NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	179.13
Volume:	202.133
LogP:	2.213
LogD:	2.06
LogS:	-3.158
# Rotatable Bonds:	4
TPSA:	35.25
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.767
Synthetic Accessibility Score:	1.997
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:	-4.626
MDCK Permeability:	3.71293535863515e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.152
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.254

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.956
Plasma Protein Binding (PPB):	61.46580505371094%
Volume Distribution (VD):	4.504
Pgp-substrate:	45.36784744262695%

ADMET: Metabolism

CYP1A2-inhibitor:	0.916
CYP1A2-substrate:	0.872
CYP2C19-inhibitor:	0.267
CYP2C19-substrate:	0.89
CYP2C9-inhibitor:	0.047
CYP2C9-substrate:	0.31
CYP2D6-inhibitor:	0.937
CYP2D6-substrate:	0.916
CYP3A4-inhibitor:	0.064
CYP3A4-substrate:	0.479

ADMET: Excretion

Clearance (CL):	10.359
Half-life (T1/2):	0.231

ADMET: Toxicity

hERG Blockers:	0.588
Human Hepatotoxicity (H-HT):	0.191
Drug-inuced Liver Injury (DILI):	0.047
AMES Toxicity:	0.167
Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.786
Skin Sensitization:	0.093
Carcinogencity:	0.229
Eye Corrosion:	0.003
Eye Irritation:	0.017
Respiratory Toxicity:	0.919

Download Data

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

Natural Product: NPC26524

Natural Product ID:	NPC26524
*Common Name:**	1-(4-Ethoxyphenyl)Propan-2-Amine
IUPAC Name:	1-(4-ethoxyphenyl)propan-2-amine
Synonyms:
Standard InCHIKey:	CCAMEVFYMFXHEN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H17NO/c1-3-13-11-6-4-10(5-7-11)8-9(2)12/h4-7,9H,3,8,12H2,1-2H3
SMILES:	CCOc1ccc(cc1)CC(C)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL161985
PubChem CID:	125379
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000186] Phenethylamines [CHEMONTID:0000188] Amphetamines and derivatives

*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
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12088434]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21707257]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12935	Thymus quinquecostatus	Species	Lamiaceae	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
Ki	4

Activity Type	# Activity
Individual Protein	4
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT438	Individual Protein	Serotonin 2c (5-HT2c) receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[531206]
NPT1488	Individual Protein	Monoamine oxidase A	Rattus norvegicus	IC50	=	200.0	nM	PMID[531207]
NPT1488	Individual Protein	Monoamine oxidase A	Rattus norvegicus	Ki	=	220.0	nM	PMID[531208]
NPT1487	Individual Protein	Monoamine oxidase B	Rattus norvegicus	Ki	>	100000.0	nM	PMID[531208]
NPT1777	Protein Family	Serotonin 2 (5-HT2) receptor	Rattus norvegicus	Ki	>	10000.0	nM	PMID[531206]

☑ 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 NPC26524 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	173
0.1-0.2	2762
0.2-0.3	10436
0.3-0.4	7768
0.4-0.5	7342
0.5-0.6	10769
0.6-0.7	3147
0.7-0.8	275
0.8-0.85	19
0.85-0.9	3
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC97811
0.9238	High Similarity	NPC42383
0.8909	High Similarity	NPC21890
0.8889	High Similarity	NPC186469
0.8571	High Similarity	NPC328267
0.8448	Intermediate Similarity	NPC120075
0.843	Intermediate Similarity	NPC320242
0.8273	Intermediate Similarity	NPC108875
0.8273	Intermediate Similarity	NPC38079
0.825	Intermediate Similarity	NPC211992
0.8241	Intermediate Similarity	NPC471576
0.8235	Intermediate Similarity	NPC263835
0.8198	Intermediate Similarity	NPC470393
0.8198	Intermediate Similarity	NPC473855
0.819	Intermediate Similarity	NPC321956
0.8182	Intermediate Similarity	NPC298486
0.8167	Intermediate Similarity	NPC318357
0.813	Intermediate Similarity	NPC136112
0.813	Intermediate Similarity	NPC141739
0.8095	Intermediate Similarity	NPC71853
0.8091	Intermediate Similarity	NPC51633
0.8049	Intermediate Similarity	NPC272463
0.8031	Intermediate Similarity	NPC247018
0.8031	Intermediate Similarity	NPC307123
0.8031	Intermediate Similarity	NPC97870
0.8018	Intermediate Similarity	NPC192596
0.8	Intermediate Similarity	NPC99886
0.8	Intermediate Similarity	NPC177844
0.8	Intermediate Similarity	NPC259134
0.8	Intermediate Similarity	NPC291847
0.8	Intermediate Similarity	NPC8002
0.7982	Intermediate Similarity	NPC95755
0.7967	Intermediate Similarity	NPC13020
0.7967	Intermediate Similarity	NPC140359
0.7909	Intermediate Similarity	NPC125732
0.7909	Intermediate Similarity	NPC100870
0.7903	Intermediate Similarity	NPC105513
0.7891	Intermediate Similarity	NPC470392
0.787	Intermediate Similarity	NPC471581
0.7851	Intermediate Similarity	NPC43275
0.7823	Intermediate Similarity	NPC217277
0.7807	Intermediate Similarity	NPC176971
0.7788	Intermediate Similarity	NPC283546
0.7787	Intermediate Similarity	NPC321133
0.7778	Intermediate Similarity	NPC166837
0.7768	Intermediate Similarity	NPC307425
0.7759	Intermediate Similarity	NPC145638
0.7759	Intermediate Similarity	NPC290566
0.7739	Intermediate Similarity	NPC157473
0.7739	Intermediate Similarity	NPC258171
0.7739	Intermediate Similarity	NPC151530
0.7719	Intermediate Similarity	NPC128730
0.7719	Intermediate Similarity	NPC8302
0.7705	Intermediate Similarity	NPC256369
0.7692	Intermediate Similarity	NPC88868
0.7692	Intermediate Similarity	NPC231251
0.7692	Intermediate Similarity	NPC25067
0.7687	Intermediate Similarity	NPC204546
0.768	Intermediate Similarity	NPC211218
0.768	Intermediate Similarity	NPC255253
0.7679	Intermediate Similarity	NPC107101
0.7674	Intermediate Similarity	NPC329595
0.7674	Intermediate Similarity	NPC326599
0.7672	Intermediate Similarity	NPC309982
0.7672	Intermediate Similarity	NPC146530
0.7672	Intermediate Similarity	NPC291837
0.7658	Intermediate Similarity	NPC313918
0.7658	Intermediate Similarity	NPC470161
0.7652	Intermediate Similarity	NPC326801
0.7619	Intermediate Similarity	NPC62101
0.7619	Intermediate Similarity	NPC95733
0.7611	Intermediate Similarity	NPC300166
0.7607	Intermediate Similarity	NPC24777
0.7597	Intermediate Similarity	NPC262641
0.7565	Intermediate Similarity	NPC473393
0.7565	Intermediate Similarity	NPC238115
0.7559	Intermediate Similarity	NPC29477
0.7559	Intermediate Similarity	NPC110131
0.7544	Intermediate Similarity	NPC179686
0.7544	Intermediate Similarity	NPC68055
0.7544	Intermediate Similarity	NPC298224
0.7544	Intermediate Similarity	NPC305205
0.7542	Intermediate Similarity	NPC46844
0.7537	Intermediate Similarity	NPC282087
0.7537	Intermediate Similarity	NPC259800
0.7537	Intermediate Similarity	NPC318984
0.7537	Intermediate Similarity	NPC328137
0.7537	Intermediate Similarity	NPC318028
0.7537	Intermediate Similarity	NPC317741
0.7537	Intermediate Similarity	NPC241086
0.7522	Intermediate Similarity	NPC13755
0.7521	Intermediate Similarity	NPC10286
0.7521	Intermediate Similarity	NPC213
0.7519	Intermediate Similarity	NPC283079
0.75	Intermediate Similarity	NPC303611
0.75	Intermediate Similarity	NPC113457
0.75	Intermediate Similarity	NPC289330
0.75	Intermediate Similarity	NPC326447
0.75	Intermediate Similarity	NPC226096
0.75	Intermediate Similarity	NPC17388
0.75	Intermediate Similarity	NPC290515
0.75	Intermediate Similarity	NPC108606
0.75	Intermediate Similarity	NPC471308
0.75	Intermediate Similarity	NPC164514
0.75	Intermediate Similarity	NPC160120
0.75	Intermediate Similarity	NPC175298
0.75	Intermediate Similarity	NPC53596
0.7481	Intermediate Similarity	NPC212850
0.7481	Intermediate Similarity	NPC83289
0.7481	Intermediate Similarity	NPC189724
0.7479	Intermediate Similarity	NPC55300
0.7478	Intermediate Similarity	NPC292792
0.7478	Intermediate Similarity	NPC38209
0.7478	Intermediate Similarity	NPC241224
0.7463	Intermediate Similarity	NPC231163
0.7463	Intermediate Similarity	NPC318591
0.7463	Intermediate Similarity	NPC474673
0.7463	Intermediate Similarity	NPC253429
0.7458	Intermediate Similarity	NPC474272
0.7458	Intermediate Similarity	NPC259554
0.7447	Intermediate Similarity	NPC47672
0.7445	Intermediate Similarity	NPC78530
0.7438	Intermediate Similarity	NPC235250
0.7436	Intermediate Similarity	NPC251306
0.7436	Intermediate Similarity	NPC194034
0.7422	Intermediate Similarity	NPC124776
0.7419	Intermediate Similarity	NPC283760
0.7417	Intermediate Similarity	NPC115379
0.7417	Intermediate Similarity	NPC165646
0.7407	Intermediate Similarity	NPC326860
0.7407	Intermediate Similarity	NPC197239
0.7395	Intermediate Similarity	NPC106141
0.7395	Intermediate Similarity	NPC137685
0.7391	Intermediate Similarity	NPC12870
0.7391	Intermediate Similarity	NPC24327
0.7377	Intermediate Similarity	NPC303370
0.7373	Intermediate Similarity	NPC75440
0.7368	Intermediate Similarity	NPC29601
0.7368	Intermediate Similarity	NPC155847
0.7368	Intermediate Similarity	NPC289381
0.7364	Intermediate Similarity	NPC301713
0.7355	Intermediate Similarity	NPC90903
0.7355	Intermediate Similarity	NPC303522
0.735	Intermediate Similarity	NPC1065
0.7348	Intermediate Similarity	NPC274732
0.7348	Intermediate Similarity	NPC471953
0.7348	Intermediate Similarity	NPC118419
0.7343	Intermediate Similarity	NPC203424
0.7343	Intermediate Similarity	NPC206372
0.7339	Intermediate Similarity	NPC293424
0.7328	Intermediate Similarity	NPC109637
0.7323	Intermediate Similarity	NPC471315
0.7323	Intermediate Similarity	NPC471314
0.7317	Intermediate Similarity	NPC106551
0.7317	Intermediate Similarity	NPC188867
0.7317	Intermediate Similarity	NPC281686
0.7308	Intermediate Similarity	NPC153990
0.7304	Intermediate Similarity	NPC12714
0.7304	Intermediate Similarity	NPC84325
0.7304	Intermediate Similarity	NPC310905
0.7299	Intermediate Similarity	NPC66518
0.7295	Intermediate Similarity	NPC161696
0.7293	Intermediate Similarity	NPC160692
0.7293	Intermediate Similarity	NPC325568
0.7292	Intermediate Similarity	NPC233926
0.728	Intermediate Similarity	NPC59561
0.728	Intermediate Similarity	NPC172253
0.7273	Intermediate Similarity	NPC146422
0.7266	Intermediate Similarity	NPC247298
0.7265	Intermediate Similarity	NPC475269
0.7259	Intermediate Similarity	NPC307682
0.7258	Intermediate Similarity	NPC323948
0.7252	Intermediate Similarity	NPC471321
0.7252	Intermediate Similarity	NPC471306
0.725	Intermediate Similarity	NPC473809
0.725	Intermediate Similarity	NPC475852
0.7241	Intermediate Similarity	NPC178902
0.7232	Intermediate Similarity	NPC20142
0.7232	Intermediate Similarity	NPC215351
0.7231	Intermediate Similarity	NPC218323
0.7227	Intermediate Similarity	NPC201959
0.7214	Intermediate Similarity	NPC17760
0.7213	Intermediate Similarity	NPC301735
0.7203	Intermediate Similarity	NPC231705
0.719	Intermediate Similarity	NPC266932
0.719	Intermediate Similarity	NPC245552
0.7185	Intermediate Similarity	NPC11147
0.7185	Intermediate Similarity	NPC237227
0.7179	Intermediate Similarity	NPC12987
0.7179	Intermediate Similarity	NPC474603
0.7179	Intermediate Similarity	NPC2518
0.7179	Intermediate Similarity	NPC226778
0.7179	Intermediate Similarity	NPC304761
0.7179	Intermediate Similarity	NPC147000
0.7179	Intermediate Similarity	NPC150254
0.7177	Intermediate Similarity	NPC258992
0.7176	Intermediate Similarity	NPC172403
0.7176	Intermediate Similarity	NPC251571
0.7174	Intermediate Similarity	NPC323204
0.7172	Intermediate Similarity	NPC156311

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 NPC26524 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	153
0.1-0.2	921
0.2-0.3	1154
0.3-0.4	2287
0.4-0.5	2302
0.5-0.6	1450
0.6-0.7	663
0.7-0.8	195
0.8-0.85	18
0.85-0.9	7
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8839	High Similarity	NPD595	Approved
0.8839	High Similarity	NPD593	Approved
0.875	High Similarity	NPD592	Approved
0.875	High Similarity	NPD594	Approved
0.8571	High Similarity	NPD2428	Approved
0.8571	High Similarity	NPD2429	Approved
0.8547	High Similarity	NPD2554	Approved
0.8547	High Similarity	NPD2556	Approved
0.8462	Intermediate Similarity	NPD3049	Approved
0.843	Intermediate Similarity	NPD1819	Approved
0.843	Intermediate Similarity	NPD1820	Approved
0.843	Intermediate Similarity	NPD1817	Approved
0.843	Intermediate Similarity	NPD1818	Approved
0.8273	Intermediate Similarity	NPD9608	Approved
0.8273	Intermediate Similarity	NPD9610	Approved
0.8268	Intermediate Similarity	NPD3054	Approved
0.8268	Intermediate Similarity	NPD3052	Approved
0.824	Intermediate Similarity	NPD3056	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD3596	Phase 2
0.8182	Intermediate Similarity	NPD2231	Phase 2
0.8182	Intermediate Similarity	NPD2235	Phase 2
0.8174	Intermediate Similarity	NPD821	Approved
0.816	Intermediate Similarity	NPD3167	Approved
0.816	Intermediate Similarity	NPD3164	Approved
0.816	Intermediate Similarity	NPD3165	Approved
0.816	Intermediate Similarity	NPD3166	Approved
0.813	Intermediate Similarity	NPD1794	Approved
0.813	Intermediate Similarity	NPD1770	Clinical (unspecified phase)
0.8067	Intermediate Similarity	NPD6581	Approved
0.8067	Intermediate Similarity	NPD6580	Approved
0.8065	Intermediate Similarity	NPD558	Phase 2
0.8065	Intermediate Similarity	NPD3690	Phase 2
0.8065	Intermediate Similarity	NPD3691	Phase 2
0.8049	Intermediate Similarity	NPD196	Phase 1
0.8031	Intermediate Similarity	NPD1423	Approved
0.8016	Intermediate Similarity	NPD5746	Approved
0.8016	Intermediate Similarity	NPD3179	Approved
0.8016	Intermediate Similarity	NPD3180	Approved
0.8	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7982	Intermediate Similarity	NPD2684	Approved
0.7966	Intermediate Similarity	NPD2557	Approved
0.7939	Intermediate Similarity	NPD3175	Clinical (unspecified phase)
0.7937	Intermediate Similarity	NPD596	Approved
0.7937	Intermediate Similarity	NPD600	Approved
0.7917	Intermediate Similarity	NPD2486	Discontinued
0.7895	Intermediate Similarity	NPD9624	Approved
0.7891	Intermediate Similarity	NPD5745	Approved
0.7891	Intermediate Similarity	NPD2245	Discovery
0.7874	Intermediate Similarity	NPD5163	Phase 2
0.7851	Intermediate Similarity	NPD2595	Approved
0.7851	Intermediate Similarity	NPD2594	Approved
0.7823	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD2614	Approved
0.7787	Intermediate Similarity	NPD2667	Approved
0.7787	Intermediate Similarity	NPD2668	Approved
0.7761	Intermediate Similarity	NPD2459	Approved
0.7761	Intermediate Similarity	NPD2460	Phase 3
0.7761	Intermediate Similarity	NPD2458	Approved
0.7759	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD3532	Approved
0.7752	Intermediate Similarity	NPD554	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD3531	Approved
0.7752	Intermediate Similarity	NPD3530	Approved
0.7739	Intermediate Similarity	NPD5373	Approved
0.7739	Intermediate Similarity	NPD5374	Approved
0.7734	Intermediate Similarity	NPD6179	Discontinued
0.7727	Intermediate Similarity	NPD7425	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3294	Phase 2
0.7712	Intermediate Similarity	NPD7843	Approved
0.771	Intermediate Similarity	NPD2653	Approved
0.7705	Intermediate Similarity	NPD3443	Approved
0.7705	Intermediate Similarity	NPD6382	Discontinued
0.7705	Intermediate Similarity	NPD3445	Approved
0.7705	Intermediate Similarity	NPD3444	Approved
0.7687	Intermediate Similarity	NPD7153	Discontinued
0.7686	Intermediate Similarity	NPD318	Approved
0.7686	Intermediate Similarity	NPD317	Approved
0.768	Intermediate Similarity	NPD6542	Approved
0.768	Intermediate Similarity	NPD6582	Phase 2
0.768	Intermediate Similarity	NPD3685	Discontinued
0.768	Intermediate Similarity	NPD6543	Approved
0.768	Intermediate Similarity	NPD6540	Phase 3
0.768	Intermediate Similarity	NPD6583	Phase 3
0.768	Intermediate Similarity	NPD6539	Approved
0.768	Intermediate Similarity	NPD4129	Approved
0.7669	Intermediate Similarity	NPD2240	Approved
0.7669	Intermediate Similarity	NPD2239	Approved
0.7652	Intermediate Similarity	NPD1536	Approved
0.7638	Intermediate Similarity	NPD2990	Approved
0.7638	Intermediate Similarity	NPD2987	Approved
0.7638	Intermediate Similarity	NPD7018	Phase 2
0.763	Intermediate Similarity	NPD4162	Approved
0.7619	Intermediate Similarity	NPD6538	Approved
0.7619	Intermediate Similarity	NPD6541	Approved
0.7619	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD4474	Approved
0.7615	Intermediate Similarity	NPD3162	Approved
0.7615	Intermediate Similarity	NPD7477	Discontinued
0.7615	Intermediate Similarity	NPD3163	Approved
0.7615	Intermediate Similarity	NPD4475	Approved
0.7609	Intermediate Similarity	NPD3536	Discontinued
0.7609	Intermediate Similarity	NPD1771	Clinical (unspecified phase)
0.7607	Intermediate Similarity	NPD550	Approved
0.7607	Intermediate Similarity	NPD551	Approved
0.7583	Intermediate Similarity	NPD9614	Approved
0.7583	Intermediate Similarity	NPD9618	Approved
0.7559	Intermediate Similarity	NPD4098	Discontinued
0.7559	Intermediate Similarity	NPD3568	Approved
0.7559	Intermediate Similarity	NPD3567	Approved
0.7557	Intermediate Similarity	NPD3597	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD856	Approved
0.7541	Intermediate Similarity	NPD16	Approved
0.754	Intermediate Similarity	NPD1669	Approved
0.7538	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7538	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD1537	Approved
0.7537	Intermediate Similarity	NPD1538	Phase 1
0.7537	Intermediate Similarity	NPD1519	Approved
0.7521	Intermediate Similarity	NPD7157	Approved
0.7519	Intermediate Similarity	NPD1521	Approved
0.7519	Intermediate Similarity	NPD1520	Approved
0.75	Intermediate Similarity	NPD9609	Approved
0.75	Intermediate Similarity	NPD1241	Discontinued
0.75	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9611	Approved
0.75	Intermediate Similarity	NPD9612	Approved
0.75	Intermediate Similarity	NPD6584	Phase 3
0.75	Intermediate Similarity	NPD3134	Approved
0.7482	Intermediate Similarity	NPD2874	Phase 2
0.7463	Intermediate Similarity	NPD2155	Approved
0.7463	Intermediate Similarity	NPD2156	Approved
0.7463	Intermediate Similarity	NPD2154	Approved
0.746	Intermediate Similarity	NPD2561	Approved
0.746	Intermediate Similarity	NPD2562	Approved
0.7444	Intermediate Similarity	NPD2986	Phase 2
0.7444	Intermediate Similarity	NPD2989	Phase 2
0.7442	Intermediate Similarity	NPD1712	Approved
0.7436	Intermediate Similarity	NPD290	Approved
0.7436	Intermediate Similarity	NPD1358	Approved
0.7429	Intermediate Similarity	NPD52	Approved
0.7429	Intermediate Similarity	NPD7526	Approved
0.7429	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4597	Approved
0.7426	Intermediate Similarity	NPD1372	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4598	Approved
0.7426	Intermediate Similarity	NPD2030	Discontinued
0.7424	Intermediate Similarity	NPD3140	Approved
0.7424	Intermediate Similarity	NPD3142	Approved
0.7417	Intermediate Similarity	NPD5535	Approved
0.7407	Intermediate Similarity	NPD1522	Approved
0.7407	Intermediate Similarity	NPD1523	Approved
0.7405	Intermediate Similarity	NPD1336	Approved
0.7402	Intermediate Similarity	NPD1421	Approved
0.7402	Intermediate Similarity	NPD1420	Approved
0.7391	Intermediate Similarity	NPD5160	Discontinued
0.7388	Intermediate Similarity	NPD2200	Suspended
0.7376	Intermediate Similarity	NPD6030	Approved
0.7376	Intermediate Similarity	NPD6031	Approved
0.735	Intermediate Similarity	NPD811	Approved
0.735	Intermediate Similarity	NPD968	Approved
0.735	Intermediate Similarity	NPD810	Approved
0.735	Intermediate Similarity	NPD812	Approved
0.7348	Intermediate Similarity	NPD839	Approved
0.7348	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7348	Intermediate Similarity	NPD840	Approved
0.7343	Intermediate Similarity	NPD4180	Approved
0.7343	Intermediate Similarity	NPD4179	Approved
0.7339	Intermediate Similarity	NPD1182	Approved
0.7333	Intermediate Similarity	NPD2661	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD9568	Approved
0.7313	Intermediate Similarity	NPD2157	Approved
0.7311	Intermediate Similarity	NPD5451	Approved
0.7308	Intermediate Similarity	NPD4993	Discontinued
0.7305	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7596	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3110	Approved
0.7293	Intermediate Similarity	NPD3109	Approved
0.728	Intermediate Similarity	NPD1798	Approved
0.728	Intermediate Similarity	NPD1797	Approved
0.7279	Intermediate Similarity	NPD2161	Phase 2
0.7279	Intermediate Similarity	NPD3156	Discontinued
0.7273	Intermediate Similarity	NPD9379	Approved
0.7273	Intermediate Similarity	NPD9377	Approved
0.7273	Intermediate Similarity	NPD1039	Discontinued
0.7266	Intermediate Similarity	NPD9622	Approved
0.7246	Intermediate Similarity	NPD3060	Approved
0.7241	Intermediate Similarity	NPD4018	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD5356	Approved
0.7241	Intermediate Similarity	NPD5355	Approved
0.7226	Intermediate Similarity	NPD1375	Discontinued
0.7218	Intermediate Similarity	NPD7265	Discontinued
0.7206	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD6380	Phase 1
0.7203	Intermediate Similarity	NPD3687	Approved
0.7203	Intermediate Similarity	NPD3686	Approved
0.7203	Intermediate Similarity	NPD814	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD2559	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