NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	195.13
Volume:	210.924
LogP:	1.201
LogD:	1.18
LogS:	-0.885
# Rotatable Bonds:	5
TPSA:	30.49
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.771
Synthetic Accessibility Score:	1.617
Fsp3:	0.455
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:	-4.492
MDCK Permeability:	2.357531411689706e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.815
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.015

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.918
Plasma Protein Binding (PPB):	20.865955352783203%
Volume Distribution (VD):	3.024
Pgp-substrate:	54.068992614746094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.162
CYP1A2-substrate:	0.857
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.923
CYP2C9-inhibitor:	0.006
CYP2C9-substrate:	0.606
CYP2D6-inhibitor:	0.388
CYP2D6-substrate:	0.926
CYP3A4-inhibitor:	0.062
CYP3A4-substrate:	0.607

ADMET: Excretion

Clearance (CL):	8.127
Half-life (T1/2):	0.818

ADMET: Toxicity

hERG Blockers:	0.138
Human Hepatotoxicity (H-HT):	0.664
Drug-inuced Liver Injury (DILI):	0.074
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.553
Maximum Recommended Daily Dose:	0.673
Skin Sensitization:	0.883
Carcinogencity:	0.044
Eye Corrosion:	0.026
Eye Irritation:	0.038
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC298486

Natural Product ID:	NPC298486
*Common Name:**	2-(3,4-Dimethoxyphenyl)-N-Methylethanamine
IUPAC Name:	2-(3,4-dimethoxyphenyl)-N-methylethanamine
Synonyms:
Standard InCHIKey:	HNJWKRMESUMDQE-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H17NO2/c1-12-7-6-9-4-5-10(13-2)11(8-9)14-3/h4-5,8,12H,6-7H2,1-3H3
SMILES:	CNCCc1ccc(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1404381
PubChem CID:	77039
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]
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]
NPO23100	Leandra chaetodon	Species	Melastomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20069	Solanum stenotomum	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]
NPO22068	Solanum polyadenium	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22970	Monodora myristica	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24277	Centaurea eriophora	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]
NPO22256	Pegolettia senegalensis	Species	Asteraceae	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]

☑ 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
Potency	9

Activity Type	# Activity
Individual Protein	7
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3	Individual Protein	Thioredoxin glutathione reductase	Schistosoma mansoni	Potency	=	15848.9	nM	PMID[550485]
NPT524	Individual Protein	Serine-protein kinase ATM	Homo sapiens	Potency	=	39810.7	nM	PMID[550485]
NPT59	Individual Protein	DNA polymerase beta	Homo sapiens	Potency	=	5011.9	nM	PMID[550485]
NPT443	Individual Protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[550485]
NPT11	Individual Protein	Guanine nucleotide-binding protein G(s), subunit alpha	Homo sapiens	Potency	n.a.	39810.7	nM	PMID[550485]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	522.1	nM	PMID[550485]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	19952.6	nM	PMID[550485]
NPT803	Individual Protein	Flap endonuclease 1	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[550485]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	657.3	nM	PMID[550485]

☑ 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 NPC298486 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	202
0.1-0.2	2674
0.2-0.3	11667
0.3-0.4	6275
0.4-0.5	7898
0.5-0.6	10003
0.6-0.7	3152
0.7-0.8	753
0.8-0.85	56
0.85-0.9	13
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9478	High Similarity	NPC120075
0.9268	High Similarity	NPC262641
0.8934	High Similarity	NPC13020
0.8934	High Similarity	NPC140359
0.8926	High Similarity	NPC211992
0.8898	High Similarity	NPC160692
0.8862	High Similarity	NPC105513
0.8769	High Similarity	NPC253429
0.8712	High Similarity	NPC323204
0.8651	High Similarity	NPC172403
0.8651	High Similarity	NPC291847
0.8516	High Similarity	NPC160193
0.8475	Intermediate Similarity	NPC21890
0.845	Intermediate Similarity	NPC329595
0.845	Intermediate Similarity	NPC326599
0.8443	Intermediate Similarity	NPC85276
0.8435	Intermediate Similarity	NPC42383
0.8425	Intermediate Similarity	NPC301713
0.8376	Intermediate Similarity	NPC97811
0.8359	Intermediate Similarity	NPC153990
0.8348	Intermediate Similarity	NPC292792
0.8333	Intermediate Similarity	NPC11147
0.8308	Intermediate Similarity	NPC476570
0.8271	Intermediate Similarity	NPC42793
0.8271	Intermediate Similarity	NPC167944
0.8271	Intermediate Similarity	NPC231884
0.8248	Intermediate Similarity	NPC294249
0.8244	Intermediate Similarity	NPC118419
0.8214	Intermediate Similarity	NPC207824
0.8214	Intermediate Similarity	NPC60538
0.8189	Intermediate Similarity	NPC217277
0.8182	Intermediate Similarity	NPC26524
0.8174	Intermediate Similarity	NPC310905
0.8174	Intermediate Similarity	NPC12714
0.8136	Intermediate Similarity	NPC186469
0.8106	Intermediate Similarity	NPC214869
0.8106	Intermediate Similarity	NPC130595
0.8106	Intermediate Similarity	NPC93882
0.8099	Intermediate Similarity	NPC76213
0.8099	Intermediate Similarity	NPC277669
0.8088	Intermediate Similarity	NPC314682
0.8083	Intermediate Similarity	NPC137685
0.8045	Intermediate Similarity	NPC6854
0.8045	Intermediate Similarity	NPC313737
0.8045	Intermediate Similarity	NPC285078
0.8042	Intermediate Similarity	NPC114124
0.803	Intermediate Similarity	NPC114102
0.8029	Intermediate Similarity	NPC213206
0.8029	Intermediate Similarity	NPC474915
0.8029	Intermediate Similarity	NPC328750
0.8029	Intermediate Similarity	NPC188163
0.8028	Intermediate Similarity	NPC13397
0.8015	Intermediate Similarity	NPC155838
0.8	Intermediate Similarity	NPC301050
0.8	Intermediate Similarity	NPC323775
0.8	Intermediate Similarity	NPC7018
0.8	Intermediate Similarity	NPC236347
0.8	Intermediate Similarity	NPC131204
0.7986	Intermediate Similarity	NPC477564
0.7986	Intermediate Similarity	NPC2295
0.7985	Intermediate Similarity	NPC218530
0.7983	Intermediate Similarity	NPC258171
0.7955	Intermediate Similarity	NPC52029
0.7955	Intermediate Similarity	NPC195749
0.7955	Intermediate Similarity	NPC35961
0.7951	Intermediate Similarity	NPC146422
0.7941	Intermediate Similarity	NPC193528
0.7923	Intermediate Similarity	NPC320242
0.7907	Intermediate Similarity	NPC328267
0.7899	Intermediate Similarity	NPC66518
0.7895	Intermediate Similarity	NPC308885
0.7895	Intermediate Similarity	NPC255550
0.7886	Intermediate Similarity	NPC204120
0.7886	Intermediate Similarity	NPC165106
0.7883	Intermediate Similarity	NPC210086
0.7877	Intermediate Similarity	NPC170503
0.7877	Intermediate Similarity	NPC160931
0.7877	Intermediate Similarity	NPC126519
0.7877	Intermediate Similarity	NPC203784
0.7877	Intermediate Similarity	NPC37205
0.7874	Intermediate Similarity	NPC321133
0.7869	Intermediate Similarity	NPC257124
0.7869	Intermediate Similarity	NPC156840
0.7869	Intermediate Similarity	NPC8547
0.7869	Intermediate Similarity	NPC173746
0.7833	Intermediate Similarity	NPC227894
0.7826	Intermediate Similarity	NPC59661
0.7812	Intermediate Similarity	NPC183262
0.7808	Intermediate Similarity	NPC187022
0.7808	Intermediate Similarity	NPC80129
0.7803	Intermediate Similarity	NPC99798
0.7803	Intermediate Similarity	NPC157740
0.7803	Intermediate Similarity	NPC251571
0.7803	Intermediate Similarity	NPC191302
0.7801	Intermediate Similarity	NPC145304
0.7801	Intermediate Similarity	NPC185838
0.7801	Intermediate Similarity	NPC130926
0.7794	Intermediate Similarity	NPC475828
0.7787	Intermediate Similarity	NPC31279
0.7786	Intermediate Similarity	NPC128019
0.7786	Intermediate Similarity	NPC318965
0.7786	Intermediate Similarity	NPC136860
0.7786	Intermediate Similarity	NPC476567
0.7778	Intermediate Similarity	NPC137096
0.776	Intermediate Similarity	NPC47194
0.776	Intermediate Similarity	NPC475815
0.776	Intermediate Similarity	NPC473264
0.7754	Intermediate Similarity	NPC231572
0.7746	Intermediate Similarity	NPC473934
0.7744	Intermediate Similarity	NPC471306
0.7744	Intermediate Similarity	NPC147247
0.7744	Intermediate Similarity	NPC471321
0.7744	Intermediate Similarity	NPC246974
0.7742	Intermediate Similarity	NPC303522
0.774	Intermediate Similarity	NPC292003
0.7737	Intermediate Similarity	NPC416184
0.7727	Intermediate Similarity	NPC251466
0.7727	Intermediate Similarity	NPC156944
0.7724	Intermediate Similarity	NPC55300
0.7724	Intermediate Similarity	NPC203924
0.771	Intermediate Similarity	NPC300955
0.7705	Intermediate Similarity	NPC246358
0.7705	Intermediate Similarity	NPC7097
0.7705	Intermediate Similarity	NPC36108
0.7705	Intermediate Similarity	NPC233731
0.7705	Intermediate Similarity	NPC127326
0.7698	Intermediate Similarity	NPC81067
0.7698	Intermediate Similarity	NPC9341
0.7692	Intermediate Similarity	NPC476144
0.7692	Intermediate Similarity	NPC106295
0.7692	Intermediate Similarity	NPC51957
0.7692	Intermediate Similarity	NPC321505
0.7692	Intermediate Similarity	NPC476151
0.7692	Intermediate Similarity	NPC210437
0.7692	Intermediate Similarity	NPC16107
0.7692	Intermediate Similarity	NPC179825
0.7692	Intermediate Similarity	NPC191376
0.7681	Intermediate Similarity	NPC41473
0.7681	Intermediate Similarity	NPC14600
0.7681	Intermediate Similarity	NPC160607
0.7681	Intermediate Similarity	NPC252107
0.7681	Intermediate Similarity	NPC312770
0.7681	Intermediate Similarity	NPC204848
0.7669	Intermediate Similarity	NPC186898
0.7669	Intermediate Similarity	NPC291449
0.7669	Intermediate Similarity	NPC41331
0.7661	Intermediate Similarity	NPC165646
0.7652	Intermediate Similarity	NPC71105
0.7652	Intermediate Similarity	NPC136112
0.7652	Intermediate Similarity	NPC207541
0.7652	Intermediate Similarity	NPC152186
0.7652	Intermediate Similarity	NPC170583
0.7652	Intermediate Similarity	NPC182147
0.7652	Intermediate Similarity	NPC141739
0.7652	Intermediate Similarity	NPC246133
0.7643	Intermediate Similarity	NPC204546
0.7642	Intermediate Similarity	NPC179309
0.7639	Intermediate Similarity	NPC135538
0.7639	Intermediate Similarity	NPC24233
0.7639	Intermediate Similarity	NPC147390
0.7639	Intermediate Similarity	NPC475959
0.7639	Intermediate Similarity	NPC7467
0.7639	Intermediate Similarity	NPC476571
0.7639	Intermediate Similarity	NPC428
0.7639	Intermediate Similarity	NPC246587
0.7638	Intermediate Similarity	NPC293619
0.7638	Intermediate Similarity	NPC164386
0.7635	Intermediate Similarity	NPC190931
0.7626	Intermediate Similarity	NPC299583
0.7616	Intermediate Similarity	NPC124433
0.7616	Intermediate Similarity	NPC293871
0.7616	Intermediate Similarity	NPC475393
0.7612	Intermediate Similarity	NPC469977
0.7609	Intermediate Similarity	NPC145446
0.7609	Intermediate Similarity	NPC99078
0.7609	Intermediate Similarity	NPC137172
0.7597	Intermediate Similarity	NPC471308
0.7597	Intermediate Similarity	NPC169207
0.7597	Intermediate Similarity	NPC289330
0.7597	Intermediate Similarity	NPC118522
0.7597	Intermediate Similarity	NPC115627
0.7597	Intermediate Similarity	NPC17388
0.7597	Intermediate Similarity	NPC53596
0.7597	Intermediate Similarity	NPC160120
0.7591	Intermediate Similarity	NPC167096
0.7589	Intermediate Similarity	NPC908
0.7589	Intermediate Similarity	NPC138438
0.7586	Intermediate Similarity	NPC211296
0.7586	Intermediate Similarity	NPC219162
0.7586	Intermediate Similarity	NPC92541
0.7586	Intermediate Similarity	NPC477565
0.7586	Intermediate Similarity	NPC103379
0.7581	Intermediate Similarity	NPC195873
0.7581	Intermediate Similarity	NPC245552
0.7581	Intermediate Similarity	NPC139617
0.7581	Intermediate Similarity	NPC78918
0.7578	Intermediate Similarity	NPC474040
0.7578	Intermediate Similarity	NPC474214
0.7578	Intermediate Similarity	NPC470626
0.7574	Intermediate Similarity	NPC97870

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 NPC298486 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	144
0.1-0.2	852
0.2-0.3	1262
0.3-0.4	2234
0.4-0.5	2434
0.5-0.6	1390
0.6-0.7	579
0.7-0.8	229
0.8-0.85	19
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.912	High Similarity	NPD554	Clinical (unspecified phase)
0.8906	High Similarity	NPD2653	Approved
0.873	High Similarity	NPD5752	Clinical (unspecified phase)
0.8647	High Similarity	NPD4162	Approved
0.8647	High Similarity	NPD3060	Approved
0.8594	High Similarity	NPD5718	Phase 2
0.8516	High Similarity	NPD2669	Clinical (unspecified phase)
0.8417	Intermediate Similarity	NPD593	Approved
0.8417	Intermediate Similarity	NPD595	Approved
0.8333	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.8271	Intermediate Similarity	NPD6895	Approved
0.8271	Intermediate Similarity	NPD6896	Approved
0.8214	Intermediate Similarity	NPD6031	Approved
0.8214	Intermediate Similarity	NPD6030	Approved
0.8201	Intermediate Similarity	NPD1424	Approved
0.8162	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD7153	Discontinued
0.8162	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD3686	Approved
0.8156	Intermediate Similarity	NPD3687	Approved
0.8143	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.8106	Intermediate Similarity	NPD3532	Approved
0.8106	Intermediate Similarity	NPD2245	Discovery
0.8106	Intermediate Similarity	NPD3530	Approved
0.8106	Intermediate Similarity	NPD2674	Phase 3
0.8106	Intermediate Similarity	NPD3531	Approved
0.8074	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.8074	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.8062	Intermediate Similarity	NPD3053	Approved
0.8062	Intermediate Similarity	NPD3055	Approved
0.8029	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9620	Approved
0.8	Intermediate Similarity	NPD9619	Approved
0.8	Intermediate Similarity	NPD9621	Approved
0.7984	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD5310	Approved
0.7984	Intermediate Similarity	NPD5311	Approved
0.7951	Intermediate Similarity	NPD9379	Approved
0.7951	Intermediate Similarity	NPD9377	Approved
0.7923	Intermediate Similarity	NPD1819	Approved
0.7923	Intermediate Similarity	NPD1818	Approved
0.7923	Intermediate Similarity	NPD1820	Approved
0.7923	Intermediate Similarity	NPD1817	Approved
0.7907	Intermediate Similarity	NPD2428	Approved
0.7907	Intermediate Similarity	NPD2429	Approved
0.7895	Intermediate Similarity	NPD598	Approved
0.7895	Intermediate Similarity	NPD601	Approved
0.7895	Intermediate Similarity	NPD3144	Approved
0.7895	Intermediate Similarity	NPD3145	Approved
0.7895	Intermediate Similarity	NPD597	Approved
0.7886	Intermediate Similarity	NPD5283	Phase 1
0.7877	Intermediate Similarity	NPD2978	Approved
0.7877	Intermediate Similarity	NPD2977	Approved
0.7874	Intermediate Similarity	NPD2554	Approved
0.7874	Intermediate Similarity	NPD2667	Approved
0.7874	Intermediate Similarity	NPD2668	Approved
0.7874	Intermediate Similarity	NPD2556	Approved
0.7869	Intermediate Similarity	NPD228	Approved
0.7857	Intermediate Similarity	NPD5241	Discontinued
0.7836	Intermediate Similarity	NPD1136	Approved
0.7836	Intermediate Similarity	NPD1130	Approved
0.7836	Intermediate Similarity	NPD1132	Approved
0.7808	Intermediate Similarity	NPD7298	Approved
0.7801	Intermediate Similarity	NPD7124	Phase 2
0.7795	Intermediate Similarity	NPD3049	Approved
0.7778	Intermediate Similarity	NPD9615	Approved
0.7778	Intermediate Similarity	NPD9616	Approved
0.7778	Intermediate Similarity	NPD9613	Approved
0.7754	Intermediate Similarity	NPD2161	Phase 2
0.7737	Intermediate Similarity	NPD6111	Discontinued
0.773	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD7905	Discontinued
0.7717	Intermediate Similarity	NPD316	Approved
0.7708	Intermediate Similarity	NPD5976	Discontinued
0.7698	Intermediate Similarity	NPD1375	Discontinued
0.7692	Intermediate Similarity	NPD4584	Approved
0.7687	Intermediate Similarity	NPD3167	Approved
0.7687	Intermediate Similarity	NPD3165	Approved
0.7687	Intermediate Similarity	NPD3166	Approved
0.7687	Intermediate Similarity	NPD5720	Discontinued
0.7687	Intermediate Similarity	NPD3164	Approved
0.7676	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD1794	Approved
0.7647	Intermediate Similarity	NPD3061	Approved
0.7647	Intermediate Similarity	NPD3059	Approved
0.7647	Intermediate Similarity	NPD3062	Approved
0.7639	Intermediate Similarity	NPD7526	Approved
0.7639	Intermediate Similarity	NPD1350	Approved
0.7639	Intermediate Similarity	NPD1351	Approved
0.7639	Intermediate Similarity	NPD1349	Approved
0.7639	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD52	Approved
0.7635	Intermediate Similarity	NPD4585	Approved
0.7634	Intermediate Similarity	NPD1669	Approved
0.763	Intermediate Similarity	NPD1336	Approved
0.763	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD1039	Discontinued
0.7612	Intermediate Similarity	NPD596	Approved
0.7612	Intermediate Similarity	NPD600	Approved
0.7597	Intermediate Similarity	NPD9384	Approved
0.7597	Intermediate Similarity	NPD9381	Approved
0.7594	Intermediate Similarity	NPD558	Phase 2
0.7589	Intermediate Similarity	NPD4236	Phase 3
0.7589	Intermediate Similarity	NPD4237	Approved
0.7586	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2922	Phase 1
0.7574	Intermediate Similarity	NPD1423	Approved
0.7557	Intermediate Similarity	NPD2235	Phase 2
0.7557	Intermediate Similarity	NPD2231	Phase 2
0.7557	Intermediate Similarity	NPD2232	Approved
0.7557	Intermediate Similarity	NPD2233	Approved
0.7557	Intermediate Similarity	NPD2230	Approved
0.7556	Intermediate Similarity	NPD3179	Approved
0.7556	Intermediate Similarity	NPD3180	Approved
0.7536	Intermediate Similarity	NPD5314	Approved
0.7536	Intermediate Similarity	NPD817	Approved
0.7536	Intermediate Similarity	NPD2989	Phase 2
0.7536	Intermediate Similarity	NPD2986	Phase 2
0.7536	Intermediate Similarity	NPD3054	Approved
0.7536	Intermediate Similarity	NPD823	Approved
0.7536	Intermediate Similarity	NPD2492	Phase 1
0.7536	Intermediate Similarity	NPD3052	Approved
0.7535	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD6331	Phase 2
0.7534	Intermediate Similarity	NPD4210	Discontinued
0.7517	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD856	Approved
0.75	Intermediate Similarity	NPD1102	Approved
0.75	Intermediate Similarity	NPD1420	Approved
0.75	Intermediate Similarity	NPD1103	Approved
0.75	Intermediate Similarity	NPD1774	Approved
0.75	Intermediate Similarity	NPD1421	Approved
0.75	Intermediate Similarity	NPD16	Approved
0.75	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9622	Approved
0.7483	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4017	Approved
0.7466	Intermediate Similarity	NPD3639	Approved
0.7466	Intermediate Similarity	NPD3640	Phase 3
0.7466	Intermediate Similarity	NPD3641	Approved
0.7465	Intermediate Similarity	NPD5177	Phase 3
0.7448	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD840	Approved
0.7445	Intermediate Similarity	NPD839	Approved
0.7445	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD4179	Approved
0.7432	Intermediate Similarity	NPD4180	Approved
0.7429	Intermediate Similarity	NPD2155	Approved
0.7429	Intermediate Similarity	NPD2156	Approved
0.7429	Intermediate Similarity	NPD2154	Approved
0.7426	Intermediate Similarity	NPD5163	Phase 2
0.7391	Intermediate Similarity	NPD2238	Phase 2
0.7388	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD1797	Approved
0.7385	Intermediate Similarity	NPD1798	Approved
0.7383	Intermediate Similarity	NPD7110	Phase 1
0.7383	Intermediate Similarity	NPD7109	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD5536	Phase 2
0.7364	Intermediate Similarity	NPD317	Approved
0.7364	Intermediate Similarity	NPD318	Approved
0.7361	Intermediate Similarity	NPD2677	Approved
0.7355	Intermediate Similarity	NPD4083	Discontinued
0.7343	Intermediate Similarity	NPD2460	Phase 3
0.7343	Intermediate Similarity	NPD2458	Approved
0.7343	Intermediate Similarity	NPD2459	Approved
0.7338	Intermediate Similarity	NPD1341	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD6107	Approved
0.7329	Intermediate Similarity	NPD4123	Phase 3
0.7329	Intermediate Similarity	NPD4739	Approved
0.7325	Intermediate Similarity	NPD5708	Clinical (unspecified phase)
0.7319	Intermediate Similarity	NPD3163	Approved
0.7319	Intermediate Similarity	NPD3162	Approved
0.7315	Intermediate Similarity	NPD6875	Approved
0.7315	Intermediate Similarity	NPD6876	Approved
0.7313	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD196	Phase 1
0.731	Intermediate Similarity	NPD2120	Phase 2
0.7308	Intermediate Similarity	NPD2486	Discontinued
0.7295	Intermediate Similarity	NPD9608	Approved
0.7295	Intermediate Similarity	NPD9610	Approved
0.7292	Intermediate Similarity	NPD3977	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4166	Phase 2
0.7287	Intermediate Similarity	NPD3596	Phase 2
0.7285	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4773	Phase 2
0.7267	Intermediate Similarity	NPD4772	Phase 2
0.7266	Intermediate Similarity	NPD9614	Approved
0.7266	Intermediate Similarity	NPD9618	Approved
0.7266	Intermediate Similarity	NPD3109	Approved
0.7266	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD3110	Approved
0.7259	Intermediate Similarity	NPD4098	Discontinued
0.7254	Intermediate Similarity	NPD2240	Approved
0.7254	Intermediate Similarity	NPD3156	Discontinued
0.7254	Intermediate Similarity	NPD2239	Approved
0.7252	Intermediate Similarity	NPD1357	Approved
0.7248	Intermediate Similarity	NPD824	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