NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	800.18
Volume:	688.6
LogP:	2.996
LogD:	1.377
LogS:	-3.647
# Rotatable Bonds:	17
TPSA:	247.75
# H-Bond Aceptor:	14
# H-Bond Donor:	13
# Rings:	5
# Heavy Atoms:	16

MedChem Properties

QED Drug-Likeness Score:	0.048
Synthetic Accessibility Score:	4.587
Fsp3:	0.394
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:	-5.568
MDCK Permeability:	6.026988103258191e-06
Pgp-inhibitor:	0.126
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.215
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.012

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.7
Plasma Protein Binding (PPB):	90.84790802001953%
Volume Distribution (VD):	1.461
Pgp-substrate:	17.940183639526367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.089
CYP1A2-substrate:	0.557
CYP2C19-inhibitor:	0.116
CYP2C19-substrate:	0.051
CYP2C9-inhibitor:	0.011
CYP2C9-substrate:	0.016
CYP2D6-inhibitor:	0.882
CYP2D6-substrate:	0.663
CYP3A4-inhibitor:	0.341
CYP3A4-substrate:	0.076

ADMET: Excretion

Clearance (CL):	3.828
Half-life (T1/2):	0.289

ADMET: Toxicity

hERG Blockers:	0.285
Human Hepatotoxicity (H-HT):	0.08
Drug-inuced Liver Injury (DILI):	0.874
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.984
Maximum Recommended Daily Dose:	0.973
Skin Sensitization:	0.168
Carcinogencity:	0.076
Eye Corrosion:	0.003
Eye Irritation:	0.003
Respiratory Toxicity:	0.05

Download Data

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

Natural Product: NPC477107

Natural Product ID:	NPC477107
*Common Name:**	Eusynstyelamide A
IUPAC Name:	(2R,3R,4S)-3,4-bis[(6-bromo-1H-indol-3-yl)methyl]-N,1-bis[4-(diaminomethylideneamino)butyl]-2,4-dihydroxy-5-oxopyrrolidine-2-carboxamide
Synonyms:
Standard InCHIKey:	FWIZAEZOEFOBCD-UKOABYEESA-N
Standard InCHI:	InChI=1S/C33H42Br2N10O4/c34-21-5-7-23-19(17-43-25(23)14-21)13-27-32(48,16-20-18-44-26-15-22(35)6-8-24(20)26)29(47)45(12-4-3-11-42-31(38)39)33(27,49)28(46)40-9-1-2-10-41-30(36)37/h5-8,14-15,17-18,27,43-44,48-49H,1-4,9-13,16H2,(H,40,46)(H4,36,37,41)(H4,38,39,42)/t27-,32+,33-/m1/s1
SMILES:	C1=CC2=C(C=C1Br)NC=C2C[C@@H]3[C@](C(=O)N([C@@]3(C(=O)NCCCCN=C(N)N)O)CCCCN=C(N)N)(CC4=CNC5=C4C=CC(=C5)Br)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	70685495
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000347] Amino acids and derivatives [CHEMONTID:0000060] Alpha amino acids and derivatives [CHEMONTID:0002309] Alpha amino acid amides

*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
NPO11682	Eusynstyela latericius	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19505081]
NPO11682	Eusynstyela latericius	Species	Styelidae	Eukaryota	n.a.	Hixson Island (2145.0' S, 15017.5' E); Percy Island Group in the Central Great Barrier Reef, Queensland, Australia; Rib Reef (1828.7' S, 14652.3' E)	n.a.	PMID[19505081]
NPO11682	Eusynstyela latericius	Species	Styelidae	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

Activity Type	# Activity
Individual Protein	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT269	Individual Protein	Nitric-oxide synthase, brain	Rattus norvegicus	IC50	=	41700	nM	PMID[19505081]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	IC50	=	19000	nM	PMID[19505081]
NPT2	Others	Unspecified		IC50	=	19000000	nM	PMID[19505081]

☑ 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 NPC477107 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	506
0.1-0.2	3359
0.2-0.3	18129
0.3-0.4	14267
0.4-0.5	2632
0.5-0.6	2643
0.6-0.7	978
0.7-0.8	173
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC477108
1.0	High Similarity	NPC477109
0.9953	High Similarity	NPC17487
0.9953	High Similarity	NPC201831
0.9579	High Similarity	NPC63031
0.8796	High Similarity	NPC477114
0.8416	Intermediate Similarity	NPC475736
0.8178	Intermediate Similarity	NPC474195
0.8114	Intermediate Similarity	NPC474196
0.7871	Intermediate Similarity	NPC125181
0.7871	Intermediate Similarity	NPC263117
0.7871	Intermediate Similarity	NPC242872
0.7812	Intermediate Similarity	NPC162860
0.7803	Intermediate Similarity	NPC54420
0.7795	Intermediate Similarity	NPC321939
0.7793	Intermediate Similarity	NPC473376
0.7755	Intermediate Similarity	NPC471536
0.7743	Intermediate Similarity	NPC320968
0.7738	Intermediate Similarity	NPC52909
0.7738	Intermediate Similarity	NPC94211
0.7738	Intermediate Similarity	NPC475935
0.7708	Intermediate Similarity	NPC117980
0.7696	Intermediate Similarity	NPC477167
0.7696	Intermediate Similarity	NPC473342
0.7692	Intermediate Similarity	NPC205254
0.7692	Intermediate Similarity	NPC303820
0.7692	Intermediate Similarity	NPC106771
0.7692	Intermediate Similarity	NPC23420
0.7682	Intermediate Similarity	NPC171317
0.7675	Intermediate Similarity	NPC54744
0.7669	Intermediate Similarity	NPC69843
0.7632	Intermediate Similarity	NPC207020
0.7607	Intermediate Similarity	NPC64216
0.7565	Intermediate Similarity	NPC478157
0.756	Intermediate Similarity	NPC475746
0.7555	Intermediate Similarity	NPC75634
0.7553	Intermediate Similarity	NPC156003
0.7545	Intermediate Similarity	NPC476073
0.7543	Intermediate Similarity	NPC477714
0.7542	Intermediate Similarity	NPC325976
0.7534	Intermediate Similarity	NPC166209
0.7534	Intermediate Similarity	NPC77241
0.7534	Intermediate Similarity	NPC269203
0.7534	Intermediate Similarity	NPC13456
0.7531	Intermediate Similarity	NPC89987
0.7523	Intermediate Similarity	NPC474389
0.75	Intermediate Similarity	NPC477715
0.75	Intermediate Similarity	NPC478158
0.7489	Intermediate Similarity	NPC220797
0.7489	Intermediate Similarity	NPC474318
0.7489	Intermediate Similarity	NPC201266
0.7489	Intermediate Similarity	NPC268744
0.7489	Intermediate Similarity	NPC475914
0.7489	Intermediate Similarity	NPC153123
0.7455	Intermediate Similarity	NPC304187
0.7455	Intermediate Similarity	NPC477166
0.7444	Intermediate Similarity	NPC131887
0.7424	Intermediate Similarity	NPC223791
0.7424	Intermediate Similarity	NPC107077
0.7417	Intermediate Similarity	NPC475969
0.7417	Intermediate Similarity	NPC475859
0.7417	Intermediate Similarity	NPC474877
0.7411	Intermediate Similarity	NPC293917
0.7399	Intermediate Similarity	NPC227582
0.7397	Intermediate Similarity	NPC213629
0.7397	Intermediate Similarity	NPC321708
0.7389	Intermediate Similarity	NPC155143
0.7378	Intermediate Similarity	NPC252338
0.7375	Intermediate Similarity	NPC470729
0.7375	Intermediate Similarity	NPC477175
0.7375	Intermediate Similarity	NPC477176
0.7375	Intermediate Similarity	NPC326363
0.7375	Intermediate Similarity	NPC470730
0.7371	Intermediate Similarity	NPC477610
0.7355	Intermediate Similarity	NPC63279
0.7345	Intermediate Similarity	NPC475506
0.7344	Intermediate Similarity	NPC477177
0.7342	Intermediate Similarity	NPC88315
0.7325	Intermediate Similarity	NPC297642
0.7319	Intermediate Similarity	NPC281049
0.7314	Intermediate Similarity	NPC165743
0.7289	Intermediate Similarity	NPC473640
0.7284	Intermediate Similarity	NPC82370
0.728	Intermediate Similarity	NPC476818
0.7273	Intermediate Similarity	NPC17059
0.7261	Intermediate Similarity	NPC477608
0.7261	Intermediate Similarity	NPC477607
0.7257	Intermediate Similarity	NPC100321
0.7255	Intermediate Similarity	NPC478006
0.7254	Intermediate Similarity	NPC245055
0.7244	Intermediate Similarity	NPC262898
0.7237	Intermediate Similarity	NPC193761
0.7233	Intermediate Similarity	NPC314882
0.7227	Intermediate Similarity	NPC94752
0.7224	Intermediate Similarity	NPC478028
0.7222	Intermediate Similarity	NPC470703
0.7222	Intermediate Similarity	NPC14812
0.7203	Intermediate Similarity	NPC472285
0.72	Intermediate Similarity	NPC179701
0.7194	Intermediate Similarity	NPC153400
0.7191	Intermediate Similarity	NPC474412
0.719	Intermediate Similarity	NPC191382
0.719	Intermediate Similarity	NPC56109
0.7188	Intermediate Similarity	NPC474180
0.7188	Intermediate Similarity	NPC188821
0.7181	Intermediate Similarity	NPC74413
0.7179	Intermediate Similarity	NPC470702
0.7179	Intermediate Similarity	NPC31385
0.7179	Intermediate Similarity	NPC473218
0.7179	Intermediate Similarity	NPC110602
0.7179	Intermediate Similarity	NPC75726
0.7173	Intermediate Similarity	NPC477609
0.7166	Intermediate Similarity	NPC478029
0.7163	Intermediate Similarity	NPC477611
0.7162	Intermediate Similarity	NPC476874
0.7162	Intermediate Similarity	NPC260900
0.7155	Intermediate Similarity	NPC473317
0.7155	Intermediate Similarity	NPC314957
0.7155	Intermediate Similarity	NPC474896
0.7149	Intermediate Similarity	NPC315555
0.7131	Intermediate Similarity	NPC238945
0.7126	Intermediate Similarity	NPC28945
0.7125	Intermediate Similarity	NPC155444
0.7125	Intermediate Similarity	NPC31097
0.7121	Intermediate Similarity	NPC77101
0.7113	Intermediate Similarity	NPC272174
0.7105	Intermediate Similarity	NPC477004
0.7104	Intermediate Similarity	NPC15102
0.7101	Intermediate Similarity	NPC264285
0.7098	Intermediate Similarity	NPC243716
0.7088	Intermediate Similarity	NPC315467
0.7083	Intermediate Similarity	NPC314603
0.7082	Intermediate Similarity	NPC476524
0.7078	Intermediate Similarity	NPC476491
0.7074	Intermediate Similarity	NPC470497
0.7073	Intermediate Similarity	NPC474357
0.7073	Intermediate Similarity	NPC323752
0.7066	Intermediate Similarity	NPC125597
0.7064	Intermediate Similarity	NPC72956
0.7064	Intermediate Similarity	NPC59269
0.7061	Intermediate Similarity	NPC478009
0.7061	Intermediate Similarity	NPC470499
0.7061	Intermediate Similarity	NPC67288
0.7061	Intermediate Similarity	NPC478010
0.7059	Intermediate Similarity	NPC228835
0.7054	Intermediate Similarity	NPC16352
0.705	Intermediate Similarity	NPC314056
0.7047	Intermediate Similarity	NPC477630
0.7047	Intermediate Similarity	NPC477635
0.7037	Intermediate Similarity	NPC214142
0.7037	Intermediate Similarity	NPC319232
0.7037	Intermediate Similarity	NPC24370
0.7034	Intermediate Similarity	NPC153980
0.7034	Intermediate Similarity	NPC128084
0.7034	Intermediate Similarity	NPC6865
0.7033	Intermediate Similarity	NPC935
0.7033	Intermediate Similarity	NPC267078
0.702	Intermediate Similarity	NPC322135
0.702	Intermediate Similarity	NPC95240
0.7017	Intermediate Similarity	NPC36405
0.7017	Intermediate Similarity	NPC471192
0.7011	Intermediate Similarity	NPC477633
0.7008	Intermediate Similarity	NPC304307
0.7008	Intermediate Similarity	NPC118559
0.7008	Intermediate Similarity	NPC261251
0.7008	Intermediate Similarity	NPC34580
0.7008	Intermediate Similarity	NPC66642
0.7008	Intermediate Similarity	NPC124920
0.7004	Intermediate Similarity	NPC220852
0.7004	Intermediate Similarity	NPC284888
0.7004	Intermediate Similarity	NPC229348
0.7004	Intermediate Similarity	NPC282247
0.6996	Remote Similarity	NPC235684
0.6996	Remote Similarity	NPC141428
0.6988	Remote Similarity	NPC285343
0.6986	Remote Similarity	NPC111275
0.698	Remote Similarity	NPC100547
0.6976	Remote Similarity	NPC33064
0.697	Remote Similarity	NPC478013
0.6968	Remote Similarity	NPC307191
0.6964	Remote Similarity	NPC54803
0.6964	Remote Similarity	NPC321592
0.6962	Remote Similarity	NPC471194
0.6962	Remote Similarity	NPC471193
0.696	Remote Similarity	NPC82472
0.6958	Remote Similarity	NPC469717
0.6958	Remote Similarity	NPC473310
0.6955	Remote Similarity	NPC283219
0.6955	Remote Similarity	NPC55772
0.6951	Remote Similarity	NPC308931
0.6951	Remote Similarity	NPC223409
0.6951	Remote Similarity	NPC99939
0.6947	Remote Similarity	NPC473763
0.6947	Remote Similarity	NPC117244
0.6946	Remote Similarity	NPC203614
0.6946	Remote Similarity	NPC204491
0.6946	Remote Similarity	NPC470731
0.6946	Remote Similarity	NPC470732
0.694	Remote Similarity	NPC473761
0.6935	Remote Similarity	NPC70155

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 NPC477107 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	243
0.1-0.2	593
0.2-0.3	1136
0.3-0.4	2424
0.4-0.5	2514
0.5-0.6	1895
0.6-0.7	317
0.7-0.8	28
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
0.7964	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD7970	Approved
0.7634	Intermediate Similarity	NPD5426	Phase 3
0.75	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7359	Intermediate Similarity	NPD7470	Discontinued
0.7296	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7950	Approved
0.7284	Intermediate Similarity	NPD7953	Approved
0.7284	Intermediate Similarity	NPD7952	Approved
0.7284	Intermediate Similarity	NPD7790	Approved
0.7284	Intermediate Similarity	NPD7951	Approved
0.7284	Intermediate Similarity	NPD7789	Approved
0.7284	Intermediate Similarity	NPD7791	Approved
0.7253	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.722	Intermediate Similarity	NPD7730	Approved
0.722	Intermediate Similarity	NPD7731	Approved
0.719	Intermediate Similarity	NPD7780	Approved
0.719	Intermediate Similarity	NPD7781	Approved
0.7178	Intermediate Similarity	NPD7711	Discontinued
0.716	Intermediate Similarity	NPD7824	Approved
0.7149	Intermediate Similarity	NPD8094	Discontinued
0.7143	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7001	Phase 3
0.7137	Intermediate Similarity	NPD7271	Approved
0.7136	Intermediate Similarity	NPD2096	Phase 2
0.7136	Intermediate Similarity	NPD2091	Phase 2
0.7105	Intermediate Similarity	NPD6999	Discontinued
0.7105	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD7716	Approved
0.7095	Intermediate Similarity	NPD7717	Approved
0.7094	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD2094	Phase 2
0.7091	Intermediate Similarity	NPD2092	Phase 2
0.7091	Intermediate Similarity	NPD2095	Phase 2
0.7078	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD6595	Phase 3
0.7039	Intermediate Similarity	NPD8322	Phase 2
0.7037	Intermediate Similarity	NPD7603	Discontinued
0.7034	Intermediate Similarity	NPD8093	Discontinued
0.7026	Intermediate Similarity	NPD8272	Phase 2
0.7014	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD6165	Phase 2
0.7008	Intermediate Similarity	NPD6164	Phase 2
0.7004	Intermediate Similarity	NPD7944	Discontinued
0.6975	Remote Similarity	NPD8112	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7818	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8073	Approved
0.6933	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD482	Approved
0.6875	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.687	Remote Similarity	NPD6664	Approved
0.6864	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD7665	Phase 2
0.6864	Remote Similarity	NPD7666	Phase 3
0.6846	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD8256	Approved
0.6846	Remote Similarity	NPD8257	Approved
0.6838	Remote Similarity	NPD8072	Approved
0.6835	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD8431	Approved
0.6802	Remote Similarity	NPD8386	Phase 2
0.6783	Remote Similarity	NPD7619	Phase 3
0.6783	Remote Similarity	NPD7618	Phase 3
0.678	Remote Similarity	NPD7957	Phase 1
0.678	Remote Similarity	NPD7958	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6665	Discontinued
0.6757	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.675	Remote Similarity	NPD4852	Phase 2
0.6737	Remote Similarity	NPD7712	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD5901	Discontinued
0.6736	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7948	Phase 1
0.6724	Remote Similarity	NPD2880	Discontinued
0.6697	Remote Similarity	NPD750	Phase 2
0.6695	Remote Similarity	NPD4520	Approved
0.6693	Remote Similarity	NPD8119	Discontinued
0.6681	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8098	Approved
0.6667	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD6458	Discontinued
0.6652	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD8271	Discontinued
0.6639	Remote Similarity	NPD8000	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD8410	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8349	Phase 1
0.6601	Remote Similarity	NPD7415	Suspended
0.6598	Remote Similarity	NPD8321	Discontinued
0.6597	Remote Similarity	NPD8169	Discontinued
0.6594	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6583	Remote Similarity	NPD2442	Approved
0.6583	Remote Similarity	NPD2443	Approved
0.6581	Remote Similarity	NPD5003	Discontinued
0.6577	Remote Similarity	NPD8250	Phase 2
0.6569	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD484	Approved
0.6543	Remote Similarity	NPD2411	Approved
0.6543	Remote Similarity	NPD8097	Phase 3
0.6543	Remote Similarity	NPD8284	Discontinued
0.6543	Remote Similarity	NPD8096	Phase 3
0.654	Remote Similarity	NPD7817	Phase 1
0.653	Remote Similarity	NPD8026	Phase 1
0.6522	Remote Similarity	NPD8372	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD8316	Phase 2
0.6522	Remote Similarity	NPD8106	Phase 2
0.6522	Remote Similarity	NPD8317	Phase 2
0.6518	Remote Similarity	NPD5065	Approved
0.6504	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD2813	Phase 3
0.6502	Remote Similarity	NPD3915	Approved
0.65	Remote Similarity	NPD2008	Discontinued
0.6496	Remote Similarity	NPD8641	Approved
0.6494	Remote Similarity	NPD8289	Discontinued
0.6475	Remote Similarity	NPD3918	Approved
0.6475	Remote Similarity	NPD3917	Approved
0.6475	Remote Similarity	NPD3916	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8047	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD8292	Phase 2
0.6458	Remote Similarity	NPD6987	Phase 1
0.6458	Remote Similarity	NPD56	Approved
0.6458	Remote Similarity	NPD8283	Approved
0.6458	Remote Similarity	NPD8282	Approved
0.6453	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.645	Remote Similarity	NPD2009	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD2509	Approved
0.6446	Remote Similarity	NPD2510	Approved
0.6446	Remote Similarity	NPD7947	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD5721	Clinical (unspecified phase)
0.644	Remote Similarity	NPD6995	Phase 1
0.6437	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD7393	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD4427	Phase 2
0.642	Remote Similarity	NPD2408	Discontinued
0.6417	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6407	Remote Similarity	NPD706	Phase 1
0.6406	Remote Similarity	NPD5040	Clinical (unspecified phase)
0.6394	Remote Similarity	NPD6531	Approved
0.6394	Remote Similarity	NPD6530	Approved
0.6393	Remote Similarity	NPD3014	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD7465	Suspended
0.6393	Remote Similarity	NPD3013	Phase 3
0.6392	Remote Similarity	NPD7688	Phase 1
0.6381	Remote Similarity	NPD6970	Phase 2
0.6376	Remote Similarity	NPD8408	Discontinued
0.6376	Remote Similarity	NPD8524	Approved
0.6371	Remote Similarity	NPD5818	Discontinued
0.636	Remote Similarity	NPD4076	Approved
0.636	Remote Similarity	NPD4079	Approved
0.636	Remote Similarity	NPD1996	Discontinued
0.636	Remote Similarity	NPD7860	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD8459	Approved
0.6357	Remote Similarity	NPD8460	Approved
0.6357	Remote Similarity	NPD5891	Approved
0.6352	Remote Similarity	NPD7704	Clinical (unspecified phase)
0.635	Remote Similarity	NPD8364	Approved
0.635	Remote Similarity	NPD8375	Approved
0.635	Remote Similarity	NPD8363	Approved
0.6349	Remote Similarity	NPD7202	Clinical (unspecified phase)
0.6349	Remote Similarity	NPD6752	Phase 1
0.6349	Remote Similarity	NPD6753	Phase 1
0.6345	Remote Similarity	NPD7777	Approved
0.6345	Remote Similarity	NPD53	Approved
0.6345	Remote Similarity	NPD7778	Approved
0.6345	Remote Similarity	NPD7878	Phase 2
0.6344	Remote Similarity	NPD4075	Phase 2
0.6339	Remote Similarity	NPD2844	Phase 3
0.6339	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6336	Remote Similarity	NPD6217	Discontinued
0.6331	Remote Similarity	NPD5612	Discontinued
0.6325	Remote Similarity	NPD8525	Approved
0.6324	Remote Similarity	NPD4890	Phase 2
0.6322	Remote Similarity	NPD7576	Discontinued
0.6322	Remote Similarity	NPD8114	Approved
0.6322	Remote Similarity	NPD8115	Approved
0.6316	Remote Similarity	NPD3505	Approved
0.6316	Remote Similarity	NPD4341	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7865	Approved
0.6316	Remote Similarity	NPD3506	Approved
0.6316	Remote Similarity	NPD7557	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD3961	Discontinued
0.6306	Remote Similarity	NPD8442	Discontinued
0.6304	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6302	Remote Similarity	NPD4558	Phase 2
0.63	Remote Similarity	NPD5322	Clinical (unspecified phase)
0.6298	Remote Similarity	NPD8240	Discontinued
0.6296	Remote Similarity	NPD7568	Phase 1
0.6293	Remote Similarity	NPD6986	Phase 1
0.6292	Remote Similarity	NPD4600	Approved
0.6292	Remote Similarity	NPD4601	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