NPASS Compound

Structure

NPC473741 OpenBabel07101718292D 47 47 0 0 1 0 0 0 0 0999 V2000 -3.2409 -5.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7169 3.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0765 -3.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2105 -5.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5088 0.7340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7169 -6.5851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 -6.5851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2105 0.7340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0765 -0.7660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9848 2.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9696 -2.8794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3445 -5.1775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1777 1.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2409 -4.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7169 2.1736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3748 -3.6454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5088 -4.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2105 -4.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5088 -0.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 -6.0851 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2105 -0.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8508 1.6736 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.6428 -3.6454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3445 -3.6454 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8508 0.6736 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6428 -0.7660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8508 -5.0851 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3445 -0.7660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9848 -1.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 -4.9115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7017 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.4115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6865 -2.7057 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9848 -2.7057 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.7017 -4.4115 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.8356 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9696 -1.5321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1777 -5.8512 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3445 0.7660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6428 -5.1775 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6713 -2.8794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5240 1.4397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.9115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6865 -1.7057 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 15 1 0 0 0 0 2 16 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 20 1 0 0 0 0 6 20 1 0 0 0 0 7 21 1 0 0 0 0 8 21 1 0 0 0 0 9 22 1 0 0 0 0 10 22 1 0 0 0 0 11 23 1 0 0 0 0 12 36 1 0 0 0 0 13 37 1 0 0 0 0 14 38 1 0 0 0 0 15 17 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 24 18 1 6 0 0 0 24 33 1 0 0 0 0 24 36 1 0 0 0 0 25 19 1 6 0 0 0 25 34 1 0 0 0 0 25 37 1 0 0 0 0 26 23 1 6 0 0 0 26 35 1 0 0 0 0 26 38 1 0 0 0 0 27 20 1 1 0 0 0 27 30 1 0 0 0 0 27 47 1 0 0 0 0 28 21 1 1 0 0 0 28 31 1 0 0 0 0 28 45 1 0 0 0 0 29 22 1 1 0 0 0 29 32 1 0 0 0 0 29 46 1 0 0 0 0 30 36 1 0 0 0 0 30 39 2 0 0 0 0 31 37 1 0 0 0 0 31 40 2 0 0 0 0 32 38 1 0 0 0 0 32 41 2 0 0 0 0 33 42 2 0 0 0 0 33 45 1 0 0 0 0 34 43 2 0 0 0 0 34 46 1 0 0 0 0 35 44 2 0 0 0 0 35 47 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	667.44
Volume:	701.643
LogP:	4.451
LogD:	2.715
LogS:	-4.148
# Rotatable Bonds:	9
TPSA:	139.83
# H-Bond Aceptor:	12
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	5.389
Fsp3:	0.829
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:	-5.106
MDCK Permeability:	2.909398972406052e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.029
Human Intestinal Absorption (HIA):	0.805
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.457

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	92.90341186523438%
Volume Distribution (VD):	1.28
Pgp-substrate:	2.3829753398895264%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.072
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.939
CYP2C9-inhibitor:	0.099
CYP2C9-substrate:	0.067
CYP2D6-inhibitor:	0.068
CYP2D6-substrate:	0.083
CYP3A4-inhibitor:	0.554
CYP3A4-substrate:	0.914

ADMET: Excretion

Clearance (CL):	5.661
Half-life (T1/2):	0.044

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.987
Drug-inuced Liver Injury (DILI):	0.985
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.011
Skin Sensitization:	0.023
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.008

Download Data

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

Natural Product: NPC473741

Natural Product ID:	NPC473741
*Common Name:**	Enniatin A1
IUPAC Name:	(3S,6R,9S,12R,15S,18R)-3-butan-2-yl-15-butyl-4,10,16-trimethyl-6,9,12,18-tetra(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
Synonyms:	Enniatin A1
Standard InCHIKey:	VGOLHAPJYMAXRH-CKHUAROESA-N
Standard InCHI:	InChI=1S/C35H61N3O9/c1-15-17-18-24-33(42)45-28(21(7)8)31(40)37(13)25(19(3)4)34(43)46-29(22(9)10)32(41)38(14)26(23(11)16-2)35(44)47-27(20(5)6)30(39)36(24)12/h19-29H,15-18H2,1-14H3/t23?,24-,25-,26-,27+,28+,29+/m0/s1
SMILES:	CCCC[C@H]1C(=O)O[C@H](C(C)C)C(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N1C)C(C)C)C(CC)C)C)C(C)C
Synthetic Gene Cluster:	BGC0000342;
ChEMBL Identifier:	CHEMBL450707
PubChem CID:	16727692
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562855]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17286429]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21090694]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175613]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9014349]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25042	Fusarium tricinctum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29266	Fusarium oxysporum	Species	Nectriaceae	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
MIC	10

Activity Type	# Activity
Organism	13

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	2.0	ug.mL-1	PMID[517900]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	6.25	ug.mL-1	PMID[517900]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	=	4.5	ug.mL-1	PMID[517900]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	12.5	ug.mL-1	PMID[517900]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	IC50	=	9.0	ug.mL-1	PMID[517900]
NPT86	Organism	Mycobacterium intracellulare	Mycobacterium intracellulare	MIC	=	50.0	ug.mL-1	PMID[517900]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	64.0	ug.mL-1	PMID[517901]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	64.0	ug.mL-1	PMID[517901]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	4.0	ug.mL-1	PMID[517901]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	2.0	ug.mL-1	PMID[517901]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[517901]
NPT2709	Organism	Bacillus subtilis subsp. subtilis str. 168	Bacillus subtilis subsp. subtilis str. 168	MIC	=	8.0	ug.mL-1	PMID[517901]

☑ 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 NPC473741 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	223
0.1-0.2	12286
0.2-0.3	20240
0.3-0.4	8367
0.4-0.5	1192
0.5-0.6	314
0.6-0.7	49
0.7-0.8	19
0.8-0.85	0
0.85-0.9	3
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477145
0.9437	High Similarity	NPC178919
0.9167	High Similarity	NPC263281
0.8873	High Similarity	NPC29598
0.8873	High Similarity	NPC212866
0.8732	High Similarity	NPC10716
0.7614	Intermediate Similarity	NPC476019
0.7609	Intermediate Similarity	NPC220234
0.759	Intermediate Similarity	NPC246005
0.7368	Intermediate Similarity	NPC5864
0.7368	Intermediate Similarity	NPC301148
0.7368	Intermediate Similarity	NPC124554
0.7333	Intermediate Similarity	NPC173763
0.7333	Intermediate Similarity	NPC62263
0.7333	Intermediate Similarity	NPC471098
0.7222	Intermediate Similarity	NPC474576
0.7216	Intermediate Similarity	NPC124549
0.7216	Intermediate Similarity	NPC323720
0.7191	Intermediate Similarity	NPC322966
0.7113	Intermediate Similarity	NPC198344
0.7111	Intermediate Similarity	NPC474593
0.7111	Intermediate Similarity	NPC475801
0.7	Intermediate Similarity	NPC171734
0.7	Intermediate Similarity	NPC67009
0.6875	Remote Similarity	NPC475440
0.6667	Remote Similarity	NPC471097
0.6667	Remote Similarity	NPC475149
0.6634	Remote Similarity	NPC475637
0.6591	Remote Similarity	NPC53858
0.6591	Remote Similarity	NPC84128
0.6465	Remote Similarity	NPC13175
0.6465	Remote Similarity	NPC475791
0.6463	Remote Similarity	NPC478256
0.6421	Remote Similarity	NPC315237
0.6375	Remote Similarity	NPC325117
0.6375	Remote Similarity	NPC322319
0.6375	Remote Similarity	NPC326651
0.6364	Remote Similarity	NPC475758
0.625	Remote Similarity	NPC477238
0.6235	Remote Similarity	NPC208657
0.6163	Remote Similarity	NPC86064
0.6162	Remote Similarity	NPC473597
0.6146	Remote Similarity	NPC477538
0.6136	Remote Similarity	NPC233108
0.6118	Remote Similarity	NPC141325
0.6087	Remote Similarity	NPC472351
0.6078	Remote Similarity	NPC188785
0.6071	Remote Similarity	NPC477237
0.6055	Remote Similarity	NPC471202
0.6055	Remote Similarity	NPC63191
0.6049	Remote Similarity	NPC472609
0.6047	Remote Similarity	NPC138435
0.6047	Remote Similarity	NPC43219
0.6	Remote Similarity	NPC103391
0.6	Remote Similarity	NPC476243
0.6	Remote Similarity	NPC47076
0.6	Remote Similarity	NPC134504
0.6	Remote Similarity	NPC476156
0.6	Remote Similarity	NPC476117
0.6	Remote Similarity	NPC216090
0.6	Remote Similarity	NPC472536
0.6	Remote Similarity	NPC476137
0.5978	Remote Similarity	NPC235078
0.5977	Remote Similarity	NPC327272
0.5966	Remote Similarity	NPC239990
0.5966	Remote Similarity	NPC105114
0.5966	Remote Similarity	NPC89923
0.5966	Remote Similarity	NPC71933
0.5966	Remote Similarity	NPC152850
0.5952	Remote Similarity	NPC320663
0.5952	Remote Similarity	NPC224700
0.5934	Remote Similarity	NPC23984
0.5934	Remote Similarity	NPC476302
0.5914	Remote Similarity	NPC155670
0.5914	Remote Similarity	NPC95478
0.5914	Remote Similarity	NPC145748
0.5909	Remote Similarity	NPC476130
0.5909	Remote Similarity	NPC476324
0.5889	Remote Similarity	NPC31756
0.5882	Remote Similarity	NPC476291
0.5882	Remote Similarity	NPC136453
0.5851	Remote Similarity	NPC227051
0.5842	Remote Similarity	NPC471843
0.5833	Remote Similarity	NPC52533
0.582	Remote Similarity	NPC157311
0.5806	Remote Similarity	NPC47135
0.5772	Remote Similarity	NPC8761
0.5772	Remote Similarity	NPC44805
0.5769	Remote Similarity	NPC278209
0.5766	Remote Similarity	NPC469597
0.5765	Remote Similarity	NPC193280
0.5765	Remote Similarity	NPC314273
0.5763	Remote Similarity	NPC309525
0.5727	Remote Similarity	NPC476875
0.5714	Remote Similarity	NPC477729
0.5714	Remote Similarity	NPC178632
0.5714	Remote Similarity	NPC315535
0.5714	Remote Similarity	NPC478017
0.5714	Remote Similarity	NPC315131
0.5701	Remote Similarity	NPC241394
0.5698	Remote Similarity	NPC476285
0.5691	Remote Similarity	NPC120420
0.5682	Remote Similarity	NPC476248
0.5658	Remote Similarity	NPC325180
0.5658	Remote Similarity	NPC35816
0.5657	Remote Similarity	NPC47230
0.5657	Remote Similarity	NPC17143
0.5652	Remote Similarity	NPC474702
0.5648	Remote Similarity	NPC137453
0.5645	Remote Similarity	NPC99864
0.5625	Remote Similarity	NPC319991
0.5607	Remote Similarity	NPC128303
0.5607	Remote Similarity	NPC205176
0.5604	Remote Similarity	NPC316242

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 NPC473741 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	127
0.1-0.2	2802
0.2-0.3	4361
0.3-0.4	1387
0.4-0.5	369
0.5-0.6	92
0.6-0.7	11
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8873	High Similarity	NPD7840	Approved
0.6706	Remote Similarity	NPD8143	Approved
0.6706	Remote Similarity	NPD8144	Approved
0.6667	Remote Similarity	NPD2696	Approved
0.6667	Remote Similarity	NPD2697	Approved
0.6667	Remote Similarity	NPD2695	Approved
0.6667	Remote Similarity	NPD2694	Approved
0.6598	Remote Similarity	NPD3715	Approved
0.6598	Remote Similarity	NPD3713	Approved
0.6598	Remote Similarity	NPD3714	Approved
0.6506	Remote Similarity	NPD6704	Discontinued
0.6486	Remote Similarity	NPD4281	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD2220	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD4780	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3726	Approved
0.6071	Remote Similarity	NPD3725	Approved
0.6019	Remote Similarity	NPD8300	Approved
0.6019	Remote Similarity	NPD8301	Approved
0.6	Remote Similarity	NPD7535	Discontinued
0.5979	Remote Similarity	NPD2682	Approved
0.5957	Remote Similarity	NPD7760	Phase 2
0.5957	Remote Similarity	NPD7759	Phase 2
0.5952	Remote Similarity	NPD3724	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD8278	Approved
0.5909	Remote Similarity	NPD11	Approved
0.5909	Remote Similarity	NPD376	Approved
0.59	Remote Similarity	NPD7841	Clinical (unspecified phase)
0.5882	Remote Similarity	NPD8277	Approved
0.5816	Remote Similarity	NPD4261	Phase 1
0.5806	Remote Similarity	NPD7345	Approved
0.5789	Remote Similarity	NPD3723	Clinical (unspecified phase)
0.5784	Remote Similarity	NPD8038	Phase 2
0.5765	Remote Similarity	NPD620	Approved
0.5761	Remote Similarity	NPD612	Discontinued
0.5761	Remote Similarity	NPD7763	Phase 2
0.5761	Remote Similarity	NPD7762	Phase 2
0.5758	Remote Similarity	NPD6699	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7917	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7918	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD9649	Approved
0.5682	Remote Similarity	NPD355	Phase 2
0.5663	Remote Similarity	NPD9648	Approved
0.5663	Remote Similarity	NPD4272	Discontinued
0.5658	Remote Similarity	NPD9660	Approved
0.5648	Remote Similarity	NPD8140	Approved
0.5645	Remote Similarity	NPD8415	Approved
0.5604	Remote Similarity	NPD3160	Suspended
0.56	Remote Similarity	NPD8387	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