NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	724.25
Volume:	690.151
LogP:	4.246
LogD:	3.746
LogS:	-4.099
# Rotatable Bonds:	4
TPSA:	161.06
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.193
Synthetic Accessibility Score:	5.311
Fsp3:	0.444
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.84
MDCK Permeability:	1.0107914931722917e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.07
Human Intestinal Absorption (HIA):	0.022
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.65

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	93.48084259033203%
Volume Distribution (VD):	0.335
Pgp-substrate:	7.859933376312256%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.073
CYP2C19-inhibitor:	0.48
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.82
CYP2C9-substrate:	0.858
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.262
CYP3A4-inhibitor:	0.967
CYP3A4-substrate:	0.543

ADMET: Excretion

Clearance (CL):	4.169
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.129
Human Hepatotoxicity (H-HT):	0.937
Drug-inuced Liver Injury (DILI):	0.972
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.709
Maximum Recommended Daily Dose:	0.954
Skin Sensitization:	0.363
Carcinogencity:	0.4
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.087

Download Data

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

Natural Product: NPC223393

Natural Product ID:	NPC223393
*Common Name:**	4,4'-(1E)-1,2-Ethenediylbis-1,2-Benzenediol
IUPAC Name:	4-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]benzene-1,2-diol
Synonyms:
Standard InCHIKey:	DZYRGJKHEGXOCR-OWOJBTEDSA-N
Standard InCHI:	InChI=1S/C14H12O4/c15-11-5-3-9(7-13(11)17)1-2-10-4-6-12(16)14(18)8-10/h1-8,15-18H/b2-1+
SMILES:	C(=Cc1ccc(c(c1)O)O)/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL99801
PubChem CID:	5468835
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
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	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
Others	3

Activity Type	# Activity
Individual Protein	1
NON-MOLECULAR	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	=	74000.0	nM	PMID[567259]
NPT35	Others	n.a.		INH	=	3.7	10'5L/mol/s	PMID[567260]
NPT35	Others	n.a.		TIME	=	0.85	hr	PMID[567260]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TIME	=	1.783	hr	PMID[567260]

☑ 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 NPC223393 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	368
0.1-0.2	2403
0.2-0.3	8705
0.3-0.4	11094
0.4-0.5	5258
0.5-0.6	8803
0.6-0.7	4322
0.7-0.8	1497
0.8-0.85	189
0.85-0.9	32
0.9-0.95	24
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC471511
0.9388	High Similarity	NPC239291
0.9368	High Similarity	NPC109955
0.9362	High Similarity	NPC107522
0.93	High Similarity	NPC34864
0.93	High Similarity	NPC58427
0.93	High Similarity	NPC114392
0.93	High Similarity	NPC105727
0.9271	High Similarity	NPC131587
0.9208	High Similarity	NPC254833
0.9208	High Similarity	NPC228343
0.92	High Similarity	NPC176527
0.9118	High Similarity	NPC174096
0.9118	High Similarity	NPC226401
0.9118	High Similarity	NPC120982
0.9118	High Similarity	NPC147634
0.9118	High Similarity	NPC79793
0.9109	High Similarity	NPC233835
0.9091	High Similarity	NPC52087
0.9082	High Similarity	NPC110764
0.9029	High Similarity	NPC268032
0.9029	High Similarity	NPC257430
0.9029	High Similarity	NPC179002
0.9029	High Similarity	NPC297657
0.9029	High Similarity	NPC187583
0.902	High Similarity	NPC62258
0.902	High Similarity	NPC55617
0.899	High Similarity	NPC477801
0.899	High Similarity	NPC477802
0.899	High Similarity	NPC196479
0.8958	High Similarity	NPC274678
0.8942	High Similarity	NPC51698
0.8911	High Similarity	NPC1786
0.8911	High Similarity	NPC294902
0.8911	High Similarity	NPC1075
0.89	High Similarity	NPC12278
0.89	High Similarity	NPC120719
0.89	High Similarity	NPC79672
0.8857	High Similarity	NPC471485
0.8774	High Similarity	NPC120280
0.8725	High Similarity	NPC19149
0.8725	High Similarity	NPC477814
0.8646	High Similarity	NPC45040
0.8611	High Similarity	NPC61062
0.8611	High Similarity	NPC277394
0.8611	High Similarity	NPC299252
0.86	High Similarity	NPC275053
0.86	High Similarity	NPC161571
0.86	High Similarity	NPC248573
0.8586	High Similarity	NPC32674
0.8585	High Similarity	NPC131530
0.8571	High Similarity	NPC222084
0.8532	High Similarity	NPC200988
0.8532	High Similarity	NPC145023
0.8532	High Similarity	NPC610
0.8532	High Similarity	NPC278652
0.8532	High Similarity	NPC293619
0.8532	High Similarity	NPC175799
0.8519	High Similarity	NPC472893
0.8495	Intermediate Similarity	NPC265146
0.8491	Intermediate Similarity	NPC226250
0.8485	Intermediate Similarity	NPC292730
0.8485	Intermediate Similarity	NPC132271
0.8485	Intermediate Similarity	NPC216520
0.8485	Intermediate Similarity	NPC82664
0.8476	Intermediate Similarity	NPC7097
0.8476	Intermediate Similarity	NPC36108
0.8476	Intermediate Similarity	NPC233731
0.8476	Intermediate Similarity	NPC246358
0.8469	Intermediate Similarity	NPC128062
0.8469	Intermediate Similarity	NPC151715
0.8469	Intermediate Similarity	NPC76938
0.8455	Intermediate Similarity	NPC275519
0.8455	Intermediate Similarity	NPC470626
0.8455	Intermediate Similarity	NPC86198
0.8455	Intermediate Similarity	NPC122009
0.8455	Intermediate Similarity	NPC144343
0.8447	Intermediate Similarity	NPC292452
0.8404	Intermediate Similarity	NPC175313
0.8404	Intermediate Similarity	NPC248817
0.8404	Intermediate Similarity	NPC150837
0.84	Intermediate Similarity	NPC291789
0.8384	Intermediate Similarity	NPC32714
0.8384	Intermediate Similarity	NPC26244
0.8378	Intermediate Similarity	NPC109371
0.8378	Intermediate Similarity	NPC263386
0.8378	Intermediate Similarity	NPC268572
0.8378	Intermediate Similarity	NPC141791
0.8378	Intermediate Similarity	NPC70084
0.8378	Intermediate Similarity	NPC470215
0.8378	Intermediate Similarity	NPC217174
0.8378	Intermediate Similarity	NPC470214
0.8378	Intermediate Similarity	NPC226629
0.8364	Intermediate Similarity	NPC86947
0.8364	Intermediate Similarity	NPC277588
0.8364	Intermediate Similarity	NPC283468
0.835	Intermediate Similarity	NPC474603
0.835	Intermediate Similarity	NPC30506
0.835	Intermediate Similarity	NPC12987
0.8333	Intermediate Similarity	NPC264558
0.8333	Intermediate Similarity	NPC95381
0.8333	Intermediate Similarity	NPC148969
0.8333	Intermediate Similarity	NPC27974
0.8333	Intermediate Similarity	NPC104216
0.8318	Intermediate Similarity	NPC8547
0.8318	Intermediate Similarity	NPC139617
0.8318	Intermediate Similarity	NPC78918
0.8318	Intermediate Similarity	NPC257124
0.8318	Intermediate Similarity	NPC156840
0.8318	Intermediate Similarity	NPC280382
0.8318	Intermediate Similarity	NPC173746
0.8317	Intermediate Similarity	NPC130193
0.8317	Intermediate Similarity	NPC92730
0.8316	Intermediate Similarity	NPC197783
0.8304	Intermediate Similarity	NPC252817
0.8304	Intermediate Similarity	NPC247364
0.8304	Intermediate Similarity	NPC165133
0.8304	Intermediate Similarity	NPC232084
0.8304	Intermediate Similarity	NPC10932
0.8304	Intermediate Similarity	NPC475245
0.8304	Intermediate Similarity	NPC232316
0.8304	Intermediate Similarity	NPC242885
0.8304	Intermediate Similarity	NPC117780
0.8304	Intermediate Similarity	NPC56214
0.8304	Intermediate Similarity	NPC265454
0.8304	Intermediate Similarity	NPC227217
0.8304	Intermediate Similarity	NPC95614
0.8304	Intermediate Similarity	NPC472071
0.8304	Intermediate Similarity	NPC61516
0.8304	Intermediate Similarity	NPC34634
0.83	Intermediate Similarity	NPC473388
0.8298	Intermediate Similarity	NPC124436
0.8257	Intermediate Similarity	NPC261453
0.8257	Intermediate Similarity	NPC33749
0.8257	Intermediate Similarity	NPC328593
0.8257	Intermediate Similarity	NPC217472
0.8241	Intermediate Similarity	NPC471179
0.8241	Intermediate Similarity	NPC146422
0.8235	Intermediate Similarity	NPC294741
0.823	Intermediate Similarity	NPC224814
0.823	Intermediate Similarity	NPC109083
0.823	Intermediate Similarity	NPC269843
0.823	Intermediate Similarity	NPC14007
0.823	Intermediate Similarity	NPC470848
0.823	Intermediate Similarity	NPC60962
0.823	Intermediate Similarity	NPC236520
0.823	Intermediate Similarity	NPC284078
0.823	Intermediate Similarity	NPC470414
0.823	Intermediate Similarity	NPC207613
0.823	Intermediate Similarity	NPC24125
0.823	Intermediate Similarity	NPC470849
0.823	Intermediate Similarity	NPC189844
0.823	Intermediate Similarity	NPC98305
0.823	Intermediate Similarity	NPC294361
0.8229	Intermediate Similarity	NPC184169
0.8229	Intermediate Similarity	NPC23167
0.8218	Intermediate Similarity	NPC201967
0.8218	Intermediate Similarity	NPC156313
0.8218	Intermediate Similarity	NPC225464
0.8214	Intermediate Similarity	NPC38483
0.8214	Intermediate Similarity	NPC176893
0.8214	Intermediate Similarity	NPC281298
0.8214	Intermediate Similarity	NPC191866
0.8214	Intermediate Similarity	NPC310338
0.819	Intermediate Similarity	NPC54765
0.8182	Intermediate Similarity	NPC474967
0.8182	Intermediate Similarity	NPC233669
0.8182	Intermediate Similarity	NPC4665
0.8173	Intermediate Similarity	NPC327811
0.8173	Intermediate Similarity	NPC323810
0.8173	Intermediate Similarity	NPC254965
0.8163	Intermediate Similarity	NPC192
0.8163	Intermediate Similarity	NPC312304
0.8163	Intermediate Similarity	NPC300017
0.8158	Intermediate Similarity	NPC343720
0.8158	Intermediate Similarity	NPC473853
0.8158	Intermediate Similarity	NPC262156
0.8158	Intermediate Similarity	NPC113865
0.8158	Intermediate Similarity	NPC237667
0.8158	Intermediate Similarity	NPC472271
0.8158	Intermediate Similarity	NPC324571
0.8158	Intermediate Similarity	NPC312675
0.8158	Intermediate Similarity	NPC160380
0.8158	Intermediate Similarity	NPC184651
0.8158	Intermediate Similarity	NPC147654
0.8158	Intermediate Similarity	NPC54872
0.8158	Intermediate Similarity	NPC470212
0.8158	Intermediate Similarity	NPC38996
0.8155	Intermediate Similarity	NPC100340
0.8155	Intermediate Similarity	NPC91461
0.8155	Intermediate Similarity	NPC143659
0.8155	Intermediate Similarity	NPC12221
0.8155	Intermediate Similarity	NPC7686
0.8155	Intermediate Similarity	NPC40258
0.8144	Intermediate Similarity	NPC25493
0.8144	Intermediate Similarity	NPC113460
0.8144	Intermediate Similarity	NPC19680
0.8137	Intermediate Similarity	NPC51333
0.8137	Intermediate Similarity	NPC275104
0.8137	Intermediate Similarity	NPC78119

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 NPC223393 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	347
0.1-0.2	1109
0.2-0.3	1556
0.3-0.4	2993
0.4-0.5	1760
0.5-0.6	1017
0.6-0.7	298
0.7-0.8	57
0.8-0.85	9
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9208	High Similarity	NPD3022	Approved
0.9208	High Similarity	NPD3021	Approved
0.86	High Similarity	NPD1242	Phase 1
0.8469	Intermediate Similarity	NPD2933	Approved
0.8469	Intermediate Similarity	NPD2934	Approved
0.8384	Intermediate Similarity	NPD2859	Approved
0.8384	Intermediate Similarity	NPD2860	Approved
0.8318	Intermediate Similarity	NPD228	Approved
0.8317	Intermediate Similarity	NPD3020	Approved
0.8298	Intermediate Similarity	NPD111	Approved
0.8241	Intermediate Similarity	NPD9379	Approved
0.8241	Intermediate Similarity	NPD9377	Approved
0.8224	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.8017	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD2337	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD844	Approved
0.7797	Intermediate Similarity	NPD5310	Approved
0.7797	Intermediate Similarity	NPD5311	Approved
0.7767	Intermediate Similarity	NPD288	Approved
0.7731	Intermediate Similarity	NPD3055	Approved
0.7731	Intermediate Similarity	NPD3053	Approved
0.7714	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7679	Intermediate Similarity	NPD5283	Phase 1
0.7672	Intermediate Similarity	NPD9381	Approved
0.7672	Intermediate Similarity	NPD9384	Approved
0.7623	Intermediate Similarity	NPD3027	Phase 3
0.7603	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD3028	Approved
0.75	Intermediate Similarity	NPD9634	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9094	Approved
0.7477	Intermediate Similarity	NPD940	Approved
0.7477	Intermediate Similarity	NPD846	Approved
0.7455	Intermediate Similarity	NPD2342	Discontinued
0.744	Intermediate Similarity	NPD3062	Approved
0.744	Intermediate Similarity	NPD943	Approved
0.744	Intermediate Similarity	NPD3059	Approved
0.744	Intermediate Similarity	NPD3061	Approved
0.744	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD1613	Approved
0.7419	Intermediate Similarity	NPD2028	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD9622	Approved
0.7414	Intermediate Similarity	NPD5536	Phase 2
0.7377	Intermediate Similarity	NPD258	Approved
0.7377	Intermediate Similarity	NPD257	Approved
0.7364	Intermediate Similarity	NPD968	Approved
0.7333	Intermediate Similarity	NPD1809	Phase 2
0.7323	Intermediate Similarity	NPD5314	Approved
0.7321	Intermediate Similarity	NPD1792	Phase 2
0.7317	Intermediate Similarity	NPD9569	Approved
0.7312	Intermediate Similarity	NPD9087	Approved
0.7308	Intermediate Similarity	NPD845	Approved
0.7302	Intermediate Similarity	NPD1558	Phase 1
0.7288	Intermediate Similarity	NPD1357	Approved
0.7281	Intermediate Similarity	NPD7635	Approved
0.725	Intermediate Similarity	NPD3092	Approved
0.7248	Intermediate Similarity	NPD9500	Approved
0.7238	Intermediate Similarity	NPD9296	Approved
0.7236	Intermediate Similarity	NPD9619	Approved
0.7236	Intermediate Similarity	NPD9621	Approved
0.7236	Intermediate Similarity	NPD9620	Approved
0.7227	Intermediate Similarity	NPD2286	Discontinued
0.7217	Intermediate Similarity	NPD2234	Approved
0.7217	Intermediate Similarity	NPD2229	Approved
0.7217	Intermediate Similarity	NPD2228	Approved
0.7207	Intermediate Similarity	NPD1445	Approved
0.7207	Intermediate Similarity	NPD1444	Approved
0.7203	Intermediate Similarity	NPD3091	Approved
0.719	Intermediate Similarity	NPD9269	Phase 2
0.7188	Intermediate Similarity	NPD9088	Approved
0.7182	Intermediate Similarity	NPD9610	Approved
0.7182	Intermediate Similarity	NPD9608	Approved
0.7177	Intermediate Similarity	NPD9494	Approved
0.7168	Intermediate Similarity	NPD4750	Phase 3
0.7154	Intermediate Similarity	NPD1632	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3094	Phase 2
0.7143	Intermediate Similarity	NPD4093	Discontinued
0.7131	Intermediate Similarity	NPD2982	Phase 2
0.7131	Intermediate Similarity	NPD2983	Phase 2
0.7131	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7266	Discontinued
0.7087	Intermediate Similarity	NPD259	Phase 1
0.7083	Intermediate Similarity	NPD3019	Approved
0.7083	Intermediate Similarity	NPD4059	Approved
0.7083	Intermediate Similarity	NPD2932	Approved
0.7063	Intermediate Similarity	NPD9537	Phase 1
0.7063	Intermediate Similarity	NPD9536	Phase 1
0.7049	Intermediate Similarity	NPD2981	Phase 2
0.7037	Intermediate Similarity	NPD9273	Approved
0.7031	Intermediate Similarity	NPD826	Approved
0.7031	Intermediate Similarity	NPD3620	Phase 2
0.7031	Intermediate Similarity	NPD825	Approved
0.7031	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD4339	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD3145	Approved
0.7008	Intermediate Similarity	NPD601	Approved
0.7008	Intermediate Similarity	NPD3144	Approved
0.7008	Intermediate Similarity	NPD598	Approved
0.7008	Intermediate Similarity	NPD597	Approved
0.6977	Remote Similarity	NPD555	Phase 2
0.6977	Remote Similarity	NPD275	Approved
0.6977	Remote Similarity	NPD274	Approved
0.697	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6953	Remote Similarity	NPD2674	Phase 3
0.6953	Remote Similarity	NPD1136	Approved
0.6953	Remote Similarity	NPD1130	Approved
0.6953	Remote Similarity	NPD1132	Approved
0.6949	Remote Similarity	NPD6671	Approved
0.6942	Remote Similarity	NPD3095	Discontinued
0.6942	Remote Similarity	NPD1751	Approved
0.693	Remote Similarity	NPD2684	Approved
0.6923	Remote Similarity	NPD817	Approved
0.6923	Remote Similarity	NPD823	Approved
0.6917	Remote Similarity	NPD1548	Phase 1
0.6907	Remote Similarity	NPD9294	Approved
0.6905	Remote Similarity	NPD3018	Phase 2
0.69	Remote Similarity	NPD9089	Approved
0.6899	Remote Similarity	NPD4060	Phase 1
0.6889	Remote Similarity	NPD6190	Approved
0.6864	Remote Similarity	NPD497	Approved
0.6864	Remote Similarity	NPD9618	Approved
0.6864	Remote Similarity	NPD9614	Approved
0.6864	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.686	Remote Similarity	NPD9268	Approved
0.6846	Remote Similarity	NPD230	Phase 1
0.6842	Remote Similarity	NPD290	Approved
0.6842	Remote Similarity	NPD9265	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD7843	Approved
0.6829	Remote Similarity	NPD1201	Approved
0.6829	Remote Similarity	NPD1535	Discovery
0.6829	Remote Similarity	NPD1610	Phase 2
0.6825	Remote Similarity	NPD6584	Phase 3
0.6818	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD8166	Discontinued
0.6807	Remote Similarity	NPD7157	Approved
0.6807	Remote Similarity	NPD709	Approved
0.6803	Remote Similarity	NPD4589	Approved
0.6803	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.68	Remote Similarity	NPD9093	Approved
0.6797	Remote Similarity	NPD7095	Approved
0.6788	Remote Similarity	NPD1511	Approved
0.678	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.678	Remote Similarity	NPD496	Approved
0.678	Remote Similarity	NPD495	Approved
0.678	Remote Similarity	NPD498	Approved
0.6777	Remote Similarity	NPD5303	Approved
0.6777	Remote Similarity	NPD1182	Approved
0.6777	Remote Similarity	NPD5304	Approved
0.6777	Remote Similarity	NPD2226	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1481	Phase 2
0.6772	Remote Similarity	NPD2861	Phase 2
0.6767	Remote Similarity	NPD9570	Approved
0.6752	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.675	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6748	Remote Similarity	NPD1981	Approved
0.6748	Remote Similarity	NPD1980	Approved
0.6748	Remote Similarity	NPD3421	Phase 3
0.6748	Remote Similarity	NPD1983	Approved
0.6746	Remote Similarity	NPD1470	Approved
0.6741	Remote Similarity	NPD3060	Approved
0.6724	Remote Similarity	NPD5451	Approved
0.6723	Remote Similarity	NPD1793	Approved
0.6723	Remote Similarity	NPD1791	Approved
0.6723	Remote Similarity	NPD475	Phase 2
0.6715	Remote Similarity	NPD2422	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3845	Phase 1
0.6696	Remote Similarity	NPD1358	Approved
0.6696	Remote Similarity	NPD291	Approved
0.6695	Remote Similarity	NPD5535	Approved
0.6694	Remote Similarity	NPD9613	Approved
0.6694	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD9616	Approved
0.6694	Remote Similarity	NPD9615	Approved
0.6691	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD5846	Approved
0.6667	Remote Similarity	NPD256	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD2420	Approved
0.6667	Remote Similarity	NPD6516	Phase 2
0.6667	Remote Similarity	NPD2922	Phase 1
0.6667	Remote Similarity	NPD2421	Approved
0.6667	Remote Similarity	NPD255	Approved
0.6641	Remote Similarity	NPD5736	Approved
0.664	Remote Similarity	NPD2562	Approved
0.664	Remote Similarity	NPD2561	Approved
0.6639	Remote Similarity	NPD7159	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD316	Approved
0.6615	Remote Similarity	NPD5109	Approved
0.6615	Remote Similarity	NPD5111	Phase 2
0.6615	Remote Similarity	NPD5110	Phase 2
0.6614	Remote Similarity	NPD1164	Approved
0.6613	Remote Similarity	NPD3026	Approved
0.6613	Remote Similarity	NPD3847	Discontinued
0.6613	Remote Similarity	NPD3023	Approved
0.6612	Remote Similarity	NPD9568	Approved
0.6612	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD9295	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