NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	150.07
Volume:	162.698
LogP:	2.826
LogD:	2.179
LogS:	-3.162
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.699
Synthetic Accessibility Score:	1.271
Fsp3:	0.222
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.611
MDCK Permeability:	2.0505240172496997e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.295
Plasma Protein Binding (PPB):	82.51915740966797%
Volume Distribution (VD):	0.189
Pgp-substrate:	12.005865097045898%

ADMET: Metabolism

CYP1A2-inhibitor:	0.122
CYP1A2-substrate:	0.234
CYP2C19-inhibitor:	0.081
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.116
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.09
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	1.927
Half-life (T1/2):	0.886

ADMET: Toxicity

hERG Blockers:	0.108
Human Hepatotoxicity (H-HT):	0.456
Drug-inuced Liver Injury (DILI):	0.902
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.382
Maximum Recommended Daily Dose:	0.008
Skin Sensitization:	0.107
Carcinogencity:	0.035
Eye Corrosion:	0.044
Eye Irritation:	0.99
Respiratory Toxicity:	0.083

Download Data

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

Natural Product: NPC217621

Natural Product ID:	NPC217621
*Common Name:**	4-Ethylbenzoic Acid
IUPAC Name:	4-ethylbenzoic acid
Synonyms:	4-Ethyl-Benzoic Acid
Standard InCHIKey:	ZQVKTHRQIXSMGY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H10O2/c1-2-7-3-5-8(6-4-7)9(10)11/h3-6H,2H2,1H3,(H,10,11)
SMILES:	CCc1ccc(cc1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL100768
PubChem CID:	12086
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0002565] Benzoic acids

*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

☑ 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
Others	3
Potency	2

Activity Type	# Activity
Individual Protein	2
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT27	Others	Unspecified		Hammett constant	=	-0.15	n.a.	PMID[479564]
NPT35	Others	n.a.		LogD	=	2.89	n.a.	PMID[479565]
NPT2	Others	Unspecified		Hammett constant	=	-0.15	n.a.	PMID[479566]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[479567]
NPT8	Individual Protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	89125.1	nM	PMID[479567]

☑ 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 NPC217621 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	225
0.1-0.2	1403
0.2-0.3	3657
0.3-0.4	10534
0.4-0.5	11718
0.5-0.6	10886
0.6-0.7	3590
0.7-0.8	614
0.8-0.85	47
0.85-0.9	13
0.9-0.95	4
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9787	High Similarity	NPC304873
0.9787	High Similarity	NPC25458
0.9783	High Similarity	NPC253423
0.9485	High Similarity	NPC105899
0.9462	High Similarity	NPC61944
0.9293	High Similarity	NPC249811
0.9263	High Similarity	NPC229242
0.913	High Similarity	NPC62765
0.9082	High Similarity	NPC255676
0.901	High Similarity	NPC318327
0.8932	High Similarity	NPC66208
0.8788	High Similarity	NPC284477
0.8776	High Similarity	NPC228435
0.8776	High Similarity	NPC203925
0.8696	High Similarity	NPC318107
0.8687	High Similarity	NPC282895
0.8687	High Similarity	NPC70624
0.8679	High Similarity	NPC186933
0.86	High Similarity	NPC188895
0.8557	High Similarity	NPC130398
0.8526	High Similarity	NPC70940
0.8526	High Similarity	NPC86670
0.8526	High Similarity	NPC274455
0.8511	High Similarity	NPC329064
0.8505	High Similarity	NPC476357
0.8476	Intermediate Similarity	NPC474057
0.8462	Intermediate Similarity	NPC85493
0.8454	Intermediate Similarity	NPC261181
0.844	Intermediate Similarity	NPC160199
0.8438	Intermediate Similarity	NPC110704
0.8404	Intermediate Similarity	NPC322387
0.8384	Intermediate Similarity	NPC249912
0.8384	Intermediate Similarity	NPC92754
0.8384	Intermediate Similarity	NPC276775
0.837	Intermediate Similarity	NPC285773
0.8349	Intermediate Similarity	NPC158157
0.8333	Intermediate Similarity	NPC329556
0.8302	Intermediate Similarity	NPC260818
0.83	Intermediate Similarity	NPC225060
0.83	Intermediate Similarity	NPC35448
0.83	Intermediate Similarity	NPC78701
0.8288	Intermediate Similarity	NPC472708
0.8252	Intermediate Similarity	NPC249067
0.8224	Intermediate Similarity	NPC321852
0.8218	Intermediate Similarity	NPC146351
0.8218	Intermediate Similarity	NPC325497
0.819	Intermediate Similarity	NPC34715
0.8155	Intermediate Similarity	NPC291426
0.8142	Intermediate Similarity	NPC165197
0.8137	Intermediate Similarity	NPC42211
0.8131	Intermediate Similarity	NPC476003
0.8119	Intermediate Similarity	NPC175852
0.8119	Intermediate Similarity	NPC210529
0.8119	Intermediate Similarity	NPC160548
0.8095	Intermediate Similarity	NPC37914
0.8095	Intermediate Similarity	NPC187913
0.8091	Intermediate Similarity	NPC161304
0.8077	Intermediate Similarity	NPC324786
0.8077	Intermediate Similarity	NPC31786
0.8073	Intermediate Similarity	NPC153053
0.8073	Intermediate Similarity	NPC196673
0.8073	Intermediate Similarity	NPC211421
0.807	Intermediate Similarity	NPC269923
0.807	Intermediate Similarity	NPC25168
0.807	Intermediate Similarity	NPC167323
0.8056	Intermediate Similarity	NPC158282
0.8043	Intermediate Similarity	NPC127343
0.8039	Intermediate Similarity	NPC118343
0.8037	Intermediate Similarity	NPC95172
0.8019	Intermediate Similarity	NPC226699
0.8019	Intermediate Similarity	NPC211439
0.8	Intermediate Similarity	NPC209632
0.8	Intermediate Similarity	NPC81808
0.8	Intermediate Similarity	NPC306740
0.8	Intermediate Similarity	NPC274839
0.8	Intermediate Similarity	NPC297193
0.7982	Intermediate Similarity	NPC128368
0.7982	Intermediate Similarity	NPC272524
0.7981	Intermediate Similarity	NPC160382
0.7981	Intermediate Similarity	NPC301943
0.7981	Intermediate Similarity	NPC474365
0.7979	Intermediate Similarity	NPC288903
0.7979	Intermediate Similarity	NPC44830
0.7963	Intermediate Similarity	NPC475002
0.7963	Intermediate Similarity	NPC95126
0.7961	Intermediate Similarity	NPC52472
0.7961	Intermediate Similarity	NPC473325
0.7944	Intermediate Similarity	NPC83628
0.7944	Intermediate Similarity	NPC224584
0.7944	Intermediate Similarity	NPC469636
0.7944	Intermediate Similarity	NPC265407
0.7931	Intermediate Similarity	NPC85511
0.7925	Intermediate Similarity	NPC37622
0.7925	Intermediate Similarity	NPC30594
0.7925	Intermediate Similarity	NPC184658
0.7925	Intermediate Similarity	NPC6984
0.7925	Intermediate Similarity	NPC119271
0.7917	Intermediate Similarity	NPC474211
0.7905	Intermediate Similarity	NPC329282
0.7905	Intermediate Similarity	NPC114594
0.7895	Intermediate Similarity	NPC168855
0.7885	Intermediate Similarity	NPC45613
0.7876	Intermediate Similarity	NPC161943
0.7876	Intermediate Similarity	NPC474890
0.7876	Intermediate Similarity	NPC273282
0.7876	Intermediate Similarity	NPC41567
0.7864	Intermediate Similarity	NPC245561
0.7863	Intermediate Similarity	NPC117794
0.7857	Intermediate Similarity	NPC83718
0.785	Intermediate Similarity	NPC29883
0.785	Intermediate Similarity	NPC141523
0.785	Intermediate Similarity	NPC56493
0.7845	Intermediate Similarity	NPC472703
0.783	Intermediate Similarity	NPC172483
0.7826	Intermediate Similarity	NPC50192
0.7822	Intermediate Similarity	NPC172925
0.7812	Intermediate Similarity	NPC294134
0.7812	Intermediate Similarity	NPC474354
0.7812	Intermediate Similarity	NPC95965
0.781	Intermediate Similarity	NPC13426
0.781	Intermediate Similarity	NPC89886
0.781	Intermediate Similarity	NPC274443
0.781	Intermediate Similarity	NPC60679
0.781	Intermediate Similarity	NPC247976
0.7798	Intermediate Similarity	NPC210089
0.7797	Intermediate Similarity	NPC287473
0.7797	Intermediate Similarity	NPC472592
0.7788	Intermediate Similarity	NPC125252
0.7788	Intermediate Similarity	NPC240664
0.7788	Intermediate Similarity	NPC469481
0.7778	Intermediate Similarity	NPC269023
0.7778	Intermediate Similarity	NPC99846
0.7778	Intermediate Similarity	NPC100551
0.7778	Intermediate Similarity	NPC10251
0.7778	Intermediate Similarity	NPC17417
0.7778	Intermediate Similarity	NPC472704
0.7778	Intermediate Similarity	NPC275145
0.7766	Intermediate Similarity	NPC145053
0.7757	Intermediate Similarity	NPC317592
0.7748	Intermediate Similarity	NPC242136
0.7748	Intermediate Similarity	NPC237366
0.7748	Intermediate Similarity	NPC307651
0.7748	Intermediate Similarity	NPC474363
0.7748	Intermediate Similarity	NPC471721
0.7736	Intermediate Similarity	NPC472221
0.7736	Intermediate Similarity	NPC472222
0.7732	Intermediate Similarity	NPC93843
0.7727	Intermediate Similarity	NPC270699
0.7727	Intermediate Similarity	NPC474314
0.7727	Intermediate Similarity	NPC82899
0.7714	Intermediate Similarity	NPC244427
0.7714	Intermediate Similarity	NPC222390
0.7712	Intermediate Similarity	NPC236189
0.7708	Intermediate Similarity	NPC44546
0.7706	Intermediate Similarity	NPC196246
0.7706	Intermediate Similarity	NPC174099
0.7706	Intermediate Similarity	NPC214067
0.7706	Intermediate Similarity	NPC216122
0.7706	Intermediate Similarity	NPC93084
0.7706	Intermediate Similarity	NPC251854
0.7699	Intermediate Similarity	NPC128825
0.7699	Intermediate Similarity	NPC131192
0.7692	Intermediate Similarity	NPC280869
0.7679	Intermediate Similarity	NPC474685
0.7679	Intermediate Similarity	NPC93181
0.7677	Intermediate Similarity	NPC1793
0.7677	Intermediate Similarity	NPC173443
0.7672	Intermediate Similarity	NPC301987
0.7672	Intermediate Similarity	NPC115188
0.7672	Intermediate Similarity	NPC272454
0.7672	Intermediate Similarity	NPC222876
0.7672	Intermediate Similarity	NPC35856
0.7672	Intermediate Similarity	NPC244994
0.7672	Intermediate Similarity	NPC159760
0.7672	Intermediate Similarity	NPC178395
0.7672	Intermediate Similarity	NPC472981
0.7672	Intermediate Similarity	NPC179092
0.7672	Intermediate Similarity	NPC26433
0.7672	Intermediate Similarity	NPC292665
0.767	Intermediate Similarity	NPC289201
0.7667	Intermediate Similarity	NPC115797
0.7667	Intermediate Similarity	NPC51448
0.7664	Intermediate Similarity	NPC269457
0.7664	Intermediate Similarity	NPC13495
0.7658	Intermediate Similarity	NPC17693
0.7658	Intermediate Similarity	NPC231717
0.7658	Intermediate Similarity	NPC93287
0.7652	Intermediate Similarity	NPC233165
0.7652	Intermediate Similarity	NPC184579
0.7636	Intermediate Similarity	NPC133308
0.7636	Intermediate Similarity	NPC474157
0.7636	Intermediate Similarity	NPC305912
0.7636	Intermediate Similarity	NPC1082
0.7636	Intermediate Similarity	NPC167504
0.7632	Intermediate Similarity	NPC228318
0.7627	Intermediate Similarity	NPC477153
0.7627	Intermediate Similarity	NPC228739
0.7615	Intermediate Similarity	NPC17525
0.7615	Intermediate Similarity	NPC474364
0.7611	Intermediate Similarity	NPC322197

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 NPC217621 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	251
0.1-0.2	913
0.2-0.3	1335
0.3-0.4	2804
0.4-0.5	2348
0.5-0.6	1073
0.6-0.7	340
0.7-0.8	59
0.8-0.85	20
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.913	High Similarity	NPD9256	Approved
0.913	High Similarity	NPD9258	Approved
0.8696	High Similarity	NPD9257	Approved
0.8696	High Similarity	NPD9259	Approved
0.8679	High Similarity	NPD5951	Approved
0.8641	High Similarity	NPD6831	Clinical (unspecified phase)
0.8617	High Similarity	NPD800	Approved
0.8526	High Similarity	NPD1090	Approved
0.8526	High Similarity	NPD1089	Approved
0.8526	High Similarity	NPD1086	Approved
0.8454	Intermediate Similarity	NPD1202	Approved
0.84	Intermediate Similarity	NPD2066	Phase 3
0.8396	Intermediate Similarity	NPD9508	Approved
0.837	Intermediate Similarity	NPD9491	Approved
0.8351	Intermediate Similarity	NPD1088	Approved
0.8333	Intermediate Similarity	NPD1929	Approved
0.8333	Intermediate Similarity	NPD1930	Approved
0.8333	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD1237	Approved
0.8247	Intermediate Similarity	NPD1239	Approved
0.8235	Intermediate Similarity	NPD1932	Approved
0.8214	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8211	Intermediate Similarity	NPD1087	Approved
0.8182	Intermediate Similarity	NPD1693	Approved
0.8152	Intermediate Similarity	NPD226	Approved
0.8119	Intermediate Similarity	NPD9495	Approved
0.8077	Intermediate Similarity	NPD164	Approved
0.8039	Intermediate Similarity	NPD1238	Approved
0.802	Intermediate Similarity	NPD1564	Approved
0.802	Intermediate Similarity	NPD1566	Phase 3
0.802	Intermediate Similarity	NPD1565	Approved
0.8	Intermediate Similarity	NPD9260	Approved
0.7982	Intermediate Similarity	NPD5277	Phase 2
0.7944	Intermediate Similarity	NPD2329	Discontinued
0.7935	Intermediate Similarity	NPD9490	Approved
0.7931	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD1317	Discontinued
0.785	Intermediate Similarity	NPD9263	Approved
0.785	Intermediate Similarity	NPD9267	Approved
0.785	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.785	Intermediate Similarity	NPD9264	Approved
0.7826	Intermediate Similarity	NPD225	Approved
0.7826	Intermediate Similarity	NPD227	Approved
0.7822	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7798	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2182	Approved
0.7778	Intermediate Similarity	NPD74	Approved
0.7778	Intermediate Similarity	NPD9266	Approved
0.7723	Intermediate Similarity	NPD1563	Approved
0.7723	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7699	Intermediate Similarity	NPD9493	Approved
0.7679	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD5347	Phase 2
0.7677	Intermediate Similarity	NPD5346	Phase 2
0.7653	Intermediate Similarity	NPD4793	Discontinued
0.7573	Intermediate Similarity	NPD1989	Approved
0.7565	Intermediate Similarity	NPD9545	Approved
0.7541	Intermediate Similarity	NPD6966	Discovery
0.7541	Intermediate Similarity	NPD7008	Discontinued
0.7541	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7522	Intermediate Similarity	NPD2629	Approved
0.75	Intermediate Similarity	NPD9716	Approved
0.7477	Intermediate Similarity	NPD9261	Approved
0.7458	Intermediate Similarity	NPD6287	Discontinued
0.7436	Intermediate Similarity	NPD1104	Approved
0.7417	Intermediate Similarity	NPD1888	Phase 1
0.7411	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD5909	Discontinued
0.7368	Intermediate Similarity	NPD1246	Approved
0.7368	Intermediate Similarity	NPD9281	Approved
0.7355	Intermediate Similarity	NPD1164	Approved
0.735	Intermediate Similarity	NPD1245	Approved
0.7321	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD6647	Phase 2
0.725	Intermediate Similarity	NPD9717	Approved
0.7244	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD942	Approved
0.7203	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7167	Intermediate Similarity	NPD1201	Approved
0.7158	Intermediate Similarity	NPD9294	Approved
0.7155	Intermediate Similarity	NPD256	Approved
0.7155	Intermediate Similarity	NPD255	Approved
0.7154	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2345	Approved
0.7132	Intermediate Similarity	NPD4308	Phase 3
0.7129	Intermediate Similarity	NPD650	Approved
0.7107	Intermediate Similarity	NPD4878	Approved
0.71	Intermediate Similarity	NPD5734	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD3672	Approved
0.7087	Intermediate Similarity	NPD3673	Approved
0.7083	Intermediate Similarity	NPD1889	Phase 1
0.7075	Intermediate Similarity	NPD844	Approved
0.7073	Intermediate Similarity	NPD1470	Approved
0.7071	Intermediate Similarity	NPD3971	Phase 1
0.7063	Intermediate Similarity	NPD411	Approved
0.7063	Intermediate Similarity	NPD3764	Approved
0.7059	Intermediate Similarity	NPD4105	Approved
0.7059	Intermediate Similarity	NPD4102	Approved
0.7049	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD5159	Phase 2
0.7049	Intermediate Similarity	NPD5157	Phase 1
0.7019	Intermediate Similarity	NPD7609	Phase 3
0.7009	Intermediate Similarity	NPD288	Approved
0.7	Intermediate Similarity	NPD9272	Approved
0.7	Intermediate Similarity	NPD5305	Approved
0.7	Intermediate Similarity	NPD5306	Approved
0.6992	Remote Similarity	NPD1283	Approved
0.6983	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6952	Remote Similarity	NPD7631	Approved
0.6947	Remote Similarity	NPD5404	Approved
0.6947	Remote Similarity	NPD5405	Approved
0.6947	Remote Similarity	NPD5406	Approved
0.6947	Remote Similarity	NPD5408	Approved
0.6944	Remote Similarity	NPD253	Approved
0.6942	Remote Similarity	NPD4106	Approved
0.6942	Remote Similarity	NPD4135	Approved
0.6942	Remote Similarity	NPD4136	Approved
0.6935	Remote Similarity	NPD1203	Approved
0.693	Remote Similarity	NPD2067	Discontinued
0.6929	Remote Similarity	NPD2313	Discontinued
0.6917	Remote Similarity	NPD9268	Approved
0.6916	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD2346	Discontinued
0.6891	Remote Similarity	NPD7610	Discontinued
0.6885	Remote Similarity	NPD4807	Approved
0.6885	Remote Similarity	NPD4806	Approved
0.6885	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD9712	Approved
0.688	Remote Similarity	NPD2798	Approved
0.6875	Remote Similarity	NPD5048	Discontinued
0.6866	Remote Similarity	NPD4628	Phase 3
0.6866	Remote Similarity	NPD7003	Approved
0.6864	Remote Similarity	NPD4198	Discontinued
0.686	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3495	Discontinued
0.6852	Remote Similarity	NPD9566	Approved
0.6847	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD7009	Phase 2
0.6829	Remote Similarity	NPD9269	Phase 2
0.6829	Remote Similarity	NPD1608	Approved
0.6829	Remote Similarity	NPD3972	Approved
0.6822	Remote Similarity	NPD4307	Phase 2
0.6822	Remote Similarity	NPD6049	Phase 2
0.6822	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1616	Discontinued
0.6818	Remote Similarity	NPD2935	Discontinued
0.6807	Remote Similarity	NPD9568	Approved
0.6803	Remote Similarity	NPD9693	Approved
0.6803	Remote Similarity	NPD9692	Approved
0.68	Remote Similarity	NPD2797	Approved
0.6796	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD9711	Approved
0.6789	Remote Similarity	NPD9710	Approved
0.6769	Remote Similarity	NPD447	Suspended
0.6768	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD2859	Approved
0.6759	Remote Similarity	NPD2860	Approved
0.675	Remote Similarity	NPD1758	Phase 1
0.6748	Remote Similarity	NPD1281	Approved
0.6746	Remote Similarity	NPD4980	Approved
0.6744	Remote Similarity	NPD7714	Approved
0.6744	Remote Similarity	NPD7715	Approved
0.6742	Remote Similarity	NPD2799	Discontinued
0.6731	Remote Similarity	NPD1101	Approved
0.6729	Remote Similarity	NPD1066	Discontinued
0.6729	Remote Similarity	NPD845	Approved
0.6727	Remote Similarity	NPD3020	Approved
0.6724	Remote Similarity	NPD3642	Approved
0.6724	Remote Similarity	NPD3643	Approved
0.6724	Remote Similarity	NPD3644	Approved
0.6721	Remote Similarity	NPD3019	Approved
0.6721	Remote Similarity	NPD4626	Approved
0.6721	Remote Similarity	NPD2932	Approved
0.672	Remote Similarity	NPD1574	Approved
0.6718	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD1607	Approved
0.6696	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD2652	Approved
0.6695	Remote Similarity	NPD2650	Approved
0.6695	Remote Similarity	NPD1241	Discontinued
0.6694	Remote Similarity	NPD1759	Phase 1
0.6692	Remote Similarity	NPD1551	Phase 2
0.6667	Remote Similarity	NPD2933	Approved
0.6667	Remote Similarity	NPD689	Discontinued
0.6667	Remote Similarity	NPD2934	Approved
0.6667	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6642	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD230	Phase 1
0.6636	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1508	Approved
0.6617	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD520	Approved
0.6614	Remote Similarity	NPD6085	Phase 2
0.6614	Remote Similarity	NPD258	Approved
0.6614	Remote Similarity	NPD5740	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