NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	289.09
Volume:	292.569
LogP:	2.034
LogD:	1.276
LogS:	-3.47
# Rotatable Bonds:	2
TPSA:	75.18
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	2.738
Fsp3:	0.059
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:	-4.861
MDCK Permeability:	2.0955458239768632e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.25
Plasma Protein Binding (PPB):	94.053466796875%
Volume Distribution (VD):	0.678
Pgp-substrate:	1.6670153141021729%

ADMET: Metabolism

CYP1A2-inhibitor:	0.967
CYP1A2-substrate:	0.337
CYP2C19-inhibitor:	0.72
CYP2C19-substrate:	0.181
CYP2C9-inhibitor:	0.759
CYP2C9-substrate:	0.955
CYP2D6-inhibitor:	0.209
CYP2D6-substrate:	0.264
CYP3A4-inhibitor:	0.609
CYP3A4-substrate:	0.295

ADMET: Excretion

Clearance (CL):	1.402
Half-life (T1/2):	0.448

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.94
Drug-inuced Liver Injury (DILI):	0.979
AMES Toxicity:	0.676
Rat Oral Acute Toxicity:	0.558
Maximum Recommended Daily Dose:	0.532
Skin Sensitization:	0.585
Carcinogencity:	0.425
Eye Corrosion:	0.003
Eye Irritation:	0.037
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: NPC477889

Natural Product ID:	NPC477889
*Common Name:**	3-[(E)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-cinnolin-4-one
IUPAC Name:	3-[(E)-(2-oxo-1H-indol-3-ylidene)methyl]-1H-cinnolin-4-one
Synonyms:
Standard InCHIKey:	VOMIZFVKXYVQPM-FMIVXFBMSA-N
Standard InCHI:	InChI=1S/C17H11N3O2/c21-16-11-6-2-4-8-14(11)19-20-15(16)9-12-10-5-1-3-7-13(10)18-17(12)22/h1-9H,(H,18,22)(H,19,21)/b12-9+
SMILES:	C1=CC=C2C(=C1)/C(=C\C3=NNC4=CC=CC=C4C3=O)/C(=O)N2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	136224179
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0004788] Diazanaphthalenes [CHEMONTID:0004789] Benzodiazines [CHEMONTID:0000206] Cinnolines

*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
NPO6453	Schizophyllum commune	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24262004]
NPO6453	Schizophyllum commune	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25951057]
NPO6453	Schizophyllum commune	Species	Schizophyllaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	100000	nM	PMID[24262004]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	100000	nM	PMID[24262004]

☑ 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 NPC477889 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	472
0.1-0.2	3931
0.2-0.3	13422
0.3-0.4	9046
0.4-0.5	12059
0.5-0.6	3305
0.6-0.7	442
0.7-0.8	17
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9161	High Similarity	NPC477888
0.8289	Intermediate Similarity	NPC477890
0.7619	Intermediate Similarity	NPC44161
0.7514	Intermediate Similarity	NPC472193
0.7429	Intermediate Similarity	NPC477891
0.7371	Intermediate Similarity	NPC478032
0.736	Intermediate Similarity	NPC314573
0.7312	Intermediate Similarity	NPC60553
0.7202	Intermediate Similarity	NPC26850
0.7168	Intermediate Similarity	NPC473764
0.7168	Intermediate Similarity	NPC314940
0.7143	Intermediate Similarity	NPC147957
0.7135	Intermediate Similarity	NPC144114
0.7107	Intermediate Similarity	NPC166667
0.7086	Intermediate Similarity	NPC208060
0.7086	Intermediate Similarity	NPC474409
0.7029	Intermediate Similarity	NPC252590
0.7025	Intermediate Similarity	NPC184437
0.7017	Intermediate Similarity	NPC42591
0.7006	Intermediate Similarity	NPC288943
0.6977	Remote Similarity	NPC79911
0.6977	Remote Similarity	NPC224632
0.6966	Remote Similarity	NPC283152
0.6951	Remote Similarity	NPC470404
0.6951	Remote Similarity	NPC470394
0.6951	Remote Similarity	NPC470403
0.6946	Remote Similarity	NPC288445
0.6923	Remote Similarity	NPC26872
0.6919	Remote Similarity	NPC120798
0.6902	Remote Similarity	NPC230805
0.6867	Remote Similarity	NPC470395
0.6865	Remote Similarity	NPC144381
0.6839	Remote Similarity	NPC118511
0.6829	Remote Similarity	NPC470090
0.6818	Remote Similarity	NPC278874
0.6786	Remote Similarity	NPC257142
0.6782	Remote Similarity	NPC177404
0.6776	Remote Similarity	NPC190007
0.6768	Remote Similarity	NPC314113
0.6765	Remote Similarity	NPC153769
0.6765	Remote Similarity	NPC184161
0.6757	Remote Similarity	NPC66083
0.6742	Remote Similarity	NPC476688
0.6742	Remote Similarity	NPC476686
0.6742	Remote Similarity	NPC105758
0.674	Remote Similarity	NPC72980
0.674	Remote Similarity	NPC88363
0.6739	Remote Similarity	NPC94943
0.6737	Remote Similarity	NPC474188
0.6735	Remote Similarity	NPC477111
0.6726	Remote Similarity	NPC161292
0.6725	Remote Similarity	NPC36168
0.6721	Remote Similarity	NPC212535
0.6718	Remote Similarity	NPC477113
0.6709	Remote Similarity	NPC259098
0.6709	Remote Similarity	NPC197680
0.6702	Remote Similarity	NPC192315
0.6702	Remote Similarity	NPC324149
0.6686	Remote Similarity	NPC133470
0.6686	Remote Similarity	NPC289776
0.6686	Remote Similarity	NPC191863
0.6685	Remote Similarity	NPC164664
0.6685	Remote Similarity	NPC62069
0.6667	Remote Similarity	NPC312872
0.6667	Remote Similarity	NPC280853
0.6667	Remote Similarity	NPC470500
0.6667	Remote Similarity	NPC95898
0.6667	Remote Similarity	NPC476167
0.6667	Remote Similarity	NPC18487
0.6667	Remote Similarity	NPC103250
0.6667	Remote Similarity	NPC284348
0.6667	Remote Similarity	NPC230403
0.6649	Remote Similarity	NPC77555
0.6627	Remote Similarity	NPC285016
0.6627	Remote Similarity	NPC245657
0.6614	Remote Similarity	NPC99666
0.6613	Remote Similarity	NPC204385
0.661	Remote Similarity	NPC471178
0.6606	Remote Similarity	NPC471596
0.6597	Remote Similarity	NPC178681
0.6591	Remote Similarity	NPC471177
0.6591	Remote Similarity	NPC59779
0.6591	Remote Similarity	NPC124542
0.6584	Remote Similarity	NPC313466
0.6584	Remote Similarity	NPC477110
0.6583	Remote Similarity	NPC5145
0.6578	Remote Similarity	NPC46580
0.6576	Remote Similarity	NPC206201
0.6576	Remote Similarity	NPC314394
0.6575	Remote Similarity	NPC303225
0.6571	Remote Similarity	NPC291359
0.6562	Remote Similarity	NPC267928
0.6562	Remote Similarity	NPC153042
0.6557	Remote Similarity	NPC42979
0.6554	Remote Similarity	NPC159319
0.6554	Remote Similarity	NPC255721
0.6552	Remote Similarity	NPC141353
0.6548	Remote Similarity	NPC304183
0.6546	Remote Similarity	NPC249040
0.6543	Remote Similarity	NPC246700
0.6543	Remote Similarity	NPC110741
0.6543	Remote Similarity	NPC128751
0.6538	Remote Similarity	NPC224764
0.6534	Remote Similarity	NPC25899
0.6531	Remote Similarity	NPC200836
0.6531	Remote Similarity	NPC37584
0.6531	Remote Similarity	NPC223427
0.6509	Remote Similarity	NPC471598
0.6508	Remote Similarity	NPC106833
0.6508	Remote Similarity	NPC471593
0.6508	Remote Similarity	NPC469497
0.65	Remote Similarity	NPC126481
0.6497	Remote Similarity	NPC48192
0.6497	Remote Similarity	NPC315214
0.6497	Remote Similarity	NPC47298
0.6485	Remote Similarity	NPC126637
0.648	Remote Similarity	NPC470678
0.648	Remote Similarity	NPC19555
0.6477	Remote Similarity	NPC243834
0.6477	Remote Similarity	NPC70956
0.6474	Remote Similarity	NPC219383
0.6471	Remote Similarity	NPC314002
0.6471	Remote Similarity	NPC82963
0.6467	Remote Similarity	NPC472168
0.6464	Remote Similarity	NPC158129
0.6461	Remote Similarity	NPC32028
0.6461	Remote Similarity	NPC97367
0.6458	Remote Similarity	NPC276517
0.6457	Remote Similarity	NPC10730
0.6457	Remote Similarity	NPC10875
0.6452	Remote Similarity	NPC220765
0.6448	Remote Similarity	NPC150048
0.6448	Remote Similarity	NPC203754
0.6447	Remote Similarity	NPC53144
0.6447	Remote Similarity	NPC470550
0.6441	Remote Similarity	NPC235628
0.6441	Remote Similarity	NPC322644
0.6436	Remote Similarity	NPC294620
0.6432	Remote Similarity	NPC249662
0.6429	Remote Similarity	NPC471294
0.6429	Remote Similarity	NPC38458
0.6429	Remote Similarity	NPC311737
0.6425	Remote Similarity	NPC194967
0.6422	Remote Similarity	NPC62995
0.6421	Remote Similarity	NPC3715
0.642	Remote Similarity	NPC116573
0.6419	Remote Similarity	NPC76327
0.6417	Remote Similarity	NPC204717
0.6417	Remote Similarity	NPC320394
0.6414	Remote Similarity	NPC475070
0.6413	Remote Similarity	NPC96890
0.6413	Remote Similarity	NPC184964
0.641	Remote Similarity	NPC128823
0.6409	Remote Similarity	NPC288430
0.6407	Remote Similarity	NPC471594
0.6406	Remote Similarity	NPC79293
0.6406	Remote Similarity	NPC279401
0.6406	Remote Similarity	NPC329541
0.6402	Remote Similarity	NPC254762
0.64	Remote Similarity	NPC18348
0.64	Remote Similarity	NPC9336
0.64	Remote Similarity	NPC470931
0.6396	Remote Similarity	NPC291535
0.6396	Remote Similarity	NPC475085
0.6396	Remote Similarity	NPC475112
0.6396	Remote Similarity	NPC211813
0.6384	Remote Similarity	NPC84508
0.6378	Remote Similarity	NPC19872
0.6376	Remote Similarity	NPC153690
0.6369	Remote Similarity	NPC476118
0.6368	Remote Similarity	NPC469589
0.6368	Remote Similarity	NPC209769
0.6364	Remote Similarity	NPC475774
0.6364	Remote Similarity	NPC243058
0.6359	Remote Similarity	NPC306376
0.6354	Remote Similarity	NPC114335
0.6354	Remote Similarity	NPC141915
0.6354	Remote Similarity	NPC280964
0.635	Remote Similarity	NPC283117
0.6349	Remote Similarity	NPC171171
0.6349	Remote Similarity	NPC194040
0.6348	Remote Similarity	NPC131718
0.6345	Remote Similarity	NPC470586
0.6344	Remote Similarity	NPC478023
0.6344	Remote Similarity	NPC222592
0.6344	Remote Similarity	NPC168486
0.6341	Remote Similarity	NPC470799
0.6341	Remote Similarity	NPC8022
0.634	Remote Similarity	NPC242209
0.6339	Remote Similarity	NPC259545
0.6337	Remote Similarity	NPC254798
0.633	Remote Similarity	NPC203635
0.6329	Remote Similarity	NPC473179
0.6324	Remote Similarity	NPC219848
0.6324	Remote Similarity	NPC250448
0.6319	Remote Similarity	NPC257354
0.6318	Remote Similarity	NPC287208
0.6313	Remote Similarity	NPC476231
0.6313	Remote Similarity	NPC135887
0.6313	Remote Similarity	NPC199277

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 NPC477889 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	281
0.1-0.2	752
0.2-0.3	988
0.3-0.4	1135
0.4-0.5	3846
0.5-0.6	1912
0.6-0.7	223
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
0.7937	Intermediate Similarity	NPD948	Phase 3
0.7765	Intermediate Similarity	NPD6159	Phase 2
0.7619	Intermediate Similarity	NPD1921	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD3342	Phase 2
0.7429	Intermediate Similarity	NPD3037	Phase 1
0.7348	Intermediate Similarity	NPD3963	Phase 1
0.7283	Intermediate Similarity	NPD677	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD8286	Phase 2
0.7119	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD2882	Phase 1
0.7066	Intermediate Similarity	NPD6158	Phase 2
0.7066	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD9690	Approved
0.6966	Remote Similarity	NPD3503	Approved
0.6966	Remote Similarity	NPD3504	Approved
0.6961	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6902	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD3390	Phase 2
0.6842	Remote Similarity	NPD3837	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2789	Approved
0.6831	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD1924	Approved
0.6821	Remote Similarity	NPD9705	Discontinued
0.6821	Remote Similarity	NPD112	Approved
0.6818	Remote Similarity	NPD5945	Phase 1
0.6818	Remote Similarity	NPD5944	Phase 1
0.6791	Remote Similarity	NPD4941	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1193	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD6290	Phase 2
0.6755	Remote Similarity	NPD9695	Approved
0.6754	Remote Similarity	NPD2176	Approved
0.6754	Remote Similarity	NPD2175	Phase 3
0.6754	Remote Similarity	NPD2177	Approved
0.6747	Remote Similarity	NPD5819	Phase 2
0.6724	Remote Similarity	NPD5599	Discontinued
0.6717	Remote Similarity	NPD5939	Approved
0.6717	Remote Similarity	NPD5936	Approved
0.6705	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD4909	Approved
0.6702	Remote Similarity	NPD3404	Approved
0.6667	Remote Similarity	NPD2383	Phase 1
0.6667	Remote Similarity	NPD6492	Phase 2
0.6667	Remote Similarity	NPD9706	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD5849	Approved
0.6633	Remote Similarity	NPD4502	Phase 2
0.6632	Remote Similarity	NPD6590	Discontinued
0.6631	Remote Similarity	NPD408	Approved
0.6629	Remote Similarity	NPD3241	Phase 2
0.6597	Remote Similarity	NPD5512	Phase 3
0.6587	Remote Similarity	NPD1592	Phase 3
0.6579	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6576	Remote Similarity	NPD4203	Approved
0.6576	Remote Similarity	NPD4204	Approved
0.6562	Remote Similarity	NPD7948	Phase 1
0.6559	Remote Similarity	NPD2762	Phase 2
0.6557	Remote Similarity	NPD3417	Phase 1
0.6548	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6491	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4400	Approved
0.6543	Remote Similarity	NPD2792	Approved
0.6541	Remote Similarity	NPD2391	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5811	Approved
0.6528	Remote Similarity	NPD712	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2727	Phase 2
0.6528	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.6526	Remote Similarity	NPD9689	Approved
0.652	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6515	Remote Similarity	NPD7222	Phase 2
0.6497	Remote Similarity	NPD1685	Approved
0.6497	Remote Similarity	NPD1684	Approved
0.6494	Remote Similarity	NPD5617	Suspended
0.6491	Remote Similarity	NPD1526	Phase 2
0.6484	Remote Similarity	NPD5065	Approved
0.6482	Remote Similarity	NPD2916	Discontinued
0.648	Remote Similarity	NPD3931	Approved
0.648	Remote Similarity	NPD3928	Approved
0.6477	Remote Similarity	NPD3261	Phase 1
0.6477	Remote Similarity	NPD5255	Approved
0.6465	Remote Similarity	NPD3842	Clinical (unspecified phase)
0.6461	Remote Similarity	NPD861	Approved
0.6461	Remote Similarity	NPD862	Approved
0.6461	Remote Similarity	NPD863	Approved
0.6458	Remote Similarity	NPD6861	Clinical (unspecified phase)
0.645	Remote Similarity	NPD3525	Discontinued
0.6448	Remote Similarity	NPD2380	Approved
0.6448	Remote Similarity	NPD2381	Approved
0.6448	Remote Similarity	NPD2382	Approved
0.6446	Remote Similarity	NPD1169	Approved
0.6444	Remote Similarity	NPD2781	Approved
0.6436	Remote Similarity	NPD5097	Phase 2
0.6432	Remote Similarity	NPD6452	Discontinued
0.6429	Remote Similarity	NPD3224	Phase 2
0.6425	Remote Similarity	NPD2782	Approved
0.6425	Remote Similarity	NPD2780	Approved
0.6422	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD9507	Approved
0.6412	Remote Similarity	NPD5595	Clinical (unspecified phase)
0.641	Remote Similarity	NPD8396	Approved
0.641	Remote Similarity	NPD8395	Approved
0.641	Remote Similarity	NPD1499	Phase 3
0.6408	Remote Similarity	NPD3875	Discontinued
0.6402	Remote Similarity	NPD4951	Discontinued
0.6396	Remote Similarity	NPD5495	Phase 2
0.6396	Remote Similarity	NPD6975	Discontinued
0.6392	Remote Similarity	NPD7081	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD6988	Phase 1
0.6389	Remote Similarity	NPD425	Approved
0.6389	Remote Similarity	NPD424	Approved
0.6387	Remote Similarity	NPD5081	Phase 1
0.6387	Remote Similarity	NPD5082	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD5416	Discontinued
0.6384	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD604	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD6150	Discontinued
0.6382	Remote Similarity	NPD5530	Phase 1
0.6382	Remote Similarity	NPD4305	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD7603	Discontinued
0.6379	Remote Similarity	NPD950	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6140	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD5140	Approved
0.6369	Remote Similarity	NPD5138	Approved
0.6368	Remote Similarity	NPD6965	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD3778	Approved
0.6364	Remote Similarity	NPD980	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6991	Approved
0.6364	Remote Similarity	NPD5596	Phase 2
0.6355	Remote Similarity	NPD4927	Discontinued
0.6354	Remote Similarity	NPD6569	Phase 2
0.635	Remote Similarity	NPD7452	Approved
0.635	Remote Similarity	NPD3930	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7453	Approved
0.6348	Remote Similarity	NPD1741	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD7726	Phase 1
0.634	Remote Similarity	NPD6550	Discontinued
0.6339	Remote Similarity	NPD6607	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD1213	Phase 3
0.6335	Remote Similarity	NPD5316	Approved
0.6329	Remote Similarity	NPD4312	Approved
0.6327	Remote Similarity	NPD9688	Approved
0.6327	Remote Similarity	NPD9687	Approved
0.6316	Remote Similarity	NPD3813	Approved
0.6316	Remote Similarity	NPD6736	Discontinued
0.6313	Remote Similarity	NPD4355	Clinical (unspecified phase)
0.631	Remote Similarity	NPD7867	Phase 1
0.6308	Remote Similarity	NPD2476	Clinical (unspecified phase)
0.6308	Remote Similarity	NPD6162	Approved
0.6308	Remote Similarity	NPD6161	Approved
0.6307	Remote Similarity	NPD3296	Phase 1
0.6299	Remote Similarity	NPD9342	Approved
0.6298	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6293	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD6283	Phase 2
0.629	Remote Similarity	NPD3920	Phase 2
0.628	Remote Similarity	NPD2322	Discovery
0.6278	Remote Similarity	NPD3986	Discontinued
0.6278	Remote Similarity	NPD444	Approved
0.6275	Remote Similarity	NPD3330	Phase 1
0.6263	Remote Similarity	NPD4511	Phase 1
0.6257	Remote Similarity	NPD9398	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD6524	Clinical (unspecified phase)
0.6257	Remote Similarity	NPD3327	Approved
0.6256	Remote Similarity	NPD6594	Discontinued
0.625	Remote Similarity	NPD32	Approved
0.625	Remote Similarity	NPD4035	Approved
0.625	Remote Similarity	NPD4036	Approved
0.625	Remote Similarity	NPD31	Approved
0.625	Remote Similarity	NPD4122	Approved
0.625	Remote Similarity	NPD4033	Approved
0.625	Remote Similarity	NPD5078	Clinical (unspecified phase)
0.625	Remote Similarity	NPD4037	Approved
0.625	Remote Similarity	NPD4034	Approved
0.625	Remote Similarity	NPD4038	Approved
0.625	Remote Similarity	NPD4039	Approved
0.6244	Remote Similarity	NPD2616	Phase 3
0.6244	Remote Similarity	NPD2151	Approved
0.6244	Remote Similarity	NPD2615	Phase 3
0.6243	Remote Similarity	NPD925	Approved
0.6243	Remote Similarity	NPD926	Approved
0.6242	Remote Similarity	NPD2210	Approved
0.6242	Remote Similarity	NPD2212	Approved
0.6238	Remote Similarity	NPD3234	Phase 3
0.6238	Remote Similarity	NPD7672	Approved
0.6238	Remote Similarity	NPD7671	Approved
0.6238	Remote Similarity	NPD3233	Phase 2
0.6236	Remote Similarity	NPD9383	Approved
0.6236	Remote Similarity	NPD9382	Approved
0.6234	Remote Similarity	NPD5631	Phase 3
0.6233	Remote Similarity	NPD5151	Clinical (unspecified phase)
0.6231	Remote Similarity	NPD6208	Discontinued
0.623	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6224	Remote Similarity	NPD6769	Clinical (unspecified phase)
0.6223	Remote Similarity	NPD7414	Clinical (unspecified phase)
0.6221	Remote Similarity	NPD1835	Phase 1
0.6219	Remote Similarity	NPD3003	Approved
0.6214	Remote Similarity	NPD7538	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