NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	248.14
Volume:	254.868
LogP:	2.795
LogD:	2.565
LogS:	-4.293
# Rotatable Bonds:	0
TPSA:	38.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	5.178
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.682
MDCK Permeability:	3.083088813582435e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.008
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.278
Plasma Protein Binding (PPB):	67.71393585205078%
Volume Distribution (VD):	1.234
Pgp-substrate:	24.344083786010742%

ADMET: Metabolism

CYP1A2-inhibitor:	0.733
CYP1A2-substrate:	0.823
CYP2C19-inhibitor:	0.168
CYP2C19-substrate:	0.698
CYP2C9-inhibitor:	0.18
CYP2C9-substrate:	0.051
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.623
CYP3A4-inhibitor:	0.098
CYP3A4-substrate:	0.24

ADMET: Excretion

Clearance (CL):	6.652
Half-life (T1/2):	0.697

ADMET: Toxicity

hERG Blockers:	0.757
Human Hepatotoxicity (H-HT):	0.99
Drug-inuced Liver Injury (DILI):	0.622
AMES Toxicity:	0.542
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.928
Skin Sensitization:	0.823
Carcinogencity:	0.072
Eye Corrosion:	0.726
Eye Irritation:	0.233
Respiratory Toxicity:	0.982

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC66581

Natural Product ID:	NPC66581
*Common Name:**	Arteannuin B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QWQSMEDUZQDVLA-KPHNHPKPSA-N
Standard InCHI:	InChI=1S/C15H20O3/c1-8-4-5-11-9(2)12(16)17-15(11)10(8)6-7-14(3)13(15)18-14/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10+,11+,13-,14-,15-/m1/s1
SMILES:	C[C@@H]1CC[C@H]2C(=C)C(=O)O[C@@]32[C@H]1CC[C@]1(C)[C@H]3O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515516
PubChem CID:	6543478
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0002048] Cadinanolides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

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.	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]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10506	Artemisia apiacea	Species	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]
NPO10506	Artemisia apiacea	Species	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]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10506	Artemisia apiacea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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	NP ID	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
AC50	3
IC50	1
Others	2
Potency	19

Activity Type	# Activity
Individual Protein	14
NON-MOLECULAR	3
Others	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1282	Individual Protein	Microphthalmia-associated transcription factor	Homo sapiens	AC50	=	5222.0	nM	PMID[528387]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	14581.0	nM	PMID[528387]
NPT64	Individual Protein	ATPase family AAA domain-containing protein 5	Homo sapiens	Potency	n.a.	20587.8	nM	PMID[528387]
NPT135	Individual Protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[528387]
NPT154	Individual Protein	Mothers against decapentaplegic homolog 3	Homo sapiens	Potency	n.a.	14125.4	nM	PMID[528387]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	18356.4	nM	PMID[528387]
NPT10	Individual Protein	Geminin	Homo sapiens	Potency	n.a.	4109.5	nM	PMID[528387]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	22387.2	nM	PMID[528387]
NPT101	Individual Protein	Glucagon-like peptide 1 receptor	Homo sapiens	Potency	n.a.	19952.6	nM	PMID[528387]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	20596.2	nM	PMID[528387]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	12995.3	nM	PMID[528387]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	47000.0	nM	PMID[528386]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC80	>	50.0	uM	PMID[528386]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	=	44.8	%	PMID[528386]
NPT2	Others	Unspecified		Potency	n.a.	32642.7	nM	PMID[528387]
NPT2	Others	Unspecified		Potency	n.a.	6513.1	nM	PMID[528387]
NPT2	Others	Unspecified		Potency	n.a.	4466.8	nM	PMID[528387]
NPT2	Others	Unspecified		Potency	n.a.	2818.4	nM	PMID[528387]
NPT861	Individual Protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	29092.9	nM	PMID[528387]
NPT2	Others	Unspecified		Potency	n.a.	31471.6	nM	PMID[528387]
NPT2	Others	Unspecified		Potency	n.a.	14125.4	nM	PMID[528387]
NPT2	Others	Unspecified		Potency	n.a.	28183.8	nM	PMID[528387]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available 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 NPC66581 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	257
0.1-0.2	1786
0.2-0.3	5644
0.3-0.4	9720
0.4-0.5	12642
0.5-0.6	7816
0.6-0.7	4047
0.7-0.8	730
0.8-0.85	46
0.85-0.9	5
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC56369
0.9032	High Similarity	NPC474921
0.875	High Similarity	NPC475958
0.8614	High Similarity	NPC253906
0.8587	High Similarity	NPC475776
0.85	High Similarity	NPC180744
0.8485	Intermediate Similarity	NPC477127
0.8485	Intermediate Similarity	NPC283850
0.8462	Intermediate Similarity	NPC175293
0.8438	Intermediate Similarity	NPC136781
0.8421	Intermediate Similarity	NPC90014
0.8384	Intermediate Similarity	NPC61442
0.8333	Intermediate Similarity	NPC93245
0.8333	Intermediate Similarity	NPC469370
0.8333	Intermediate Similarity	NPC473964
0.8316	Intermediate Similarity	NPC225474
0.8316	Intermediate Similarity	NPC473434
0.8316	Intermediate Similarity	NPC469596
0.8316	Intermediate Similarity	NPC148000
0.8316	Intermediate Similarity	NPC471446
0.8316	Intermediate Similarity	NPC474841
0.8315	Intermediate Similarity	NPC226988
0.8298	Intermediate Similarity	NPC165180
0.828	Intermediate Similarity	NPC116620
0.8247	Intermediate Similarity	NPC473963
0.8229	Intermediate Similarity	NPC157686
0.8229	Intermediate Similarity	NPC259042
0.82	Intermediate Similarity	NPC72842
0.82	Intermediate Similarity	NPC99510
0.8173	Intermediate Similarity	NPC469655
0.8173	Intermediate Similarity	NPC469656
0.8173	Intermediate Similarity	NPC474846
0.8163	Intermediate Similarity	NPC476806
0.8163	Intermediate Similarity	NPC476807
0.8152	Intermediate Similarity	NPC9231
0.8125	Intermediate Similarity	NPC24861
0.8125	Intermediate Similarity	NPC476722
0.8095	Intermediate Similarity	NPC222834
0.8061	Intermediate Similarity	NPC111348
0.8058	Intermediate Similarity	NPC37628
0.8037	Intermediate Similarity	NPC477509
0.8022	Intermediate Similarity	NPC194637
0.8019	Intermediate Similarity	NPC477126
0.7981	Intermediate Similarity	NPC154906
0.7961	Intermediate Similarity	NPC78966
0.7961	Intermediate Similarity	NPC284732
0.7959	Intermediate Similarity	NPC228766
0.7959	Intermediate Similarity	NPC165528
0.7935	Intermediate Similarity	NPC219011
0.7935	Intermediate Similarity	NPC470011
0.79	Intermediate Similarity	NPC47024
0.7872	Intermediate Similarity	NPC181103
0.7872	Intermediate Similarity	NPC5130
0.7872	Intermediate Similarity	NPC305029
0.7849	Intermediate Similarity	NPC38468
0.7849	Intermediate Similarity	NPC50362
0.7849	Intermediate Similarity	NPC319795
0.7835	Intermediate Similarity	NPC147272
0.7812	Intermediate Similarity	NPC152467
0.7802	Intermediate Similarity	NPC38642
0.78	Intermediate Similarity	NPC216478
0.7798	Intermediate Similarity	NPC58662
0.7798	Intermediate Similarity	NPC469684
0.7798	Intermediate Similarity	NPC13713
0.7789	Intermediate Similarity	NPC50847
0.7778	Intermediate Similarity	NPC256227
0.7778	Intermediate Similarity	NPC284518
0.7766	Intermediate Similarity	NPC477920
0.7766	Intermediate Similarity	NPC85698
0.7745	Intermediate Similarity	NPC164551
0.7742	Intermediate Similarity	NPC470238
0.7742	Intermediate Similarity	NPC138647
0.7742	Intermediate Similarity	NPC97505
0.7732	Intermediate Similarity	NPC49420
0.7708	Intermediate Similarity	NPC151770
0.7708	Intermediate Similarity	NPC194642
0.7706	Intermediate Similarity	NPC270478
0.7692	Intermediate Similarity	NPC470975
0.7692	Intermediate Similarity	NPC103088
0.7692	Intermediate Similarity	NPC470979
0.7685	Intermediate Similarity	NPC470120
0.7684	Intermediate Similarity	NPC231889
0.7684	Intermediate Similarity	NPC470012
0.767	Intermediate Similarity	NPC254202
0.7658	Intermediate Similarity	NPC475520
0.7647	Intermediate Similarity	NPC242666
0.7647	Intermediate Similarity	NPC308824
0.7642	Intermediate Similarity	NPC471934
0.7642	Intermediate Similarity	NPC474243
0.764	Intermediate Similarity	NPC92489
0.7636	Intermediate Similarity	NPC53396
0.7636	Intermediate Similarity	NPC98249
0.7634	Intermediate Similarity	NPC272814
0.7634	Intermediate Similarity	NPC474472
0.7634	Intermediate Similarity	NPC257358
0.7634	Intermediate Similarity	NPC127917
0.7629	Intermediate Similarity	NPC475748
0.7619	Intermediate Similarity	NPC474716
0.7619	Intermediate Similarity	NPC469558
0.7615	Intermediate Similarity	NPC90472
0.7611	Intermediate Similarity	NPC170538
0.76	Intermediate Similarity	NPC148872
0.7596	Intermediate Similarity	NPC301787
0.7593	Intermediate Similarity	NPC269530
0.7589	Intermediate Similarity	NPC143755
0.7589	Intermediate Similarity	NPC4548
0.7579	Intermediate Similarity	NPC470242
0.7576	Intermediate Similarity	NPC250075
0.7576	Intermediate Similarity	NPC476716
0.7568	Intermediate Similarity	NPC284707
0.7568	Intermediate Similarity	NPC473720
0.7556	Intermediate Similarity	NPC143250
0.7551	Intermediate Similarity	NPC70251
0.7551	Intermediate Similarity	NPC476934
0.7551	Intermediate Similarity	NPC475881
0.7549	Intermediate Similarity	NPC471413
0.7549	Intermediate Similarity	NPC477656
0.7547	Intermediate Similarity	NPC273155
0.7547	Intermediate Similarity	NPC255082
0.7544	Intermediate Similarity	NPC11895
0.7526	Intermediate Similarity	NPC73995
0.7525	Intermediate Similarity	NPC474395
0.7524	Intermediate Similarity	NPC222833
0.7524	Intermediate Similarity	NPC138908
0.7524	Intermediate Similarity	NPC200957
0.7523	Intermediate Similarity	NPC33360
0.7522	Intermediate Similarity	NPC310511
0.75	Intermediate Similarity	NPC470467
0.75	Intermediate Similarity	NPC472667
0.75	Intermediate Similarity	NPC217329
0.75	Intermediate Similarity	NPC190753
0.75	Intermediate Similarity	NPC474981
0.75	Intermediate Similarity	NPC157476
0.75	Intermediate Similarity	NPC270270
0.75	Intermediate Similarity	NPC156681
0.7478	Intermediate Similarity	NPC81736
0.7478	Intermediate Similarity	NPC172154
0.7477	Intermediate Similarity	NPC473590
0.7477	Intermediate Similarity	NPC478204
0.7476	Intermediate Similarity	NPC98225
0.7476	Intermediate Similarity	NPC111292
0.7476	Intermediate Similarity	NPC252614
0.7476	Intermediate Similarity	NPC471412
0.7475	Intermediate Similarity	NPC212486
0.7474	Intermediate Similarity	NPC47958
0.7474	Intermediate Similarity	NPC304509
0.7474	Intermediate Similarity	NPC110405
0.7474	Intermediate Similarity	NPC149725
0.7453	Intermediate Similarity	NPC133422
0.7453	Intermediate Similarity	NPC475510
0.7453	Intermediate Similarity	NPC475587
0.7453	Intermediate Similarity	NPC110496
0.7453	Intermediate Similarity	NPC166993
0.7453	Intermediate Similarity	NPC67321
0.7453	Intermediate Similarity	NPC187435
0.7451	Intermediate Similarity	NPC162459
0.7451	Intermediate Similarity	NPC89099
0.7451	Intermediate Similarity	NPC28864
0.7451	Intermediate Similarity	NPC38471
0.7451	Intermediate Similarity	NPC20479
0.7451	Intermediate Similarity	NPC98837
0.7451	Intermediate Similarity	NPC38296
0.7451	Intermediate Similarity	NPC471932
0.7449	Intermediate Similarity	NPC251385
0.7449	Intermediate Similarity	NPC158488
0.7449	Intermediate Similarity	NPC153853
0.7449	Intermediate Similarity	NPC49342
0.7434	Intermediate Similarity	NPC317635
0.7434	Intermediate Similarity	NPC329008
0.7431	Intermediate Similarity	NPC476964
0.7431	Intermediate Similarity	NPC472002
0.7431	Intermediate Similarity	NPC470468
0.7429	Intermediate Similarity	NPC258532
0.7429	Intermediate Similarity	NPC328737
0.7426	Intermediate Similarity	NPC307164
0.7426	Intermediate Similarity	NPC29952
0.7423	Intermediate Similarity	NPC215831
0.7419	Intermediate Similarity	NPC475951
0.7419	Intermediate Similarity	NPC47635
0.7419	Intermediate Similarity	NPC207188
0.7414	Intermediate Similarity	NPC293112
0.7414	Intermediate Similarity	NPC473635
0.7411	Intermediate Similarity	NPC159928
0.7411	Intermediate Similarity	NPC108581
0.7411	Intermediate Similarity	NPC478206
0.7411	Intermediate Similarity	NPC478205
0.7407	Intermediate Similarity	NPC472215
0.7407	Intermediate Similarity	NPC5103
0.7407	Intermediate Similarity	NPC472214
0.7404	Intermediate Similarity	NPC214946
0.7404	Intermediate Similarity	NPC246736
0.7404	Intermediate Similarity	NPC76866
0.7404	Intermediate Similarity	NPC148628
0.7404	Intermediate Similarity	NPC304832
0.7404	Intermediate Similarity	NPC476081
0.7404	Intermediate Similarity	NPC286519
0.7404	Intermediate Similarity	NPC170615
0.7404	Intermediate Similarity	NPC162973
0.7404	Intermediate Similarity	NPC88203
0.74	Intermediate Similarity	NPC473316

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	239
0.1-0.2	2184
0.2-0.3	3954
0.3-0.4	1825
0.4-0.5	582
0.5-0.6	256
0.6-0.7	104
0.7-0.8	6
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7849	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7358	Intermediate Similarity	NPD6008	Approved
0.7315	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1695	Approved
0.6952	Remote Similarity	NPD4225	Approved
0.6939	Remote Similarity	NPD1694	Approved
0.6887	Remote Similarity	NPD6648	Approved
0.687	Remote Similarity	NPD7115	Discovery
0.6822	Remote Similarity	NPD5344	Discontinued
0.6636	Remote Similarity	NPD7638	Approved
0.6634	Remote Similarity	NPD3573	Approved
0.6633	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7639	Approved
0.6574	Remote Similarity	NPD7640	Approved
0.6514	Remote Similarity	NPD1700	Approved
0.65	Remote Similarity	NPD6921	Approved
0.6466	Remote Similarity	NPD4632	Approved
0.6466	Remote Similarity	NPD8133	Approved
0.646	Remote Similarity	NPD6686	Approved
0.6442	Remote Similarity	NPD6698	Approved
0.6442	Remote Similarity	NPD46	Approved
0.6423	Remote Similarity	NPD7507	Approved
0.6417	Remote Similarity	NPD6319	Approved
0.64	Remote Similarity	NPD7319	Approved
0.6381	Remote Similarity	NPD8035	Phase 2
0.6381	Remote Similarity	NPD8034	Phase 2
0.6379	Remote Similarity	NPD8297	Approved
0.6372	Remote Similarity	NPD5697	Approved
0.6355	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6341	Remote Similarity	NPD7492	Approved
0.6316	Remote Similarity	NPD6881	Approved
0.6316	Remote Similarity	NPD6899	Approved
0.6303	Remote Similarity	NPD6009	Approved
0.6293	Remote Similarity	NPD6649	Approved
0.6293	Remote Similarity	NPD6650	Approved
0.629	Remote Similarity	NPD6616	Approved
0.6283	Remote Similarity	NPD6675	Approved
0.6283	Remote Similarity	NPD7128	Approved
0.6283	Remote Similarity	NPD5739	Approved
0.6283	Remote Similarity	NPD6402	Approved
0.6281	Remote Similarity	NPD6054	Approved
0.6275	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6001	Approved
0.6262	Remote Similarity	NPD7900	Approved
0.6261	Remote Similarity	NPD6013	Approved
0.6261	Remote Similarity	NPD6372	Approved
0.6261	Remote Similarity	NPD6373	Approved
0.6261	Remote Similarity	NPD6012	Approved
0.6261	Remote Similarity	NPD6014	Approved
0.626	Remote Similarity	NPD7604	Phase 2
0.624	Remote Similarity	NPD7078	Approved
0.6239	Remote Similarity	NPD6053	Discontinued
0.623	Remote Similarity	NPD8516	Approved
0.623	Remote Similarity	NPD8515	Approved
0.623	Remote Similarity	NPD6016	Approved
0.623	Remote Similarity	NPD8513	Phase 3
0.623	Remote Similarity	NPD6015	Approved
0.623	Remote Similarity	NPD5983	Phase 2
0.623	Remote Similarity	NPD8517	Approved
0.6228	Remote Similarity	NPD5701	Approved
0.6228	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7334	Approved
0.6214	Remote Similarity	NPD5330	Approved
0.6214	Remote Similarity	NPD7146	Approved
0.6214	Remote Similarity	NPD6684	Approved
0.6214	Remote Similarity	NPD6409	Approved
0.6214	Remote Similarity	NPD7521	Approved
0.6207	Remote Similarity	NPD6883	Approved
0.6207	Remote Similarity	NPD7290	Approved
0.6207	Remote Similarity	NPD7102	Approved
0.6204	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.62	Remote Similarity	NPD1779	Approved
0.62	Remote Similarity	NPD1780	Approved
0.619	Remote Similarity	NPD7736	Approved
0.6179	Remote Similarity	NPD6370	Approved
0.6179	Remote Similarity	NPD5988	Approved
0.6174	Remote Similarity	NPD7320	Approved
0.6174	Remote Similarity	NPD6011	Approved
0.6168	Remote Similarity	NPD5779	Approved
0.6168	Remote Similarity	NPD5778	Approved
0.6168	Remote Similarity	NPD6399	Phase 3
0.6161	Remote Similarity	NPD7632	Discontinued
0.6154	Remote Similarity	NPD6869	Approved
0.6154	Remote Similarity	NPD8130	Phase 1
0.6154	Remote Similarity	NPD6847	Approved
0.6154	Remote Similarity	NPD6617	Approved
0.6148	Remote Similarity	NPD6059	Approved
0.6121	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD8293	Discontinued
0.6111	Remote Similarity	NPD7748	Approved
0.6102	Remote Similarity	NPD6882	Approved
0.6095	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD6903	Approved
0.6091	Remote Similarity	NPD7902	Approved
0.6075	Remote Similarity	NPD5693	Phase 1
0.6075	Remote Similarity	NPD6079	Approved
0.6068	Remote Similarity	NPD6371	Approved
0.6066	Remote Similarity	NPD7516	Approved
0.6058	Remote Similarity	NPD3618	Phase 1
0.6038	Remote Similarity	NPD5328	Approved
0.6033	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6032	Remote Similarity	NPD6336	Discontinued
0.6018	Remote Similarity	NPD5211	Phase 2
0.6	Remote Similarity	NPD8328	Phase 3
0.5984	Remote Similarity	NPD8074	Phase 3
0.5984	Remote Similarity	NPD7328	Approved
0.5984	Remote Similarity	NPD7327	Approved
0.5982	Remote Similarity	NPD5285	Approved
0.5982	Remote Similarity	NPD5286	Approved
0.5982	Remote Similarity	NPD4696	Approved
0.5981	Remote Similarity	NPD7838	Discovery
0.5981	Remote Similarity	NPD3168	Discontinued
0.595	Remote Similarity	NPD6274	Approved
0.5946	Remote Similarity	NPD4755	Approved
0.5943	Remote Similarity	NPD6672	Approved
0.5943	Remote Similarity	NPD5737	Approved
0.5932	Remote Similarity	NPD4634	Approved
0.5926	Remote Similarity	NPD7515	Phase 2
0.5913	Remote Similarity	NPD5141	Approved
0.5893	Remote Similarity	NPD5696	Approved
0.5889	Remote Similarity	NPD1145	Discontinued
0.5888	Remote Similarity	NPD6101	Approved
0.5888	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5877	Remote Similarity	NPD5225	Approved
0.5877	Remote Similarity	NPD4633	Approved
0.5877	Remote Similarity	NPD5224	Approved
0.5877	Remote Similarity	NPD5226	Approved
0.5856	Remote Similarity	NPD5221	Approved
0.5856	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4697	Phase 3
0.5856	Remote Similarity	NPD5222	Approved
0.5841	Remote Similarity	NPD4700	Approved
0.584	Remote Similarity	NPD8335	Approved
0.584	Remote Similarity	NPD8380	Approved
0.584	Remote Similarity	NPD8378	Approved
0.584	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.584	Remote Similarity	NPD8296	Approved
0.584	Remote Similarity	NPD8379	Approved
0.584	Remote Similarity	NPD8033	Approved
0.5833	Remote Similarity	NPD5207	Approved
0.5826	Remote Similarity	NPD5174	Approved
0.5826	Remote Similarity	NPD5175	Approved
0.5825	Remote Similarity	NPD3667	Approved
0.5812	Remote Similarity	NPD6412	Phase 2
0.5806	Remote Similarity	NPD7101	Approved
0.5806	Remote Similarity	NPD7100	Approved
0.5804	Remote Similarity	NPD6083	Phase 2
0.5804	Remote Similarity	NPD5173	Approved
0.5804	Remote Similarity	NPD6084	Phase 2
0.5802	Remote Similarity	NPD7260	Phase 2
0.5794	Remote Similarity	NPD5208	Approved
0.5789	Remote Similarity	NPD4159	Approved
0.5789	Remote Similarity	NPD5223	Approved
0.578	Remote Similarity	NPD7983	Approved
0.578	Remote Similarity	NPD6411	Approved
0.5772	Remote Similarity	NPD6317	Approved
0.5769	Remote Similarity	NPD4788	Approved
0.5766	Remote Similarity	NPD5695	Phase 3
0.576	Remote Similarity	NPD8294	Approved
0.576	Remote Similarity	NPD8377	Approved
0.5758	Remote Similarity	NPD6845	Suspended
0.5758	Remote Similarity	NPD3703	Phase 2
0.5755	Remote Similarity	NPD6098	Approved
0.5752	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5743	Remote Similarity	NPD6115	Approved
0.5743	Remote Similarity	NPD6118	Approved
0.5743	Remote Similarity	NPD6114	Approved
0.5743	Remote Similarity	NPD6697	Approved
0.5741	Remote Similarity	NPD6673	Approved
0.5741	Remote Similarity	NPD6904	Approved
0.5741	Remote Similarity	NPD6080	Approved
0.5741	Remote Similarity	NPD6051	Approved
0.5739	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD4202	Approved
0.5726	Remote Similarity	NPD6335	Approved
0.5726	Remote Similarity	NPD6313	Approved
0.5726	Remote Similarity	NPD6314	Approved
0.5714	Remote Similarity	NPD3668	Phase 3
0.5714	Remote Similarity	NPD4786	Approved
0.5714	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7503	Approved
0.5701	Remote Similarity	NPD7524	Approved
0.5692	Remote Similarity	NPD6033	Approved
0.5691	Remote Similarity	NPD6868	Approved
0.5676	Remote Similarity	NPD5282	Discontinued
0.5638	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD7637	Suspended
0.563	Remote Similarity	NPD4729	Approved
0.563	Remote Similarity	NPD4730	Approved
0.563	Remote Similarity	NPD5128	Approved
0.5612	Remote Similarity	NPD5777	Approved
0.5607	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.56	Remote Similarity	NPD3702	Approved

Bioactivity similarity: Similar Natural Products in NPASS

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