NPASS Compound

Structure

NPC90583 OpenBabel07101719252D 34 36 0 0 1 0 0 0 0 0999 V2000 6.9282 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0981 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6603 -0.0000 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 6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 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 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5263 0.5000 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 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 5.6962 3.8660 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 1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 24 1 0 0 0 0 3 24 1 0 0 0 0 6 7 1 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 12 1 0 0 0 0 8 17 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 15 2 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 27 1 0 0 0 0 14 28 1 0 0 0 0 16 14 1 6 0 0 0 16 20 1 0 0 0 0 16 33 1 0 0 0 0 17 24 1 0 0 0 0 17 25 1 6 0 0 0 18 25 1 6 0 0 0 18 26 1 0 0 0 0 19 24 1 0 0 0 0 19 34 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 22 1 0 0 0 0 21 30 1 6 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 33 1 0 0 0 0 23 34 1 6 0 0 0 25 4 1 6 0 0 0 26 5 1 1 0 0 0 26 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	486.32
Volume:	500.268
LogP:	1.917
LogD:	2.456
LogS:	-3.554
# Rotatable Bonds:	7
TPSA:	139.84
# H-Bond Aceptor:	8
# H-Bond Donor:	6
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.235
Synthetic Accessibility Score:	4.8
Fsp3:	0.923
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.222
MDCK Permeability:	7.300495053641498e-05
Pgp-inhibitor:	0.935
Pgp-substrate:	0.598
Human Intestinal Absorption (HIA):	0.926
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.31

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	67.21637725830078%
Volume Distribution (VD):	0.607
Pgp-substrate:	25.771909713745117%

ADMET: Metabolism

CYP1A2-inhibitor:	0.005
CYP1A2-substrate:	0.121
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.597
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.026
CYP3A4-substrate:	0.096

ADMET: Excretion

Clearance (CL):	1.631
Half-life (T1/2):	0.822

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.009
AMES Toxicity:	0.048
Rat Oral Acute Toxicity:	0.102
Maximum Recommended Daily Dose:	0.206
Skin Sensitization:	0.675
Carcinogencity:	0.016
Eye Corrosion:	0.003
Eye Irritation:	0.036
Respiratory Toxicity:	0.959

Download Data

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

Natural Product: NPC90583

Natural Product ID:	NPC90583
*Common Name:**	Tricalysioside U
IUPAC Name:	(2R,3R,4S,5S,6R)-2-[[(2S,4aS,5R,6S,8aR)-6-hydroxy-5-[(E)-5-hydroxy-3-methylpent-3-enyl]-1,1,4a,6-tetramethyl-3,4,5,7,8,8a-hexahydro-2H-naphthalen-2-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Synonyms:	Tricalysioside U
Standard InCHIKey:	FCBACUGWODQDAW-ITGYZVCLSA-N
Standard InCHI:	InChI=1S/C26H46O8/c1-15(10-13-27)6-7-18-25(4)11-9-19(24(2,3)17(25)8-12-26(18,5)32)34-23-22(31)21(30)20(29)16(14-28)33-23/h10,16-23,27-32H,6-9,11-14H2,1-5H3/b15-10+/t16-,17+,18-,19+,20-,21+,22-,23+,25+,26+/m1/s1
SMILES:	C/C(=CCO)/CC[C@@H]1[C@@]2(C)CC[C@@H](C(C)(C)[C@@H]2CC[C@]1(C)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2036085
PubChem CID:	24749805
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001755] Diterpene glycosides

*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
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22413887]
NPO32523	solanum violaceum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23511021]

☑ 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	6

Activity Type	# Activity
Cell Line	5
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[500062]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[500062]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[500062]
NPT1031	Cell Line	Ca9-22	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[500062]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[500062]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	20.0	ug.mL-1	PMID[500062]

☑ 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 NPC90583 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	1738
0.2-0.3	4941
0.3-0.4	10981
0.4-0.5	11415
0.5-0.6	6197
0.6-0.7	4601
0.7-0.8	2310
0.8-0.85	208
0.85-0.9	52
0.9-0.95	15
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9457	High Similarity	NPC240372
0.9333	High Similarity	NPC302584
0.9255	High Similarity	NPC64348
0.9175	High Similarity	NPC472900
0.9175	High Similarity	NPC472899
0.9175	High Similarity	NPC472898
0.9167	High Similarity	NPC162354
0.913	High Similarity	NPC305160
0.913	High Similarity	NPC477927
0.913	High Similarity	NPC72817
0.9082	High Similarity	NPC231340
0.9072	High Similarity	NPC75608
0.9062	High Similarity	NPC470571
0.8969	High Similarity	NPC473198
0.8969	High Similarity	NPC473123
0.8969	High Similarity	NPC473124
0.8958	High Similarity	NPC88000
0.8958	High Similarity	NPC472023
0.8958	High Similarity	NPC160734
0.8958	High Similarity	NPC47566
0.8958	High Similarity	NPC129372
0.8958	High Similarity	NPC4831
0.8958	High Similarity	NPC309425
0.8925	High Similarity	NPC211238
0.8878	High Similarity	NPC110656
0.8878	High Similarity	NPC203354
0.8878	High Similarity	NPC473127
0.8878	High Similarity	NPC470768
0.8866	High Similarity	NPC136816
0.8854	High Similarity	NPC7341
0.8854	High Similarity	NPC473200
0.8817	High Similarity	NPC91654
0.8817	High Similarity	NPC474792
0.8817	High Similarity	NPC67398
0.8804	High Similarity	NPC261990
0.8804	High Similarity	NPC474249
0.88	High Similarity	NPC472896
0.88	High Similarity	NPC472897
0.8788	High Similarity	NPC470763
0.8788	High Similarity	NPC470767
0.8776	High Similarity	NPC31907
0.8776	High Similarity	NPC155010
0.8776	High Similarity	NPC472252
0.8776	High Similarity	NPC16520
0.8776	High Similarity	NPC8039
0.8776	High Similarity	NPC211879
0.8776	High Similarity	NPC473020
0.8776	High Similarity	NPC213190
0.8776	High Similarity	NPC131479
0.8776	High Similarity	NPC157659
0.8776	High Similarity	NPC245280
0.8776	High Similarity	NPC189852
0.8776	High Similarity	NPC120123
0.8776	High Similarity	NPC286969
0.8776	High Similarity	NPC114874
0.8763	High Similarity	NPC470434
0.8763	High Similarity	NPC263756
0.8763	High Similarity	NPC117714
0.875	High Similarity	NPC216260
0.875	High Similarity	NPC5358
0.875	High Similarity	NPC234287
0.875	High Similarity	NPC280825
0.875	High Similarity	NPC477928
0.875	High Similarity	NPC476895
0.8723	High Similarity	NPC96736
0.8723	High Similarity	NPC178949
0.8713	High Similarity	NPC472901
0.87	High Similarity	NPC281939
0.87	High Similarity	NPC33053
0.8687	High Similarity	NPC470885
0.8687	High Similarity	NPC221562
0.8687	High Similarity	NPC273879
0.8687	High Similarity	NPC93352
0.8687	High Similarity	NPC165033
0.8687	High Similarity	NPC187400
0.8673	High Similarity	NPC288694
0.8673	High Similarity	NPC213674
0.8673	High Similarity	NPC312553
0.8673	High Similarity	NPC256133
0.8673	High Similarity	NPC76497
0.8673	High Similarity	NPC30289
0.8673	High Similarity	NPC159036
0.866	High Similarity	NPC469942
0.8646	High Similarity	NPC476893
0.8641	High Similarity	NPC216595
0.8641	High Similarity	NPC473567
0.8627	High Similarity	NPC170974
0.8627	High Similarity	NPC191439
0.8627	High Similarity	NPC103627
0.8627	High Similarity	NPC65155
0.8614	High Similarity	NPC38376
0.8614	High Similarity	NPC80210
0.8614	High Similarity	NPC235824
0.86	High Similarity	NPC208477
0.86	High Similarity	NPC160816
0.86	High Similarity	NPC152584
0.86	High Similarity	NPC473199
0.86	High Similarity	NPC69737
0.86	High Similarity	NPC269627
0.86	High Similarity	NPC127801
0.86	High Similarity	NPC194842
0.86	High Similarity	NPC208594
0.8586	High Similarity	NPC123796
0.8586	High Similarity	NPC473129
0.8586	High Similarity	NPC99627
0.8586	High Similarity	NPC16573
0.8571	High Similarity	NPC476896
0.8571	High Similarity	NPC280991
0.8557	High Similarity	NPC312325
0.8556	High Similarity	NPC166279
0.8544	High Similarity	NPC472987
0.8544	High Similarity	NPC473021
0.8542	High Similarity	NPC472989
0.8529	High Similarity	NPC14630
0.8529	High Similarity	NPC285253
0.8529	High Similarity	NPC473318
0.8529	High Similarity	NPC473328
0.8529	High Similarity	NPC157530
0.8529	High Similarity	NPC250089
0.8529	High Similarity	NPC221110
0.8529	High Similarity	NPC28844
0.8529	High Similarity	NPC180459
0.8529	High Similarity	NPC195116
0.8515	High Similarity	NPC208650
0.8515	High Similarity	NPC472390
0.8515	High Similarity	NPC63368
0.8515	High Similarity	NPC181467
0.8515	High Similarity	NPC190395
0.8515	High Similarity	NPC14946
0.8511	High Similarity	NPC289361
0.85	High Similarity	NPC473734
0.85	High Similarity	NPC471434
0.85	High Similarity	NPC109792
0.85	High Similarity	NPC57065
0.85	High Similarity	NPC54521
0.85	High Similarity	NPC173583
0.85	High Similarity	NPC471435
0.85	High Similarity	NPC148603
0.85	High Similarity	NPC230948
0.8495	Intermediate Similarity	NPC477917
0.8495	Intermediate Similarity	NPC473058
0.8485	Intermediate Similarity	NPC150463
0.8485	Intermediate Similarity	NPC214277
0.8469	Intermediate Similarity	NPC324598
0.8469	Intermediate Similarity	NPC91497
0.8462	Intermediate Similarity	NPC231797
0.8454	Intermediate Similarity	NPC125551
0.8454	Intermediate Similarity	NPC243728
0.8454	Intermediate Similarity	NPC96597
0.8454	Intermediate Similarity	NPC309503
0.8454	Intermediate Similarity	NPC91197
0.8454	Intermediate Similarity	NPC26307
0.8454	Intermediate Similarity	NPC155319
0.8454	Intermediate Similarity	NPC473890
0.8454	Intermediate Similarity	NPC239547
0.8447	Intermediate Similarity	NPC472717
0.8438	Intermediate Similarity	NPC476894
0.8431	Intermediate Similarity	NPC220427
0.8431	Intermediate Similarity	NPC180183
0.8431	Intermediate Similarity	NPC246124
0.8431	Intermediate Similarity	NPC38217
0.8431	Intermediate Similarity	NPC472988
0.8431	Intermediate Similarity	NPC6931
0.8431	Intermediate Similarity	NPC159005
0.8416	Intermediate Similarity	NPC138057
0.8416	Intermediate Similarity	NPC242748
0.8416	Intermediate Similarity	NPC470512
0.8416	Intermediate Similarity	NPC173859
0.8416	Intermediate Similarity	NPC26798
0.8416	Intermediate Similarity	NPC309448
0.8404	Intermediate Similarity	NPC159876
0.8396	Intermediate Similarity	NPC146652
0.8387	Intermediate Similarity	NPC248312
0.8384	Intermediate Similarity	NPC285231
0.8384	Intermediate Similarity	NPC21568
0.8367	Intermediate Similarity	NPC158088
0.8365	Intermediate Similarity	NPC65034
0.8365	Intermediate Similarity	NPC157474
0.8365	Intermediate Similarity	NPC208189
0.8365	Intermediate Similarity	NPC472715
0.8365	Intermediate Similarity	NPC110494
0.8351	Intermediate Similarity	NPC207617
0.835	Intermediate Similarity	NPC154085
0.835	Intermediate Similarity	NPC43976
0.835	Intermediate Similarity	NPC125361
0.835	Intermediate Similarity	NPC296761
0.835	Intermediate Similarity	NPC51925
0.835	Intermediate Similarity	NPC206618
0.835	Intermediate Similarity	NPC302057
0.8333	Intermediate Similarity	NPC226642
0.8333	Intermediate Similarity	NPC78034
0.8333	Intermediate Similarity	NPC234160
0.8333	Intermediate Similarity	NPC476594
0.8333	Intermediate Similarity	NPC473469
0.8333	Intermediate Similarity	NPC257964
0.8317	Intermediate Similarity	NPC31430
0.8317	Intermediate Similarity	NPC475365
0.8317	Intermediate Similarity	NPC85593
0.8317	Intermediate Similarity	NPC312774
0.8302	Intermediate Similarity	NPC472274

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 NPC90583 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	202
0.1-0.2	1964
0.2-0.3	3905
0.3-0.4	2005
0.4-0.5	652
0.5-0.6	263
0.6-0.7	134
0.7-0.8	25
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
0.8073	Intermediate Similarity	NPD7328	Approved
0.8073	Intermediate Similarity	NPD7327	Approved
0.8	Intermediate Similarity	NPD7516	Approved
0.7928	Intermediate Similarity	NPD8294	Approved
0.7928	Intermediate Similarity	NPD8377	Approved
0.7905	Intermediate Similarity	NPD6686	Approved
0.7857	Intermediate Similarity	NPD8033	Approved
0.7857	Intermediate Similarity	NPD8296	Approved
0.7857	Intermediate Similarity	NPD8335	Approved
0.7857	Intermediate Similarity	NPD8380	Approved
0.7857	Intermediate Similarity	NPD8379	Approved
0.7857	Intermediate Similarity	NPD8378	Approved
0.7699	Intermediate Similarity	NPD7503	Approved
0.7664	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD6412	Phase 2
0.7586	Intermediate Similarity	NPD7507	Approved
0.7395	Intermediate Similarity	NPD7319	Approved
0.7387	Intermediate Similarity	NPD8133	Approved
0.7347	Intermediate Similarity	NPD7524	Approved
0.734	Intermediate Similarity	NPD7525	Registered
0.7265	Intermediate Similarity	NPD8328	Phase 3
0.7238	Intermediate Similarity	NPD7640	Approved
0.7238	Intermediate Similarity	NPD7639	Approved
0.7234	Intermediate Similarity	NPD7645	Phase 2
0.7216	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7638	Approved
0.7113	Intermediate Similarity	NPD6695	Phase 3
0.7034	Intermediate Similarity	NPD6370	Approved
0.7009	Intermediate Similarity	NPD5344	Discontinued
0.699	Remote Similarity	NPD8171	Discontinued
0.6981	Remote Similarity	NPD4225	Approved
0.6949	Remote Similarity	NPD8517	Approved
0.6949	Remote Similarity	NPD8513	Phase 3
0.6949	Remote Similarity	NPD8516	Approved
0.6949	Remote Similarity	NPD8515	Approved
0.6882	Remote Similarity	NPD1811	Approved
0.6882	Remote Similarity	NPD1810	Approved
0.6875	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD6059	Approved
0.6864	Remote Similarity	NPD6054	Approved
0.6832	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD7750	Discontinued
0.6804	Remote Similarity	NPD6931	Approved
0.6804	Remote Similarity	NPD6930	Phase 2
0.6803	Remote Similarity	NPD8293	Discontinued
0.6796	Remote Similarity	NPD3168	Discontinued
0.6786	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD7736	Approved
0.6701	Remote Similarity	NPD6929	Approved
0.6696	Remote Similarity	NPD6882	Approved
0.6694	Remote Similarity	NPD6067	Discontinued
0.6667	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6015	Approved
0.6639	Remote Similarity	NPD7492	Approved
0.6636	Remote Similarity	NPD7632	Discontinued
0.6633	Remote Similarity	NPD7332	Phase 2
0.6633	Remote Similarity	NPD7514	Phase 3
0.6632	Remote Similarity	NPD7339	Approved
0.6632	Remote Similarity	NPD6942	Approved
0.6612	Remote Similarity	NPD5988	Approved
0.661	Remote Similarity	NPD6009	Approved
0.661	Remote Similarity	NPD7115	Discovery
0.6609	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6648	Approved
0.6585	Remote Similarity	NPD6616	Approved
0.6583	Remote Similarity	NPD6319	Approved
0.6571	Remote Similarity	NPD7087	Discontinued
0.6562	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6933	Approved
0.6559	Remote Similarity	NPD2686	Approved
0.6559	Remote Similarity	NPD2687	Approved
0.6559	Remote Similarity	NPD2254	Approved
0.6552	Remote Similarity	NPD8297	Approved
0.6535	Remote Similarity	NPD8449	Approved
0.6532	Remote Similarity	NPD7078	Approved
0.6496	Remote Similarity	NPD4632	Approved
0.6495	Remote Similarity	NPD6925	Approved
0.6495	Remote Similarity	NPD5776	Phase 2
0.6484	Remote Similarity	NPD8450	Suspended
0.6476	Remote Similarity	NPD46	Approved
0.6476	Remote Similarity	NPD6698	Approved
0.6471	Remote Similarity	NPD6893	Approved
0.6465	Remote Similarity	NPD6928	Phase 2
0.646	Remote Similarity	NPD7128	Approved
0.646	Remote Similarity	NPD6675	Approved
0.646	Remote Similarity	NPD6402	Approved
0.646	Remote Similarity	NPD5739	Approved
0.6458	Remote Similarity	NPD8264	Approved
0.6449	Remote Similarity	NPD7748	Approved
0.6436	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD3669	Approved
0.6435	Remote Similarity	NPD6373	Approved
0.6435	Remote Similarity	NPD6372	Approved
0.6429	Remote Similarity	NPD7145	Approved
0.6422	Remote Similarity	NPD7902	Approved
0.6415	Remote Similarity	NPD7637	Suspended
0.6415	Remote Similarity	NPD7515	Phase 2
0.6404	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6902	Approved
0.64	Remote Similarity	NPD6898	Phase 1
0.64	Remote Similarity	NPD8074	Phase 3
0.6397	Remote Similarity	NPD7625	Phase 1
0.6396	Remote Similarity	NPD4159	Approved
0.6383	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD6399	Phase 3
0.6354	Remote Similarity	NPD6926	Approved
0.6354	Remote Similarity	NPD6924	Approved
0.6349	Remote Similarity	NPD6033	Approved
0.6348	Remote Similarity	NPD6881	Approved
0.6348	Remote Similarity	NPD6899	Approved
0.6348	Remote Similarity	NPD7320	Approved
0.6339	Remote Similarity	NPD5211	Phase 2
0.6327	Remote Similarity	NPD6932	Approved
0.6325	Remote Similarity	NPD6649	Approved
0.6325	Remote Similarity	NPD6650	Approved
0.6321	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7838	Discovery
0.6316	Remote Similarity	NPD5357	Phase 1
0.63	Remote Similarity	NPD7509	Discontinued
0.6277	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4755	Approved
0.6264	Remote Similarity	NPD371	Approved
0.6263	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD7983	Approved
0.6261	Remote Similarity	NPD5697	Approved
0.6261	Remote Similarity	NPD5701	Approved
0.626	Remote Similarity	NPD6921	Approved
0.625	Remote Similarity	NPD3618	Phase 1
0.6239	Remote Similarity	NPD4634	Approved
0.6239	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD7102	Approved
0.6239	Remote Similarity	NPD7290	Approved
0.6228	Remote Similarity	NPD5141	Approved
0.6226	Remote Similarity	NPD5328	Approved
0.6226	Remote Similarity	NPD6051	Approved
0.6222	Remote Similarity	NPD368	Approved
0.6214	Remote Similarity	NPD4786	Approved
0.621	Remote Similarity	NPD5125	Phase 3
0.621	Remote Similarity	NPD5126	Approved
0.6204	Remote Similarity	NPD5779	Approved
0.6204	Remote Similarity	NPD4202	Approved
0.6204	Remote Similarity	NPD5778	Approved
0.62	Remote Similarity	NPD6683	Phase 2
0.6186	Remote Similarity	NPD6869	Approved
0.6186	Remote Similarity	NPD6617	Approved
0.6186	Remote Similarity	NPD6847	Approved
0.6186	Remote Similarity	NPD8130	Phase 1
0.6176	Remote Similarity	NPD3667	Approved
0.6174	Remote Similarity	NPD6640	Phase 3
0.6161	Remote Similarity	NPD4700	Approved
0.6161	Remote Similarity	NPD5286	Approved
0.6161	Remote Similarity	NPD5285	Approved
0.6161	Remote Similarity	NPD4696	Approved
0.616	Remote Similarity	NPD7604	Phase 2
0.6154	Remote Similarity	NPD6012	Approved
0.6154	Remote Similarity	NPD6013	Approved
0.6154	Remote Similarity	NPD6014	Approved
0.6147	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD7900	Approved
0.6146	Remote Similarity	NPD4243	Approved
0.6134	Remote Similarity	NPD6430	Approved
0.6134	Remote Similarity	NPD6429	Approved
0.6129	Remote Similarity	NPD5983	Phase 2
0.6126	Remote Similarity	NPD6084	Phase 2
0.6126	Remote Similarity	NPD6083	Phase 2
0.6111	Remote Similarity	NPD6411	Approved
0.6111	Remote Similarity	NPD6079	Approved
0.6111	Remote Similarity	NPD8034	Phase 2
0.6111	Remote Similarity	NPD8035	Phase 2
0.6068	Remote Similarity	NPD6011	Approved
0.6063	Remote Similarity	NPD6336	Discontinued
0.6053	Remote Similarity	NPD5226	Approved
0.6053	Remote Similarity	NPD4633	Approved
0.6053	Remote Similarity	NPD5224	Approved
0.6053	Remote Similarity	NPD5225	Approved
0.605	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6034	Remote Similarity	NPD6008	Approved
0.6034	Remote Similarity	NPD4768	Approved
0.6034	Remote Similarity	NPD4767	Approved
0.602	Remote Similarity	NPD4785	Approved
0.602	Remote Similarity	NPD4784	Approved
0.6	Remote Similarity	NPD5175	Approved
0.6	Remote Similarity	NPD5174	Approved
0.6	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD8342	Approved
0.5984	Remote Similarity	NPD8340	Approved
0.5984	Remote Similarity	NPD8299	Approved
0.5984	Remote Similarity	NPD8341	Approved
0.598	Remote Similarity	NPD4748	Discontinued
0.5979	Remote Similarity	NPD7151	Approved
0.5979	Remote Similarity	NPD7150	Approved
0.5979	Remote Similarity	NPD7152	Approved
0.5971	Remote Similarity	NPD6674	Discontinued
0.5966	Remote Similarity	NPD6371	Approved
0.5965	Remote Similarity	NPD5223	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