NPASS Compound

Structure

NPC472496 OpenBabel07101719152D 24 27 0 0 1 0 0 0 0 0999 V2000 1.4576 -2.1380 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 -1.2472 -2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8709 -1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6236 -1.8002 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 0.9195 0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0646 -1.2185 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 0.5630 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2472 -0.0000 0.0000 C 0 0 2 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 2 0 0 0 0 0 0 0 0 0 -0.6236 0.3600 0.0000 C 0 0 2 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 0.3405 -2.1440 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 1 10 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 12 1 0 0 0 0 9 11 1 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 8 1 1 0 0 0 12 14 1 0 0 0 0 12 21 2 0 0 0 0 13 15 1 0 0 0 0 13 17 1 0 0 0 0 13 22 1 1 0 0 0 14 19 1 1 0 0 0 14 20 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 1 0 0 0 16 20 1 1 0 0 0 16 23 1 0 0 0 0 17 20 1 1 0 0 0 17 24 1 0 0 0 0 19 4 1 1 0 0 0 20 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.21
Volume:	350.138
LogP:	2.34
LogD:	2.075
LogS:	-3.646
# Rotatable Bonds:	0
TPSA:	77.76
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.593
Synthetic Accessibility Score:	6.121
Fsp3:	0.85
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:	-5.123
MDCK Permeability:	2.038035381701775e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.997
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.807
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.506
Plasma Protein Binding (PPB):	52.08711242675781%
Volume Distribution (VD):	1.332
Pgp-substrate:	58.84873962402344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.412
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.712
CYP2C9-inhibitor:	0.028
CYP2C9-substrate:	0.195
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.254
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.092

ADMET: Excretion

Clearance (CL):	5.568
Half-life (T1/2):	0.211

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.071
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.165
Carcinogencity:	0.026
Eye Corrosion:	0.018
Eye Irritation:	0.03
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC472496

Natural Product ID:	NPC472496
*Common Name:**	AUVGEKXCVIHEPI-WQUFKNEXSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	AUVGEKXCVIHEPI-WQUFKNEXSA-N
Standard InCHI:	InChI=1S/C20H30O4/c1-10-11-8-12(21)14-19(4)7-5-6-18(2,3)15(19)13(22)17(24)20(14,9-11)16(10)23/h11,13-17,22-24H,1,5-9H2,2-4H3/t11-,13-,14+,15-,16-,17-,19+,20+/m1/s1
SMILES:	C=C1[C@@H]2CC(=O)[C@@H]3[C@]([C@@H]1O)(C2)[C@H](O)[C@H](O)[C@H]1[C@@]3(C)CCCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426508
PubChem CID:	n.a.
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
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	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	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[469029]
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	>	50000.0	nM	PMID[469029]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	50000.0	nM	PMID[469029]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[469029]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[469029]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	50000.0	nM	PMID[469029]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[469029]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[469029]

☑ 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 NPC472496 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	205
0.1-0.2	1651
0.2-0.3	5733
0.3-0.4	13794
0.4-0.5	8609
0.5-0.6	5416
0.6-0.7	5250
0.7-0.8	1789
0.8-0.85	215
0.85-0.9	29
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC472495
0.9419	High Similarity	NPC472497
0.9318	High Similarity	NPC100313
0.9222	High Similarity	NPC280804
0.8953	High Similarity	NPC472498
0.8764	High Similarity	NPC174619
0.8737	High Similarity	NPC291785
0.8737	High Similarity	NPC127408
0.8696	High Similarity	NPC59170
0.8681	High Similarity	NPC180849
0.8646	High Similarity	NPC253886
0.8646	High Similarity	NPC121218
0.8636	High Similarity	NPC146683
0.8586	High Similarity	NPC83744
0.8557	High Similarity	NPC477915
0.8556	High Similarity	NPC153604
0.8556	High Similarity	NPC4643
0.8526	High Similarity	NPC170978
0.8523	High Similarity	NPC118800
0.8511	High Similarity	NPC138245
0.8511	High Similarity	NPC29112
0.8511	High Similarity	NPC84018
0.8511	High Similarity	NPC231060
0.85	High Similarity	NPC329417
0.8495	Intermediate Similarity	NPC59350
0.8495	Intermediate Similarity	NPC181594
0.8495	Intermediate Similarity	NPC144739
0.8485	Intermediate Similarity	NPC48733
0.8485	Intermediate Similarity	NPC49958
0.8485	Intermediate Similarity	NPC296945
0.8485	Intermediate Similarity	NPC150531
0.8485	Intermediate Similarity	NPC260268
0.8485	Intermediate Similarity	NPC171137
0.8485	Intermediate Similarity	NPC152695
0.8485	Intermediate Similarity	NPC50692
0.8485	Intermediate Similarity	NPC319077
0.8485	Intermediate Similarity	NPC302607
0.8485	Intermediate Similarity	NPC85829
0.8485	Intermediate Similarity	NPC476027
0.8485	Intermediate Similarity	NPC97202
0.8485	Intermediate Similarity	NPC214264
0.8485	Intermediate Similarity	NPC202167
0.8454	Intermediate Similarity	NPC295276
0.8444	Intermediate Similarity	NPC472738
0.8421	Intermediate Similarity	NPC104568
0.8409	Intermediate Similarity	NPC46881
0.8404	Intermediate Similarity	NPC104371
0.8404	Intermediate Similarity	NPC101233
0.8404	Intermediate Similarity	NPC292374
0.8404	Intermediate Similarity	NPC29247
0.8404	Intermediate Similarity	NPC261333
0.8404	Intermediate Similarity	NPC111524
0.8404	Intermediate Similarity	NPC302008
0.8404	Intermediate Similarity	NPC129004
0.8404	Intermediate Similarity	NPC91772
0.8404	Intermediate Similarity	NPC289539
0.8404	Intermediate Similarity	NPC191094
0.8404	Intermediate Similarity	NPC215271
0.8404	Intermediate Similarity	NPC153775
0.84	Intermediate Similarity	NPC220229
0.84	Intermediate Similarity	NPC477916
0.84	Intermediate Similarity	NPC475060
0.8387	Intermediate Similarity	NPC278106
0.8387	Intermediate Similarity	NPC476168
0.8387	Intermediate Similarity	NPC299185
0.8384	Intermediate Similarity	NPC209502
0.8384	Intermediate Similarity	NPC47281
0.8384	Intermediate Similarity	NPC204833
0.8367	Intermediate Similarity	NPC170615
0.8352	Intermediate Similarity	NPC165895
0.8351	Intermediate Similarity	NPC470388
0.8333	Intermediate Similarity	NPC292553
0.8317	Intermediate Similarity	NPC217201
0.8316	Intermediate Similarity	NPC142352
0.8316	Intermediate Similarity	NPC41070
0.83	Intermediate Similarity	NPC149047
0.83	Intermediate Similarity	NPC37600
0.83	Intermediate Similarity	NPC50535
0.8298	Intermediate Similarity	NPC294263
0.8283	Intermediate Similarity	NPC191892
0.8283	Intermediate Similarity	NPC266
0.828	Intermediate Similarity	NPC80401
0.828	Intermediate Similarity	NPC261994
0.828	Intermediate Similarity	NPC470378
0.828	Intermediate Similarity	NPC149761
0.8252	Intermediate Similarity	NPC94650
0.8235	Intermediate Similarity	NPC11710
0.8235	Intermediate Similarity	NPC214644
0.8229	Intermediate Similarity	NPC135548
0.8229	Intermediate Similarity	NPC13949
0.8229	Intermediate Similarity	NPC264979
0.8229	Intermediate Similarity	NPC140242
0.8222	Intermediate Similarity	NPC474482
0.8222	Intermediate Similarity	NPC475745
0.8211	Intermediate Similarity	NPC277399
0.8202	Intermediate Similarity	NPC170985
0.8202	Intermediate Similarity	NPC317066
0.8202	Intermediate Similarity	NPC145143
0.8202	Intermediate Similarity	NPC110780
0.82	Intermediate Similarity	NPC75531
0.82	Intermediate Similarity	NPC149124
0.82	Intermediate Similarity	NPC301787
0.8182	Intermediate Similarity	NPC164999
0.8173	Intermediate Similarity	NPC207251
0.8172	Intermediate Similarity	NPC220498
0.8172	Intermediate Similarity	NPC229871
0.8172	Intermediate Similarity	NPC469319
0.8163	Intermediate Similarity	NPC110149
0.8152	Intermediate Similarity	NPC57469
0.8152	Intermediate Similarity	NPC259009
0.8144	Intermediate Similarity	NPC10864
0.8144	Intermediate Similarity	NPC190554
0.8144	Intermediate Similarity	NPC18509
0.8137	Intermediate Similarity	NPC112895
0.8137	Intermediate Similarity	NPC231278
0.8137	Intermediate Similarity	NPC218123
0.8137	Intermediate Similarity	NPC55973
0.8132	Intermediate Similarity	NPC102292
0.8125	Intermediate Similarity	NPC98639
0.8119	Intermediate Similarity	NPC222833
0.8119	Intermediate Similarity	NPC28791
0.8119	Intermediate Similarity	NPC295366
0.8111	Intermediate Similarity	NPC475726
0.8111	Intermediate Similarity	NPC291320
0.8111	Intermediate Similarity	NPC472743
0.8111	Intermediate Similarity	NPC471036
0.8105	Intermediate Similarity	NPC244356
0.8105	Intermediate Similarity	NPC82138
0.8105	Intermediate Similarity	NPC224060
0.8105	Intermediate Similarity	NPC291373
0.81	Intermediate Similarity	NPC277074
0.81	Intermediate Similarity	NPC469985
0.81	Intermediate Similarity	NPC209298
0.8095	Intermediate Similarity	NPC73300
0.8095	Intermediate Similarity	NPC108721
0.8095	Intermediate Similarity	NPC317210
0.809	Intermediate Similarity	NPC164210
0.809	Intermediate Similarity	NPC157655
0.8085	Intermediate Similarity	NPC46758
0.8081	Intermediate Similarity	NPC39683
0.8081	Intermediate Similarity	NPC60947
0.8081	Intermediate Similarity	NPC252614
0.8077	Intermediate Similarity	NPC56025
0.8065	Intermediate Similarity	NPC16377
0.8065	Intermediate Similarity	NPC474719
0.8061	Intermediate Similarity	NPC38471
0.8061	Intermediate Similarity	NPC162459
0.8061	Intermediate Similarity	NPC98837
0.8061	Intermediate Similarity	NPC89099
0.8061	Intermediate Similarity	NPC20479
0.8061	Intermediate Similarity	NPC28864
0.8061	Intermediate Similarity	NPC38296
0.8046	Intermediate Similarity	NPC138502
0.8046	Intermediate Similarity	NPC307336
0.8046	Intermediate Similarity	NPC260301
0.8043	Intermediate Similarity	NPC34190
0.8041	Intermediate Similarity	NPC256227
0.8041	Intermediate Similarity	NPC29410
0.8041	Intermediate Similarity	NPC200054
0.8041	Intermediate Similarity	NPC234564
0.8039	Intermediate Similarity	NPC67745
0.8039	Intermediate Similarity	NPC86852
0.8039	Intermediate Similarity	NPC165873
0.8039	Intermediate Similarity	NPC166993
0.8039	Intermediate Similarity	NPC471461
0.8039	Intermediate Similarity	NPC251824
0.8022	Intermediate Similarity	NPC255882
0.8022	Intermediate Similarity	NPC263974
0.8021	Intermediate Similarity	NPC64006
0.8019	Intermediate Similarity	NPC326542
0.8	Intermediate Similarity	NPC473424
0.8	Intermediate Similarity	NPC198242
0.8	Intermediate Similarity	NPC211403
0.8	Intermediate Similarity	NPC155304
0.8	Intermediate Similarity	NPC477858
0.8	Intermediate Similarity	NPC250753
0.7981	Intermediate Similarity	NPC473324
0.7981	Intermediate Similarity	NPC471093
0.7981	Intermediate Similarity	NPC76084
0.798	Intermediate Similarity	NPC144956
0.798	Intermediate Similarity	NPC293866
0.798	Intermediate Similarity	NPC154072
0.798	Intermediate Similarity	NPC156324
0.798	Intermediate Similarity	NPC15390
0.798	Intermediate Similarity	NPC55503
0.7961	Intermediate Similarity	NPC89860
0.7961	Intermediate Similarity	NPC273155
0.7961	Intermediate Similarity	NPC65941
0.7961	Intermediate Similarity	NPC189663
0.7961	Intermediate Similarity	NPC63841
0.7957	Intermediate Similarity	NPC269360
0.7957	Intermediate Similarity	NPC264005
0.7955	Intermediate Similarity	NPC472501
0.7941	Intermediate Similarity	NPC200957
0.7941	Intermediate Similarity	NPC130511
0.7941	Intermediate Similarity	NPC138908
0.7941	Intermediate Similarity	NPC307660
0.7938	Intermediate Similarity	NPC205173
0.7938	Intermediate Similarity	NPC210214
0.7938	Intermediate Similarity	NPC266431

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 NPC472496 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	188
0.1-0.2	2068
0.2-0.3	4157
0.3-0.4	1847
0.4-0.5	448
0.5-0.6	185
0.6-0.7	149
0.7-0.8	106
0.8-0.85	2
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	NPD5211	Phase 2
0.8144	Intermediate Similarity	NPD4755	Approved
0.802	Intermediate Similarity	NPD5141	Approved
0.798	Intermediate Similarity	NPD4696	Approved
0.798	Intermediate Similarity	NPD4700	Approved
0.798	Intermediate Similarity	NPD5286	Approved
0.798	Intermediate Similarity	NPD5285	Approved
0.7822	Intermediate Similarity	NPD5224	Approved
0.7822	Intermediate Similarity	NPD4633	Approved
0.7822	Intermediate Similarity	NPD5226	Approved
0.7822	Intermediate Similarity	NPD5225	Approved
0.7789	Intermediate Similarity	NPD5328	Approved
0.7745	Intermediate Similarity	NPD5175	Approved
0.7745	Intermediate Similarity	NPD5174	Approved
0.7742	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD4202	Approved
0.7723	Intermediate Similarity	NPD5223	Approved
0.7717	Intermediate Similarity	NPD4788	Approved
0.7677	Intermediate Similarity	NPD4697	Phase 3
0.766	Intermediate Similarity	NPD3618	Phase 1
0.7642	Intermediate Similarity	NPD4634	Approved
0.7629	Intermediate Similarity	NPD6079	Approved
0.7629	Intermediate Similarity	NPD8035	Phase 2
0.7629	Intermediate Similarity	NPD8034	Phase 2
0.7596	Intermediate Similarity	NPD5739	Approved
0.7596	Intermediate Similarity	NPD6675	Approved
0.7596	Intermediate Similarity	NPD4767	Approved
0.7596	Intermediate Similarity	NPD6402	Approved
0.7596	Intermediate Similarity	NPD7128	Approved
0.7596	Intermediate Similarity	NPD4768	Approved
0.7573	Intermediate Similarity	NPD4754	Approved
0.7547	Intermediate Similarity	NPD6372	Approved
0.7547	Intermediate Similarity	NPD6373	Approved
0.7524	Intermediate Similarity	NPD5697	Approved
0.7524	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD5221	Approved
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD5128	Approved
0.7453	Intermediate Similarity	NPD7320	Approved
0.7453	Intermediate Similarity	NPD4730	Approved
0.7453	Intermediate Similarity	NPD6899	Approved
0.7453	Intermediate Similarity	NPD6881	Approved
0.7453	Intermediate Similarity	NPD4729	Approved
0.7447	Intermediate Similarity	NPD3665	Phase 1
0.7447	Intermediate Similarity	NPD3666	Approved
0.7447	Intermediate Similarity	NPD4786	Approved
0.7447	Intermediate Similarity	NPD3133	Approved
0.7426	Intermediate Similarity	NPD5173	Approved
0.7423	Intermediate Similarity	NPD4753	Phase 2
0.7419	Intermediate Similarity	NPD3667	Approved
0.7416	Intermediate Similarity	NPD3703	Phase 2
0.7407	Intermediate Similarity	NPD6649	Approved
0.7407	Intermediate Similarity	NPD6650	Approved
0.7383	Intermediate Similarity	NPD6013	Approved
0.7383	Intermediate Similarity	NPD6012	Approved
0.7383	Intermediate Similarity	NPD6014	Approved
0.7339	Intermediate Similarity	NPD8297	Approved
0.7315	Intermediate Similarity	NPD6883	Approved
0.7315	Intermediate Similarity	NPD7102	Approved
0.7315	Intermediate Similarity	NPD5247	Approved
0.7315	Intermediate Similarity	NPD5248	Approved
0.7315	Intermediate Similarity	NPD5249	Phase 3
0.7315	Intermediate Similarity	NPD7290	Approved
0.7315	Intermediate Similarity	NPD5251	Approved
0.7315	Intermediate Similarity	NPD5250	Approved
0.729	Intermediate Similarity	NPD6011	Approved
0.7273	Intermediate Similarity	NPD4632	Approved
0.7273	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6116	Phase 1
0.7248	Intermediate Similarity	NPD8130	Phase 1
0.7248	Intermediate Similarity	NPD6847	Approved
0.7248	Intermediate Similarity	NPD6617	Approved
0.7248	Intermediate Similarity	NPD5216	Approved
0.7248	Intermediate Similarity	NPD5215	Approved
0.7248	Intermediate Similarity	NPD6869	Approved
0.7248	Intermediate Similarity	NPD5217	Approved
0.7241	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD3698	Phase 2
0.7241	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5210	Approved
0.7228	Intermediate Similarity	NPD4629	Approved
0.7204	Intermediate Similarity	NPD7525	Registered
0.72	Intermediate Similarity	NPD6399	Phase 3
0.7182	Intermediate Similarity	NPD6882	Approved
0.7159	Intermediate Similarity	NPD4245	Approved
0.7159	Intermediate Similarity	NPD4244	Approved
0.7156	Intermediate Similarity	NPD5135	Approved
0.7156	Intermediate Similarity	NPD5169	Approved
0.7156	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6117	Approved
0.713	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7515	Phase 2
0.7091	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5127	Approved
0.7053	Intermediate Similarity	NPD4221	Approved
0.7053	Intermediate Similarity	NPD4223	Phase 3
0.7043	Intermediate Similarity	NPD6319	Approved
0.6991	Remote Similarity	NPD6274	Approved
0.6989	Remote Similarity	NPD6115	Approved
0.6989	Remote Similarity	NPD6114	Approved
0.6989	Remote Similarity	NPD6118	Approved
0.6989	Remote Similarity	NPD6697	Approved
0.6964	Remote Similarity	NPD8133	Approved
0.6952	Remote Similarity	NPD7639	Approved
0.6952	Remote Similarity	NPD7640	Approved
0.6944	Remote Similarity	NPD6008	Approved
0.6939	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.693	Remote Similarity	NPD6009	Approved
0.693	Remote Similarity	NPD7115	Discovery
0.6923	Remote Similarity	NPD6083	Phase 2
0.6923	Remote Similarity	NPD6084	Phase 2
0.6923	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7902	Approved
0.6907	Remote Similarity	NPD4197	Approved
0.6907	Remote Similarity	NPD3668	Phase 3
0.6903	Remote Similarity	NPD5167	Approved
0.6897	Remote Similarity	NPD6059	Approved
0.6897	Remote Similarity	NPD6054	Approved
0.6891	Remote Similarity	NPD7507	Approved
0.6881	Remote Similarity	NPD6412	Phase 2
0.6857	Remote Similarity	NPD5696	Approved
0.6857	Remote Similarity	NPD7638	Approved
0.6854	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD6015	Approved
0.6838	Remote Similarity	NPD6016	Approved
0.6837	Remote Similarity	NPD5329	Approved
0.6818	Remote Similarity	NPD5168	Approved
0.681	Remote Similarity	NPD7101	Approved
0.681	Remote Similarity	NPD7100	Approved
0.6796	Remote Similarity	NPD7748	Approved
0.6783	Remote Similarity	NPD6317	Approved
0.6782	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.678	Remote Similarity	NPD5988	Approved
0.678	Remote Similarity	NPD6370	Approved
0.6778	Remote Similarity	NPD4789	Approved
0.6774	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD5279	Phase 3
0.6768	Remote Similarity	NPD4690	Approved
0.6768	Remote Similarity	NPD4689	Approved
0.6768	Remote Similarity	NPD5205	Approved
0.6768	Remote Similarity	NPD4138	Approved
0.6768	Remote Similarity	NPD4693	Phase 3
0.6768	Remote Similarity	NPD4688	Approved
0.6765	Remote Similarity	NPD5284	Approved
0.6765	Remote Similarity	NPD5281	Approved
0.6742	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5360	Phase 3
0.6731	Remote Similarity	NPD5695	Phase 3
0.6724	Remote Similarity	NPD6335	Approved
0.6724	Remote Similarity	NPD6313	Approved
0.6724	Remote Similarity	NPD6314	Approved
0.6721	Remote Similarity	NPD7319	Approved
0.6698	Remote Similarity	NPD4225	Approved
0.6697	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD6909	Approved
0.6695	Remote Similarity	NPD6908	Approved
0.6695	Remote Similarity	NPD5983	Phase 2
0.6695	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7492	Approved
0.6639	Remote Similarity	NPD7736	Approved
0.6635	Remote Similarity	NPD7900	Approved
0.6635	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD3671	Phase 1
0.6612	Remote Similarity	NPD6616	Approved
0.6607	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7334	Approved
0.66	Remote Similarity	NPD7521	Approved
0.66	Remote Similarity	NPD6409	Approved
0.66	Remote Similarity	NPD5280	Approved
0.66	Remote Similarity	NPD4694	Approved
0.66	Remote Similarity	NPD6684	Approved
0.66	Remote Similarity	NPD7146	Approved
0.66	Remote Similarity	NPD5690	Phase 2
0.66	Remote Similarity	NPD5330	Approved
0.6598	Remote Similarity	NPD4139	Approved
0.6598	Remote Similarity	NPD4692	Approved
0.6583	Remote Similarity	NPD7604	Phase 2
0.6571	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7645	Phase 2
0.6557	Remote Similarity	NPD7078	Approved
0.6557	Remote Similarity	NPD8293	Discontinued
0.6535	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD4758	Discontinued
0.6517	Remote Similarity	NPD4224	Phase 2
0.6514	Remote Similarity	NPD7632	Discontinued
0.6495	Remote Similarity	NPD5368	Approved
0.6489	Remote Similarity	NPD6942	Approved
0.6489	Remote Similarity	NPD3702	Approved
0.6489	Remote Similarity	NPD7339	Approved
0.6475	Remote Similarity	NPD6336	Discontinued
0.6471	Remote Similarity	NPD6903	Approved
0.6458	Remote Similarity	NPD3617	Approved
0.6446	Remote Similarity	NPD8328	Phase 3
0.6436	Remote Similarity	NPD4519	Discontinued
0.6436	Remote Similarity	NPD4623	Approved
0.6417	Remote Similarity	NPD6921	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