NPASS Compound

Structure

NPC475949 OpenBabel07101718232D 30 32 0 0 1 0 0 0 0 0999 V2000 -1.0592 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3970 0.3580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4605 5.2541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0592 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0592 2.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 3.4271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6470 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.4660 5.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6470 3.4271 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1369 2.6180 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1369 1.6180 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 0.8090 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.6758 2.1180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8782 5.9586 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6758 2.1180 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0592 4.2361 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0880 2.9271 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 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 10 1 0 0 0 0 2 11 1 0 0 0 0 3 12 2 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 7 8 1 0 0 0 0 7 10 2 0 0 0 0 8 15 1 0 0 0 0 9 11 2 0 0 0 0 10 19 1 0 0 0 0 11 15 1 0 0 0 0 12 20 1 0 0 0 0 13 22 1 6 0 0 0 13 30 1 0 0 0 0 14 23 2 0 0 0 0 14 27 1 0 0 0 0 15 27 1 1 0 0 0 16 9 1 6 0 0 0 16 17 1 0 0 0 0 16 28 1 0 0 0 0 17 12 1 1 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 24 1 0 0 0 0 19 29 1 0 0 0 0 20 25 2 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 26 2 0 0 0 0 21 29 1 0 0 0 0 22 6 1 1 0 0 0 22 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	420.18
Volume:	417.902
LogP:	1.488
LogD:	1.389
LogS:	-3.24
# Rotatable Bonds:	5
TPSA:	111.66
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	5.336
Fsp3:	0.591
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.119
MDCK Permeability:	9.058813157025725e-05
Pgp-inhibitor:	0.8
Pgp-substrate:	0.01
Human Intestinal Absorption (HIA):	0.953
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055
Plasma Protein Binding (PPB):	83.8986587524414%
Volume Distribution (VD):	1.219
Pgp-substrate:	10.30831241607666%

ADMET: Metabolism

CYP1A2-inhibitor:	0.022
CYP1A2-substrate:	0.107
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.669
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.162
CYP3A4-inhibitor:	0.455
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	4.989
Half-life (T1/2):	0.569

ADMET: Toxicity

hERG Blockers:	0.013
Human Hepatotoxicity (H-HT):	0.733
Drug-inuced Liver Injury (DILI):	0.893
AMES Toxicity:	0.62
Rat Oral Acute Toxicity:	0.732
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.338
Carcinogencity:	0.066
Eye Corrosion:	0.004
Eye Irritation:	0.012
Respiratory Toxicity:	0.881

Download Data

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

Natural Product: NPC475949

Natural Product ID:	NPC475949
*Common Name:**	Eupatocunoxin
IUPAC Name:	n.a.
Synonyms:	Eupatocunoxin
Standard InCHIKey:	UZTYOOVAPGOQDZ-OJVYPSFZSA-N
Standard InCHI:	InChI=1S/C22H28O8/c1-10-7-8-15(27-14(5)23)11(2)9-16-17(12(3)20(25)28-16)18(24)19(10)29-21(26)22(6)13(4)30-22/h7,9,13,15-19,24H,3,8H2,1-2,4-6H3/b10-7-,11-9+/t13-,15+,16-,17+,18?,19?,22-/m1/s1
SMILES:	CC(=O)O[C@H]1C/C=C(/C)C(OC(=O)[C@]2(C)O[C@@H]2C)C([C@@H]2[C@@H](/C=C/1C)OC(=O)C2=C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519356
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001771] Germacranolides and derivatives

*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
NPO33469	Asteraceae	Family	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18329753]

☑ 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
ED50	2
Others	1

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	pED50	=	5.39	n.a.	PMID[510069]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	1.7	ug ml-1	PMID[510069]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.04	umol/L	PMID[510070]

☑ 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 NPC475949 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	238
0.1-0.2	1620
0.2-0.3	5569
0.3-0.4	10630
0.4-0.5	13829
0.5-0.6	6894
0.6-0.7	2869
0.7-0.8	820
0.8-0.85	150
0.85-0.9	64
0.9-0.95	12
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9468	High Similarity	NPC471144
0.9388	High Similarity	NPC477513
0.9255	High Similarity	NPC473859
0.9255	High Similarity	NPC17585
0.9175	High Similarity	NPC471148
0.9149	High Similarity	NPC475659
0.9072	High Similarity	NPC474339
0.9072	High Similarity	NPC164598
0.898	High Similarity	NPC149371
0.8969	High Similarity	NPC288876
0.8969	High Similarity	NPC477512
0.8947	High Similarity	NPC471142
0.8925	High Similarity	NPC473619
0.8878	High Similarity	NPC264477
0.8878	High Similarity	NPC201718
0.8878	High Similarity	NPC47880
0.8878	High Similarity	NPC477511
0.8854	High Similarity	NPC477921
0.8842	High Similarity	NPC57405
0.8842	High Similarity	NPC303942
0.883	High Similarity	NPC473321
0.8804	High Similarity	NPC266957
0.8763	High Similarity	NPC471140
0.875	High Similarity	NPC14961
0.875	High Similarity	NPC270013
0.875	High Similarity	NPC477922
0.8737	High Similarity	NPC212486
0.8723	High Similarity	NPC474232
0.871	High Similarity	NPC473715
0.871	High Similarity	NPC287089
0.8687	High Similarity	NPC476270
0.8673	High Similarity	NPC473326
0.866	High Similarity	NPC230800
0.866	High Similarity	NPC476315
0.866	High Similarity	NPC279621
0.8646	High Similarity	NPC81386
0.8646	High Similarity	NPC471147
0.8646	High Similarity	NPC474035
0.8627	High Similarity	NPC324327
0.8627	High Similarity	NPC326994
0.8627	High Similarity	NPC474421
0.8627	High Similarity	NPC194620
0.8627	High Similarity	NPC72813
0.8614	High Similarity	NPC471143
0.8614	High Similarity	NPC477510
0.8614	High Similarity	NPC474741
0.8557	High Similarity	NPC36954
0.8544	High Similarity	NPC474664
0.8544	High Similarity	NPC55972
0.8544	High Similarity	NPC233379
0.8544	High Similarity	NPC14862
0.8544	High Similarity	NPC327286
0.8544	High Similarity	NPC169888
0.8542	High Similarity	NPC288240
0.8542	High Similarity	NPC476300
0.8542	High Similarity	NPC475912
0.8542	High Similarity	NPC165383
0.8542	High Similarity	NPC295204
0.8542	High Similarity	NPC273579
0.8542	High Similarity	NPC162205
0.8529	High Similarity	NPC16313
0.8529	High Similarity	NPC9303
0.8515	High Similarity	NPC475945
0.8515	High Similarity	NPC475871
0.8515	High Similarity	NPC472755
0.8495	Intermediate Similarity	NPC469910
0.8469	Intermediate Similarity	NPC39859
0.8469	Intermediate Similarity	NPC158416
0.8469	Intermediate Similarity	NPC76862
0.8469	Intermediate Similarity	NPC470883
0.8462	Intermediate Similarity	NPC15218
0.8462	Intermediate Similarity	NPC475922
0.8454	Intermediate Similarity	NPC190294
0.8454	Intermediate Similarity	NPC474247
0.8438	Intermediate Similarity	NPC30515
0.8438	Intermediate Similarity	NPC184463
0.8438	Intermediate Similarity	NPC20713
0.8421	Intermediate Similarity	NPC474032
0.8421	Intermediate Similarity	NPC151770
0.8416	Intermediate Similarity	NPC474747
0.8416	Intermediate Similarity	NPC320019
0.8416	Intermediate Similarity	NPC324017
0.8416	Intermediate Similarity	NPC472754
0.8387	Intermediate Similarity	NPC21469
0.8381	Intermediate Similarity	NPC115257
0.8381	Intermediate Similarity	NPC161816
0.8367	Intermediate Similarity	NPC471141
0.8351	Intermediate Similarity	NPC475838
0.8351	Intermediate Similarity	NPC125674
0.8351	Intermediate Similarity	NPC179746
0.8351	Intermediate Similarity	NPC81419
0.8351	Intermediate Similarity	NPC228451
0.835	Intermediate Similarity	NPC475802
0.8333	Intermediate Similarity	NPC475748
0.8333	Intermediate Similarity	NPC51004
0.8333	Intermediate Similarity	NPC4620
0.8317	Intermediate Similarity	NPC474742
0.8317	Intermediate Similarity	NPC46998
0.8317	Intermediate Similarity	NPC133907
0.8317	Intermediate Similarity	NPC15993
0.8317	Intermediate Similarity	NPC185141
0.8317	Intermediate Similarity	NPC110443
0.8317	Intermediate Similarity	NPC128733
0.8317	Intermediate Similarity	NPC472753
0.8316	Intermediate Similarity	NPC202672
0.8316	Intermediate Similarity	NPC476803
0.8316	Intermediate Similarity	NPC475819
0.83	Intermediate Similarity	NPC474213
0.8286	Intermediate Similarity	NPC38154
0.8283	Intermediate Similarity	NPC476009
0.8283	Intermediate Similarity	NPC306041
0.828	Intermediate Similarity	NPC158756
0.8265	Intermediate Similarity	NPC473316
0.8265	Intermediate Similarity	NPC473330
0.8265	Intermediate Similarity	NPC140543
0.8252	Intermediate Similarity	NPC472756
0.8252	Intermediate Similarity	NPC475676
0.8252	Intermediate Similarity	NPC220964
0.8247	Intermediate Similarity	NPC12172
0.8247	Intermediate Similarity	NPC208886
0.8229	Intermediate Similarity	NPC307411
0.8229	Intermediate Similarity	NPC166919
0.8224	Intermediate Similarity	NPC473877
0.8211	Intermediate Similarity	NPC231889
0.82	Intermediate Similarity	NPC328562
0.82	Intermediate Similarity	NPC323421
0.8191	Intermediate Similarity	NPC319795
0.8191	Intermediate Similarity	NPC50362
0.8191	Intermediate Similarity	NPC38468
0.8191	Intermediate Similarity	NPC470755
0.8163	Intermediate Similarity	NPC475302
0.8144	Intermediate Similarity	NPC65359
0.8144	Intermediate Similarity	NPC475855
0.8144	Intermediate Similarity	NPC476004
0.8144	Intermediate Similarity	NPC474761
0.8137	Intermediate Similarity	NPC473332
0.8125	Intermediate Similarity	NPC476805
0.8119	Intermediate Similarity	NPC161855
0.8119	Intermediate Similarity	NPC208233
0.8105	Intermediate Similarity	NPC50637
0.81	Intermediate Similarity	NPC35498
0.81	Intermediate Similarity	NPC31645
0.8091	Intermediate Similarity	NPC471146
0.8081	Intermediate Similarity	NPC476267
0.8081	Intermediate Similarity	NPC121825
0.8077	Intermediate Similarity	NPC100487
0.8061	Intermediate Similarity	NPC70251
0.8061	Intermediate Similarity	NPC475881
0.802	Intermediate Similarity	NPC40812
0.8018	Intermediate Similarity	NPC475401
0.8	Intermediate Similarity	NPC223450
0.8	Intermediate Similarity	NPC243998
0.8	Intermediate Similarity	NPC474947
0.8	Intermediate Similarity	NPC475900
0.8	Intermediate Similarity	NPC474333
0.7981	Intermediate Similarity	NPC474165
0.7981	Intermediate Similarity	NPC19239
0.7981	Intermediate Similarity	NPC474166
0.7981	Intermediate Similarity	NPC69171
0.7981	Intermediate Similarity	NPC475873
0.798	Intermediate Similarity	NPC469645
0.798	Intermediate Similarity	NPC469692
0.7979	Intermediate Similarity	NPC473390
0.7979	Intermediate Similarity	NPC169575
0.7979	Intermediate Similarity	NPC131669
0.7979	Intermediate Similarity	NPC40746
0.7979	Intermediate Similarity	NPC116543
0.7959	Intermediate Similarity	NPC179394
0.7959	Intermediate Similarity	NPC316228
0.7959	Intermediate Similarity	NPC251385
0.7959	Intermediate Similarity	NPC469718
0.7959	Intermediate Similarity	NPC49342
0.7959	Intermediate Similarity	NPC144133
0.7959	Intermediate Similarity	NPC329857
0.7957	Intermediate Similarity	NPC24417
0.7946	Intermediate Similarity	NPC477092
0.7944	Intermediate Similarity	NPC42662
0.7941	Intermediate Similarity	NPC279561
0.7938	Intermediate Similarity	NPC475902
0.7938	Intermediate Similarity	NPC281516
0.7935	Intermediate Similarity	NPC167881
0.7935	Intermediate Similarity	NPC98557
0.7928	Intermediate Similarity	NPC475305
0.7928	Intermediate Similarity	NPC476713
0.7928	Intermediate Similarity	NPC296822
0.7928	Intermediate Similarity	NPC476712
0.7925	Intermediate Similarity	NPC26617
0.7921	Intermediate Similarity	NPC473291
0.7921	Intermediate Similarity	NPC476275
0.7905	Intermediate Similarity	NPC203659
0.7905	Intermediate Similarity	NPC472748
0.7895	Intermediate Similarity	NPC476804
0.789	Intermediate Similarity	NPC66108
0.7885	Intermediate Similarity	NPC183571
0.7879	Intermediate Similarity	NPC158061
0.7879	Intermediate Similarity	NPC469627
0.7872	Intermediate Similarity	NPC229825
0.7857	Intermediate Similarity	NPC173926
0.7857	Intermediate Similarity	NPC475971
0.7857	Intermediate Similarity	NPC92974

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 NPC475949 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	2247
0.2-0.3	3791
0.3-0.4	1916
0.4-0.5	667
0.5-0.6	256
0.6-0.7	50
0.7-0.8	6
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8191	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD46	Approved
0.7959	Intermediate Similarity	NPD6698	Approved
0.7925	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD7983	Approved
0.7426	Intermediate Similarity	NPD7838	Discovery
0.7387	Intermediate Similarity	NPD6371	Approved
0.7168	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1695	Approved
0.6917	Remote Similarity	NPD8515	Approved
0.6917	Remote Similarity	NPD8517	Approved
0.6917	Remote Similarity	NPD8516	Approved
0.6917	Remote Similarity	NPD8513	Phase 3
0.6803	Remote Similarity	NPD7642	Approved
0.6789	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD4225	Approved
0.6754	Remote Similarity	NPD6686	Approved
0.6729	Remote Similarity	NPD5282	Discontinued
0.6694	Remote Similarity	NPD6319	Approved
0.6692	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD7829	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.664	Remote Similarity	NPD8074	Phase 3
0.6636	Remote Similarity	NPD5779	Approved
0.6636	Remote Similarity	NPD5778	Approved
0.6606	Remote Similarity	NPD7839	Suspended
0.6604	Remote Similarity	NPD5785	Approved
0.6583	Remote Similarity	NPD7115	Discovery
0.6581	Remote Similarity	NPD2204	Approved
0.6569	Remote Similarity	NPD6110	Phase 1
0.6538	Remote Similarity	NPD4249	Approved
0.6538	Remote Similarity	NPD5786	Approved
0.6476	Remote Similarity	NPD4250	Approved
0.6476	Remote Similarity	NPD4251	Approved
0.6466	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD5363	Approved
0.641	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD7154	Phase 3
0.6387	Remote Similarity	NPD6053	Discontinued
0.6373	Remote Similarity	NPD5369	Approved
0.6356	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD7492	Approved
0.6311	Remote Similarity	NPD6435	Approved
0.6311	Remote Similarity	NPD4269	Approved
0.6311	Remote Similarity	NPD4270	Approved
0.6299	Remote Similarity	NPD8451	Approved
0.6299	Remote Similarity	NPD8273	Phase 1
0.6299	Remote Similarity	NPD6616	Approved
0.629	Remote Similarity	NPD6054	Approved
0.6283	Remote Similarity	NPD6648	Approved
0.6279	Remote Similarity	NPD7319	Approved
0.6275	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6275	Remote Similarity	NPD4252	Approved
0.627	Remote Similarity	NPD8328	Phase 3
0.625	Remote Similarity	NPD7078	Approved
0.625	Remote Similarity	NPD8448	Approved
0.625	Remote Similarity	NPD8297	Approved
0.624	Remote Similarity	NPD6016	Approved
0.624	Remote Similarity	NPD8444	Approved
0.624	Remote Similarity	NPD6015	Approved
0.6204	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6101	Approved
0.6202	Remote Similarity	NPD7736	Approved
0.6198	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD8080	Discontinued
0.619	Remote Similarity	NPD5988	Approved
0.619	Remote Similarity	NPD6370	Approved
0.6179	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6172	Remote Similarity	NPD7507	Approved
0.6167	Remote Similarity	NPD6650	Approved
0.6167	Remote Similarity	NPD6649	Approved
0.616	Remote Similarity	NPD6059	Approved
0.6154	Remote Similarity	NPD5209	Approved
0.6134	Remote Similarity	NPD6372	Approved
0.6134	Remote Similarity	NPD6373	Approved
0.6132	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD7641	Discontinued
0.6124	Remote Similarity	NPD8293	Discontinued
0.6117	Remote Similarity	NPD4819	Approved
0.6117	Remote Similarity	NPD4822	Approved
0.6117	Remote Similarity	NPD4820	Approved
0.6117	Remote Similarity	NPD4821	Approved
0.6117	Remote Similarity	NPD5368	Approved
0.6111	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6107	Remote Similarity	NPD8391	Approved
0.6107	Remote Similarity	NPD8392	Approved
0.6107	Remote Similarity	NPD8390	Approved
0.6102	Remote Similarity	NPD5697	Approved
0.6102	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD5362	Discontinued
0.6094	Remote Similarity	NPD8342	Approved
0.6094	Remote Similarity	NPD8340	Approved
0.6094	Remote Similarity	NPD8341	Approved
0.6094	Remote Similarity	NPD8299	Approved
0.6091	Remote Similarity	NPD6411	Approved
0.6078	Remote Similarity	NPD4271	Approved
0.6078	Remote Similarity	NPD4268	Approved
0.6061	Remote Similarity	NPD7260	Phase 2
0.605	Remote Similarity	NPD6899	Approved
0.605	Remote Similarity	NPD6881	Approved
0.6048	Remote Similarity	NPD6009	Approved
0.6017	Remote Similarity	NPD6008	Approved
0.6017	Remote Similarity	NPD7128	Approved
0.6017	Remote Similarity	NPD6675	Approved
0.6017	Remote Similarity	NPD5739	Approved
0.6017	Remote Similarity	NPD6402	Approved
0.6016	Remote Similarity	NPD7604	Phase 2
0.6	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6014	Approved
0.6	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6013	Approved
0.6	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6012	Approved
0.5984	Remote Similarity	NPD6882	Approved
0.5984	Remote Similarity	NPD5983	Phase 2
0.5984	Remote Similarity	NPD6921	Approved
0.598	Remote Similarity	NPD4756	Discovery
0.5966	Remote Similarity	NPD5701	Approved
0.595	Remote Similarity	NPD6883	Approved
0.595	Remote Similarity	NPD7102	Approved
0.595	Remote Similarity	NPD6421	Discontinued
0.595	Remote Similarity	NPD7290	Approved
0.595	Remote Similarity	NPD4634	Approved
0.5946	Remote Similarity	NPD7637	Suspended
0.5926	Remote Similarity	NPD8415	Approved
0.592	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.5917	Remote Similarity	NPD7320	Approved
0.5917	Remote Similarity	NPD6011	Approved
0.5913	Remote Similarity	NPD7638	Approved
0.5909	Remote Similarity	NPD5370	Suspended
0.5902	Remote Similarity	NPD6617	Approved
0.5902	Remote Similarity	NPD6847	Approved
0.5902	Remote Similarity	NPD8130	Phase 1
0.5902	Remote Similarity	NPD6869	Approved
0.5896	Remote Similarity	NPD6845	Suspended
0.5895	Remote Similarity	NPD3197	Phase 1
0.5877	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5876	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD7640	Approved
0.5862	Remote Similarity	NPD7639	Approved
0.5849	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD1694	Approved
0.5826	Remote Similarity	NPD6084	Phase 2
0.5826	Remote Similarity	NPD6083	Phase 2
0.5804	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5802	Remote Similarity	NPD6336	Discontinued
0.5798	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5794	Remote Similarity	NPD7500	Approved
0.5789	Remote Similarity	NPD5695	Phase 3
0.5776	Remote Similarity	NPD5696	Approved
0.5769	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5736	Remote Similarity	NPD8269	Approved
0.5736	Remote Similarity	NPD8268	Approved
0.5736	Remote Similarity	NPD8267	Approved
0.5736	Remote Similarity	NPD8266	Approved
0.5714	Remote Similarity	NPD6274	Approved
0.5714	Remote Similarity	NPD6033	Approved
0.5702	Remote Similarity	NPD6412	Phase 2
0.5691	Remote Similarity	NPD2067	Discontinued
0.568	Remote Similarity	NPD8133	Approved
0.5678	Remote Similarity	NPD1700	Approved
0.5655	Remote Similarity	NPD6190	Approved
0.5652	Remote Similarity	NPD73	Approved
0.5648	Remote Similarity	NPD5332	Approved
0.5648	Remote Similarity	NPD5331	Approved
0.5645	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5645	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.5636	Remote Similarity	NPD6422	Discontinued
0.563	Remote Similarity	NPD5211	Phase 2
0.563	Remote Similarity	NPD5956	Approved
0.5625	Remote Similarity	NPD7328	Approved
0.5625	Remote Similarity	NPD7327	Approved
0.5615	Remote Similarity	NPD7503	Approved
0.5615	Remote Similarity	NPD8033	Approved
0.5614	Remote Similarity	NPD6399	Phase 3
0.5607	Remote Similarity	NPD4790	Discontinued

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