NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	181.11
Volume:	193.628
LogP:	0.79
LogD:	0.601
LogS:	-0.228
# Rotatable Bonds:	4
TPSA:	44.48
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.759
Synthetic Accessibility Score:	1.56
Fsp3:	0.4
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:	-4.752
MDCK Permeability:	0.00016380003944505006
Pgp-inhibitor:	0.0
Pgp-substrate:	0.778
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.62
Plasma Protein Binding (PPB):	7.85527229309082%
Volume Distribution (VD):	2.208
Pgp-substrate:	64.75757598876953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.828
CYP1A2-substrate:	0.942
CYP2C19-inhibitor:	0.105
CYP2C19-substrate:	0.896
CYP2C9-inhibitor:	0.014
CYP2C9-substrate:	0.772
CYP2D6-inhibitor:	0.418
CYP2D6-substrate:	0.937
CYP3A4-inhibitor:	0.051
CYP3A4-substrate:	0.472

ADMET: Excretion

Clearance (CL):	7.018
Half-life (T1/2):	0.833

ADMET: Toxicity

hERG Blockers:	0.239
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.297
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.799
Maximum Recommended Daily Dose:	0.432
Skin Sensitization:	0.738
Carcinogencity:	0.079
Eye Corrosion:	0.979
Eye Irritation:	0.131
Respiratory Toxicity:	0.96

Download Data

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

Natural Product: NPC120075

Natural Product ID:	NPC120075
*Common Name:**	2-(3,4-Dimethoxyphenyl)Ethanamine
IUPAC Name:	2-(3,4-dimethoxyphenyl)ethanamine
Synonyms:	2-(3,4-Dimethoxyphenyl)Ethanamine
Standard InCHIKey:	ANOUKFYBOAKOIR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3
SMILES:	NCCc1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL26019
PubChem CID:	8421
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

*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
NPO22998	Caloncoba echinata	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502310]
NPO25087	Hofmeisteria schaffneri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974630]
NPO17361	Delphinium iliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23100	Leandra chaetodon	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17361	Delphinium iliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20069	Solanum stenotomum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23100	Leandra chaetodon	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22068	Solanum polyadenium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26865	Vachellia caven	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24277	Centaurea eriophora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22970	Monodora myristica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22256	Pegolettia senegalensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4688	Lophozonia cunninghamii	Species	0thofagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25087	Hofmeisteria schaffneri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21379	Arthrophytum scoparium	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24919	Suttonia australis	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18600	Evasterias echinosoma	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20971	Ritterella tokioka	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20706	Euphorbia canescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22896	Blakeslea trispora	Species	Choanephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22998	Caloncoba echinata	Species	Achariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22195	Teucrium maghrebinum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22516	Cyperus scaber	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17361	Delphinium iliense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22461	Solidago multiradiata	Species	Asteraceae	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
Kd	1
MIC	1
Others	19
Potency	7

Activity Type	# Activity
Individual Protein	8
Organism	18
Protein Family	5
SINGLE PROTEIN	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4106	Individual Protein	Amine oxidase, copper containing	Homo sapiens	Activity	=	0.0	%	PMID[541968]
NPT4369	Individual Protein	Amine oxidase, copper containing	Mus musculus	Activity	=	3.8	%	PMID[541968]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	39810.7	nM	PMID[541969]
NPT442	Individual Protein	Ferritin light chain	Equus caballus	Potency	=	11220.2	nM	PMID[541969]
NPT524	Individual Protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	12589.3	nM	PMID[541969]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	3162.3	nM	PMID[541969]
NPT539	Individual Protein	Cellular tumor antigen p53	Homo sapiens	Potency	n.a.	50118.7	nM	PMID[541969]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	8912.5	nM	PMID[541969]
NPT1530	Protein Family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	4365.16	nM	PMID[541965]
NPT605	Organism	Homo sapiens	Homo sapiens	Activity	<	0.2	MU	PMID[541966]
NPT605	Organism	Homo sapiens	Homo sapiens	Log activity	=	-1.0	n.a.	PMID[541966]
NPT26852	PROTEIN FAMILY	Monoamine oxidase	Bos taurus	MAO deamination	=	64.0	%	PMID[541967]
NPT26852	PROTEIN FAMILY	Monoamine oxidase	Bos taurus	MAO deamination	=	16.0	%	PMID[541967]
NPT605	Organism	Homo sapiens	Homo sapiens	Human potency	<	1.0	MU	PMID[541967]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	4147.5	nM	PMID[541969]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	256.0	ug.mL-1	PMID[541970]
NPT605	Organism	Homo sapiens	Homo sapiens	Ratio	=	0.2	n.a.	PMID[541971]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	30.1	%	PMID[541972]
NPT20556	SINGLE PROTEIN	Replicase polyprotein 1ab	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	1.946	%	PMID[541973]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Inhibition	=	-0.15	%	PMID[541974]
NPT20	Organism	Candida albicans	Candida albicans	Inhibition	=	2.72	%	PMID[541975]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	Inhibition	=	-1.54	%	PMID[541975]
NPT19	Organism	Escherichia coli	Escherichia coli	Inhibition	=	-3.33	%	PMID[541975]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	Inhibition	=	8.69	%	PMID[541975]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	Inhibition	=	4.73	%	PMID[541975]
NPT747	Organism	Acinetobacter baumannii	Acinetobacter baumannii	Inhibition	=	24.31	%	PMID[541975]
NPT2922	Organism	Staphylococcus aureus subsp. aureus	Staphylococcus aureus subsp. aureus	Inhibition	=	8.89	%	PMID[541975]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	PMID[541976]
NPT20555	ORGANISM	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	PMID[541976]

☑ 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 NPC120075 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	194
0.1-0.2	2569
0.2-0.3	10658
0.3-0.4	7835
0.4-0.5	6312
0.5-0.6	10360
0.6-0.7	3761
0.7-0.8	934
0.8-0.85	55
0.85-0.9	13
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC298486
0.9397	High Similarity	NPC13020
0.9397	High Similarity	NPC140359
0.9224	High Similarity	NPC211992
0.9153	High Similarity	NPC105513
0.8929	High Similarity	NPC21890
0.8926	High Similarity	NPC291847
0.8899	High Similarity	NPC42383
0.8862	High Similarity	NPC326599
0.8862	High Similarity	NPC329595
0.8829	High Similarity	NPC97811
0.8807	High Similarity	NPC292792
0.878	High Similarity	NPC262641
0.8624	High Similarity	NPC310905
0.8624	High Similarity	NPC12714
0.8571	High Similarity	NPC160692
0.8571	High Similarity	NPC186469
0.8537	High Similarity	NPC301713
0.8468	Intermediate Similarity	NPC153990
0.8448	Intermediate Similarity	NPC26524
0.8362	Intermediate Similarity	NPC146422
0.8348	Intermediate Similarity	NPC137685
0.832	Intermediate Similarity	NPC172403
0.8308	Intermediate Similarity	NPC253429
0.8276	Intermediate Similarity	NPC257124
0.8276	Intermediate Similarity	NPC173746
0.8276	Intermediate Similarity	NPC8547
0.8276	Intermediate Similarity	NPC156840
0.8258	Intermediate Similarity	NPC66518
0.8258	Intermediate Similarity	NPC323204
0.8246	Intermediate Similarity	NPC227894
0.8246	Intermediate Similarity	NPC258171
0.8203	Intermediate Similarity	NPC214869
0.8203	Intermediate Similarity	NPC130595
0.8203	Intermediate Similarity	NPC93882
0.8197	Intermediate Similarity	NPC183262
0.819	Intermediate Similarity	NPC31279
0.8189	Intermediate Similarity	NPC160193
0.8182	Intermediate Similarity	NPC59661
0.814	Intermediate Similarity	NPC313737
0.814	Intermediate Similarity	NPC6854
0.814	Intermediate Similarity	NPC285078
0.8136	Intermediate Similarity	NPC303522
0.8136	Intermediate Similarity	NPC165106
0.8136	Intermediate Similarity	NPC204120
0.8125	Intermediate Similarity	NPC476570
0.8125	Intermediate Similarity	NPC114102
0.811	Intermediate Similarity	NPC155838
0.8103	Intermediate Similarity	NPC233731
0.8103	Intermediate Similarity	NPC7097
0.8103	Intermediate Similarity	NPC127326
0.8103	Intermediate Similarity	NPC36108
0.8103	Intermediate Similarity	NPC246358
0.8099	Intermediate Similarity	NPC85276
0.8077	Intermediate Similarity	NPC218530
0.8062	Intermediate Similarity	NPC118419
0.8047	Intermediate Similarity	NPC195749
0.8047	Intermediate Similarity	NPC35961
0.8047	Intermediate Similarity	NPC52029
0.8034	Intermediate Similarity	NPC179309
0.8015	Intermediate Similarity	NPC11147
0.8	Intermediate Similarity	NPC475815
0.8	Intermediate Similarity	NPC217277
0.8	Intermediate Similarity	NPC47194
0.8	Intermediate Similarity	NPC473264
0.7984	Intermediate Similarity	NPC308885
0.7984	Intermediate Similarity	NPC255550
0.7967	Intermediate Similarity	NPC118522
0.7967	Intermediate Similarity	NPC115627
0.7967	Intermediate Similarity	NPC169207
0.7966	Intermediate Similarity	NPC139617
0.7966	Intermediate Similarity	NPC245552
0.7966	Intermediate Similarity	NPC203924
0.7966	Intermediate Similarity	NPC55300
0.7966	Intermediate Similarity	NPC195873
0.7966	Intermediate Similarity	NPC78918
0.7955	Intermediate Similarity	NPC231884
0.7955	Intermediate Similarity	NPC42793
0.7955	Intermediate Similarity	NPC167944
0.7949	Intermediate Similarity	NPC165386
0.7941	Intermediate Similarity	NPC294249
0.7934	Intermediate Similarity	NPC221049
0.7934	Intermediate Similarity	NPC81067
0.7934	Intermediate Similarity	NPC9341
0.7899	Intermediate Similarity	NPC165646
0.7895	Intermediate Similarity	NPC68055
0.7891	Intermediate Similarity	NPC191302
0.7891	Intermediate Similarity	NPC99798
0.7891	Intermediate Similarity	NPC157740
0.7891	Intermediate Similarity	NPC251571
0.789	Intermediate Similarity	NPC321956
0.7869	Intermediate Similarity	NPC164386
0.7869	Intermediate Similarity	NPC293619
0.7829	Intermediate Similarity	NPC246974
0.7829	Intermediate Similarity	NPC147247
0.782	Intermediate Similarity	NPC7018
0.782	Intermediate Similarity	NPC301050
0.782	Intermediate Similarity	NPC131204
0.7812	Intermediate Similarity	NPC251466
0.7812	Intermediate Similarity	NPC156944
0.7805	Intermediate Similarity	NPC470626
0.7805	Intermediate Similarity	NPC474040
0.7805	Intermediate Similarity	NPC474214
0.7805	Intermediate Similarity	NPC205502
0.7805	Intermediate Similarity	NPC255675
0.7798	Intermediate Similarity	NPC71853
0.7795	Intermediate Similarity	NPC300955
0.7786	Intermediate Similarity	NPC207824
0.7786	Intermediate Similarity	NPC60538
0.7778	Intermediate Similarity	NPC314682
0.7769	Intermediate Similarity	NPC142599
0.7769	Intermediate Similarity	NPC294941
0.7761	Intermediate Similarity	NPC41473
0.7761	Intermediate Similarity	NPC312770
0.7761	Intermediate Similarity	NPC14600
0.7761	Intermediate Similarity	NPC193528
0.7761	Intermediate Similarity	NPC160607
0.7761	Intermediate Similarity	NPC204848
0.7752	Intermediate Similarity	NPC186898
0.7752	Intermediate Similarity	NPC41331
0.7752	Intermediate Similarity	NPC291449
0.7742	Intermediate Similarity	NPC119949
0.7742	Intermediate Similarity	NPC311595
0.7742	Intermediate Similarity	NPC24474
0.7742	Intermediate Similarity	NPC475961
0.7742	Intermediate Similarity	NPC15805
0.7742	Intermediate Similarity	NPC299406
0.7742	Intermediate Similarity	NPC308217
0.7742	Intermediate Similarity	NPC181969
0.7742	Intermediate Similarity	NPC310338
0.7742	Intermediate Similarity	NPC281298
0.7742	Intermediate Similarity	NPC320987
0.7742	Intermediate Similarity	NPC254625
0.7742	Intermediate Similarity	NPC135961
0.7742	Intermediate Similarity	NPC20674
0.7742	Intermediate Similarity	NPC474320
0.7734	Intermediate Similarity	NPC246133
0.7734	Intermediate Similarity	NPC207541
0.7734	Intermediate Similarity	NPC152186
0.7734	Intermediate Similarity	NPC71105
0.7734	Intermediate Similarity	NPC182147
0.7734	Intermediate Similarity	NPC170583
0.7724	Intermediate Similarity	NPC52464
0.7724	Intermediate Similarity	NPC304208
0.7721	Intermediate Similarity	NPC328750
0.7721	Intermediate Similarity	NPC213206
0.7721	Intermediate Similarity	NPC474915
0.7721	Intermediate Similarity	NPC188163
0.7706	Intermediate Similarity	NPC99886
0.7706	Intermediate Similarity	NPC8002
0.7706	Intermediate Similarity	NPC259134
0.7706	Intermediate Similarity	NPC177844
0.7704	Intermediate Similarity	NPC299583
0.7699	Intermediate Similarity	NPC470161
0.7692	Intermediate Similarity	NPC469977
0.768	Intermediate Similarity	NPC177475
0.768	Intermediate Similarity	NPC232316
0.768	Intermediate Similarity	NPC227217
0.768	Intermediate Similarity	NPC35071
0.768	Intermediate Similarity	NPC56214
0.768	Intermediate Similarity	NPC344161
0.768	Intermediate Similarity	NPC95614
0.768	Intermediate Similarity	NPC289330
0.768	Intermediate Similarity	NPC165133
0.768	Intermediate Similarity	NPC53596
0.768	Intermediate Similarity	NPC471308
0.768	Intermediate Similarity	NPC117780
0.768	Intermediate Similarity	NPC242885
0.768	Intermediate Similarity	NPC148615
0.768	Intermediate Similarity	NPC321133
0.768	Intermediate Similarity	NPC160120
0.768	Intermediate Similarity	NPC17388
0.7676	Intermediate Similarity	NPC277669
0.7676	Intermediate Similarity	NPC76213
0.7674	Intermediate Similarity	NPC236347
0.7674	Intermediate Similarity	NPC323775
0.7672	Intermediate Similarity	NPC241224
0.7661	Intermediate Similarity	NPC63083
0.7652	Intermediate Similarity	NPC300166
0.7642	Intermediate Similarity	NPC123948
0.7642	Intermediate Similarity	NPC268317
0.7634	Intermediate Similarity	NPC470706
0.7632	Intermediate Similarity	NPC125732
0.7632	Intermediate Similarity	NPC100870
0.763	Intermediate Similarity	NPC254610
0.7622	Intermediate Similarity	NPC114124
0.7619	Intermediate Similarity	NPC207613
0.7619	Intermediate Similarity	NPC472596
0.7619	Intermediate Similarity	NPC225245
0.7619	Intermediate Similarity	NPC267064
0.7619	Intermediate Similarity	NPC318357
0.7612	Intermediate Similarity	NPC475828
0.7606	Intermediate Similarity	NPC13397
0.76	Intermediate Similarity	NPC43275
0.7597	Intermediate Similarity	NPC320242
0.7581	Intermediate Similarity	NPC86947
0.7581	Intermediate Similarity	NPC185738
0.7581	Intermediate Similarity	NPC212643
0.7581	Intermediate Similarity	NPC259638
0.7581	Intermediate Similarity	NPC39793

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 NPC120075 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	980
0.2-0.3	1284
0.3-0.4	2406
0.4-0.5	2263
0.5-0.6	1256
0.6-0.7	589
0.7-0.8	200
0.8-0.85	16
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.879	High Similarity	NPD554	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD2653	Approved
0.84	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8362	Intermediate Similarity	NPD9377	Approved
0.8362	Intermediate Similarity	NPD9379	Approved
0.8276	Intermediate Similarity	NPD228	Approved
0.8268	Intermediate Similarity	NPD5718	Phase 2
0.8258	Intermediate Similarity	NPD7153	Discontinued
0.8203	Intermediate Similarity	NPD2674	Phase 3
0.8195	Intermediate Similarity	NPD4162	Approved
0.8195	Intermediate Similarity	NPD3060	Approved
0.8189	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8136	Intermediate Similarity	NPD5283	Phase 1
0.8067	Intermediate Similarity	NPD593	Approved
0.8067	Intermediate Similarity	NPD595	Approved
0.7984	Intermediate Similarity	NPD3144	Approved
0.7984	Intermediate Similarity	NPD3145	Approved
0.7967	Intermediate Similarity	NPD9381	Approved
0.7967	Intermediate Similarity	NPD9384	Approved
0.7955	Intermediate Similarity	NPD6896	Approved
0.7955	Intermediate Similarity	NPD6895	Approved
0.7899	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD9622	Approved
0.7852	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD2161	Phase 2
0.7829	Intermediate Similarity	NPD600	Approved
0.7829	Intermediate Similarity	NPD596	Approved
0.7812	Intermediate Similarity	NPD558	Phase 2
0.7786	Intermediate Similarity	NPD6031	Approved
0.7786	Intermediate Similarity	NPD3531	Approved
0.7786	Intermediate Similarity	NPD6030	Approved
0.7786	Intermediate Similarity	NPD3530	Approved
0.7786	Intermediate Similarity	NPD3532	Approved
0.7778	Intermediate Similarity	NPD2231	Phase 2
0.7778	Intermediate Similarity	NPD2235	Phase 2
0.7778	Intermediate Similarity	NPD1375	Discontinued
0.777	Intermediate Similarity	NPD1424	Approved
0.7761	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD3687	Approved
0.773	Intermediate Similarity	NPD3686	Approved
0.7721	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD1669	Approved
0.7714	Intermediate Similarity	NPD7526	Approved
0.7714	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD52	Approved
0.768	Intermediate Similarity	NPD2668	Approved
0.768	Intermediate Similarity	NPD2667	Approved
0.7674	Intermediate Similarity	NPD9619	Approved
0.7674	Intermediate Similarity	NPD9621	Approved
0.7674	Intermediate Similarity	NPD9620	Approved
0.7672	Intermediate Similarity	NPD9608	Approved
0.7672	Intermediate Similarity	NPD9610	Approved
0.7656	Intermediate Similarity	NPD2922	Phase 1
0.7656	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD196	Phase 1
0.7652	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD2245	Discovery
0.7623	Intermediate Similarity	NPD9614	Approved
0.7623	Intermediate Similarity	NPD9618	Approved
0.7609	Intermediate Similarity	NPD6331	Phase 2
0.7609	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD1819	Approved
0.7597	Intermediate Similarity	NPD1817	Approved
0.7597	Intermediate Similarity	NPD3055	Approved
0.7597	Intermediate Similarity	NPD1818	Approved
0.7597	Intermediate Similarity	NPD3053	Approved
0.7597	Intermediate Similarity	NPD1820	Approved
0.7589	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD5536	Phase 2
0.7578	Intermediate Similarity	NPD2429	Approved
0.7578	Intermediate Similarity	NPD2428	Approved
0.7556	Intermediate Similarity	NPD6111	Discontinued
0.7554	Intermediate Similarity	NPD5241	Discontinued
0.754	Intermediate Similarity	NPD2556	Approved
0.754	Intermediate Similarity	NPD2554	Approved
0.7519	Intermediate Similarity	NPD5311	Approved
0.7519	Intermediate Similarity	NPD839	Approved
0.7519	Intermediate Similarity	NPD840	Approved
0.7519	Intermediate Similarity	NPD5310	Approved
0.7519	Intermediate Similarity	NPD259	Phase 1
0.75	Intermediate Similarity	NPD7124	Phase 2
0.75	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD2977	Approved
0.7466	Intermediate Similarity	NPD2978	Approved
0.7463	Intermediate Similarity	NPD1558	Phase 1
0.746	Intermediate Similarity	NPD3049	Approved
0.746	Intermediate Similarity	NPD1357	Approved
0.7444	Intermediate Similarity	NPD5111	Phase 2
0.7444	Intermediate Similarity	NPD597	Approved
0.7444	Intermediate Similarity	NPD1039	Discontinued
0.7444	Intermediate Similarity	NPD598	Approved
0.7444	Intermediate Similarity	NPD5110	Phase 2
0.7444	Intermediate Similarity	NPD601	Approved
0.7444	Intermediate Similarity	NPD5109	Approved
0.7442	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD9613	Approved
0.744	Intermediate Similarity	NPD9615	Approved
0.744	Intermediate Similarity	NPD9616	Approved
0.7429	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD3705	Approved
0.7417	Intermediate Similarity	NPD2684	Approved
0.7413	Intermediate Similarity	NPD5976	Discontinued
0.741	Intermediate Similarity	NPD4237	Approved
0.741	Intermediate Similarity	NPD4236	Phase 3
0.7407	Intermediate Similarity	NPD555	Phase 2
0.7405	Intermediate Similarity	NPD7905	Discontinued
0.7398	Intermediate Similarity	NPD594	Approved
0.7398	Intermediate Similarity	NPD592	Approved
0.7397	Intermediate Similarity	NPD7298	Approved
0.7394	Intermediate Similarity	NPD4739	Approved
0.7394	Intermediate Similarity	NPD4584	Approved
0.7391	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7388	Intermediate Similarity	NPD1136	Approved
0.7388	Intermediate Similarity	NPD1130	Approved
0.7388	Intermediate Similarity	NPD1132	Approved
0.7381	Intermediate Similarity	NPD316	Approved
0.7376	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3165	Approved
0.7368	Intermediate Similarity	NPD3166	Approved
0.7368	Intermediate Similarity	NPD3164	Approved
0.7368	Intermediate Similarity	NPD3167	Approved
0.7364	Intermediate Similarity	NPD2230	Approved
0.7364	Intermediate Similarity	NPD2232	Approved
0.7364	Intermediate Similarity	NPD2233	Approved
0.7353	Intermediate Similarity	NPD2492	Phase 1
0.7348	Intermediate Similarity	NPD9569	Approved
0.7343	Intermediate Similarity	NPD1351	Approved
0.7343	Intermediate Similarity	NPD1350	Approved
0.7343	Intermediate Similarity	NPD1349	Approved
0.7328	Intermediate Similarity	NPD1794	Approved
0.7317	Intermediate Similarity	NPD821	Approved
0.7313	Intermediate Similarity	NPD1336	Approved
0.731	Intermediate Similarity	NPD3866	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD1420	Approved
0.7308	Intermediate Similarity	NPD1421	Approved
0.7305	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD2614	Approved
0.7292	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7286	Intermediate Similarity	NPD5177	Phase 3
0.7279	Intermediate Similarity	NPD5720	Discontinued
0.7273	Intermediate Similarity	NPD3691	Phase 2
0.7273	Intermediate Similarity	NPD3690	Phase 2
0.7273	Intermediate Similarity	NPD4123	Phase 3
0.7259	Intermediate Similarity	NPD1423	Approved
0.7241	Intermediate Similarity	NPD2883	Discontinued
0.7241	Intermediate Similarity	NPD4210	Discontinued
0.7239	Intermediate Similarity	NPD3179	Approved
0.7239	Intermediate Similarity	NPD3180	Approved
0.7231	Intermediate Similarity	NPD2981	Phase 2
0.723	Intermediate Similarity	NPD4585	Approved
0.7226	Intermediate Similarity	NPD3054	Approved
0.7226	Intermediate Similarity	NPD2989	Phase 2
0.7226	Intermediate Similarity	NPD3052	Approved
0.7226	Intermediate Similarity	NPD2986	Phase 2
0.7222	Intermediate Similarity	NPD3596	Phase 2
0.7206	Intermediate Similarity	NPD3061	Approved
0.7206	Intermediate Similarity	NPD3062	Approved
0.7206	Intermediate Similarity	NPD3059	Approved
0.7203	Intermediate Similarity	NPD1774	Approved
0.7194	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD4017	Approved
0.719	Intermediate Similarity	NPD1358	Approved
0.7185	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7177	Intermediate Similarity	NPD7843	Approved
0.7176	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD2983	Phase 2
0.7176	Intermediate Similarity	NPD2982	Phase 2
0.7172	Intermediate Similarity	NPD3641	Approved
0.7172	Intermediate Similarity	NPD3639	Approved
0.7172	Intermediate Similarity	NPD3640	Phase 3
0.7165	Intermediate Similarity	NPD16	Approved
0.7165	Intermediate Similarity	NPD317	Approved
0.7165	Intermediate Similarity	NPD856	Approved
0.7165	Intermediate Similarity	NPD1103	Approved
0.7165	Intermediate Similarity	NPD1102	Approved
0.7165	Intermediate Similarity	NPD318	Approved
0.7153	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6584	Phase 3
0.7143	Intermediate Similarity	NPD7157	Approved
0.7143	Intermediate Similarity	NPD709	Approved
0.7143	Intermediate Similarity	NPD4179	Approved
0.7143	Intermediate Similarity	NPD258	Approved
0.7143	Intermediate Similarity	NPD257	Approved
0.7143	Intermediate Similarity	NPD4180	Approved
0.7122	Intermediate Similarity	NPD2155	Approved
0.7122	Intermediate Similarity	NPD2156	Approved
0.7122	Intermediate Similarity	NPD2154	Approved
0.7121	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD9537	Phase 1
0.7111	Intermediate Similarity	NPD1024	Discontinued
0.7111	Intermediate Similarity	NPD3027	Phase 3
0.7111	Intermediate Similarity	NPD5163	Phase 2
0.7111	Intermediate Similarity	NPD9536	Phase 1
0.7109	Intermediate Similarity	NPD6581	Approved
0.7109	Intermediate Similarity	NPD1182	Approved
0.7109	Intermediate Similarity	NPD6580	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