NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	280.13
Volume:	272.449
LogP:	1.437
LogD:	0.844
LogS:	-4.048
# Rotatable Bonds:	0
TPSA:	76.13
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	5.667
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.105
MDCK Permeability:	2.6756757506518625e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.329

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.972
Plasma Protein Binding (PPB):	33.63629913330078%
Volume Distribution (VD):	1.14
Pgp-substrate:	72.79386901855469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.963
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.812
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.076
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.306
CYP3A4-substrate:	0.412

ADMET: Excretion

Clearance (CL):	9.45
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.195
Drug-inuced Liver Injury (DILI):	0.497
AMES Toxicity:	0.038
Rat Oral Acute Toxicity:	0.938
Maximum Recommended Daily Dose:	0.185
Skin Sensitization:	0.373
Carcinogencity:	0.791
Eye Corrosion:	0.147
Eye Irritation:	0.219
Respiratory Toxicity:	0.145

Download Data

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

Natural Product: NPC471915

Natural Product ID:	NPC471915
*Common Name:**	CWMOWQZTEGRBHX-QFNDOPATSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CWMOWQZTEGRBHX-QFNDOPATSA-N
Standard InCHI:	InChI=1S/C15H20O5/c1-7-4-5-9-14(19-9)6-15(18)10(8(2)12(17)20-15)11(16)13(7,14)3/h7,9,11,16,18H,4-6H2,1-3H3/t7-,9+,11+,13-,14+,15+/m0/s1
SMILES:	CC1CCC2C3(C1(C(C4=C(C(=O)OC4(C3)O)C)O)C)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3297916
PubChem CID:	90682828
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24913558]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26428	Ligularia sagitta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26428	Ligularia sagitta	Species	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
MIC	5

Activity Type	# Activity
Organism	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	62.5	ug.mL-1	PMID[486022]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	125.0	ug.mL-1	PMID[486022]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	125.0	ug.mL-1	PMID[486022]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	125.0	ug.mL-1	PMID[486022]
NPT1286	Organism	Pectobacterium carotovorum	Pectobacterium carotovorum	MIC	=	125.0	ug.mL-1	PMID[486022]

☑ 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 NPC471915 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	225
0.1-0.2	1623
0.2-0.3	4972
0.3-0.4	9272
0.4-0.5	13037
0.5-0.6	7469
0.6-0.7	5007
0.7-0.8	998
0.8-0.85	68
0.85-0.9	13
0.9-0.95	11
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC111273
0.9551	High Similarity	NPC472640
0.9551	High Similarity	NPC472641
0.9545	High Similarity	NPC472642
0.9438	High Similarity	NPC78594
0.9362	High Similarity	NPC471914
0.9355	High Similarity	NPC16601
0.9263	High Similarity	NPC471938
0.9167	High Similarity	NPC471937
0.9121	High Similarity	NPC110022
0.9032	High Similarity	NPC165632
0.8977	High Similarity	NPC253604
0.8864	High Similarity	NPC32223
0.8763	High Similarity	NPC475038
0.8763	High Similarity	NPC109195
0.87	High Similarity	NPC181994
0.8681	High Similarity	NPC242448
0.8673	High Similarity	NPC474822
0.8557	High Similarity	NPC324841
0.8526	High Similarity	NPC276110
0.8526	High Similarity	NPC472441
0.8421	Intermediate Similarity	NPC105490
0.8416	Intermediate Similarity	NPC471205
0.8367	Intermediate Similarity	NPC38855
0.8351	Intermediate Similarity	NPC205143
0.8333	Intermediate Similarity	NPC38948
0.8316	Intermediate Similarity	NPC472812
0.8316	Intermediate Similarity	NPC7349
0.83	Intermediate Similarity	NPC165608
0.83	Intermediate Similarity	NPC120009
0.83	Intermediate Similarity	NPC45897
0.8265	Intermediate Similarity	NPC278673
0.8265	Intermediate Similarity	NPC325229
0.8265	Intermediate Similarity	NPC275086
0.8261	Intermediate Similarity	NPC131813
0.8252	Intermediate Similarity	NPC299590
0.8252	Intermediate Similarity	NPC206618
0.8247	Intermediate Similarity	NPC134072
0.8247	Intermediate Similarity	NPC209297
0.8247	Intermediate Similarity	NPC475380
0.8247	Intermediate Similarity	NPC319861
0.8247	Intermediate Similarity	NPC234993
0.8235	Intermediate Similarity	NPC122816
0.8235	Intermediate Similarity	NPC475074
0.8229	Intermediate Similarity	NPC161998
0.8229	Intermediate Similarity	NPC140277
0.8211	Intermediate Similarity	NPC472811
0.82	Intermediate Similarity	NPC472815
0.82	Intermediate Similarity	NPC58329
0.82	Intermediate Similarity	NPC121423
0.82	Intermediate Similarity	NPC476081
0.819	Intermediate Similarity	NPC42658
0.8163	Intermediate Similarity	NPC100912
0.8163	Intermediate Similarity	NPC51499
0.8163	Intermediate Similarity	NPC311241
0.8163	Intermediate Similarity	NPC475446
0.8155	Intermediate Similarity	NPC325054
0.8144	Intermediate Similarity	NPC329435
0.8137	Intermediate Similarity	NPC81630
0.8137	Intermediate Similarity	NPC477090
0.8137	Intermediate Similarity	NPC51719
0.8119	Intermediate Similarity	NPC471208
0.8105	Intermediate Similarity	NPC78973
0.81	Intermediate Similarity	NPC11974
0.8085	Intermediate Similarity	NPC472809
0.8085	Intermediate Similarity	NPC472810
0.8085	Intermediate Similarity	NPC93411
0.8081	Intermediate Similarity	NPC72647
0.8081	Intermediate Similarity	NPC107806
0.8077	Intermediate Similarity	NPC31522
0.8061	Intermediate Similarity	NPC194132
0.8058	Intermediate Similarity	NPC187435
0.8058	Intermediate Similarity	NPC67321
0.8041	Intermediate Similarity	NPC57117
0.8039	Intermediate Similarity	NPC161775
0.8021	Intermediate Similarity	NPC473675
0.8021	Intermediate Similarity	NPC329842
0.802	Intermediate Similarity	NPC295791
0.802	Intermediate Similarity	NPC472552
0.802	Intermediate Similarity	NPC165250
0.8	Intermediate Similarity	NPC10636
0.8	Intermediate Similarity	NPC177047
0.8	Intermediate Similarity	NPC476767
0.7981	Intermediate Similarity	NPC90946
0.7981	Intermediate Similarity	NPC300614
0.798	Intermediate Similarity	NPC199099
0.798	Intermediate Similarity	NPC287668
0.7961	Intermediate Similarity	NPC218158
0.7961	Intermediate Similarity	NPC34768
0.7941	Intermediate Similarity	NPC196471
0.7941	Intermediate Similarity	NPC10232
0.7941	Intermediate Similarity	NPC281378
0.7941	Intermediate Similarity	NPC187302
0.7941	Intermediate Similarity	NPC189588
0.7941	Intermediate Similarity	NPC97487
0.7941	Intermediate Similarity	NPC159533
0.7941	Intermediate Similarity	NPC120321
0.7938	Intermediate Similarity	NPC139692
0.7938	Intermediate Similarity	NPC152778
0.7938	Intermediate Similarity	NPC205034
0.7938	Intermediate Similarity	NPC53555
0.7938	Intermediate Similarity	NPC162615
0.7935	Intermediate Similarity	NPC311070
0.7925	Intermediate Similarity	NPC469655
0.7925	Intermediate Similarity	NPC474846
0.7925	Intermediate Similarity	NPC469656
0.7921	Intermediate Similarity	NPC471412
0.7921	Intermediate Similarity	NPC198992
0.7921	Intermediate Similarity	NPC472554
0.7917	Intermediate Similarity	NPC209816
0.7905	Intermediate Similarity	NPC322912
0.7905	Intermediate Similarity	NPC475030
0.79	Intermediate Similarity	NPC474440
0.789	Intermediate Similarity	NPC13713
0.7889	Intermediate Similarity	NPC110373
0.7889	Intermediate Similarity	NPC80471
0.7889	Intermediate Similarity	NPC5908
0.7879	Intermediate Similarity	NPC202833
0.7879	Intermediate Similarity	NPC242848
0.7879	Intermediate Similarity	NPC320231
0.7857	Intermediate Similarity	NPC474554
0.7857	Intermediate Similarity	NPC474555
0.7857	Intermediate Similarity	NPC470255
0.7849	Intermediate Similarity	NPC102048
0.7843	Intermediate Similarity	NPC162973
0.7835	Intermediate Similarity	NPC249034
0.7835	Intermediate Similarity	NPC124374
0.7835	Intermediate Similarity	NPC72845
0.7822	Intermediate Similarity	NPC47024
0.7822	Intermediate Similarity	NPC477716
0.7822	Intermediate Similarity	NPC477721
0.7822	Intermediate Similarity	NPC79303
0.7822	Intermediate Similarity	NPC251680
0.7822	Intermediate Similarity	NPC471413
0.7812	Intermediate Similarity	NPC470734
0.781	Intermediate Similarity	NPC306265
0.781	Intermediate Similarity	NPC50124
0.78	Intermediate Similarity	NPC254121
0.78	Intermediate Similarity	NPC477719
0.78	Intermediate Similarity	NPC473244
0.78	Intermediate Similarity	NPC477718
0.78	Intermediate Similarity	NPC136781
0.7798	Intermediate Similarity	NPC471816
0.7789	Intermediate Similarity	NPC473891
0.7789	Intermediate Similarity	NPC471779
0.7789	Intermediate Similarity	NPC166857
0.7788	Intermediate Similarity	NPC471206
0.7788	Intermediate Similarity	NPC119855
0.7788	Intermediate Similarity	NPC220217
0.7788	Intermediate Similarity	NPC85670
0.7788	Intermediate Similarity	NPC472818
0.7788	Intermediate Similarity	NPC239961
0.7767	Intermediate Similarity	NPC472821
0.7767	Intermediate Similarity	NPC160583
0.7767	Intermediate Similarity	NPC23584
0.7755	Intermediate Similarity	NPC99653
0.7745	Intermediate Similarity	NPC25177
0.7745	Intermediate Similarity	NPC268829
0.7745	Intermediate Similarity	NPC475958
0.7745	Intermediate Similarity	NPC247701
0.7745	Intermediate Similarity	NPC477717
0.7745	Intermediate Similarity	NPC295110
0.7745	Intermediate Similarity	NPC222875
0.7742	Intermediate Similarity	NPC321385
0.7736	Intermediate Similarity	NPC257853
0.7732	Intermediate Similarity	NPC221111
0.7732	Intermediate Similarity	NPC280149
0.7732	Intermediate Similarity	NPC220216
0.7732	Intermediate Similarity	NPC310479
0.7732	Intermediate Similarity	NPC182136
0.7727	Intermediate Similarity	NPC290693
0.7723	Intermediate Similarity	NPC218107
0.7723	Intermediate Similarity	NPC216478
0.7723	Intermediate Similarity	NPC473154
0.7723	Intermediate Similarity	NPC222303
0.7714	Intermediate Similarity	NPC216636
0.7714	Intermediate Similarity	NPC472820
0.7714	Intermediate Similarity	NPC179380
0.7714	Intermediate Similarity	NPC302788
0.7714	Intermediate Similarity	NPC319438
0.7708	Intermediate Similarity	NPC291665
0.77	Intermediate Similarity	NPC260796
0.77	Intermediate Similarity	NPC221801
0.77	Intermediate Similarity	NPC473153
0.77	Intermediate Similarity	NPC162346
0.77	Intermediate Similarity	NPC284194
0.77	Intermediate Similarity	NPC16967
0.77	Intermediate Similarity	NPC17578
0.77	Intermediate Similarity	NPC240673
0.77	Intermediate Similarity	NPC475304
0.77	Intermediate Similarity	NPC211810
0.77	Intermediate Similarity	NPC471765
0.77	Intermediate Similarity	NPC129569
0.77	Intermediate Similarity	NPC93245
0.7692	Intermediate Similarity	NPC472819
0.7684	Intermediate Similarity	NPC471219
0.7677	Intermediate Similarity	NPC182826
0.7677	Intermediate Similarity	NPC105375
0.7677	Intermediate Similarity	NPC469596
0.7677	Intermediate Similarity	NPC191521

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 NPC471915 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	1921
0.2-0.3	3929
0.3-0.4	2099
0.4-0.5	646
0.5-0.6	253
0.6-0.7	101
0.7-0.8	13
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8252	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD7639	Approved
0.7822	Intermediate Similarity	NPD7640	Approved
0.7723	Intermediate Similarity	NPD7638	Approved
0.7714	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD7632	Discontinued
0.7573	Intermediate Similarity	NPD5344	Discontinued
0.7549	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD7328	Approved
0.75	Intermediate Similarity	NPD7327	Approved
0.7477	Intermediate Similarity	NPD6686	Approved
0.7434	Intermediate Similarity	NPD7516	Approved
0.7308	Intermediate Similarity	NPD6648	Approved
0.7304	Intermediate Similarity	NPD8379	Approved
0.7304	Intermediate Similarity	NPD8378	Approved
0.7304	Intermediate Similarity	NPD8335	Approved
0.7304	Intermediate Similarity	NPD8296	Approved
0.7304	Intermediate Similarity	NPD8380	Approved
0.7217	Intermediate Similarity	NPD8377	Approved
0.7217	Intermediate Similarity	NPD8294	Approved
0.7155	Intermediate Similarity	NPD8033	Approved
0.7059	Intermediate Similarity	NPD7507	Approved
0.7025	Intermediate Similarity	NPD7319	Approved
0.6957	Remote Similarity	NPD7115	Discovery
0.6939	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7503	Approved
0.6796	Remote Similarity	NPD7637	Suspended
0.6768	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD7838	Discovery
0.6699	Remote Similarity	NPD6698	Approved
0.6699	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD6695	Phase 3
0.6667	Remote Similarity	NPD6402	Approved
0.6637	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD6882	Approved
0.6607	Remote Similarity	NPD5701	Approved
0.6607	Remote Similarity	NPD5697	Approved
0.6574	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD8133	Approved
0.6549	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD6899	Approved
0.6549	Remote Similarity	NPD7320	Approved
0.6549	Remote Similarity	NPD6881	Approved
0.6535	Remote Similarity	NPD1694	Approved
0.6525	Remote Similarity	NPD6009	Approved
0.6509	Remote Similarity	NPD7748	Approved
0.6491	Remote Similarity	NPD6373	Approved
0.6491	Remote Similarity	NPD6012	Approved
0.6491	Remote Similarity	NPD6372	Approved
0.6491	Remote Similarity	NPD6013	Approved
0.6491	Remote Similarity	NPD6014	Approved
0.6481	Remote Similarity	NPD7902	Approved
0.6476	Remote Similarity	NPD7515	Phase 2
0.646	Remote Similarity	NPD6412	Phase 2
0.6455	Remote Similarity	NPD4159	Approved
0.6435	Remote Similarity	NPD7102	Approved
0.6435	Remote Similarity	NPD6371	Approved
0.6435	Remote Similarity	NPD6883	Approved
0.6435	Remote Similarity	NPD7290	Approved
0.6423	Remote Similarity	NPD7492	Approved
0.641	Remote Similarity	NPD4632	Approved
0.6408	Remote Similarity	NPD7750	Discontinued
0.6408	Remote Similarity	NPD7524	Approved
0.6404	Remote Similarity	NPD6011	Approved
0.6396	Remote Similarity	NPD5211	Phase 2
0.6381	Remote Similarity	NPD3168	Discontinued
0.6379	Remote Similarity	NPD6650	Approved
0.6379	Remote Similarity	NPD6649	Approved
0.6379	Remote Similarity	NPD6869	Approved
0.6379	Remote Similarity	NPD6847	Approved
0.6379	Remote Similarity	NPD6617	Approved
0.6379	Remote Similarity	NPD8130	Phase 1
0.6371	Remote Similarity	NPD6616	Approved
0.6364	Remote Similarity	NPD6059	Approved
0.6364	Remote Similarity	NPD7525	Registered
0.6364	Remote Similarity	NPD6930	Phase 2
0.6364	Remote Similarity	NPD6931	Approved
0.6364	Remote Similarity	NPD6054	Approved
0.6364	Remote Similarity	NPD6319	Approved
0.633	Remote Similarity	NPD6083	Phase 2
0.633	Remote Similarity	NPD6084	Phase 2
0.633	Remote Similarity	NPD4755	Approved
0.6325	Remote Similarity	NPD6053	Discontinued
0.6325	Remote Similarity	NPD8297	Approved
0.632	Remote Similarity	NPD8293	Discontinued
0.632	Remote Similarity	NPD7078	Approved
0.6311	Remote Similarity	NPD6015	Approved
0.6311	Remote Similarity	NPD6016	Approved
0.6311	Remote Similarity	NPD3618	Phase 1
0.6286	Remote Similarity	NPD6051	Approved
0.6283	Remote Similarity	NPD5141	Approved
0.627	Remote Similarity	NPD7736	Approved
0.6263	Remote Similarity	NPD6929	Approved
0.6262	Remote Similarity	NPD4202	Approved
0.6262	Remote Similarity	NPD5778	Approved
0.6262	Remote Similarity	NPD6399	Phase 3
0.6262	Remote Similarity	NPD5779	Approved
0.626	Remote Similarity	NPD5988	Approved
0.626	Remote Similarity	NPD6370	Approved
0.625	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD4700	Approved
0.6216	Remote Similarity	NPD4696	Approved
0.6216	Remote Similarity	NPD5286	Approved
0.6216	Remote Similarity	NPD5285	Approved
0.621	Remote Similarity	NPD8328	Phase 3
0.621	Remote Similarity	NPD7604	Phase 2
0.6204	Remote Similarity	NPD7900	Approved
0.6204	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7514	Phase 3
0.62	Remote Similarity	NPD7332	Phase 2
0.6179	Remote Similarity	NPD5983	Phase 2
0.6168	Remote Similarity	NPD8034	Phase 2
0.6168	Remote Similarity	NPD8035	Phase 2
0.6168	Remote Similarity	NPD7087	Discontinued
0.6167	Remote Similarity	NPD6274	Approved
0.6147	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5695	Phase 3
0.6139	Remote Similarity	NPD6902	Approved
0.6132	Remote Similarity	NPD5328	Approved
0.6132	Remote Similarity	NPD1695	Approved
0.6126	Remote Similarity	NPD5696	Approved
0.6106	Remote Similarity	NPD5224	Approved
0.6106	Remote Similarity	NPD5225	Approved
0.6106	Remote Similarity	NPD4633	Approved
0.6106	Remote Similarity	NPD5226	Approved
0.6102	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.61	Remote Similarity	NPD7645	Phase 2
0.6095	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5776	Phase 2
0.6061	Remote Similarity	NPD6925	Approved
0.6058	Remote Similarity	NPD1696	Phase 3
0.6058	Remote Similarity	NPD6893	Approved
0.6058	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5175	Approved
0.6053	Remote Similarity	NPD5174	Approved
0.6048	Remote Similarity	NPD8516	Approved
0.6048	Remote Similarity	NPD8517	Approved
0.6048	Remote Similarity	NPD8515	Approved
0.6048	Remote Similarity	NPD8513	Phase 3
0.6019	Remote Similarity	NPD5693	Phase 1
0.6019	Remote Similarity	NPD6079	Approved
0.6018	Remote Similarity	NPD5223	Approved
0.6017	Remote Similarity	NPD4634	Approved
0.6016	Remote Similarity	NPD7100	Approved
0.6016	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD4249	Approved
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6115	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6114	Approved
0.6	Remote Similarity	NPD7145	Approved
0.6	Remote Similarity	NPD6118	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD6697	Approved
0.5984	Remote Similarity	NPD6336	Discontinued
0.5984	Remote Similarity	NPD6317	Approved
0.5981	Remote Similarity	NPD4753	Phase 2
0.598	Remote Similarity	NPD6898	Phase 1
0.5962	Remote Similarity	NPD3666	Approved
0.5962	Remote Similarity	NPD3133	Approved
0.5962	Remote Similarity	NPD3665	Phase 1
0.5952	Remote Similarity	NPD6067	Discontinued
0.5948	Remote Similarity	NPD4768	Approved
0.5948	Remote Similarity	NPD4767	Approved
0.5946	Remote Similarity	NPD5222	Approved
0.5946	Remote Similarity	NPD4697	Phase 3
0.5946	Remote Similarity	NPD5221	Approved
0.5946	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD3573	Approved
0.5943	Remote Similarity	NPD4250	Approved
0.5943	Remote Similarity	NPD4251	Approved
0.5935	Remote Similarity	NPD6335	Approved
0.5935	Remote Similarity	NPD6313	Approved
0.5935	Remote Similarity	NPD6314	Approved
0.5926	Remote Similarity	NPD5785	Approved
0.5922	Remote Similarity	NPD3667	Approved
0.592	Remote Similarity	NPD6921	Approved
0.592	Remote Similarity	NPD6909	Approved
0.592	Remote Similarity	NPD6908	Approved
0.5913	Remote Similarity	NPD4754	Approved
0.5909	Remote Similarity	NPD5282	Discontinued
0.5905	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.59	Remote Similarity	NPD6116	Phase 1
0.59	Remote Similarity	NPD6932	Approved
0.5897	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD5173	Approved
0.5891	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