NPASS Compound

Structure

NPC19273 OpenBabel07101719132D 46 52 0 0 1 0 0 0 0 0999 V2000 -2.5981 -5.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0981 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5981 2.6962 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 -7.5981 2.6962 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 -9.0981 1.8301 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 -3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 -1.6340 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 -3.0981 -1.6340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 0.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5981 -0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 1.8301 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 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5981 0.9641 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 -4.5981 0.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 0.9641 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 -5.5981 -0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0981 1.8301 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5981 0.9641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0981 0.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0981 0.0981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0981 1.8301 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0981 -1.6340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 2.6962 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 -1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 0.0981 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 1 16 1 0 0 0 0 3 5 2 0 0 0 0 3 7 1 0 0 0 0 4 6 2 0 0 0 0 4 8 1 0 0 0 0 5 18 1 0 0 0 0 6 19 1 0 0 0 0 7 22 2 0 0 0 0 8 23 2 0 0 0 0 9 11 1 0 0 0 0 9 16 1 0 0 0 0 10 12 2 0 0 0 0 10 17 1 0 0 0 0 11 36 1 0 0 0 0 12 36 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 14 17 2 0 0 0 0 14 24 1 0 0 0 0 15 20 2 0 0 0 0 15 25 1 0 0 0 0 17 28 1 0 0 0 0 18 29 1 0 0 0 0 18 32 2 0 0 0 0 19 30 1 0 0 0 0 19 33 2 0 0 0 0 20 21 1 0 0 0 0 20 31 1 0 0 0 0 21 36 1 6 0 0 0 22 32 1 0 0 0 0 22 37 1 0 0 0 0 23 33 1 0 0 0 0 23 38 1 0 0 0 0 24 26 2 0 0 0 0 24 39 1 0 0 0 0 25 27 2 0 0 0 0 25 40 1 0 0 0 0 26 29 1 0 0 0 0 26 34 1 0 0 0 0 27 30 1 0 0 0 0 27 35 1 0 0 0 0 28 34 2 0 0 0 0 28 41 1 0 0 0 0 29 42 2 0 0 0 0 30 43 2 0 0 0 0 31 35 2 0 0 0 0 31 44 1 0 0 0 0 32 45 1 0 0 0 0 33 46 1 0 0 0 0 34 45 1 0 0 0 0 35 46 1 0 0 0 0 36 2 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	620.17
Volume:	617.036
LogP:	6.464
LogD:	2.695
LogS:	-3.974
# Rotatable Bonds:	3
TPSA:	181.8
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.069
Synthetic Accessibility Score:	4.52
Fsp3:	0.167
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.573
MDCK Permeability:	8.814430657366756e-06
Pgp-inhibitor:	0.058
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.88
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001
Plasma Protein Binding (PPB):	89.87665557861328%
Volume Distribution (VD):	0.422
Pgp-substrate:	21.954240798950195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.419
CYP1A2-substrate:	0.196
CYP2C19-inhibitor:	0.365
CYP2C19-substrate:	0.047
CYP2C9-inhibitor:	0.654
CYP2C9-substrate:	0.61
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.13
CYP3A4-inhibitor:	0.101
CYP3A4-substrate:	0.064

ADMET: Excretion

Clearance (CL):	2.145
Half-life (T1/2):	0.199

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.904
Drug-inuced Liver Injury (DILI):	0.996
AMES Toxicity:	0.736
Rat Oral Acute Toxicity:	0.753
Maximum Recommended Daily Dose:	0.907
Skin Sensitization:	0.897
Carcinogencity:	0.474
Eye Corrosion:	0.003
Eye Irritation:	0.888
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC19273

Natural Product ID:	NPC19273
*Common Name:**	Garcivilin C
IUPAC Name:	3-[(E)-2-[(1S,2R)-1,4-dimethyl-2-(1,4,5-trihydroxy-9-oxoxanthen-3-yl)cyclohex-3-en-1-yl]ethenyl]-1,4,5-trihydroxyxanthen-9-one
Synonyms:	Garcivilin C
Standard InCHIKey:	XYRCPMXSIHHGSO-VDSQSLJXSA-N
Standard InCHI:	InChI=1S/C36H28O10/c1-16-9-11-36(2,12-10-17-14-24(39)26-29(42)18-5-3-7-22(37)32(18)45-34(26)28(17)41)21(13-16)20-15-25(40)27-30(43)19-6-4-8-23(38)33(19)46-35(27)31(20)44/h3-8,10,12-15,21,37-41,44H,9,11H2,1-2H3/b12-10+/t21-,36-/m0/s1
SMILES:	CC1=C[C@@H](c2cc(c3c(=O)c4cccc(c4oc3c2O)O)O)[C@@](C)(CC1)/C=C/c1cc(c2c(=O)c3cccc(c3oc2c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499445
PubChem CID:	10031809
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/S0040-4020(01)89039-6]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	root bark	n.a.	n.a.	PMID[16562837]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21028890]
NPO5638	Garcinia livingstonei	Species	Clusiaceae	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	5

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT171	Cell Line	MRC5	Homo sapiens	IC50	=	52300.0	nM	PMID[547539]
NPT471	Organism	Trypanosoma brucei brucei	Trypanosoma brucei brucei	IC50	=	7700.0	nM	PMID[547539]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	39200.0	nM	PMID[547539]
NPT1021	Organism	Leishmania infantum	Leishmania infantum	IC50	>	64000.0	nM	PMID[547539]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	64000.0	nM	PMID[547539]

☑ 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 NPC19273 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	500
0.1-0.2	1930
0.2-0.3	4182
0.3-0.4	10549
0.4-0.5	7969
0.5-0.6	4146
0.6-0.7	5998
0.7-0.8	5200
0.8-0.85	1472
0.85-0.9	734
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC17884
0.9119	High Similarity	NPC75069
0.8976	High Similarity	NPC272560
0.8947	High Similarity	NPC120102
0.8922	High Similarity	NPC14662
0.8916	High Similarity	NPC477840
0.8902	High Similarity	NPC188967
0.8896	High Similarity	NPC185526
0.8855	High Similarity	NPC272064
0.8848	High Similarity	NPC34089
0.8848	High Similarity	NPC196179
0.8841	High Similarity	NPC154304
0.8841	High Similarity	NPC287458
0.8841	High Similarity	NPC190487
0.8837	High Similarity	NPC185275
0.8837	High Similarity	NPC324742
0.8812	High Similarity	NPC294502
0.8812	High Similarity	NPC200221
0.881	High Similarity	NPC243877
0.8795	High Similarity	NPC477841
0.8788	High Similarity	NPC98892
0.8779	High Similarity	NPC265380
0.8765	High Similarity	NPC174700
0.8757	High Similarity	NPC476279
0.875	High Similarity	NPC224851
0.8743	High Similarity	NPC303460
0.8743	High Similarity	NPC306321
0.8736	High Similarity	NPC150977
0.8735	High Similarity	NPC472275
0.8727	High Similarity	NPC474290
0.8727	High Similarity	NPC185258
0.8727	High Similarity	NPC172770
0.8721	High Similarity	NPC216307
0.8713	High Similarity	NPC473834
0.8706	High Similarity	NPC476365
0.8704	High Similarity	NPC475076
0.869	High Similarity	NPC259757
0.8688	High Similarity	NPC46941
0.8686	High Similarity	NPC154527
0.8683	High Similarity	NPC470694
0.8683	High Similarity	NPC219927
0.8675	High Similarity	NPC200746
0.8667	High Similarity	NPC129684
0.8667	High Similarity	NPC112954
0.8667	High Similarity	NPC187745
0.8667	High Similarity	NPC181960
0.8667	High Similarity	NPC96167
0.8667	High Similarity	NPC299520
0.8667	High Similarity	NPC469584
0.8667	High Similarity	NPC245758
0.8667	High Similarity	NPC161960
0.8667	High Similarity	NPC472914
0.8667	High Similarity	NPC222814
0.8667	High Similarity	NPC304008
0.8667	High Similarity	NPC472911
0.8667	High Similarity	NPC472913
0.8667	High Similarity	NPC79053
0.8667	High Similarity	NPC472910
0.8663	High Similarity	NPC99591
0.8655	High Similarity	NPC257667
0.8655	High Similarity	NPC186847
0.8655	High Similarity	NPC472454
0.8647	High Similarity	NPC188079
0.8647	High Similarity	NPC476637
0.8647	High Similarity	NPC475212
0.8639	High Similarity	NPC171985
0.8639	High Similarity	NPC320741
0.8639	High Similarity	NPC251336
0.8639	High Similarity	NPC472449
0.8639	High Similarity	NPC37870
0.8636	High Similarity	NPC226725
0.8631	High Similarity	NPC220313
0.8625	High Similarity	NPC209278
0.8623	High Similarity	NPC472906
0.8623	High Similarity	NPC266314
0.8623	High Similarity	NPC29876
0.8623	High Similarity	NPC234644
0.8623	High Similarity	NPC167678
0.8616	High Similarity	NPC59551
0.8606	High Similarity	NPC115853
0.8606	High Similarity	NPC274730
0.8606	High Similarity	NPC472916
0.8606	High Similarity	NPC191146
0.8606	High Similarity	NPC138243
0.8606	High Similarity	NPC68093
0.8605	High Similarity	NPC149846
0.8605	High Similarity	NPC82217
0.8605	High Similarity	NPC216842
0.8605	High Similarity	NPC476640
0.8598	High Similarity	NPC206238
0.8598	High Similarity	NPC292214
0.8598	High Similarity	NPC271779
0.8598	High Similarity	NPC88645
0.8598	High Similarity	NPC167091
0.8596	High Similarity	NPC72696
0.8596	High Similarity	NPC103307
0.8589	High Similarity	NPC251110
0.8588	High Similarity	NPC470374
0.8588	High Similarity	NPC470704
0.8588	High Similarity	NPC295082
0.8588	High Similarity	NPC478059
0.8588	High Similarity	NPC476306
0.8588	High Similarity	NPC478060
0.8588	High Similarity	NPC470377
0.8588	High Similarity	NPC471975
0.858	High Similarity	NPC234052
0.858	High Similarity	NPC58223
0.858	High Similarity	NPC169471
0.858	High Similarity	NPC72787
0.858	High Similarity	NPC7688
0.858	High Similarity	NPC125039
0.858	High Similarity	NPC36916
0.858	High Similarity	NPC36
0.858	High Similarity	NPC224280
0.858	High Similarity	NPC476170
0.858	High Similarity	NPC7154
0.8571	High Similarity	NPC25152
0.8571	High Similarity	NPC140346
0.8571	High Similarity	NPC206605
0.8571	High Similarity	NPC83922
0.8571	High Similarity	NPC47883
0.8571	High Similarity	NPC472448
0.8571	High Similarity	NPC149389
0.8563	High Similarity	NPC297807
0.8563	High Similarity	NPC204290
0.8563	High Similarity	NPC139036
0.8563	High Similarity	NPC235018
0.8563	High Similarity	NPC45146
0.8563	High Similarity	NPC471789
0.8563	High Similarity	NPC188433
0.8555	High Similarity	NPC287243
0.8554	High Similarity	NPC210084
0.8554	High Similarity	NPC474836
0.8554	High Similarity	NPC262286
0.8554	High Similarity	NPC300727
0.8554	High Similarity	NPC180011
0.8554	High Similarity	NPC48208
0.8554	High Similarity	NPC219867
0.8554	High Similarity	NPC474208
0.8554	High Similarity	NPC475267
0.8554	High Similarity	NPC36852
0.8554	High Similarity	NPC162869
0.8554	High Similarity	NPC183
0.8554	High Similarity	NPC78225
0.8554	High Similarity	NPC241904
0.8554	High Similarity	NPC99597
0.8554	High Similarity	NPC156057
0.8547	High Similarity	NPC81332
0.8547	High Similarity	NPC262580
0.8547	High Similarity	NPC289396
0.8547	High Similarity	NPC212038
0.8547	High Similarity	NPC54098
0.8547	High Similarity	NPC230619
0.8547	High Similarity	NPC4200
0.8547	High Similarity	NPC271848
0.8545	High Similarity	NPC50715
0.8545	High Similarity	NPC20830
0.8545	High Similarity	NPC128863
0.8545	High Similarity	NPC183597
0.8545	High Similarity	NPC201136
0.8545	High Similarity	NPC2928
0.8545	High Similarity	NPC255807
0.8545	High Similarity	NPC31018
0.8545	High Similarity	NPC227325
0.8545	High Similarity	NPC163780
0.8545	High Similarity	NPC196439
0.8545	High Similarity	NPC146165
0.8545	High Similarity	NPC472909
0.8545	High Similarity	NPC92659
0.8545	High Similarity	NPC2476
0.8545	High Similarity	NPC280339
0.8545	High Similarity	NPC167815
0.8545	High Similarity	NPC256612
0.8545	High Similarity	NPC138360
0.8545	High Similarity	NPC208197
0.8545	High Similarity	NPC4455
0.8539	High Similarity	NPC473618
0.8538	High Similarity	NPC107627
0.8537	High Similarity	NPC120537
0.8537	High Similarity	NPC199100
0.8537	High Similarity	NPC161277
0.8537	High Similarity	NPC180234
0.8537	High Similarity	NPC39007
0.8537	High Similarity	NPC101996
0.8529	High Similarity	NPC120593
0.8528	High Similarity	NPC248102
0.8528	High Similarity	NPC61620
0.8521	High Similarity	NPC23298
0.8521	High Similarity	NPC187491
0.8521	High Similarity	NPC236132
0.8521	High Similarity	NPC207690
0.8521	High Similarity	NPC146134
0.8521	High Similarity	NPC236521
0.8521	High Similarity	NPC319200
0.8521	High Similarity	NPC189473
0.8521	High Similarity	NPC152659
0.8521	High Similarity	NPC127415
0.8521	High Similarity	NPC248638
0.8521	High Similarity	NPC12461
0.8514	High Similarity	NPC473785

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 NPC19273 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	444
0.1-0.2	989
0.2-0.3	1841
0.3-0.4	2768
0.4-0.5	1863
0.5-0.6	827
0.6-0.7	283
0.7-0.8	104
0.8-0.85	24
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.858	High Similarity	NPD6166	Phase 2
0.858	High Similarity	NPD6168	Clinical (unspecified phase)
0.858	High Similarity	NPD6167	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD2801	Approved
0.8313	Intermediate Similarity	NPD1934	Approved
0.8235	Intermediate Similarity	NPD5494	Approved
0.8229	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6959	Discontinued
0.8171	Intermediate Similarity	NPD7074	Phase 3
0.8167	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8166	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8114	Intermediate Similarity	NPD7054	Approved
0.8103	Intermediate Similarity	NPD7473	Discontinued
0.809	Intermediate Similarity	NPD8312	Approved
0.809	Intermediate Similarity	NPD8313	Approved
0.8068	Intermediate Similarity	NPD7472	Approved
0.8059	Intermediate Similarity	NPD3882	Suspended
0.8049	Intermediate Similarity	NPD1511	Approved
0.8035	Intermediate Similarity	NPD6232	Discontinued
0.8011	Intermediate Similarity	NPD5844	Phase 1
0.7955	Intermediate Similarity	NPD3818	Discontinued
0.7952	Intermediate Similarity	NPD1512	Approved
0.7941	Intermediate Similarity	NPD1465	Phase 2
0.7933	Intermediate Similarity	NPD7808	Phase 3
0.7933	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD6797	Phase 2
0.7895	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5402	Approved
0.7877	Intermediate Similarity	NPD7251	Discontinued
0.7841	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD3817	Phase 2
0.7784	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD4380	Phase 2
0.7758	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7746	Intermediate Similarity	NPD7768	Phase 2
0.7701	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD6559	Discontinued
0.7661	Intermediate Similarity	NPD6599	Discontinued
0.763	Intermediate Similarity	NPD7819	Suspended
0.7622	Intermediate Similarity	NPD6099	Approved
0.7622	Intermediate Similarity	NPD6100	Approved
0.7616	Intermediate Similarity	NPD7411	Suspended
0.7611	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7602	Intermediate Similarity	NPD3226	Approved
0.76	Intermediate Similarity	NPD7075	Discontinued
0.76	Intermediate Similarity	NPD3749	Approved
0.7574	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD3750	Approved
0.753	Intermediate Similarity	NPD1549	Phase 2
0.7515	Intermediate Similarity	NPD7390	Discontinued
0.7486	Intermediate Similarity	NPD3926	Phase 2
0.7485	Intermediate Similarity	NPD447	Suspended
0.7485	Intermediate Similarity	NPD5403	Approved
0.7473	Intermediate Similarity	NPD8150	Discontinued
0.7471	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD2346	Discontinued
0.747	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7459	Intermediate Similarity	NPD7228	Approved
0.7439	Intermediate Similarity	NPD1607	Approved
0.7429	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD943	Approved
0.7419	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1551	Phase 2
0.7391	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD2800	Approved
0.7368	Intermediate Similarity	NPD5401	Approved
0.7368	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3751	Discontinued
0.736	Intermediate Similarity	NPD6234	Discontinued
0.7349	Intermediate Similarity	NPD1510	Phase 2
0.7329	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6776	Approved
0.732	Intermediate Similarity	NPD6779	Approved
0.732	Intermediate Similarity	NPD6780	Approved
0.732	Intermediate Similarity	NPD6781	Approved
0.732	Intermediate Similarity	NPD6777	Approved
0.732	Intermediate Similarity	NPD6778	Approved
0.732	Intermediate Similarity	NPD6782	Approved
0.7317	Intermediate Similarity	NPD1240	Approved
0.731	Intermediate Similarity	NPD6799	Approved
0.7305	Intermediate Similarity	NPD2796	Approved
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7296	Intermediate Similarity	NPD7697	Approved
0.7296	Intermediate Similarity	NPD7696	Phase 3
0.7296	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD8434	Phase 2
0.7286	Intermediate Similarity	NPD8151	Discontinued
0.7283	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1247	Approved
0.7273	Intermediate Similarity	NPD6801	Discontinued
0.7259	Intermediate Similarity	NPD7870	Phase 2
0.7259	Intermediate Similarity	NPD7871	Phase 2
0.7246	Intermediate Similarity	NPD3748	Approved
0.7245	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD3787	Discontinued
0.7236	Intermediate Similarity	NPD7701	Phase 2
0.7235	Intermediate Similarity	NPD4628	Phase 3
0.7235	Intermediate Similarity	NPD8166	Discontinued
0.7212	Intermediate Similarity	NPD1613	Approved
0.7212	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD7435	Discontinued
0.72	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4749	Approved
0.7182	Intermediate Similarity	NPD8127	Discontinued
0.7182	Intermediate Similarity	NPD7199	Phase 2
0.7178	Intermediate Similarity	NPD4908	Phase 1
0.7175	Intermediate Similarity	NPD37	Approved
0.7169	Intermediate Similarity	NPD1933	Approved
0.7151	Intermediate Similarity	NPD4966	Approved
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7143	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2799	Discontinued
0.7143	Intermediate Similarity	NPD1653	Approved
0.7135	Intermediate Similarity	NPD8455	Phase 2
0.7135	Intermediate Similarity	NPD7003	Approved
0.7129	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7801	Approved
0.7129	Intermediate Similarity	NPD7783	Phase 2
0.7128	Intermediate Similarity	NPD7700	Phase 2
0.7128	Intermediate Similarity	NPD7699	Phase 2
0.7118	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7104	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD7458	Discontinued
0.7101	Intermediate Similarity	NPD5408	Approved
0.7101	Intermediate Similarity	NPD5405	Approved
0.7101	Intermediate Similarity	NPD5404	Approved
0.7101	Intermediate Similarity	NPD5406	Approved
0.7091	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2313	Discontinued
0.7091	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD7874	Approved
0.7079	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD7549	Discontinued
0.7069	Intermediate Similarity	NPD2532	Approved
0.7069	Intermediate Similarity	NPD2533	Approved
0.7069	Intermediate Similarity	NPD2534	Approved
0.7062	Intermediate Similarity	NPD6535	Approved
0.7062	Intermediate Similarity	NPD6534	Approved
0.7059	Intermediate Similarity	NPD2344	Approved
0.7056	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2798	Approved
0.7041	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4625	Phase 3
0.703	Intermediate Similarity	NPD3027	Phase 3
0.7024	Intermediate Similarity	NPD6651	Approved
0.7021	Intermediate Similarity	NPD7685	Pre-registration
0.7021	Intermediate Similarity	NPD7240	Approved
0.6994	Remote Similarity	NPD1203	Approved
0.6994	Remote Similarity	NPD1470	Approved
0.6983	Remote Similarity	NPD6844	Discontinued
0.6978	Remote Similarity	NPD919	Approved
0.6977	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD230	Phase 1
0.6941	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD6213	Phase 3
0.6923	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6212	Phase 3
0.6915	Remote Similarity	NPD8319	Approved
0.6915	Remote Similarity	NPD8320	Phase 1
0.6914	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD2309	Approved
0.6897	Remote Similarity	NPD6190	Approved
0.689	Remote Similarity	NPD2797	Approved
0.6886	Remote Similarity	NPD411	Approved
0.6886	Remote Similarity	NPD3268	Approved
0.6871	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD6832	Phase 2
0.6866	Remote Similarity	NPD7680	Approved
0.6852	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1201	Approved
0.6836	Remote Similarity	NPD6273	Approved
0.6825	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD7907	Approved
0.6823	Remote Similarity	NPD8053	Approved
0.6823	Remote Similarity	NPD8054	Approved
0.6818	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.681	Remote Similarity	NPD9717	Approved
0.6809	Remote Similarity	NPD7177	Discontinued
0.6789	Remote Similarity	NPD5953	Discontinued
0.6769	Remote Similarity	NPD4287	Approved
0.6765	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD3300	Phase 2
0.675	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1610	Phase 2
0.673	Remote Similarity	NPD4111	Phase 1
0.673	Remote Similarity	NPD4665	Approved
0.6721	Remote Similarity	NPD4288	Approved
0.6719	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2861	Phase 2
0.6707	Remote Similarity	NPD1608	Approved
0.6707	Remote Similarity	NPD9494	Approved
0.6706	Remote Similarity	NPD4307	Phase 2
0.6704	Remote Similarity	NPD920	Approved
0.6702	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD6859	Clinical (unspecified phase)

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