NPASS Compound

Structure

NPC209058 OpenBabel07101719252D 40 46 0 0 1 0 0 0 0 0999 V2000 4.1377 0.9163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4353 -3.1090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8531 0.0183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3643 2.7362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4144 -3.4201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0548 1.8297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9790 0.8459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1356 1.2998 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9110 -1.2538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9110 -0.2960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6241 -1.8841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5396 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6711 -0.3875 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4259 0.2753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7177 -2.1937 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0308 -0.4730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 2.0148 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1501 -0.0966 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6098 -0.9264 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7030 0.1721 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6945 -0.6441 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1431 -1.4273 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5461 -0.7728 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5199 -0.8179 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1870 -1.4846 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5630 -0.7749 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9449 -1.4270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7712 -2.1149 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5498 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2548 0.9233 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.6711 -1.1624 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.9343 2.1999 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3761 -0.3519 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9198 0.7235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3876 -2.6874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0594 -2.7558 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0111 -1.6401 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7081 -2.3141 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6850 1.1084 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 15 1 0 0 0 0 3 16 2 0 0 0 0 4 17 1 0 0 0 0 5 29 1 0 0 0 0 6 30 1 0 0 0 0 7 8 1 0 0 0 0 8 30 1 0 0 0 0 9 10 2 0 0 0 0 9 29 1 0 0 0 0 10 31 1 0 0 0 0 11 15 2 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 20 1 0 0 0 0 13 31 1 0 0 0 0 13 32 1 0 0 0 0 14 21 2 0 0 0 0 16 18 1 0 0 0 0 16 27 1 0 0 0 0 17 33 2 0 0 0 0 17 40 1 0 0 0 0 18 7 1 1 0 0 0 18 24 1 0 0 0 0 19 21 1 0 0 0 0 19 34 2 0 0 0 0 20 23 1 0 0 0 0 20 35 1 1 0 0 0 21 22 1 0 0 0 0 22 15 1 6 0 0 0 22 25 1 0 0 0 0 23 25 1 0 0 0 0 23 32 1 6 0 0 0 24 26 1 0 0 0 0 24 38 1 6 0 0 0 25 39 1 1 0 0 0 26 29 1 1 0 0 0 26 31 1 0 0 0 0 27 36 2 0 0 0 0 27 38 1 0 0 0 0 28 32 1 0 0 0 0 28 37 2 0 0 0 0 28 39 1 0 0 0 0 29 32 1 6 0 0 0 30 31 1 6 0 0 0 30 40 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	548.24
Volume:	551.363
LogP:	2.532
LogD:	1.954
LogS:	-4.418
# Rotatable Bonds:	2
TPSA:	113.04
# H-Bond Aceptor:	8
# H-Bond Donor:	0
# Rings:	7
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.209
Synthetic Accessibility Score:	7.049
Fsp3:	0.656
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	3
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.04
MDCK Permeability:	4.4540058297570795e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.028
20% Bioavailability (F20%):	0.641
30% Bioavailability (F30%):	0.849

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.949
Plasma Protein Binding (PPB):	83.06880187988281%
Volume Distribution (VD):	0.34
Pgp-substrate:	25.902524948120117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.888
CYP2C19-inhibitor:	0.172
CYP2C19-substrate:	0.83
CYP2C9-inhibitor:	0.161
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.863

ADMET: Excretion

Clearance (CL):	11.992
Half-life (T1/2):	0.042

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.038
Drug-inuced Liver Injury (DILI):	0.179
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.975
Maximum Recommended Daily Dose:	0.359
Skin Sensitization:	0.097
Carcinogencity:	0.818
Eye Corrosion:	0.066
Eye Irritation:	0.088
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC209058

Natural Product ID:	NPC209058
*Common Name:**	Artanomalide D
IUPAC Name:	n.a.
Synonyms:	Artanomalide D
Standard InCHIKey:	VFJMOBCSAQZZGH-UPBIVHIMSA-N
Standard InCHI:	InChI=1S/C32H36O8/c1-14-12-20(35)23-25(22-15(2)11-19(34)21(14)22)39-28(37)32(23)13-31-10-9-29(32,5)26(31)24-18(16(3)27(36)38-24)7-8-30(31,6)40-17(4)33/h9-11,18,20,22-26,35H,3,7-8,12-13H2,1-2,4-6H3/t18-,20-,22-,23+,24-,25+,26-,29+,30-,31?,32?/m0/s1
SMILES:	CC1=C2C(=O)C=C(C)[C@@H]2[C@@H]2[C@@H]([C@H](C1)O)C1(CC34C=C[C@]1(C)[C@@H]3[C@@H]1[C@@H](CC[C@]4(C)OC(=O)C)C(=C)C(=O)O1)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1076802
PubChem CID:	44627812
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids

*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
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20000780]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19755	Artemisia anomala	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19755	Artemisia anomala	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
IC50	4
Others	1

Activity Type	# Activity
Cell Line	4
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT180	Cell Line	HCT-8	Homo sapiens	IC50	=	1900.0	nM	PMID[516707]
NPT547	Cell Line	BGC-823	Homo sapiens	IC50	=	8500.0	nM	PMID[516707]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	1800.0	nM	PMID[516707]
NPT181	Cell Line	Bel-7402	Homo sapiens	IC50	=	3000.0	nM	PMID[516707]
NPT31	Individual Protein	Cyclooxygenase-2	Homo sapiens	Inhibition	=	99.5	%	PMID[516707]

☑ 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 NPC209058 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	267
0.1-0.2	1648
0.2-0.3	6148
0.3-0.4	13800
0.4-0.5	10556
0.5-0.6	7161
0.6-0.7	2699
0.7-0.8	390
0.8-0.85	12
0.85-0.9	5
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC471884
0.8929	High Similarity	NPC161060
0.8839	High Similarity	NPC36754
0.8661	High Similarity	NPC471382
0.8496	Intermediate Similarity	NPC471380
0.844	Intermediate Similarity	NPC475217
0.8378	Intermediate Similarity	NPC475588
0.8273	Intermediate Similarity	NPC252234
0.8235	Intermediate Similarity	NPC1538
0.8235	Intermediate Similarity	NPC42747
0.819	Intermediate Similarity	NPC477131
0.8182	Intermediate Similarity	NPC203659
0.8174	Intermediate Similarity	NPC123117
0.8173	Intermediate Similarity	NPC133698
0.8173	Intermediate Similarity	NPC131209
0.8167	Intermediate Similarity	NPC144625
0.8165	Intermediate Similarity	NPC225353
0.8165	Intermediate Similarity	NPC86077
0.8151	Intermediate Similarity	NPC192309
0.8131	Intermediate Similarity	NPC169205
0.8113	Intermediate Similarity	NPC48803
0.8113	Intermediate Similarity	NPC90121
0.8113	Intermediate Similarity	NPC304886
0.8113	Intermediate Similarity	NPC275960
0.8113	Intermediate Similarity	NPC193645
0.8095	Intermediate Similarity	NPC135776
0.8091	Intermediate Similarity	NPC110989
0.8073	Intermediate Similarity	NPC171759
0.8056	Intermediate Similarity	NPC141191
0.8049	Intermediate Similarity	NPC13071
0.8037	Intermediate Similarity	NPC185553
0.8019	Intermediate Similarity	NPC198853
0.7982	Intermediate Similarity	NPC477103
0.7967	Intermediate Similarity	NPC172823
0.7963	Intermediate Similarity	NPC170143
0.7963	Intermediate Similarity	NPC108475
0.7963	Intermediate Similarity	NPC161493
0.7963	Intermediate Similarity	NPC213947
0.7946	Intermediate Similarity	NPC243998
0.7946	Intermediate Similarity	NPC223450
0.7944	Intermediate Similarity	NPC67584
0.7944	Intermediate Similarity	NPC52044
0.7913	Intermediate Similarity	NPC287311
0.7895	Intermediate Similarity	NPC477102
0.7886	Intermediate Similarity	NPC11732
0.7885	Intermediate Similarity	NPC178875
0.7881	Intermediate Similarity	NPC475323
0.787	Intermediate Similarity	NPC18019
0.787	Intermediate Similarity	NPC24956
0.787	Intermediate Similarity	NPC213078
0.787	Intermediate Similarity	NPC142529
0.787	Intermediate Similarity	NPC91771
0.7863	Intermediate Similarity	NPC133677
0.7863	Intermediate Similarity	NPC138303
0.7863	Intermediate Similarity	NPC67290
0.7857	Intermediate Similarity	NPC100487
0.7857	Intermediate Similarity	NPC224623
0.785	Intermediate Similarity	NPC470010
0.785	Intermediate Similarity	NPC323008
0.785	Intermediate Similarity	NPC470013
0.785	Intermediate Similarity	NPC262133
0.7845	Intermediate Similarity	NPC76550
0.7845	Intermediate Similarity	NPC123855
0.7845	Intermediate Similarity	NPC23967
0.7838	Intermediate Similarity	NPC474747
0.783	Intermediate Similarity	NPC70595
0.783	Intermediate Similarity	NPC150978
0.783	Intermediate Similarity	NPC74103
0.783	Intermediate Similarity	NPC123177
0.7826	Intermediate Similarity	NPC257240
0.7818	Intermediate Similarity	NPC280963
0.781	Intermediate Similarity	NPC32922
0.7788	Intermediate Similarity	NPC291643
0.7788	Intermediate Similarity	NPC118601
0.7787	Intermediate Similarity	NPC186339
0.7787	Intermediate Similarity	NPC129992
0.7778	Intermediate Similarity	NPC213698
0.7778	Intermediate Similarity	NPC163228
0.7778	Intermediate Similarity	NPC46269
0.7778	Intermediate Similarity	NPC106395
0.7768	Intermediate Similarity	NPC475945
0.7768	Intermediate Similarity	NPC475871
0.7757	Intermediate Similarity	NPC473263
0.7757	Intermediate Similarity	NPC473234
0.7757	Intermediate Similarity	NPC60386
0.7757	Intermediate Similarity	NPC473273
0.7757	Intermediate Similarity	NPC308656
0.7757	Intermediate Similarity	NPC153590
0.7748	Intermediate Similarity	NPC150923
0.7748	Intermediate Similarity	NPC477950
0.7739	Intermediate Similarity	NPC273433
0.7736	Intermediate Similarity	NPC54065
0.7736	Intermediate Similarity	NPC297474
0.7736	Intermediate Similarity	NPC253144
0.7736	Intermediate Similarity	NPC129419
0.7731	Intermediate Similarity	NPC471145
0.7731	Intermediate Similarity	NPC473656
0.7719	Intermediate Similarity	NPC26617
0.7714	Intermediate Similarity	NPC91248
0.7706	Intermediate Similarity	NPC126156
0.7699	Intermediate Similarity	NPC309190
0.7698	Intermediate Similarity	NPC469351
0.7692	Intermediate Similarity	NPC236692
0.7692	Intermediate Similarity	NPC309757
0.7692	Intermediate Similarity	NPC138757
0.7686	Intermediate Similarity	NPC163693
0.7686	Intermediate Similarity	NPC147635
0.7685	Intermediate Similarity	NPC127019
0.7685	Intermediate Similarity	NPC167219
0.7685	Intermediate Similarity	NPC289004
0.7672	Intermediate Similarity	NPC474923
0.7672	Intermediate Similarity	NPC48305
0.7664	Intermediate Similarity	NPC171360
0.7664	Intermediate Similarity	NPC293001
0.7664	Intermediate Similarity	NPC284185
0.7664	Intermediate Similarity	NPC184463
0.7664	Intermediate Similarity	NPC12172
0.7664	Intermediate Similarity	NPC133888
0.7664	Intermediate Similarity	NPC29821
0.7664	Intermediate Similarity	NPC35959
0.7664	Intermediate Similarity	NPC475925
0.7664	Intermediate Similarity	NPC57304
0.7664	Intermediate Similarity	NPC63193
0.7664	Intermediate Similarity	NPC208886
0.7664	Intermediate Similarity	NPC221282
0.7652	Intermediate Similarity	NPC308191
0.7642	Intermediate Similarity	NPC168679
0.7642	Intermediate Similarity	NPC117405
0.7642	Intermediate Similarity	NPC268298
0.7642	Intermediate Similarity	NPC155935
0.7642	Intermediate Similarity	NPC12872
0.7642	Intermediate Similarity	NPC215556
0.7642	Intermediate Similarity	NPC52198
0.7636	Intermediate Similarity	NPC477949
0.7632	Intermediate Similarity	NPC166115
0.7632	Intermediate Similarity	NPC54737
0.7632	Intermediate Similarity	NPC179891
0.7615	Intermediate Similarity	NPC37408
0.7615	Intermediate Similarity	NPC170120
0.7615	Intermediate Similarity	NPC36954
0.7607	Intermediate Similarity	NPC474750
0.7596	Intermediate Similarity	NPC161957
0.7593	Intermediate Similarity	NPC179746
0.7593	Intermediate Similarity	NPC476300
0.7593	Intermediate Similarity	NPC81419
0.7593	Intermediate Similarity	NPC200237
0.7589	Intermediate Similarity	NPC474742
0.7586	Intermediate Similarity	NPC59489
0.7586	Intermediate Similarity	NPC139838
0.7583	Intermediate Similarity	NPC471146
0.7583	Intermediate Similarity	NPC475305
0.757	Intermediate Similarity	NPC62815
0.757	Intermediate Similarity	NPC35809
0.757	Intermediate Similarity	NPC301969
0.757	Intermediate Similarity	NPC37607
0.757	Intermediate Similarity	NPC216284
0.7568	Intermediate Similarity	NPC221615
0.7565	Intermediate Similarity	NPC470192
0.7563	Intermediate Similarity	NPC474181
0.7547	Intermediate Similarity	NPC207114
0.7547	Intermediate Similarity	NPC217983
0.7547	Intermediate Similarity	NPC202672
0.7547	Intermediate Similarity	NPC79549
0.7545	Intermediate Similarity	NPC476315
0.7544	Intermediate Similarity	NPC474741
0.7542	Intermediate Similarity	NPC189338
0.7542	Intermediate Similarity	NPC95290
0.7542	Intermediate Similarity	NPC35069
0.7542	Intermediate Similarity	NPC258711
0.7541	Intermediate Similarity	NPC19336
0.7541	Intermediate Similarity	NPC185876
0.7524	Intermediate Similarity	NPC107787
0.7524	Intermediate Similarity	NPC67493
0.7523	Intermediate Similarity	NPC473331
0.7523	Intermediate Similarity	NPC90453
0.7522	Intermediate Similarity	NPC471757
0.7522	Intermediate Similarity	NPC66110
0.7522	Intermediate Similarity	NPC78127
0.7522	Intermediate Similarity	NPC472754
0.7521	Intermediate Similarity	NPC146280
0.7521	Intermediate Similarity	NPC475372
0.7521	Intermediate Similarity	NPC475401
0.7521	Intermediate Similarity	NPC124676
0.75	Intermediate Similarity	NPC277583
0.75	Intermediate Similarity	NPC261607
0.75	Intermediate Similarity	NPC191339
0.75	Intermediate Similarity	NPC469352
0.75	Intermediate Similarity	NPC115786
0.75	Intermediate Similarity	NPC184063
0.75	Intermediate Similarity	NPC475960
0.75	Intermediate Similarity	NPC286341
0.75	Intermediate Similarity	NPC30515
0.75	Intermediate Similarity	NPC290651
0.75	Intermediate Similarity	NPC148458
0.75	Intermediate Similarity	NPC111114
0.75	Intermediate Similarity	NPC165287
0.75	Intermediate Similarity	NPC300312
0.748	Intermediate Similarity	NPC473228
0.748	Intermediate Similarity	NPC470829
0.7479	Intermediate Similarity	NPC474937

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 NPC209058 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	275
0.1-0.2	2277
0.2-0.3	4061
0.3-0.4	1801
0.4-0.5	419
0.5-0.6	250
0.6-0.7	62
0.7-0.8	5
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8113	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD6371	Approved
0.7719	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD1695	Approved
0.7107	Intermediate Similarity	NPD6053	Discontinued
0.7091	Intermediate Similarity	NPD5785	Approved
0.7054	Intermediate Similarity	NPD5282	Discontinued
0.6885	Remote Similarity	NPD6649	Approved
0.6885	Remote Similarity	NPD6650	Approved
0.6829	Remote Similarity	NPD8297	Approved
0.6822	Remote Similarity	NPD6435	Approved
0.6786	Remote Similarity	NPD6698	Approved
0.6786	Remote Similarity	NPD46	Approved
0.6786	Remote Similarity	NPD7838	Discovery
0.6777	Remote Similarity	NPD6881	Approved
0.6777	Remote Similarity	NPD6899	Approved
0.6759	Remote Similarity	NPD5362	Discontinued
0.675	Remote Similarity	NPD6008	Approved
0.6748	Remote Similarity	NPD8130	Phase 1
0.6726	Remote Similarity	NPD7983	Approved
0.6721	Remote Similarity	NPD6373	Approved
0.6721	Remote Similarity	NPD6372	Approved
0.6694	Remote Similarity	NPD5697	Approved
0.6694	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4250	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7078	Approved
0.6667	Remote Similarity	NPD4251	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6641	Remote Similarity	NPD7492	Approved
0.6639	Remote Similarity	NPD7320	Approved
0.6639	Remote Similarity	NPD6686	Approved
0.6636	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5363	Approved
0.6636	Remote Similarity	NPD5368	Approved
0.6617	Remote Similarity	NPD7736	Approved
0.6614	Remote Similarity	NPD7115	Discovery
0.6613	Remote Similarity	NPD6847	Approved
0.6613	Remote Similarity	NPD6617	Approved
0.6613	Remote Similarity	NPD6869	Approved
0.6612	Remote Similarity	NPD7128	Approved
0.6612	Remote Similarity	NPD6675	Approved
0.6612	Remote Similarity	NPD6402	Approved
0.6612	Remote Similarity	NPD5739	Approved
0.6604	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD6616	Approved
0.6591	Remote Similarity	NPD7507	Approved
0.6589	Remote Similarity	NPD6319	Approved
0.6589	Remote Similarity	NPD6054	Approved
0.6585	Remote Similarity	NPD6014	Approved
0.6585	Remote Similarity	NPD6012	Approved
0.6585	Remote Similarity	NPD6013	Approved
0.6577	Remote Similarity	NPD4249	Approved
0.6577	Remote Similarity	NPD5786	Approved
0.6574	Remote Similarity	NPD5369	Approved
0.6525	Remote Similarity	NPD7638	Approved
0.6525	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6399	Phase 3
0.6508	Remote Similarity	NPD4632	Approved
0.6504	Remote Similarity	NPD6011	Approved
0.6489	Remote Similarity	NPD6370	Approved
0.6486	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.648	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7639	Approved
0.6471	Remote Similarity	NPD7640	Approved
0.6455	Remote Similarity	NPD7154	Phase 3
0.6444	Remote Similarity	NPD7319	Approved
0.6441	Remote Similarity	NPD6084	Phase 2
0.6441	Remote Similarity	NPD6083	Phase 2
0.6423	Remote Similarity	NPD5701	Approved
0.6418	Remote Similarity	NPD8293	Discontinued
0.6412	Remote Similarity	NPD6016	Approved
0.6412	Remote Similarity	NPD6015	Approved
0.6379	Remote Similarity	NPD5778	Approved
0.6379	Remote Similarity	NPD5779	Approved
0.6364	Remote Similarity	NPD5988	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6364	Remote Similarity	NPD4270	Approved
0.6364	Remote Similarity	NPD4269	Approved
0.6357	Remote Similarity	NPD6009	Approved
0.635	Remote Similarity	NPD7260	Phase 2
0.6339	Remote Similarity	NPD1694	Approved
0.6336	Remote Similarity	NPD6059	Approved
0.6333	Remote Similarity	NPD4696	Approved
0.6333	Remote Similarity	NPD5285	Approved
0.6333	Remote Similarity	NPD5286	Approved
0.633	Remote Similarity	NPD4822	Approved
0.633	Remote Similarity	NPD4821	Approved
0.633	Remote Similarity	NPD4820	Approved
0.633	Remote Similarity	NPD4819	Approved
0.633	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7604	Phase 2
0.6293	Remote Similarity	NPD6411	Approved
0.6293	Remote Similarity	NPD7637	Suspended
0.6293	Remote Similarity	NPD6079	Approved
0.6288	Remote Similarity	NPD5983	Phase 2
0.6288	Remote Similarity	NPD8516	Approved
0.6288	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6288	Remote Similarity	NPD8517	Approved
0.6288	Remote Similarity	NPD8515	Approved
0.6288	Remote Similarity	NPD8513	Phase 3
0.6273	Remote Similarity	NPD4790	Discontinued
0.6271	Remote Similarity	NPD5695	Phase 3
0.626	Remote Similarity	NPD7100	Approved
0.626	Remote Similarity	NPD5141	Approved
0.626	Remote Similarity	NPD7101	Approved
0.625	Remote Similarity	NPD5696	Approved
0.625	Remote Similarity	NPD4225	Approved
0.623	Remote Similarity	NPD5225	Approved
0.623	Remote Similarity	NPD5224	Approved
0.623	Remote Similarity	NPD5226	Approved
0.623	Remote Similarity	NPD4633	Approved
0.6222	Remote Similarity	NPD6336	Discontinued
0.622	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7839	Suspended
0.6187	Remote Similarity	NPD6845	Suspended
0.6183	Remote Similarity	NPD6335	Approved
0.6182	Remote Similarity	NPD4252	Approved
0.6179	Remote Similarity	NPD5175	Approved
0.6179	Remote Similarity	NPD5174	Approved
0.6167	Remote Similarity	NPD4755	Approved
0.6165	Remote Similarity	NPD8033	Approved
0.6161	Remote Similarity	NPD5331	Approved
0.6161	Remote Similarity	NPD5332	Approved
0.616	Remote Similarity	NPD6412	Phase 2
0.6154	Remote Similarity	NPD5284	Approved
0.6154	Remote Similarity	NPD6274	Approved
0.6154	Remote Similarity	NPD5281	Approved
0.6148	Remote Similarity	NPD5344	Discontinued
0.6148	Remote Similarity	NPD5223	Approved
0.6147	Remote Similarity	NPD4271	Approved
0.6147	Remote Similarity	NPD4268	Approved
0.6142	Remote Similarity	NPD4634	Approved
0.6134	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5210	Approved
0.6134	Remote Similarity	NPD4629	Approved
0.6121	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD5328	Approved
0.6121	Remote Similarity	NPD6101	Approved
0.6111	Remote Similarity	NPD4729	Approved
0.6111	Remote Similarity	NPD4730	Approved
0.6111	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD6317	Approved
0.6106	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.609	Remote Similarity	NPD8294	Approved
0.609	Remote Similarity	NPD8377	Approved
0.6083	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6083	Remote Similarity	NPD5221	Approved
0.6083	Remote Similarity	NPD5222	Approved
0.6071	Remote Similarity	NPD5209	Approved
0.6071	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5207	Approved
0.6066	Remote Similarity	NPD4700	Approved
0.6061	Remote Similarity	NPD6314	Approved
0.6061	Remote Similarity	NPD7328	Approved
0.6061	Remote Similarity	NPD7327	Approved
0.6061	Remote Similarity	NPD6313	Approved
0.6058	Remote Similarity	NPD8074	Phase 3
0.6045	Remote Similarity	NPD8269	Approved
0.6045	Remote Similarity	NPD8378	Approved
0.6045	Remote Similarity	NPD8267	Approved
0.6045	Remote Similarity	NPD8296	Approved
0.6045	Remote Similarity	NPD8380	Approved
0.6045	Remote Similarity	NPD8268	Approved
0.6045	Remote Similarity	NPD8379	Approved
0.6045	Remote Similarity	NPD8266	Approved
0.6045	Remote Similarity	NPD8335	Approved
0.6045	Remote Similarity	NPD7503	Approved
0.6034	Remote Similarity	NPD6903	Approved
0.6034	Remote Similarity	NPD6672	Approved
0.6034	Remote Similarity	NPD5737	Approved
0.6033	Remote Similarity	NPD7902	Approved
0.6033	Remote Similarity	NPD5173	Approved
0.6031	Remote Similarity	NPD6868	Approved
0.6018	Remote Similarity	NPD6695	Phase 3
0.6017	Remote Similarity	NPD5693	Phase 1
0.6016	Remote Similarity	NPD5250	Approved
0.6016	Remote Similarity	NPD5251	Approved
0.6016	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6016	Remote Similarity	NPD5249	Phase 3
0.6016	Remote Similarity	NPD5248	Approved
0.6016	Remote Similarity	NPD5247	Approved
0.6015	Remote Similarity	NPD7516	Approved
0.6014	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5330	Approved
0.6	Remote Similarity	NPD8133	Approved
0.6	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6409	Approved
0.6	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6	Remote Similarity	NPD7334	Approved
0.6	Remote Similarity	NPD7146	Approved
0.6	Remote Similarity	NPD7521	Approved
0.6	Remote Similarity	NPD6684	Approved
0.5983	Remote Similarity	NPD4753	Phase 2
0.5968	Remote Similarity	NPD7632	Discontinued
0.5965	Remote Similarity	NPD4786	Approved
0.5956	Remote Similarity	NPD7642	Approved
0.5956	Remote Similarity	NPD8328	Phase 3
0.5952	Remote Similarity	NPD4768	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