NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	188.06
Volume:	188.159
LogP:	1.641
LogD:	1.445
LogS:	-2.615
# Rotatable Bonds:	1
TPSA:	80.04
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.636
Synthetic Accessibility Score:	2.854
Fsp3:	0.1
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.814
MDCK Permeability:	7.046289283607621e-06
Pgp-inhibitor:	0.001
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.607
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.183
Plasma Protein Binding (PPB):	74.83716583251953%
Volume Distribution (VD):	0.678
Pgp-substrate:	19.982906341552734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.836
CYP1A2-substrate:	0.85
CYP2C19-inhibitor:	0.049
CYP2C19-substrate:	0.045
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.871
CYP2D6-inhibitor:	0.404
CYP2D6-substrate:	0.226
CYP3A4-inhibitor:	0.067
CYP3A4-substrate:	0.125

ADMET: Excretion

Clearance (CL):	11.441
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.141
Drug-inuced Liver Injury (DILI):	0.945
AMES Toxicity:	0.679
Rat Oral Acute Toxicity:	0.939
Maximum Recommended Daily Dose:	0.033
Skin Sensitization:	0.628
Carcinogencity:	0.713
Eye Corrosion:	0.425
Eye Irritation:	0.974
Respiratory Toxicity:	0.983

Download Data

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

Natural Product: NPC166667

Natural Product ID:	NPC166667
*Common Name:**	(-)-(R)-2-(4-Hydroxy-2-Oxoindolin-3-Yl)Acetonitrile
IUPAC Name:	2-[(3R)-4-hydroxy-2-oxo-1,3-dihydroindol-3-yl]acetonitrile
Synonyms:
Standard InCHIKey:	KJLUDHCNWCIINR-ZCFIWIBFSA-N
Standard InCHI:	InChI=1S/C10H8N2O2/c11-5-4-6-9-7(12-10(6)14)2-1-3-8(9)13/h1-3,6,13H,4H2,(H,12,14)/t6-/m1/s1
SMILES:	c1cc2c([C@@H](CC#N)C(=N2)O)c(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2063286
PubChem CID:	60156058
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0001146] Indolines

*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
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11678654]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15787451]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	Roots	Anhui, China	n.a.	PMID[22694318]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31050	Isatis indigotica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	46.0	%	PMID[542417]

☑ 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 NPC166667 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	330
0.1-0.2	2758
0.2-0.3	13120
0.3-0.4	5807
0.4-0.5	15030
0.5-0.6	5081
0.6-0.7	525
0.7-0.8	43
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8681	High Similarity	NPC219383
0.8	Intermediate Similarity	NPC470550
0.7933	Intermediate Similarity	NPC184161
0.7829	Intermediate Similarity	NPC9336
0.7594	Intermediate Similarity	NPC205652
0.7564	Intermediate Similarity	NPC291359
0.7438	Intermediate Similarity	NPC19555
0.7422	Intermediate Similarity	NPC178681
0.7353	Intermediate Similarity	NPC147957
0.7346	Intermediate Similarity	NPC257354
0.7343	Intermediate Similarity	NPC197680
0.7343	Intermediate Similarity	NPC259098
0.7328	Intermediate Similarity	NPC76327
0.7305	Intermediate Similarity	NPC317758
0.7279	Intermediate Similarity	NPC222982
0.717	Intermediate Similarity	NPC469428
0.7169	Intermediate Similarity	NPC168153
0.7152	Intermediate Similarity	NPC474409
0.7143	Intermediate Similarity	NPC39822
0.7143	Intermediate Similarity	NPC72291
0.7107	Intermediate Similarity	NPC477889
0.7105	Intermediate Similarity	NPC470090
0.7099	Intermediate Similarity	NPC256838
0.709	Intermediate Similarity	NPC255721
0.7083	Intermediate Similarity	NPC472331
0.7083	Intermediate Similarity	NPC126515
0.7083	Intermediate Similarity	NPC274002
0.7075	Intermediate Similarity	NPC313466
0.7068	Intermediate Similarity	NPC37584
0.7048	Intermediate Similarity	NPC225381
0.7014	Intermediate Similarity	NPC325013
0.7	Intermediate Similarity	NPC10875
0.7	Intermediate Similarity	NPC10730
0.6912	Remote Similarity	NPC474149
0.6886	Remote Similarity	NPC310894
0.6875	Remote Similarity	NPC28510
0.6867	Remote Similarity	NPC184437
0.6842	Remote Similarity	NPC126637
0.6835	Remote Similarity	NPC118202
0.6821	Remote Similarity	NPC317872
0.6818	Remote Similarity	NPC314113
0.6795	Remote Similarity	NPC323798
0.6786	Remote Similarity	NPC317254
0.6784	Remote Similarity	NPC72980
0.6767	Remote Similarity	NPC178902
0.6763	Remote Similarity	NPC192939
0.6763	Remote Similarity	NPC212535
0.6763	Remote Similarity	NPC311936
0.6763	Remote Similarity	NPC215747
0.6744	Remote Similarity	NPC265383
0.6741	Remote Similarity	NPC231705
0.6731	Remote Similarity	NPC60553
0.6724	Remote Similarity	NPC119579
0.6715	Remote Similarity	NPC258056
0.6707	Remote Similarity	NPC103250
0.6705	Remote Similarity	NPC260118
0.6705	Remote Similarity	NPC46580
0.6687	Remote Similarity	NPC204867
0.6686	Remote Similarity	NPC94943
0.6686	Remote Similarity	NPC28425
0.6667	Remote Similarity	NPC272375
0.6667	Remote Similarity	NPC315829
0.6667	Remote Similarity	NPC301702
0.6667	Remote Similarity	NPC235628
0.6648	Remote Similarity	NPC150308
0.6643	Remote Similarity	NPC264782
0.6642	Remote Similarity	NPC153690
0.6629	Remote Similarity	NPC190007
0.6628	Remote Similarity	NPC477187
0.6627	Remote Similarity	NPC477888
0.6627	Remote Similarity	NPC191863
0.6627	Remote Similarity	NPC133470
0.6627	Remote Similarity	NPC289776
0.6621	Remote Similarity	NPC473050
0.6621	Remote Similarity	NPC473051
0.662	Remote Similarity	NPC82963
0.6617	Remote Similarity	NPC70201
0.661	Remote Similarity	NPC219170
0.661	Remote Similarity	NPC180253
0.66	Remote Similarity	NPC226662
0.6597	Remote Similarity	NPC283760
0.6591	Remote Similarity	NPC107619
0.6582	Remote Similarity	NPC472103
0.6581	Remote Similarity	NPC469828
0.6573	Remote Similarity	NPC311737
0.6573	Remote Similarity	NPC38458
0.6569	Remote Similarity	NPC142297
0.6562	Remote Similarity	NPC161292
0.6561	Remote Similarity	NPC245657
0.6538	Remote Similarity	NPC242209
0.6536	Remote Similarity	NPC112676
0.6536	Remote Similarity	NPC174629
0.6532	Remote Similarity	NPC9475
0.6529	Remote Similarity	NPC288430
0.6522	Remote Similarity	NPC24101
0.6522	Remote Similarity	NPC96224
0.6517	Remote Similarity	NPC69213
0.6507	Remote Similarity	NPC324702
0.6503	Remote Similarity	NPC153042
0.6503	Remote Similarity	NPC474188
0.6503	Remote Similarity	NPC153769
0.65	Remote Similarity	NPC472100
0.65	Remote Similarity	NPC146370
0.6497	Remote Similarity	NPC280853
0.6497	Remote Similarity	NPC276060
0.648	Remote Similarity	NPC22928
0.6479	Remote Similarity	NPC142599
0.6475	Remote Similarity	NPC316052
0.6474	Remote Similarity	NPC225857
0.6464	Remote Similarity	NPC204970
0.6456	Remote Similarity	NPC285016
0.6453	Remote Similarity	NPC477185
0.6452	Remote Similarity	NPC472330
0.6452	Remote Similarity	NPC472329
0.645	Remote Similarity	NPC471178
0.6449	Remote Similarity	NPC44836
0.6448	Remote Similarity	NPC472193
0.6448	Remote Similarity	NPC13880
0.6444	Remote Similarity	NPC296742
0.6443	Remote Similarity	NPC205946
0.6441	Remote Similarity	NPC62069
0.6438	Remote Similarity	NPC160120
0.6438	Remote Similarity	NPC17388
0.6438	Remote Similarity	NPC471308
0.6438	Remote Similarity	NPC53596
0.6438	Remote Similarity	NPC289330
0.6434	Remote Similarity	NPC78154
0.6433	Remote Similarity	NPC126481
0.6433	Remote Similarity	NPC471596
0.6429	Remote Similarity	NPC315214
0.6429	Remote Similarity	NPC47298
0.6419	Remote Similarity	NPC471314
0.6419	Remote Similarity	NPC471315
0.6414	Remote Similarity	NPC5932
0.6413	Remote Similarity	NPC243834
0.6413	Remote Similarity	NPC70956
0.6412	Remote Similarity	NPC476483
0.6412	Remote Similarity	NPC278887
0.6405	Remote Similarity	NPC476687
0.6405	Remote Similarity	NPC476689
0.6405	Remote Similarity	NPC476685
0.64	Remote Similarity	NPC88363
0.64	Remote Similarity	NPC316161
0.6397	Remote Similarity	NPC311660
0.6391	Remote Similarity	NPC32028
0.6391	Remote Similarity	NPC159319
0.6391	Remote Similarity	NPC473057
0.6389	Remote Similarity	NPC224293
0.6387	Remote Similarity	NPC218530
0.6383	Remote Similarity	NPC200836
0.6379	Remote Similarity	NPC288943
0.6374	Remote Similarity	NPC44161
0.637	Remote Similarity	NPC29601
0.6369	Remote Similarity	NPC306366
0.6364	Remote Similarity	NPC328070
0.6354	Remote Similarity	NPC11464
0.6353	Remote Similarity	NPC70172
0.6349	Remote Similarity	NPC14339
0.6347	Remote Similarity	NPC153694
0.6347	Remote Similarity	NPC211525
0.6346	Remote Similarity	NPC64205
0.6346	Remote Similarity	NPC159589
0.6343	Remote Similarity	NPC96890
0.6343	Remote Similarity	NPC283152
0.6343	Remote Similarity	NPC315921
0.6341	Remote Similarity	NPC322283
0.6339	Remote Similarity	NPC203972
0.6339	Remote Similarity	NPC106937
0.6336	Remote Similarity	NPC306074
0.6335	Remote Similarity	NPC471598
0.6333	Remote Similarity	NPC66083
0.6331	Remote Similarity	NPC230942
0.6331	Remote Similarity	NPC59779
0.6331	Remote Similarity	NPC471177
0.6331	Remote Similarity	NPC315498
0.6331	Remote Similarity	NPC475983
0.6331	Remote Similarity	NPC124542
0.6329	Remote Similarity	NPC471594
0.6328	Remote Similarity	NPC155393
0.6327	Remote Similarity	NPC112823
0.6324	Remote Similarity	NPC12221
0.6322	Remote Similarity	NPC95412
0.6322	Remote Similarity	NPC303225
0.6316	Remote Similarity	NPC101372
0.6316	Remote Similarity	NPC8392
0.6316	Remote Similarity	NPC238430
0.6313	Remote Similarity	NPC314002
0.6312	Remote Similarity	NPC226914
0.6306	Remote Similarity	NPC316574
0.6301	Remote Similarity	NPC83241
0.6298	Remote Similarity	NPC128751
0.6298	Remote Similarity	NPC246700
0.6294	Remote Similarity	NPC139506
0.6294	Remote Similarity	NPC292143
0.6292	Remote Similarity	NPC220765
0.6291	Remote Similarity	NPC476249
0.629	Remote Similarity	NPC306376
0.6288	Remote Similarity	NPC271440
0.6284	Remote Similarity	NPC294244
0.6284	Remote Similarity	NPC86966

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 NPC166667 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	226
0.1-0.2	748
0.2-0.3	1038
0.3-0.4	1295
0.4-0.5	3779
0.5-0.6	1819
0.6-0.7	241
0.7-0.8	4
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
0.7829	Intermediate Similarity	NPD5617	Suspended
0.7328	Intermediate Similarity	NPD9507	Approved
0.7025	Intermediate Similarity	NPD950	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD1850	Phase 3
0.7	Intermediate Similarity	NPD2789	Approved
0.697	Remote Similarity	NPD4986	Clinical (unspecified phase)
0.695	Remote Similarity	NPD2212	Approved
0.695	Remote Similarity	NPD2210	Approved
0.6937	Remote Similarity	NPD3296	Phase 1
0.6894	Remote Similarity	NPD2468	Approved
0.6894	Remote Similarity	NPD2469	Approved
0.6875	Remote Similarity	NPD5811	Approved
0.6871	Remote Similarity	NPD5599	Discontinued
0.6821	Remote Similarity	NPD654	Phase 3
0.6809	Remote Similarity	NPD313	Approved
0.6797	Remote Similarity	NPD1169	Approved
0.6786	Remote Similarity	NPD2216	Approved
0.6786	Remote Similarity	NPD9342	Approved
0.6786	Remote Similarity	NPD2215	Approved
0.6752	Remote Similarity	NPD1835	Phase 1
0.6733	Remote Similarity	NPD2322	Discovery
0.6732	Remote Similarity	NPD696	Discontinued
0.6723	Remote Similarity	NPD2843	Phase 2
0.6723	Remote Similarity	NPD2845	Phase 2
0.6667	Remote Similarity	NPD9277	Approved
0.6667	Remote Similarity	NPD75	Approved
0.6629	Remote Similarity	NPD7629	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7630	Phase 3
0.6629	Remote Similarity	NPD7628	Phase 3
0.6603	Remote Similarity	NPD9274	Approved
0.6603	Remote Similarity	NPD9275	Approved
0.6603	Remote Similarity	NPD9276	Approved
0.6603	Remote Similarity	NPD9278	Suspended
0.6587	Remote Similarity	NPD3453	Discontinued
0.6568	Remote Similarity	NPD1921	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD2752	Clinical (unspecified phase)
0.6547	Remote Similarity	NPD9376	Approved
0.6531	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD522	Approved
0.6522	Remote Similarity	NPD681	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD4951	Discontinued
0.6506	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.65	Remote Similarity	NPD308	Approved
0.65	Remote Similarity	NPD3141	Discontinued
0.6485	Remote Similarity	NPD3236	Phase 3
0.6485	Remote Similarity	NPD3237	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1595	Approved
0.6471	Remote Similarity	NPD1594	Phase 3
0.6464	Remote Similarity	NPD5937	Approved
0.6463	Remote Similarity	NPD1162	Approved
0.6458	Remote Similarity	NPD254	Approved
0.6443	Remote Similarity	NPD6320	Approved
0.6442	Remote Similarity	NPD3329	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD5560	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD1685	Approved
0.6429	Remote Similarity	NPD1684	Approved
0.6424	Remote Similarity	NPD1557	Discontinued
0.6424	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD1411	Approved
0.6412	Remote Similarity	NPD1413	Approved
0.6412	Remote Similarity	NPD1414	Approved
0.6412	Remote Similarity	NPD1394	Approved
0.641	Remote Similarity	NPD6636	Phase 3
0.6409	Remote Similarity	NPD6656	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD2229	Approved
0.6408	Remote Similarity	NPD2228	Approved
0.6408	Remote Similarity	NPD2234	Approved
0.6404	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.64	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.64	Remote Similarity	NPD7479	Phase 2
0.6397	Remote Similarity	NPD1542	Approved
0.6395	Remote Similarity	NPD1980	Approved
0.6395	Remote Similarity	NPD1983	Approved
0.6395	Remote Similarity	NPD3143	Discontinued
0.6395	Remote Similarity	NPD1981	Approved
0.6392	Remote Similarity	NPD6809	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD7083	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2672	Discontinued
0.6386	Remote Similarity	NPD3778	Approved
0.6386	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD1361	Discontinued
0.6377	Remote Similarity	NPD1444	Approved
0.6377	Remote Similarity	NPD1445	Approved
0.6375	Remote Similarity	NPD1196	Approved
0.6375	Remote Similarity	NPD7066	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD5819	Phase 2
0.6369	Remote Similarity	NPD5565	Discontinued
0.6364	Remote Similarity	NPD7477	Discontinued
0.6358	Remote Similarity	NPD1543	Discontinued
0.6347	Remote Similarity	NPD3812	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD471	Approved
0.6345	Remote Similarity	NPD9247	Phase 3
0.6343	Remote Similarity	NPD9273	Approved
0.6339	Remote Similarity	NPD802	Phase 2
0.6338	Remote Similarity	NPD181	Approved
0.6335	Remote Similarity	NPD2916	Discontinued
0.6333	Remote Similarity	NPD6325	Discontinued
0.6331	Remote Similarity	NPD1743	Approved
0.6331	Remote Similarity	NPD1742	Approved
0.6331	Remote Similarity	NPD19	Approved
0.6324	Remote Similarity	NPD1540	Approved
0.6316	Remote Similarity	NPD7129	Suspended
0.6316	Remote Similarity	NPD4895	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD1195	Approved
0.6307	Remote Similarity	NPD1716	Phase 3
0.6306	Remote Similarity	NPD9279	Approved
0.6303	Remote Similarity	NPD4003	Phase 3
0.6303	Remote Similarity	NPD814	Clinical (unspecified phase)
0.6301	Remote Similarity	NPD1759	Phase 1
0.6301	Remote Similarity	NPD5304	Approved
0.6301	Remote Similarity	NPD5303	Approved
0.6296	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD2802	Phase 3
0.6288	Remote Similarity	NPD845	Approved
0.628	Remote Similarity	NPD1159	Approved
0.6271	Remote Similarity	NPD2169	Clinical (unspecified phase)
0.627	Remote Similarity	NPD8249	Clinical (unspecified phase)
0.6269	Remote Similarity	NPD288	Approved
0.6267	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD204	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD2674	Phase 3
0.6257	Remote Similarity	NPD4796	Discontinued
0.6257	Remote Similarity	NPD926	Approved
0.6257	Remote Similarity	NPD925	Approved
0.6257	Remote Similarity	NPD1615	Approved
0.625	Remote Similarity	NPD9614	Approved
0.625	Remote Similarity	NPD6159	Phase 2
0.625	Remote Similarity	NPD289	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9618	Approved
0.6241	Remote Similarity	NPD1792	Phase 2
0.6237	Remote Similarity	NPD4605	Approved
0.6237	Remote Similarity	NPD4604	Approved
0.6236	Remote Similarity	NPD4204	Approved
0.6236	Remote Similarity	NPD4203	Approved
0.6234	Remote Similarity	NPD4275	Approved
0.6234	Remote Similarity	NPD4274	Approved
0.6234	Remote Similarity	NPD2372	Approved
0.6234	Remote Similarity	NPD3720	Discontinued
0.6233	Remote Similarity	NPD1758	Phase 1
0.6232	Remote Similarity	NPD9610	Approved
0.6232	Remote Similarity	NPD9608	Approved
0.622	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD1592	Phase 3
0.6209	Remote Similarity	NPD1712	Approved
0.6207	Remote Similarity	NPD3975	Discontinued
0.6207	Remote Similarity	NPD2622	Approved
0.6205	Remote Similarity	NPD2188	Approved
0.6203	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6201	Remote Similarity	NPD2744	Phase 1
0.6201	Remote Similarity	NPD4012	Approved
0.62	Remote Similarity	NPD3070	Discontinued
0.62	Remote Similarity	NPD964	Approved
0.6199	Remote Similarity	NPD955	Approved
0.6194	Remote Similarity	NPD3145	Approved
0.6194	Remote Similarity	NPD3144	Approved
0.619	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6188	Remote Similarity	NPD6789	Approved
0.6185	Remote Similarity	NPD3983	Phase 3
0.6185	Remote Similarity	NPD3984	Clinical (unspecified phase)
0.618	Remote Similarity	NPD1717	Clinical (unspecified phase)
0.618	Remote Similarity	NPD2167	Clinical (unspecified phase)
0.618	Remote Similarity	NPD2168	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD2688	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD1236	Phase 3
0.6164	Remote Similarity	NPD5788	Clinical (unspecified phase)
0.6159	Remote Similarity	NPD3359	Clinical (unspecified phase)
0.6158	Remote Similarity	NPD3793	Phase 3
0.6158	Remote Similarity	NPD6975	Discontinued
0.6154	Remote Similarity	NPD840	Approved
0.6154	Remote Similarity	NPD3119	Phase 1
0.6154	Remote Similarity	NPD2383	Phase 1
0.6154	Remote Similarity	NPD839	Approved
0.6154	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD1861	Discovery
0.6154	Remote Similarity	NPD3120	Approved
0.6149	Remote Similarity	NPD1293	Approved
0.6145	Remote Similarity	NPD711	Discontinued
0.6145	Remote Similarity	NPD3037	Phase 1
0.6144	Remote Similarity	NPD7451	Discontinued
0.6138	Remote Similarity	NPD1791	Approved
0.6138	Remote Similarity	NPD5631	Phase 3
0.6138	Remote Similarity	NPD1793	Approved
0.6136	Remote Similarity	NPD5602	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD3136	Phase 2
0.6125	Remote Similarity	NPD2161	Phase 2
0.6125	Remote Similarity	NPD3391	Approved
0.6125	Remote Similarity	NPD1632	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD6522	Clinical (unspecified phase)
0.612	Remote Similarity	NPD1339	Discontinued
0.6118	Remote Similarity	NPD9587	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6283	Phase 2
0.6118	Remote Similarity	NPD1036	Approved
0.6117	Remote Similarity	NPD2727	Phase 2
0.6115	Remote Similarity	NPD6346	Approved
0.6115	Remote Similarity	NPD1106	Discontinued
0.6114	Remote Similarity	NPD4083	Discontinued
0.6111	Remote Similarity	NPD1381	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD1764	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