NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	149.03
Volume:	154.691
LogP:	2.091
LogD:	2.425
LogS:	-2.756
# Rotatable Bonds:	2
TPSA:	23.79
# H-Bond Aceptor:	1
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.603
Synthetic Accessibility Score:	2.177
Fsp3:	0.125
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:	-4.401
MDCK Permeability:	6.52823073323816e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.985
Plasma Protein Binding (PPB):	75.62315368652344%
Volume Distribution (VD):	1.913
Pgp-substrate:	22.988496780395508%

ADMET: Metabolism

CYP1A2-inhibitor:	0.965
CYP1A2-substrate:	0.527
CYP2C19-inhibitor:	0.435
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.143
CYP2C9-substrate:	0.162
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.033
CYP3A4-substrate:	0.328

ADMET: Excretion

Clearance (CL):	8.826
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.113
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.382
Rat Oral Acute Toxicity:	0.293
Maximum Recommended Daily Dose:	0.095
Skin Sensitization:	0.946
Carcinogencity:	0.242
Eye Corrosion:	0.984
Eye Irritation:	0.994
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC52330

Natural Product ID:	NPC52330
*Common Name:**	Benzyl Thiocyanate
IUPAC Name:	benzyl thiocyanate
Synonyms:
Standard InCHIKey:	ABNDFSOIUFLJAH-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H7NS/c9-7-10-6-8-4-2-1-3-5-8/h1-5H,6H2
SMILES:	N#CSCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2251721
PubChem CID:	18170
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004549] Benzyl thiocyanates

*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
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2008.09.013]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	Flowers	São Paulo, Brazil.		PMID[32156350]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	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	1
Others	4
Potency	9

Activity Type	# Activity
Individual Protein	1
Organism	4
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1250	Individual Protein	Macrophage migration inhibitory factor	Homo sapiens	IC50	>	100000.0	nM	PMID[476794]
NPT449	Organism	Meloidogyne javanica	Meloidogyne javanica	LC90	=	8.71	ug ml-1	PMID[476793]
NPT449	Organism	Meloidogyne javanica	Meloidogyne javanica	LC50	=	4.64	ug.mL-1	PMID[476793]
NPT449	Organism	Meloidogyne javanica	Meloidogyne javanica	mortality	=	66.36	%	PMID[476793]
NPT449	Organism	Meloidogyne javanica	Meloidogyne javanica	mortality	=	30.14	%	PMID[476793]
NPT2	Others	Unspecified		Potency	n.a.	27417.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61893.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	2443.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	9809.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	24640.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	77272	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	48755.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1224.7	nM	PubChem BioAssay data set

☑ 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 NPC52330 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	1756
0.1-0.2	8724
0.2-0.3	16467
0.3-0.4	12893
0.4-0.5	2201
0.5-0.6	474
0.6-0.7	128
0.7-0.8	47
0.8-0.85	4
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8806	High Similarity	NPC5324
0.8594	High Similarity	NPC45255
0.8358	Intermediate Similarity	NPC36440
0.8095	Intermediate Similarity	NPC149436
0.806	Intermediate Similarity	NPC50266
0.7969	Intermediate Similarity	NPC269586
0.7969	Intermediate Similarity	NPC198841
0.7857	Intermediate Similarity	NPC181786
0.7846	Intermediate Similarity	NPC65873
0.7846	Intermediate Similarity	NPC212114
0.7846	Intermediate Similarity	NPC300345
0.7846	Intermediate Similarity	NPC120441
0.7812	Intermediate Similarity	NPC277704
0.7727	Intermediate Similarity	NPC114327
0.7727	Intermediate Similarity	NPC36357
0.7727	Intermediate Similarity	NPC8235
0.7612	Intermediate Similarity	NPC147062
0.7612	Intermediate Similarity	NPC169110
0.75	Intermediate Similarity	NPC248705
0.75	Intermediate Similarity	NPC210849
0.75	Intermediate Similarity	NPC200936
0.75	Intermediate Similarity	NPC238023
0.75	Intermediate Similarity	NPC246588
0.75	Intermediate Similarity	NPC310758
0.75	Intermediate Similarity	NPC54368
0.75	Intermediate Similarity	NPC135924
0.75	Intermediate Similarity	NPC150196
0.7463	Intermediate Similarity	NPC64270
0.7432	Intermediate Similarity	NPC244738
0.7391	Intermediate Similarity	NPC200745
0.7391	Intermediate Similarity	NPC29680
0.7391	Intermediate Similarity	NPC71009
0.7391	Intermediate Similarity	NPC66517
0.7391	Intermediate Similarity	NPC22786
0.7353	Intermediate Similarity	NPC147578
0.7333	Intermediate Similarity	NPC299134
0.7286	Intermediate Similarity	NPC113670
0.7286	Intermediate Similarity	NPC21211
0.7286	Intermediate Similarity	NPC88566
0.7246	Intermediate Similarity	NPC200624
0.7215	Intermediate Similarity	NPC475573
0.7215	Intermediate Similarity	NPC475289
0.72	Intermediate Similarity	NPC212463
0.7183	Intermediate Similarity	NPC198023
0.7183	Intermediate Similarity	NPC155172
0.7183	Intermediate Similarity	NPC32312
0.7183	Intermediate Similarity	NPC291066
0.7162	Intermediate Similarity	NPC229235
0.7083	Intermediate Similarity	NPC178527
0.7042	Intermediate Similarity	NPC45756
0.7042	Intermediate Similarity	NPC22627
0.7024	Intermediate Similarity	NPC53492
0.6986	Remote Similarity	NPC6107
0.6986	Remote Similarity	NPC267443
0.6951	Remote Similarity	NPC474088
0.6935	Remote Similarity	NPC11150
0.6933	Remote Similarity	NPC219246
0.6923	Remote Similarity	NPC110264
0.6923	Remote Similarity	NPC302129
0.6892	Remote Similarity	NPC82770
0.6892	Remote Similarity	NPC311343
0.6892	Remote Similarity	NPC78954
0.6892	Remote Similarity	NPC239931
0.6883	Remote Similarity	NPC113000
0.6883	Remote Similarity	NPC122327
0.6883	Remote Similarity	NPC112609
0.6849	Remote Similarity	NPC289915
0.6849	Remote Similarity	NPC113837
0.6842	Remote Similarity	NPC125144
0.6842	Remote Similarity	NPC121708
0.6812	Remote Similarity	NPC469807
0.68	Remote Similarity	NPC16190
0.68	Remote Similarity	NPC246822
0.68	Remote Similarity	NPC98880
0.68	Remote Similarity	NPC169222
0.68	Remote Similarity	NPC213570
0.68	Remote Similarity	NPC235059
0.68	Remote Similarity	NPC473206
0.68	Remote Similarity	NPC139416
0.6795	Remote Similarity	NPC276699
0.6795	Remote Similarity	NPC98976
0.6712	Remote Similarity	NPC264470
0.6711	Remote Similarity	NPC72670
0.6711	Remote Similarity	NPC251490
0.6711	Remote Similarity	NPC263385
0.6711	Remote Similarity	NPC95289
0.6709	Remote Similarity	NPC271642
0.6709	Remote Similarity	NPC139658
0.6706	Remote Similarity	NPC148231
0.6629	Remote Similarity	NPC473661
0.6625	Remote Similarity	NPC325662
0.6625	Remote Similarity	NPC98269
0.6625	Remote Similarity	NPC290638
0.6623	Remote Similarity	NPC193578
0.6623	Remote Similarity	NPC326200
0.6623	Remote Similarity	NPC158028
0.6623	Remote Similarity	NPC208302
0.6623	Remote Similarity	NPC74458
0.6623	Remote Similarity	NPC1008
0.6623	Remote Similarity	NPC87099
0.6623	Remote Similarity	NPC135433
0.6623	Remote Similarity	NPC39799
0.6623	Remote Similarity	NPC155429
0.6623	Remote Similarity	NPC280135
0.6623	Remote Similarity	NPC226999
0.6543	Remote Similarity	NPC12857
0.6538	Remote Similarity	NPC54269
0.6538	Remote Similarity	NPC1901
0.6538	Remote Similarity	NPC285679
0.6538	Remote Similarity	NPC271437
0.6456	Remote Similarity	NPC258492
0.6456	Remote Similarity	NPC96835
0.6456	Remote Similarity	NPC208075
0.6456	Remote Similarity	NPC108218
0.6447	Remote Similarity	NPC22760
0.6404	Remote Similarity	NPC185501
0.6386	Remote Similarity	NPC192623
0.6386	Remote Similarity	NPC309279
0.6375	Remote Similarity	NPC32203
0.6375	Remote Similarity	NPC307195
0.6375	Remote Similarity	NPC206800
0.6375	Remote Similarity	NPC189371
0.6364	Remote Similarity	NPC297358
0.631	Remote Similarity	NPC231986
0.6296	Remote Similarity	NPC175393
0.6235	Remote Similarity	NPC14326
0.622	Remote Similarity	NPC249018
0.622	Remote Similarity	NPC298023
0.622	Remote Similarity	NPC3672
0.622	Remote Similarity	NPC245966
0.622	Remote Similarity	NPC3190
0.622	Remote Similarity	NPC287790
0.622	Remote Similarity	NPC9796
0.622	Remote Similarity	NPC179726
0.622	Remote Similarity	NPC329318
0.6211	Remote Similarity	NPC275104
0.6203	Remote Similarity	NPC470796
0.6196	Remote Similarity	NPC71140
0.6163	Remote Similarity	NPC104070
0.6163	Remote Similarity	NPC119677
0.6145	Remote Similarity	NPC176228
0.6145	Remote Similarity	NPC285470
0.6145	Remote Similarity	NPC255345
0.6145	Remote Similarity	NPC66270
0.6145	Remote Similarity	NPC36342
0.6145	Remote Similarity	NPC76455
0.6145	Remote Similarity	NPC137847
0.6145	Remote Similarity	NPC245896
0.6145	Remote Similarity	NPC2785
0.6145	Remote Similarity	NPC224544
0.6145	Remote Similarity	NPC103488
0.6145	Remote Similarity	NPC50192
0.6122	Remote Similarity	NPC469974
0.6098	Remote Similarity	NPC78500
0.6092	Remote Similarity	NPC133162
0.6092	Remote Similarity	NPC169016
0.6076	Remote Similarity	NPC105991
0.6071	Remote Similarity	NPC167577
0.6071	Remote Similarity	NPC272260
0.6071	Remote Similarity	NPC300205
0.6071	Remote Similarity	NPC78517
0.6071	Remote Similarity	NPC139901
0.6071	Remote Similarity	NPC170484
0.6071	Remote Similarity	NPC159661
0.6071	Remote Similarity	NPC151405
0.6071	Remote Similarity	NPC8981
0.6071	Remote Similarity	NPC469894
0.6067	Remote Similarity	NPC211237
0.6056	Remote Similarity	NPC56072
0.6024	Remote Similarity	NPC66655
0.6023	Remote Similarity	NPC3210
0.6	Remote Similarity	NPC127343
0.6	Remote Similarity	NPC184030
0.6	Remote Similarity	NPC164449
0.6	Remote Similarity	NPC315216
0.6	Remote Similarity	NPC285716
0.6	Remote Similarity	NPC157055
0.6	Remote Similarity	NPC195713
0.6	Remote Similarity	NPC328178
0.6	Remote Similarity	NPC190567
0.6	Remote Similarity	NPC121800
0.6	Remote Similarity	NPC477703
0.6	Remote Similarity	NPC164086
0.6	Remote Similarity	NPC17408
0.6	Remote Similarity	NPC71664
0.6	Remote Similarity	NPC95868
0.6	Remote Similarity	NPC50063
0.5977	Remote Similarity	NPC146703
0.5955	Remote Similarity	NPC258046
0.5955	Remote Similarity	NPC203076
0.5952	Remote Similarity	NPC67863
0.593	Remote Similarity	NPC73978
0.593	Remote Similarity	NPC165212
0.593	Remote Similarity	NPC242628
0.593	Remote Similarity	NPC12936
0.593	Remote Similarity	NPC145053
0.593	Remote Similarity	NPC133050
0.593	Remote Similarity	NPC117180
0.593	Remote Similarity	NPC273033
0.593	Remote Similarity	NPC303245

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 NPC52330 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	776
0.1-0.2	994
0.2-0.3	3083
0.3-0.4	2834
0.4-0.5	1086
0.5-0.6	297
0.6-0.7	74
0.7-0.8	6
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
0.7941	Intermediate Similarity	NPD173	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD9728	Phase 1
0.7286	Intermediate Similarity	NPD675	Discontinued
0.7262	Intermediate Similarity	NPD1628	Approved
0.7262	Intermediate Similarity	NPD1629	Approved
0.7176	Intermediate Similarity	NPD4728	Approved
0.7067	Intermediate Similarity	NPD294	Approved
0.7067	Intermediate Similarity	NPD292	Approved
0.6883	Remote Similarity	NPD9594	Approved
0.6883	Remote Similarity	NPD505	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD80	Approved
0.6883	Remote Similarity	NPD9592	Approved
0.6883	Remote Similarity	NPD9593	Approved
0.6883	Remote Similarity	NPD9588	Approved
0.6883	Remote Similarity	NPD9589	Approved
0.6883	Remote Similarity	NPD9590	Approved
0.6883	Remote Similarity	NPD9591	Approved
0.68	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3456	Approved
0.6778	Remote Similarity	NPD3458	Approved
0.6778	Remote Similarity	NPD3457	Approved
0.6625	Remote Similarity	NPD603	Approved
0.6625	Remote Similarity	NPD4144	Approved
0.6625	Remote Similarity	NPD4147	Approved
0.6591	Remote Similarity	NPD2811	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD9397	Approved
0.6543	Remote Similarity	NPD9564	Approved
0.6543	Remote Similarity	NPD296	Approved
0.6543	Remote Similarity	NPD295	Approved
0.6543	Remote Similarity	NPD9393	Approved
0.6543	Remote Similarity	NPD9563	Approved
0.6543	Remote Similarity	NPD79	Approved
0.6543	Remote Similarity	NPD293	Approved
0.6526	Remote Similarity	NPD744	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD1007	Discontinued
0.6463	Remote Similarity	NPD590	Approved
0.6463	Remote Similarity	NPD1051	Approved
0.6463	Remote Similarity	NPD507	Approved
0.6463	Remote Similarity	NPD1053	Approved
0.6463	Remote Similarity	NPD1052	Approved
0.6463	Remote Similarity	NPD508	Approved
0.6463	Remote Similarity	NPD589	Approved
0.6413	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD3979	Approved
0.6386	Remote Similarity	NPD3904	Approved
0.6386	Remote Similarity	NPD5371	Approved
0.6386	Remote Similarity	NPD1617	Discontinued
0.6386	Remote Similarity	NPD260	Discontinued
0.6386	Remote Similarity	NPD3903	Approved
0.6386	Remote Similarity	NPD3981	Approved
0.6386	Remote Similarity	NPD5372	Approved
0.6383	Remote Similarity	NPD1796	Phase 3
0.6375	Remote Similarity	NPD9716	Approved
0.6364	Remote Similarity	NPD1673	Approved
0.6353	Remote Similarity	NPD423	Phase 3
0.6316	Remote Similarity	NPD1795	Discontinued
0.631	Remote Similarity	NPD472	Approved
0.631	Remote Similarity	NPD4026	Approved
0.631	Remote Similarity	NPD3035	Approved
0.631	Remote Similarity	NPD4027	Approved
0.6279	Remote Similarity	NPD785	Approved
0.6237	Remote Similarity	NPD3832	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4701	Clinical (unspecified phase)
0.6235	Remote Similarity	NPD4169	Approved
0.6235	Remote Similarity	NPD4170	Approved
0.6211	Remote Similarity	NPD4007	Approved
0.6211	Remote Similarity	NPD4008	Approved
0.6207	Remote Similarity	NPD2208	Approved
0.6207	Remote Similarity	NPD2205	Approved
0.6186	Remote Similarity	NPD1387	Phase 1
0.618	Remote Similarity	NPD9184	Approved
0.618	Remote Similarity	NPD9186	Approved
0.6163	Remote Similarity	NPD2001	Discontinued
0.6163	Remote Similarity	NPD830	Approved
0.6163	Remote Similarity	NPD263	Approved
0.6163	Remote Similarity	NPD4635	Approved
0.6163	Remote Similarity	NPD831	Approved
0.6163	Remote Similarity	NPD262	Approved
0.6163	Remote Similarity	NPD1800	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD3459	Approved
0.6146	Remote Similarity	NPD6354	Discontinued
0.6145	Remote Similarity	NPD225	Approved
0.6145	Remote Similarity	NPD227	Approved
0.6122	Remote Similarity	NPD488	Approved
0.6122	Remote Similarity	NPD489	Approved
0.6092	Remote Similarity	NPD3427	Approved
0.6092	Remote Similarity	NPD3429	Approved
0.6092	Remote Similarity	NPD2539	Approved
0.6092	Remote Similarity	NPD9395	Approved
0.6092	Remote Similarity	NPD4544	Approved
0.6092	Remote Similarity	NPD5178	Approved
0.6092	Remote Similarity	NPD2538	Approved
0.6082	Remote Similarity	NPD1386	Phase 1
0.6071	Remote Similarity	NPD1475	Approved
0.6071	Remote Similarity	NPD9490	Approved
0.6042	Remote Similarity	NPD4737	Phase 2
0.6042	Remote Similarity	NPD1067	Discontinued
0.604	Remote Similarity	NPD7156	Discontinued
0.6029	Remote Similarity	NPD9072	Clinical (unspecified phase)
0.6024	Remote Similarity	NPD9294	Approved
0.6023	Remote Similarity	NPD5916	Discontinued
0.6023	Remote Similarity	NPD9505	Clinical (unspecified phase)
0.6022	Remote Similarity	NPD1409	Phase 3
0.6022	Remote Similarity	NPD837	Approved
0.6	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5675	Discontinued
0.6	Remote Similarity	NPD914	Suspended
0.596	Remote Similarity	NPD2980	Phase 2
0.5955	Remote Similarity	NPD4406	Approved
0.5955	Remote Similarity	NPD4409	Approved
0.5955	Remote Similarity	NPD4636	Approved
0.5955	Remote Similarity	NPD304	Approved
0.5955	Remote Similarity	NPD5252	Clinical (unspecified phase)
0.5955	Remote Similarity	NPD305	Approved
0.593	Remote Similarity	NPD226	Approved
0.593	Remote Similarity	NPD942	Approved
0.59	Remote Similarity	NPD2833	Approved
0.59	Remote Similarity	NPD2834	Approved
0.5895	Remote Similarity	NPD838	Approved
0.5889	Remote Similarity	NPD783	Approved
0.5889	Remote Similarity	NPD782	Approved
0.5889	Remote Similarity	NPD4145	Approved
0.5889	Remote Similarity	NPD9538	Approved
0.5889	Remote Similarity	NPD2002	Discontinued
0.5889	Remote Similarity	NPD187	Approved
0.5889	Remote Similarity	NPD3426	Approved
0.5889	Remote Similarity	NPD780	Approved
0.5889	Remote Similarity	NPD3428	Approved
0.5889	Remote Similarity	NPD781	Approved
0.5889	Remote Similarity	NPD4146	Approved
0.5865	Remote Similarity	NPD4991	Discontinued
0.5842	Remote Similarity	NPD9702	Discontinued
0.5833	Remote Similarity	NPD1672	Phase 2
0.5824	Remote Similarity	NPD531	Approved
0.5824	Remote Similarity	NPD3345	Approved
0.5824	Remote Similarity	NPD587	Approved
0.5824	Remote Similarity	NPD1101	Approved
0.5824	Remote Similarity	NPD588	Approved
0.581	Remote Similarity	NPD1267	Approved
0.581	Remote Similarity	NPD1265	Approved
0.5795	Remote Similarity	NPD1185	Approved
0.5795	Remote Similarity	NPD9491	Approved
0.5795	Remote Similarity	NPD5288	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD4000	Phase 3
0.5795	Remote Similarity	NPD3971	Phase 1
0.5778	Remote Similarity	NPD3099	Discontinued
0.5778	Remote Similarity	NPD1697	Approved
0.5761	Remote Similarity	NPD771	Phase 3
0.5761	Remote Similarity	NPD9349	Approved
0.5761	Remote Similarity	NPD9348	Approved
0.5761	Remote Similarity	NPD9	Approved
0.5761	Remote Similarity	NPD5656	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD9350	Approved
0.5761	Remote Similarity	NPD297	Approved
0.5761	Remote Similarity	NPD9351	Phase 3
0.5755	Remote Similarity	NPD5063	Approved
0.5755	Remote Similarity	NPD5064	Approved
0.5747	Remote Similarity	NPD9250	Approved
0.5743	Remote Similarity	NPD1576	Approved
0.5729	Remote Similarity	NPD157	Clinical (unspecified phase)
0.5701	Remote Similarity	NPD5589	Approved
0.5699	Remote Similarity	NPD5915	Approved
0.5699	Remote Similarity	NPD3346	Approved
0.5699	Remote Similarity	NPD3344	Approved
0.5682	Remote Similarity	NPD9302	Approved
0.5673	Remote Similarity	NPD1317	Discontinued
0.5673	Remote Similarity	NPD5278	Discontinued
0.5667	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.5638	Remote Similarity	NPD2997	Approved
0.5638	Remote Similarity	NPD2998	Approved
0.5638	Remote Similarity	NPD4543	Discontinued
0.5638	Remote Similarity	NPD7160	Approved
0.5638	Remote Similarity	NPD3000	Approved
0.5638	Remote Similarity	NPD517	Discontinued
0.5638	Remote Similarity	NPD530	Approved
0.5618	Remote Similarity	NPD9303	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