NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	294.05
Volume:	277.065
LogP:	2.735
LogD:	3.022
LogS:	-4.861
# Rotatable Bonds:	4
TPSA:	41.9
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.478
Synthetic Accessibility Score:	3.4
Fsp3:	0.231
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:	-4.612
MDCK Permeability:	9.238692655344494e-06
Pgp-inhibitor:	0.0
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.066

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.99
Plasma Protein Binding (PPB):	52.372886657714844%
Volume Distribution (VD):	0.835
Pgp-substrate:	30.764060974121094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.983
CYP1A2-substrate:	0.947
CYP2C19-inhibitor:	0.833
CYP2C19-substrate:	0.81
CYP2C9-inhibitor:	0.859
CYP2C9-substrate:	0.459
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.186
CYP3A4-inhibitor:	0.114
CYP3A4-substrate:	0.765

ADMET: Excretion

Clearance (CL):	7.763
Half-life (T1/2):	0.068

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.658
Drug-inuced Liver Injury (DILI):	0.992
AMES Toxicity:	0.662
Rat Oral Acute Toxicity:	0.76
Maximum Recommended Daily Dose:	0.833
Skin Sensitization:	0.678
Carcinogencity:	0.454
Eye Corrosion:	0.003
Eye Irritation:	0.056
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC187231

Natural Product ID:	NPC187231
*Common Name:**	3-[1-Di(Methylsulfanyl)Methyleneamino-(E)-Methylidene]-1-Methoxy-2-Indolinone
IUPAC Name:	(3E)-3-[[bis(methylsulfanyl)methylideneamino]methylidene]-1-methoxyindol-2-one
Synonyms:
Standard InCHIKey:	JJQPWCPYNJNWID-CSKARUKUSA-N
Standard InCHI:	InChI=1S/C13H14N2O2S2/c1-17-15-11-7-5-4-6-9(11)10(12(15)16)8-14-13(18-2)19-3/h4-8H,1-3H3/b10-8+
SMILES:	CON1C(=O)/C(=C/N=C(SC)SC)/c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL103746
PubChem CID:	44333108
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles 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
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10571166]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27700070]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30232882]
NPO6409	Eutrema japonicum	Species	Brassicaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO6409	Eutrema japonicum	Species	Brassicaceae	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
Others	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4113	Organism	Leptosphaeria maculans	Leptosphaeria maculans	Inhibition	=	50.0	%	PMID[525419]

☑ 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 NPC187231 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	256
0.1-0.2	4254
0.2-0.3	14580
0.3-0.4	16286
0.4-0.5	5267
0.5-0.6	1871
0.6-0.7	174
0.7-0.8	7
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8345	Intermediate Similarity	NPC470822
0.7612	Intermediate Similarity	NPC254698
0.7407	Intermediate Similarity	NPC39818
0.7324	Intermediate Similarity	NPC162417
0.7324	Intermediate Similarity	NPC316104
0.7192	Intermediate Similarity	NPC207554
0.7185	Intermediate Similarity	NPC291962
0.7185	Intermediate Similarity	NPC177684
0.7183	Intermediate Similarity	NPC207428
0.7143	Intermediate Similarity	NPC470301
0.7143	Intermediate Similarity	NPC471164
0.7132	Intermediate Similarity	NPC112373
0.7132	Intermediate Similarity	NPC258531
0.7132	Intermediate Similarity	NPC161956
0.7092	Intermediate Similarity	NPC209389
0.708	Intermediate Similarity	NPC257490
0.7055	Intermediate Similarity	NPC122553
0.7034	Intermediate Similarity	NPC300299
0.7027	Intermediate Similarity	NPC471574
0.7007	Intermediate Similarity	NPC469560
0.7007	Intermediate Similarity	NPC279385
0.7007	Intermediate Similarity	NPC179605
0.6992	Remote Similarity	NPC57051
0.6962	Remote Similarity	NPC143457
0.6959	Remote Similarity	NPC315051
0.6957	Remote Similarity	NPC103292
0.6954	Remote Similarity	NPC470824
0.6918	Remote Similarity	NPC242116
0.6905	Remote Similarity	NPC75496
0.6887	Remote Similarity	NPC136002
0.6879	Remote Similarity	NPC29285
0.6875	Remote Similarity	NPC328270
0.6871	Remote Similarity	NPC471123
0.6828	Remote Similarity	NPC40364
0.6821	Remote Similarity	NPC277157
0.6812	Remote Similarity	NPC226143
0.6806	Remote Similarity	NPC280807
0.6806	Remote Similarity	NPC314431
0.6797	Remote Similarity	NPC285731
0.6797	Remote Similarity	NPC324445
0.6794	Remote Similarity	NPC172170
0.679	Remote Similarity	NPC114637
0.6786	Remote Similarity	NPC268534
0.6779	Remote Similarity	NPC83214
0.6736	Remote Similarity	NPC150863
0.6708	Remote Similarity	NPC286871
0.6708	Remote Similarity	NPC176983
0.6689	Remote Similarity	NPC301760
0.6689	Remote Similarity	NPC2823
0.6667	Remote Similarity	NPC473329
0.6667	Remote Similarity	NPC65408
0.6667	Remote Similarity	NPC55529
0.6646	Remote Similarity	NPC295021
0.6623	Remote Similarity	NPC130251
0.6601	Remote Similarity	NPC478040
0.66	Remote Similarity	NPC287358
0.6597	Remote Similarity	NPC322433
0.6589	Remote Similarity	NPC326792
0.6587	Remote Similarity	NPC13367
0.6582	Remote Similarity	NPC117032
0.6575	Remote Similarity	NPC472245
0.6573	Remote Similarity	NPC192533
0.6536	Remote Similarity	NPC238499
0.6528	Remote Similarity	NPC472244
0.6528	Remote Similarity	NPC470343
0.6525	Remote Similarity	NPC316582
0.6522	Remote Similarity	NPC104345
0.6522	Remote Similarity	NPC113946
0.6522	Remote Similarity	NPC477887
0.6519	Remote Similarity	NPC66936
0.6508	Remote Similarity	NPC71140
0.6503	Remote Similarity	NPC472117
0.65	Remote Similarity	NPC228515
0.6497	Remote Similarity	NPC300596
0.6497	Remote Similarity	NPC237649
0.6494	Remote Similarity	NPC469537
0.6488	Remote Similarity	NPC469529
0.6485	Remote Similarity	NPC214960
0.6485	Remote Similarity	NPC279527
0.6467	Remote Similarity	NPC355
0.6467	Remote Similarity	NPC173295
0.6463	Remote Similarity	NPC194562
0.6442	Remote Similarity	NPC472102
0.6442	Remote Similarity	NPC309531
0.6438	Remote Similarity	NPC281094
0.6402	Remote Similarity	NPC472120
0.6402	Remote Similarity	NPC472101
0.64	Remote Similarity	NPC78154
0.64	Remote Similarity	NPC253476
0.6377	Remote Similarity	NPC187036
0.6375	Remote Similarity	NPC122106
0.637	Remote Similarity	NPC250476
0.6364	Remote Similarity	NPC22082
0.6364	Remote Similarity	NPC186284
0.6351	Remote Similarity	NPC477432
0.6341	Remote Similarity	NPC315368
0.6341	Remote Similarity	NPC201424
0.6333	Remote Similarity	NPC130655
0.6327	Remote Similarity	NPC476950
0.6325	Remote Similarity	NPC472106
0.6322	Remote Similarity	NPC245741
0.6316	Remote Similarity	NPC267508
0.6312	Remote Similarity	NPC31651
0.6312	Remote Similarity	NPC243756
0.6303	Remote Similarity	NPC194881
0.6299	Remote Similarity	NPC473661
0.6296	Remote Similarity	NPC20322
0.6294	Remote Similarity	NPC475594
0.6286	Remote Similarity	NPC282103
0.6282	Remote Similarity	NPC308197
0.6273	Remote Similarity	NPC285381
0.6266	Remote Similarity	NPC146370
0.6266	Remote Similarity	NPC478039
0.6258	Remote Similarity	NPC43477
0.6257	Remote Similarity	NPC475607
0.625	Remote Similarity	NPC282092
0.625	Remote Similarity	NPC164802
0.6242	Remote Similarity	NPC314186
0.6232	Remote Similarity	NPC181390
0.6229	Remote Similarity	NPC477003
0.6228	Remote Similarity	NPC471130
0.6228	Remote Similarity	NPC42372
0.6221	Remote Similarity	NPC474081
0.622	Remote Similarity	NPC61013
0.622	Remote Similarity	NPC123241
0.622	Remote Similarity	NPC222029
0.6216	Remote Similarity	NPC307437
0.6216	Remote Similarity	NPC58827
0.6216	Remote Similarity	NPC72473
0.6213	Remote Similarity	NPC471943
0.6213	Remote Similarity	NPC472118
0.6211	Remote Similarity	NPC154602
0.6209	Remote Similarity	NPC325599
0.6205	Remote Similarity	NPC88970
0.6205	Remote Similarity	NPC476231
0.6203	Remote Similarity	NPC472242
0.6202	Remote Similarity	NPC256452
0.62	Remote Similarity	NPC316746
0.62	Remote Similarity	NPC231382
0.62	Remote Similarity	NPC314098
0.6199	Remote Similarity	NPC293216
0.6199	Remote Similarity	NPC470548
0.6194	Remote Similarity	NPC275467
0.6194	Remote Similarity	NPC38262
0.6194	Remote Similarity	NPC472243
0.619	Remote Similarity	NPC56233
0.619	Remote Similarity	NPC474926
0.6185	Remote Similarity	NPC475094
0.6182	Remote Similarity	NPC193410
0.6182	Remote Similarity	NPC471122
0.6182	Remote Similarity	NPC276085
0.6178	Remote Similarity	NPC314287
0.6171	Remote Similarity	NPC477159
0.617	Remote Similarity	NPC288232
0.6165	Remote Similarity	NPC291610
0.6164	Remote Similarity	NPC470440
0.6159	Remote Similarity	NPC84317
0.6159	Remote Similarity	NPC469536
0.6154	Remote Similarity	NPC63047
0.6154	Remote Similarity	NPC316202
0.6154	Remote Similarity	NPC475248
0.6145	Remote Similarity	NPC474058
0.6145	Remote Similarity	NPC225319
0.6145	Remote Similarity	NPC248117
0.6143	Remote Similarity	NPC296163
0.614	Remote Similarity	NPC96901
0.614	Remote Similarity	NPC177261
0.6135	Remote Similarity	NPC200214
0.6135	Remote Similarity	NPC478076
0.6131	Remote Similarity	NPC471124
0.6131	Remote Similarity	NPC115232
0.6127	Remote Similarity	NPC64436
0.6125	Remote Similarity	NPC478186
0.6122	Remote Similarity	NPC226794
0.6118	Remote Similarity	NPC65080
0.6118	Remote Similarity	NPC91895
0.6115	Remote Similarity	NPC472241
0.6108	Remote Similarity	NPC214106
0.6108	Remote Similarity	NPC293458
0.6107	Remote Similarity	NPC472258
0.6102	Remote Similarity	NPC133003
0.6099	Remote Similarity	NPC294693
0.6098	Remote Similarity	NPC161827
0.6092	Remote Similarity	NPC474041
0.6092	Remote Similarity	NPC475761
0.609	Remote Similarity	NPC242933
0.6087	Remote Similarity	NPC471957
0.6087	Remote Similarity	NPC242000
0.6084	Remote Similarity	NPC36495
0.6084	Remote Similarity	NPC154478
0.6084	Remote Similarity	NPC192209
0.608	Remote Similarity	NPC470205
0.6071	Remote Similarity	NPC138293
0.6071	Remote Similarity	NPC113056
0.6069	Remote Similarity	NPC151635
0.6057	Remote Similarity	NPC88110
0.6057	Remote Similarity	NPC73994
0.6054	Remote Similarity	NPC283130
0.6054	Remote Similarity	NPC328683
0.6053	Remote Similarity	NPC53044

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 NPC187231 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	729
0.2-0.3	1156
0.3-0.4	1804
0.4-0.5	3532
0.5-0.6	1570
0.6-0.7	195
0.7-0.8	10
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
0.7519	Intermediate Similarity	NPD1175	Approved
0.7381	Intermediate Similarity	NPD1064	Approved
0.7381	Intermediate Similarity	NPD1065	Approved
0.7357	Intermediate Similarity	NPD486	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD441	Approved
0.7234	Intermediate Similarity	NPD4300	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2919	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD2918	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD1344	Phase 2
0.7063	Intermediate Similarity	NPD1920	Approved
0.7063	Intermediate Similarity	NPD1919	Approved
0.705	Intermediate Similarity	NPD1640	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2950	Approved
0.7014	Intermediate Similarity	NPD2949	Approved
0.6957	Remote Similarity	NPD1079	Discontinued
0.6954	Remote Similarity	NPD6017	Discontinued
0.6933	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1410	Phase 1
0.6875	Remote Similarity	NPD1619	Phase 3
0.687	Remote Similarity	NPD1342	Approved
0.6867	Remote Similarity	NPD2365	Approved
0.6866	Remote Similarity	NPD5181	Approved
0.6866	Remote Similarity	NPD5180	Approved
0.6866	Remote Similarity	NPD3387	Approved
0.6866	Remote Similarity	NPD5179	Approved
0.6853	Remote Similarity	NPD1781	Discontinued
0.6835	Remote Similarity	NPD1123	Approved
0.6835	Remote Similarity	NPD1124	Approved
0.6831	Remote Similarity	NPD797	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2820	Phase 3
0.6815	Remote Similarity	NPD7072	Phase 2
0.68	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD708	Approved
0.6781	Remote Similarity	NPD1541	Approved
0.6772	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD5227	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD6566	Discontinued
0.6755	Remote Similarity	NPD6768	Approved
0.6733	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5715	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD3865	Approved
0.671	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.671	Remote Similarity	NPD979	Approved
0.6691	Remote Similarity	NPD1306	Clinical (unspecified phase)
0.669	Remote Similarity	NPD9539	Approved
0.669	Remote Similarity	NPD5131	Approved
0.669	Remote Similarity	NPD9541	Approved
0.6688	Remote Similarity	NPD1524	Phase 1
0.6667	Remote Similarity	NPD5918	Discontinued
0.6667	Remote Similarity	NPD200	Phase 2
0.6667	Remote Similarity	NPD1527	Phase 2
0.6667	Remote Similarity	NPD5993	Phase 1
0.6667	Remote Similarity	NPD2351	Discontinued
0.6667	Remote Similarity	NPD1663	Discontinued
0.6667	Remote Similarity	NPD201	Phase 2
0.6646	Remote Similarity	NPD2790	Discontinued
0.6623	Remote Similarity	NPD5931	Phase 3
0.6623	Remote Similarity	NPD5932	Phase 3
0.6623	Remote Similarity	NPD5933	Phase 3
0.6619	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD4432	Discontinued
0.6597	Remote Similarity	NPD9540	Approved
0.6589	Remote Similarity	NPD479	Approved
0.6582	Remote Similarity	NPD3248	Phase 1
0.6579	Remote Similarity	NPD2093	Discontinued
0.6577	Remote Similarity	NPD679	Approved
0.6562	Remote Similarity	NPD951	Approved
0.6562	Remote Similarity	NPD6395	Phase 2
0.6562	Remote Similarity	NPD6396	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7142	Discontinued
0.6556	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD3482	Approved
0.6513	Remote Similarity	NPD1870	Approved
0.65	Remote Similarity	NPD922	Approved
0.6497	Remote Similarity	NPD4942	Approved
0.649	Remote Similarity	NPD4077	Clinical (unspecified phase)
0.649	Remote Similarity	NPD6342	Discontinued
0.6483	Remote Similarity	NPD3240	Phase 2
0.6478	Remote Similarity	NPD1854	Approved
0.6474	Remote Similarity	NPD1956	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1222	Discontinued
0.6467	Remote Similarity	NPD2331	Discontinued
0.6452	Remote Similarity	NPD4043	Approved
0.6452	Remote Similarity	NPD3481	Approved
0.6452	Remote Similarity	NPD4046	Approved
0.6446	Remote Similarity	NPD2413	Phase 2
0.6442	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD3747	Discontinued
0.6438	Remote Similarity	NPD737	Phase 2
0.6434	Remote Similarity	NPD466	Approved
0.6429	Remote Similarity	NPD2638	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD480	Approved
0.6423	Remote Similarity	NPD181	Approved
0.6414	Remote Similarity	NPD5136	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD813	Approved
0.6412	Remote Similarity	NPD3449	Discontinued
0.6395	Remote Similarity	NPD4549	Discontinued
0.6391	Remote Similarity	NPD156	Phase 3
0.6389	Remote Similarity	NPD519	Approved
0.6389	Remote Similarity	NPD1360	Approved
0.6389	Remote Similarity	NPD3623	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3622	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD742	Approved
0.6382	Remote Similarity	NPD6358	Phase 2
0.637	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3625	Discontinued
0.6364	Remote Similarity	NPD2010	Phase 3
0.6357	Remote Similarity	NPD6069	Approved
0.6357	Remote Similarity	NPD6070	Approved
0.6352	Remote Similarity	NPD5748	Phase 2
0.6343	Remote Similarity	NPD3545	Approved
0.6343	Remote Similarity	NPD3546	Approved
0.634	Remote Similarity	NPD1626	Approved
0.6338	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6329	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD3548	Approved
0.6323	Remote Similarity	NPD6513	Approved
0.6323	Remote Similarity	NPD6512	Approved
0.6319	Remote Similarity	NPD4178	Approved
0.6319	Remote Similarity	NPD4176	Approved
0.6316	Remote Similarity	NPD5840	Discontinued
0.6312	Remote Similarity	NPD1055	Approved
0.6312	Remote Similarity	NPD1057	Approved
0.6296	Remote Similarity	NPD4045	Phase 2
0.6296	Remote Similarity	NPD4114	Approved
0.6296	Remote Similarity	NPD1054	Approved
0.6296	Remote Similarity	NPD4115	Approved
0.6296	Remote Similarity	NPD4042	Phase 2
0.6294	Remote Similarity	NPD2340	Discontinued
0.6289	Remote Similarity	NPD5942	Approved
0.6289	Remote Similarity	NPD5941	Approved
0.6287	Remote Similarity	NPD4645	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD766	Clinical (unspecified phase)
0.6284	Remote Similarity	NPD973	Discontinued
0.6282	Remote Similarity	NPD2129	Approved
0.6282	Remote Similarity	NPD5024	Approved
0.628	Remote Similarity	NPD7599	Phase 2
0.6273	Remote Similarity	NPD2501	Discontinued
0.6265	Remote Similarity	NPD923	Approved
0.626	Remote Similarity	NPD787	Suspended
0.6259	Remote Similarity	NPD2840	Approved
0.6258	Remote Similarity	NPD7105	Phase 1
0.6258	Remote Similarity	NPD4461	Discontinued
0.625	Remote Similarity	NPD477	Phase 1
0.625	Remote Similarity	NPD5258	Approved
0.625	Remote Similarity	NPD5260	Approved
0.6242	Remote Similarity	NPD7600	Phase 2
0.6235	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD7254	Discontinued
0.6226	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD1056	Approved
0.6221	Remote Similarity	NPD7587	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5659	Approved
0.622	Remote Similarity	NPD6018	Approved
0.622	Remote Similarity	NPD5660	Approved
0.622	Remote Similarity	NPD6019	Approved
0.6209	Remote Similarity	NPD1998	Approved
0.6209	Remote Similarity	NPD1883	Approved
0.6204	Remote Similarity	NPD4116	Approved
0.6204	Remote Similarity	NPD1107	Approved
0.6204	Remote Similarity	NPD1108	Approved
0.62	Remote Similarity	NPD2754	Discontinued
0.62	Remote Similarity	NPD1069	Approved
0.62	Remote Similarity	NPD1070	Approved
0.62	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.62	Remote Similarity	NPD6489	Phase 3
0.619	Remote Similarity	NPD1036	Approved
0.6178	Remote Similarity	NPD1625	Approved
0.6178	Remote Similarity	NPD5526	Phase 2
0.6178	Remote Similarity	NPD5527	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5253	Approved
0.6174	Remote Similarity	NPD5442	Approved
0.617	Remote Similarity	NPD1323	Discontinued
0.6168	Remote Similarity	NPD3790	Phase 2
0.6165	Remote Similarity	NPD1419	Approved
0.6165	Remote Similarity	NPD1417	Approved
0.6154	Remote Similarity	NPD569	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD1478	Clinical (unspecified phase)
0.6149	Remote Similarity	NPD2737	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD5992	Approved
0.6144	Remote Similarity	NPD2470	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD2791	Discontinued
0.6144	Remote Similarity	NPD1228	Phase 2
0.6144	Remote Similarity	NPD6318	Clinical (unspecified phase)
0.6143	Remote Similarity	NPD23	Approved
0.6136	Remote Similarity	NPD8241	Phase 2
0.6135	Remote Similarity	NPD2603	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4968	Phase 2
0.6125	Remote Similarity	NPD4969	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD4970	Phase 2
0.6124	Remote Similarity	NPD4988	Discontinued
0.6121	Remote Similarity	NPD8630	Approved
0.6119	Remote Similarity	NPD2244	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD941	Approved
0.6115	Remote Similarity	NPD2999	Approved
0.6115	Remote Similarity	NPD753	Approved
0.6115	Remote Similarity	NPD6639	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