NPASS Compound

Structure

NPC467439 OpenBabel07101719522D 36 41 0 0 0 0 0 0 0 0999 V2000 -0.2079 -0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8392 0.6386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7514 3.9865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7111 0.7832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6622 0.4742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6456 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5522 2.0704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -0.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2464 2.4305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -1.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8066 1.9524 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5771 -4.1759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5032 1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8090 1.4013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 0.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4053 1.1433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7796 -3.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1974 2.1215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9135 -2.5933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2514 1.4476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9424 2.3987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5605 2.3987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6691 0.7431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5115 2.7077 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.1691 1.6092 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 0.6386 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.2514 1.4476 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.7514 2.9865 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9914 2.7077 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3999 1.0388 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5717 -4.0714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0634 2.6215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1704 -3.2624 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 29 1 0 0 0 0 2 30 1 0 0 0 0 3 31 1 0 0 0 0 4 6 2 0 0 0 0 4 14 1 0 0 0 0 5 7 2 0 0 0 0 5 15 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 14 1 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 17 1 0 0 0 0 10 14 2 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 21 1 0 0 0 0 12 33 1 0 0 0 0 12 35 1 0 0 0 0 13 34 1 0 0 0 0 13 36 1 0 0 0 0 16 17 2 0 0 0 0 16 27 1 0 0 0 0 17 29 1 0 0 0 0 18 20 2 0 0 0 0 18 33 1 0 0 0 0 19 21 2 0 0 0 0 19 34 1 0 0 0 0 20 35 1 0 0 0 0 21 36 1 0 0 0 0 22 23 1 0 0 0 0 22 28 2 0 0 0 0 22 30 1 0 0 0 0 23 31 1 0 0 0 0 23 32 2 0 0 0 0 24 26 2 0 0 0 0 24 30 1 0 0 0 0 24 31 1 0 0 0 0 25 27 2 0 0 0 0 25 28 1 0 0 0 0 25 29 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	383.14
Volume:	374.273
LogP:	2.386
LogD:	2.843
LogS:	-4.523
# Rotatable Bonds:	3
TPSA:	66.46
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.755
Synthetic Accessibility Score:	3.448
Fsp3:	0.381
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.846
MDCK Permeability:	5.877442526980303e-05
Pgp-inhibitor:	0.642
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.029
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	81.99726104736328%
Volume Distribution (VD):	2.017
Pgp-substrate:	8.787803649902344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.667
CYP1A2-substrate:	0.945
CYP2C19-inhibitor:	0.913
CYP2C19-substrate:	0.927
CYP2C9-inhibitor:	0.54
CYP2C9-substrate:	0.847
CYP2D6-inhibitor:	0.923
CYP2D6-substrate:	0.919
CYP3A4-inhibitor:	0.955
CYP3A4-substrate:	0.916

ADMET: Excretion

Clearance (CL):	14.362
Half-life (T1/2):	0.144

ADMET: Toxicity

hERG Blockers:	0.109
Human Hepatotoxicity (H-HT):	0.202
Drug-inuced Liver Injury (DILI):	0.563
AMES Toxicity:	0.171
Rat Oral Acute Toxicity:	0.774
Maximum Recommended Daily Dose:	0.886
Skin Sensitization:	0.086
Carcinogencity:	0.595
Eye Corrosion:	0.003
Eye Irritation:	0.014
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC467439

Natural Product ID:	NPC467439
*Common Name:**	Leucettamidine
IUPAC Name:	(5E)-5-[4,5-bis(1,3-benzodioxol-5-ylmethyl)-1-methylimidazol-2-yl]imino-2-imino-1,3-dimethylimidazolidin-4-one
Synonyms:	Leucettamidine
Standard InCHIKey:	RZKRATQHPLTYSI-GQZUJQTPSA-N
Standard InCHI:	InChI=1S/C25H24N6O5/c1-29-17(9-15-5-7-19-21(11-15)36-13-34-19)16(8-14-4-6-18-20(10-14)35-12-33-18)27-25(29)28-22-23(32)31(3)24(26)30(22)2/h4-7,10-11,26H,8-9,12-13H2,1-3H3/b26-24?,28-22+
SMILES:	Cn1c(Cc2ccc3c(c2)OCO3)c(Cc2ccc3c(c2)OCO3)nc1/N=C/1C(=O)N(C)C(=N)N1C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485054
PubChem CID:	20704716
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

*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
NPO18731	Leucetta microraphis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10691722]
NPO18731	Leucetta microraphis	Species	Leucettidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8383730]
NPO18731	Leucetta microraphis	Species	Leucettidae	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	1
Ki	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3068	Individual Protein	Leukotriene B4 receptor 1	Homo sapiens	IC50	=	15600.0	nM	PMID[496119]
NPT3068	Individual Protein	Leukotriene B4 receptor 1	Homo sapiens	Ki	=	5300.0	nM	PMID[496119]

☑ 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 NPC467439 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	510
0.1-0.2	3450
0.2-0.3	13658
0.3-0.4	7885
0.4-0.5	13197
0.5-0.6	3719
0.6-0.7	253
0.7-0.8	13
0.8-0.85	6
0.85-0.9	4
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9163	High Similarity	NPC17305
0.8756	High Similarity	NPC35761
0.8689	High Similarity	NPC12100
0.8632	High Similarity	NPC237978
0.8429	Intermediate Similarity	NPC136924
0.8341	Intermediate Similarity	NPC308906
0.831	Intermediate Similarity	NPC46970
0.825	Intermediate Similarity	NPC280638
0.7757	Intermediate Similarity	NPC242923
0.7468	Intermediate Similarity	NPC477806
0.7468	Intermediate Similarity	NPC477796
0.7468	Intermediate Similarity	NPC477795
0.7468	Intermediate Similarity	NPC477805
0.734	Intermediate Similarity	NPC181905
0.7107	Intermediate Similarity	NPC292003
0.6966	Remote Similarity	NPC160666
0.691	Remote Similarity	NPC323244
0.6834	Remote Similarity	NPC474852
0.6818	Remote Similarity	NPC477019
0.6807	Remote Similarity	NPC208898
0.6793	Remote Similarity	NPC328924
0.6774	Remote Similarity	NPC303374
0.6763	Remote Similarity	NPC471614
0.6748	Remote Similarity	NPC472066
0.6748	Remote Similarity	NPC472031
0.6748	Remote Similarity	NPC472067
0.6711	Remote Similarity	NPC135549
0.6711	Remote Similarity	NPC313189
0.6695	Remote Similarity	NPC187145
0.668	Remote Similarity	NPC51854
0.6667	Remote Similarity	NPC472068
0.6651	Remote Similarity	NPC79213
0.6651	Remote Similarity	NPC204385
0.664	Remote Similarity	NPC9729
0.6638	Remote Similarity	NPC171409
0.6638	Remote Similarity	NPC96405
0.6638	Remote Similarity	NPC53069
0.6638	Remote Similarity	NPC202768
0.6638	Remote Similarity	NPC296482
0.6623	Remote Similarity	NPC113369
0.662	Remote Similarity	NPC206201
0.6569	Remote Similarity	NPC115595
0.6537	Remote Similarity	NPC149471
0.6537	Remote Similarity	NPC271215
0.6518	Remote Similarity	NPC234197
0.65	Remote Similarity	NPC133140
0.65	Remote Similarity	NPC195268
0.6468	Remote Similarity	NPC250178
0.6468	Remote Similarity	NPC46451
0.6461	Remote Similarity	NPC253675
0.6458	Remote Similarity	NPC315822
0.6444	Remote Similarity	NPC25897
0.6426	Remote Similarity	NPC23614
0.6426	Remote Similarity	NPC100079
0.6422	Remote Similarity	NPC251160
0.6407	Remote Similarity	NPC188420
0.64	Remote Similarity	NPC476578
0.64	Remote Similarity	NPC476582
0.64	Remote Similarity	NPC4071
0.6385	Remote Similarity	NPC312872
0.6383	Remote Similarity	NPC305984
0.6376	Remote Similarity	NPC261388
0.6373	Remote Similarity	NPC13397
0.6371	Remote Similarity	NPC171393
0.6371	Remote Similarity	NPC295452
0.6344	Remote Similarity	NPC54537
0.6344	Remote Similarity	NPC31930
0.6332	Remote Similarity	NPC36229
0.6332	Remote Similarity	NPC16452
0.6332	Remote Similarity	NPC476581
0.6325	Remote Similarity	NPC266931
0.632	Remote Similarity	NPC71238
0.632	Remote Similarity	NPC82548
0.6316	Remote Similarity	NPC30540
0.6316	Remote Similarity	NPC295898
0.6314	Remote Similarity	NPC238945
0.6298	Remote Similarity	NPC235076
0.6293	Remote Similarity	NPC174758
0.6291	Remote Similarity	NPC85482
0.6288	Remote Similarity	NPC223427
0.6287	Remote Similarity	NPC303658
0.6283	Remote Similarity	NPC127085
0.6281	Remote Similarity	NPC157931
0.6266	Remote Similarity	NPC290689
0.626	Remote Similarity	NPC56271
0.6255	Remote Similarity	NPC471762
0.6255	Remote Similarity	NPC236668
0.625	Remote Similarity	NPC280272
0.624	Remote Similarity	NPC150447
0.6239	Remote Similarity	NPC54981
0.6235	Remote Similarity	NPC295228
0.6233	Remote Similarity	NPC164608
0.6229	Remote Similarity	NPC146976
0.622	Remote Similarity	NPC22481
0.6218	Remote Similarity	NPC204446
0.6213	Remote Similarity	NPC471603
0.6202	Remote Similarity	NPC63109
0.62	Remote Similarity	NPC99891
0.6198	Remote Similarity	NPC471615
0.6189	Remote Similarity	NPC194740
0.6179	Remote Similarity	NPC247251
0.6176	Remote Similarity	NPC477633
0.6174	Remote Similarity	NPC135887
0.6174	Remote Similarity	NPC199277
0.6169	Remote Similarity	NPC108342
0.6167	Remote Similarity	NPC54066
0.6163	Remote Similarity	NPC278525
0.6157	Remote Similarity	NPC176538
0.6157	Remote Similarity	NPC26543
0.6157	Remote Similarity	NPC242728
0.6154	Remote Similarity	NPC102760
0.6154	Remote Similarity	NPC138083
0.6154	Remote Similarity	NPC469589
0.6147	Remote Similarity	NPC475774
0.6145	Remote Similarity	NPC184680
0.6145	Remote Similarity	NPC182907
0.6145	Remote Similarity	NPC189903
0.6145	Remote Similarity	NPC473183
0.6144	Remote Similarity	NPC112206
0.6144	Remote Similarity	NPC94157
0.6144	Remote Similarity	NPC472098
0.6144	Remote Similarity	NPC202605
0.6138	Remote Similarity	NPC476999
0.6134	Remote Similarity	NPC274982
0.613	Remote Similarity	NPC232727
0.6129	Remote Similarity	NPC473184
0.6123	Remote Similarity	NPC149962
0.6122	Remote Similarity	NPC66777
0.612	Remote Similarity	NPC470785
0.612	Remote Similarity	NPC166722
0.6119	Remote Similarity	NPC32064
0.6119	Remote Similarity	NPC287588
0.6116	Remote Similarity	NPC118121
0.6114	Remote Similarity	NPC18487
0.6111	Remote Similarity	NPC476465
0.6111	Remote Similarity	NPC39092
0.6103	Remote Similarity	NPC24954
0.61	Remote Similarity	NPC95366
0.61	Remote Similarity	NPC248505
0.6096	Remote Similarity	NPC144314
0.6089	Remote Similarity	NPC220852
0.6085	Remote Similarity	NPC174672
0.608	Remote Similarity	NPC28945
0.6078	Remote Similarity	NPC473460
0.607	Remote Similarity	NPC50548
0.6059	Remote Similarity	NPC167860
0.6059	Remote Similarity	NPC123976
0.6056	Remote Similarity	NPC101350
0.6056	Remote Similarity	NPC470784
0.6056	Remote Similarity	NPC474183
0.6054	Remote Similarity	NPC478006
0.6054	Remote Similarity	NPC74619
0.6052	Remote Similarity	NPC473422
0.6052	Remote Similarity	NPC210256
0.605	Remote Similarity	NPC469592
0.605	Remote Similarity	NPC137172
0.605	Remote Similarity	NPC145446
0.605	Remote Similarity	NPC471080
0.6043	Remote Similarity	NPC123859
0.604	Remote Similarity	NPC272549
0.6039	Remote Similarity	NPC475959
0.6038	Remote Similarity	NPC315467
0.6036	Remote Similarity	NPC179704
0.6033	Remote Similarity	NPC477533
0.6033	Remote Similarity	NPC323969
0.6032	Remote Similarity	NPC69843
0.6025	Remote Similarity	NPC130570
0.6024	Remote Similarity	NPC141053
0.6023	Remote Similarity	NPC314882
0.602	Remote Similarity	NPC28641
0.602	Remote Similarity	NPC194359
0.6017	Remote Similarity	NPC469594
0.6016	Remote Similarity	NPC285343
0.6016	Remote Similarity	NPC235685
0.6016	Remote Similarity	NPC257851
0.6015	Remote Similarity	NPC478009
0.601	Remote Similarity	NPC318862
0.6009	Remote Similarity	NPC245816
0.6009	Remote Similarity	NPC315498
0.6009	Remote Similarity	NPC230942
0.6009	Remote Similarity	NPC476138
0.6008	Remote Similarity	NPC316981
0.6008	Remote Similarity	NPC210296
0.6008	Remote Similarity	NPC26679
0.6	Remote Similarity	NPC124313
0.6	Remote Similarity	NPC210148
0.6	Remote Similarity	NPC223223
0.6	Remote Similarity	NPC96406
0.6	Remote Similarity	NPC11147
0.6	Remote Similarity	NPC170114
0.6	Remote Similarity	NPC233029
0.6	Remote Similarity	NPC474595
0.5992	Remote Similarity	NPC476997
0.5992	Remote Similarity	NPC314954
0.5991	Remote Similarity	NPC176127
0.5984	Remote Similarity	NPC207283
0.5984	Remote Similarity	NPC84164
0.5984	Remote Similarity	NPC469554
0.5983	Remote Similarity	NPC476287
0.5982	Remote Similarity	NPC276120

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 NPC467439 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	254
0.1-0.2	665
0.2-0.3	867
0.3-0.4	1872
0.4-0.5	3349
0.5-0.6	1876
0.6-0.7	254
0.7-0.8	13
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
0.7793	Intermediate Similarity	NPD4048	Approved
0.7738	Intermediate Similarity	NPD4132	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD3590	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2530	Phase 2
0.7345	Intermediate Similarity	NPD5703	Discontinued
0.7311	Intermediate Similarity	NPD7588	Discontinued
0.7198	Intermediate Similarity	NPD4080	Discontinued
0.7188	Intermediate Similarity	NPD7980	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2060	Approved
0.7082	Intermediate Similarity	NPD4885	Approved
0.6916	Remote Similarity	NPD6643	Discontinued
0.6898	Remote Similarity	NPD6743	Phase 2
0.6898	Remote Similarity	NPD6742	Phase 2
0.687	Remote Similarity	NPD6856	Discontinued
0.6832	Remote Similarity	NPD8525	Approved
0.682	Remote Similarity	NPD5920	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD7620	Phase 2
0.6807	Remote Similarity	NPD3838	Phase 3
0.6792	Remote Similarity	NPD5107	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD8292	Phase 2
0.6763	Remote Similarity	NPD6537	Approved
0.6763	Remote Similarity	NPD6536	Approved
0.6762	Remote Similarity	NPD5118	Phase 2
0.6754	Remote Similarity	NPD8524	Approved
0.6748	Remote Similarity	NPD6244	Phase 3
0.6748	Remote Similarity	NPD6243	Phase 3
0.6743	Remote Similarity	NPD978	Clinical (unspecified phase)
0.674	Remote Similarity	NPD2540	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD5070	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD6202	Discontinued
0.6709	Remote Similarity	NPD6708	Discontinued
0.6694	Remote Similarity	NPD7486	Phase 1
0.6681	Remote Similarity	NPD3042	Approved
0.6681	Remote Similarity	NPD3043	Approved
0.6667	Remote Similarity	NPD1954	Phase 1
0.6667	Remote Similarity	NPD949	Phase 1
0.6654	Remote Similarity	NPD5459	Phase 2
0.6639	Remote Similarity	NPD5861	Clinical (unspecified phase)
0.6638	Remote Similarity	NPD3816	Phase 1
0.6638	Remote Similarity	NPD3815	Phase 1
0.6627	Remote Similarity	NPD6216	Approved
0.6625	Remote Similarity	NPD6186	Approved
0.6625	Remote Similarity	NPD6223	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD3541	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD4995	Approved
0.6611	Remote Similarity	NPD4996	Approved
0.661	Remote Similarity	NPD3938	Phase 1
0.6609	Remote Similarity	NPD8105	Discontinued
0.6608	Remote Similarity	NPD5658	Approved
0.6598	Remote Similarity	NPD6760	Discontinued
0.6573	Remote Similarity	NPD4558	Phase 2
0.6571	Remote Similarity	NPD5833	Phase 1
0.6571	Remote Similarity	NPD6473	Phase 1
0.6569	Remote Similarity	NPD4925	Approved
0.6557	Remote Similarity	NPD5905	Phase 1
0.6555	Remote Similarity	NPD1882	Phase 2
0.6535	Remote Similarity	NPD6228	Discontinued
0.6526	Remote Similarity	NPD3920	Phase 2
0.6518	Remote Similarity	NPD3602	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD4418	Discontinued
0.6515	Remote Similarity	NPD7705	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6528	Phase 1
0.6508	Remote Similarity	NPD8442	Discontinued
0.6504	Remote Similarity	NPD6517	Phase 3
0.65	Remote Similarity	NPD3924	Approved
0.65	Remote Similarity	NPD3922	Approved
0.65	Remote Similarity	NPD994	Phase 2
0.65	Remote Similarity	NPD7689	Approved
0.65	Remote Similarity	NPD996	Phase 2
0.65	Remote Similarity	NPD1900	Clinical (unspecified phase)
0.65	Remote Similarity	NPD3923	Approved
0.65	Remote Similarity	NPD3921	Approved
0.6498	Remote Similarity	NPD7758	Approved
0.6498	Remote Similarity	NPD2917	Approved
0.6498	Remote Similarity	NPD7757	Approved
0.649	Remote Similarity	NPD7117	Phase 2
0.649	Remote Similarity	NPD2929	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD3408	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6772	Clinical (unspecified phase)
0.6473	Remote Similarity	NPD5139	Phase 1
0.6468	Remote Similarity	NPD3763	Approved
0.6466	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5528	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD5529	Phase 1
0.6456	Remote Similarity	NPD6036	Suspended
0.6437	Remote Similarity	NPD5051	Phase 1
0.6434	Remote Similarity	NPD8287	Phase 1
0.6434	Remote Similarity	NPD8288	Phase 2
0.6422	Remote Similarity	NPD2794	Discontinued
0.6419	Remote Similarity	NPD2599	Approved
0.6419	Remote Similarity	NPD2600	Approved
0.6419	Remote Similarity	NPD2601	Approved
0.6413	Remote Similarity	NPD2482	Clinical (unspecified phase)
0.6411	Remote Similarity	NPD5802	Phase 2
0.6409	Remote Similarity	NPD4442	Phase 2
0.6408	Remote Similarity	NPD5805	Approved
0.6404	Remote Similarity	NPD1287	Phase 2
0.6395	Remote Similarity	NPD4457	Phase 2
0.6395	Remote Similarity	NPD5949	Phase 3
0.6382	Remote Similarity	NPD7729	Clinical (unspecified phase)
0.6379	Remote Similarity	NPD7943	Suspended
0.6375	Remote Similarity	NPD7398	Approved
0.6375	Remote Similarity	NPD7397	Approved
0.6372	Remote Similarity	NPD6612	Phase 2
0.6364	Remote Similarity	NPD3349	Phase 2
0.6364	Remote Similarity	NPD4157	Discontinued
0.636	Remote Similarity	NPD6460	Clinical (unspecified phase)
0.636	Remote Similarity	NPD3254	Phase 1
0.636	Remote Similarity	NPD3255	Phase 1
0.6353	Remote Similarity	NPD8049	Phase 2
0.635	Remote Similarity	NPD7682	Approved
0.635	Remote Similarity	NPD7684	Approved
0.635	Remote Similarity	NPD5018	Phase 3
0.6345	Remote Similarity	NPD6572	Phase 2
0.6345	Remote Similarity	NPD6573	Phase 3
0.6342	Remote Similarity	NPD5116	Phase 1
0.6335	Remote Similarity	NPD2410	Phase 2
0.6335	Remote Similarity	NPD7898	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD7897	Phase 3
0.6333	Remote Similarity	NPD4932	Clinical (unspecified phase)
0.6332	Remote Similarity	NPD2130	Discontinued
0.633	Remote Similarity	NPD7280	Phase 3
0.633	Remote Similarity	NPD7281	Phase 3
0.6327	Remote Similarity	NPD2757	Phase 2
0.6323	Remote Similarity	NPD6046	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7197	Approved
0.632	Remote Similarity	NPD6230	Discontinued
0.631	Remote Similarity	NPD5007	Approved
0.631	Remote Similarity	NPD3886	Phase 1
0.6308	Remote Similarity	NPD5966	Clinical (unspecified phase)
0.6307	Remote Similarity	NPD7051	Phase 3
0.6307	Remote Similarity	NPD7050	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD459	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD1286	Suspended
0.6292	Remote Similarity	NPD5045	Phase 2
0.6287	Remote Similarity	NPD3313	Phase 2
0.6286	Remote Similarity	NPD4306	Phase 1
0.628	Remote Similarity	NPD5731	Approved
0.628	Remote Similarity	NPD5732	Approved
0.6278	Remote Similarity	NPD7198	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD4414	Discontinued
0.6271	Remote Similarity	NPD2412	Clinical (unspecified phase)
0.6267	Remote Similarity	NPD774	Phase 3
0.6266	Remote Similarity	NPD3392	Approved
0.6266	Remote Similarity	NPD7465	Suspended
0.6266	Remote Similarity	NPD1258	Discontinued
0.626	Remote Similarity	NPD5008	Approved
0.6256	Remote Similarity	NPD3814	Phase 1
0.6255	Remote Similarity	NPD1624	Phase 2
0.6255	Remote Similarity	NPD5014	Discontinued
0.625	Remote Similarity	NPD3631	Phase 3
0.6245	Remote Similarity	NPD8256	Approved
0.6245	Remote Similarity	NPD2813	Phase 3
0.6245	Remote Similarity	NPD8258	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD2812	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD5052	Clinical (unspecified phase)
0.6245	Remote Similarity	NPD8257	Approved
0.6237	Remote Similarity	NPD8421	Discontinued
0.6231	Remote Similarity	NPD5869	Phase 2
0.6231	Remote Similarity	NPD6814	Phase 3
0.6231	Remote Similarity	NPD5870	Clinical (unspecified phase)
0.6227	Remote Similarity	NPD2762	Phase 2
0.6222	Remote Similarity	NPD2769	Approved
0.6221	Remote Similarity	NPD5447	Phase 2
0.6221	Remote Similarity	NPD6023	Discontinued
0.622	Remote Similarity	NPD4916	Discontinued
0.6217	Remote Similarity	NPD6153	Approved
0.6215	Remote Similarity	NPD7067	Approved
0.6215	Remote Similarity	NPD7068	Approved
0.6213	Remote Similarity	NPD5866	Approved
0.6211	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD5539	Phase 2
0.6211	Remote Similarity	NPD6877	Discontinued
0.6203	Remote Similarity	NPD5079	Phase 2
0.6203	Remote Similarity	NPD4935	Phase 2
0.6201	Remote Similarity	NPD7134	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6848	Phase 1
0.6199	Remote Similarity	NPD8046	Discontinued
0.6198	Remote Similarity	NPD2835	Phase 2
0.6197	Remote Similarity	NPD3983	Phase 3
0.6197	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.6192	Remote Similarity	NPD4555	Clinical (unspecified phase)
0.6189	Remote Similarity	NPD5509	Phase 1
0.6185	Remote Similarity	NPD4394	Clinical (unspecified phase)
0.6184	Remote Similarity	NPD4052	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD3343	Phase 3
0.6182	Remote Similarity	NPD5917	Clinical (unspecified phase)
0.6181	Remote Similarity	NPD5644	Phase 1
0.618	Remote Similarity	NPD4154	Approved
0.6179	Remote Similarity	NPD705	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5080	Phase 2
0.6173	Remote Similarity	NPD1273	Discontinued
0.617	Remote Similarity	NPD4131	Phase 3
0.6169	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD7678	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4673	Phase 2
0.6164	Remote Similarity	NPD8403	Phase 1
0.6163	Remote Similarity	NPD7938	Suspended
0.616	Remote Similarity	NPD8016	Phase 3

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