NPASS Compound

Structure

NPC280566 OpenBabel07101718242D 39 43 0 0 1 0 0 0 0 0999 V2000 10.0450 -2.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5809 -2.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5809 -5.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3820 -4.0784 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4589 -1.2806 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3412 -1.8804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3950 -3.9068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1790 -4.0978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1747 0.5653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3129 -4.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3746 1.1651 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8488 -4.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9828 -4.0978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2718 -2.6802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1858 -0.6275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6409 -1.6196 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1790 -3.0978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7149 -3.0978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5809 -4.5978 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5393 -3.5400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2046 -0.4342 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7149 -4.0978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8488 -2.5978 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4469 -4.0978 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4717 -2.0804 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2397 -2.4286 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4418 -1.0808 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3129 -2.5978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4606 -0.8876 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9828 -3.0978 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6464 -1.5151 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3483 -4.0007 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2399 1.6764 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3129 -1.5978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9485 -0.7989 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5841 -2.5410 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4469 -3.0978 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 2 0 0 0 0 4 20 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 8 10 1 0 0 0 0 8 17 2 0 0 0 0 9 11 2 0 0 0 0 9 21 1 0 0 0 0 10 24 1 0 0 0 0 11 27 1 0 0 0 0 12 13 1 0 0 0 0 12 22 2 0 0 0 0 13 31 1 0 0 0 0 14 25 1 0 0 0 0 14 26 1 0 0 0 0 15 21 2 0 0 0 0 15 32 1 0 0 0 0 16 23 1 0 0 0 0 16 32 1 0 0 0 0 17 29 1 0 0 0 0 18 22 1 0 0 0 0 18 23 1 0 0 0 0 19 3 1 6 0 0 0 19 22 1 0 0 0 0 20 33 2 0 0 0 0 20 37 1 0 0 0 0 23 31 1 1 0 0 0 24 19 1 6 0 0 0 24 38 1 0 0 0 0 25 28 1 0 0 0 0 25 37 1 1 0 0 0 26 31 1 6 0 0 0 26 32 1 0 0 0 0 27 34 2 0 0 0 0 27 39 1 0 0 0 0 28 21 1 1 0 0 0 28 30 1 0 0 0 0 29 35 2 0 0 0 0 29 38 1 0 0 0 0 30 39 1 0 0 0 0 31 7 1 6 0 0 0 32 36 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	536.28
Volume:	559.686
LogP:	4.789
LogD:	2.653
LogS:	-4.454
# Rotatable Bonds:	4
TPSA:	99.13
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.315
Synthetic Accessibility Score:	5.906
Fsp3:	0.594
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.903
MDCK Permeability:	1.9843722839141265e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.023
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.305
Plasma Protein Binding (PPB):	93.04302978515625%
Volume Distribution (VD):	2.869
Pgp-substrate:	7.502985954284668%

ADMET: Metabolism

CYP1A2-inhibitor:	0.09
CYP1A2-substrate:	0.068
CYP2C19-inhibitor:	0.358
CYP2C19-substrate:	0.104
CYP2C9-inhibitor:	0.748
CYP2C9-substrate:	0.031
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.034
CYP3A4-inhibitor:	0.839
CYP3A4-substrate:	0.38

ADMET: Excretion

Clearance (CL):	2.688
Half-life (T1/2):	0.318

ADMET: Toxicity

hERG Blockers:	0.199
Human Hepatotoxicity (H-HT):	0.779
Drug-inuced Liver Injury (DILI):	0.138
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.921
Maximum Recommended Daily Dose:	0.952
Skin Sensitization:	0.797
Carcinogencity:	0.047
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC280566

Natural Product ID:	NPC280566
*Common Name:**	Logipedlactone J
IUPAC Name:	n.a.
Synonyms:	Logipedlactone J
Standard InCHIKey:	VPYOIPWGVNGDBV-XVLJLTBWSA-N
Standard InCHI:	InChI=1S/C32H40O7/c1-17-8-10-24(38-29(17)35)19(3)22-12-13-31(7)23(18(22)2)16-32(36)15-21-9-11-27(34)39-30(5,6)28(21)25(14-26(31)32)37-20(4)33/h8-9,11-12,15,19,23-26,28,36H,2,10,13-14,16H2,1,3-7H3/t19-,23+,24-,25-,26+,28+,31-,32-/m1/s1
SMILES:	CC(=O)O[C@@H]1C[C@@H]2[C@](C=C3[C@@H]1C(C)(C)OC(=O)C=C3)(O)C[C@@H]1[C@@]2(C)CC=C(C1=C)[C@H]([C@H]1CC=C(C(=O)O1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077104
PubChem CID:	24854383
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15165154]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	Stems	n.a.	n.a.	PMID[20025236]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	seed	n.a.	PMID[21381710]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27599	Kadsura ananosma	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2000.0	nM	PMID[469648]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[469648]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[469648]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	5300.0	nM	PMID[469648]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	2800.0	nM	PMID[469648]

☑ 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 NPC280566 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	196
0.1-0.2	1107
0.2-0.3	4427
0.3-0.4	12649
0.4-0.5	12026
0.5-0.6	7589
0.6-0.7	4136
0.7-0.8	517
0.8-0.85	19
0.85-0.9	9
0.9-0.95	19
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9792	High Similarity	NPC183570
0.9691	High Similarity	NPC272632
0.9684	High Similarity	NPC290802
0.9278	High Similarity	NPC227865
0.9216	High Similarity	NPC238850
0.9118	High Similarity	NPC475274
0.9029	High Similarity	NPC181298
0.899	High Similarity	NPC298233
0.8958	High Similarity	NPC471994
0.8958	High Similarity	NPC120351
0.8958	High Similarity	NPC166143
0.8942	High Similarity	NPC255401
0.8942	High Similarity	NPC471484
0.8942	High Similarity	NPC262083
0.8942	High Similarity	NPC284162
0.8857	High Similarity	NPC241477
0.8846	High Similarity	NPC15551
0.8762	High Similarity	NPC71680
0.8687	High Similarity	NPC202705
0.8349	Intermediate Similarity	NPC43213
0.8182	Intermediate Similarity	NPC216665
0.8173	Intermediate Similarity	NPC471993
0.8095	Intermediate Similarity	NPC297617
0.8077	Intermediate Similarity	NPC99411
0.8077	Intermediate Similarity	NPC146822
0.8056	Intermediate Similarity	NPC75389
0.8019	Intermediate Similarity	NPC309190
0.8	Intermediate Similarity	NPC475320
0.7963	Intermediate Similarity	NPC275060
0.7963	Intermediate Similarity	NPC220155
0.7961	Intermediate Similarity	NPC141401
0.7941	Intermediate Similarity	NPC20546
0.7925	Intermediate Similarity	NPC85742
0.789	Intermediate Similarity	NPC137911
0.789	Intermediate Similarity	NPC228477
0.7885	Intermediate Similarity	NPC64742
0.7885	Intermediate Similarity	NPC65700
0.787	Intermediate Similarity	NPC469959
0.787	Intermediate Similarity	NPC472263
0.787	Intermediate Similarity	NPC469957
0.787	Intermediate Similarity	NPC108682
0.7843	Intermediate Similarity	NPC7165
0.7838	Intermediate Similarity	NPC191620
0.7838	Intermediate Similarity	NPC44537
0.7822	Intermediate Similarity	NPC177641
0.7818	Intermediate Similarity	NPC16270
0.781	Intermediate Similarity	NPC241221
0.78	Intermediate Similarity	NPC177141
0.7788	Intermediate Similarity	NPC469432
0.7778	Intermediate Similarity	NPC469960
0.7778	Intermediate Similarity	NPC295843
0.7778	Intermediate Similarity	NPC93026
0.7778	Intermediate Similarity	NPC265502
0.7778	Intermediate Similarity	NPC29389
0.7757	Intermediate Similarity	NPC171014
0.7748	Intermediate Similarity	NPC474315
0.7748	Intermediate Similarity	NPC470076
0.7745	Intermediate Similarity	NPC38232
0.7736	Intermediate Similarity	NPC244456
0.7736	Intermediate Similarity	NPC469657
0.7723	Intermediate Similarity	NPC273199
0.7714	Intermediate Similarity	NPC166745
0.7714	Intermediate Similarity	NPC235464
0.7714	Intermediate Similarity	NPC98868
0.7706	Intermediate Similarity	NPC43063
0.7706	Intermediate Similarity	NPC91034
0.7706	Intermediate Similarity	NPC79298
0.7699	Intermediate Similarity	NPC305044
0.7699	Intermediate Similarity	NPC265290
0.7692	Intermediate Similarity	NPC9812
0.7692	Intermediate Similarity	NPC190713
0.7679	Intermediate Similarity	NPC100267
0.7679	Intermediate Similarity	NPC475524
0.7679	Intermediate Similarity	NPC221144
0.767	Intermediate Similarity	NPC469491
0.7664	Intermediate Similarity	NPC114540
0.7664	Intermediate Similarity	NPC32577
0.7664	Intermediate Similarity	NPC155332
0.7658	Intermediate Similarity	NPC12795
0.7652	Intermediate Similarity	NPC288679
0.7647	Intermediate Similarity	NPC45269
0.7642	Intermediate Similarity	NPC13743
0.7642	Intermediate Similarity	NPC98813
0.7636	Intermediate Similarity	NPC137462
0.7636	Intermediate Similarity	NPC304276
0.7632	Intermediate Similarity	NPC470075
0.7632	Intermediate Similarity	NPC148458
0.7619	Intermediate Similarity	NPC99726
0.7611	Intermediate Similarity	NPC241977
0.7611	Intermediate Similarity	NPC101965
0.7611	Intermediate Similarity	NPC171126
0.7611	Intermediate Similarity	NPC101400
0.76	Intermediate Similarity	NPC45957
0.76	Intermediate Similarity	NPC471657
0.7596	Intermediate Similarity	NPC171395
0.7596	Intermediate Similarity	NPC281134
0.7596	Intermediate Similarity	NPC293052
0.7593	Intermediate Similarity	NPC473283
0.7593	Intermediate Similarity	NPC72151
0.7593	Intermediate Similarity	NPC475526
0.7593	Intermediate Similarity	NPC329345
0.7589	Intermediate Similarity	NPC470961
0.7586	Intermediate Similarity	NPC270850
0.7586	Intermediate Similarity	NPC305260
0.7576	Intermediate Similarity	NPC471185
0.7573	Intermediate Similarity	NPC205034
0.7573	Intermediate Similarity	NPC162615
0.7573	Intermediate Similarity	NPC152778
0.7573	Intermediate Similarity	NPC214697
0.757	Intermediate Similarity	NPC206079
0.757	Intermediate Similarity	NPC115899
0.757	Intermediate Similarity	NPC116139
0.7568	Intermediate Similarity	NPC47951
0.7565	Intermediate Similarity	NPC185287
0.7565	Intermediate Similarity	NPC157380
0.7551	Intermediate Similarity	NPC474809
0.7549	Intermediate Similarity	NPC123854
0.7549	Intermediate Similarity	NPC182136
0.7547	Intermediate Similarity	NPC92275
0.7547	Intermediate Similarity	NPC244411
0.7547	Intermediate Similarity	NPC181147
0.7545	Intermediate Similarity	NPC476958
0.7545	Intermediate Similarity	NPC475294
0.7544	Intermediate Similarity	NPC67290
0.7544	Intermediate Similarity	NPC138303
0.7544	Intermediate Similarity	NPC133677
0.7525	Intermediate Similarity	NPC473879
0.7525	Intermediate Similarity	NPC60765
0.7524	Intermediate Similarity	NPC16967
0.7523	Intermediate Similarity	NPC200861
0.7523	Intermediate Similarity	NPC473577
0.7523	Intermediate Similarity	NPC472822
0.7523	Intermediate Similarity	NPC472868
0.7523	Intermediate Similarity	NPC475585
0.7523	Intermediate Similarity	NPC474550
0.7522	Intermediate Similarity	NPC313921
0.7522	Intermediate Similarity	NPC236217
0.7522	Intermediate Similarity	NPC123855
0.7522	Intermediate Similarity	NPC98038
0.7522	Intermediate Similarity	NPC76550
0.7522	Intermediate Similarity	NPC138757
0.7521	Intermediate Similarity	NPC114939
0.7521	Intermediate Similarity	NPC145074
0.7521	Intermediate Similarity	NPC474370
0.7521	Intermediate Similarity	NPC41123
0.75	Intermediate Similarity	NPC16701
0.75	Intermediate Similarity	NPC477668
0.75	Intermediate Similarity	NPC473627
0.75	Intermediate Similarity	NPC66110
0.75	Intermediate Similarity	NPC104925
0.75	Intermediate Similarity	NPC298973
0.75	Intermediate Similarity	NPC29133
0.75	Intermediate Similarity	NPC320447
0.75	Intermediate Similarity	NPC153440
0.75	Intermediate Similarity	NPC103491
0.75	Intermediate Similarity	NPC37116
0.7479	Intermediate Similarity	NPC6193
0.7478	Intermediate Similarity	NPC190286
0.7477	Intermediate Similarity	NPC473510
0.7477	Intermediate Similarity	NPC470024
0.7477	Intermediate Similarity	NPC473482
0.7477	Intermediate Similarity	NPC475418
0.7477	Intermediate Similarity	NPC79631
0.7477	Intermediate Similarity	NPC266955
0.7477	Intermediate Similarity	NPC318363
0.7476	Intermediate Similarity	NPC212948
0.7476	Intermediate Similarity	NPC474018
0.7476	Intermediate Similarity	NPC473986
0.7474	Intermediate Similarity	NPC476439
0.7458	Intermediate Similarity	NPC46570
0.7458	Intermediate Similarity	NPC312481
0.7456	Intermediate Similarity	NPC46269
0.7456	Intermediate Similarity	NPC122056
0.7456	Intermediate Similarity	NPC106395
0.7455	Intermediate Similarity	NPC220217
0.7455	Intermediate Similarity	NPC477125
0.7455	Intermediate Similarity	NPC266570
0.7455	Intermediate Similarity	NPC119855
0.7455	Intermediate Similarity	NPC475290
0.7453	Intermediate Similarity	NPC107243
0.7453	Intermediate Similarity	NPC110937
0.7451	Intermediate Similarity	NPC473647
0.7451	Intermediate Similarity	NPC146554
0.7451	Intermediate Similarity	NPC257485
0.7436	Intermediate Similarity	NPC278681
0.7436	Intermediate Similarity	NPC264954
0.7436	Intermediate Similarity	NPC213761
0.7436	Intermediate Similarity	NPC35171
0.7436	Intermediate Similarity	NPC5292
0.7431	Intermediate Similarity	NPC475623
0.7431	Intermediate Similarity	NPC473694
0.7431	Intermediate Similarity	NPC23584
0.7431	Intermediate Similarity	NPC180204
0.7431	Intermediate Similarity	NPC475334
0.7429	Intermediate Similarity	NPC67584
0.7429	Intermediate Similarity	NPC33473
0.7429	Intermediate Similarity	NPC474909
0.7426	Intermediate Similarity	NPC199382
0.7414	Intermediate Similarity	NPC476959
0.7414	Intermediate Similarity	NPC239273

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 NPC280566 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	1389
0.2-0.3	3865
0.3-0.4	2648
0.4-0.5	671
0.5-0.6	238
0.6-0.7	171
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
0.7368	Intermediate Similarity	NPD6053	Discontinued
0.7311	Intermediate Similarity	NPD7503	Approved
0.7282	Intermediate Similarity	NPD6051	Approved
0.7265	Intermediate Similarity	NPD7115	Discovery
0.7212	Intermediate Similarity	NPD5785	Approved
0.7193	Intermediate Similarity	NPD6371	Approved
0.7168	Intermediate Similarity	NPD6899	Approved
0.7168	Intermediate Similarity	NPD6881	Approved
0.7156	Intermediate Similarity	NPD7640	Approved
0.7156	Intermediate Similarity	NPD7639	Approved
0.7143	Intermediate Similarity	NPD7637	Suspended
0.7143	Intermediate Similarity	NPD5281	Approved
0.7143	Intermediate Similarity	NPD5284	Approved
0.713	Intermediate Similarity	NPD6083	Phase 2
0.713	Intermediate Similarity	NPD8130	Phase 1
0.713	Intermediate Similarity	NPD6084	Phase 2
0.7103	Intermediate Similarity	NPD5695	Phase 3
0.708	Intermediate Similarity	NPD5697	Approved
0.7071	Intermediate Similarity	NPD4820	Approved
0.7071	Intermediate Similarity	NPD4819	Approved
0.7071	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7071	Intermediate Similarity	NPD4822	Approved
0.7071	Intermediate Similarity	NPD4821	Approved
0.7069	Intermediate Similarity	NPD8297	Approved
0.7064	Intermediate Similarity	NPD7638	Approved
0.7048	Intermediate Similarity	NPD7838	Discovery
0.7043	Intermediate Similarity	NPD7290	Approved
0.7043	Intermediate Similarity	NPD7102	Approved
0.7043	Intermediate Similarity	NPD6883	Approved
0.6991	Remote Similarity	NPD7128	Approved
0.6991	Remote Similarity	NPD6675	Approved
0.6991	Remote Similarity	NPD6402	Approved
0.6991	Remote Similarity	NPD5739	Approved
0.6983	Remote Similarity	NPD6617	Approved
0.6983	Remote Similarity	NPD6847	Approved
0.6983	Remote Similarity	NPD6650	Approved
0.6983	Remote Similarity	NPD6869	Approved
0.6983	Remote Similarity	NPD6649	Approved
0.6961	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6013	Approved
0.6957	Remote Similarity	NPD6012	Approved
0.6957	Remote Similarity	NPD6014	Approved
0.6923	Remote Similarity	NPD6882	Approved
0.6916	Remote Similarity	NPD6399	Phase 3
0.6909	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD5696	Approved
0.6909	Remote Similarity	NPD4225	Approved
0.6893	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5211	Phase 2
0.687	Remote Similarity	NPD7320	Approved
0.687	Remote Similarity	NPD6011	Approved
0.6869	Remote Similarity	NPD4271	Approved
0.6869	Remote Similarity	NPD4268	Approved
0.6863	Remote Similarity	NPD6695	Phase 3
0.6863	Remote Similarity	NPD5362	Discontinued
0.6827	Remote Similarity	NPD7334	Approved
0.6827	Remote Similarity	NPD7146	Approved
0.6827	Remote Similarity	NPD6409	Approved
0.6827	Remote Similarity	NPD6684	Approved
0.6827	Remote Similarity	NPD7521	Approved
0.6827	Remote Similarity	NPD5330	Approved
0.6822	Remote Similarity	NPD6050	Approved
0.6822	Remote Similarity	NPD5694	Approved
0.6822	Remote Similarity	NPD5693	Phase 1
0.681	Remote Similarity	NPD6372	Approved
0.681	Remote Similarity	NPD6373	Approved
0.68	Remote Similarity	NPD4195	Approved
0.6783	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD5701	Approved
0.6762	Remote Similarity	NPD7750	Discontinued
0.6754	Remote Similarity	NPD5141	Approved
0.6748	Remote Similarity	NPD8033	Approved
0.6731	Remote Similarity	NPD5363	Approved
0.6729	Remote Similarity	NPD5692	Phase 3
0.6729	Remote Similarity	NPD5207	Approved
0.6699	Remote Similarity	NPD5332	Approved
0.6699	Remote Similarity	NPD5331	Approved
0.6698	Remote Similarity	NPD6903	Approved
0.6698	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5286	Approved
0.6696	Remote Similarity	NPD6648	Approved
0.6696	Remote Similarity	NPD5285	Approved
0.6696	Remote Similarity	NPD4696	Approved
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD8377	Approved
0.6667	Remote Similarity	NPD8294	Approved
0.6639	Remote Similarity	NPD7327	Approved
0.6639	Remote Similarity	NPD7328	Approved
0.6636	Remote Similarity	NPD4753	Phase 2
0.6636	Remote Similarity	NPD6904	Approved
0.6636	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4629	Approved
0.6636	Remote Similarity	NPD5210	Approved
0.6636	Remote Similarity	NPD6080	Approved
0.6636	Remote Similarity	NPD6673	Approved
0.6613	Remote Similarity	NPD8379	Approved
0.6613	Remote Similarity	NPD8378	Approved
0.6613	Remote Similarity	NPD8296	Approved
0.6613	Remote Similarity	NPD8380	Approved
0.6613	Remote Similarity	NPD8335	Approved
0.6606	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD5779	Approved
0.6604	Remote Similarity	NPD7524	Approved
0.6604	Remote Similarity	NPD4251	Approved
0.6604	Remote Similarity	NPD4250	Approved
0.6602	Remote Similarity	NPD5209	Approved
0.6602	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7100	Approved
0.6585	Remote Similarity	NPD7516	Approved
0.6585	Remote Similarity	NPD7101	Approved
0.6579	Remote Similarity	NPD5225	Approved
0.6579	Remote Similarity	NPD4633	Approved
0.6579	Remote Similarity	NPD5226	Approved
0.6579	Remote Similarity	NPD7632	Discontinued
0.6579	Remote Similarity	NPD5224	Approved
0.6571	Remote Similarity	NPD1694	Approved
0.6569	Remote Similarity	NPD7514	Phase 3
0.6569	Remote Similarity	NPD6930	Phase 2
0.6569	Remote Similarity	NPD6931	Approved
0.6555	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD5737	Approved
0.6542	Remote Similarity	NPD6672	Approved
0.6538	Remote Similarity	NPD7154	Phase 3
0.6535	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD5174	Approved
0.6522	Remote Similarity	NPD5175	Approved
0.6518	Remote Similarity	NPD4755	Approved
0.6514	Remote Similarity	NPD6411	Approved
0.6509	Remote Similarity	NPD5280	Approved
0.6509	Remote Similarity	NPD4249	Approved
0.6509	Remote Similarity	NPD5690	Phase 2
0.6509	Remote Similarity	NPD4694	Approved
0.6504	Remote Similarity	NPD6335	Approved
0.6491	Remote Similarity	NPD5223	Approved
0.6491	Remote Similarity	NPD5344	Discontinued
0.6486	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD3133	Approved
0.6476	Remote Similarity	NPD3666	Approved
0.6476	Remote Similarity	NPD3665	Phase 1
0.6475	Remote Similarity	NPD6274	Approved
0.6471	Remote Similarity	NPD6929	Approved
0.6465	Remote Similarity	NPD6924	Approved
0.6465	Remote Similarity	NPD4784	Approved
0.6465	Remote Similarity	NPD6926	Approved
0.6465	Remote Similarity	NPD4785	Approved
0.6455	Remote Similarity	NPD4202	Approved
0.6449	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4632	Approved
0.6442	Remote Similarity	NPD4269	Approved
0.6442	Remote Similarity	NPD4221	Approved
0.6442	Remote Similarity	NPD4270	Approved
0.6442	Remote Similarity	NPD4223	Phase 3
0.6442	Remote Similarity	NPD6435	Approved
0.6441	Remote Similarity	NPD6686	Approved
0.6423	Remote Similarity	NPD6317	Approved
0.6415	Remote Similarity	NPD5329	Approved
0.641	Remote Similarity	NPD6008	Approved
0.6408	Remote Similarity	NPD7332	Phase 2
0.6406	Remote Similarity	NPD7507	Approved
0.6404	Remote Similarity	NPD6404	Discontinued
0.6404	Remote Similarity	NPD4700	Approved
0.64	Remote Similarity	NPD8039	Approved
0.64	Remote Similarity	NPD6319	Approved
0.64	Remote Similarity	NPD8264	Approved
0.6396	Remote Similarity	NPD7748	Approved
0.6389	Remote Similarity	NPD5208	Approved
0.6389	Remote Similarity	NPD4518	Approved
0.6373	Remote Similarity	NPD7145	Approved
0.6373	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7902	Approved
0.6371	Remote Similarity	NPD6313	Approved
0.6371	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD7087	Discontinued
0.6364	Remote Similarity	NPD6079	Approved
0.6356	Remote Similarity	NPD6412	Phase 2
0.6355	Remote Similarity	NPD6098	Approved
0.6355	Remote Similarity	NPD5279	Phase 3
0.6355	Remote Similarity	NPD5786	Approved
0.6346	Remote Similarity	NPD6902	Approved
0.6346	Remote Similarity	NPD5369	Approved
0.6339	Remote Similarity	NPD5654	Approved
0.6337	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6933	Approved
0.633	Remote Similarity	NPD1695	Approved
0.633	Remote Similarity	NPD6101	Approved
0.633	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6328	Remote Similarity	NPD7492	Approved
0.6321	Remote Similarity	NPD4197	Approved
0.6321	Remote Similarity	NPD4786	Approved
0.6308	Remote Similarity	NPD7736	Approved
0.6303	Remote Similarity	NPD4729	Approved
0.6303	Remote Similarity	NPD4730	Approved
0.629	Remote Similarity	NPD6009	Approved
0.6288	Remote Similarity	NPD7260	Phase 2
0.6279	Remote Similarity	NPD6616	Approved
0.6275	Remote Similarity	NPD5776	Phase 2
0.6275	Remote Similarity	NPD6932	Approved
0.6275	Remote Similarity	NPD6925	Approved
0.6273	Remote Similarity	NPD46	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