NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.13
Volume:	272.449
LogP:	2.879
LogD:	2.469
LogS:	-4.578
# Rotatable Bonds:	0
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.387
Synthetic Accessibility Score:	5.838
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.663
MDCK Permeability:	5.26251460541971e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.044

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.369
Plasma Protein Binding (PPB):	68.14282989501953%
Volume Distribution (VD):	1.274
Pgp-substrate:	22.461769104003906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.424
CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.163
CYP2C9-substrate:	0.056
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.741
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.319

ADMET: Excretion

Clearance (CL):	10.364
Half-life (T1/2):	0.366

ADMET: Toxicity

hERG Blockers:	0.618
Human Hepatotoxicity (H-HT):	0.978
Drug-inuced Liver Injury (DILI):	0.927
AMES Toxicity:	0.934
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.943
Skin Sensitization:	0.872
Carcinogencity:	0.934
Eye Corrosion:	0.931
Eye Irritation:	0.932
Respiratory Toxicity:	0.988

Download Data

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

Natural Product: NPC148872

Natural Product ID:	NPC148872
*Common Name:**	Artemisitene
IUPAC Name:	n.a.
Synonyms:	Artemisitene
Standard InCHIKey:	IGEBZMMCKFUABB-KPHNHPKPSA-N
Standard InCHI:	InChI=1S/C15H20O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8,10-11,13H,2,4-7H2,1,3H3/t8-,10+,11+,13-,14-,15-/m1/s1
SMILES:	O=C1O[C@@H]2O[C@@]3(C)CC[C@@H]4[C@]2([C@H](C1=C)CC[C@H]4C)OO3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL526138
PubChem CID:	11000442
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
IC50	10
Others	3

Activity Type	# Activity
NON-MOLECULAR	7
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.0053	ug.mL-1	PMID[513891]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	2800.0	nM	PMID[513891]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.00744	ug.mL-1	PMID[513891]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	7800.0	nM	PMID[513891]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Log RA	=	-0.89	n.a.	PMID[513892]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1700.0	nM	PMID[513893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	10000.0	nM	PMID[513893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	11300.0	nM	PMID[513893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6800.0	nM	PMID[513893]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC80	=	16.0	uM	PMID[513893]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	0.045	ug.mL-1	PMID[513894]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6800.0	nM	PMID[513895]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC80	=	16.0	uM	PMID[513895]

☑ 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 NPC148872 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	307
0.1-0.2	2399
0.2-0.3	6327
0.3-0.4	13247
0.4-0.5	10507
0.5-0.6	7228
0.6-0.7	2638
0.7-0.8	39
0.8-0.85	0
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8427	Intermediate Similarity	NPC285480
0.8427	Intermediate Similarity	NPC30443
0.8427	Intermediate Similarity	NPC45256
0.8427	Intermediate Similarity	NPC260977
0.7912	Intermediate Similarity	NPC60568
0.7885	Intermediate Similarity	NPC41681
0.76	Intermediate Similarity	NPC474841
0.76	Intermediate Similarity	NPC66581
0.76	Intermediate Similarity	NPC473434
0.76	Intermediate Similarity	NPC471446
0.76	Intermediate Similarity	NPC476722
0.7526	Intermediate Similarity	NPC175293
0.7525	Intermediate Similarity	NPC167893
0.75	Intermediate Similarity	NPC112457
0.7475	Intermediate Similarity	NPC475776
0.7474	Intermediate Similarity	NPC67158
0.7474	Intermediate Similarity	NPC30102
0.7474	Intermediate Similarity	NPC128816
0.7455	Intermediate Similarity	NPC222834
0.74	Intermediate Similarity	NPC470373
0.74	Intermediate Similarity	NPC165180
0.74	Intermediate Similarity	NPC470379
0.7379	Intermediate Similarity	NPC474921
0.7353	Intermediate Similarity	NPC90014
0.7353	Intermediate Similarity	NPC56369
0.7304	Intermediate Similarity	NPC48692
0.73	Intermediate Similarity	NPC328935
0.73	Intermediate Similarity	NPC327183
0.7282	Intermediate Similarity	NPC228766
0.7282	Intermediate Similarity	NPC473964
0.7282	Intermediate Similarity	NPC165528
0.7282	Intermediate Similarity	NPC93245
0.7273	Intermediate Similarity	NPC475501
0.7273	Intermediate Similarity	NPC50847
0.7273	Intermediate Similarity	NPC83005
0.7263	Intermediate Similarity	NPC47635
0.7257	Intermediate Similarity	NPC229752
0.7257	Intermediate Similarity	NPC88945
0.7255	Intermediate Similarity	NPC469596
0.7255	Intermediate Similarity	NPC225474
0.7255	Intermediate Similarity	NPC71589
0.7255	Intermediate Similarity	NPC148000
0.7255	Intermediate Similarity	NPC41649
0.7245	Intermediate Similarity	NPC185638
0.7232	Intermediate Similarity	NPC132668
0.7232	Intermediate Similarity	NPC311592
0.7232	Intermediate Similarity	NPC75167
0.7232	Intermediate Similarity	NPC157441
0.7228	Intermediate Similarity	NPC65513
0.7222	Intermediate Similarity	NPC56656
0.7222	Intermediate Similarity	NPC103172
0.7222	Intermediate Similarity	NPC164600
0.7212	Intermediate Similarity	NPC473963
0.7207	Intermediate Similarity	NPC63244
0.72	Intermediate Similarity	NPC116620
0.7196	Intermediate Similarity	NPC475928
0.7196	Intermediate Similarity	NPC61442
0.7193	Intermediate Similarity	NPC78836
0.7193	Intermediate Similarity	NPC474483
0.7188	Intermediate Similarity	NPC226988
0.7184	Intermediate Similarity	NPC259042
0.7184	Intermediate Similarity	NPC157686
0.7182	Intermediate Similarity	NPC102741
0.717	Intermediate Similarity	NPC111292
0.717	Intermediate Similarity	NPC475958
0.7168	Intermediate Similarity	NPC181145
0.7158	Intermediate Similarity	NPC474981
0.7156	Intermediate Similarity	NPC148270
0.7156	Intermediate Similarity	NPC471474
0.7156	Intermediate Similarity	NPC80338
0.7156	Intermediate Similarity	NPC293512
0.7156	Intermediate Similarity	NPC197813
0.7155	Intermediate Similarity	NPC151616
0.7143	Intermediate Similarity	NPC222307
0.7143	Intermediate Similarity	NPC471244
0.7143	Intermediate Similarity	NPC49833
0.7143	Intermediate Similarity	NPC145625
0.7143	Intermediate Similarity	NPC157929
0.7143	Intermediate Similarity	NPC249171
0.7143	Intermediate Similarity	NPC12046
0.7143	Intermediate Similarity	NPC194951
0.713	Intermediate Similarity	NPC476764
0.713	Intermediate Similarity	NPC244247
0.713	Intermediate Similarity	NPC476763
0.7117	Intermediate Similarity	NPC471476
0.7117	Intermediate Similarity	NPC253906
0.7117	Intermediate Similarity	NPC235014
0.7115	Intermediate Similarity	NPC317573
0.7113	Intermediate Similarity	NPC257358
0.7113	Intermediate Similarity	NPC474472
0.7111	Intermediate Similarity	NPC29005
0.7111	Intermediate Similarity	NPC51956
0.7111	Intermediate Similarity	NPC5209
0.7105	Intermediate Similarity	NPC471816
0.7103	Intermediate Similarity	NPC80144
0.7103	Intermediate Similarity	NPC164551
0.7103	Intermediate Similarity	NPC106668
0.7094	Intermediate Similarity	NPC204731
0.7094	Intermediate Similarity	NPC476204
0.7094	Intermediate Similarity	NPC170084
0.7091	Intermediate Similarity	NPC232133
0.7091	Intermediate Similarity	NPC177524
0.7091	Intermediate Similarity	NPC471094
0.7091	Intermediate Similarity	NPC219900
0.7091	Intermediate Similarity	NPC392
0.7091	Intermediate Similarity	NPC469984
0.7091	Intermediate Similarity	NPC473410
0.7087	Intermediate Similarity	NPC24861
0.7087	Intermediate Similarity	NPC476716
0.7083	Intermediate Similarity	NPC38642
0.708	Intermediate Similarity	NPC94141
0.708	Intermediate Similarity	NPC189884
0.708	Intermediate Similarity	NPC138334
0.708	Intermediate Similarity	NPC204458
0.708	Intermediate Similarity	NPC47063
0.7075	Intermediate Similarity	NPC476933
0.7071	Intermediate Similarity	NPC244174
0.7071	Intermediate Similarity	NPC9231
0.7071	Intermediate Similarity	NPC85698
0.7069	Intermediate Similarity	NPC122971
0.7064	Intermediate Similarity	NPC476760
0.7064	Intermediate Similarity	NPC476762
0.7064	Intermediate Similarity	NPC476761
0.7064	Intermediate Similarity	NPC170432
0.7064	Intermediate Similarity	NPC469401
0.7059	Intermediate Similarity	NPC474631
0.7059	Intermediate Similarity	NPC476934
0.7059	Intermediate Similarity	NPC329952
0.7054	Intermediate Similarity	NPC122339
0.7054	Intermediate Similarity	NPC274833
0.7054	Intermediate Similarity	NPC329953
0.7054	Intermediate Similarity	NPC471251
0.7054	Intermediate Similarity	NPC213320
0.7053	Intermediate Similarity	NPC323472
0.7048	Intermediate Similarity	NPC204054
0.7048	Intermediate Similarity	NPC257726
0.7048	Intermediate Similarity	NPC474395
0.7048	Intermediate Similarity	NPC304445
0.7048	Intermediate Similarity	NPC111348
0.7048	Intermediate Similarity	NPC136781
0.7048	Intermediate Similarity	NPC236580
0.7043	Intermediate Similarity	NPC473304
0.7043	Intermediate Similarity	NPC23046
0.7043	Intermediate Similarity	NPC13713
0.7041	Intermediate Similarity	NPC470011
0.7037	Intermediate Similarity	NPC27687
0.7037	Intermediate Similarity	NPC254202
0.7037	Intermediate Similarity	NPC37240
0.7037	Intermediate Similarity	NPC99510
0.7037	Intermediate Similarity	NPC72842
0.7037	Intermediate Similarity	NPC473148
0.7027	Intermediate Similarity	NPC8431
0.7027	Intermediate Similarity	NPC131903
0.7027	Intermediate Similarity	NPC471250
0.7027	Intermediate Similarity	NPC274827
0.7027	Intermediate Similarity	NPC469370
0.7027	Intermediate Similarity	NPC469744
0.7027	Intermediate Similarity	NPC469983
0.7025	Intermediate Similarity	NPC270109
0.7019	Intermediate Similarity	NPC217329
0.7018	Intermediate Similarity	NPC17165
0.7009	Intermediate Similarity	NPC67296
0.7009	Intermediate Similarity	NPC242666
0.7009	Intermediate Similarity	NPC476150
0.7009	Intermediate Similarity	NPC476127
0.7	Intermediate Similarity	NPC74139
0.7	Intermediate Similarity	NPC186054
0.7	Intermediate Similarity	NPC180744
0.7	Intermediate Similarity	NPC476932
0.7	Intermediate Similarity	NPC305029
0.7	Intermediate Similarity	NPC96333
0.7	Intermediate Similarity	NPC469746
0.7	Intermediate Similarity	NPC5130
0.7	Intermediate Similarity	NPC88833
0.6991	Remote Similarity	NPC473397
0.6991	Remote Similarity	NPC174836
0.6991	Remote Similarity	NPC472719
0.6991	Remote Similarity	NPC256798
0.6991	Remote Similarity	NPC473352
0.6991	Remote Similarity	NPC474927
0.6991	Remote Similarity	NPC207845
0.6991	Remote Similarity	NPC128925
0.6991	Remote Similarity	NPC471245
0.6991	Remote Similarity	NPC470543
0.6991	Remote Similarity	NPC37739
0.6991	Remote Similarity	NPC265391
0.6991	Remote Similarity	NPC473303
0.6991	Remote Similarity	NPC46388
0.699	Remote Similarity	NPC147272
0.699	Remote Similarity	NPC474835
0.699	Remote Similarity	NPC163902
0.6983	Remote Similarity	NPC234522
0.6981	Remote Similarity	NPC476807
0.6981	Remote Similarity	NPC216478
0.6981	Remote Similarity	NPC476806
0.6981	Remote Similarity	NPC279561
0.6972	Remote Similarity	NPC474898
0.6972	Remote Similarity	NPC477127
0.6972	Remote Similarity	NPC202793
0.6972	Remote Similarity	NPC283850

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 NPC148872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	315
0.1-0.2	2562
0.2-0.3	3864
0.3-0.4	1712
0.4-0.5	450
0.5-0.6	211
0.6-0.7	26
0.7-0.8	8
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8427	Intermediate Similarity	NPD1780	Approved
0.8427	Intermediate Similarity	NPD1779	Approved
0.7474	Intermediate Similarity	NPD3669	Approved
0.7474	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD2254	Approved
0.7111	Intermediate Similarity	NPD2687	Approved
0.7111	Intermediate Similarity	NPD2686	Approved
0.7091	Intermediate Similarity	NPD6686	Approved
0.708	Intermediate Similarity	NPD8133	Approved
0.6882	Remote Similarity	NPD1810	Approved
0.6882	Remote Similarity	NPD1811	Approved
0.6721	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD8513	Phase 3
0.6667	Remote Similarity	NPD8516	Approved
0.6667	Remote Similarity	NPD8517	Approved
0.6667	Remote Similarity	NPD8515	Approved
0.6637	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.661	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.656	Remote Similarity	NPD7319	Approved
0.6557	Remote Similarity	NPD8328	Phase 3
0.6549	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6008	Approved
0.6404	Remote Similarity	NPD6412	Phase 2
0.6393	Remote Similarity	NPD8033	Approved
0.6381	Remote Similarity	NPD1695	Approved
0.6379	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD3573	Approved
0.6337	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6009	Approved
0.6325	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD8294	Approved
0.6311	Remote Similarity	NPD8377	Approved
0.6311	Remote Similarity	NPD1694	Approved
0.6293	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6281	Remote Similarity	NPD7328	Approved
0.6281	Remote Similarity	NPD7327	Approved
0.6271	Remote Similarity	NPD6053	Discontinued
0.626	Remote Similarity	NPD7503	Approved
0.626	Remote Similarity	NPD8296	Approved
0.626	Remote Similarity	NPD8378	Approved
0.626	Remote Similarity	NPD8335	Approved
0.626	Remote Similarity	NPD8379	Approved
0.626	Remote Similarity	NPD8380	Approved
0.623	Remote Similarity	NPD7516	Approved
0.622	Remote Similarity	NPD7736	Approved
0.6216	Remote Similarity	NPD7638	Approved
0.621	Remote Similarity	NPD6370	Approved
0.6168	Remote Similarity	NPD46	Approved
0.6168	Remote Similarity	NPD6698	Approved
0.6161	Remote Similarity	NPD7640	Approved
0.6161	Remote Similarity	NPD7639	Approved
0.6147	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7900	Approved
0.6142	Remote Similarity	NPD8074	Phase 3
0.6142	Remote Similarity	NPD8293	Discontinued
0.6111	Remote Similarity	NPD7492	Approved
0.6111	Remote Similarity	NPD8035	Phase 2
0.6111	Remote Similarity	NPD8034	Phase 2
0.6083	Remote Similarity	NPD4632	Approved
0.6071	Remote Similarity	NPD4225	Approved
0.6066	Remote Similarity	NPD7115	Discovery
0.6063	Remote Similarity	NPD6616	Approved
0.6048	Remote Similarity	NPD6054	Approved
0.6018	Remote Similarity	NPD6648	Approved
0.6016	Remote Similarity	NPD7078	Approved
0.6	Remote Similarity	NPD6015	Approved
0.6	Remote Similarity	NPD6016	Approved
0.6	Remote Similarity	NPD6882	Approved
0.6	Remote Similarity	NPD6921	Approved
0.5983	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5982	Remote Similarity	NPD7902	Approved
0.5969	Remote Similarity	NPD8336	Approved
0.5969	Remote Similarity	NPD8337	Approved
0.5965	Remote Similarity	NPD5344	Discontinued
0.5963	Remote Similarity	NPD5693	Phase 1
0.5952	Remote Similarity	NPD5988	Approved
0.5946	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.592	Remote Similarity	NPD6059	Approved
0.592	Remote Similarity	NPD6319	Approved
0.5909	Remote Similarity	NPD6399	Phase 3
0.5873	Remote Similarity	NPD8269	Approved
0.5873	Remote Similarity	NPD8267	Approved
0.5873	Remote Similarity	NPD5983	Phase 2
0.5873	Remote Similarity	NPD8266	Approved
0.5873	Remote Similarity	NPD8268	Approved
0.5868	Remote Similarity	NPD8297	Approved
0.5856	Remote Similarity	NPD7748	Approved
0.5847	Remote Similarity	NPD5697	Approved
0.5833	Remote Similarity	NPD7260	Phase 2
0.5833	Remote Similarity	NPD5737	Approved
0.5833	Remote Similarity	NPD6672	Approved
0.5833	Remote Similarity	NPD6371	Approved
0.5814	Remote Similarity	NPD8451	Approved
0.5804	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD6899	Approved
0.5798	Remote Similarity	NPD6881	Approved
0.5798	Remote Similarity	NPD6011	Approved
0.5794	Remote Similarity	NPD6409	Approved
0.5794	Remote Similarity	NPD7146	Approved
0.5794	Remote Similarity	NPD7334	Approved
0.5794	Remote Similarity	NPD6684	Approved
0.5794	Remote Similarity	NPD5330	Approved
0.5794	Remote Similarity	NPD7521	Approved
0.5785	Remote Similarity	NPD6649	Approved
0.5785	Remote Similarity	NPD6650	Approved
0.5781	Remote Similarity	NPD7604	Phase 2
0.5781	Remote Similarity	NPD7830	Approved
0.5781	Remote Similarity	NPD7829	Approved
0.5781	Remote Similarity	NPD6067	Discontinued
0.578	Remote Similarity	NPD6101	Approved
0.578	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD7632	Discontinued
0.5769	Remote Similarity	NPD8448	Approved
0.5766	Remote Similarity	NPD5778	Approved
0.5766	Remote Similarity	NPD5779	Approved
0.5763	Remote Similarity	NPD5739	Approved
0.5763	Remote Similarity	NPD7128	Approved
0.5763	Remote Similarity	NPD6402	Approved
0.5763	Remote Similarity	NPD6675	Approved
0.5761	Remote Similarity	NPD1145	Discontinued
0.5758	Remote Similarity	NPD8391	Approved
0.5758	Remote Similarity	NPD8390	Approved
0.5758	Remote Similarity	NPD8392	Approved
0.575	Remote Similarity	NPD6014	Approved
0.575	Remote Similarity	NPD6372	Approved
0.575	Remote Similarity	NPD6373	Approved
0.575	Remote Similarity	NPD6013	Approved
0.575	Remote Similarity	NPD6012	Approved
0.5714	Remote Similarity	NPD5701	Approved
0.5714	Remote Similarity	NPD6001	Approved
0.5702	Remote Similarity	NPD6883	Approved
0.5702	Remote Similarity	NPD7290	Approved
0.5702	Remote Similarity	NPD7102	Approved
0.5701	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD6336	Discontinued
0.5688	Remote Similarity	NPD6903	Approved
0.5688	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6411	Approved
0.5676	Remote Similarity	NPD7515	Phase 2
0.5672	Remote Similarity	NPD6845	Suspended
0.5672	Remote Similarity	NPD8338	Approved
0.5667	Remote Similarity	NPD7320	Approved
0.5664	Remote Similarity	NPD5695	Phase 3
0.5659	Remote Similarity	NPD7642	Approved
0.5656	Remote Similarity	NPD6869	Approved
0.5656	Remote Similarity	NPD6847	Approved
0.5656	Remote Similarity	NPD6617	Approved
0.5656	Remote Similarity	NPD8130	Phase 1
0.5652	Remote Similarity	NPD5696	Approved
0.5636	Remote Similarity	NPD6904	Approved
0.5636	Remote Similarity	NPD6080	Approved
0.5636	Remote Similarity	NPD6673	Approved
0.5635	Remote Similarity	NPD7641	Discontinued
0.5615	Remote Similarity	NPD8299	Approved
0.5615	Remote Similarity	NPD8342	Approved
0.5615	Remote Similarity	NPD8341	Approved
0.5615	Remote Similarity	NPD8340	Approved
0.5606	Remote Similarity	NPD6033	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