NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.1
Volume:	250.009
LogP:	3.797
LogD:	3.78
LogS:	-3.639
# Rotatable Bonds:	3
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.811
Synthetic Accessibility Score:	1.71
Fsp3:	0.067
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.833
MDCK Permeability:	1.6609843441983685e-05
Pgp-inhibitor:	0.786
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.364
Plasma Protein Binding (PPB):	98.57247161865234%
Volume Distribution (VD):	1.162
Pgp-substrate:	1.2995632886886597%

ADMET: Metabolism

CYP1A2-inhibitor:	0.975
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.863
CYP2C19-substrate:	0.324
CYP2C9-inhibitor:	0.439
CYP2C9-substrate:	0.952
CYP2D6-inhibitor:	0.668
CYP2D6-substrate:	0.936
CYP3A4-inhibitor:	0.745
CYP3A4-substrate:	0.463

ADMET: Excretion

Clearance (CL):	11.969
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.473
Human Hepatotoxicity (H-HT):	0.512
Drug-inuced Liver Injury (DILI):	0.127
AMES Toxicity:	0.84
Rat Oral Acute Toxicity:	0.041
Maximum Recommended Daily Dose:	0.109
Skin Sensitization:	0.959
Carcinogencity:	0.398
Eye Corrosion:	0.022
Eye Irritation:	0.976
Respiratory Toxicity:	0.494

Download Data

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

Natural Product: NPC474603

Natural Product ID:	NPC474603
*Common Name:**	(E)-5-Methoxy-4'-Stilbenol
IUPAC Name:	4-[(E)-2-(3-methoxyphenyl)ethenyl]phenol
Synonyms:
Standard InCHIKey:	ZVJLZUWCAUTTBS-AATRIKPKSA-N
Standard InCHI:	InChI=1S/C15H14O2/c1-17-15-4-2-3-13(11-15)6-5-12-7-9-14(16)10-8-12/h2-11,16H,1H3/b6-5+
SMILES:	COc1cccc(c1)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL476678
PubChem CID:	5930975
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

*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
NPO33038	plagiochila stephensoniana	Species	Plagiochilaceae	Eukaryota	n.a.	New Zealand	n.a.	PMID[8254344]

☑ 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
EC50	1
IC50	6
MIC	2
Others	17

Activity Type	# Activity
Cell Line	4
Individual Protein	5
Organism	14
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	9.9	ug.mL-1	PMID[490022]
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	24.0	ug.mL-1	PMID[490024]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	21.0	ug.mL-1	PMID[490024]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	26.0	ug.mL-1	PMID[490024]
NPT472	Individual Protein	Vanilloid receptor	Homo sapiens	IC50	>	10000.0	nM	PMID[490025]
NPT472	Individual Protein	Vanilloid receptor	Homo sapiens	Efficacy	<	10.0	%	PMID[490025]
NPT1534	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Rattus norvegicus	Efficacy	=	41.8	%	PMID[490025]
NPT1534	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Rattus norvegicus	EC50	=	6600.0	nM	PMID[490025]
NPT1534	Individual Protein	Transient receptor potential cation channel subfamily A member 1	Rattus norvegicus	IC50	=	10100.0	nM	PMID[490025]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	31.25	ug.mL-1	PMID[490022]
NPT20	Organism	Candida albicans	Candida albicans	MFC	=	125.0	ug ml-1	PMID[490022]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	=	31.25	ug.mL-1	PMID[490022]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MFC	=	31.25	ug ml-1	PMID[490022]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	2.0	mm	PMID[490022]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	4.0	mm	PMID[490022]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	6.0	mm	PMID[490022]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	2.0	mm	PMID[490022]
NPT20	Organism	Candida albicans	Candida albicans	IZ	=	7.0	mm	PMID[490022]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	2.0	mm	PMID[490022]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	8.0	mm	PMID[490022]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	6.0	mm	PMID[490022]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	IZ	=	10.0	mm	PMID[490022]
NPT1223	Organism	Amorphotheca resinae	Amorphotheca resinae	IZ	=	2.0	mm	PMID[490022]
NPT35	Others	n.a.		LogP	=	3.14	n.a.	PMID[490023]
NPT27	Others	Unspecified		Ratio IC50	=	0.9	n.a.	PMID[490024]
NPT27	Others	Unspecified		Ratio IC50	=	1.1	n.a.	PMID[490024]

☑ 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 NPC474603 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	302
0.1-0.2	2414
0.2-0.3	7332
0.3-0.4	11697
0.4-0.5	4033
0.5-0.6	7317
0.6-0.7	6941
0.7-0.8	2268
0.8-0.85	316
0.85-0.9	65
0.9-0.95	9
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC12987
0.96	High Similarity	NPC75440
0.932	High Similarity	NPC90520
0.932	High Similarity	NPC296920
0.9231	High Similarity	NPC280606
0.9216	High Similarity	NPC201959
0.9208	High Similarity	NPC113457
0.9057	High Similarity	NPC180508
0.9057	High Similarity	NPC228287
0.9038	High Similarity	NPC94045
0.8942	High Similarity	NPC246358
0.8942	High Similarity	NPC7097
0.8942	High Similarity	NPC36108
0.8942	High Similarity	NPC233731
0.8889	High Similarity	NPC141090
0.8889	High Similarity	NPC203113
0.8824	High Similarity	NPC241224
0.8812	High Similarity	NPC300166
0.8807	High Similarity	NPC195466
0.8807	High Similarity	NPC293619
0.8807	High Similarity	NPC474933
0.88	High Similarity	NPC100870
0.8785	High Similarity	NPC141003
0.8785	High Similarity	NPC35344
0.8774	High Similarity	NPC139617
0.8774	High Similarity	NPC173746
0.8774	High Similarity	NPC78918
0.8774	High Similarity	NPC156840
0.8774	High Similarity	NPC8547
0.8774	High Similarity	NPC257124
0.875	High Similarity	NPC233320
0.875	High Similarity	NPC177844
0.875	High Similarity	NPC8002
0.875	High Similarity	NPC227894
0.875	High Similarity	NPC99886
0.875	High Similarity	NPC259134
0.8727	High Similarity	NPC470626
0.8725	High Similarity	NPC305205
0.8704	High Similarity	NPC276737
0.8704	High Similarity	NPC22610
0.8687	High Similarity	NPC274678
0.866	High Similarity	NPC71853
0.8654	High Similarity	NPC164576
0.8649	High Similarity	NPC310338
0.8649	High Similarity	NPC281298
0.8649	High Similarity	NPC226629
0.8627	High Similarity	NPC310905
0.8627	High Similarity	NPC51633
0.8627	High Similarity	NPC12714
0.8624	High Similarity	NPC808
0.8624	High Similarity	NPC53906
0.8624	High Similarity	NPC167934
0.8598	High Similarity	NPC255068
0.8598	High Similarity	NPC266932
0.8585	High Similarity	NPC82016
0.8585	High Similarity	NPC474272
0.8571	High Similarity	NPC117780
0.8571	High Similarity	NPC474565
0.8571	High Similarity	NPC61516
0.8571	High Similarity	NPC321956
0.8571	High Similarity	NPC165133
0.8571	High Similarity	NPC227217
0.8571	High Similarity	NPC247364
0.8571	High Similarity	NPC95614
0.8571	High Similarity	NPC56214
0.8571	High Similarity	NPC242885
0.8571	High Similarity	NPC232316
0.8571	High Similarity	NPC103916
0.8571	High Similarity	NPC232084
0.8571	High Similarity	NPC10932
0.8558	High Similarity	NPC288760
0.8545	High Similarity	NPC150624
0.8544	High Similarity	NPC192596
0.8505	High Similarity	NPC137685
0.8505	High Similarity	NPC475852
0.8496	Intermediate Similarity	NPC166759
0.8496	Intermediate Similarity	NPC109083
0.8496	Intermediate Similarity	NPC60962
0.8496	Intermediate Similarity	NPC189844
0.8496	Intermediate Similarity	NPC269843
0.8496	Intermediate Similarity	NPC102639
0.8496	Intermediate Similarity	NPC224814
0.8496	Intermediate Similarity	NPC207613
0.8496	Intermediate Similarity	NPC14007
0.8496	Intermediate Similarity	NPC129176
0.8491	Intermediate Similarity	NPC241549
0.8468	Intermediate Similarity	NPC15860
0.8468	Intermediate Similarity	NPC470759
0.8468	Intermediate Similarity	NPC86947
0.8468	Intermediate Similarity	NPC219070
0.8468	Intermediate Similarity	NPC69261
0.8468	Intermediate Similarity	NPC33270
0.8468	Intermediate Similarity	NPC221549
0.8468	Intermediate Similarity	NPC244816
0.8468	Intermediate Similarity	NPC127894
0.8468	Intermediate Similarity	NPC50521
0.8468	Intermediate Similarity	NPC280001
0.8462	Intermediate Similarity	NPC292792
0.8462	Intermediate Similarity	NPC108875
0.8462	Intermediate Similarity	NPC38079
0.8462	Intermediate Similarity	NPC2518
0.8455	Intermediate Similarity	NPC301321
0.8455	Intermediate Similarity	NPC185541
0.8455	Intermediate Similarity	NPC296526
0.8455	Intermediate Similarity	NPC464
0.8426	Intermediate Similarity	NPC55300
0.8426	Intermediate Similarity	NPC195873
0.8426	Intermediate Similarity	NPC275627
0.8421	Intermediate Similarity	NPC54872
0.8421	Intermediate Similarity	NPC312675
0.8421	Intermediate Similarity	NPC324571
0.8421	Intermediate Similarity	NPC262156
0.8421	Intermediate Similarity	NPC184651
0.8421	Intermediate Similarity	NPC38996
0.8421	Intermediate Similarity	NPC113865
0.8421	Intermediate Similarity	NPC343720
0.8421	Intermediate Similarity	NPC473853
0.8421	Intermediate Similarity	NPC476633
0.8421	Intermediate Similarity	NPC470212
0.8421	Intermediate Similarity	NPC160380
0.84	Intermediate Similarity	NPC471581
0.8396	Intermediate Similarity	NPC35543
0.8396	Intermediate Similarity	NPC251306
0.8393	Intermediate Similarity	NPC63010
0.8393	Intermediate Similarity	NPC190514
0.8393	Intermediate Similarity	NPC474214
0.8393	Intermediate Similarity	NPC474040
0.8384	Intermediate Similarity	NPC45040
0.8381	Intermediate Similarity	NPC8302
0.8381	Intermediate Similarity	NPC154899
0.8381	Intermediate Similarity	NPC470393
0.8381	Intermediate Similarity	NPC233396
0.8378	Intermediate Similarity	NPC54507
0.8378	Intermediate Similarity	NPC85292
0.8378	Intermediate Similarity	NPC229147
0.8378	Intermediate Similarity	NPC114064
0.8378	Intermediate Similarity	NPC19290
0.8378	Intermediate Similarity	NPC221049
0.8364	Intermediate Similarity	NPC470837
0.835	Intermediate Similarity	NPC223393
0.835	Intermediate Similarity	NPC161571
0.835	Intermediate Similarity	NPC275053
0.835	Intermediate Similarity	NPC248573
0.8349	Intermediate Similarity	NPC165646
0.8349	Intermediate Similarity	NPC474920
0.8348	Intermediate Similarity	NPC30462
0.8348	Intermediate Similarity	NPC71579
0.8348	Intermediate Similarity	NPC85488
0.8348	Intermediate Similarity	NPC41562
0.8348	Intermediate Similarity	NPC473411
0.8348	Intermediate Similarity	NPC262253
0.8333	Intermediate Similarity	NPC32674
0.8333	Intermediate Similarity	NPC175298
0.8333	Intermediate Similarity	NPC470161
0.8333	Intermediate Similarity	NPC248817
0.8333	Intermediate Similarity	NPC168657
0.8333	Intermediate Similarity	NPC150837
0.8319	Intermediate Similarity	NPC163036
0.8319	Intermediate Similarity	NPC474320
0.8319	Intermediate Similarity	NPC184302
0.8318	Intermediate Similarity	NPC169450
0.8318	Intermediate Similarity	NPC245115
0.8317	Intermediate Similarity	NPC26244
0.8304	Intermediate Similarity	NPC39793
0.8304	Intermediate Similarity	NPC164386
0.8304	Intermediate Similarity	NPC259638
0.8302	Intermediate Similarity	NPC92623
0.8302	Intermediate Similarity	NPC135464
0.8286	Intermediate Similarity	NPC130817
0.8276	Intermediate Similarity	NPC84086
0.8276	Intermediate Similarity	NPC317769
0.8276	Intermediate Similarity	NPC31344
0.8276	Intermediate Similarity	NPC280704
0.8276	Intermediate Similarity	NPC282496
0.8276	Intermediate Similarity	NPC160900
0.8276	Intermediate Similarity	NPC471693
0.8276	Intermediate Similarity	NPC229084
0.8276	Intermediate Similarity	NPC18984
0.8276	Intermediate Similarity	NPC228922
0.8276	Intermediate Similarity	NPC106659
0.8276	Intermediate Similarity	NPC136319
0.8276	Intermediate Similarity	NPC249788
0.8276	Intermediate Similarity	NPC233526
0.8276	Intermediate Similarity	NPC197757
0.8273	Intermediate Similarity	NPC165106
0.8269	Intermediate Similarity	NPC94343
0.8265	Intermediate Similarity	NPC104216
0.8265	Intermediate Similarity	NPC27974
0.8261	Intermediate Similarity	NPC290451
0.8261	Intermediate Similarity	NPC127389
0.8252	Intermediate Similarity	NPC171843
0.8252	Intermediate Similarity	NPC92730
0.8247	Intermediate Similarity	NPC197783
0.8246	Intermediate Similarity	NPC2058
0.8235	Intermediate Similarity	NPC473388
0.8235	Intermediate Similarity	NPC132271
0.8235	Intermediate Similarity	NPC82664
0.8235	Intermediate Similarity	NPC216520
0.8235	Intermediate Similarity	NPC292730
0.823	Intermediate Similarity	NPC255675

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 NPC474603 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	304
0.1-0.2	1160
0.2-0.3	1404
0.3-0.4	2662
0.4-0.5	1820
0.5-0.6	1034
0.6-0.7	619
0.7-0.8	130
0.8-0.85	15
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8774	High Similarity	NPD228	Approved
0.8654	High Similarity	NPD968	Approved
0.84	Intermediate Similarity	NPD2933	Approved
0.84	Intermediate Similarity	NPD2934	Approved
0.835	Intermediate Similarity	NPD1242	Phase 1
0.8317	Intermediate Similarity	NPD2859	Approved
0.8317	Intermediate Similarity	NPD2860	Approved
0.8276	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD5283	Phase 1
0.8252	Intermediate Similarity	NPD3020	Approved
0.8229	Intermediate Similarity	NPD111	Approved
0.8125	Intermediate Similarity	NPD6671	Approved
0.8081	Intermediate Similarity	NPD9295	Approved
0.8073	Intermediate Similarity	NPD5451	Approved
0.807	Intermediate Similarity	NPD1548	Phase 1
0.8067	Intermediate Similarity	NPD6584	Phase 3
0.8	Intermediate Similarity	NPD1357	Approved
0.7982	Intermediate Similarity	NPD5536	Phase 2
0.7982	Intermediate Similarity	NPD2684	Approved
0.7965	Intermediate Similarity	NPD709	Approved
0.7949	Intermediate Similarity	NPD1610	Phase 2
0.7913	Intermediate Similarity	NPD1182	Approved
0.7909	Intermediate Similarity	NPD3021	Approved
0.7909	Intermediate Similarity	NPD3022	Approved
0.7899	Intermediate Similarity	NPD1283	Approved
0.789	Intermediate Similarity	NPD290	Approved
0.7869	Intermediate Similarity	NPD3027	Phase 3
0.7864	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD821	Approved
0.7851	Intermediate Similarity	NPD2861	Phase 2
0.7845	Intermediate Similarity	NPD1651	Approved
0.7815	Intermediate Similarity	NPD6583	Phase 3
0.7815	Intermediate Similarity	NPD1669	Approved
0.7815	Intermediate Similarity	NPD6582	Phase 2
0.7798	Intermediate Similarity	NPD3134	Approved
0.7788	Intermediate Similarity	NPD844	Approved
0.7778	Intermediate Similarity	NPD4626	Approved
0.7778	Intermediate Similarity	NPD2668	Approved
0.7778	Intermediate Similarity	NPD2667	Approved
0.7731	Intermediate Similarity	NPD2230	Approved
0.7731	Intermediate Similarity	NPD2233	Approved
0.7731	Intermediate Similarity	NPD2232	Approved
0.7727	Intermediate Similarity	NPD1358	Approved
0.7714	Intermediate Similarity	NPD288	Approved
0.7712	Intermediate Similarity	NPD3847	Discontinued
0.7699	Intermediate Similarity	NPD7843	Approved
0.7699	Intermediate Similarity	NPD5535	Approved
0.7692	Intermediate Similarity	NPD9296	Approved
0.768	Intermediate Similarity	NPD4060	Phase 1
0.7667	Intermediate Similarity	NPD2983	Phase 2
0.7667	Intermediate Similarity	NPD2982	Phase 2
0.7664	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD7157	Approved
0.7647	Intermediate Similarity	NPD1535	Discovery
0.7647	Intermediate Similarity	NPD1281	Approved
0.7642	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7642	Intermediate Similarity	NPD4908	Phase 1
0.7623	Intermediate Similarity	NPD4624	Approved
0.7607	Intermediate Similarity	NPD1894	Discontinued
0.7583	Intermediate Similarity	NPD2981	Phase 2
0.7583	Intermediate Similarity	NPD1481	Phase 2
0.7583	Intermediate Similarity	NPD2235	Phase 2
0.7583	Intermediate Similarity	NPD1608	Approved
0.7583	Intermediate Similarity	NPD2231	Phase 2
0.7583	Intermediate Similarity	NPD1840	Phase 2
0.7561	Intermediate Similarity	NPD9494	Approved
0.7561	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD5585	Approved
0.754	Intermediate Similarity	NPD1613	Approved
0.754	Intermediate Similarity	NPD1558	Phase 1
0.754	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.752	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD422	Phase 1
0.7479	Intermediate Similarity	NPD2423	Clinical (unspecified phase)
0.7479	Intermediate Similarity	NPD6516	Phase 2
0.7479	Intermediate Similarity	NPD1778	Approved
0.7479	Intermediate Similarity	NPD5846	Approved
0.7478	Intermediate Similarity	NPD1241	Discontinued
0.744	Intermediate Similarity	NPD7095	Approved
0.744	Intermediate Similarity	NPD4625	Phase 3
0.7436	Intermediate Similarity	NPD3596	Phase 2
0.7431	Intermediate Similarity	NPD940	Approved
0.7431	Intermediate Similarity	NPD846	Approved
0.7419	Intermediate Similarity	NPD3018	Phase 2
0.7417	Intermediate Similarity	NPD3496	Discontinued
0.7404	Intermediate Similarity	NPD9365	Approved
0.7402	Intermediate Similarity	NPD3620	Phase 2
0.7402	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD5691	Approved
0.7385	Intermediate Similarity	NPD2935	Discontinued
0.7381	Intermediate Similarity	NPD3145	Approved
0.7381	Intermediate Similarity	NPD3144	Approved
0.7377	Intermediate Similarity	NPD5327	Phase 3
0.7377	Intermediate Similarity	NPD4749	Approved
0.7339	Intermediate Similarity	NPD3028	Approved
0.7333	Intermediate Similarity	NPD17	Approved
0.7323	Intermediate Similarity	NPD2674	Phase 3
0.7311	Intermediate Similarity	NPD6580	Approved
0.7311	Intermediate Similarity	NPD6581	Approved
0.7311	Intermediate Similarity	NPD3091	Approved
0.729	Intermediate Similarity	NPD1809	Phase 2
0.7287	Intermediate Similarity	NPD4097	Suspended
0.7281	Intermediate Similarity	NPD1792	Phase 2
0.728	Intermediate Similarity	NPD4993	Discontinued
0.7266	Intermediate Similarity	NPD1240	Approved
0.7266	Intermediate Similarity	NPD4140	Approved
0.7266	Intermediate Similarity	NPD2238	Phase 2
0.7264	Intermediate Similarity	NPD845	Approved
0.7257	Intermediate Similarity	NPD2342	Discontinued
0.725	Intermediate Similarity	NPD6830	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD7635	Approved
0.7236	Intermediate Similarity	NPD4359	Approved
0.7236	Intermediate Similarity	NPD3676	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD9697	Approved
0.7222	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD3060	Approved
0.7213	Intermediate Similarity	NPD1611	Approved
0.7209	Intermediate Similarity	NPD5735	Approved
0.7207	Intermediate Similarity	NPD9500	Approved
0.7203	Intermediate Similarity	NPD2557	Approved
0.72	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2107	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD2228	Approved
0.7179	Intermediate Similarity	NPD1398	Phase 1
0.7179	Intermediate Similarity	NPD2234	Approved
0.7179	Intermediate Similarity	NPD2229	Approved
0.7177	Intermediate Similarity	NPD1876	Approved
0.7177	Intermediate Similarity	NPD2922	Phase 1
0.7168	Intermediate Similarity	NPD1445	Approved
0.7168	Intermediate Similarity	NPD1444	Approved
0.7167	Intermediate Similarity	NPD9545	Approved
0.7165	Intermediate Similarity	NPD5163	Phase 2
0.7154	Intermediate Similarity	NPD1244	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6353	Approved
0.7154	Intermediate Similarity	NPD3054	Approved
0.7154	Intermediate Similarity	NPD3972	Approved
0.7154	Intermediate Similarity	NPD3052	Approved
0.7154	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD1607	Approved
0.7143	Intermediate Similarity	NPD9610	Approved
0.7143	Intermediate Similarity	NPD9608	Approved
0.7143	Intermediate Similarity	NPD2407	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7037	Approved
0.7132	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.713	Intermediate Similarity	NPD4750	Phase 3
0.712	Intermediate Similarity	NPD1203	Approved
0.712	Intermediate Similarity	NPD2797	Approved
0.7117	Intermediate Similarity	NPD291	Approved
0.7109	Intermediate Similarity	NPD6798	Discontinued
0.7109	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD5718	Phase 2
0.7109	Intermediate Similarity	NPD5109	Approved
0.7109	Intermediate Similarity	NPD5110	Phase 2
0.7109	Intermediate Similarity	NPD5111	Phase 2
0.7109	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD1039	Discontinued
0.7107	Intermediate Similarity	NPD4093	Discontinued
0.7107	Intermediate Similarity	NPD3443	Approved
0.7107	Intermediate Similarity	NPD3444	Approved
0.7107	Intermediate Similarity	NPD3445	Approved
0.7097	Intermediate Similarity	NPD3685	Discontinued
0.7094	Intermediate Similarity	NPD9379	Approved
0.7094	Intermediate Similarity	NPD1138	Approved
0.7094	Intermediate Similarity	NPD9377	Approved
0.7087	Intermediate Similarity	NPD596	Approved
0.7087	Intermediate Similarity	NPD600	Approved
0.7083	Intermediate Similarity	NPD9087	Approved
0.7077	Intermediate Similarity	NPD6355	Discontinued
0.7073	Intermediate Similarity	NPD1091	Approved
0.7073	Intermediate Similarity	NPD776	Approved
0.7073	Intermediate Similarity	NPD3705	Approved
0.7073	Intermediate Similarity	NPD3092	Approved
0.7063	Intermediate Similarity	NPD3691	Phase 2
0.7063	Intermediate Similarity	NPD3690	Phase 2
0.7063	Intermediate Similarity	NPD7905	Discontinued
0.7059	Intermediate Similarity	NPD6387	Discontinued
0.7054	Intermediate Similarity	NPD4062	Phase 3
0.7054	Intermediate Similarity	NPD6233	Phase 2
0.7049	Intermediate Similarity	NPD4059	Approved
0.7049	Intermediate Similarity	NPD2286	Discontinued
0.7049	Intermediate Similarity	NPD2932	Approved
0.7049	Intermediate Similarity	NPD3019	Approved
0.7045	Intermediate Similarity	NPD1510	Phase 2
0.7045	Intermediate Similarity	NPD4108	Discontinued
0.704	Intermediate Similarity	NPD7258	Clinical (unspecified phase)
0.704	Intermediate Similarity	NPD3225	Approved
0.704	Intermediate Similarity	NPD6696	Suspended
0.7031	Intermediate Similarity	NPD1024	Discontinued
0.7009	Intermediate Similarity	NPD1139	Approved
0.7009	Intermediate Similarity	NPD1137	Approved
0.7008	Intermediate Similarity	NPD1712	Approved
0.7007	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD7041	Phase 2
0.7	Intermediate Similarity	NPD9493	Approved
0.7	Intermediate Similarity	NPD7340	Approved
0.7	Intermediate Similarity	NPD2979	Phase 3
0.6985	Remote Similarity	NPD5241	Discontinued
0.6984	Remote Similarity	NPD1232	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD987	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