NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	240.1
Volume:	240.957
LogP:	2.425
LogD:	2.54
LogS:	-3.19
# Rotatable Bonds:	6
TPSA:	53.99
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.735
Synthetic Accessibility Score:	1.637
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.503
MDCK Permeability:	3.6124845792073756e-05
Pgp-inhibitor:	0.742
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.094

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.736
Plasma Protein Binding (PPB):	54.878028869628906%
Volume Distribution (VD):	0.64
Pgp-substrate:	16.853500366210938%

ADMET: Metabolism

CYP1A2-inhibitor:	0.915
CYP1A2-substrate:	0.955
CYP2C19-inhibitor:	0.629
CYP2C19-substrate:	0.882
CYP2C9-inhibitor:	0.129
CYP2C9-substrate:	0.815
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.868
CYP3A4-inhibitor:	0.151
CYP3A4-substrate:	0.449

ADMET: Excretion

Clearance (CL):	9.688
Half-life (T1/2):	0.892

ADMET: Toxicity

hERG Blockers:	0.082
Human Hepatotoxicity (H-HT):	0.024
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.021
Skin Sensitization:	0.3
Carcinogencity:	0.035
Eye Corrosion:	0.047
Eye Irritation:	0.944
Respiratory Toxicity:	0.06

Download Data

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

Natural Product: NPC288743

Natural Product ID:	NPC288743
*Common Name:**	Ethyltrimethoxy Benzoate
IUPAC Name:	ethyl 3,4,5-trimethoxybenzoate
Synonyms:	Ethyltrimethoxy Benzoate
Standard InCHIKey:	UEOFNBCUGJADBM-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16O5/c1-5-17-12(13)8-6-9(14-2)11(16-4)10(7-8)15-3/h6-7H,5H2,1-4H3
SMILES:	CCOC(=O)c1cc(OC)c(c(c1)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL501163
PubChem CID:	231162
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0001251] Gallic acid 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
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1744	Discaria serratifolia	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9180	Pyrostegia venusta	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO998	Justicia hayatai	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3580	Rana amurensis	Species	Ranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13016	Viscaria viscosa	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11636	Ideopsis similis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3469	Pteris dactylina	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12510	Aronia arbutifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13070	Clibadium mexiae	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
MIC	11

Activity Type	# Activity
Organism	11

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT328	Organism	Epidermophyton floccosum	Epidermophyton floccosum	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	250.0	ug.mL-1	PMID[489564]
NPT330	Organism	Trichophyton mentagrophytes	Trichophyton mentagrophytes	MIC	>	250.0	ug.mL-1	PMID[489564]

☑ 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 NPC288743 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	384
0.1-0.2	1788
0.2-0.3	5355
0.3-0.4	10236
0.4-0.5	7003
0.5-0.6	3825
0.6-0.7	6980
0.7-0.8	6498
0.8-0.85	541
0.85-0.9	65
0.9-0.95	19
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9762	High Similarity	NPC299010
0.9462	High Similarity	NPC155098
0.9297	High Similarity	NPC304747
0.9291	High Similarity	NPC154275
0.9248	High Similarity	NPC95679
0.9248	High Similarity	NPC25305
0.9248	High Similarity	NPC125417
0.9248	High Similarity	NPC110899
0.9248	High Similarity	NPC112068
0.9179	High Similarity	NPC207516
0.913	High Similarity	NPC213482
0.9058	High Similarity	NPC27106
0.9008	High Similarity	NPC285776
0.8963	High Similarity	NPC474274
0.8963	High Similarity	NPC157944
0.8955	High Similarity	NPC38101
0.8955	High Similarity	NPC18646
0.8947	High Similarity	NPC156124
0.8947	High Similarity	NPC1321
0.8947	High Similarity	NPC304929
0.8931	High Similarity	NPC153547
0.8889	High Similarity	NPC156892
0.8873	High Similarity	NPC473091
0.8828	High Similarity	NPC288238
0.8815	High Similarity	NPC274613
0.8815	High Similarity	NPC143649
0.8815	High Similarity	NPC208760
0.8806	High Similarity	NPC283823
0.8806	High Similarity	NPC159418
0.8797	High Similarity	NPC264145
0.8788	High Similarity	NPC150809
0.8777	High Similarity	NPC28326
0.8769	High Similarity	NPC173608
0.8759	High Similarity	NPC470962
0.875	High Similarity	NPC75695
0.8741	High Similarity	NPC237330
0.874	High Similarity	NPC222175
0.8731	High Similarity	NPC111888
0.8714	High Similarity	NPC134975
0.8705	High Similarity	NPC46180
0.8702	High Similarity	NPC127604
0.8696	High Similarity	NPC225036
0.8696	High Similarity	NPC105525
0.8696	High Similarity	NPC75763
0.8696	High Similarity	NPC12218
0.8696	High Similarity	NPC4796
0.8692	High Similarity	NPC145134
0.869	High Similarity	NPC310661
0.869	High Similarity	NPC105827
0.863	High Similarity	NPC186507
0.8626	High Similarity	NPC27352
0.8623	High Similarity	NPC233780
0.8623	High Similarity	NPC239943
0.8623	High Similarity	NPC44573
0.8621	High Similarity	NPC228662
0.8621	High Similarity	NPC473732
0.8613	High Similarity	NPC209229
0.8603	High Similarity	NPC311339
0.8592	High Similarity	NPC136278
0.8582	High Similarity	NPC469615
0.8582	High Similarity	NPC473090
0.8571	High Similarity	NPC145425
0.8571	High Similarity	NPC58229
0.8571	High Similarity	NPC222185
0.8562	High Similarity	NPC475116
0.8552	High Similarity	NPC96501
0.854	High Similarity	NPC44245
0.854	High Similarity	NPC211386
0.854	High Similarity	NPC72796
0.8531	High Similarity	NPC195919
0.8531	High Similarity	NPC216314
0.8531	High Similarity	NPC120924
0.8527	High Similarity	NPC295317
0.8527	High Similarity	NPC225245
0.8521	High Similarity	NPC469683
0.8521	High Similarity	NPC293201
0.8521	High Similarity	NPC113089
0.8521	High Similarity	NPC213900
0.8521	High Similarity	NPC182842
0.8511	High Similarity	NPC299154
0.8511	High Similarity	NPC185607
0.8511	High Similarity	NPC29536
0.8507	High Similarity	NPC226855
0.8503	High Similarity	NPC238672
0.8503	High Similarity	NPC144801
0.8503	High Similarity	NPC281477
0.8503	High Similarity	NPC197188
0.8503	High Similarity	NPC43872
0.8503	High Similarity	NPC291510
0.8503	High Similarity	NPC116850
0.85	High Similarity	NPC207418
0.85	High Similarity	NPC326065
0.8493	Intermediate Similarity	NPC474663
0.8489	Intermediate Similarity	NPC46947
0.8485	Intermediate Similarity	NPC473626
0.8483	Intermediate Similarity	NPC474648
0.8478	Intermediate Similarity	NPC160425
0.8473	Intermediate Similarity	NPC474691
0.8472	Intermediate Similarity	NPC472969
0.8472	Intermediate Similarity	NPC205522
0.8472	Intermediate Similarity	NPC294972
0.8467	Intermediate Similarity	NPC45404
0.8462	Intermediate Similarity	NPC471590
0.8462	Intermediate Similarity	NPC474446
0.8462	Intermediate Similarity	NPC310373
0.8456	Intermediate Similarity	NPC1913
0.8456	Intermediate Similarity	NPC26353
0.8456	Intermediate Similarity	NPC472860
0.8456	Intermediate Similarity	NPC137669
0.8451	Intermediate Similarity	NPC476054
0.8451	Intermediate Similarity	NPC50221
0.8451	Intermediate Similarity	NPC114242
0.8451	Intermediate Similarity	NPC121573
0.8451	Intermediate Similarity	NPC9966
0.8451	Intermediate Similarity	NPC70853
0.8451	Intermediate Similarity	NPC22176
0.8451	Intermediate Similarity	NPC190587
0.8451	Intermediate Similarity	NPC226738
0.8451	Intermediate Similarity	NPC229036
0.8446	Intermediate Similarity	NPC16082
0.8446	Intermediate Similarity	NPC199926
0.8446	Intermediate Similarity	NPC79998
0.8446	Intermediate Similarity	NPC82592
0.8444	Intermediate Similarity	NPC19242
0.8438	Intermediate Similarity	NPC166591
0.8433	Intermediate Similarity	NPC109275
0.8429	Intermediate Similarity	NPC203351
0.8425	Intermediate Similarity	NPC29056
0.8425	Intermediate Similarity	NPC62354
0.8414	Intermediate Similarity	NPC476394
0.8414	Intermediate Similarity	NPC98809
0.8414	Intermediate Similarity	NPC63256
0.8414	Intermediate Similarity	NPC10304
0.8414	Intermediate Similarity	NPC183236
0.8414	Intermediate Similarity	NPC107636
0.8403	Intermediate Similarity	NPC110639
0.8403	Intermediate Similarity	NPC153620
0.8403	Intermediate Similarity	NPC283002
0.8403	Intermediate Similarity	NPC215932
0.8403	Intermediate Similarity	NPC165389
0.8403	Intermediate Similarity	NPC106461
0.8403	Intermediate Similarity	NPC24257
0.8403	Intermediate Similarity	NPC231013
0.8403	Intermediate Similarity	NPC302408
0.8403	Intermediate Similarity	NPC40818
0.8403	Intermediate Similarity	NPC14958
0.84	Intermediate Similarity	NPC289811
0.84	Intermediate Similarity	NPC160780
0.84	Intermediate Similarity	NPC325122
0.84	Intermediate Similarity	NPC87317
0.8394	Intermediate Similarity	NPC241341
0.8394	Intermediate Similarity	NPC36437
0.8394	Intermediate Similarity	NPC233018
0.8392	Intermediate Similarity	NPC207732
0.8392	Intermediate Similarity	NPC184702
0.8392	Intermediate Similarity	NPC108455
0.8389	Intermediate Similarity	NPC150227
0.838	Intermediate Similarity	NPC297985
0.838	Intermediate Similarity	NPC312256
0.837	Intermediate Similarity	NPC48315
0.8369	Intermediate Similarity	NPC50823
0.8367	Intermediate Similarity	NPC163883
0.8367	Intermediate Similarity	NPC474388
0.8367	Intermediate Similarity	NPC474170
0.8367	Intermediate Similarity	NPC151425
0.8367	Intermediate Similarity	NPC104353
0.8367	Intermediate Similarity	NPC472535
0.8367	Intermediate Similarity	NPC93498
0.8367	Intermediate Similarity	NPC198615
0.8358	Intermediate Similarity	NPC158654
0.8358	Intermediate Similarity	NPC194841
0.8356	Intermediate Similarity	NPC238366
0.8346	Intermediate Similarity	NPC220540
0.8345	Intermediate Similarity	NPC119660
0.8345	Intermediate Similarity	NPC299923
0.8345	Intermediate Similarity	NPC117463
0.8345	Intermediate Similarity	NPC470511
0.8345	Intermediate Similarity	NPC85233
0.8345	Intermediate Similarity	NPC93034
0.8344	Intermediate Similarity	NPC24627
0.8344	Intermediate Similarity	NPC239966
0.8344	Intermediate Similarity	NPC119125
0.8344	Intermediate Similarity	NPC203020
0.8344	Intermediate Similarity	NPC53889
0.8344	Intermediate Similarity	NPC166277
0.8333	Intermediate Similarity	NPC37065
0.8333	Intermediate Similarity	NPC84935
0.8333	Intermediate Similarity	NPC287275
0.8333	Intermediate Similarity	NPC77679
0.8333	Intermediate Similarity	NPC165512
0.8333	Intermediate Similarity	NPC472917
0.8333	Intermediate Similarity	NPC224687
0.8333	Intermediate Similarity	NPC108545
0.8333	Intermediate Similarity	NPC262282
0.8333	Intermediate Similarity	NPC296575
0.8333	Intermediate Similarity	NPC190020
0.8333	Intermediate Similarity	NPC98356
0.8322	Intermediate Similarity	NPC122623
0.8322	Intermediate Similarity	NPC241774
0.8322	Intermediate Similarity	NPC471746

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 NPC288743 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	329
0.1-0.2	991
0.2-0.3	2034
0.3-0.4	2626
0.4-0.5	1630
0.5-0.6	1026
0.6-0.7	382
0.7-0.8	117
0.8-0.85	14
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8947	High Similarity	NPD230	Phase 1
0.8571	High Similarity	NPD5353	Approved
0.8472	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD3817	Phase 2
0.8267	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8231	Intermediate Similarity	NPD9268	Approved
0.8182	Intermediate Similarity	NPD5242	Approved
0.8129	Intermediate Similarity	NPD447	Suspended
0.8121	Intermediate Similarity	NPD6386	Approved
0.8121	Intermediate Similarity	NPD6385	Approved
0.812	Intermediate Similarity	NPD9269	Phase 2
0.8088	Intermediate Similarity	NPD9494	Approved
0.8042	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8039	Intermediate Similarity	NPD919	Approved
0.8026	Intermediate Similarity	NPD3882	Suspended
0.8014	Intermediate Similarity	NPD6799	Approved
0.8013	Intermediate Similarity	NPD2801	Approved
0.7987	Intermediate Similarity	NPD5494	Approved
0.7947	Intermediate Similarity	NPD1934	Approved
0.7895	Intermediate Similarity	NPD1465	Phase 2
0.7885	Intermediate Similarity	NPD6232	Discontinued
0.7879	Intermediate Similarity	NPD9545	Approved
0.7862	Intermediate Similarity	NPD5844	Phase 1
0.7838	Intermediate Similarity	NPD2532	Approved
0.7838	Intermediate Similarity	NPD2534	Approved
0.7838	Intermediate Similarity	NPD2533	Approved
0.7821	Intermediate Similarity	NPD1247	Approved
0.7786	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2796	Approved
0.777	Intermediate Similarity	NPD1511	Approved
0.777	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD7473	Discontinued
0.7733	Intermediate Similarity	NPD920	Approved
0.7717	Intermediate Similarity	NPD1358	Approved
0.7697	Intermediate Similarity	NPD6599	Discontinued
0.7688	Intermediate Similarity	NPD3818	Discontinued
0.7687	Intermediate Similarity	NPD4628	Phase 3
0.7669	Intermediate Similarity	NPD5536	Phase 2
0.7667	Intermediate Similarity	NPD1512	Approved
0.7662	Intermediate Similarity	NPD7819	Suspended
0.7662	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7635	Intermediate Similarity	NPD6190	Approved
0.7622	Intermediate Similarity	NPD1933	Approved
0.7619	Intermediate Similarity	NPD1243	Approved
0.761	Intermediate Similarity	NPD3926	Phase 2
0.76	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD3146	Approved
0.7597	Intermediate Similarity	NPD37	Approved
0.7586	Intermediate Similarity	NPD1510	Phase 2
0.7586	Intermediate Similarity	NPD3748	Approved
0.7564	Intermediate Similarity	NPD4965	Approved
0.7564	Intermediate Similarity	NPD4967	Phase 2
0.7564	Intermediate Similarity	NPD4966	Approved
0.7562	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD6166	Phase 2
0.7561	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD1240	Approved
0.7534	Intermediate Similarity	NPD1551	Phase 2
0.7531	Intermediate Similarity	NPD7054	Approved
0.7518	Intermediate Similarity	NPD3705	Approved
0.7516	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1019	Discontinued
0.75	Intermediate Similarity	NPD5402	Approved
0.75	Intermediate Similarity	NPD17	Approved
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7485	Intermediate Similarity	NPD7472	Approved
0.7484	Intermediate Similarity	NPD6801	Discontinued
0.7468	Intermediate Similarity	NPD6234	Discontinued
0.7468	Intermediate Similarity	NPD4380	Phase 2
0.7467	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD3027	Phase 3
0.7464	Intermediate Similarity	NPD2981	Phase 2
0.7451	Intermediate Similarity	NPD1653	Approved
0.745	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD1607	Approved
0.7432	Intermediate Similarity	NPD1549	Phase 2
0.7419	Intermediate Similarity	NPD7411	Suspended
0.7415	Intermediate Similarity	NPD2935	Discontinued
0.741	Intermediate Similarity	NPD2983	Phase 2
0.741	Intermediate Similarity	NPD2982	Phase 2
0.7394	Intermediate Similarity	NPD7685	Pre-registration
0.7394	Intermediate Similarity	NPD6832	Phase 2
0.7383	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD1241	Discontinued
0.7365	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD3134	Approved
0.7349	Intermediate Similarity	NPD7808	Phase 3
0.7338	Intermediate Similarity	NPD9717	Approved
0.7338	Intermediate Similarity	NPD1608	Approved
0.7333	Intermediate Similarity	NPD3750	Approved
0.7333	Intermediate Similarity	NPD6797	Phase 2
0.7324	Intermediate Similarity	NPD3018	Phase 2
0.731	Intermediate Similarity	NPD943	Approved
0.7303	Intermediate Similarity	NPD4357	Discontinued
0.7296	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1296	Phase 2
0.7289	Intermediate Similarity	NPD7251	Discontinued
0.7286	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5403	Approved
0.7267	Intermediate Similarity	NPD2654	Approved
0.7255	Intermediate Similarity	NPD5401	Approved
0.7246	Intermediate Similarity	NPD1778	Approved
0.723	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3972	Approved
0.7172	Intermediate Similarity	NPD411	Approved
0.7171	Intermediate Similarity	NPD3887	Approved
0.7152	Intermediate Similarity	NPD7228	Approved
0.7143	Intermediate Similarity	NPD422	Phase 1
0.7125	Intermediate Similarity	NPD7768	Phase 2
0.7118	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5710	Approved
0.7117	Intermediate Similarity	NPD5711	Approved
0.7111	Intermediate Similarity	NPD5283	Phase 1
0.7107	Intermediate Similarity	NPD1006	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD4110	Phase 3
0.7105	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2186	Approved
0.7089	Intermediate Similarity	NPD6873	Phase 2
0.7083	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD9493	Approved
0.7075	Intermediate Similarity	NPD2979	Phase 3
0.7075	Intermediate Similarity	NPD1613	Approved
0.7075	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD2438	Suspended
0.7063	Intermediate Similarity	NPD1203	Approved
0.705	Intermediate Similarity	NPD5691	Approved
0.705	Intermediate Similarity	NPD5585	Approved
0.7045	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD1652	Phase 2
0.7039	Intermediate Similarity	NPD2800	Approved
0.7034	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1337	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD1281	Approved
0.702	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD2353	Approved
0.7007	Intermediate Similarity	NPD6233	Phase 2
0.7	Intermediate Similarity	NPD2799	Discontinued
0.6992	Remote Similarity	NPD2182	Approved
0.6987	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7038	Approved
0.6982	Remote Similarity	NPD7039	Approved
0.6982	Remote Similarity	NPD7240	Approved
0.6982	Remote Similarity	NPD6559	Discontinued
0.6975	Remote Similarity	NPD3749	Approved
0.6975	Remote Similarity	NPD6971	Discontinued
0.6968	Remote Similarity	NPD5297	Approved
0.6963	Remote Similarity	NPD228	Approved
0.6962	Remote Similarity	NPD824	Approved
0.6959	Remote Similarity	NPD3140	Approved
0.6959	Remote Similarity	NPD4307	Phase 2
0.6959	Remote Similarity	NPD3142	Approved
0.6957	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD8127	Discontinued
0.6951	Remote Similarity	NPD6959	Discontinued
0.695	Remote Similarity	NPD3496	Discontinued
0.6948	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD2219	Phase 1
0.6939	Remote Similarity	NPD3764	Approved
0.6928	Remote Similarity	NPD2403	Approved
0.6923	Remote Similarity	NPD5953	Discontinued
0.6914	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7229	Phase 3
0.6908	Remote Similarity	NPD7266	Discontinued
0.6905	Remote Similarity	NPD7286	Phase 2
0.6905	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD1283	Approved
0.6875	Remote Similarity	NPD1876	Approved
0.6867	Remote Similarity	NPD6651	Approved
0.6855	Remote Similarity	NPD7458	Discontinued
0.6855	Remote Similarity	NPD3226	Approved
0.6855	Remote Similarity	NPD3455	Phase 2
0.6852	Remote Similarity	NPD5977	Approved
0.6852	Remote Similarity	NPD5978	Approved
0.6842	Remote Similarity	NPD3539	Phase 1
0.6842	Remote Similarity	NPD6099	Approved
0.6842	Remote Similarity	NPD6100	Approved
0.6839	Remote Similarity	NPD2354	Approved
0.6836	Remote Similarity	NPD3473	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD3267	Approved
0.6828	Remote Similarity	NPD3266	Approved
0.6824	Remote Similarity	NPD2313	Discontinued
0.6824	Remote Similarity	NPD6798	Discontinued
0.6821	Remote Similarity	NPD6111	Discontinued
0.6818	Remote Similarity	NPD164	Approved
0.6815	Remote Similarity	NPD7004	Clinical (unspecified phase)

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