NPASS Compound

Structure

NPC194941 OpenBabel07101718182D 28 30 0 0 1 0 0 0 0 0999 V2000 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2321 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1962 1.0000 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 4.3301 0.5000 0.0000 C 0 0 1 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 0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 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 9 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 4 18 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 7 10 1 0 0 0 0 7 18 1 0 0 0 0 8 20 1 0 0 0 0 9 21 2 0 0 0 0 10 15 1 0 0 0 0 10 22 1 6 0 0 0 11 8 1 1 0 0 0 11 12 1 0 0 0 0 11 26 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 6 0 0 0 13 14 1 0 0 0 0 13 24 1 1 0 0 0 14 16 1 0 0 0 0 14 25 1 6 0 0 0 15 17 1 0 0 0 0 15 27 1 1 0 0 0 16 26 1 0 0 0 0 16 27 1 1 0 0 0 17 19 1 0 0 0 0 18 19 1 6 0 0 0 18 28 1 0 0 0 0 19 6 1 6 0 0 0 19 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	402.19
Volume:	385.35
LogP:	-0.231
LogD:	-0.539
LogS:	-2.448
# Rotatable Bonds:	5
TPSA:	149.21
# H-Bond Aceptor:	9
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.277
Synthetic Accessibility Score:	4.907
Fsp3:	0.842
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:	-5.712
MDCK Permeability:	9.457517444388941e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.829
20% Bioavailability (F20%):	0.07
30% Bioavailability (F30%):	0.814

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	25.92235565185547%
Volume Distribution (VD):	0.526
Pgp-substrate:	55.783851623535156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.425
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.723
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.034
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.087
CYP3A4-inhibitor:	0.009
CYP3A4-substrate:	0.281

ADMET: Excretion

Clearance (CL):	1.642
Half-life (T1/2):	0.774

ADMET: Toxicity

hERG Blockers:	0.045
Human Hepatotoxicity (H-HT):	0.134
Drug-inuced Liver Injury (DILI):	0.404
AMES Toxicity:	0.789
Rat Oral Acute Toxicity:	0.307
Maximum Recommended Daily Dose:	0.005
Skin Sensitization:	0.685
Carcinogencity:	0.555
Eye Corrosion:	0.004
Eye Irritation:	0.121
Respiratory Toxicity:	0.556

Download Data

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

Natural Product: NPC194941

Natural Product ID:	NPC194941
*Common Name:**	(E)-4-[(1R,3R,4R,6S)-3-Hydroxy-1,5,5-Trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-7-Oxabicyclo[4.1.0]Heptan-6-Yl]But-3-En-2-One
IUPAC Name:	(E)-4-[(1R,3R,4R,6S)-3-hydroxy-1,5,5-trimethyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7-oxabicyclo[4.1.0]heptan-6-yl]but-3-en-2-one
Synonyms:
Standard InCHIKey:	BFLLXOGGWRRMBS-RRDFWYJBSA-N
Standard InCHI:	InChI=1S/C19H30O9/c1-9(21)5-6-19-17(2,3)15(10(22)7-18(19,4)28-19)27-16-14(25)13(24)12(23)11(8-20)26-16/h5-6,10-16,20,22-25H,7-8H2,1-4H3/b6-5+/t10-,11-,12-,13+,14-,15+,16+,18-,19+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@H]2[C@H](O)C[C@@]3([C@@](C2(C)C)(/C=C/C(=O)C)O3)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL511780
PubChem CID:	16086604
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO32690	salsola tetrandra	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989538]

☑ 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	1
MIC	5
Others	3

Activity Type	# Activity
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT176	Organism	Artemia salina	Artemia salina	ED50	=	10.9	uM	PMID[519476]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MBC	>	700.0	ug ml-1	PMID[519476]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	>	700.0	ug ml-1	PMID[519476]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	700.0	ug.mL-1	PMID[519476]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	600.0	ug.mL-1	PMID[519476]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	>	700.0	ug ml-1	PMID[519476]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	500.0	ug.mL-1	PMID[519476]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	700.0	ug.mL-1	PMID[519476]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	700.0	ug.mL-1	PMID[519476]

☑ 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 NPC194941 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	236
0.1-0.2	1768
0.2-0.3	5002
0.3-0.4	7904
0.4-0.5	14288
0.5-0.6	8160
0.6-0.7	4477
0.7-0.8	848
0.8-0.85	8
0.85-0.9	3
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC473068
0.9192	High Similarity	NPC214277
0.91	High Similarity	NPC473070
0.9082	High Similarity	NPC312325
0.8932	High Similarity	NPC473069
0.8812	High Similarity	NPC150463
0.8396	Intermediate Similarity	NPC181994
0.8173	Intermediate Similarity	NPC198992
0.8091	Intermediate Similarity	NPC470025
0.8091	Intermediate Similarity	NPC328074
0.8091	Intermediate Similarity	NPC321272
0.8091	Intermediate Similarity	NPC317460
0.8073	Intermediate Similarity	NPC46407
0.8073	Intermediate Similarity	NPC316708
0.807	Intermediate Similarity	NPC48692
0.8041	Intermediate Similarity	NPC34581
0.8037	Intermediate Similarity	NPC239961
0.8018	Intermediate Similarity	NPC470027
0.8	Intermediate Similarity	NPC17791
0.8	Intermediate Similarity	NPC154127
0.8	Intermediate Similarity	NPC470026
0.8	Intermediate Similarity	NPC280991
0.7982	Intermediate Similarity	NPC206618
0.7982	Intermediate Similarity	NPC257853
0.7963	Intermediate Similarity	NPC122816
0.7931	Intermediate Similarity	NPC196130
0.7931	Intermediate Similarity	NPC471082
0.7925	Intermediate Similarity	NPC121423
0.7909	Intermediate Similarity	NPC177047
0.7905	Intermediate Similarity	NPC79303
0.7899	Intermediate Similarity	NPC270109
0.7895	Intermediate Similarity	NPC234522
0.789	Intermediate Similarity	NPC38948
0.789	Intermediate Similarity	NPC128795
0.789	Intermediate Similarity	NPC217921
0.789	Intermediate Similarity	NPC135015
0.789	Intermediate Similarity	NPC48548
0.7876	Intermediate Similarity	NPC471816
0.787	Intermediate Similarity	NPC51719
0.787	Intermediate Similarity	NPC82251
0.7857	Intermediate Similarity	NPC264153
0.7857	Intermediate Similarity	NPC75167
0.7857	Intermediate Similarity	NPC311592
0.7857	Intermediate Similarity	NPC471267
0.7845	Intermediate Similarity	NPC233500
0.7835	Intermediate Similarity	NPC471987
0.783	Intermediate Similarity	NPC472554
0.7822	Intermediate Similarity	NPC474249
0.7822	Intermediate Similarity	NPC261990
0.7818	Intermediate Similarity	NPC316974
0.7818	Intermediate Similarity	NPC40728
0.7818	Intermediate Similarity	NPC472901
0.781	Intermediate Similarity	NPC61630
0.781	Intermediate Similarity	NPC307517
0.781	Intermediate Similarity	NPC169468
0.781	Intermediate Similarity	NPC81483
0.7807	Intermediate Similarity	NPC13713
0.7798	Intermediate Similarity	NPC109376
0.7798	Intermediate Similarity	NPC472390
0.7798	Intermediate Similarity	NPC125423
0.7798	Intermediate Similarity	NPC88013
0.7798	Intermediate Similarity	NPC471205
0.7788	Intermediate Similarity	NPC90583
0.7788	Intermediate Similarity	NPC181145
0.7778	Intermediate Similarity	NPC471937
0.7768	Intermediate Similarity	NPC473125
0.7757	Intermediate Similarity	NPC472552
0.7757	Intermediate Similarity	NPC201191
0.7757	Intermediate Similarity	NPC223834
0.7739	Intermediate Similarity	NPC83287
0.7736	Intermediate Similarity	NPC271295
0.7736	Intermediate Similarity	NPC16601
0.7731	Intermediate Similarity	NPC222307
0.7727	Intermediate Similarity	NPC38376
0.7727	Intermediate Similarity	NPC80210
0.7727	Intermediate Similarity	NPC470024
0.7727	Intermediate Similarity	NPC224660
0.7727	Intermediate Similarity	NPC311223
0.7719	Intermediate Similarity	NPC113425
0.7719	Intermediate Similarity	NPC232564
0.7714	Intermediate Similarity	NPC240372
0.7714	Intermediate Similarity	NPC309503
0.7714	Intermediate Similarity	NPC239547
0.7714	Intermediate Similarity	NPC155319
0.7714	Intermediate Similarity	NPC96597
0.7714	Intermediate Similarity	NPC91197
0.7714	Intermediate Similarity	NPC474194
0.7714	Intermediate Similarity	NPC120446
0.7714	Intermediate Similarity	NPC125551
0.7706	Intermediate Similarity	NPC470763
0.7706	Intermediate Similarity	NPC85670
0.7706	Intermediate Similarity	NPC218158
0.7706	Intermediate Similarity	NPC172867
0.7706	Intermediate Similarity	NPC470767
0.7699	Intermediate Similarity	NPC44298
0.7699	Intermediate Similarity	NPC290608
0.7699	Intermediate Similarity	NPC40133
0.7699	Intermediate Similarity	NPC49413
0.7699	Intermediate Similarity	NPC473128
0.7699	Intermediate Similarity	NPC473159
0.7692	Intermediate Similarity	NPC469583
0.7686	Intermediate Similarity	NPC104382
0.7685	Intermediate Similarity	NPC120009
0.7685	Intermediate Similarity	NPC474575
0.7685	Intermediate Similarity	NPC151516
0.7685	Intermediate Similarity	NPC281378
0.7685	Intermediate Similarity	NPC471938
0.7679	Intermediate Similarity	NPC472987
0.7679	Intermediate Similarity	NPC473021
0.7672	Intermediate Similarity	NPC219656
0.7672	Intermediate Similarity	NPC153085
0.7672	Intermediate Similarity	NPC268326
0.7672	Intermediate Similarity	NPC470914
0.767	Intermediate Similarity	NPC91654
0.767	Intermediate Similarity	NPC474792
0.767	Intermediate Similarity	NPC67398
0.7664	Intermediate Similarity	NPC11974
0.7658	Intermediate Similarity	NPC475586
0.7658	Intermediate Similarity	NPC195116
0.7658	Intermediate Similarity	NPC221110
0.7658	Intermediate Similarity	NPC180459
0.7658	Intermediate Similarity	NPC28844
0.7658	Intermediate Similarity	NPC473328
0.7658	Intermediate Similarity	NPC473318
0.7658	Intermediate Similarity	NPC285253
0.7652	Intermediate Similarity	NPC84987
0.7652	Intermediate Similarity	NPC196429
0.7652	Intermediate Similarity	NPC471355
0.7652	Intermediate Similarity	NPC471353
0.7652	Intermediate Similarity	NPC290693
0.7652	Intermediate Similarity	NPC99728
0.7652	Intermediate Similarity	NPC87250
0.7652	Intermediate Similarity	NPC50305
0.7652	Intermediate Similarity	NPC27507
0.7652	Intermediate Similarity	NPC471354
0.7652	Intermediate Similarity	NPC473852
0.7652	Intermediate Similarity	NPC158344
0.7652	Intermediate Similarity	NPC243196
0.7652	Intermediate Similarity	NPC203862
0.7652	Intermediate Similarity	NPC474418
0.7652	Intermediate Similarity	NPC142066
0.7652	Intermediate Similarity	NPC152615
0.7652	Intermediate Similarity	NPC309034
0.7652	Intermediate Similarity	NPC471351
0.7652	Intermediate Similarity	NPC34390
0.7652	Intermediate Similarity	NPC157376
0.7652	Intermediate Similarity	NPC77319
0.7652	Intermediate Similarity	NPC244402
0.7642	Intermediate Similarity	NPC477928
0.7636	Intermediate Similarity	NPC33053
0.7632	Intermediate Similarity	NPC475163
0.7627	Intermediate Similarity	NPC115349
0.7619	Intermediate Similarity	NPC472997
0.7619	Intermediate Similarity	NPC472995
0.7619	Intermediate Similarity	NPC472996
0.7615	Intermediate Similarity	NPC470768
0.7611	Intermediate Similarity	NPC174836
0.7607	Intermediate Similarity	NPC135369
0.7607	Intermediate Similarity	NPC475136
0.7607	Intermediate Similarity	NPC474466
0.7596	Intermediate Similarity	NPC72817
0.7596	Intermediate Similarity	NPC2003
0.7596	Intermediate Similarity	NPC25701
0.7596	Intermediate Similarity	NPC477927
0.7593	Intermediate Similarity	NPC11956
0.7593	Intermediate Similarity	NPC470571
0.7593	Intermediate Similarity	NPC472815
0.7593	Intermediate Similarity	NPC471914
0.7593	Intermediate Similarity	NPC475038
0.7593	Intermediate Similarity	NPC109195
0.7593	Intermediate Similarity	NPC470972
0.7589	Intermediate Similarity	NPC170974
0.7589	Intermediate Similarity	NPC191439
0.7589	Intermediate Similarity	NPC83005
0.7589	Intermediate Similarity	NPC103627
0.7589	Intermediate Similarity	NPC119550
0.7589	Intermediate Similarity	NPC65155
0.7586	Intermediate Similarity	NPC470515
0.7586	Intermediate Similarity	NPC473617
0.7586	Intermediate Similarity	NPC473828
0.7573	Intermediate Similarity	NPC289361
0.757	Intermediate Similarity	NPC38855
0.757	Intermediate Similarity	NPC324841
0.757	Intermediate Similarity	NPC64348
0.757	Intermediate Similarity	NPC188968
0.7568	Intermediate Similarity	NPC272576
0.7568	Intermediate Similarity	NPC177524
0.7568	Intermediate Similarity	NPC469916
0.7568	Intermediate Similarity	NPC472439
0.7568	Intermediate Similarity	NPC392
0.7568	Intermediate Similarity	NPC219900
0.7565	Intermediate Similarity	NPC193382
0.7565	Intermediate Similarity	NPC99620
0.7565	Intermediate Similarity	NPC310341
0.7565	Intermediate Similarity	NPC207637
0.7565	Intermediate Similarity	NPC199428
0.7565	Intermediate Similarity	NPC5311
0.7561	Intermediate Similarity	NPC231240
0.7551	Intermediate Similarity	NPC259858
0.7549	Intermediate Similarity	NPC82876

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 NPC194941 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	2010
0.2-0.3	3946
0.3-0.4	1986
0.4-0.5	644
0.5-0.6	284
0.6-0.7	62
0.7-0.8	8
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
0.8	Intermediate Similarity	NPD5344	Discontinued
0.7826	Intermediate Similarity	NPD7516	Approved
0.7739	Intermediate Similarity	NPD7328	Approved
0.7739	Intermediate Similarity	NPD7327	Approved
0.757	Intermediate Similarity	NPD6648	Approved
0.7568	Intermediate Similarity	NPD6686	Approved
0.7395	Intermediate Similarity	NPD8296	Approved
0.7395	Intermediate Similarity	NPD8335	Approved
0.7395	Intermediate Similarity	NPD8380	Approved
0.7395	Intermediate Similarity	NPD8379	Approved
0.7395	Intermediate Similarity	NPD7503	Approved
0.7395	Intermediate Similarity	NPD8378	Approved
0.7395	Intermediate Similarity	NPD8033	Approved
0.7345	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD8294	Approved
0.7311	Intermediate Similarity	NPD8377	Approved
0.713	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.6984	Remote Similarity	NPD7319	Approved
0.6981	Remote Similarity	NPD7838	Discovery
0.6957	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.687	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6412	Phase 2
0.6847	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD3168	Discontinued
0.6822	Remote Similarity	NPD46	Approved
0.6822	Remote Similarity	NPD6698	Approved
0.6777	Remote Similarity	NPD7115	Discovery
0.664	Remote Similarity	NPD6370	Approved
0.6587	Remote Similarity	NPD8328	Phase 3
0.6549	Remote Similarity	NPD7638	Approved
0.6529	Remote Similarity	NPD8133	Approved
0.6491	Remote Similarity	NPD7639	Approved
0.6491	Remote Similarity	NPD7640	Approved
0.648	Remote Similarity	NPD6054	Approved
0.6457	Remote Similarity	NPD7642	Approved
0.6429	Remote Similarity	NPD8517	Approved
0.6429	Remote Similarity	NPD6921	Approved
0.6429	Remote Similarity	NPD8515	Approved
0.6429	Remote Similarity	NPD8516	Approved
0.6429	Remote Similarity	NPD6015	Approved
0.6429	Remote Similarity	NPD8513	Phase 3
0.6429	Remote Similarity	NPD6016	Approved
0.6415	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7524	Approved
0.6385	Remote Similarity	NPD7736	Approved
0.6378	Remote Similarity	NPD5988	Approved
0.6371	Remote Similarity	NPD6009	Approved
0.6371	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6319	Approved
0.6328	Remote Similarity	NPD7829	Approved
0.6328	Remote Similarity	NPD7830	Approved
0.6311	Remote Similarity	NPD6882	Approved
0.6293	Remote Similarity	NPD4159	Approved
0.6281	Remote Similarity	NPD6371	Approved
0.6279	Remote Similarity	NPD7492	Approved
0.6263	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.626	Remote Similarity	NPD4632	Approved
0.6231	Remote Similarity	NPD6616	Approved
0.623	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.622	Remote Similarity	NPD6059	Approved
0.6218	Remote Similarity	NPD5357	Phase 1
0.6183	Remote Similarity	NPD8293	Discontinued
0.6183	Remote Similarity	NPD7078	Approved
0.6179	Remote Similarity	NPD8297	Approved
0.6111	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD7632	Discontinued
0.6102	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD7625	Phase 1
0.6077	Remote Similarity	NPD6067	Discontinued
0.6033	Remote Similarity	NPD5697	Approved
0.6019	Remote Similarity	NPD6695	Phase 3
0.6016	Remote Similarity	NPD4634	Approved
0.5984	Remote Similarity	NPD6881	Approved
0.5984	Remote Similarity	NPD6899	Approved
0.5968	Remote Similarity	NPD6650	Approved
0.5968	Remote Similarity	NPD6649	Approved
0.5966	Remote Similarity	NPD5211	Phase 2
0.5954	Remote Similarity	NPD7604	Phase 2
0.595	Remote Similarity	NPD6008	Approved
0.594	Remote Similarity	NPD8074	Phase 3
0.5935	Remote Similarity	NPD6013	Approved
0.5935	Remote Similarity	NPD6012	Approved
0.5935	Remote Similarity	NPD6014	Approved
0.5932	Remote Similarity	NPD5285	Approved
0.5932	Remote Similarity	NPD4696	Approved
0.5932	Remote Similarity	NPD5286	Approved
0.5923	Remote Similarity	NPD5983	Phase 2
0.5922	Remote Similarity	NPD1810	Approved
0.5922	Remote Similarity	NPD1811	Approved
0.5913	Remote Similarity	NPD5282	Discontinued
0.5909	Remote Similarity	NPD1694	Approved
0.5902	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5887	Remote Similarity	NPD7102	Approved
0.5887	Remote Similarity	NPD7290	Approved
0.5887	Remote Similarity	NPD6883	Approved
0.5877	Remote Similarity	NPD7637	Suspended
0.5872	Remote Similarity	NPD3669	Approved
0.5872	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD5141	Approved
0.5865	Remote Similarity	NPD8451	Approved
0.5854	Remote Similarity	NPD6011	Approved
0.584	Remote Similarity	NPD6847	Approved
0.584	Remote Similarity	NPD6617	Approved
0.584	Remote Similarity	NPD6869	Approved
0.584	Remote Similarity	NPD8130	Phase 1
0.5833	Remote Similarity	NPD5226	Approved
0.5833	Remote Similarity	NPD4633	Approved
0.5833	Remote Similarity	NPD5225	Approved
0.5833	Remote Similarity	NPD5224	Approved
0.5826	Remote Similarity	NPD8171	Discontinued
0.5821	Remote Similarity	NPD8448	Approved
0.582	Remote Similarity	NPD6402	Approved
0.582	Remote Similarity	NPD7128	Approved
0.582	Remote Similarity	NPD5739	Approved
0.582	Remote Similarity	NPD6675	Approved
0.5816	Remote Similarity	NPD371	Approved
0.5814	Remote Similarity	NPD7641	Discontinued
0.5806	Remote Similarity	NPD6373	Approved
0.5806	Remote Similarity	NPD6372	Approved
0.5804	Remote Similarity	NPD7750	Discontinued
0.5802	Remote Similarity	NPD8444	Approved
0.5785	Remote Similarity	NPD5175	Approved
0.5785	Remote Similarity	NPD5174	Approved
0.578	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.5778	Remote Similarity	NPD6033	Approved
0.5776	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD7748	Approved
0.5772	Remote Similarity	NPD5701	Approved
0.5766	Remote Similarity	NPD7260	Phase 2
0.5766	Remote Similarity	NPD1696	Phase 3
0.5764	Remote Similarity	NPD7266	Discontinued
0.5763	Remote Similarity	NPD7902	Approved
0.5763	Remote Similarity	NPD4755	Approved
0.5758	Remote Similarity	NPD5126	Approved
0.5758	Remote Similarity	NPD5125	Phase 3
0.575	Remote Similarity	NPD5223	Approved
0.5746	Remote Similarity	NPD6336	Discontinued
0.5741	Remote Similarity	NPD7525	Registered
0.5741	Remote Similarity	NPD7332	Phase 2
0.5741	Remote Similarity	NPD6931	Approved
0.5741	Remote Similarity	NPD7514	Phase 3
0.5741	Remote Similarity	NPD6930	Phase 2
0.5739	Remote Similarity	NPD7515	Phase 2
0.5739	Remote Similarity	NPD6079	Approved
0.5739	Remote Similarity	NPD7983	Approved
0.5738	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD4730	Approved
0.5726	Remote Similarity	NPD4729	Approved
0.5726	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD7320	Approved
0.5725	Remote Similarity	NPD8338	Approved
0.5714	Remote Similarity	NPD3618	Phase 1
0.5693	Remote Similarity	NPD8392	Approved
0.5693	Remote Similarity	NPD8391	Approved
0.5693	Remote Similarity	NPD8390	Approved
0.5693	Remote Similarity	NPD5956	Approved
0.569	Remote Similarity	NPD4202	Approved
0.569	Remote Similarity	NPD5778	Approved
0.569	Remote Similarity	NPD5779	Approved
0.5688	Remote Similarity	NPD6902	Approved
0.5678	Remote Similarity	NPD5221	Approved
0.5678	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5678	Remote Similarity	NPD5222	Approved
0.5674	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5672	Remote Similarity	NPD8340	Approved
0.5672	Remote Similarity	NPD8342	Approved
0.5672	Remote Similarity	NPD8341	Approved
0.5672	Remote Similarity	NPD8299	Approved
0.5669	Remote Similarity	NPD6053	Discontinued
0.5667	Remote Similarity	NPD4700	Approved
0.5664	Remote Similarity	NPD3573	Approved
0.5652	Remote Similarity	NPD8522	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD5785	Approved
0.5648	Remote Similarity	NPD6929	Approved
0.5648	Remote Similarity	NPD7645	Phase 2
0.5635	Remote Similarity	NPD5248	Approved
0.5635	Remote Similarity	NPD5247	Approved
0.5635	Remote Similarity	NPD5251	Approved
0.5635	Remote Similarity	NPD5250	Approved
0.5635	Remote Similarity	NPD5249	Phase 3
0.5631	Remote Similarity	NPD2687	Approved
0.5631	Remote Similarity	NPD2254	Approved
0.5631	Remote Similarity	NPD2686	Approved
0.563	Remote Similarity	NPD5173	Approved
0.5607	Remote Similarity	NPD6932	Approved
0.5603	Remote Similarity	NPD6411	Approved
0.5603	Remote Similarity	NPD7087	Discontinued
0.56	Remote Similarity	NPD2685	Clinical (unspecified phase)

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