NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	225.14
Volume:	237.01
LogP:	1.078
LogD:	1.057
LogS:	-1.158
# Rotatable Bonds:	6
TPSA:	39.72
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.796
Synthetic Accessibility Score:	1.829
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.535
MDCK Permeability:	1.1584151252463926e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.95
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.862
Plasma Protein Binding (PPB):	21.587387084960938%
Volume Distribution (VD):	2.332
Pgp-substrate:	47.63056945800781%

ADMET: Metabolism

CYP1A2-inhibitor:	0.491
CYP1A2-substrate:	0.726
CYP2C19-inhibitor:	0.028
CYP2C19-substrate:	0.92
CYP2C9-inhibitor:	0.005
CYP2C9-substrate:	0.571
CYP2D6-inhibitor:	0.074
CYP2D6-substrate:	0.917
CYP3A4-inhibitor:	0.042
CYP3A4-substrate:	0.768

ADMET: Excretion

Clearance (CL):	7.105
Half-life (T1/2):	0.825

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.565
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.28
Maximum Recommended Daily Dose:	0.434
Skin Sensitization:	0.927
Carcinogencity:	0.043
Eye Corrosion:	0.022
Eye Irritation:	0.025
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC262641

Natural Product ID:	NPC262641
*Common Name:**	N-Methyl-2-(3,4,5-Trimethoxyphenyl)Ethanamine
IUPAC Name:	N-methyl-2-(3,4,5-trimethoxyphenyl)ethanamine
Synonyms:
Standard InCHIKey:	OTXANOLOOUNVSR-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H19NO3/c1-13-6-5-9-7-10(14-2)12(16-4)11(8-9)15-3/h7-8,13H,5-6H2,1-4H3/p+1
SMILES:	C[NH2+]CCc1cc(c(c(c1)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL100531
PubChem CID:	138365
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
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.3923/pjbs.2013.1138.1144]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[17262437]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18326559]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Essential oil	n.a.	n.a.	PMID[23163425]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23865201]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[24508058]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25650289]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	garlic skin	n.a.	n.a.	PMID[25726329]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8350088]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Bulb	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO13613	Lophophora williamsii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13613	Lophophora williamsii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22283	Alhagi maurorum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7103	Allium sativum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13613	Lophophora williamsii	Species	Cactaceae	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
Kd	1

Activity Type	# Activity
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1530	Protein Family	Serotonin (5-HT) receptor	Rattus norvegicus	Kd	=	5248.07	nM	PMID[545985]

☑ 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 NPC262641 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	243
0.1-0.2	2319
0.2-0.3	11828
0.3-0.4	6929
0.4-0.5	6336
0.5-0.6	10078
0.6-0.7	4000
0.7-0.8	930
0.8-0.85	27
0.85-0.9	3
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.959	High Similarity	NPC105513
0.936	High Similarity	NPC291847
0.9268	High Similarity	NPC298486
0.878	High Similarity	NPC120075
0.8531	High Similarity	NPC114124
0.8455	Intermediate Similarity	NPC204120
0.8433	Intermediate Similarity	NPC160692
0.8321	Intermediate Similarity	NPC253429
0.8308	Intermediate Similarity	NPC140359
0.8308	Intermediate Similarity	NPC13020
0.8295	Intermediate Similarity	NPC211992
0.8293	Intermediate Similarity	NPC203924
0.8279	Intermediate Similarity	NPC165386
0.8239	Intermediate Similarity	NPC473934
0.8231	Intermediate Similarity	NPC190931
0.8148	Intermediate Similarity	NPC326599
0.8148	Intermediate Similarity	NPC329595
0.8143	Intermediate Similarity	NPC323204
0.8125	Intermediate Similarity	NPC63083
0.8074	Intermediate Similarity	NPC160193
0.8062	Intermediate Similarity	NPC308217
0.8062	Intermediate Similarity	NPC15805
0.8062	Intermediate Similarity	NPC475961
0.8062	Intermediate Similarity	NPC254625
0.806	Intermediate Similarity	NPC172403
0.8047	Intermediate Similarity	NPC304208
0.8047	Intermediate Similarity	NPC52464
0.8042	Intermediate Similarity	NPC110337
0.8	Intermediate Similarity	NPC296898
0.8	Intermediate Similarity	NPC59907
0.8	Intermediate Similarity	NPC37144
0.7969	Intermediate Similarity	NPC123948
0.7939	Intermediate Similarity	NPC472596
0.7923	Intermediate Similarity	NPC20674
0.7923	Intermediate Similarity	NPC119949
0.7922	Intermediate Similarity	NPC204947
0.7895	Intermediate Similarity	NPC247251
0.7883	Intermediate Similarity	NPC476570
0.7879	Intermediate Similarity	NPC477886
0.7879	Intermediate Similarity	NPC49341
0.7857	Intermediate Similarity	NPC53146
0.7857	Intermediate Similarity	NPC286790
0.7857	Intermediate Similarity	NPC21890
0.7857	Intermediate Similarity	NPC188120
0.7852	Intermediate Similarity	NPC301713
0.7852	Intermediate Similarity	NPC475557
0.7847	Intermediate Similarity	NPC294249
0.7846	Intermediate Similarity	NPC474612
0.7846	Intermediate Similarity	NPC85276
0.7838	Intermediate Similarity	NPC218575
0.7829	Intermediate Similarity	NPC193067
0.782	Intermediate Similarity	NPC264885
0.782	Intermediate Similarity	NPC261661
0.7805	Intermediate Similarity	NPC42383
0.7801	Intermediate Similarity	NPC113236
0.7801	Intermediate Similarity	NPC214036
0.7794	Intermediate Similarity	NPC153990
0.7786	Intermediate Similarity	NPC11147
0.7769	Intermediate Similarity	NPC33271
0.7769	Intermediate Similarity	NPC259638
0.7761	Intermediate Similarity	NPC220598
0.7761	Intermediate Similarity	NPC282496
0.7761	Intermediate Similarity	NPC165375
0.7761	Intermediate Similarity	NPC233526
0.776	Intermediate Similarity	NPC97811
0.7748	Intermediate Similarity	NPC160931
0.7748	Intermediate Similarity	NPC37205
0.7744	Intermediate Similarity	NPC285289
0.773	Intermediate Similarity	NPC167944
0.773	Intermediate Similarity	NPC231884
0.773	Intermediate Similarity	NPC42793
0.7727	Intermediate Similarity	NPC222175
0.7724	Intermediate Similarity	NPC292792
0.7721	Intermediate Similarity	NPC322366
0.7721	Intermediate Similarity	NPC323775
0.7721	Intermediate Similarity	NPC236347
0.7703	Intermediate Similarity	NPC207824
0.7703	Intermediate Similarity	NPC60538
0.7698	Intermediate Similarity	NPC118419
0.7687	Intermediate Similarity	NPC270326
0.7687	Intermediate Similarity	NPC194626
0.7687	Intermediate Similarity	NPC41562
0.7669	Intermediate Similarity	NPC183262
0.7669	Intermediate Similarity	NPC199023
0.7669	Intermediate Similarity	NPC166759
0.7647	Intermediate Similarity	NPC173608
0.7647	Intermediate Similarity	NPC116907
0.7647	Intermediate Similarity	NPC221077
0.7647	Intermediate Similarity	NPC251855
0.7647	Intermediate Similarity	NPC203133
0.7647	Intermediate Similarity	NPC105925
0.7647	Intermediate Similarity	NPC60885
0.7647	Intermediate Similarity	NPC472093
0.7647	Intermediate Similarity	NPC233410
0.7647	Intermediate Similarity	NPC117214
0.7647	Intermediate Similarity	NPC475169
0.7647	Intermediate Similarity	NPC17943
0.7647	Intermediate Similarity	NPC234400
0.7647	Intermediate Similarity	NPC57490
0.7647	Intermediate Similarity	NPC208950
0.7647	Intermediate Similarity	NPC193544
0.7647	Intermediate Similarity	NPC298757
0.763	Intermediate Similarity	NPC197757
0.763	Intermediate Similarity	NPC217277
0.763	Intermediate Similarity	NPC318777
0.763	Intermediate Similarity	NPC228922
0.7613	Intermediate Similarity	NPC124433
0.7613	Intermediate Similarity	NPC293871
0.7606	Intermediate Similarity	NPC131204
0.7606	Intermediate Similarity	NPC301050
0.7606	Intermediate Similarity	NPC7018
0.76	Intermediate Similarity	NPC277669
0.76	Intermediate Similarity	NPC76213
0.7597	Intermediate Similarity	NPC26524
0.7594	Intermediate Similarity	NPC474565
0.7594	Intermediate Similarity	NPC229401
0.7591	Intermediate Similarity	NPC223953
0.7591	Intermediate Similarity	NPC88297
0.7591	Intermediate Similarity	NPC44748
0.7591	Intermediate Similarity	NPC223136
0.7591	Intermediate Similarity	NPC285725
0.7591	Intermediate Similarity	NPC78974
0.7591	Intermediate Similarity	NPC214406
0.7591	Intermediate Similarity	NPC186845
0.7591	Intermediate Similarity	NPC9891
0.7591	Intermediate Similarity	NPC18924
0.7591	Intermediate Similarity	NPC103823
0.7591	Intermediate Similarity	NPC50683
0.7591	Intermediate Similarity	NPC28730
0.7591	Intermediate Similarity	NPC76451
0.7591	Intermediate Similarity	NPC112571
0.7574	Intermediate Similarity	NPC283170
0.7574	Intermediate Similarity	NPC92869
0.7574	Intermediate Similarity	NPC5796
0.7574	Intermediate Similarity	NPC191768
0.7574	Intermediate Similarity	NPC183446
0.7574	Intermediate Similarity	NPC206487
0.7571	Intermediate Similarity	NPC130595
0.7571	Intermediate Similarity	NPC93882
0.7571	Intermediate Similarity	NPC214869
0.7569	Intermediate Similarity	NPC314682
0.7561	Intermediate Similarity	NPC310905
0.7561	Intermediate Similarity	NPC12714
0.7559	Intermediate Similarity	NPC82016
0.7556	Intermediate Similarity	NPC288238
0.7556	Intermediate Similarity	NPC262253
0.7556	Intermediate Similarity	NPC211231
0.7556	Intermediate Similarity	NPC473411
0.7556	Intermediate Similarity	NPC71579
0.754	Intermediate Similarity	NPC186469
0.7536	Intermediate Similarity	NPC159968
0.7536	Intermediate Similarity	NPC236791
0.7536	Intermediate Similarity	NPC471986
0.7536	Intermediate Similarity	NPC127587
0.7536	Intermediate Similarity	NPC242032
0.7536	Intermediate Similarity	NPC210355
0.7536	Intermediate Similarity	NPC293054
0.7536	Intermediate Similarity	NPC473092
0.7536	Intermediate Similarity	NPC474119
0.7536	Intermediate Similarity	NPC189248
0.7536	Intermediate Similarity	NPC324112
0.7536	Intermediate Similarity	NPC74817
0.7536	Intermediate Similarity	NPC169474
0.7536	Intermediate Similarity	NPC202904
0.7536	Intermediate Similarity	NPC82679
0.7536	Intermediate Similarity	NPC473093
0.7536	Intermediate Similarity	NPC124452
0.7536	Intermediate Similarity	NPC8050
0.7536	Intermediate Similarity	NPC282000
0.7536	Intermediate Similarity	NPC246620
0.7533	Intermediate Similarity	NPC13397
0.7532	Intermediate Similarity	NPC7393
0.7531	Intermediate Similarity	NPC475479
0.7531	Intermediate Similarity	NPC470879
0.7531	Intermediate Similarity	NPC474507
0.7531	Intermediate Similarity	NPC258695
0.7531	Intermediate Similarity	NPC243454
0.7519	Intermediate Similarity	NPC135961
0.7518	Intermediate Similarity	NPC313737
0.7518	Intermediate Similarity	NPC64391
0.7518	Intermediate Similarity	NPC285078
0.7518	Intermediate Similarity	NPC6854
0.7518	Intermediate Similarity	NPC299584
0.7518	Intermediate Similarity	NPC82483
0.7518	Intermediate Similarity	NPC265483
0.7517	Intermediate Similarity	NPC213206
0.7517	Intermediate Similarity	NPC474915
0.7517	Intermediate Similarity	NPC328750
0.7517	Intermediate Similarity	NPC188163
0.7516	Intermediate Similarity	NPC148709
0.7516	Intermediate Similarity	NPC112575
0.7516	Intermediate Similarity	NPC476577
0.7516	Intermediate Similarity	NPC173416
0.75	Intermediate Similarity	NPC168657
0.75	Intermediate Similarity	NPC477564
0.75	Intermediate Similarity	NPC114102
0.75	Intermediate Similarity	NPC2682
0.75	Intermediate Similarity	NPC108545
0.75	Intermediate Similarity	NPC136319
0.75	Intermediate Similarity	NPC137685

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 NPC262641 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	165
0.1-0.2	876
0.2-0.3	1431
0.3-0.4	2544
0.4-0.5	2246
0.5-0.6	1195
0.6-0.7	530
0.7-0.8	154
0.8-0.85	8
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8705	High Similarity	NPD1424	Approved
0.8496	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD6111	Discontinued
0.8345	Intermediate Similarity	NPD3060	Approved
0.8309	Intermediate Similarity	NPD2653	Approved
0.8298	Intermediate Similarity	NPD7124	Phase 2
0.8252	Intermediate Similarity	NPD1351	Approved
0.8252	Intermediate Similarity	NPD1350	Approved
0.8252	Intermediate Similarity	NPD1349	Approved
0.8231	Intermediate Similarity	NPD4585	Approved
0.8134	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD4162	Approved
0.8074	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.8015	Intermediate Similarity	NPD5718	Phase 2
0.8014	Intermediate Similarity	NPD3687	Approved
0.8014	Intermediate Similarity	NPD3686	Approved
0.7972	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7838	Intermediate Similarity	NPD7261	Clinical (unspecified phase)
0.7812	Intermediate Similarity	NPD593	Approved
0.7812	Intermediate Similarity	NPD595	Approved
0.7808	Intermediate Similarity	NPD3158	Phase 1
0.7808	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD3157	Approved
0.773	Intermediate Similarity	NPD6896	Approved
0.773	Intermediate Similarity	NPD6895	Approved
0.7721	Intermediate Similarity	NPD9619	Approved
0.7721	Intermediate Similarity	NPD9620	Approved
0.7721	Intermediate Similarity	NPD859	Approved
0.7721	Intermediate Similarity	NPD602	Approved
0.7721	Intermediate Similarity	NPD858	Approved
0.7721	Intermediate Similarity	NPD9621	Approved
0.7721	Intermediate Similarity	NPD599	Approved
0.7703	Intermediate Similarity	NPD6030	Approved
0.7703	Intermediate Similarity	NPD6031	Approved
0.7647	Intermediate Similarity	NPD6788	Approved
0.7639	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD7153	Discontinued
0.7639	Intermediate Similarity	NPD1044	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD2978	Approved
0.7632	Intermediate Similarity	NPD2977	Approved
0.7626	Intermediate Similarity	NPD601	Approved
0.7626	Intermediate Similarity	NPD597	Approved
0.7626	Intermediate Similarity	NPD598	Approved
0.76	Intermediate Similarity	NPD4005	Discontinued
0.7584	Intermediate Similarity	NPD5976	Discontinued
0.7571	Intermediate Similarity	NPD3531	Approved
0.7571	Intermediate Similarity	NPD3530	Approved
0.7571	Intermediate Similarity	NPD1136	Approved
0.7571	Intermediate Similarity	NPD1130	Approved
0.7571	Intermediate Similarity	NPD2245	Discovery
0.7571	Intermediate Similarity	NPD2674	Phase 3
0.7571	Intermediate Similarity	NPD3532	Approved
0.7571	Intermediate Similarity	NPD1132	Approved
0.7569	Intermediate Similarity	NPD1375	Discontinued
0.7566	Intermediate Similarity	NPD3384	Approved
0.7566	Intermediate Similarity	NPD3383	Approved
0.7566	Intermediate Similarity	NPD3382	Approved
0.7556	Intermediate Similarity	NPD2981	Phase 2
0.7552	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD4675	Approved
0.755	Intermediate Similarity	NPD4678	Approved
0.7535	Intermediate Similarity	NPD2568	Approved
0.7518	Intermediate Similarity	NPD3053	Approved
0.7518	Intermediate Similarity	NPD3055	Approved
0.7517	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5297	Approved
0.75	Intermediate Similarity	NPD2983	Phase 2
0.75	Intermediate Similarity	NPD2982	Phase 2
0.7483	Intermediate Similarity	NPD2219	Phase 1
0.7466	Intermediate Similarity	NPD4237	Approved
0.7466	Intermediate Similarity	NPD4236	Phase 3
0.7451	Intermediate Similarity	NPD7298	Approved
0.7445	Intermediate Similarity	NPD5311	Approved
0.7445	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD5310	Approved
0.7429	Intermediate Similarity	NPD3180	Approved
0.7429	Intermediate Similarity	NPD3027	Phase 3
0.7429	Intermediate Similarity	NPD3179	Approved
0.7417	Intermediate Similarity	NPD4210	Discontinued
0.741	Intermediate Similarity	NPD3018	Phase 2
0.74	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3059	Approved
0.7394	Intermediate Similarity	NPD3062	Approved
0.7394	Intermediate Similarity	NPD3061	Approved
0.7394	Intermediate Similarity	NPD2238	Phase 2
0.7391	Intermediate Similarity	NPD1818	Approved
0.7391	Intermediate Similarity	NPD1817	Approved
0.7391	Intermediate Similarity	NPD1820	Approved
0.7391	Intermediate Similarity	NPD1819	Approved
0.7386	Intermediate Similarity	NPD5090	Approved
0.7386	Intermediate Similarity	NPD5089	Approved
0.7385	Intermediate Similarity	NPD9379	Approved
0.7385	Intermediate Similarity	NPD9377	Approved
0.7383	Intermediate Similarity	NPD1774	Approved
0.7376	Intermediate Similarity	NPD3145	Approved
0.7376	Intermediate Similarity	NPD3144	Approved
0.7375	Intermediate Similarity	NPD3489	Phase 3
0.7372	Intermediate Similarity	NPD2428	Approved
0.7372	Intermediate Similarity	NPD2429	Approved
0.7365	Intermediate Similarity	NPD5241	Discontinued
0.7357	Intermediate Similarity	NPD3537	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD600	Approved
0.7357	Intermediate Similarity	NPD596	Approved
0.7333	Intermediate Similarity	NPD9384	Approved
0.7333	Intermediate Similarity	NPD2667	Approved
0.7333	Intermediate Similarity	NPD2554	Approved
0.7333	Intermediate Similarity	NPD9381	Approved
0.7333	Intermediate Similarity	NPD2668	Approved
0.7333	Intermediate Similarity	NPD2556	Approved
0.7328	Intermediate Similarity	NPD5283	Phase 1
0.7308	Intermediate Similarity	NPD228	Approved
0.7292	Intermediate Similarity	NPD5314	Approved
0.7292	Intermediate Similarity	NPD3054	Approved
0.7292	Intermediate Similarity	NPD817	Approved
0.7292	Intermediate Similarity	NPD823	Approved
0.7292	Intermediate Similarity	NPD3052	Approved
0.7285	Intermediate Similarity	NPD7526	Approved
0.7285	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD52	Approved
0.7278	Intermediate Similarity	NPD5677	Discontinued
0.7261	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD4055	Discovery
0.726	Intermediate Similarity	NPD2161	Phase 2
0.7259	Intermediate Similarity	NPD3049	Approved
0.7248	Intermediate Similarity	NPD2677	Approved
0.7248	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD9622	Approved
0.7244	Intermediate Similarity	NPD2563	Approved
0.7244	Intermediate Similarity	NPD2560	Approved
0.7239	Intermediate Similarity	NPD16	Approved
0.7239	Intermediate Similarity	NPD9615	Approved
0.7239	Intermediate Similarity	NPD1408	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD856	Approved
0.7239	Intermediate Similarity	NPD9616	Approved
0.7239	Intermediate Similarity	NPD9613	Approved
0.723	Intermediate Similarity	NPD5177	Phase 3
0.7226	Intermediate Similarity	NPD5720	Discontinued
0.7226	Intermediate Similarity	NPD3705	Approved
0.7222	Intermediate Similarity	NPD8252	Approved
0.7222	Intermediate Similarity	NPD8251	Approved
0.7222	Intermediate Similarity	NPD8099	Discontinued
0.7219	Intermediate Similarity	NPD4123	Phase 3
0.7219	Intermediate Similarity	NPD4584	Approved
0.7214	Intermediate Similarity	NPD558	Phase 2
0.7214	Intermediate Similarity	NPD7905	Discontinued
0.7203	Intermediate Similarity	NPD839	Approved
0.7203	Intermediate Similarity	NPD840	Approved
0.72	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4606	Clinical (unspecified phase)
0.7185	Intermediate Similarity	NPD316	Approved
0.7185	Intermediate Similarity	NPD7534	Approved
0.7185	Intermediate Similarity	NPD7533	Approved
0.7183	Intermediate Similarity	NPD3165	Approved
0.7183	Intermediate Similarity	NPD3166	Approved
0.7183	Intermediate Similarity	NPD3167	Approved
0.7183	Intermediate Similarity	NPD3164	Approved
0.7179	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD8156	Discontinued
0.7172	Intermediate Similarity	NPD1772	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1794	Approved
0.7133	Intermediate Similarity	NPD1039	Discontinued
0.7133	Intermediate Similarity	NPD1336	Approved
0.7133	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD6662	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD3640	Phase 3
0.7124	Intermediate Similarity	NPD3641	Approved
0.7124	Intermediate Similarity	NPD3639	Approved
0.7123	Intermediate Similarity	NPD2200	Suspended
0.7122	Intermediate Similarity	NPD1669	Approved
0.7111	Intermediate Similarity	NPD318	Approved
0.7111	Intermediate Similarity	NPD317	Approved
0.7095	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1423	Approved
0.7071	Intermediate Similarity	NPD2922	Phase 1
0.707	Intermediate Similarity	NPD5773	Approved
0.707	Intermediate Similarity	NPD5772	Approved
0.7067	Intermediate Similarity	NPD6331	Phase 2
0.7067	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2986	Phase 2
0.7055	Intermediate Similarity	NPD2989	Phase 2
0.7055	Intermediate Similarity	NPD2492	Phase 1
0.7051	Intermediate Similarity	NPD6385	Approved
0.7051	Intermediate Similarity	NPD6386	Approved
0.705	Intermediate Similarity	NPD2232	Approved
0.705	Intermediate Similarity	NPD2233	Approved
0.705	Intermediate Similarity	NPD2230	Approved
0.705	Intermediate Similarity	NPD2235	Phase 2
0.705	Intermediate Similarity	NPD2231	Phase 2
0.7048	Intermediate Similarity	NPD7039	Approved
0.7048	Intermediate Similarity	NPD7038	Approved
0.7042	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7837	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD4357	Discontinued
0.7037	Intermediate Similarity	NPD5242	Approved
0.7034	Intermediate Similarity	NPD1558	Phase 1
0.7032	Intermediate Similarity	NPD4017	Approved
0.7027	Intermediate Similarity	NPD3175	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