NPASS Compound

Structure

NPC57072 OpenBabel07101718282D 41 44 0 0 1 0 0 0 0 0999 V2000 -5.9275 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9275 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0807 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -3.4222 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8933 1.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9488 1.6359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2339 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8468 -1.4667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -2.9333 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5846 1.1975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9556 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9778 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6957 0.6914 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8468 1.4667 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6936 0.9778 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6936 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3316 0.2531 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3871 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -0.4889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5403 -0.4889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3871 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8468 2.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -3.4222 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5291 1.4506 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8068 0.1853 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 2.4444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5403 1.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0230 -0.4383 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3871 0.9778 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5403 -1.4667 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1628 -0.5952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6936 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8468 -1.4667 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 -2.5403 -0.4889 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 5 2 0 0 0 0 4 13 2 0 0 0 0 5 13 1 0 0 0 0 6 8 1 0 0 0 0 6 15 2 0 0 0 0 7 9 2 0 0 0 0 7 16 1 0 0 0 0 8 17 2 0 0 0 0 9 19 1 0 0 0 0 10 14 2 0 0 0 0 10 15 1 0 0 0 0 11 28 1 0 0 0 0 12 14 1 0 0 0 0 12 38 1 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 15 29 1 0 0 0 0 16 23 1 0 0 0 0 16 30 2 0 0 0 0 17 39 1 0 0 0 0 18 11 1 1 0 0 0 18 20 1 0 0 0 0 18 40 1 0 0 0 0 19 27 1 6 0 0 0 19 31 1 0 0 0 0 20 21 1 0 0 0 0 20 32 1 6 0 0 0 21 22 1 0 0 0 0 21 33 1 1 0 0 0 22 25 1 0 0 0 0 22 41 1 6 0 0 0 23 27 1 6 0 0 0 23 34 1 0 0 0 0 24 35 2 0 0 0 0 24 41 1 0 0 0 0 25 39 1 1 0 0 0 25 40 1 0 0 0 0 26 27 1 0 0 0 0 26 36 2 0 0 0 0 26 38 1 0 0 0 0 27 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	576.15
Volume:	538.021
LogP:	0.869
LogD:	0.192
LogS:	-2.354
# Rotatable Bonds:	10
TPSA:	226.58
# H-Bond Aceptor:	14
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.155
Synthetic Accessibility Score:	4.508
Fsp3:	0.407
Lipinski Rule-of-5:	Rejected
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:	-6.476
MDCK Permeability:	3.820866913883947e-05
Pgp-inhibitor:	0.01
Pgp-substrate:	0.991
Human Intestinal Absorption (HIA):	0.527
20% Bioavailability (F20%):	0.188
30% Bioavailability (F30%):	0.993

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.263
Plasma Protein Binding (PPB):	87.46526336669922%
Volume Distribution (VD):	0.384
Pgp-substrate:	10.04910945892334%

ADMET: Metabolism

CYP1A2-inhibitor:	0.051
CYP1A2-substrate:	0.047
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.061
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.1
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.015
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	2.0
Half-life (T1/2):	0.952

ADMET: Toxicity

hERG Blockers:	0.217
Human Hepatotoxicity (H-HT):	0.206
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.233
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.002
Skin Sensitization:	0.022
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.005

Download Data

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

Natural Product: NPC57072

Natural Product ID:	NPC57072
*Common Name:**	[2-[(2S,3R,4S,5S,6R)-3-Benzoyloxy-4,5-Dihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxy-5-Hydroxyphenyl]Methyl (1R,2R,6R)-1,2,6-Trihydroxy-5-Oxocyclohex-3-Ene-1-Carboxylate
IUPAC Name:	[2-[(2S,3R,4S,5S,6R)-3-benzoyloxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxyphenyl]methyl (1R,2R,6R)-1,2,6-trihydroxy-5-oxocyclohex-3-ene-1-carboxylate
Synonyms:
Standard InCHIKey:	DLBOMVFEFWKKHS-MUZBHQQFSA-N
Standard InCHI:	InChI=1S/C27H28O14/c28-11-18-20(32)21(33)22(41-24(35)13-4-2-1-3-5-13)25(40-18)39-17-8-6-15(29)10-14(17)12-38-26(36)27(37)19(31)9-7-16(30)23(27)34/h1-10,18-23,25,28-29,31-34,37H,11-12H2/t18-,19-,20-,21+,22-,23+,25-,27-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(cc2COC(=O)[C@@]2(O)[C@H](O)C=CC(=O)[C@@H]2O)O)[C@@H]([C@H]([C@@H]1O)O)OC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2316620
PubChem CID:	71575417
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:0004165] Phenolic 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
NPO22355	Flacourtia indica	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23354072]
NPO22355	Flacourtia indica	Species	Salicaceae	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	3
Others	2

Activity Type	# Activity
Cell Line	1
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	CC50	=	77300.0	nM	PMID[543072]
NPT475	Organism	Plasmodium yoelii	Plasmodium yoelii	IC50	>	50000.0	nM	PMID[543072]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	>	5000.0	nM	PMID[543072]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	17.6	n.a.	PMID[543072]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	4400.0	nM	PMID[543072]

☑ 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 NPC57072 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	371
0.1-0.2	1548
0.2-0.3	3805
0.3-0.4	8268
0.4-0.5	9805
0.5-0.6	4739
0.6-0.7	6637
0.7-0.8	6563
0.8-0.85	842
0.85-0.9	89
0.9-0.95	22
0.95-1	8

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC231475
0.9801	High Similarity	NPC474398
0.9801	High Similarity	NPC474441
0.9801	High Similarity	NPC474401
0.9801	High Similarity	NPC476026
0.9677	High Similarity	NPC280923
0.9487	High Similarity	NPC475183
0.9434	High Similarity	NPC280385
0.9404	High Similarity	NPC131874
0.94	High Similarity	NPC22137
0.9367	High Similarity	NPC475174
0.9359	High Similarity	NPC71780
0.9346	High Similarity	NPC230439
0.9346	High Similarity	NPC299761
0.9346	High Similarity	NPC279281
0.9346	High Similarity	NPC92153
0.9333	High Similarity	NPC140722
0.9333	High Similarity	NPC92054
0.9333	High Similarity	NPC4958
0.9281	High Similarity	NPC215811
0.9276	High Similarity	NPC93619
0.9205	High Similarity	NPC83975
0.9198	High Similarity	NPC470438
0.9156	High Similarity	NPC183536
0.9156	High Similarity	NPC34965
0.9139	High Similarity	NPC474422
0.9097	High Similarity	NPC260604
0.9097	High Similarity	NPC299435
0.8994	High Similarity	NPC132737
0.8933	High Similarity	NPC245219
0.8933	High Similarity	NPC31081
0.8933	High Similarity	NPC65833
0.8882	High Similarity	NPC127415
0.8875	High Similarity	NPC217950
0.8854	High Similarity	NPC185103
0.8831	High Similarity	NPC302989
0.8827	High Similarity	NPC178281
0.8805	High Similarity	NPC177742
0.8795	High Similarity	NPC237435
0.8795	High Similarity	NPC115760
0.8795	High Similarity	NPC101191
0.8795	High Similarity	NPC210094
0.8795	High Similarity	NPC43211
0.8795	High Similarity	NPC477848
0.8795	High Similarity	NPC49344
0.8795	High Similarity	NPC264735
0.8795	High Similarity	NPC135277
0.8758	High Similarity	NPC282169
0.8743	High Similarity	NPC198324
0.8743	High Similarity	NPC233994
0.8743	High Similarity	NPC211532
0.8743	High Similarity	NPC472380
0.8743	High Similarity	NPC472384
0.8743	High Similarity	NPC472385
0.8743	High Similarity	NPC268533
0.8743	High Similarity	NPC472382
0.8734	High Similarity	NPC470331
0.8727	High Similarity	NPC235260
0.8727	High Similarity	NPC20505
0.8727	High Similarity	NPC245014
0.8727	High Similarity	NPC84265
0.8727	High Similarity	NPC155763
0.8727	High Similarity	NPC282987
0.8718	High Similarity	NPC471214
0.8704	High Similarity	NPC101116
0.8704	High Similarity	NPC27942
0.8704	High Similarity	NPC212099
0.8704	High Similarity	NPC278329
0.8704	High Similarity	NPC146837
0.8696	High Similarity	NPC328093
0.8688	High Similarity	NPC223335
0.8688	High Similarity	NPC40920
0.8684	High Similarity	NPC145319
0.8675	High Similarity	NPC254540
0.8675	High Similarity	NPC172807
0.8675	High Similarity	NPC117260
0.8675	High Similarity	NPC175107
0.8675	High Similarity	NPC476405
0.8675	High Similarity	NPC211594
0.8675	High Similarity	NPC190003
0.8675	High Similarity	NPC472386
0.8667	High Similarity	NPC246274
0.8667	High Similarity	NPC138927
0.8662	High Similarity	NPC475890
0.865	High Similarity	NPC121703
0.865	High Similarity	NPC80068
0.8647	High Similarity	NPC36138
0.8642	High Similarity	NPC48093
0.8642	High Similarity	NPC129217
0.8642	High Similarity	NPC259957
0.8642	High Similarity	NPC216496
0.8642	High Similarity	NPC224530
0.8642	High Similarity	NPC85707
0.8642	High Similarity	NPC159579
0.8634	High Similarity	NPC469654
0.8634	High Similarity	NPC74319
0.8634	High Similarity	NPC287872
0.8631	High Similarity	NPC144097
0.8631	High Similarity	NPC472991
0.8631	High Similarity	NPC472992
0.8631	High Similarity	NPC61904
0.8627	High Similarity	NPC242756
0.8625	High Similarity	NPC323593
0.8625	High Similarity	NPC261866
0.8625	High Similarity	NPC307938
0.8625	High Similarity	NPC203500
0.8623	High Similarity	NPC45522
0.8623	High Similarity	NPC4390
0.8623	High Similarity	NPC21666
0.8623	High Similarity	NPC42773
0.8623	High Similarity	NPC101026
0.8623	High Similarity	NPC169977
0.8623	High Similarity	NPC24043
0.8614	High Similarity	NPC149011
0.8614	High Similarity	NPC44558
0.8614	High Similarity	NPC105511
0.8614	High Similarity	NPC244776
0.8614	High Similarity	NPC210808
0.8614	High Similarity	NPC199079
0.8614	High Similarity	NPC471416
0.8614	High Similarity	NPC116864
0.8614	High Similarity	NPC34287
0.8614	High Similarity	NPC204937
0.8606	High Similarity	NPC45618
0.8606	High Similarity	NPC146792
0.8606	High Similarity	NPC63470
0.8606	High Similarity	NPC58716
0.8606	High Similarity	NPC116745
0.8599	High Similarity	NPC182350
0.8598	High Similarity	NPC139060
0.8598	High Similarity	NPC85751
0.8598	High Similarity	NPC129264
0.8598	High Similarity	NPC72016
0.8598	High Similarity	NPC19240
0.8598	High Similarity	NPC205824
0.8598	High Similarity	NPC277205
0.8596	High Similarity	NPC470416
0.8589	High Similarity	NPC4013
0.8589	High Similarity	NPC90905
0.8589	High Similarity	NPC61594
0.8589	High Similarity	NPC22324
0.8589	High Similarity	NPC56735
0.8588	High Similarity	NPC222674
0.858	High Similarity	NPC253521
0.858	High Similarity	NPC476619
0.858	High Similarity	NPC35167
0.858	High Similarity	NPC113836
0.858	High Similarity	NPC472387
0.858	High Similarity	NPC37668
0.858	High Similarity	NPC476622
0.858	High Similarity	NPC476621
0.858	High Similarity	NPC44507
0.858	High Similarity	NPC476623
0.858	High Similarity	NPC476620
0.858	High Similarity	NPC476618
0.8571	High Similarity	NPC197896
0.8571	High Similarity	NPC54802
0.8571	High Similarity	NPC108831
0.8571	High Similarity	NPC135391
0.8571	High Similarity	NPC156457
0.8571	High Similarity	NPC223426
0.8571	High Similarity	NPC34267
0.8571	High Similarity	NPC313163
0.8571	High Similarity	NPC161749
0.8571	High Similarity	NPC258035
0.8571	High Similarity	NPC253685
0.8571	High Similarity	NPC78263
0.8571	High Similarity	NPC214621
0.8571	High Similarity	NPC6985
0.8571	High Similarity	NPC182634
0.8571	High Similarity	NPC133671
0.8571	High Similarity	NPC197304
0.8571	High Similarity	NPC60966
0.8571	High Similarity	NPC77672
0.8571	High Similarity	NPC81042
0.8571	High Similarity	NPC43638
0.8563	High Similarity	NPC205076
0.8563	High Similarity	NPC257011
0.8563	High Similarity	NPC137871
0.8563	High Similarity	NPC307518
0.8563	High Similarity	NPC48773
0.8563	High Similarity	NPC153755
0.8563	High Similarity	NPC288152
0.8563	High Similarity	NPC9002
0.8563	High Similarity	NPC315619
0.8562	High Similarity	NPC237560
0.8562	High Similarity	NPC164599
0.8562	High Similarity	NPC10205
0.8554	High Similarity	NPC112755
0.8554	High Similarity	NPC58053
0.8554	High Similarity	NPC105025
0.8554	High Similarity	NPC226294
0.8554	High Similarity	NPC201292
0.8554	High Similarity	NPC472133
0.8554	High Similarity	NPC170675
0.8554	High Similarity	NPC222455
0.8554	High Similarity	NPC475942
0.8554	High Similarity	NPC186807
0.8554	High Similarity	NPC472383
0.8554	High Similarity	NPC93337

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 NPC57072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	324
0.1-0.2	878
0.2-0.3	1863
0.3-0.4	2633
0.4-0.5	1910
0.5-0.6	1024
0.6-0.7	375
0.7-0.8	127
0.8-0.85	14
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8797	High Similarity	NPD5402	Approved
0.8795	High Similarity	NPD4338	Clinical (unspecified phase)
0.8571	High Similarity	NPD4381	Clinical (unspecified phase)
0.8497	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8354	Intermediate Similarity	NPD5403	Approved
0.8343	Intermediate Similarity	NPD6797	Phase 2
0.8304	Intermediate Similarity	NPD8312	Approved
0.8304	Intermediate Similarity	NPD8313	Approved
0.8294	Intermediate Similarity	NPD7251	Discontinued
0.8274	Intermediate Similarity	NPD3818	Discontinued
0.8274	Intermediate Similarity	NPD3751	Discontinued
0.8246	Intermediate Similarity	NPD7808	Phase 3
0.8228	Intermediate Similarity	NPD5401	Approved
0.8225	Intermediate Similarity	NPD7054	Approved
0.8225	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6559	Discontinued
0.8176	Intermediate Similarity	NPD7074	Phase 3
0.8176	Intermediate Similarity	NPD7472	Approved
0.8121	Intermediate Similarity	NPD7075	Discontinued
0.8061	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8033	Intermediate Similarity	NPD7435	Discontinued
0.7975	Intermediate Similarity	NPD4380	Phase 2
0.7967	Intermediate Similarity	NPD6777	Approved
0.7967	Intermediate Similarity	NPD6782	Approved
0.7967	Intermediate Similarity	NPD6776	Approved
0.7967	Intermediate Similarity	NPD6780	Approved
0.7967	Intermediate Similarity	NPD6778	Approved
0.7967	Intermediate Similarity	NPD6781	Approved
0.7967	Intermediate Similarity	NPD6779	Approved
0.7963	Intermediate Similarity	NPD1653	Approved
0.7941	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD6166	Phase 2
0.7939	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7929	Intermediate Similarity	NPD3787	Discontinued
0.7919	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7892	Intermediate Similarity	NPD3817	Phase 2
0.7879	Intermediate Similarity	NPD6801	Discontinued
0.7862	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD2801	Approved
0.7826	Intermediate Similarity	NPD6799	Approved
0.7778	Intermediate Similarity	NPD7874	Approved
0.7778	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1934	Approved
0.7771	Intermediate Similarity	NPD7685	Pre-registration
0.7742	Intermediate Similarity	NPD7697	Approved
0.7742	Intermediate Similarity	NPD7696	Phase 3
0.7742	Intermediate Similarity	NPD7698	Approved
0.7738	Intermediate Similarity	NPD3882	Suspended
0.7725	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD8455	Phase 2
0.7722	Intermediate Similarity	NPD2935	Discontinued
0.7722	Intermediate Similarity	NPD1551	Phase 2
0.7702	Intermediate Similarity	NPD6190	Approved
0.7701	Intermediate Similarity	NPD7870	Phase 2
0.7701	Intermediate Similarity	NPD7871	Phase 2
0.7692	Intermediate Similarity	NPD1933	Approved
0.7692	Intermediate Similarity	NPD6534	Approved
0.7692	Intermediate Similarity	NPD6535	Approved
0.7672	Intermediate Similarity	NPD7701	Phase 2
0.7667	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8150	Discontinued
0.7654	Intermediate Similarity	NPD8434	Phase 2
0.764	Intermediate Similarity	NPD3750	Approved
0.7632	Intermediate Similarity	NPD1203	Approved
0.7625	Intermediate Similarity	NPD1549	Phase 2
0.7622	Intermediate Similarity	NPD1512	Approved
0.7619	Intermediate Similarity	NPD7819	Suspended
0.7605	Intermediate Similarity	NPD7411	Suspended
0.76	Intermediate Similarity	NPD5844	Phase 1
0.76	Intermediate Similarity	NPD1091	Approved
0.7598	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7594	Intermediate Similarity	NPD6823	Phase 2
0.759	Intermediate Similarity	NPD3226	Approved
0.758	Intermediate Similarity	NPD447	Suspended
0.7568	Intermediate Similarity	NPD7700	Phase 2
0.7568	Intermediate Similarity	NPD7699	Phase 2
0.7562	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD7266	Discontinued
0.7562	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD7801	Approved
0.7545	Intermediate Similarity	NPD6599	Discontinued
0.7531	Intermediate Similarity	NPD4628	Phase 3
0.75	Intermediate Similarity	NPD1511	Approved
0.75	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD5494	Approved
0.7485	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6832	Phase 2
0.7468	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD7783	Phase 2
0.7456	Intermediate Similarity	NPD6844	Discontinued
0.7455	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD2346	Discontinued
0.7452	Intermediate Similarity	NPD6233	Phase 2
0.7421	Intermediate Similarity	NPD8320	Phase 1
0.7421	Intermediate Similarity	NPD8319	Approved
0.7412	Intermediate Similarity	NPD1465	Phase 2
0.7387	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7384	Intermediate Similarity	NPD3749	Approved
0.7368	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6212	Phase 3
0.7351	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6213	Phase 3
0.7349	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD7228	Approved
0.733	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD1510	Phase 2
0.7329	Intermediate Similarity	NPD3748	Approved
0.7329	Intermediate Similarity	NPD7033	Discontinued
0.7326	Intermediate Similarity	NPD7768	Phase 2
0.732	Intermediate Similarity	NPD9717	Approved
0.7317	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7314	Intermediate Similarity	NPD6232	Discontinued
0.7288	Intermediate Similarity	NPD7473	Discontinued
0.7284	Intermediate Similarity	NPD2796	Approved
0.7278	Intermediate Similarity	NPD6798	Discontinued
0.7268	Intermediate Similarity	NPD8151	Discontinued
0.7262	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD6959	Discontinued
0.7255	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD37	Approved
0.7241	Intermediate Similarity	NPD6234	Discontinued
0.7226	Intermediate Similarity	NPD3225	Approved
0.7225	Intermediate Similarity	NPD4966	Approved
0.7225	Intermediate Similarity	NPD4965	Approved
0.7225	Intermediate Similarity	NPD4967	Phase 2
0.7222	Intermediate Similarity	NPD2799	Discontinued
0.7222	Intermediate Similarity	NPD4308	Phase 3
0.7186	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD7458	Discontinued
0.7175	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD411	Approved
0.7165	Intermediate Similarity	NPD7584	Approved
0.716	Intermediate Similarity	NPD7097	Phase 1
0.7159	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7135	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2798	Approved
0.7113	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1613	Approved
0.7081	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD1240	Approved
0.707	Intermediate Similarity	NPD2797	Approved
0.7063	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD3268	Approved
0.7053	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7585	Approved
0.7037	Intermediate Similarity	NPD230	Phase 1
0.7033	Intermediate Similarity	NPD5953	Discontinued
0.703	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1019	Discontinued
0.6995	Remote Similarity	NPD7240	Approved
0.6994	Remote Similarity	NPD1607	Approved
0.699	Remote Similarity	NPD7583	Approved
0.6983	Remote Similarity	NPD3926	Phase 2
0.6981	Remote Similarity	NPD2861	Phase 2
0.6975	Remote Similarity	NPD4060	Phase 1
0.6975	Remote Similarity	NPD4307	Phase 2
0.6974	Remote Similarity	NPD9493	Approved
0.6968	Remote Similarity	NPD3496	Discontinued
0.6966	Remote Similarity	NPD1247	Approved
0.6957	Remote Similarity	NPD3764	Approved
0.6951	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD919	Approved
0.6941	Remote Similarity	NPD2532	Approved
0.6941	Remote Similarity	NPD2533	Approved
0.6941	Remote Similarity	NPD2534	Approved
0.6928	Remote Similarity	NPD2344	Approved
0.6918	Remote Similarity	NPD5647	Approved
0.6914	Remote Similarity	NPD4062	Phase 3
0.6901	Remote Similarity	NPD5049	Phase 3
0.6901	Remote Similarity	NPD6273	Approved
0.6894	Remote Similarity	NPD7095	Approved
0.6886	Remote Similarity	NPD2424	Discontinued
0.6879	Remote Similarity	NPD1481	Phase 2
0.6879	Remote Similarity	NPD1608	Approved
0.6875	Remote Similarity	NPD8059	Phase 3
0.6875	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6868	Remote Similarity	NPD7799	Discontinued
0.6867	Remote Similarity	NPD6032	Approved
0.6867	Remote Similarity	NPD6099	Approved
0.6867	Remote Similarity	NPD6100	Approved
0.6864	Remote Similarity	NPD2354	Approved
0.6864	Remote Similarity	NPD3887	Approved
0.686	Remote Similarity	NPD920	Approved
0.6855	Remote Similarity	NPD1470	Approved
0.6854	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8404	Phase 2
0.6845	Remote Similarity	NPD1652	Phase 2
0.6842	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4662	Approved
0.6842	Remote Similarity	NPD4661	Approved
0.6832	Remote Similarity	NPD7930	Approved
0.6832	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD8470	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