NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	250.12
Volume:	264.122
LogP:	3.587
LogD:	3.138
LogS:	-3.125
# Rotatable Bonds:	7
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.352
Synthetic Accessibility Score:	2.065
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.75
MDCK Permeability:	2.7873064027517103e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.038
Human Intestinal Absorption (HIA):	0.01
20% Bioavailability (F20%):	0.953
30% Bioavailability (F30%):	0.943

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	96.19435119628906%
Volume Distribution (VD):	0.511
Pgp-substrate:	4.766114711761475%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.275
CYP2C19-inhibitor:	0.803
CYP2C19-substrate:	0.088
CYP2C9-inhibitor:	0.759
CYP2C9-substrate:	0.907
CYP2D6-inhibitor:	0.768
CYP2D6-substrate:	0.707
CYP3A4-inhibitor:	0.443
CYP3A4-substrate:	0.212

ADMET: Excretion

Clearance (CL):	14.653
Half-life (T1/2):	0.905

ADMET: Toxicity

hERG Blockers:	0.086
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.034
AMES Toxicity:	0.292
Rat Oral Acute Toxicity:	0.406
Maximum Recommended Daily Dose:	0.13
Skin Sensitization:	0.955
Carcinogencity:	0.39
Eye Corrosion:	0.071
Eye Irritation:	0.923
Respiratory Toxicity:	0.226

Download Data

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

Natural Product: NPC328593

Natural Product ID:	NPC328593
*Common Name:**	Pentyl 3-(3,4-Dihydroxyphenyl)Acrylate
IUPAC Name:	pentyl (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
Synonyms:	Pentyl 3-(3,4-Dihydroxyphenyl)Acrylate
Standard InCHIKey:	ULPIXLKKVGJPCT-SOFGYWHQSA-N
Standard InCHI:	InChI=1S/C14H18O4/c1-2-3-4-9-18-14(17)8-6-11-5-7-12(15)13(16)10-11/h5-8,10,15-16H,2-4,9H2,1H3/b8-6+
SMILES:	CCCCCOC(=O)/C=C/c1ccc(c(c1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2088769
PubChem CID:	15086370
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000476] Cinnamic acids and derivatives [CHEMONTID:0001391] Hydroxycinnamic acids and derivatives [CHEMONTID:0000059] Coumaric acids 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
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24345512]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	root	n.a.	n.a.	PMID[24959987]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	Rhizomes	Nanning, Guangxi Province, China	2012-Dec	PMID[26132528]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	Roots; Rhizomes	n.a.	n.a.	PMID[30698432]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7715	Sophora tonkinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7715	Sophora tonkinensis	Species	Fabaceae	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
EC50	1
IC50	14
Others	4

Activity Type	# Activity
Cell Line	10
Individual Protein	1
NON-MOLECULAR	4
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	=	1910.0	nM	PMID[488077]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	2020.0	nM	PMID[488077]
NPT1668	Cell Line	NCI-H157	Homo sapiens	IC50	=	2280.0	nM	PMID[488077]
NPT390	Cell Line	LOX IMVI	Homo sapiens	IC50	=	3380.0	nM	PMID[488077]
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	=	4690.0	nM	PMID[488077]
NPT379	Cell Line	HOP-62	Homo sapiens	IC50	=	5110.0	nM	PMID[488077]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	5750.0	nM	PMID[488077]
NPT1669	Cell Line	NCI-H1792	Homo sapiens	IC50	=	6350.0	nM	PMID[488077]
NPT387	Cell Line	M14	Homo sapiens	IC50	=	7480.0	nM	PMID[488077]
NPT1307	Cell Line	Calu-1	Homo sapiens	IC50	=	8570.0	nM	PMID[488077]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2960.0	nM	PMID[488077]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6800.0	nM	PMID[488077]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7240.0	nM	PMID[488077]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7730.0	nM	PMID[488077]
NPT78	Individual Protein	Beta amyloid A4 protein	Homo sapiens	EC50	=	2580.0	nM	PMID[488078]
NPT2	Others	Unspecified		Inhibition	=	11.0	%	PMID[488078]
NPT2	Others	Unspecified		Inhibition	>	90.0	%	PMID[488078]
NPT35	Others	n.a.		Inhibition	=	46.0	%	PMID[488078]
NPT35	Others	n.a.		Inhibition	=	62.0	%	PMID[488078]

☑ 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 NPC328593 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	220
0.1-0.2	1265
0.2-0.3	4363
0.3-0.4	10909
0.4-0.5	7756
0.5-0.6	7170
0.6-0.7	8602
0.7-0.8	2121
0.8-0.85	190
0.85-0.9	63
0.9-0.95	25
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC33749
1.0	High Similarity	NPC261453
0.9907	High Similarity	NPC474967
0.9907	High Similarity	NPC233669
0.9906	High Similarity	NPC95381
0.9815	High Similarity	NPC281277
0.9717	High Similarity	NPC226250
0.9636	High Similarity	NPC203124
0.9636	High Similarity	NPC309434
0.963	High Similarity	NPC217472
0.9545	High Similarity	NPC65791
0.9381	High Similarity	NPC470848
0.9381	High Similarity	NPC204466
0.9381	High Similarity	NPC470849
0.9375	High Similarity	NPC263386
0.9375	High Similarity	NPC141791
0.9298	High Similarity	NPC70752
0.9292	High Similarity	NPC202474
0.9286	High Similarity	NPC275519
0.9266	High Similarity	NPC131530
0.9245	High Similarity	NPC1786
0.9245	High Similarity	NPC1075
0.9245	High Similarity	NPC294902
0.913	High Similarity	NPC147654
0.9115	High Similarity	NPC272471
0.9115	High Similarity	NPC107588
0.9115	High Similarity	NPC137537
0.9115	High Similarity	NPC70744
0.9115	High Similarity	NPC164706
0.906	High Similarity	NPC246704
0.906	High Similarity	NPC20443
0.906	High Similarity	NPC60517
0.906	High Similarity	NPC146886
0.9035	High Similarity	NPC241634
0.9009	High Similarity	NPC264558
0.8983	High Similarity	NPC289459
0.8974	High Similarity	NPC474275
0.8974	High Similarity	NPC224208
0.8962	High Similarity	NPC304638
0.8957	High Similarity	NPC2058
0.8908	High Similarity	NPC213552
0.8908	High Similarity	NPC120225
0.8908	High Similarity	NPC118584
0.8889	High Similarity	NPC19149
0.8879	High Similarity	NPC79672
0.8879	High Similarity	NPC52087
0.887	High Similarity	NPC37858
0.8868	High Similarity	NPC94343
0.886	High Similarity	NPC175799
0.886	High Similarity	NPC610
0.886	High Similarity	NPC200988
0.886	High Similarity	NPC145023
0.8824	High Similarity	NPC67951
0.8783	High Similarity	NPC86198
0.8774	High Similarity	NPC253746
0.8761	High Similarity	NPC294941
0.876	High Similarity	NPC110313
0.876	High Similarity	NPC109275
0.875	High Similarity	NPC147192
0.875	High Similarity	NPC475695
0.8707	High Similarity	NPC470214
0.8707	High Similarity	NPC70084
0.8707	High Similarity	NPC109371
0.8707	High Similarity	NPC470215
0.8696	High Similarity	NPC39793
0.8689	High Similarity	NPC83062
0.8689	High Similarity	NPC48315
0.8689	High Similarity	NPC30174
0.8679	High Similarity	NPC171843
0.8678	High Similarity	NPC476873
0.8673	High Similarity	NPC148969
0.8667	High Similarity	NPC197832
0.8667	High Similarity	NPC132921
0.8655	High Similarity	NPC285345
0.8655	High Similarity	NPC306100
0.8636	High Similarity	NPC260952
0.8624	High Similarity	NPC127676
0.8621	High Similarity	NPC124916
0.8607	High Similarity	NPC232880
0.8595	High Similarity	NPC251407
0.8595	High Similarity	NPC168653
0.8583	High Similarity	NPC288945
0.8583	High Similarity	NPC469568
0.8571	High Similarity	NPC183700
0.8559	High Similarity	NPC224814
0.8559	High Similarity	NPC60962
0.8559	High Similarity	NPC189844
0.8559	High Similarity	NPC14007
0.8559	High Similarity	NPC269843
0.8559	High Similarity	NPC109083
0.8537	High Similarity	NPC477294
0.8537	High Similarity	NPC226855
0.8537	High Similarity	NPC477293
0.8537	High Similarity	NPC229784
0.8512	High Similarity	NPC280767
0.8512	High Similarity	NPC300326
0.8512	High Similarity	NPC58279
0.8505	High Similarity	NPC131587
0.85	High Similarity	NPC212541
0.8496	Intermediate Similarity	NPC297657
0.8496	Intermediate Similarity	NPC139946
0.848	Intermediate Similarity	NPC473285
0.8468	Intermediate Similarity	NPC237506
0.8468	Intermediate Similarity	NPC217052
0.8468	Intermediate Similarity	NPC329344
0.8468	Intermediate Similarity	NPC32626
0.8462	Intermediate Similarity	NPC277460
0.8455	Intermediate Similarity	NPC478215
0.8435	Intermediate Similarity	NPC41851
0.8421	Intermediate Similarity	NPC51698
0.8417	Intermediate Similarity	NPC286573
0.8413	Intermediate Similarity	NPC475468
0.8413	Intermediate Similarity	NPC168799
0.8413	Intermediate Similarity	NPC155209
0.8413	Intermediate Similarity	NPC254398
0.8407	Intermediate Similarity	NPC222084
0.8403	Intermediate Similarity	NPC158949
0.84	Intermediate Similarity	NPC219677
0.84	Intermediate Similarity	NPC198388
0.8396	Intermediate Similarity	NPC257182
0.8396	Intermediate Similarity	NPC107522
0.8393	Intermediate Similarity	NPC206341
0.8387	Intermediate Similarity	NPC477300
0.8376	Intermediate Similarity	NPC278652
0.8374	Intermediate Similarity	NPC158654
0.8361	Intermediate Similarity	NPC27352
0.8349	Intermediate Similarity	NPC110764
0.8347	Intermediate Similarity	NPC106659
0.8347	Intermediate Similarity	NPC160900
0.8347	Intermediate Similarity	NPC229084
0.8347	Intermediate Similarity	NPC18984
0.8346	Intermediate Similarity	NPC471110
0.8346	Intermediate Similarity	NPC135127
0.8346	Intermediate Similarity	NPC106406
0.8346	Intermediate Similarity	NPC471883
0.8333	Intermediate Similarity	NPC139617
0.8333	Intermediate Similarity	NPC78918
0.8333	Intermediate Similarity	NPC473924
0.8333	Intermediate Similarity	NPC177291
0.8333	Intermediate Similarity	NPC18074
0.8333	Intermediate Similarity	NPC25581
0.8333	Intermediate Similarity	NPC5419
0.8333	Intermediate Similarity	NPC194416
0.8333	Intermediate Similarity	NPC472271
0.8333	Intermediate Similarity	NPC61
0.832	Intermediate Similarity	NPC285361
0.8319	Intermediate Similarity	NPC75272
0.8319	Intermediate Similarity	NPC246358
0.8319	Intermediate Similarity	NPC471954
0.8319	Intermediate Similarity	NPC36108
0.8319	Intermediate Similarity	NPC233731
0.8319	Intermediate Similarity	NPC7097
0.8306	Intermediate Similarity	NPC46192
0.8305	Intermediate Similarity	NPC212743
0.8302	Intermediate Similarity	NPC32977
0.8302	Intermediate Similarity	NPC81010
0.8288	Intermediate Similarity	NPC288760
0.8273	Intermediate Similarity	NPC477801
0.8273	Intermediate Similarity	NPC477802
0.8273	Intermediate Similarity	NPC196479
0.8264	Intermediate Similarity	NPC327070
0.8264	Intermediate Similarity	NPC114298
0.8257	Intermediate Similarity	NPC223393
0.8254	Intermediate Similarity	NPC318799
0.8241	Intermediate Similarity	NPC109955
0.824	Intermediate Similarity	NPC208536
0.824	Intermediate Similarity	NPC64111
0.8235	Intermediate Similarity	NPC477803
0.8235	Intermediate Similarity	NPC57501
0.822	Intermediate Similarity	NPC122117
0.822	Intermediate Similarity	NPC280001
0.8217	Intermediate Similarity	NPC476699
0.8217	Intermediate Similarity	NPC157554
0.8217	Intermediate Similarity	NPC90431
0.8217	Intermediate Similarity	NPC120852
0.8217	Intermediate Similarity	NPC471872
0.8217	Intermediate Similarity	NPC154485
0.8211	Intermediate Similarity	NPC87113
0.8211	Intermediate Similarity	NPC271985
0.8203	Intermediate Similarity	NPC886
0.8203	Intermediate Similarity	NPC474895
0.8203	Intermediate Similarity	NPC111635
0.8203	Intermediate Similarity	NPC34293
0.8203	Intermediate Similarity	NPC287597
0.8198	Intermediate Similarity	NPC12278
0.8198	Intermediate Similarity	NPC2518
0.8197	Intermediate Similarity	NPC257976
0.8197	Intermediate Similarity	NPC238810
0.8197	Intermediate Similarity	NPC242372
0.8197	Intermediate Similarity	NPC4181
0.8197	Intermediate Similarity	NPC164778
0.8182	Intermediate Similarity	NPC322332
0.8182	Intermediate Similarity	NPC310373
0.8182	Intermediate Similarity	NPC114845
0.8174	Intermediate Similarity	NPC8547
0.8174	Intermediate Similarity	NPC173746
0.8174	Intermediate Similarity	NPC156840
0.8174	Intermediate Similarity	NPC257124
0.816	Intermediate Similarity	NPC167463
0.8154	Intermediate Similarity	NPC471152

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 NPC328593 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	192
0.1-0.2	840
0.2-0.3	1701
0.3-0.4	2811
0.4-0.5	1835
0.5-0.6	1195
0.6-0.7	511
0.7-0.8	60
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8347	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD1358	Approved
0.8174	Intermediate Similarity	NPD228	Approved
0.8125	Intermediate Similarity	NPD230	Phase 1
0.8092	Intermediate Similarity	NPD7266	Discontinued
0.8053	Intermediate Similarity	NPD3134	Approved
0.8	Intermediate Similarity	NPD3021	Approved
0.8	Intermediate Similarity	NPD3022	Approved
0.7937	Intermediate Similarity	NPD9494	Approved
0.791	Intermediate Similarity	NPD8166	Discontinued
0.7851	Intermediate Similarity	NPD9545	Approved
0.7769	Intermediate Similarity	NPD826	Approved
0.7769	Intermediate Similarity	NPD5536	Phase 2
0.7769	Intermediate Similarity	NPD825	Approved
0.7721	Intermediate Similarity	NPD6190	Approved
0.7661	Intermediate Similarity	NPD3496	Discontinued
0.7642	Intermediate Similarity	NPD1357	Approved
0.7581	Intermediate Similarity	NPD4626	Approved
0.7576	Intermediate Similarity	NPD555	Phase 2
0.754	Intermediate Similarity	NPD9269	Phase 2
0.75	Intermediate Similarity	NPD4060	Phase 1
0.75	Intermediate Similarity	NPD5691	Approved
0.7465	Intermediate Similarity	NPD3455	Phase 2
0.7453	Intermediate Similarity	NPD111	Approved
0.7442	Intermediate Similarity	NPD258	Approved
0.7442	Intermediate Similarity	NPD257	Approved
0.7424	Intermediate Similarity	NPD259	Phase 1
0.7405	Intermediate Similarity	NPD3027	Phase 3
0.7398	Intermediate Similarity	NPD9493	Approved
0.7394	Intermediate Similarity	NPD1653	Approved
0.7355	Intermediate Similarity	NPD9377	Approved
0.7355	Intermediate Similarity	NPD9379	Approved
0.7333	Intermediate Similarity	NPD9280	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2934	Approved
0.7321	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2933	Approved
0.7313	Intermediate Similarity	NPD447	Suspended
0.7311	Intermediate Similarity	NPD2684	Approved
0.7302	Intermediate Similarity	NPD1778	Approved
0.7295	Intermediate Similarity	NPD5283	Phase 1
0.7257	Intermediate Similarity	NPD844	Approved
0.7257	Intermediate Similarity	NPD2859	Approved
0.7257	Intermediate Similarity	NPD2860	Approved
0.7252	Intermediate Similarity	NPD9569	Approved
0.7227	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD9268	Approved
0.7217	Intermediate Similarity	NPD3020	Approved
0.7213	Intermediate Similarity	NPD7843	Approved
0.7188	Intermediate Similarity	NPD422	Phase 1
0.7177	Intermediate Similarity	NPD7157	Approved
0.7168	Intermediate Similarity	NPD9296	Approved
0.7165	Intermediate Similarity	NPD9381	Approved
0.7165	Intermediate Similarity	NPD9384	Approved
0.7155	Intermediate Similarity	NPD1242	Phase 1
0.7143	Intermediate Similarity	NPD7095	Approved
0.7121	Intermediate Similarity	NPD5736	Approved
0.7113	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD1613	Approved
0.7101	Intermediate Similarity	NPD2935	Discontinued
0.709	Intermediate Similarity	NPD3145	Approved
0.709	Intermediate Similarity	NPD3144	Approved
0.7083	Intermediate Similarity	NPD290	Approved
0.7077	Intermediate Similarity	NPD9622	Approved
0.7073	Intermediate Similarity	NPD5535	Approved
0.7068	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD9697	Approved
0.7059	Intermediate Similarity	NPD275	Approved
0.7059	Intermediate Similarity	NPD274	Approved
0.7054	Intermediate Similarity	NPD3705	Approved
0.7043	Intermediate Similarity	NPD288	Approved
0.7037	Intermediate Similarity	NPD2674	Phase 3
0.7021	Intermediate Similarity	NPD4110	Phase 3
0.7021	Intermediate Similarity	NPD4628	Phase 3
0.7021	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD1241	Discontinued
0.7015	Intermediate Similarity	NPD9536	Phase 1
0.7015	Intermediate Similarity	NPD9537	Phase 1
0.7009	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6653	Approved
0.7	Intermediate Similarity	NPD9717	Approved
0.7	Intermediate Similarity	NPD968	Approved
0.6992	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD969	Suspended
0.6985	Remote Similarity	NPD3620	Phase 2
0.6985	Remote Similarity	NPD943	Approved
0.6985	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6984	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD9570	Approved
0.6977	Remote Similarity	NPD3847	Discontinued
0.6963	Remote Similarity	NPD3764	Approved
0.6963	Remote Similarity	NPD6798	Discontinued
0.6953	Remote Similarity	NPD5585	Approved
0.6949	Remote Similarity	NPD291	Approved
0.6949	Remote Similarity	NPD846	Approved
0.6949	Remote Similarity	NPD940	Approved
0.6935	Remote Similarity	NPD821	Approved
0.6934	Remote Similarity	NPD4340	Discontinued
0.6934	Remote Similarity	NPD6355	Discontinued
0.6933	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD1535	Discovery
0.6917	Remote Similarity	NPD9621	Approved
0.6917	Remote Similarity	NPD9620	Approved
0.6917	Remote Similarity	NPD9619	Approved
0.6912	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD6663	Approved
0.6912	Remote Similarity	NPD4062	Phase 3
0.6912	Remote Similarity	NPD6233	Phase 2
0.6905	Remote Similarity	NPD6671	Approved
0.6905	Remote Similarity	NPD4198	Discontinued
0.6894	Remote Similarity	NPD9634	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD1283	Approved
0.6885	Remote Similarity	NPD74	Approved
0.6885	Remote Similarity	NPD9266	Approved
0.6875	Remote Similarity	NPD1894	Discontinued
0.6871	Remote Similarity	NPD3111	Phase 1
0.687	Remote Similarity	NPD1481	Phase 2
0.6861	Remote Similarity	NPD1558	Phase 1
0.6861	Remote Similarity	NPD4140	Approved
0.6847	Remote Similarity	NPD1282	Approved
0.6842	Remote Similarity	NPD3055	Approved
0.6842	Remote Similarity	NPD3053	Approved
0.6842	Remote Similarity	NPD1203	Approved
0.6842	Remote Similarity	NPD987	Approved
0.6838	Remote Similarity	NPD601	Approved
0.6838	Remote Similarity	NPD411	Approved
0.6838	Remote Similarity	NPD597	Approved
0.6838	Remote Similarity	NPD598	Approved
0.6825	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3882	Suspended
0.6818	Remote Similarity	NPD2982	Phase 2
0.6818	Remote Similarity	NPD2983	Phase 2
0.6818	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1809	Phase 2
0.6809	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD9264	Approved
0.6803	Remote Similarity	NPD9263	Approved
0.6803	Remote Similarity	NPD9267	Approved
0.6803	Remote Similarity	NPD3686	Approved
0.6803	Remote Similarity	NPD3687	Approved
0.68	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD3092	Approved
0.6791	Remote Similarity	NPD5647	Approved
0.6791	Remote Similarity	NPD6584	Phase 3
0.6788	Remote Similarity	NPD1136	Approved
0.6788	Remote Similarity	NPD1132	Approved
0.6788	Remote Similarity	NPD1130	Approved
0.6786	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD845	Approved
0.6772	Remote Similarity	NPD256	Approved
0.6772	Remote Similarity	NPD255	Approved
0.6767	Remote Similarity	NPD5311	Approved
0.6767	Remote Similarity	NPD5310	Approved
0.6763	Remote Similarity	NPD2653	Approved
0.6761	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD1511	Approved
0.6759	Remote Similarity	NPD4357	Discontinued
0.6757	Remote Similarity	NPD824	Approved
0.675	Remote Similarity	NPD6647	Phase 2
0.6744	Remote Similarity	NPD3091	Approved
0.6742	Remote Similarity	NPD2981	Phase 2
0.6742	Remote Similarity	NPD1608	Approved
0.6742	Remote Similarity	NPD2337	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD3059	Approved
0.6739	Remote Similarity	NPD3062	Approved
0.6739	Remote Similarity	NPD3061	Approved
0.6733	Remote Similarity	NPD1934	Approved
0.6726	Remote Similarity	NPD689	Discontinued
0.6721	Remote Similarity	NPD1444	Approved
0.6721	Remote Similarity	NPD1445	Approved
0.6716	Remote Similarity	NPD3094	Phase 2
0.6716	Remote Similarity	NPD2797	Approved
0.6715	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD1048	Approved
0.6713	Remote Similarity	NPD1652	Phase 2
0.6713	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD9495	Approved
0.6693	Remote Similarity	NPD2629	Approved
0.6692	Remote Similarity	NPD4359	Approved
0.669	Remote Similarity	NPD5762	Approved
0.669	Remote Similarity	NPD5763	Approved
0.6689	Remote Similarity	NPD1006	Clinical (unspecified phase)
0.6689	Remote Similarity	NPD2801	Approved
0.6667	Remote Similarity	NPD1512	Approved
0.6667	Remote Similarity	NPD1281	Approved
0.6667	Remote Similarity	NPD1091	Approved
0.6667	Remote Similarity	NPD2799	Discontinued
0.6645	Remote Similarity	NPD3817	Phase 2
0.6644	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6643	Remote Similarity	NPD2492	Phase 1
0.6643	Remote Similarity	NPD5314	Approved
0.6642	Remote Similarity	NPD3225	Approved
0.6642	Remote Similarity	NPD5163	Phase 2
0.6641	Remote Similarity	NPD3019	Approved
0.6641	Remote Similarity	NPD2932	Approved
0.6639	Remote Similarity	NPD1238	Approved
0.6637	Remote Similarity	NPD9094	Approved
0.6623	Remote Similarity	NPD6234	Discontinued
0.662	Remote Similarity	NPD1551	Phase 2
0.662	Remote Similarity	NPD6032	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