -1.6965 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1730 2.9797 0.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0661 2.5996 1.3448 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8933 1.4923 2.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7500 0.0860 1.4749 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1406 1.0931 0.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6099 0.1996 -1.3315 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1714 -1.4312 -0.7331 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0479 -2.4114 1.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9656 -3.5270 0.4169 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3123 -2.2261 1.5055 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5247 -2.2626 -0.0291 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1986 1.1275 -1.6210 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9246 2.4714 0.3098 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2984 1.8133 -1.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7837 0.5551 -0.1501 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0096 0.8358 1.4157 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1323 -1.3348 1.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1468 -2.7624 0.9098 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1774 -1.8519 -0.2592 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 2 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 16 19 1 0 19 20 1 0 13 2 1 0 12 5 1 0 18 11 1 0 20 12 1 0 1 21 1 0 1 22 1 0 1 23 1 0 2 24 1 1 3 25 1 0 3 26 1 0 4 27 1 0 4 28 1 0 5 29 1 6 6 30 1 6 7 31 1 0 7 32 1 0 7 33 1 0 11 34 1 1 13 35 1 6 14 36 1 0 14 37 1 0 15 38 1 0 15 39 1 0 17 40 1 0 17 41 1 0 17 42 1 0 M END

Standard InCHIKey	BLUAFEHZUWYNDE-XRNKLDBLSA-N
Standard InCHI	InChI=1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14+,15?/m1/s1
SMILES	C[C@@H]1CC[C@H]2[C@@H](C)C(=O)O[C@H]3C42[C@H]1CC[C@@](C)(O3)OO4

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 21030913]
NPO59040	Artemisia annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s10646-011-0728-8]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO59040	Artemisia annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0032-9592(02)00165-6]
NPO59040	Artemisia annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.2174/1573413711309030012]
NPO59040	Artemisia annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36983962]
NPO59040	Artemisia annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37420038]
NPO59040	Artemisia annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37666615]
NPO59040	Artemisia annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38008924]
NPO59040	Artemisia annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38538562]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO59040	Artemisia annua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11035	Massa medicata fermentata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Potency	28

Activity Type	# Activity
Individual protein	5
Organism	2
Others	21

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	1693	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	1333.3	nM	PubChem BioAssay data set
NPT1197	Individual protein	Huntingtin	Homo sapiens	Potency	=	3162.3	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	14963.1	nM	PubChem BioAssay data set
NPT445	Individual protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	20314.8	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2.7	nM	PubChem BioAssay data set
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	3.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26603.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11883.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23914.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	5955.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2131.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2371	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2984.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1059.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1899.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	473.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	421.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	237.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	44.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	39.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	45479.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2238.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1778.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	132.1	nM	PubChem BioAssay data set

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC285480 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	30225
0.1-0.2	19581
0.2-0.3	32
0.3-0.4	1
0.4-0.5	0
0.5-0.6	5
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC30443
1.0	High Similarity	NPC260977
1.0	High Similarity	NPC45256
0.6346	Remote Similarity	NPC148872
0.6078	Remote Similarity	NPC31046
0.6078	Remote Similarity	NPC209666
0.6078	Remote Similarity	NPC53868
0.6078	Remote Similarity	NPC5209
0.6078	Remote Similarity	NPC51956
0.6078	Remote Similarity	NPC486251
0.6078	Remote Similarity	NPC29005
0.6078	Remote Similarity	NPC486262
0.6078	Remote Similarity	NPC200167
0.6078	Remote Similarity	NPC80142
0.5484	Remote Similarity	NPC30102
0.5484	Remote Similarity	NPC128816
0.5484	Remote Similarity	NPC67158
0.5484	Remote Similarity	NPC484862
0.5192	Remote Similarity	NPC60568

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC285480 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7478
0.1-0.2	1659
0.2-0.3	3
0.3-0.4	0
0.4-0.5	0
0.5-0.6	3
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD1779	Approved
1.0	High Similarity	NPD1780	Phase 4
0.6154	Remote Similarity	NPD2686	Phase 4
0.6154	Remote Similarity	NPD2687	Approved
0.6078	Remote Similarity	NPD1810	Approved
0.6078	Remote Similarity	NPD1811	Phase 4
0.6078	Remote Similarity	NPD2254	Phase 4
0.5484	Remote Similarity	NPD3669	Phase 4
0.5484	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5424	Remote Similarity	NPD3710	Pre-clinical

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data