NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.09
Volume:	273.458
LogP:	3.494
LogD:	4.408
LogS:	-3.261
# Rotatable Bonds:	5
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.673
Synthetic Accessibility Score:	1.707
Fsp3:	0.062
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:	-4.696
MDCK Permeability:	2.517848406569101e-05
Pgp-inhibitor:	0.064
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.043

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.566
Plasma Protein Binding (PPB):	97.17552947998047%
Volume Distribution (VD):	0.672
Pgp-substrate:	3.026973009109497%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.966
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.865
CYP2C9-substrate:	0.815
CYP2D6-inhibitor:	0.575
CYP2D6-substrate:	0.657
CYP3A4-inhibitor:	0.126
CYP3A4-substrate:	0.321

ADMET: Excretion

Clearance (CL):	13.658
Half-life (T1/2):	0.912

ADMET: Toxicity

hERG Blockers:	0.231
Human Hepatotoxicity (H-HT):	0.065
Drug-inuced Liver Injury (DILI):	0.066
AMES Toxicity:	0.508
Rat Oral Acute Toxicity:	0.271
Maximum Recommended Daily Dose:	0.144
Skin Sensitization:	0.948
Carcinogencity:	0.24
Eye Corrosion:	0.009
Eye Irritation:	0.835
Respiratory Toxicity:	0.11

Download Data

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

Natural Product: NPC206341

Natural Product ID:	NPC206341
*Common Name:**	Benzyl (E)-P-Coumarate
IUPAC Name:	benzyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms:	Benzyl (E)-P-Coumarate; Benzyl 3-(4-Hydroxyphenyl)Acrylate
Standard InCHIKey:	RGZZCZQQPNJCPO-DHZHZOJOSA-N
Standard InCHI:	InChI=1S/C16H14O3/c17-15-9-6-13(7-10-15)8-11-16(18)19-12-14-4-2-1-3-5-14/h1-11,17H,12H2/b11-8+
SMILES:	O=C(OCc1ccccc1)/C=C/c1ccc(cc1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095574
PubChem CID:	10083644
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0003002] Hydroxycinnamic acid esters [CHEMONTID:0000465] Coumaric acid esters

*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
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17548953]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[20166702]
NPO40884	Mexican propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[20307087]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	exocarp	n.a.	PMID[21114277]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21171571]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	PMID[24675423]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Bako, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Enemore, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Gedo, Ethiopia		PMID[24926420]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	Holleta, Ethiopia		PMID[24926420]
NPO33094	korean propolis	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[24928402]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	PMID[29094598]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11842	Petasites laevigatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14470	Polypodium decumanum	Species	Polypodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14169	Acrocarpia paniculata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13178	Ornithoglossum viride	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13876	Cedrela salvadorensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13473	Anodendron affine	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9569	Licaria chrysophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13379	Schizanthus tricolor	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11266	Garcinia cambogia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5280	Rubia tetragona	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7541	Ormosia hosiei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12006	Apis mellifera	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13669	Hertia cheirifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14369	Pocillopora eydouxi	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4700	Pertusaria truncata	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12521	Sphaeranthus confertifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3013	Clathria basilana	Species	Microcionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11842	Petasites laevigatus	Species	Asteraceae	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	2
Ki	12
Others	4

Activity Type	# Activity
Cell Line	1
Individual Protein	14
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	23.8	uM	PMID[493850]
NPT41	Individual Protein	Aldose reductase	Homo sapiens	IC50	=	2200.0	nM	PMID[493851]
NPT1270	Individual Protein	Aldo-keto reductase family 1 member B10	Homo sapiens	IC50	=	130.0	nM	PMID[493851]
NPT1146	Individual Protein	Carbonic anhydrase III	Homo sapiens	Ki	>	50000.0	nM	PMID[493853]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	>	50000.0	nM	PMID[493853]
NPT1062	Individual Protein	Carbonic anhydrase IV	Homo sapiens	Ki	=	18700.0	nM	PMID[493853]
NPT1143	Individual Protein	Carbonic anhydrase VA	Homo sapiens	Ki	=	970.0	nM	PMID[493853]
NPT1144	Individual Protein	Carbonic anhydrase VB	Homo sapiens	Ki	=	800.0	nM	PMID[493853]
NPT1063	Individual Protein	Carbonic anhydrase VI	Homo sapiens	Ki	=	730.0	nM	PMID[493853]
NPT1061	Individual Protein	Carbonic anhydrase XIII	Mus musculus	Ki	=	8920.0	nM	PMID[493853]
NPT2	Others	Unspecified		Ratio IC50	=	17.0	n.a.	PMID[493851]
NPT2	Others	Unspecified		Ratio IC50	>	500.0	n.a.	PMID[493852]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	>	50000.0	nM	PMID[493853]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	720.0	nM	PMID[493853]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	860.0	nM	PMID[493853]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	29400.0	nM	PMID[493853]
NPT954	Individual Protein	Carbonic anhydrase XIV	Homo sapiens	Ki	=	810.0	nM	PMID[493853]

☑ 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 NPC206341 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	238
0.1-0.2	1455
0.2-0.3	4260
0.3-0.4	11349
0.4-0.5	7251
0.5-0.6	7411
0.6-0.7	8873
0.7-0.8	1679
0.8-0.85	144
0.85-0.9	26
0.9-0.95	7
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9703	High Similarity	NPC260952
0.9612	High Similarity	NPC183700
0.9307	High Similarity	NPC304638
0.9143	High Similarity	NPC79543
0.9109	High Similarity	NPC253746
0.9091	High Similarity	NPC275519
0.901	High Similarity	NPC171843
0.8991	High Similarity	NPC296526
0.8942	High Similarity	NPC127676
0.8909	High Similarity	NPC128249
0.8839	High Similarity	NPC141791
0.8839	High Similarity	NPC263386
0.88	High Similarity	NPC32977
0.88	High Similarity	NPC81010
0.8796	High Similarity	NPC139946
0.8725	High Similarity	NPC201967
0.8704	High Similarity	NPC63345
0.8684	High Similarity	NPC470848
0.8684	High Similarity	NPC470849
0.8667	High Similarity	NPC2518
0.8654	High Similarity	NPC94343
0.8641	High Similarity	NPC130193
0.8611	High Similarity	NPC471954
0.8611	High Similarity	NPC75272
0.8609	High Similarity	NPC147654
0.8571	High Similarity	NPC179686
0.8571	High Similarity	NPC135784
0.8529	High Similarity	NPC246679
0.8529	High Similarity	NPC286006
0.8505	High Similarity	NPC135464
0.8505	High Similarity	NPC92623
0.8505	High Similarity	NPC326447
0.85	High Similarity	NPC119631
0.8496	Intermediate Similarity	NPC122117
0.8475	Intermediate Similarity	NPC289459
0.8468	Intermediate Similarity	NPC95381
0.844	Intermediate Similarity	NPC265211
0.844	Intermediate Similarity	NPC306045
0.8435	Intermediate Similarity	NPC233282
0.8426	Intermediate Similarity	NPC157473
0.8426	Intermediate Similarity	NPC151530
0.8421	Intermediate Similarity	NPC203124
0.8421	Intermediate Similarity	NPC309434
0.8421	Intermediate Similarity	NPC311091
0.8421	Intermediate Similarity	NPC471033
0.8421	Intermediate Similarity	NPC27633
0.8421	Intermediate Similarity	NPC94298
0.8411	Intermediate Similarity	NPC154899
0.8411	Intermediate Similarity	NPC227255
0.8411	Intermediate Similarity	NPC233396
0.8411	Intermediate Similarity	NPC128730
0.8407	Intermediate Similarity	NPC281277
0.8407	Intermediate Similarity	NPC19290
0.8403	Intermediate Similarity	NPC120225
0.8403	Intermediate Similarity	NPC213552
0.8396	Intermediate Similarity	NPC68269
0.8396	Intermediate Similarity	NPC470202
0.8393	Intermediate Similarity	NPC33749
0.8393	Intermediate Similarity	NPC328593
0.8393	Intermediate Similarity	NPC261453
0.8393	Intermediate Similarity	NPC217472
0.839	Intermediate Similarity	NPC246704
0.835	Intermediate Similarity	NPC257182
0.8349	Intermediate Similarity	NPC31274
0.8348	Intermediate Similarity	NPC264976
0.8333	Intermediate Similarity	NPC181709
0.8333	Intermediate Similarity	NPC113457
0.8333	Intermediate Similarity	NPC176971
0.8333	Intermediate Similarity	NPC29989
0.8333	Intermediate Similarity	NPC69332
0.8333	Intermediate Similarity	NPC95178
0.8319	Intermediate Similarity	NPC233669
0.8319	Intermediate Similarity	NPC474967
0.8318	Intermediate Similarity	NPC109637
0.8305	Intermediate Similarity	NPC212541
0.8288	Intermediate Similarity	NPC226250
0.8286	Intermediate Similarity	NPC216468
0.8286	Intermediate Similarity	NPC78119
0.8286	Intermediate Similarity	NPC51333
0.8286	Intermediate Similarity	NPC132078
0.8269	Intermediate Similarity	NPC283711
0.8264	Intermediate Similarity	NPC2596
0.8252	Intermediate Similarity	NPC151715
0.8246	Intermediate Similarity	NPC131192
0.8241	Intermediate Similarity	NPC303141
0.8241	Intermediate Similarity	NPC243677
0.8241	Intermediate Similarity	NPC288760
0.8235	Intermediate Similarity	NPC265413
0.8235	Intermediate Similarity	NPC10154
0.8235	Intermediate Similarity	NPC288945
0.8235	Intermediate Similarity	NPC45040
0.8235	Intermediate Similarity	NPC474532
0.823	Intermediate Similarity	NPC41851
0.8214	Intermediate Similarity	NPC42911
0.8214	Intermediate Similarity	NPC153795
0.8214	Intermediate Similarity	NPC199462
0.8214	Intermediate Similarity	NPC228988
0.8214	Intermediate Similarity	NPC290353
0.8214	Intermediate Similarity	NPC131530
0.8214	Intermediate Similarity	NPC17693
0.8208	Intermediate Similarity	NPC213730
0.8205	Intermediate Similarity	NPC131868
0.8197	Intermediate Similarity	NPC214246
0.8197	Intermediate Similarity	NPC83062
0.819	Intermediate Similarity	NPC140619
0.8182	Intermediate Similarity	NPC288416
0.8174	Intermediate Similarity	NPC175799
0.8174	Intermediate Similarity	NPC65791
0.8174	Intermediate Similarity	NPC145023
0.8174	Intermediate Similarity	NPC610
0.8174	Intermediate Similarity	NPC200988
0.8173	Intermediate Similarity	NPC26244
0.8167	Intermediate Similarity	NPC137416
0.8165	Intermediate Similarity	NPC70843
0.8158	Intermediate Similarity	NPC51345
0.8158	Intermediate Similarity	NPC23402
0.8151	Intermediate Similarity	NPC14141
0.8148	Intermediate Similarity	NPC474603
0.8148	Intermediate Similarity	NPC12987
0.8142	Intermediate Similarity	NPC123175
0.8142	Intermediate Similarity	NPC176730
0.8137	Intermediate Similarity	NPC300017
0.8136	Intermediate Similarity	NPC7830
0.8136	Intermediate Similarity	NPC251259
0.8131	Intermediate Similarity	NPC91461
0.8131	Intermediate Similarity	NPC7686
0.8131	Intermediate Similarity	NPC40258
0.8125	Intermediate Similarity	NPC266932
0.812	Intermediate Similarity	NPC202474
0.8119	Intermediate Similarity	NPC104216
0.8115	Intermediate Similarity	NPC110313
0.8115	Intermediate Similarity	NPC219923
0.8113	Intermediate Similarity	NPC245561
0.8108	Intermediate Similarity	NPC88141
0.8103	Intermediate Similarity	NPC86198
0.8103	Intermediate Similarity	NPC277460
0.8103	Intermediate Similarity	NPC94637
0.8099	Intermediate Similarity	NPC118584
0.8095	Intermediate Similarity	NPC473388
0.8083	Intermediate Similarity	NPC60517
0.8083	Intermediate Similarity	NPC20443
0.8083	Intermediate Similarity	NPC146886
0.8077	Intermediate Similarity	NPC128062
0.8073	Intermediate Similarity	NPC238115
0.8073	Intermediate Similarity	NPC473855
0.807	Intermediate Similarity	NPC235250
0.807	Intermediate Similarity	NPC81808
0.807	Intermediate Similarity	NPC285350
0.8067	Intermediate Similarity	NPC52097
0.8067	Intermediate Similarity	NPC296202
0.8065	Intermediate Similarity	NPC225384
0.8065	Intermediate Similarity	NPC138777
0.8065	Intermediate Similarity	NPC246869
0.8065	Intermediate Similarity	NPC318799
0.8051	Intermediate Similarity	NPC476872
0.8051	Intermediate Similarity	NPC204466
0.8039	Intermediate Similarity	NPC240108
0.8039	Intermediate Similarity	NPC213156
0.8037	Intermediate Similarity	NPC52472
0.8037	Intermediate Similarity	NPC13755
0.8036	Intermediate Similarity	NPC141068
0.8036	Intermediate Similarity	NPC473809
0.8034	Intermediate Similarity	NPC90522
0.8034	Intermediate Similarity	NPC328459
0.8034	Intermediate Similarity	NPC70084
0.8034	Intermediate Similarity	NPC470214
0.8034	Intermediate Similarity	NPC470215
0.8034	Intermediate Similarity	NPC109371
0.8033	Intermediate Similarity	NPC159987
0.8033	Intermediate Similarity	NPC78061
0.8033	Intermediate Similarity	NPC122359
0.8019	Intermediate Similarity	NPC175298
0.8018	Intermediate Similarity	NPC470039
0.8018	Intermediate Similarity	NPC201959
0.8018	Intermediate Similarity	NPC75440
0.8018	Intermediate Similarity	NPC169450
0.8017	Intermediate Similarity	NPC67951
0.8017	Intermediate Similarity	NPC4164
0.8017	Intermediate Similarity	NPC263754
0.8017	Intermediate Similarity	NPC87113
0.8017	Intermediate Similarity	NPC278652
0.8017	Intermediate Similarity	NPC49938
0.8017	Intermediate Similarity	NPC83218
0.8017	Intermediate Similarity	NPC126991
0.8017	Intermediate Similarity	NPC183154
0.8	Intermediate Similarity	NPC294902
0.8	Intermediate Similarity	NPC1786
0.8	Intermediate Similarity	NPC285345
0.8	Intermediate Similarity	NPC274678
0.8	Intermediate Similarity	NPC1075
0.7983	Intermediate Similarity	NPC70752
0.7983	Intermediate Similarity	NPC11724
0.7982	Intermediate Similarity	NPC261573
0.7982	Intermediate Similarity	NPC283546
0.7982	Intermediate Similarity	NPC8931
0.7982	Intermediate Similarity	NPC93831
0.7982	Intermediate Similarity	NPC120693
0.7981	Intermediate Similarity	NPC138117
0.7981	Intermediate Similarity	NPC325292
0.7967	Intermediate Similarity	NPC478215

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 NPC206341 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	210
0.1-0.2	947
0.2-0.3	1302
0.3-0.4	2684
0.4-0.5	2024
0.5-0.6	1220
0.6-0.7	660
0.7-0.8	94
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8505	High Similarity	NPD3134	Approved
0.8421	Intermediate Similarity	NPD9545	Approved
0.8257	Intermediate Similarity	NPD1358	Approved
0.8252	Intermediate Similarity	NPD2934	Approved
0.8252	Intermediate Similarity	NPD2933	Approved
0.8173	Intermediate Similarity	NPD2859	Approved
0.8173	Intermediate Similarity	NPD2860	Approved
0.8165	Intermediate Similarity	NPD968	Approved
0.8103	Intermediate Similarity	NPD1894	Discontinued
0.7944	Intermediate Similarity	NPD3020	Approved
0.7931	Intermediate Similarity	NPD9493	Approved
0.7909	Intermediate Similarity	NPD9697	Approved
0.7895	Intermediate Similarity	NPD5535	Approved
0.784	Intermediate Similarity	NPD3764	Approved
0.7833	Intermediate Similarity	NPD422	Phase 1
0.7833	Intermediate Similarity	NPD1535	Discovery
0.7778	Intermediate Similarity	NPD1238	Approved
0.7769	Intermediate Similarity	NPD1481	Phase 2
0.7768	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.775	Intermediate Similarity	NPD3847	Discontinued
0.7724	Intermediate Similarity	NPD1203	Approved
0.7723	Intermediate Similarity	NPD111	Approved
0.7705	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD1241	Discontinued
0.7667	Intermediate Similarity	NPD4626	Approved
0.7647	Intermediate Similarity	NPD1548	Phase 1
0.7642	Intermediate Similarity	NPD3225	Approved
0.7603	Intermediate Similarity	NPD3496	Discontinued
0.7583	Intermediate Similarity	NPD5691	Approved
0.7581	Intermediate Similarity	NPD2797	Approved
0.7578	Intermediate Similarity	NPD4060	Phase 1
0.7545	Intermediate Similarity	NPD1242	Phase 1
0.7544	Intermediate Similarity	NPD2684	Approved
0.7519	Intermediate Similarity	NPD4340	Discontinued
0.75	Intermediate Similarity	NPD7266	Discontinued
0.748	Intermediate Similarity	NPD5163	Phase 2
0.7438	Intermediate Similarity	NPD5585	Approved
0.7424	Intermediate Similarity	NPD2935	Discontinued
0.7422	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7422	Intermediate Similarity	NPD6798	Discontinued
0.7419	Intermediate Similarity	NPD6583	Phase 3
0.7419	Intermediate Similarity	NPD6582	Phase 2
0.7417	Intermediate Similarity	NPD5536	Phase 2
0.7407	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD1610	Phase 2
0.7391	Intermediate Similarity	NPD9266	Approved
0.7391	Intermediate Similarity	NPD74	Approved
0.7388	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD6233	Phase 2
0.7364	Intermediate Similarity	NPD4062	Phase 3
0.736	Intermediate Similarity	NPD1283	Approved
0.735	Intermediate Similarity	NPD228	Approved
0.7339	Intermediate Similarity	NPD9717	Approved
0.7333	Intermediate Similarity	NPD4628	Phase 3
0.7328	Intermediate Similarity	NPD5451	Approved
0.7328	Intermediate Similarity	NPD3022	Approved
0.7328	Intermediate Similarity	NPD3021	Approved
0.7323	Intermediate Similarity	NPD5736	Approved
0.7304	Intermediate Similarity	NPD9264	Approved
0.7304	Intermediate Similarity	NPD9267	Approved
0.7304	Intermediate Similarity	NPD9263	Approved
0.7304	Intermediate Similarity	NPD290	Approved
0.7302	Intermediate Similarity	NPD1164	Approved
0.7293	Intermediate Similarity	NPD1551	Phase 2
0.7288	Intermediate Similarity	NPD7843	Approved
0.7288	Intermediate Similarity	NPD821	Approved
0.7287	Intermediate Similarity	NPD3268	Approved
0.7279	Intermediate Similarity	NPD6190	Approved
0.7266	Intermediate Similarity	NPD6832	Phase 2
0.7252	Intermediate Similarity	NPD6355	Discontinued
0.7252	Intermediate Similarity	NPD230	Phase 1
0.7244	Intermediate Similarity	NPD6584	Phase 3
0.7238	Intermediate Similarity	NPD1282	Approved
0.7236	Intermediate Similarity	NPD1778	Approved
0.7236	Intermediate Similarity	NPD6516	Phase 2
0.7236	Intermediate Similarity	NPD5846	Approved
0.7232	Intermediate Similarity	NPD3028	Approved
0.7226	Intermediate Similarity	NPD7440	Discontinued
0.7218	Intermediate Similarity	NPD2799	Discontinued
0.7209	Intermediate Similarity	NPD7095	Approved
0.7206	Intermediate Similarity	NPD3750	Approved
0.7206	Intermediate Similarity	NPD8166	Discontinued
0.7203	Intermediate Similarity	NPD969	Suspended
0.72	Intermediate Similarity	NPD3972	Approved
0.72	Intermediate Similarity	NPD1608	Approved
0.7193	Intermediate Similarity	NPD5909	Discontinued
0.7188	Intermediate Similarity	NPD2861	Phase 2
0.7176	Intermediate Similarity	NPD4140	Approved
0.7176	Intermediate Similarity	NPD1240	Approved
0.7168	Intermediate Similarity	NPD940	Approved
0.7168	Intermediate Similarity	NPD846	Approved
0.7154	Intermediate Similarity	NPD2313	Discontinued
0.7143	Intermediate Similarity	NPD4978	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4359	Approved
0.7143	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD2614	Approved
0.7132	Intermediate Similarity	NPD4908	Phase 1
0.712	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.712	Intermediate Similarity	NPD1281	Approved
0.7107	Intermediate Similarity	NPD4198	Discontinued
0.7107	Intermediate Similarity	NPD255	Approved
0.7107	Intermediate Similarity	NPD7157	Approved
0.7107	Intermediate Similarity	NPD256	Approved
0.7107	Intermediate Similarity	NPD6671	Approved
0.7103	Intermediate Similarity	NPD689	Discontinued
0.7099	Intermediate Similarity	NPD6663	Approved
0.709	Intermediate Similarity	NPD1510	Phase 2
0.709	Intermediate Similarity	NPD4308	Phase 3
0.7087	Intermediate Similarity	NPD1876	Approved
0.7083	Intermediate Similarity	NPD5283	Phase 1
0.708	Intermediate Similarity	NPD7003	Approved
0.7073	Intermediate Similarity	NPD1182	Approved
0.7068	Intermediate Similarity	NPD1607	Approved
0.7059	Intermediate Similarity	NPD1549	Phase 2
0.7054	Intermediate Similarity	NPD454	Approved
0.7054	Intermediate Similarity	NPD9494	Approved
0.7049	Intermediate Similarity	NPD9568	Approved
0.7049	Intermediate Similarity	NPD3596	Phase 2
0.7043	Intermediate Similarity	NPD1237	Approved
0.7042	Intermediate Similarity	NPD3455	Phase 2
0.7037	Intermediate Similarity	NPD9258	Approved
0.7037	Intermediate Similarity	NPD4477	Approved
0.7037	Intermediate Similarity	NPD9256	Approved
0.7037	Intermediate Similarity	NPD4476	Approved
0.7034	Intermediate Similarity	NPD9380	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD3266	Approved
0.7031	Intermediate Similarity	NPD3267	Approved
0.7027	Intermediate Similarity	NPD1809	Phase 2
0.7027	Intermediate Similarity	NPD844	Approved
0.7023	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD3374	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD7097	Phase 1
0.7007	Intermediate Similarity	NPD2976	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1202	Approved
0.7	Intermediate Similarity	NPD845	Approved
0.6992	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD5124	Phase 1
0.6985	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD2344	Approved
0.6985	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD2798	Approved
0.6975	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.697	Remote Similarity	NPD520	Approved
0.6964	Remote Similarity	NPD288	Approved
0.6963	Remote Similarity	NPD7033	Discontinued
0.696	Remote Similarity	NPD17	Approved
0.696	Remote Similarity	NPD2667	Approved
0.696	Remote Similarity	NPD2668	Approved
0.696	Remote Similarity	NPD5238	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9261	Approved
0.6957	Remote Similarity	NPD6647	Phase 2
0.6953	Remote Similarity	NPD196	Phase 1
0.695	Remote Similarity	NPD6273	Approved
0.6949	Remote Similarity	NPD2182	Approved
0.6947	Remote Similarity	NPD3027	Phase 3
0.6944	Remote Similarity	NPD9295	Approved
0.6942	Remote Similarity	NPD2234	Approved
0.6942	Remote Similarity	NPD2228	Approved
0.6942	Remote Similarity	NPD2229	Approved
0.6935	Remote Similarity	NPD6580	Approved
0.6935	Remote Similarity	NPD6581	Approved
0.6935	Remote Similarity	NPD3091	Approved
0.6934	Remote Similarity	NPD7596	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD5958	Discontinued
0.6934	Remote Similarity	NPD4534	Discontinued
0.6931	Remote Similarity	NPD9294	Approved
0.693	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2231	Phase 2
0.6929	Remote Similarity	NPD2235	Phase 2
0.6929	Remote Similarity	NPD6799	Approved
0.6917	Remote Similarity	NPD2979	Phase 3
0.6912	Remote Similarity	NPD1537	Approved
0.6912	Remote Similarity	NPD1519	Approved
0.6912	Remote Similarity	NPD1538	Phase 1
0.6911	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD2354	Approved
0.6903	Remote Similarity	NPD5926	Approved
0.6903	Remote Similarity	NPD9495	Approved
0.69	Remote Similarity	NPD9716	Approved
0.6899	Remote Similarity	NPD987	Approved
0.6897	Remote Similarity	NPD9608	Approved
0.6897	Remote Similarity	NPD9610	Approved
0.6885	Remote Similarity	NPD9281	Approved
0.6885	Remote Similarity	NPD690	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1357	Approved
0.688	Remote Similarity	NPD6830	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1651	Approved
0.6879	Remote Similarity	NPD3536	Discontinued
0.6875	Remote Similarity	NPD3685	Discontinued
0.6866	Remote Similarity	NPD1933	Approved
0.6864	Remote Similarity	NPD2342	Discontinued
0.6861	Remote Similarity	NPD5865	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6667	Approved
0.6857	Remote Similarity	NPD6666	Approved
0.685	Remote Similarity	NPD1091	Approved
0.685	Remote Similarity	NPD1611	Approved
0.6846	Remote Similarity	NPD1019	Discontinued

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