NPASS Compound

Structure

NPC287354 OpenBabel07101719512D 34 37 0 0 1 0 0 0 0 0999 V2000 -0.8510 -3.7991 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1084 -3.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 -0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 -1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8435 -3.1769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 -1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4576 -2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0735 -2.8242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 -3.3002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0646 -1.2185 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5630 -1.1691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 -1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6236 -1.8002 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2472 -0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0896 -0.9960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 0.3600 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8709 -1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.0801 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0291 -2.5294 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -3.8002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7369 -2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1133 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 -1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4504 -2.2574 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3405 -2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 -2.3002 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 12 1 0 0 0 0 3 23 1 0 0 0 0 4 23 1 0 0 0 0 6 32 1 0 0 0 0 7 15 1 0 0 0 0 8 16 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 10 32 1 0 0 0 0 11 26 2 0 0 0 0 11 33 1 0 0 0 0 12 27 2 0 0 0 0 12 34 1 0 0 0 0 13 7 1 6 0 0 0 13 14 1 0 0 0 0 14 10 1 6 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 33 1 1 0 0 0 16 23 1 0 0 0 0 16 28 1 1 0 0 0 17 24 1 6 0 0 0 17 34 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 0 0 0 0 18 29 2 0 0 0 0 19 24 1 6 0 0 0 19 25 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 6 0 0 0 21 25 1 0 0 0 0 21 30 2 0 0 0 0 22 25 1 1 0 0 0 22 31 1 0 0 0 0 24 5 1 6 0 0 0 25 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.24
Volume:	475.296
LogP:	1.422
LogD:	0.779
LogS:	-2.891
# Rotatable Bonds:	6
TPSA:	136.43
# H-Bond Aceptor:	9
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.566
Synthetic Accessibility Score:	6.362
Fsp3:	0.84
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.151
MDCK Permeability:	8.469706517644227e-05
Pgp-inhibitor:	0.994
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.244
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.96

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.142
Plasma Protein Binding (PPB):	26.031877517700195%
Volume Distribution (VD):	0.707
Pgp-substrate:	68.21465301513672%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.34
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.021
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	3.471
Half-life (T1/2):	0.28

ADMET: Toxicity

hERG Blockers:	0.3
Human Hepatotoxicity (H-HT):	0.197
Drug-inuced Liver Injury (DILI):	0.768
AMES Toxicity:	0.076
Rat Oral Acute Toxicity:	0.925
Maximum Recommended Daily Dose:	0.939
Skin Sensitization:	0.522
Carcinogencity:	0.285
Eye Corrosion:	0.546
Eye Irritation:	0.013
Respiratory Toxicity:	0.986

Download Data

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

Natural Product: NPC287354

Natural Product ID:	NPC287354
*Common Name:**	Tenuifolin M
IUPAC Name:	n.a.
Synonyms:	Tenuifolin M
Standard InCHIKey:	OTJFFMFHSOWOQW-KVLNNNEYSA-N
Standard InCHI:	InChI=1S/C25H36O9/c1-11(26)33-15-7-13-9-25(21(30)14(13)10-32-6)19(15)24(5)17(34-12(2)27)8-16(28)23(3,4)20(24)18(29)22(25)31/h13-17,19-20,22,28,31H,7-10H2,1-6H3/t13-,14-,15+,16+,17+,19+,20-,22+,24+,25+/m1/s1
SMILES:	COC[C@@H]1[C@@H]2C[C@@H]([C@@H]3[C@](C1=O)(C2)[C@@H](O)C(=O)[C@H]1[C@@]3(C)[C@@H](OC(=O)C)C[C@@H](C1(C)C)O)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2334856
PubChem CID:	71577599
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane diterpenoids

*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
NPO33364	isodon tenuifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327668]
NPO33364	isodon tenuifolius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25375202]

☑ 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	6

Activity Type	# Activity
Cell Line	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	25000.0	nM	PMID[546090]
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	10000.0	nM	PMID[546090]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[546090]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[546090]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[546090]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	4400.0	nM	PMID[546090]

☑ 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 NPC287354 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	427
0.1-0.2	3264
0.2-0.3	7871
0.3-0.4	13347
0.4-0.5	6974
0.5-0.6	5279
0.6-0.7	4200
0.7-0.8	1106
0.8-0.85	185
0.85-0.9	35
0.9-0.95	7
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC62407
0.9121	High Similarity	NPC476189
0.8977	High Similarity	NPC473350
0.8864	High Similarity	NPC473336
0.8864	High Similarity	NPC471044
0.8791	High Similarity	NPC67653
0.8791	High Similarity	NPC477440
0.8791	High Similarity	NPC477443
0.8791	High Similarity	NPC61688
0.8791	High Similarity	NPC471459
0.8788	High Similarity	NPC201908
0.8788	High Similarity	NPC176949
0.8696	High Similarity	NPC477444
0.8696	High Similarity	NPC477433
0.8696	High Similarity	NPC477442
0.8696	High Similarity	NPC476296
0.8681	High Similarity	NPC226491
0.8681	High Similarity	NPC477614
0.8667	High Similarity	NPC83242
0.8667	High Similarity	NPC302111
0.8652	High Similarity	NPC50438
0.8587	High Similarity	NPC200580
0.8586	High Similarity	NPC327093
0.8586	High Similarity	NPC88469
0.8571	High Similarity	NPC275990
0.8556	High Similarity	NPC477445
0.8495	Intermediate Similarity	NPC88337
0.8495	Intermediate Similarity	NPC475211
0.8478	Intermediate Similarity	NPC473319
0.8478	Intermediate Similarity	NPC131104
0.8478	Intermediate Similarity	NPC3032
0.8469	Intermediate Similarity	NPC46848
0.8454	Intermediate Similarity	NPC476294
0.8444	Intermediate Similarity	NPC477434
0.8444	Intermediate Similarity	NPC237938
0.8444	Intermediate Similarity	NPC219535
0.8438	Intermediate Similarity	NPC116683
0.8438	Intermediate Similarity	NPC193785
0.8431	Intermediate Similarity	NPC321661
0.8431	Intermediate Similarity	NPC320475
0.8404	Intermediate Similarity	NPC52756
0.84	Intermediate Similarity	NPC47281
0.8387	Intermediate Similarity	NPC56962
0.8387	Intermediate Similarity	NPC24705
0.8384	Intermediate Similarity	NPC470172
0.8384	Intermediate Similarity	NPC471254
0.837	Intermediate Similarity	NPC263802
0.8367	Intermediate Similarity	NPC293866
0.8333	Intermediate Similarity	NPC316930
0.8317	Intermediate Similarity	NPC200957
0.8317	Intermediate Similarity	NPC28791
0.8317	Intermediate Similarity	NPC138908
0.8317	Intermediate Similarity	NPC50535
0.8317	Intermediate Similarity	NPC295366
0.83	Intermediate Similarity	NPC473406
0.8298	Intermediate Similarity	NPC77756
0.8295	Intermediate Similarity	NPC80891
0.8295	Intermediate Similarity	NPC320144
0.8295	Intermediate Similarity	NPC201276
0.828	Intermediate Similarity	NPC236459
0.8265	Intermediate Similarity	NPC89099
0.8265	Intermediate Similarity	NPC38296
0.8265	Intermediate Similarity	NPC162459
0.8265	Intermediate Similarity	NPC38471
0.8265	Intermediate Similarity	NPC98837
0.8265	Intermediate Similarity	NPC471038
0.8265	Intermediate Similarity	NPC28864
0.8265	Intermediate Similarity	NPC20479
0.8261	Intermediate Similarity	NPC477441
0.8261	Intermediate Similarity	NPC120395
0.8261	Intermediate Similarity	NPC248216
0.8242	Intermediate Similarity	NPC319909
0.8242	Intermediate Similarity	NPC473299
0.8235	Intermediate Similarity	NPC166993
0.8235	Intermediate Similarity	NPC251824
0.8235	Intermediate Similarity	NPC86852
0.8222	Intermediate Similarity	NPC61107
0.8222	Intermediate Similarity	NPC289486
0.8211	Intermediate Similarity	NPC216137
0.82	Intermediate Similarity	NPC214946
0.82	Intermediate Similarity	NPC304832
0.82	Intermediate Similarity	NPC76866
0.82	Intermediate Similarity	NPC246736
0.82	Intermediate Similarity	NPC88203
0.82	Intermediate Similarity	NPC148628
0.82	Intermediate Similarity	NPC286519
0.8182	Intermediate Similarity	NPC171426
0.8182	Intermediate Similarity	NPC224802
0.8182	Intermediate Similarity	NPC34046
0.8182	Intermediate Similarity	NPC185465
0.8182	Intermediate Similarity	NPC80089
0.8182	Intermediate Similarity	NPC94906
0.8182	Intermediate Similarity	NPC324700
0.8172	Intermediate Similarity	NPC470920
0.8172	Intermediate Similarity	NPC239938
0.8163	Intermediate Similarity	NPC10864
0.8163	Intermediate Similarity	NPC472273
0.8155	Intermediate Similarity	NPC273155
0.8152	Intermediate Similarity	NPC477205
0.8144	Intermediate Similarity	NPC305808
0.8144	Intermediate Similarity	NPC17336
0.8137	Intermediate Similarity	NPC37600
0.8137	Intermediate Similarity	NPC222833
0.8132	Intermediate Similarity	NPC15091
0.8132	Intermediate Similarity	NPC327451
0.8131	Intermediate Similarity	NPC475490
0.8119	Intermediate Similarity	NPC469985
0.8119	Intermediate Similarity	NPC122811
0.8119	Intermediate Similarity	NPC87927
0.8119	Intermediate Similarity	NPC471253
0.8105	Intermediate Similarity	NPC470114
0.81	Intermediate Similarity	NPC163963
0.81	Intermediate Similarity	NPC289148
0.81	Intermediate Similarity	NPC259654
0.81	Intermediate Similarity	NPC298266
0.81	Intermediate Similarity	NPC253886
0.81	Intermediate Similarity	NPC52899
0.81	Intermediate Similarity	NPC236585
0.81	Intermediate Similarity	NPC121218
0.8095	Intermediate Similarity	NPC470281
0.8085	Intermediate Similarity	NPC90676
0.8081	Intermediate Similarity	NPC472028
0.8081	Intermediate Similarity	NPC474793
0.8081	Intermediate Similarity	NPC253995
0.8068	Intermediate Similarity	NPC317913
0.8068	Intermediate Similarity	NPC477918
0.8068	Intermediate Similarity	NPC207010
0.8065	Intermediate Similarity	NPC472272
0.8065	Intermediate Similarity	NPC476727
0.8065	Intermediate Similarity	NPC476726
0.8061	Intermediate Similarity	NPC476728
0.8061	Intermediate Similarity	NPC329910
0.8061	Intermediate Similarity	NPC29410
0.8061	Intermediate Similarity	NPC200054
0.8061	Intermediate Similarity	NPC477264
0.8058	Intermediate Similarity	NPC203974
0.8043	Intermediate Similarity	NPC181871
0.8043	Intermediate Similarity	NPC475689
0.8043	Intermediate Similarity	NPC9060
0.8041	Intermediate Similarity	NPC477495
0.8041	Intermediate Similarity	NPC309127
0.8041	Intermediate Similarity	NPC470424
0.8041	Intermediate Similarity	NPC247877
0.8039	Intermediate Similarity	NPC84928
0.8039	Intermediate Similarity	NPC98603
0.8039	Intermediate Similarity	NPC29705
0.8039	Intermediate Similarity	NPC301787
0.8022	Intermediate Similarity	NPC121121
0.8021	Intermediate Similarity	NPC475878
0.802	Intermediate Similarity	NPC124544
0.802	Intermediate Similarity	NPC170615
0.8	Intermediate Similarity	NPC37047
0.8	Intermediate Similarity	NPC477851
0.8	Intermediate Similarity	NPC287676
0.8	Intermediate Similarity	NPC180733
0.8	Intermediate Similarity	NPC293890
0.8	Intermediate Similarity	NPC41971
0.7981	Intermediate Similarity	NPC112895
0.7981	Intermediate Similarity	NPC218123
0.7981	Intermediate Similarity	NPC211224
0.7981	Intermediate Similarity	NPC231278
0.798	Intermediate Similarity	NPC111187
0.798	Intermediate Similarity	NPC471241
0.798	Intermediate Similarity	NPC190080
0.798	Intermediate Similarity	NPC253586
0.7959	Intermediate Similarity	NPC470031
0.7959	Intermediate Similarity	NPC263135
0.7959	Intermediate Similarity	NPC470232
0.7959	Intermediate Similarity	NPC288906
0.7959	Intermediate Similarity	NPC98639
0.7959	Intermediate Similarity	NPC470229
0.7957	Intermediate Similarity	NPC474572
0.7955	Intermediate Similarity	NPC472487
0.7955	Intermediate Similarity	NPC471046
0.7955	Intermediate Similarity	NPC472486
0.7955	Intermediate Similarity	NPC477933
0.7955	Intermediate Similarity	NPC4209
0.7955	Intermediate Similarity	NPC474020
0.7955	Intermediate Similarity	NPC477932
0.7944	Intermediate Similarity	NPC97002
0.7941	Intermediate Similarity	NPC209298
0.7941	Intermediate Similarity	NPC34562
0.7941	Intermediate Similarity	NPC277074
0.7941	Intermediate Similarity	NPC96217
0.7941	Intermediate Similarity	NPC139347
0.7941	Intermediate Similarity	NPC216114
0.7938	Intermediate Similarity	NPC474379
0.7938	Intermediate Similarity	NPC161035
0.7925	Intermediate Similarity	NPC473062
0.7921	Intermediate Similarity	NPC477052
0.7921	Intermediate Similarity	NPC252614
0.7921	Intermediate Similarity	NPC75941
0.7921	Intermediate Similarity	NPC477053
0.7921	Intermediate Similarity	NPC477051
0.7912	Intermediate Similarity	NPC475743
0.7912	Intermediate Similarity	NPC58631
0.7905	Intermediate Similarity	NPC228190
0.7905	Intermediate Similarity	NPC236753
0.79	Intermediate Similarity	NPC78427
0.79	Intermediate Similarity	NPC16911

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 NPC287354 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	453
0.1-0.2	3511
0.2-0.3	3319
0.3-0.4	1057
0.4-0.5	399
0.5-0.6	219
0.6-0.7	152
0.7-0.8	33
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD6114	Approved
0.8182	Intermediate Similarity	NPD6115	Approved
0.8182	Intermediate Similarity	NPD6697	Approved
0.8182	Intermediate Similarity	NPD6118	Approved
0.8068	Intermediate Similarity	NPD6116	Phase 1
0.7955	Intermediate Similarity	NPD6117	Approved
0.7841	Intermediate Similarity	NPD3703	Phase 2
0.7727	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD1700	Approved
0.757	Intermediate Similarity	NPD6372	Approved
0.757	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7475	Intermediate Similarity	NPD8035	Phase 2
0.7475	Intermediate Similarity	NPD8034	Phase 2
0.7431	Intermediate Similarity	NPD6650	Approved
0.7431	Intermediate Similarity	NPD6649	Approved
0.7386	Intermediate Similarity	NPD4789	Approved
0.7358	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6402	Approved
0.729	Intermediate Similarity	NPD5739	Approved
0.729	Intermediate Similarity	NPD6675	Approved
0.729	Intermediate Similarity	NPD7128	Approved
0.7273	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD6319	Approved
0.7156	Intermediate Similarity	NPD6881	Approved
0.7156	Intermediate Similarity	NPD7320	Approved
0.7156	Intermediate Similarity	NPD6899	Approved
0.7111	Intermediate Similarity	NPD5777	Approved
0.7111	Intermediate Similarity	NPD6081	Approved
0.7105	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD3702	Approved
0.7064	Intermediate Similarity	NPD5697	Approved
0.7064	Intermediate Similarity	NPD5701	Approved
0.7059	Intermediate Similarity	NPD6399	Phase 3
0.7054	Intermediate Similarity	NPD6882	Approved
0.7054	Intermediate Similarity	NPD8297	Approved
0.7041	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6883	Approved
0.7027	Intermediate Similarity	NPD7290	Approved
0.7027	Intermediate Similarity	NPD7102	Approved
0.7009	Intermediate Similarity	NPD6921	Approved
0.7	Intermediate Similarity	NPD4244	Approved
0.7	Intermediate Similarity	NPD4245	Approved
0.6975	Remote Similarity	NPD7492	Approved
0.6966	Remote Similarity	NPD5360	Phase 3
0.6966	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD6869	Approved
0.6964	Remote Similarity	NPD6617	Approved
0.6964	Remote Similarity	NPD6847	Approved
0.6964	Remote Similarity	NPD8130	Phase 1
0.6942	Remote Similarity	NPD7736	Approved
0.6937	Remote Similarity	NPD6012	Approved
0.6937	Remote Similarity	NPD6013	Approved
0.6937	Remote Similarity	NPD6014	Approved
0.6932	Remote Similarity	NPD4224	Phase 2
0.6923	Remote Similarity	NPD6054	Approved
0.6923	Remote Similarity	NPD6059	Approved
0.6917	Remote Similarity	NPD6616	Approved
0.6891	Remote Similarity	NPD8328	Phase 3
0.6889	Remote Similarity	NPD3698	Phase 2
0.686	Remote Similarity	NPD8293	Discontinued
0.686	Remote Similarity	NPD7078	Approved
0.6857	Remote Similarity	NPD4697	Phase 3
0.6847	Remote Similarity	NPD6011	Approved
0.6842	Remote Similarity	NPD4632	Approved
0.6818	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6370	Approved
0.6792	Remote Similarity	NPD4755	Approved
0.6786	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7319	Approved
0.6729	Remote Similarity	NPD7638	Approved
0.6726	Remote Similarity	NPD4634	Approved
0.6723	Remote Similarity	NPD6015	Approved
0.6723	Remote Similarity	NPD6016	Approved
0.6703	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6928	Phase 2
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD6008	Approved
0.6667	Remote Similarity	NPD5286	Approved
0.6667	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD5285	Approved
0.6667	Remote Similarity	NPD3671	Phase 1
0.6667	Remote Similarity	NPD8418	Phase 2
0.6667	Remote Similarity	NPD6009	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5988	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6636	Remote Similarity	NPD7902	Approved
0.6636	Remote Similarity	NPD6084	Phase 2
0.6636	Remote Similarity	NPD6083	Phase 2
0.6612	Remote Similarity	NPD7604	Phase 2
0.6602	Remote Similarity	NPD5328	Approved
0.6583	Remote Similarity	NPD5983	Phase 2
0.6581	Remote Similarity	NPD6274	Approved
0.6579	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4758	Discontinued
0.6555	Remote Similarity	NPD7101	Approved
0.6555	Remote Similarity	NPD7100	Approved
0.6552	Remote Similarity	NPD8133	Approved
0.6545	Remote Similarity	NPD4633	Approved
0.6545	Remote Similarity	NPD5226	Approved
0.6545	Remote Similarity	NPD7632	Discontinued
0.6545	Remote Similarity	NPD5224	Approved
0.6545	Remote Similarity	NPD5225	Approved
0.6545	Remote Similarity	NPD5211	Phase 2
0.6542	Remote Similarity	NPD5222	Approved
0.6542	Remote Similarity	NPD5221	Approved
0.6542	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD4767	Approved
0.6518	Remote Similarity	NPD4768	Approved
0.6504	Remote Similarity	NPD7507	Approved
0.6504	Remote Similarity	NPD6336	Discontinued
0.6495	Remote Similarity	NPD4238	Approved
0.6495	Remote Similarity	NPD5364	Discontinued
0.6495	Remote Similarity	NPD4802	Phase 2
0.6486	Remote Similarity	NPD5175	Approved
0.6486	Remote Similarity	NPD5174	Approved
0.6481	Remote Similarity	NPD5173	Approved
0.6476	Remote Similarity	NPD6079	Approved
0.6471	Remote Similarity	NPD6335	Approved
0.6455	Remote Similarity	NPD5223	Approved
0.6446	Remote Similarity	NPD6909	Approved
0.6446	Remote Similarity	NPD6908	Approved
0.6441	Remote Similarity	NPD6940	Discontinued
0.6441	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD5696	Approved
0.6415	Remote Similarity	NPD8171	Discontinued
0.6404	Remote Similarity	NPD4730	Approved
0.6404	Remote Similarity	NPD4729	Approved
0.64	Remote Similarity	NPD6033	Approved
0.6387	Remote Similarity	NPD7115	Discovery
0.6387	Remote Similarity	NPD6317	Approved
0.6355	Remote Similarity	NPD7900	Approved
0.6355	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD7748	Approved
0.6348	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD6672	Approved
0.6346	Remote Similarity	NPD5737	Approved
0.6339	Remote Similarity	NPD4754	Approved
0.6337	Remote Similarity	NPD3669	Approved
0.6337	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6313	Approved
0.6333	Remote Similarity	NPD6314	Approved
0.6321	Remote Similarity	NPD7515	Phase 2
0.6316	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6311	Remote Similarity	NPD3618	Phase 1
0.6296	Remote Similarity	NPD5695	Phase 3
0.6293	Remote Similarity	NPD5248	Approved
0.6293	Remote Similarity	NPD5247	Approved
0.6293	Remote Similarity	NPD5249	Phase 3
0.6293	Remote Similarity	NPD5250	Approved
0.6293	Remote Similarity	NPD5251	Approved
0.6275	Remote Similarity	NPD4786	Approved
0.6261	Remote Similarity	NPD5128	Approved
0.6237	Remote Similarity	NPD229	Approved
0.6176	Remote Similarity	NPD4788	Approved
0.6174	Remote Similarity	NPD6412	Phase 2
0.6168	Remote Similarity	NPD7637	Suspended
0.6168	Remote Similarity	NPD6411	Approved
0.6139	Remote Similarity	NPD1780	Approved
0.6139	Remote Similarity	NPD1779	Approved
0.6134	Remote Similarity	NPD8298	Phase 2
0.6132	Remote Similarity	NPD4753	Phase 2
0.6111	Remote Similarity	NPD4202	Approved
0.6105	Remote Similarity	NPD4787	Phase 1
0.6102	Remote Similarity	NPD5215	Approved
0.6102	Remote Similarity	NPD5217	Approved
0.6102	Remote Similarity	NPD5216	Approved
0.609	Remote Similarity	NPD6333	Approved
0.609	Remote Similarity	NPD6334	Approved
0.6078	Remote Similarity	NPD3667	Approved
0.6066	Remote Similarity	NPD7327	Approved
0.6066	Remote Similarity	NPD7328	Approved
0.604	Remote Similarity	NPD7525	Registered
0.6038	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6017	Remote Similarity	NPD5169	Approved
0.6017	Remote Similarity	NPD5135	Approved
0.6017	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD7516	Approved
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5210	Approved
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD4629	Approved
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD6684	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD5168	Approved
0.5983	Remote Similarity	NPD6686	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