NPASS Compound

Structure

NPC469537 OpenBabel07101719252D 28 33 0 0 1 0 0 0 0 0999 V2000 3.5814 0.8445 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5814 -0.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0204 -1.7442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1018 -0.5787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9703 -2.2563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1333 0.0746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4395 -1.0994 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1318 -0.3131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3624 -1.3257 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8979 -2.0714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8979 -0.1274 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7397 -0.6134 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7397 -1.5854 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9115 -0.7613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5751 -1.3364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0018 -1.6031 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0832 -0.4376 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0562 -1.5854 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7509 -0.8950 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2155 -2.2394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0108 -0.7873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1318 -1.8857 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7463 -2.3795 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 1.0562 -0.6134 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8177 -3.0023 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7748 -1.5557 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4515 0.2745 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 16 2 0 0 0 0 6 17 2 0 0 0 0 7 8 1 0 0 0 0 8 25 1 0 0 0 0 9 14 1 0 0 0 0 9 15 2 0 0 0 0 10 18 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 2 1 1 0 0 0 12 13 1 0 0 0 0 13 10 1 6 0 0 0 13 14 1 0 0 0 0 14 19 2 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 22 1 1 0 0 0 18 25 1 0 0 0 0 19 22 1 0 0 0 0 19 24 1 0 0 0 0 20 23 1 0 0 0 0 20 26 2 0 0 0 0 21 24 1 0 0 0 0 21 27 2 0 0 0 0 22 7 1 6 0 0 0 25 28 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	377.17
Volume:	378.635
LogP:	0.616
LogD:	0.569
LogS:	-2.446
# Rotatable Bonds:	2
TPSA:	88.15
# H-Bond Aceptor:	6
# H-Bond Donor:	2
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.642
Synthetic Accessibility Score:	5.87
Fsp3:	0.455
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:	-5.575
MDCK Permeability:	2.9432441806420684e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.962
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.31
Plasma Protein Binding (PPB):	41.322898864746094%
Volume Distribution (VD):	1.818
Pgp-substrate:	61.192142486572266%

ADMET: Metabolism

CYP1A2-inhibitor:	0.009
CYP1A2-substrate:	0.462
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.802
CYP2C9-inhibitor:	0.01
CYP2C9-substrate:	0.614
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.066
CYP3A4-substrate:	0.927

ADMET: Excretion

Clearance (CL):	5.377
Half-life (T1/2):	0.795

ADMET: Toxicity

hERG Blockers:	0.335
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.058
AMES Toxicity:	0.923
Rat Oral Acute Toxicity:	0.948
Maximum Recommended Daily Dose:	0.977
Skin Sensitization:	0.182
Carcinogencity:	0.944
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.911

Download Data

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

Natural Product: NPC469537

Natural Product ID:	NPC469537
*Common Name:**	Leuconicine F
IUPAC Name:	n.a.
Synonyms:	Leuconicine F
Standard InCHIKey:	GDXGWPRFCUUOJJ-TZSLYKAUSA-N
Standard InCHI:	InChI=1S/C22H23N3O3/c1-2-12-11-25(28)8-7-22-16-5-3-4-6-17(16)24-19(22)14(13(12)10-18(22)25)9-15(20(23)26)21(24)27/h3-6,9,12-13,18H,2,7-8,10-11H2,1H3,(H2,23,26)/t12-,13+,18+,22-,25?/m1/s1
SMILES:	CCC1C[N+]2(CCC34C2CC1C5=C3N(C6=CC=CC=C46)C(=O)C(=C5)C(=O)N)[O-]
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1086393
PubChem CID:	46881270
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0000210] Carbazoles

*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
NPO32945	leuconotis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20035556]
NPO32945	leuconotis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20515042]

☑ 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
Cell Line	1
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	25.0	ug.mL-1	PMID[555295]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	25.0	ug.mL-1	PMID[555295]

☑ 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 NPC469537 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	532
0.1-0.2	2936
0.2-0.3	14556
0.3-0.4	17262
0.4-0.5	3336
0.5-0.6	2595
0.6-0.7	1349
0.7-0.8	123
0.8-0.85	5
0.85-0.9	0
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9481	High Similarity	NPC130251
0.913	High Similarity	NPC301760
0.8973	High Similarity	NPC469536
0.8571	High Similarity	NPC154602
0.8571	High Similarity	NPC243756
0.8267	Intermediate Similarity	NPC285381
0.8267	Intermediate Similarity	NPC122106
0.7959	Intermediate Similarity	NPC22082
0.7959	Intermediate Similarity	NPC186284
0.7702	Intermediate Similarity	NPC63047
0.7702	Intermediate Similarity	NPC475248
0.7622	Intermediate Similarity	NPC469726
0.7622	Intermediate Similarity	NPC329338
0.7613	Intermediate Similarity	NPC475763
0.7453	Intermediate Similarity	NPC469741
0.745	Intermediate Similarity	NPC471123
0.7438	Intermediate Similarity	NPC36495
0.7438	Intermediate Similarity	NPC193410
0.7436	Intermediate Similarity	NPC318086
0.7391	Intermediate Similarity	NPC248117
0.7337	Intermediate Similarity	NPC286994
0.7317	Intermediate Similarity	NPC214960
0.7317	Intermediate Similarity	NPC279527
0.7284	Intermediate Similarity	NPC225319
0.7278	Intermediate Similarity	NPC66936
0.7273	Intermediate Similarity	NPC223595
0.7273	Intermediate Similarity	NPC167724
0.7273	Intermediate Similarity	NPC224970
0.7267	Intermediate Similarity	NPC123241
0.7267	Intermediate Similarity	NPC61013
0.7267	Intermediate Similarity	NPC222029
0.7261	Intermediate Similarity	NPC109787
0.7239	Intermediate Similarity	NPC99632
0.7239	Intermediate Similarity	NPC293458
0.7239	Intermediate Similarity	NPC282339
0.7237	Intermediate Similarity	NPC469560
0.7219	Intermediate Similarity	NPC260075
0.7134	Intermediate Similarity	NPC264589
0.7134	Intermediate Similarity	NPC472117
0.7073	Intermediate Similarity	NPC309531
0.7073	Intermediate Similarity	NPC472102
0.7067	Intermediate Similarity	NPC53044
0.7055	Intermediate Similarity	NPC113946
0.7041	Intermediate Similarity	NPC473743
0.7032	Intermediate Similarity	NPC471164
0.7025	Intermediate Similarity	NPC469735
0.6981	Remote Similarity	NPC469740
0.6966	Remote Similarity	NPC475915
0.6959	Remote Similarity	NPC264482
0.6959	Remote Similarity	NPC203202
0.6946	Remote Similarity	NPC472106
0.6928	Remote Similarity	NPC472101
0.6928	Remote Similarity	NPC472120
0.6909	Remote Similarity	NPC276085
0.6894	Remote Similarity	NPC473329
0.6879	Remote Similarity	NPC6974
0.6879	Remote Similarity	NPC218594
0.6879	Remote Similarity	NPC99043
0.6867	Remote Similarity	NPC68650
0.6863	Remote Similarity	NPC162417
0.6863	Remote Similarity	NPC316104
0.6859	Remote Similarity	NPC315051
0.6848	Remote Similarity	NPC104345
0.6842	Remote Similarity	NPC251212
0.6842	Remote Similarity	NPC139085
0.6842	Remote Similarity	NPC214626
0.6826	Remote Similarity	NPC286871
0.6788	Remote Similarity	NPC29285
0.6774	Remote Similarity	NPC267508
0.6748	Remote Similarity	NPC206592
0.6726	Remote Similarity	NPC176983
0.6725	Remote Similarity	NPC472118
0.6724	Remote Similarity	NPC186669
0.6712	Remote Similarity	NPC177684
0.6712	Remote Similarity	NPC291962
0.6707	Remote Similarity	NPC117032
0.6705	Remote Similarity	NPC475097
0.6667	Remote Similarity	NPC295021
0.6667	Remote Similarity	NPC161956
0.6667	Remote Similarity	NPC212799
0.6667	Remote Similarity	NPC478076
0.6667	Remote Similarity	NPC258531
0.6667	Remote Similarity	NPC112373
0.6647	Remote Similarity	NPC242269
0.6645	Remote Similarity	NPC209389
0.6644	Remote Similarity	NPC264580
0.6629	Remote Similarity	NPC97584
0.6622	Remote Similarity	NPC257490
0.6607	Remote Similarity	NPC471122
0.6592	Remote Similarity	NPC52262
0.659	Remote Similarity	NPC355
0.6579	Remote Similarity	NPC478079
0.6579	Remote Similarity	NPC145754
0.6577	Remote Similarity	NPC39818
0.6573	Remote Similarity	NPC159963
0.6569	Remote Similarity	NPC291610
0.6568	Remote Similarity	NPC201424
0.6556	Remote Similarity	NPC473615
0.6554	Remote Similarity	NPC179605
0.6554	Remote Similarity	NPC279385
0.6552	Remote Similarity	NPC285622
0.6534	Remote Similarity	NPC476326
0.6519	Remote Similarity	NPC14994
0.6519	Remote Similarity	NPC229484
0.651	Remote Similarity	NPC103292
0.6505	Remote Similarity	NPC162440
0.6503	Remote Similarity	NPC469525
0.6503	Remote Similarity	NPC25401
0.6497	Remote Similarity	NPC300299
0.6494	Remote Similarity	NPC187231
0.6484	Remote Similarity	NPC292675
0.6481	Remote Similarity	NPC136002
0.6478	Remote Similarity	NPC83214
0.6474	Remote Similarity	NPC33507
0.6453	Remote Similarity	NPC475420
0.6453	Remote Similarity	NPC471124
0.6444	Remote Similarity	NPC2933
0.644	Remote Similarity	NPC329833
0.6438	Remote Similarity	NPC207554
0.6425	Remote Similarity	NPC476428
0.6424	Remote Similarity	NPC254698
0.641	Remote Similarity	NPC207428
0.641	Remote Similarity	NPC473962
0.6409	Remote Similarity	NPC307396
0.6409	Remote Similarity	NPC259626
0.6405	Remote Similarity	NPC252794
0.6398	Remote Similarity	NPC471574
0.6395	Remote Similarity	NPC313673
0.6389	Remote Similarity	NPC470205
0.6389	Remote Similarity	NPC256288
0.6383	Remote Similarity	NPC100863
0.6376	Remote Similarity	NPC226143
0.6374	Remote Similarity	NPC315368
0.6374	Remote Similarity	NPC143457
0.6368	Remote Similarity	NPC469732
0.6364	Remote Similarity	NPC96901
0.6364	Remote Similarity	NPC473880
0.6364	Remote Similarity	NPC161861
0.6359	Remote Similarity	NPC105055
0.6359	Remote Similarity	NPC5630
0.6359	Remote Similarity	NPC22689
0.6358	Remote Similarity	NPC238499
0.6358	Remote Similarity	NPC268534
0.6351	Remote Similarity	NPC313449
0.6349	Remote Similarity	NPC106118
0.6346	Remote Similarity	NPC126458
0.6343	Remote Similarity	NPC32534
0.634	Remote Similarity	NPC79698
0.6337	Remote Similarity	NPC194881
0.6335	Remote Similarity	NPC243162
0.633	Remote Similarity	NPC472541
0.633	Remote Similarity	NPC472542
0.633	Remote Similarity	NPC232130
0.6328	Remote Similarity	NPC470548
0.6324	Remote Similarity	NPC203628
0.6324	Remote Similarity	NPC22476
0.6319	Remote Similarity	NPC277157
0.6304	Remote Similarity	NPC75496
0.6301	Remote Similarity	NPC469541
0.6301	Remote Similarity	NPC478182
0.6296	Remote Similarity	NPC2823
0.6282	Remote Similarity	NPC280807
0.6282	Remote Similarity	NPC472245
0.6282	Remote Similarity	NPC314431
0.628	Remote Similarity	NPC311330
0.6279	Remote Similarity	NPC474058
0.6277	Remote Similarity	NPC472539
0.6277	Remote Similarity	NPC470787
0.6277	Remote Similarity	NPC472540
0.6272	Remote Similarity	NPC281094
0.6271	Remote Similarity	NPC177261
0.6265	Remote Similarity	NPC478186
0.6259	Remote Similarity	NPC246904
0.6257	Remote Similarity	NPC14325
0.6257	Remote Similarity	NPC28848
0.6243	Remote Similarity	NPC472121
0.6242	Remote Similarity	NPC192209
0.6242	Remote Similarity	NPC231382
0.6225	Remote Similarity	NPC316582
0.6223	Remote Similarity	NPC221687
0.6221	Remote Similarity	NPC469461
0.6211	Remote Similarity	NPC138615
0.6211	Remote Similarity	NPC218733
0.6211	Remote Similarity	NPC265642
0.6211	Remote Similarity	NPC132874
0.6209	Remote Similarity	NPC477159
0.6207	Remote Similarity	NPC478184
0.6207	Remote Similarity	NPC328270
0.6205	Remote Similarity	NPC470440
0.6201	Remote Similarity	NPC320147
0.62	Remote Similarity	NPC228515
0.6199	Remote Similarity	NPC84317
0.6196	Remote Similarity	NPC470301
0.6194	Remote Similarity	NPC250476
0.619	Remote Similarity	NPC187036
0.619	Remote Similarity	NPC473375
0.619	Remote Similarity	NPC303214
0.619	Remote Similarity	NPC97100
0.6183	Remote Similarity	NPC473298
0.6182	Remote Similarity	NPC20144

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 NPC469537 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	278
0.1-0.2	568
0.2-0.3	835
0.3-0.4	2110
0.4-0.5	2530
0.5-0.6	2097
0.6-0.7	685
0.7-0.8	47
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
0.7305	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5527	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5526	Phase 2
0.7248	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5179	Approved
0.7246	Intermediate Similarity	NPD5180	Approved
0.7246	Intermediate Similarity	NPD5181	Approved
0.7234	Intermediate Similarity	NPD1668	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD3548	Approved
0.7034	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6768	Approved
0.6985	Remote Similarity	NPD1065	Approved
0.6985	Remote Similarity	NPD1064	Approved
0.6975	Remote Similarity	NPD2790	Discontinued
0.6962	Remote Similarity	NPD6017	Discontinued
0.6957	Remote Similarity	NPD4116	Approved
0.6879	Remote Similarity	NPD6566	Discontinued
0.6855	Remote Similarity	NPD5932	Phase 3
0.6855	Remote Similarity	NPD5931	Phase 3
0.6855	Remote Similarity	NPD5933	Phase 3
0.6835	Remote Similarity	NPD4430	Phase 2
0.6835	Remote Similarity	NPD7633	Discontinued
0.6821	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5918	Discontinued
0.6774	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4549	Discontinued
0.6747	Remote Similarity	NPD8630	Approved
0.6738	Remote Similarity	NPD2039	Approved
0.6738	Remote Similarity	NPD2038	Approved
0.671	Remote Similarity	NPD2791	Discontinued
0.6707	Remote Similarity	NPD3248	Phase 1
0.6667	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6489	Phase 3
0.6643	Remote Similarity	NPD2913	Approved
0.6643	Remote Similarity	NPD2914	Approved
0.6627	Remote Similarity	NPD7220	Approved
0.6626	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2820	Phase 3
0.6624	Remote Similarity	NPD6358	Phase 2
0.662	Remote Similarity	NPD3865	Approved
0.6606	Remote Similarity	NPD8401	Approved
0.6606	Remote Similarity	NPD8400	Approved
0.6606	Remote Similarity	NPD8402	Approved
0.6604	Remote Similarity	NPD2010	Phase 3
0.6603	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6395	Phase 2
0.6584	Remote Similarity	NPD7487	Discontinued
0.6584	Remote Similarity	NPD4347	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5993	Phase 1
0.6569	Remote Similarity	NPD708	Approved
0.6566	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2365	Approved
0.6541	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD3387	Approved
0.6524	Remote Similarity	NPD4942	Approved
0.6522	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD6342	Discontinued
0.6503	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD5131	Approved
0.649	Remote Similarity	NPD1640	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD5629	Discontinued
0.6478	Remote Similarity	NPD7254	Discontinued
0.6478	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD7142	Discontinued
0.6474	Remote Similarity	NPD2949	Approved
0.6474	Remote Similarity	NPD2950	Approved
0.6454	Remote Similarity	NPD4114	Approved
0.6454	Remote Similarity	NPD5253	Approved
0.6454	Remote Similarity	NPD4115	Approved
0.6452	Remote Similarity	NPD486	Clinical (unspecified phase)
0.645	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7072	Phase 2
0.6424	Remote Similarity	NPD979	Approved
0.642	Remote Similarity	NPD7082	Approved
0.642	Remote Similarity	NPD2129	Approved
0.641	Remote Similarity	NPD1920	Approved
0.641	Remote Similarity	NPD1919	Approved
0.6405	Remote Similarity	NPD6900	Discontinued
0.6405	Remote Similarity	NPD2840	Approved
0.6402	Remote Similarity	NPD1524	Phase 1
0.6402	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5727	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD2093	Discontinued
0.6398	Remote Similarity	NPD3625	Discontinued
0.6398	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD2999	Approved
0.6389	Remote Similarity	NPD3001	Approved
0.6384	Remote Similarity	NPD4075	Phase 2
0.6383	Remote Similarity	NPD3546	Approved
0.6383	Remote Similarity	NPD3545	Approved
0.638	Remote Similarity	NPD7259	Approved
0.6364	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6351	Remote Similarity	NPD7481	Approved
0.6351	Remote Similarity	NPD7480	Approved
0.6341	Remote Similarity	NPD7295	Approved
0.6327	Remote Similarity	NPD1723	Phase 2
0.6327	Remote Similarity	NPD1720	Phase 2
0.6316	Remote Similarity	NPD33	Approved
0.6316	Remote Similarity	NPD4393	Approved
0.6312	Remote Similarity	NPD5318	Discontinued
0.6307	Remote Similarity	NPD7663	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1175	Approved
0.6299	Remote Similarity	NPD797	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD3240	Phase 2
0.6296	Remote Similarity	NPD1953	Discontinued
0.6294	Remote Similarity	NPD1342	Approved
0.6294	Remote Similarity	NPD951	Approved
0.6294	Remote Similarity	NPD2351	Discontinued
0.6291	Remote Similarity	NPD1123	Approved
0.6291	Remote Similarity	NPD1124	Approved
0.6284	Remote Similarity	NPD1344	Phase 2
0.6284	Remote Similarity	NPD6069	Approved
0.6284	Remote Similarity	NPD6070	Approved
0.6275	Remote Similarity	NPD2938	Approved
0.6275	Remote Similarity	NPD2940	Approved
0.6272	Remote Similarity	NPD4121	Phase 3
0.6272	Remote Similarity	NPD4120	Approved
0.6271	Remote Similarity	NPD7854	Phase 2
0.6266	Remote Similarity	NPD1527	Phase 2
0.6265	Remote Similarity	NPD7478	Approved
0.6265	Remote Similarity	NPD6466	Approved
0.6265	Remote Similarity	NPD6467	Approved
0.6265	Remote Similarity	NPD4402	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD5631	Phase 3
0.625	Remote Similarity	NPD4178	Approved
0.625	Remote Similarity	NPD6102	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3376	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3277	Phase 3
0.625	Remote Similarity	NPD7795	Phase 2
0.625	Remote Similarity	NPD4176	Approved
0.6242	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD2754	Discontinued
0.6242	Remote Similarity	NPD6622	Phase 1
0.6242	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5743	Approved
0.6235	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD5742	Approved
0.6235	Remote Similarity	NPD1870	Approved
0.6235	Remote Similarity	NPD5741	Approved
0.6234	Remote Similarity	NPD2961	Approved
0.6234	Remote Similarity	NPD2962	Approved
0.6228	Remote Similarity	NPD5423	Phase 2
0.6226	Remote Similarity	NPD5182	Approved
0.6226	Remote Similarity	NPD5185	Approved
0.6226	Remote Similarity	NPD5184	Approved
0.6214	Remote Similarity	NPD4735	Approved
0.6214	Remote Similarity	NPD4734	Approved
0.6211	Remote Similarity	NPD4411	Phase 1
0.6211	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD3790	Phase 2
0.6201	Remote Similarity	NPD5104	Approved
0.62	Remote Similarity	NPD922	Approved
0.62	Remote Similarity	NPD5657	Phase 3
0.6193	Remote Similarity	NPD2413	Phase 2
0.619	Remote Similarity	NPD5748	Phase 2
0.6188	Remote Similarity	NPD5473	Discontinued
0.6188	Remote Similarity	NPD4329	Approved
0.6188	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD4330	Approved
0.6188	Remote Similarity	NPD1071	Clinical (unspecified phase)
0.6185	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.6171	Remote Similarity	NPD2915	Discontinued
0.6168	Remote Similarity	NPD7088	Discontinued
0.6164	Remote Similarity	NPD3137	Clinical (unspecified phase)
0.6163	Remote Similarity	NPD8060	Phase 1
0.6159	Remote Similarity	NPD178	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD993	Approved
0.6154	Remote Similarity	NPD990	Approved
0.6154	Remote Similarity	NPD7606	Phase 3
0.615	Remote Similarity	NPD5504	Discontinued
0.6149	Remote Similarity	NPD3551	Approved
0.6145	Remote Similarity	NPD4711	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5060	Phase 1
0.6141	Remote Similarity	NPD5075	Discontinued
0.6136	Remote Similarity	NPD8003	Clinical (unspecified phase)
0.6136	Remote Similarity	NPD8002	Clinical (unspecified phase)
0.6133	Remote Similarity	NPD2590	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD4985	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD8128	Discontinued
0.6127	Remote Similarity	NPD7114	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6301	Phase 2
0.612	Remote Similarity	NPD8281	Discontinued
0.6117	Remote Similarity	NPD7786	Discontinued
0.6115	Remote Similarity	NPD1781	Discontinued
0.6115	Remote Similarity	NPD2909	Phase 3
0.6115	Remote Similarity	NPD2908	Phase 3
0.6111	Remote Similarity	NPD6300	Approved
0.6111	Remote Similarity	NPD6299	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