NPASS Compound

Structure

NPC238850 OpenBabel07101718322D 40 44 0 0 1 0 0 0 0 0999 V2000 -11.3282 -0.8087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9981 -1.0407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8641 2.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2360 2.8410 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2429 1.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2357 1.4579 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8936 1.6859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4622 0.6913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6007 -1.5769 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5962 1.1913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6078 -1.6963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4981 1.5574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4981 1.5574 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3076 1.1852 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0727 -1.0495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8290 -0.9178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4622 -0.3087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4981 -0.1747 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8641 1.1913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2370 2.7961 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1264 -0.7262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4981 -0.1747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7302 0.6913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.3147 1.0658 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0200 0.4834 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1045 -0.9945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7890 0.2151 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5962 -0.8087 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8427 0.5384 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9981 0.6913 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9154 -0.5111 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9981 0.6913 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6987 3.6388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0459 -1.3319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5962 -1.8087 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9529 -0.7824 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8641 0.1913 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7764 1.9085 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7302 -0.3087 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 29 1 0 0 0 0 6 29 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 23 1 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 12 30 1 0 0 0 0 13 32 1 0 0 0 0 14 24 1 0 0 0 0 14 25 1 0 0 0 0 15 21 2 0 0 0 0 15 31 1 0 0 0 0 16 22 1 0 0 0 0 16 31 1 0 0 0 0 17 28 1 0 0 0 0 18 22 1 0 0 0 0 18 32 1 0 0 0 0 19 3 1 6 0 0 0 19 32 1 0 0 0 0 20 33 2 0 0 0 0 20 38 1 0 0 0 0 22 30 1 1 0 0 0 23 19 1 6 0 0 0 23 39 1 0 0 0 0 24 27 1 0 0 0 0 24 38 1 1 0 0 0 25 30 1 6 0 0 0 25 31 1 0 0 0 0 26 34 2 0 0 0 0 26 40 1 0 0 0 0 27 21 1 1 0 0 0 27 29 1 0 0 0 0 28 35 2 0 0 0 0 28 39 1 0 0 0 0 29 40 1 0 0 0 0 30 7 1 6 0 0 0 31 36 1 6 0 0 0 32 37 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	554.29
Volume:	571.112
LogP:	4.022
LogD:	1.976
LogS:	-4.576
# Rotatable Bonds:	4
TPSA:	119.36
# H-Bond Aceptor:	8
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.306
Synthetic Accessibility Score:	5.989
Fsp3:	0.656
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:	-4.941
MDCK Permeability:	1.9355449694558047e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.041
20% Bioavailability (F20%):	0.995
30% Bioavailability (F30%):	0.913

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.944
Plasma Protein Binding (PPB):	77.2083969116211%
Volume Distribution (VD):	2.36
Pgp-substrate:	18.713274002075195%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.216
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.262
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.008
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.367

ADMET: Excretion

Clearance (CL):	2.861
Half-life (T1/2):	0.316

ADMET: Toxicity

hERG Blockers:	0.083
Human Hepatotoxicity (H-HT):	0.588
Drug-inuced Liver Injury (DILI):	0.284
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.686
Maximum Recommended Daily Dose:	0.957
Skin Sensitization:	0.424
Carcinogencity:	0.092
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC238850

Natural Product ID:	NPC238850
*Common Name:**	Longipedlactone M
IUPAC Name:	n.a.
Synonyms:	Longipedlactone M
Standard InCHIKey:	WUMNNWDKNWWLGB-FZIMZWKVSA-N
Standard InCHI:	InChI=1S/C32H42O8/c1-17-8-10-23(39-28(17)35)19(3)32(37)13-12-30(7)22(18(32)2)16-31(36)15-21-9-11-26(34)40-29(5,6)27(21)24(14-25(30)31)38-20(4)33/h8-9,11,15,19,22-25,27,36-37H,2,10,12-14,16H2,1,3-7H3/t19-,22-,23+,24+,25-,27-,30+,31+,32-/m0/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)(O)[C@H]([C@H]1CC=C(C(=O)O1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1077066
PubChem CID:	44626663
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	=	4100.0	nM	PMID[501260]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	10000.0	nM	PMID[501260]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10000.0	nM	PMID[501260]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	>	10000.0	nM	PMID[501260]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	>	10000.0	nM	PMID[501260]

☑ 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 NPC238850 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	195
0.1-0.2	1141
0.2-0.3	4031
0.3-0.4	8650
0.4-0.5	13698
0.5-0.6	8280
0.6-0.7	5576
0.7-0.8	1043
0.8-0.85	69
0.85-0.9	12
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9505	High Similarity	NPC272632
0.9216	High Similarity	NPC280566
0.9151	High Similarity	NPC262083
0.9151	High Similarity	NPC471484
0.9151	High Similarity	NPC255401
0.9151	High Similarity	NPC284162
0.9074	High Similarity	NPC43213
0.9029	High Similarity	NPC183570
0.8962	High Similarity	NPC475274
0.8922	High Similarity	NPC290802
0.8899	High Similarity	NPC216665
0.8879	High Similarity	NPC181298
0.8835	High Similarity	NPC298233
0.8738	High Similarity	NPC227865
0.8716	High Similarity	NPC241477
0.8532	High Similarity	NPC15551
0.8491	Intermediate Similarity	NPC85742
0.8455	Intermediate Similarity	NPC71680
0.8431	Intermediate Similarity	NPC471994
0.8431	Intermediate Similarity	NPC120351
0.8431	Intermediate Similarity	NPC166143
0.8378	Intermediate Similarity	NPC44537
0.8319	Intermediate Similarity	NPC470075
0.8318	Intermediate Similarity	NPC297617
0.8288	Intermediate Similarity	NPC470076
0.8273	Intermediate Similarity	NPC75389
0.8241	Intermediate Similarity	NPC473577
0.8241	Intermediate Similarity	NPC474550
0.8241	Intermediate Similarity	NPC475585
0.8198	Intermediate Similarity	NPC12795
0.819	Intermediate Similarity	NPC114939
0.819	Intermediate Similarity	NPC145074
0.819	Intermediate Similarity	NPC202705
0.819	Intermediate Similarity	NPC41123
0.8182	Intermediate Similarity	NPC275060
0.8182	Intermediate Similarity	NPC137462
0.8182	Intermediate Similarity	NPC304276
0.8165	Intermediate Similarity	NPC475290
0.8148	Intermediate Similarity	NPC473694
0.8148	Intermediate Similarity	NPC475334
0.8148	Intermediate Similarity	NPC475623
0.8142	Intermediate Similarity	NPC171126
0.8073	Intermediate Similarity	NPC475331
0.8073	Intermediate Similarity	NPC475335
0.8073	Intermediate Similarity	NPC181104
0.8073	Intermediate Similarity	NPC121518
0.8073	Intermediate Similarity	NPC80809
0.8073	Intermediate Similarity	NPC288502
0.8073	Intermediate Similarity	NPC201144
0.8073	Intermediate Similarity	NPC103298
0.8056	Intermediate Similarity	NPC471993
0.8053	Intermediate Similarity	NPC247760
0.8036	Intermediate Similarity	NPC103491
0.8036	Intermediate Similarity	NPC16270
0.8034	Intermediate Similarity	NPC185876
0.8034	Intermediate Similarity	NPC19336
0.8019	Intermediate Similarity	NPC99726
0.8019	Intermediate Similarity	NPC141401
0.8018	Intermediate Similarity	NPC470024
0.8017	Intermediate Similarity	NPC16701
0.8017	Intermediate Similarity	NPC288679
0.8	Intermediate Similarity	NPC220217
0.8	Intermediate Similarity	NPC119855
0.8	Intermediate Similarity	NPC60315
0.8	Intermediate Similarity	NPC295843
0.8	Intermediate Similarity	NPC148458
0.7983	Intermediate Similarity	NPC6193
0.7982	Intermediate Similarity	NPC171014
0.7982	Intermediate Similarity	NPC154815
0.7982	Intermediate Similarity	NPC241977
0.7966	Intermediate Similarity	NPC312481
0.7965	Intermediate Similarity	NPC183603
0.7949	Intermediate Similarity	NPC278681
0.7949	Intermediate Similarity	NPC180640
0.7949	Intermediate Similarity	NPC472667
0.7949	Intermediate Similarity	NPC213761
0.7949	Intermediate Similarity	NPC35171
0.7944	Intermediate Similarity	NPC218107
0.7931	Intermediate Similarity	NPC157380
0.7931	Intermediate Similarity	NPC185287
0.7928	Intermediate Similarity	NPC43063
0.7928	Intermediate Similarity	NPC109376
0.7928	Intermediate Similarity	NPC79298
0.7909	Intermediate Similarity	NPC473543
0.789	Intermediate Similarity	NPC155332
0.789	Intermediate Similarity	NPC32577
0.789	Intermediate Similarity	NPC114540
0.789	Intermediate Similarity	NPC109195
0.789	Intermediate Similarity	NPC475038
0.7881	Intermediate Similarity	NPC257610
0.7881	Intermediate Similarity	NPC112936
0.7863	Intermediate Similarity	NPC472760
0.7863	Intermediate Similarity	NPC475372
0.7857	Intermediate Similarity	NPC224660
0.7838	Intermediate Similarity	NPC172867
0.7838	Intermediate Similarity	NPC218158
0.783	Intermediate Similarity	NPC276110
0.7818	Intermediate Similarity	NPC473523
0.7818	Intermediate Similarity	NPC329345
0.7818	Intermediate Similarity	NPC189588
0.7818	Intermediate Similarity	NPC160583
0.7818	Intermediate Similarity	NPC187302
0.7818	Intermediate Similarity	NPC23584
0.7818	Intermediate Similarity	NPC10232
0.7818	Intermediate Similarity	NPC196471
0.7818	Intermediate Similarity	NPC72151
0.7818	Intermediate Similarity	NPC473283
0.7818	Intermediate Similarity	NPC97487
0.7818	Intermediate Similarity	NPC475526
0.7815	Intermediate Similarity	NPC233500
0.781	Intermediate Similarity	NPC152778
0.781	Intermediate Similarity	NPC205034
0.781	Intermediate Similarity	NPC38232
0.781	Intermediate Similarity	NPC162615
0.7807	Intermediate Similarity	NPC17791
0.7807	Intermediate Similarity	NPC474315
0.7798	Intermediate Similarity	NPC115899
0.7798	Intermediate Similarity	NPC222875
0.7798	Intermediate Similarity	NPC295110
0.7798	Intermediate Similarity	NPC268829
0.7798	Intermediate Similarity	NPC99411
0.7798	Intermediate Similarity	NPC25177
0.7798	Intermediate Similarity	NPC146822
0.7798	Intermediate Similarity	NPC247701
0.7797	Intermediate Similarity	NPC305260
0.7797	Intermediate Similarity	NPC5292
0.7797	Intermediate Similarity	NPC312536
0.7797	Intermediate Similarity	NPC219656
0.7797	Intermediate Similarity	NPC270850
0.7788	Intermediate Similarity	NPC182136
0.7778	Intermediate Similarity	NPC153651
0.7778	Intermediate Similarity	NPC476959
0.7778	Intermediate Similarity	NPC278673
0.7778	Intermediate Similarity	NPC239273
0.7769	Intermediate Similarity	NPC145238
0.7768	Intermediate Similarity	NPC475781
0.7768	Intermediate Similarity	NPC469957
0.7768	Intermediate Similarity	NPC472263
0.7768	Intermediate Similarity	NPC108682
0.7768	Intermediate Similarity	NPC469959
0.7767	Intermediate Similarity	NPC473879
0.7759	Intermediate Similarity	NPC82759
0.7757	Intermediate Similarity	NPC190713
0.7757	Intermediate Similarity	NPC16967
0.775	Intermediate Similarity	NPC196130
0.7739	Intermediate Similarity	NPC475524
0.7739	Intermediate Similarity	NPC100267
0.7739	Intermediate Similarity	NPC470025
0.7739	Intermediate Similarity	NPC328074
0.7739	Intermediate Similarity	NPC321272
0.7739	Intermediate Similarity	NPC317460
0.7736	Intermediate Similarity	NPC119562
0.7736	Intermediate Similarity	NPC279410
0.7736	Intermediate Similarity	NPC469491
0.7731	Intermediate Similarity	NPC143755
0.7731	Intermediate Similarity	NPC329080
0.7731	Intermediate Similarity	NPC472759
0.7727	Intermediate Similarity	NPC470972
0.7727	Intermediate Similarity	NPC475344
0.7727	Intermediate Similarity	NPC475320
0.7727	Intermediate Similarity	NPC320447
0.7727	Intermediate Similarity	NPC11956
0.7727	Intermediate Similarity	NPC472552
0.7727	Intermediate Similarity	NPC476471
0.7719	Intermediate Similarity	NPC316708
0.7719	Intermediate Similarity	NPC6206
0.7714	Intermediate Similarity	NPC177641
0.7712	Intermediate Similarity	NPC153440
0.7712	Intermediate Similarity	NPC146786
0.7706	Intermediate Similarity	NPC251680
0.7706	Intermediate Similarity	NPC38855
0.7706	Intermediate Similarity	NPC266955
0.7706	Intermediate Similarity	NPC241221
0.7699	Intermediate Similarity	NPC220155
0.7699	Intermediate Similarity	NPC88701
0.7699	Intermediate Similarity	NPC473482
0.7699	Intermediate Similarity	NPC318363
0.7699	Intermediate Similarity	NPC475418
0.7699	Intermediate Similarity	NPC472825
0.7692	Intermediate Similarity	NPC470793
0.7692	Intermediate Similarity	NPC190286
0.7686	Intermediate Similarity	NPC219804
0.7686	Intermediate Similarity	NPC55602
0.7685	Intermediate Similarity	NPC311241
0.7685	Intermediate Similarity	NPC475446
0.7685	Intermediate Similarity	NPC110937
0.7679	Intermediate Similarity	NPC469960
0.7679	Intermediate Similarity	NPC266570
0.7679	Intermediate Similarity	NPC93026
0.7679	Intermediate Similarity	NPC470980
0.7679	Intermediate Similarity	NPC265502
0.7679	Intermediate Similarity	NPC472818
0.7679	Intermediate Similarity	NPC29389
0.7672	Intermediate Similarity	NPC474937
0.7672	Intermediate Similarity	NPC470027
0.7667	Intermediate Similarity	NPC46570
0.7664	Intermediate Similarity	NPC281134
0.7661	Intermediate Similarity	NPC221414
0.7661	Intermediate Similarity	NPC134902
0.7658	Intermediate Similarity	NPC474124

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 NPC238850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	164
0.1-0.2	1290
0.2-0.3	3750
0.3-0.4	2661
0.4-0.5	811
0.5-0.6	222
0.6-0.7	229
0.7-0.8	23
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
0.7706	Intermediate Similarity	NPD7640	Approved
0.7706	Intermediate Similarity	NPD7639	Approved
0.7667	Intermediate Similarity	NPD7503	Approved
0.7615	Intermediate Similarity	NPD7638	Approved
0.7383	Intermediate Similarity	NPD7637	Suspended
0.7377	Intermediate Similarity	NPD8033	Approved
0.7333	Intermediate Similarity	NPD7115	Discovery
0.7295	Intermediate Similarity	NPD8294	Approved
0.7295	Intermediate Similarity	NPD8377	Approved
0.7288	Intermediate Similarity	NPD6053	Discontinued
0.7288	Intermediate Similarity	NPD8297	Approved
0.7273	Intermediate Similarity	NPD7328	Approved
0.7273	Intermediate Similarity	NPD7327	Approved
0.7241	Intermediate Similarity	NPD6899	Approved
0.7241	Intermediate Similarity	NPD6881	Approved
0.7236	Intermediate Similarity	NPD8380	Approved
0.7236	Intermediate Similarity	NPD8335	Approved
0.7236	Intermediate Similarity	NPD8379	Approved
0.7236	Intermediate Similarity	NPD8378	Approved
0.7236	Intermediate Similarity	NPD8296	Approved
0.7232	Intermediate Similarity	NPD6648	Approved
0.7213	Intermediate Similarity	NPD7516	Approved
0.7212	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD8130	Phase 1
0.7203	Intermediate Similarity	NPD6649	Approved
0.7203	Intermediate Similarity	NPD6650	Approved
0.7155	Intermediate Similarity	NPD5697	Approved
0.7143	Intermediate Similarity	NPD4225	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.713	Intermediate Similarity	NPD7838	Discovery
0.7119	Intermediate Similarity	NPD6371	Approved
0.7119	Intermediate Similarity	NPD7290	Approved
0.7119	Intermediate Similarity	NPD6883	Approved
0.7119	Intermediate Similarity	NPD7102	Approved
0.7115	Intermediate Similarity	NPD6695	Phase 3
0.7105	Intermediate Similarity	NPD7632	Discontinued
0.7069	Intermediate Similarity	NPD7128	Approved
0.7069	Intermediate Similarity	NPD5739	Approved
0.7069	Intermediate Similarity	NPD6675	Approved
0.7069	Intermediate Similarity	NPD6402	Approved
0.7059	Intermediate Similarity	NPD6869	Approved
0.7059	Intermediate Similarity	NPD6617	Approved
0.7059	Intermediate Similarity	NPD6847	Approved
0.7037	Intermediate Similarity	NPD6051	Approved
0.7034	Intermediate Similarity	NPD6372	Approved
0.7034	Intermediate Similarity	NPD6013	Approved
0.7034	Intermediate Similarity	NPD6014	Approved
0.7034	Intermediate Similarity	NPD6373	Approved
0.7034	Intermediate Similarity	NPD6012	Approved
0.7018	Intermediate Similarity	NPD5344	Discontinued
0.7009	Intermediate Similarity	NPD7750	Discontinued
0.7008	Intermediate Similarity	NPD7507	Approved
0.6991	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5211	Phase 2
0.6949	Remote Similarity	NPD7320	Approved
0.6949	Remote Similarity	NPD6011	Approved
0.6909	Remote Similarity	NPD5284	Approved
0.6909	Remote Similarity	NPD5281	Approved
0.6903	Remote Similarity	NPD6083	Phase 2
0.6903	Remote Similarity	NPD6084	Phase 2
0.688	Remote Similarity	NPD6319	Approved
0.6875	Remote Similarity	NPD5695	Phase 3
0.6864	Remote Similarity	NPD5701	Approved
0.6864	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7524	Approved
0.6847	Remote Similarity	NPD6399	Phase 3
0.6846	Remote Similarity	NPD7319	Approved
0.6838	Remote Similarity	NPD5141	Approved
0.6827	Remote Similarity	NPD6931	Approved
0.6827	Remote Similarity	NPD6930	Phase 2
0.6827	Remote Similarity	NPD7514	Phase 3
0.6818	Remote Similarity	NPD5785	Approved
0.6807	Remote Similarity	NPD6686	Approved
0.6803	Remote Similarity	NPD4632	Approved
0.6783	Remote Similarity	NPD4696	Approved
0.6783	Remote Similarity	NPD5285	Approved
0.6783	Remote Similarity	NPD5286	Approved
0.678	Remote Similarity	NPD6008	Approved
0.6731	Remote Similarity	NPD6929	Approved
0.6697	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5696	Approved
0.6696	Remote Similarity	NPD5779	Approved
0.6696	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD4821	Approved
0.6667	Remote Similarity	NPD7100	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD7101	Approved
0.6667	Remote Similarity	NPD4822	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD7332	Phase 2
0.6667	Remote Similarity	NPD4819	Approved
0.6667	Remote Similarity	NPD4820	Approved
0.6667	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD7736	Approved
0.664	Remote Similarity	NPD6009	Approved
0.6639	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD7145	Approved
0.6615	Remote Similarity	NPD6616	Approved
0.6614	Remote Similarity	NPD6054	Approved
0.661	Remote Similarity	NPD5175	Approved
0.661	Remote Similarity	NPD5174	Approved
0.6609	Remote Similarity	NPD4755	Approved
0.6607	Remote Similarity	NPD5694	Approved
0.6607	Remote Similarity	NPD6050	Approved
0.6607	Remote Similarity	NPD7087	Discontinued
0.6607	Remote Similarity	NPD5693	Phase 1
0.6606	Remote Similarity	NPD7334	Approved
0.6606	Remote Similarity	NPD6684	Approved
0.6606	Remote Similarity	NPD6409	Approved
0.6606	Remote Similarity	NPD5330	Approved
0.6606	Remote Similarity	NPD7521	Approved
0.6606	Remote Similarity	NPD7146	Approved
0.6604	Remote Similarity	NPD6902	Approved
0.6589	Remote Similarity	NPD7604	Phase 2
0.6587	Remote Similarity	NPD6335	Approved
0.6581	Remote Similarity	NPD5223	Approved
0.6574	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4195	Approved
0.6565	Remote Similarity	NPD7078	Approved
0.6562	Remote Similarity	NPD5983	Phase 2
0.656	Remote Similarity	NPD6274	Approved
0.6557	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD4634	Approved
0.6549	Remote Similarity	NPD4202	Approved
0.6545	Remote Similarity	NPD4251	Approved
0.6545	Remote Similarity	NPD4250	Approved
0.6542	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5776	Phase 2
0.6538	Remote Similarity	NPD6925	Approved
0.6538	Remote Similarity	NPD6932	Approved
0.6532	Remote Similarity	NPD8133	Approved
0.6529	Remote Similarity	NPD4730	Approved
0.6529	Remote Similarity	NPD4729	Approved
0.6518	Remote Similarity	NPD5207	Approved
0.6518	Remote Similarity	NPD5692	Phase 3
0.6514	Remote Similarity	NPD6893	Approved
0.6514	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD6370	Approved
0.6509	Remote Similarity	NPD7525	Registered
0.6508	Remote Similarity	NPD6317	Approved
0.6496	Remote Similarity	NPD4700	Approved
0.6491	Remote Similarity	NPD7748	Approved
0.6489	Remote Similarity	NPD6336	Discontinued
0.6486	Remote Similarity	NPD6903	Approved
0.6486	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD5362	Discontinued
0.6476	Remote Similarity	NPD4271	Approved
0.6476	Remote Similarity	NPD4268	Approved
0.6475	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD7902	Approved
0.646	Remote Similarity	NPD8035	Phase 2
0.646	Remote Similarity	NPD6079	Approved
0.646	Remote Similarity	NPD8034	Phase 2
0.6457	Remote Similarity	NPD6314	Approved
0.6457	Remote Similarity	NPD6313	Approved
0.6455	Remote Similarity	NPD4249	Approved
0.6446	Remote Similarity	NPD6412	Phase 2
0.6439	Remote Similarity	NPD8293	Discontinued
0.6435	Remote Similarity	NPD5210	Approved
0.6435	Remote Similarity	NPD4629	Approved
0.6435	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD6015	Approved
0.6434	Remote Similarity	NPD8513	Phase 3
0.6434	Remote Similarity	NPD6016	Approved
0.6429	Remote Similarity	NPD4753	Phase 2
0.6429	Remote Similarity	NPD6904	Approved
0.6429	Remote Similarity	NPD6673	Approved
0.6429	Remote Similarity	NPD6080	Approved
0.6423	Remote Similarity	NPD5250	Approved
0.6423	Remote Similarity	NPD5249	Phase 3
0.6423	Remote Similarity	NPD5251	Approved
0.6423	Remote Similarity	NPD5247	Approved
0.6423	Remote Similarity	NPD5248	Approved
0.6408	Remote Similarity	NPD6926	Approved
0.6408	Remote Similarity	NPD6924	Approved
0.6385	Remote Similarity	NPD5988	Approved
0.6372	Remote Similarity	NPD6698	Approved
0.6372	Remote Similarity	NPD46	Approved
0.637	Remote Similarity	NPD7260	Phase 2
0.6364	Remote Similarity	NPD5363	Approved
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6364	Remote Similarity	NPD1694	Approved
0.6357	Remote Similarity	NPD6059	Approved
0.6346	Remote Similarity	NPD8264	Approved
0.6339	Remote Similarity	NPD6672	Approved
0.6339	Remote Similarity	NPD5737	Approved
0.633	Remote Similarity	NPD5332	Approved
0.633	Remote Similarity	NPD5331	Approved
0.6321	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7983	Approved
0.6316	Remote Similarity	NPD6411	Approved
0.6311	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6909	Approved
0.6308	Remote Similarity	NPD8516	Approved
0.6308	Remote Similarity	NPD6908	Approved
0.6308	Remote Similarity	NPD8517	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