NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	296.18
Volume:	336.488
LogP:	5.683
LogD:	4.325
LogS:	-5.723
# Rotatable Bonds:	4
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	2.959
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.565
MDCK Permeability:	2.279094587720465e-05
Pgp-inhibitor:	0.85
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.026
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.129
Plasma Protein Binding (PPB):	87.48995208740234%
Volume Distribution (VD):	2.02
Pgp-substrate:	9.779397010803223%

ADMET: Metabolism

CYP1A2-inhibitor:	0.758
CYP1A2-substrate:	0.143
CYP2C19-inhibitor:	0.855
CYP2C19-substrate:	0.227
CYP2C9-inhibitor:	0.84
CYP2C9-substrate:	0.761
CYP2D6-inhibitor:	0.102
CYP2D6-substrate:	0.122
CYP3A4-inhibitor:	0.349
CYP3A4-substrate:	0.222

ADMET: Excretion

Clearance (CL):	7.202
Half-life (T1/2):	0.029

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.939
Drug-inuced Liver Injury (DILI):	0.164
AMES Toxicity:	0.237
Rat Oral Acute Toxicity:	0.422
Maximum Recommended Daily Dose:	0.027
Skin Sensitization:	0.095
Carcinogencity:	0.462
Eye Corrosion:	0.003
Eye Irritation:	0.076
Respiratory Toxicity:	0.837

Download Data

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

Natural Product: NPC59661

Natural Product ID:	NPC59661
*Common Name:**	Varacin
IUPAC Name:	2-(6,7-dimethoxy-1,2,3,4,5-benzopentathiepin-9-yl)ethanamine
Synonyms:	Varacin
Standard InCHIKey:	HIKCOAGMCNIBMP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H13NO2S5/c1-12-7-5-6(3-4-11)9-10(8(7)13-2)15-17-18-16-14-9/h5H,3-4,11H2,1-2H3
SMILES:	COc1cc(CCN)c2c(c1OC)SSSSS2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL151233
PubChem CID:	179269
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines

*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
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17269824]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18977148]
NPO32940	lissoclinum cf. badium	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28181805]
NPO32529	polycitor sp.	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7769392]

☑ 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	4
Others	6

Activity Type	# Activity
Cell Line	5
Individual Protein	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT393	Cell Line	HCT-116	Homo sapiens	IC90	=	0.05	ug.mL-1	PMID[493005]
NPT3728	Individual Protein	p53-binding protein Mdm-2	Homo sapiens	IC50	>	295000.0	nM	PMID[493007]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	0.6	nM	PMID[493008]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	IC50	=	1.8	nM	PMID[493008]
NPT393	Cell Line	HCT-116	Homo sapiens	IC90	=	0.05	ug.mL-1	PMID[493008]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	1.69	nM	PMID[493008]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	20.0	mm	PMID[493006]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	20.0	mm	PMID[493006]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	14.0	mm	PMID[493008]

☑ 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 NPC59661 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	318
0.1-0.2	3824
0.2-0.3	14635
0.3-0.4	5274
0.4-0.5	12253
0.5-0.6	5489
0.6-0.7	857
0.7-0.8	35
0.8-0.85	5
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9203	High Similarity	NPC474553
0.8881	High Similarity	NPC296858
0.8857	High Similarity	NPC475698
0.8611	High Similarity	NPC474652
0.8611	High Similarity	NPC474649
0.8403	Intermediate Similarity	NPC261940
0.8288	Intermediate Similarity	NPC226601
0.8224	Intermediate Similarity	NPC131440
0.8182	Intermediate Similarity	NPC120075
0.8129	Intermediate Similarity	NPC94292
0.8041	Intermediate Similarity	NPC69623
0.7888	Intermediate Similarity	NPC177023
0.7857	Intermediate Similarity	NPC291583
0.7857	Intermediate Similarity	NPC191200
0.7826	Intermediate Similarity	NPC298486
0.777	Intermediate Similarity	NPC13020
0.777	Intermediate Similarity	NPC140359
0.7714	Intermediate Similarity	NPC105513
0.7626	Intermediate Similarity	NPC211992
0.7564	Intermediate Similarity	NPC298924
0.7564	Intermediate Similarity	NPC28414
0.7552	Intermediate Similarity	NPC291847
0.7546	Intermediate Similarity	NPC130921
0.7448	Intermediate Similarity	NPC262641
0.7438	Intermediate Similarity	NPC257143
0.7397	Intermediate Similarity	NPC329595
0.7397	Intermediate Similarity	NPC326599
0.7333	Intermediate Similarity	NPC21890
0.7297	Intermediate Similarity	NPC160692
0.7273	Intermediate Similarity	NPC42383
0.7239	Intermediate Similarity	NPC97811
0.7197	Intermediate Similarity	NPC292792
0.7125	Intermediate Similarity	NPC206372
0.7125	Intermediate Similarity	NPC203424
0.7123	Intermediate Similarity	NPC301713
0.7105	Intermediate Similarity	NPC253429
0.7075	Intermediate Similarity	NPC153990
0.7045	Intermediate Similarity	NPC12714
0.7045	Intermediate Similarity	NPC310905
0.7037	Intermediate Similarity	NPC186469
0.698	Remote Similarity	NPC160193
0.6978	Remote Similarity	NPC26524
0.6968	Remote Similarity	NPC323204
0.6968	Remote Similarity	NPC66518
0.6959	Remote Similarity	NPC172403
0.6933	Remote Similarity	NPC476570
0.6906	Remote Similarity	NPC146422
0.6887	Remote Similarity	NPC214869
0.6887	Remote Similarity	NPC93882
0.6887	Remote Similarity	NPC130595
0.6884	Remote Similarity	NPC137685
0.6842	Remote Similarity	NPC285078
0.6842	Remote Similarity	NPC313737
0.6842	Remote Similarity	NPC6854
0.6835	Remote Similarity	NPC173746
0.6835	Remote Similarity	NPC294249
0.6835	Remote Similarity	NPC8547
0.6835	Remote Similarity	NPC156840
0.6835	Remote Similarity	NPC257124
0.6828	Remote Similarity	NPC183262
0.6821	Remote Similarity	NPC114102
0.68	Remote Similarity	NPC155838
0.6797	Remote Similarity	NPC218530
0.6788	Remote Similarity	NPC258171
0.6788	Remote Similarity	NPC227894
0.6776	Remote Similarity	NPC118419
0.6763	Remote Similarity	NPC31279
0.6755	Remote Similarity	NPC52029
0.6755	Remote Similarity	NPC195749
0.6755	Remote Similarity	NPC35961
0.6753	Remote Similarity	NPC11147
0.6738	Remote Similarity	NPC303522
0.6738	Remote Similarity	NPC165106
0.6738	Remote Similarity	NPC204120
0.6736	Remote Similarity	NPC85276
0.6711	Remote Similarity	NPC308885
0.6711	Remote Similarity	NPC255550
0.671	Remote Similarity	NPC7018
0.671	Remote Similarity	NPC131204
0.671	Remote Similarity	NPC167944
0.671	Remote Similarity	NPC416184
0.671	Remote Similarity	NPC301050
0.671	Remote Similarity	NPC42793
0.671	Remote Similarity	NPC231884
0.6691	Remote Similarity	NPC246358
0.6691	Remote Similarity	NPC233731
0.6691	Remote Similarity	NPC165386
0.6691	Remote Similarity	NPC36108
0.6691	Remote Similarity	NPC127326
0.6691	Remote Similarity	NPC7097
0.6689	Remote Similarity	NPC217277
0.6644	Remote Similarity	NPC115627
0.6644	Remote Similarity	NPC169207
0.6644	Remote Similarity	NPC118522
0.6643	Remote Similarity	NPC179309
0.6643	Remote Similarity	NPC47194
0.6643	Remote Similarity	NPC473264
0.6643	Remote Similarity	NPC475815
0.6626	Remote Similarity	NPC60538
0.6626	Remote Similarity	NPC207824
0.6623	Remote Similarity	NPC157740
0.6623	Remote Similarity	NPC99798
0.6623	Remote Similarity	NPC251571
0.6623	Remote Similarity	NPC191302
0.6608	Remote Similarity	NPC206941
0.6597	Remote Similarity	NPC81067
0.6597	Remote Similarity	NPC221049
0.6597	Remote Similarity	NPC9341
0.6596	Remote Similarity	NPC203924
0.6596	Remote Similarity	NPC139617
0.6596	Remote Similarity	NPC78918
0.6596	Remote Similarity	NPC55300
0.6596	Remote Similarity	NPC195873
0.6596	Remote Similarity	NPC245552
0.6582	Remote Similarity	NPC314682
0.6579	Remote Similarity	NPC147247
0.6579	Remote Similarity	NPC246974
0.6561	Remote Similarity	NPC160607
0.6561	Remote Similarity	NPC14600
0.6561	Remote Similarity	NPC193528
0.6561	Remote Similarity	NPC204848
0.6561	Remote Similarity	NPC312770
0.6561	Remote Similarity	NPC41473
0.6556	Remote Similarity	NPC156944
0.6556	Remote Similarity	NPC251466
0.6552	Remote Similarity	NPC164386
0.6552	Remote Similarity	NPC293619
0.6549	Remote Similarity	NPC165646
0.6545	Remote Similarity	NPC76213
0.6545	Remote Similarity	NPC277669
0.6541	Remote Similarity	NPC328750
0.6541	Remote Similarity	NPC474915
0.6541	Remote Similarity	NPC188163
0.6541	Remote Similarity	NPC213206
0.6533	Remote Similarity	NPC300955
0.6519	Remote Similarity	NPC299583
0.6513	Remote Similarity	NPC291449
0.6513	Remote Similarity	NPC186898
0.6513	Remote Similarity	NPC41331
0.6507	Remote Similarity	NPC474040
0.6507	Remote Similarity	NPC474214
0.6507	Remote Similarity	NPC255675
0.6507	Remote Similarity	NPC470626
0.6507	Remote Similarity	NPC205502
0.6507	Remote Similarity	NPC63083
0.6506	Remote Similarity	NPC114124
0.6497	Remote Similarity	NPC174754
0.6496	Remote Similarity	NPC68055
0.649	Remote Similarity	NPC71105
0.649	Remote Similarity	NPC170583
0.649	Remote Similarity	NPC152186
0.649	Remote Similarity	NPC182147
0.649	Remote Similarity	NPC207541
0.649	Remote Similarity	NPC246133
0.6485	Remote Similarity	NPC13397
0.6481	Remote Similarity	NPC110337
0.6478	Remote Similarity	NPC77572
0.6471	Remote Similarity	NPC469977
0.6467	Remote Similarity	NPC477564
0.6467	Remote Similarity	NPC2295
0.6463	Remote Similarity	NPC474320
0.6463	Remote Similarity	NPC281298
0.6463	Remote Similarity	NPC20674
0.6463	Remote Similarity	NPC310338
0.6463	Remote Similarity	NPC308217
0.6463	Remote Similarity	NPC475961
0.6463	Remote Similarity	NPC311595
0.6463	Remote Similarity	NPC254625
0.6463	Remote Similarity	NPC299406
0.6463	Remote Similarity	NPC320987
0.6463	Remote Similarity	NPC181969
0.6463	Remote Similarity	NPC135961
0.6463	Remote Similarity	NPC15805
0.6463	Remote Similarity	NPC24474
0.6463	Remote Similarity	NPC119949
0.646	Remote Similarity	NPC136860
0.646	Remote Similarity	NPC128019
0.646	Remote Similarity	NPC476567
0.6458	Remote Similarity	NPC294941
0.6458	Remote Similarity	NPC142599
0.6456	Remote Similarity	NPC254610
0.6447	Remote Similarity	NPC236347
0.6447	Remote Similarity	NPC323775
0.6442	Remote Similarity	NPC473934
0.6439	Remote Similarity	NPC321956
0.6438	Remote Similarity	NPC304208
0.6438	Remote Similarity	NPC52464
0.6433	Remote Similarity	NPC475828
0.6429	Remote Similarity	NPC470706
0.6429	Remote Similarity	NPC80129
0.6429	Remote Similarity	NPC187022
0.6419	Remote Similarity	NPC148615
0.6419	Remote Similarity	NPC53596
0.6419	Remote Similarity	NPC177475
0.6419	Remote Similarity	NPC321133
0.6419	Remote Similarity	NPC35071
0.6419	Remote Similarity	NPC165133
0.6419	Remote Similarity	NPC17388
0.6419	Remote Similarity	NPC242885
0.6419	Remote Similarity	NPC344161

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 NPC59661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	216
0.1-0.2	1196
0.2-0.3	1656
0.3-0.4	2931
0.4-0.5	2075
0.5-0.6	867
0.6-0.7	202
0.7-0.8	7
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
0.7347	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4179	Approved
0.7125	Intermediate Similarity	NPD4180	Approved
0.7086	Intermediate Similarity	NPD2653	Approved
0.7027	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD487	Discontinued
0.698	Remote Similarity	NPD2669	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7153	Discontinued
0.6933	Remote Similarity	NPD5718	Phase 2
0.6923	Remote Similarity	NPD4162	Approved
0.6923	Remote Similarity	NPD3060	Approved
0.6906	Remote Similarity	NPD9379	Approved
0.6906	Remote Similarity	NPD9377	Approved
0.6887	Remote Similarity	NPD2674	Phase 3
0.6882	Remote Similarity	NPD730	Discontinued
0.6835	Remote Similarity	NPD228	Approved
0.6738	Remote Similarity	NPD5283	Phase 1
0.6711	Remote Similarity	NPD3144	Approved
0.6711	Remote Similarity	NPD3145	Approved
0.671	Remote Similarity	NPD6896	Approved
0.671	Remote Similarity	NPD6895	Approved
0.6708	Remote Similarity	NPD1771	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3075	Approved
0.669	Remote Similarity	NPD593	Approved
0.669	Remote Similarity	NPD595	Approved
0.6667	Remote Similarity	NPD2236	Approved
0.6646	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD1044	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD9384	Approved
0.6644	Remote Similarity	NPD9381	Approved
0.6626	Remote Similarity	NPD6031	Approved
0.6626	Remote Similarity	NPD6030	Approved
0.6624	Remote Similarity	NPD2161	Phase 2
0.6606	Remote Similarity	NPD1642	Discontinued
0.6605	Remote Similarity	NPD4739	Approved
0.6605	Remote Similarity	NPD1424	Approved
0.6585	Remote Similarity	NPD3687	Approved
0.6585	Remote Similarity	NPD3686	Approved
0.6582	Remote Similarity	NPD1375	Discontinued
0.6579	Remote Similarity	NPD596	Approved
0.6579	Remote Similarity	NPD600	Approved
0.6577	Remote Similarity	NPD9622	Approved
0.6564	Remote Similarity	NPD52	Approved
0.6564	Remote Similarity	NPD3647	Clinical (unspecified phase)
0.6564	Remote Similarity	NPD7526	Approved
0.6564	Remote Similarity	NPD7527	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD3532	Approved
0.6558	Remote Similarity	NPD3531	Approved
0.6558	Remote Similarity	NPD3530	Approved
0.6556	Remote Similarity	NPD558	Phase 2
0.6541	Remote Similarity	NPD4664	Clinical (unspecified phase)
0.651	Remote Similarity	NPD2231	Phase 2
0.651	Remote Similarity	NPD2235	Phase 2
0.6497	Remote Similarity	NPD6111	Discontinued
0.6491	Remote Similarity	NPD2644	Approved
0.6467	Remote Similarity	NPD1669	Approved
0.6463	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6331	Phase 2
0.6452	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD2245	Discovery
0.6447	Remote Similarity	NPD9621	Approved
0.6447	Remote Similarity	NPD9620	Approved
0.6447	Remote Similarity	NPD9619	Approved
0.6446	Remote Similarity	NPD6055	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD2030	Discontinued
0.6429	Remote Similarity	NPD7298	Approved
0.6429	Remote Similarity	NPD5720	Discontinued
0.6424	Remote Similarity	NPD2922	Phase 1
0.6424	Remote Similarity	NPD6662	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD196	Phase 1
0.642	Remote Similarity	NPD5241	Discontinued
0.6419	Remote Similarity	NPD2668	Approved
0.6419	Remote Similarity	NPD2667	Approved
0.64	Remote Similarity	NPD1244	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD2978	Approved
0.6391	Remote Similarity	NPD4585	Approved
0.6391	Remote Similarity	NPD2977	Approved
0.6387	Remote Similarity	NPD5109	Approved
0.6387	Remote Similarity	NPD5110	Phase 2
0.6387	Remote Similarity	NPD5111	Phase 2
0.6382	Remote Similarity	NPD3053	Approved
0.6382	Remote Similarity	NPD1820	Approved
0.6382	Remote Similarity	NPD1818	Approved
0.6382	Remote Similarity	NPD1819	Approved
0.6382	Remote Similarity	NPD3055	Approved
0.6382	Remote Similarity	NPD1817	Approved
0.638	Remote Similarity	NPD7124	Phase 2
0.6375	Remote Similarity	NPD5085	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1350	Approved
0.6364	Remote Similarity	NPD1349	Approved
0.6364	Remote Similarity	NPD1351	Approved
0.6358	Remote Similarity	NPD2429	Approved
0.6358	Remote Similarity	NPD2428	Approved
0.6346	Remote Similarity	NPD259	Phase 1
0.6346	Remote Similarity	NPD839	Approved
0.6346	Remote Similarity	NPD840	Approved
0.6345	Remote Similarity	NPD9614	Approved
0.6345	Remote Similarity	NPD9618	Approved
0.6333	Remote Similarity	NPD3705	Approved
0.6331	Remote Similarity	NPD9610	Approved
0.6331	Remote Similarity	NPD9608	Approved
0.6327	Remote Similarity	NPD5536	Phase 2
0.6325	Remote Similarity	NPD5976	Discontinued
0.6319	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5310	Approved
0.6316	Remote Similarity	NPD5311	Approved
0.631	Remote Similarity	NPD6875	Approved
0.631	Remote Similarity	NPD6876	Approved
0.6309	Remote Similarity	NPD2556	Approved
0.6309	Remote Similarity	NPD2554	Approved
0.6306	Remote Similarity	NPD1558	Phase 1
0.6303	Remote Similarity	NPD4584	Approved
0.6296	Remote Similarity	NPD4237	Approved
0.6296	Remote Similarity	NPD4236	Phase 3
0.6287	Remote Similarity	NPD2883	Discontinued
0.6284	Remote Similarity	NPD5188	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD2028	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD1039	Discontinued
0.6282	Remote Similarity	NPD601	Approved
0.6282	Remote Similarity	NPD598	Approved
0.6282	Remote Similarity	NPD597	Approved
0.628	Remote Similarity	NPD6783	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD7110	Phase 1
0.6272	Remote Similarity	NPD1757	Discontinued
0.6272	Remote Similarity	NPD7109	Clinical (unspecified phase)
0.6266	Remote Similarity	NPD3657	Discovery
0.6266	Remote Similarity	NPD555	Phase 2
0.6264	Remote Similarity	NPD7802	Discontinued
0.6257	Remote Similarity	NPD6374	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3676	Clinical (unspecified phase)
0.6242	Remote Similarity	NPD1136	Approved
0.6242	Remote Similarity	NPD1357	Approved
0.6242	Remote Similarity	NPD1130	Approved
0.6242	Remote Similarity	NPD1132	Approved
0.6242	Remote Similarity	NPD3049	Approved
0.6234	Remote Similarity	NPD7905	Discontinued
0.6228	Remote Similarity	NPD3639	Approved
0.6228	Remote Similarity	NPD3640	Phase 3
0.6228	Remote Similarity	NPD3641	Approved
0.6226	Remote Similarity	NPD2492	Phase 1
0.6224	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.622	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD3166	Approved
0.6218	Remote Similarity	NPD3167	Approved
0.6218	Remote Similarity	NPD3165	Approved
0.6218	Remote Similarity	NPD3164	Approved
0.6216	Remote Similarity	NPD9616	Approved
0.6216	Remote Similarity	NPD9613	Approved
0.6216	Remote Similarity	NPD9615	Approved
0.6205	Remote Similarity	NPD4123	Phase 3
0.6199	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD5177	Phase 3
0.6194	Remote Similarity	NPD9569	Approved
0.619	Remote Similarity	NPD4210	Discontinued
0.6184	Remote Similarity	NPD2232	Approved
0.6184	Remote Similarity	NPD2233	Approved
0.6184	Remote Similarity	NPD2230	Approved
0.6178	Remote Similarity	NPD1336	Approved
0.6174	Remote Similarity	NPD316	Approved
0.6171	Remote Similarity	NPD6107	Approved
0.6169	Remote Similarity	NPD1794	Approved
0.6164	Remote Similarity	NPD594	Approved
0.6164	Remote Similarity	NPD592	Approved
0.6163	Remote Similarity	NPD2560	Approved
0.6163	Remote Similarity	NPD2563	Approved
0.6154	Remote Similarity	NPD2614	Approved
0.6154	Remote Similarity	NPD2684	Approved
0.6154	Remote Similarity	NPD4017	Approved
0.6154	Remote Similarity	NPD4005	Discontinued
0.6154	Remote Similarity	NPD746	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD1774	Approved
0.6144	Remote Similarity	NPD1420	Approved
0.6144	Remote Similarity	NPD1421	Approved
0.6139	Remote Similarity	NPD1423	Approved
0.6136	Remote Similarity	NPD4166	Phase 2
0.6129	Remote Similarity	NPD3690	Phase 2
0.6129	Remote Similarity	NPD3691	Phase 2
0.6125	Remote Similarity	NPD3054	Approved
0.6125	Remote Similarity	NPD2986	Phase 2
0.6125	Remote Similarity	NPD2989	Phase 2
0.6125	Remote Similarity	NPD3052	Approved
0.6115	Remote Similarity	NPD9536	Phase 1
0.6115	Remote Similarity	NPD3179	Approved
0.6115	Remote Similarity	NPD9537	Phase 1
0.6115	Remote Similarity	NPD3180	Approved
0.6111	Remote Similarity	NPD3175	Clinical (unspecified phase)
0.6108	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6102	Remote Similarity	NPD4083	Discontinued
0.6101	Remote Similarity	NPD3061	Approved
0.6101	Remote Similarity	NPD3062	Approved
0.6101	Remote Similarity	NPD3059	Approved
0.6096	Remote Similarity	NPD821	Approved
0.6087	Remote Similarity	NPD5087	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