NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	136.05
Volume:	145.402
LogP:	2.497
LogD:	1.548
LogS:	-2.621
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.637
Synthetic Accessibility Score:	1.162
Fsp3:	0.125
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:	-4.8
MDCK Permeability:	1.5916393749648705e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.001
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.323
Plasma Protein Binding (PPB):	70.05146026611328%
Volume Distribution (VD):	0.244
Pgp-substrate:	19.71494483947754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.142
CYP1A2-substrate:	0.284
CYP2C19-inhibitor:	0.085
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.06
CYP2C9-substrate:	0.138
CYP2D6-inhibitor:	0.01
CYP2D6-substrate:	0.104
CYP3A4-inhibitor:	0.032
CYP3A4-substrate:	0.13

ADMET: Excretion

Clearance (CL):	2.261
Half-life (T1/2):	0.891

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.526
Drug-inuced Liver Injury (DILI):	0.875
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.717
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.164
Carcinogencity:	0.036
Eye Corrosion:	0.195
Eye Irritation:	0.994
Respiratory Toxicity:	0.076

Download Data

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

Natural Product: NPC253423

Natural Product ID:	NPC253423
*Common Name:**	4-Methylbenzoic Acid
IUPAC Name:	4-methylbenzoic acid
Synonyms:	4-Methyl-Benzoic Acid; P-Toluic Acid
Standard InCHIKey:	LPNBBFKOUUSUDB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C8H8O2/c1-6-2-4-7(5-3-6)8(9)10/h2-5H,1H3,(H,9,10)
SMILES:	Cc1ccc(cc1)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL21708
PubChem CID:	7470
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
IC50	4
Ki	2
MIC	1
Others	18
Potency	5

Activity Type	# Activity
Cell Line	2
Individual Protein	6
Organism	3
Others	17
SINGLE PROTEIN	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2230	Individual Protein	Thiopurine S-methyltransferase	Homo sapiens	IC50	=	288403.15	nM	PMID[537428]
NPT152	Individual Protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	21131.7	nM	PMID[537429]
NPT1070	Individual Protein	Sigma-1 receptor	Cavia porcellus	Ki	>	10000.0	nM	PMID[537434]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	100000.0	nM	PMID[537434]
NPT1070	Individual Protein	Sigma-1 receptor	Cavia porcellus	Inhibition	<	50.0	%	PMID[537434]
NPT83	Cell Line	MCF7	Homo sapiens	Activity	<	50.0	%	PMID[537434]
NPT27	Others	Unspecified		Hammett constant	=	-0.17	n.a.	PMID[537424]
NPT27	Others	Unspecified		Log 1/LD50	=	1.66	n.a.	PMID[537425]
NPT35	Others	n.a.		LogD	=	2.26	n.a.	PMID[537426]
NPT27	Others	Unspecified		Log LD50	=	-1.66	n.a.	PMID[537426]
NPT27	Others	Unspecified		IC50	=	288403.15	nM	PMID[537426]
NPT27	Others	Unspecified		Log 1/C	=	-0.23	n.a.	PMID[537426]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Log M	=	1.49	n.a.	PMID[537426]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Log M	=	1.56	n.a.	PMID[537426]
NPT2	Others	Unspecified		Hammett constant	=	-0.17	n.a.	PMID[537427]
NPT93	Individual Protein	Survival motor neuron protein	Homo sapiens	Potency	=	100.0	nM	PMID[537429]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	25118.9	nM	PMID[537429]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	220.0	nM	PMID[537430]
NPT35	Others	n.a.		pKa	=	4.37	n.a.	PMID[537430]
NPT2	Others	Unspecified		MIC	=	800000.0	nM	PMID[537431]
NPT35	Others	n.a.		LogD	=	-2.09	n.a.	PMID[537432]
NPT35	Others	n.a.		LogP	=	2.27	n.a.	PMID[537432]
NPT35	Others	n.a.		pKa	=	4.36	n.a.	PMID[537432]
NPT35	Others	n.a.		pKa	=	3.44	n.a.	PMID[537432]
NPT2	Others	Unspecified		FC	=	-0.52	n.a.	PMID[537432]
NPT2	Others	Unspecified		log1/Ki	=	2.43	n.a.	PMID[537433]
NPT24748	SINGLE PROTEIN	Sigma intracellular receptor 2	Homo sapiens	Ki	>	10000.0	nM	PMID[537434]
NPT24748	SINGLE PROTEIN	Sigma intracellular receptor 2	Homo sapiens	Inhibition	<	50.0	%	PMID[537434]
NPT2	Others	Unspecified		Potency	n.a.	12572.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1120.5	nM	PubChem BioAssay data set

☑ 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 NPC253423 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	234
0.1-0.2	1644
0.2-0.3	4002
0.3-0.4	11443
0.4-0.5	11531
0.5-0.6	10289
0.6-0.7	2997
0.7-0.8	488
0.8-0.85	46
0.85-0.9	15
0.9-0.95	4
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9783	High Similarity	NPC217621
0.967	High Similarity	NPC61944
0.9574	High Similarity	NPC304873
0.9574	High Similarity	NPC25458
0.9333	High Similarity	NPC62765
0.9278	High Similarity	NPC105899
0.9255	High Similarity	NPC229242
0.9091	High Similarity	NPC249811
0.8958	High Similarity	NPC203925
0.8889	High Similarity	NPC318107
0.8878	High Similarity	NPC255676
0.8866	High Similarity	NPC70624
0.8812	High Similarity	NPC318327
0.8776	High Similarity	NPC188895
0.8776	High Similarity	NPC284477
0.8763	High Similarity	NPC228435
0.8738	High Similarity	NPC66208
0.8737	High Similarity	NPC130398
0.8673	High Similarity	NPC282895
0.8632	High Similarity	NPC261181
0.8557	High Similarity	NPC92754
0.8557	High Similarity	NPC249912
0.8557	High Similarity	NPC276775
0.8491	Intermediate Similarity	NPC186933
0.8469	Intermediate Similarity	NPC35448
0.8469	Intermediate Similarity	NPC78701
0.8469	Intermediate Similarity	NPC225060
0.8447	Intermediate Similarity	NPC85493
0.8421	Intermediate Similarity	NPC110704
0.8384	Intermediate Similarity	NPC325497
0.8384	Intermediate Similarity	NPC146351
0.8352	Intermediate Similarity	NPC285773
0.8318	Intermediate Similarity	NPC476357
0.8317	Intermediate Similarity	NPC291426
0.8316	Intermediate Similarity	NPC274455
0.8316	Intermediate Similarity	NPC70940
0.8316	Intermediate Similarity	NPC86670
0.8298	Intermediate Similarity	NPC329064
0.8286	Intermediate Similarity	NPC476003
0.8286	Intermediate Similarity	NPC474057
0.8286	Intermediate Similarity	NPC260818
0.8257	Intermediate Similarity	NPC160199
0.8252	Intermediate Similarity	NPC187913
0.8235	Intermediate Similarity	NPC324786
0.8208	Intermediate Similarity	NPC321852
0.82	Intermediate Similarity	NPC118343
0.8191	Intermediate Similarity	NPC322387
0.8173	Intermediate Similarity	NPC34715
0.8165	Intermediate Similarity	NPC158157
0.8148	Intermediate Similarity	NPC81808
0.8137	Intermediate Similarity	NPC301943
0.8137	Intermediate Similarity	NPC474365
0.8137	Intermediate Similarity	NPC329556
0.8119	Intermediate Similarity	NPC42211
0.8108	Intermediate Similarity	NPC472708
0.81	Intermediate Similarity	NPC175852
0.81	Intermediate Similarity	NPC210529
0.81	Intermediate Similarity	NPC160548
0.8077	Intermediate Similarity	NPC184658
0.8058	Intermediate Similarity	NPC249067
0.8058	Intermediate Similarity	NPC31786
0.8056	Intermediate Similarity	NPC211421
0.8056	Intermediate Similarity	NPC153053
0.8037	Intermediate Similarity	NPC158282
0.8022	Intermediate Similarity	NPC127343
0.8	Intermediate Similarity	NPC211439
0.8	Intermediate Similarity	NPC29883
0.8	Intermediate Similarity	NPC50192
0.8	Intermediate Similarity	NPC226699
0.7981	Intermediate Similarity	NPC209632
0.7965	Intermediate Similarity	NPC165197
0.7963	Intermediate Similarity	NPC272524
0.7961	Intermediate Similarity	NPC160382
0.7957	Intermediate Similarity	NPC288903
0.7941	Intermediate Similarity	NPC52472
0.7928	Intermediate Similarity	NPC240664
0.7925	Intermediate Similarity	NPC100551
0.7925	Intermediate Similarity	NPC224584
0.7909	Intermediate Similarity	NPC161304
0.7905	Intermediate Similarity	NPC37914
0.7905	Intermediate Similarity	NPC37622
0.7905	Intermediate Similarity	NPC30594
0.7905	Intermediate Similarity	NPC6984
0.7905	Intermediate Similarity	NPC119271
0.7895	Intermediate Similarity	NPC269923
0.7895	Intermediate Similarity	NPC167323
0.7895	Intermediate Similarity	NPC25168
0.789	Intermediate Similarity	NPC474363
0.789	Intermediate Similarity	NPC196673
0.7885	Intermediate Similarity	NPC114594
0.7872	Intermediate Similarity	NPC44546
0.787	Intermediate Similarity	NPC474314
0.7864	Intermediate Similarity	NPC45613
0.785	Intermediate Similarity	NPC95172
0.785	Intermediate Similarity	NPC216122
0.7843	Intermediate Similarity	NPC245561
0.7838	Intermediate Similarity	NPC128825
0.7838	Intermediate Similarity	NPC131192
0.7835	Intermediate Similarity	NPC173443
0.783	Intermediate Similarity	NPC56493
0.783	Intermediate Similarity	NPC141523
0.7826	Intermediate Similarity	NPC297193
0.7818	Intermediate Similarity	NPC274839
0.7818	Intermediate Similarity	NPC306740
0.781	Intermediate Similarity	NPC269457
0.7798	Intermediate Similarity	NPC128368
0.7789	Intermediate Similarity	NPC294134
0.7789	Intermediate Similarity	NPC95965
0.7788	Intermediate Similarity	NPC89886
0.7788	Intermediate Similarity	NPC60679
0.7788	Intermediate Similarity	NPC13426
0.7778	Intermediate Similarity	NPC475002
0.7778	Intermediate Similarity	NPC95126
0.7768	Intermediate Similarity	NPC125252
0.7767	Intermediate Similarity	NPC473325
0.7766	Intermediate Similarity	NPC44830
0.7759	Intermediate Similarity	NPC85511
0.7757	Intermediate Similarity	NPC269023
0.7757	Intermediate Similarity	NPC265407
0.7757	Intermediate Similarity	NPC83628
0.7757	Intermediate Similarity	NPC99846
0.7757	Intermediate Similarity	NPC474364
0.7757	Intermediate Similarity	NPC469636
0.7757	Intermediate Similarity	NPC10251
0.7757	Intermediate Similarity	NPC17417
0.7736	Intermediate Similarity	NPC317592
0.7727	Intermediate Similarity	NPC237366
0.7723	Intermediate Similarity	NPC246679
0.7723	Intermediate Similarity	NPC257182
0.7714	Intermediate Similarity	NPC329282
0.7708	Intermediate Similarity	NPC474211
0.7699	Intermediate Similarity	NPC161943
0.7699	Intermediate Similarity	NPC273282
0.7699	Intermediate Similarity	NPC27633
0.7699	Intermediate Similarity	NPC94298
0.7699	Intermediate Similarity	NPC41567
0.7699	Intermediate Similarity	NPC94637
0.7699	Intermediate Similarity	NPC474890
0.7692	Intermediate Similarity	NPC244427
0.7692	Intermediate Similarity	NPC222390
0.7692	Intermediate Similarity	NPC117794
0.7685	Intermediate Similarity	NPC196246
0.7685	Intermediate Similarity	NPC174099
0.7685	Intermediate Similarity	NPC214067
0.7685	Intermediate Similarity	NPC93084
0.7685	Intermediate Similarity	NPC251854
0.7684	Intermediate Similarity	NPC168855
0.7679	Intermediate Similarity	NPC83718
0.7672	Intermediate Similarity	NPC472703
0.767	Intermediate Similarity	NPC280869
0.7667	Intermediate Similarity	NPC32203
0.7667	Intermediate Similarity	NPC206800
0.7658	Intermediate Similarity	NPC474685
0.7647	Intermediate Similarity	NPC289201
0.7642	Intermediate Similarity	NPC172483
0.7642	Intermediate Similarity	NPC13495
0.7642	Intermediate Similarity	NPC163734
0.7636	Intermediate Similarity	NPC231717
0.7636	Intermediate Similarity	NPC17693
0.7632	Intermediate Similarity	NPC61779
0.7632	Intermediate Similarity	NPC90522
0.7632	Intermediate Similarity	NPC328459
0.7629	Intermediate Similarity	NPC89377
0.7629	Intermediate Similarity	NPC194326
0.7627	Intermediate Similarity	NPC287473
0.7627	Intermediate Similarity	NPC472592
0.7624	Intermediate Similarity	NPC32977
0.7624	Intermediate Similarity	NPC172925
0.7624	Intermediate Similarity	NPC81010
0.7619	Intermediate Similarity	NPC274443
0.7619	Intermediate Similarity	NPC247976
0.7615	Intermediate Similarity	NPC210089
0.7615	Intermediate Similarity	NPC474157
0.7615	Intermediate Similarity	NPC305912
0.7615	Intermediate Similarity	NPC1082
0.7607	Intermediate Similarity	NPC472704
0.7607	Intermediate Similarity	NPC275145
0.7604	Intermediate Similarity	NPC474354
0.7596	Intermediate Similarity	NPC469481
0.7593	Intermediate Similarity	NPC17525
0.7589	Intermediate Similarity	NPC240163
0.7573	Intermediate Similarity	NPC260000
0.7568	Intermediate Similarity	NPC471721
0.7568	Intermediate Similarity	NPC11824
0.7568	Intermediate Similarity	NPC242136
0.7568	Intermediate Similarity	NPC307651
0.7568	Intermediate Similarity	NPC98543
0.7565	Intermediate Similarity	NPC72977
0.7553	Intermediate Similarity	NPC145053
0.7553	Intermediate Similarity	NPC100039
0.7547	Intermediate Similarity	NPC472222
0.7547	Intermediate Similarity	NPC472221
0.7545	Intermediate Similarity	NPC212718
0.7545	Intermediate Similarity	NPC114682
0.7545	Intermediate Similarity	NPC82899
0.7545	Intermediate Similarity	NPC270699
0.7545	Intermediate Similarity	NPC228609
0.7542	Intermediate Similarity	NPC236189
0.7527	Intermediate Similarity	NPC300205
0.7526	Intermediate Similarity	NPC93843

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 NPC253423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	242
0.1-0.2	927
0.2-0.3	1440
0.3-0.4	2872
0.4-0.5	2317
0.5-0.6	996
0.6-0.7	275
0.7-0.8	57
0.8-0.85	17
0.85-0.9	5
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9333	High Similarity	NPD9258	Approved
0.9333	High Similarity	NPD9256	Approved
0.8889	High Similarity	NPD9259	Approved
0.8889	High Similarity	NPD9257	Approved
0.8632	High Similarity	NPD1202	Approved
0.8558	High Similarity	NPD9508	Approved
0.8491	Intermediate Similarity	NPD5951	Approved
0.8447	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8404	Intermediate Similarity	NPD800	Approved
0.8352	Intermediate Similarity	NPD9491	Approved
0.8316	Intermediate Similarity	NPD1090	Approved
0.8316	Intermediate Similarity	NPD1089	Approved
0.8316	Intermediate Similarity	NPD1086	Approved
0.82	Intermediate Similarity	NPD1238	Approved
0.82	Intermediate Similarity	NPD2066	Phase 3
0.8163	Intermediate Similarity	NPD9260	Approved
0.8144	Intermediate Similarity	NPD1088	Approved
0.8137	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD1929	Approved
0.8137	Intermediate Similarity	NPD1930	Approved
0.8132	Intermediate Similarity	NPD226	Approved
0.8131	Intermediate Similarity	NPD5277	Phase 2
0.81	Intermediate Similarity	NPD9495	Approved
0.8058	Intermediate Similarity	NPD1237	Approved
0.8058	Intermediate Similarity	NPD164	Approved
0.8041	Intermediate Similarity	NPD1239	Approved
0.8039	Intermediate Similarity	NPD1932	Approved
0.8036	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9267	Approved
0.8	Intermediate Similarity	NPD9263	Approved
0.8	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9264	Approved
0.8	Intermediate Similarity	NPD1087	Approved
0.798	Intermediate Similarity	NPD1693	Approved
0.7925	Intermediate Similarity	NPD74	Approved
0.7925	Intermediate Similarity	NPD9266	Approved
0.7912	Intermediate Similarity	NPD9490	Approved
0.7838	Intermediate Similarity	NPD9493	Approved
0.7822	Intermediate Similarity	NPD1565	Approved
0.7822	Intermediate Similarity	NPD1564	Approved
0.7822	Intermediate Similarity	NPD1566	Phase 3
0.7802	Intermediate Similarity	NPD227	Approved
0.7802	Intermediate Similarity	NPD225	Approved
0.7759	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7757	Intermediate Similarity	NPD2329	Discontinued
0.7757	Intermediate Similarity	NPD2182	Approved
0.7699	Intermediate Similarity	NPD9545	Approved
0.7685	Intermediate Similarity	NPD1317	Discontinued
0.7667	Intermediate Similarity	NPD9716	Approved
0.7624	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7619	Intermediate Similarity	NPD9261	Approved
0.7615	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD1104	Approved
0.7542	Intermediate Similarity	NPD1888	Phase 1
0.7525	Intermediate Similarity	NPD1563	Approved
0.7525	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD9281	Approved
0.7475	Intermediate Similarity	NPD5346	Phase 2
0.7475	Intermediate Similarity	NPD5347	Phase 2
0.7449	Intermediate Similarity	NPD4793	Discontinued
0.7379	Intermediate Similarity	NPD1989	Approved
0.7377	Intermediate Similarity	NPD6966	Discovery
0.7377	Intermediate Similarity	NPD7008	Discontinued
0.7377	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD9717	Approved
0.7345	Intermediate Similarity	NPD2629	Approved
0.7312	Intermediate Similarity	NPD9294	Approved
0.729	Intermediate Similarity	NPD6647	Phase 2
0.7288	Intermediate Similarity	NPD6287	Discontinued
0.7232	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5909	Discontinued
0.7217	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1889	Phase 1
0.7193	Intermediate Similarity	NPD1246	Approved
0.719	Intermediate Similarity	NPD1164	Approved
0.7179	Intermediate Similarity	NPD1245	Approved
0.7177	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD9272	Approved
0.71	Intermediate Similarity	NPD650	Approved
0.7087	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD1203	Approved
0.7041	Intermediate Similarity	NPD3971	Phase 1
0.7034	Intermediate Similarity	NPD9268	Approved
0.7034	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD942	Approved
0.7009	Intermediate Similarity	NPD9712	Approved
0.7	Intermediate Similarity	NPD1201	Approved
0.6992	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD256	Approved
0.6983	Remote Similarity	NPD255	Approved
0.6977	Remote Similarity	NPD4308	Phase 3
0.6975	Remote Similarity	NPD2345	Approved
0.6942	Remote Similarity	NPD4878	Approved
0.6942	Remote Similarity	NPD9269	Phase 2
0.6917	Remote Similarity	NPD9693	Approved
0.6917	Remote Similarity	NPD9692	Approved
0.6916	Remote Similarity	NPD9711	Approved
0.6916	Remote Similarity	NPD9710	Approved
0.6911	Remote Similarity	NPD1470	Approved
0.6905	Remote Similarity	NPD3764	Approved
0.69	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD3673	Approved
0.6893	Remote Similarity	NPD3672	Approved
0.6891	Remote Similarity	NPD4102	Approved
0.6891	Remote Similarity	NPD4105	Approved
0.6887	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD844	Approved
0.6885	Remote Similarity	NPD5159	Phase 2
0.6885	Remote Similarity	NPD5157	Phase 1
0.6885	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD447	Suspended
0.686	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5306	Approved
0.6833	Remote Similarity	NPD5305	Approved
0.6829	Remote Similarity	NPD1283	Approved
0.6827	Remote Similarity	NPD7609	Phase 3
0.6822	Remote Similarity	NPD9566	Approved
0.6822	Remote Similarity	NPD288	Approved
0.6818	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.681	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD689	Discontinued
0.6794	Remote Similarity	NPD5404	Approved
0.6794	Remote Similarity	NPD1551	Phase 2
0.6794	Remote Similarity	NPD5406	Approved
0.6794	Remote Similarity	NPD5405	Approved
0.6794	Remote Similarity	NPD5408	Approved
0.678	Remote Similarity	NPD9568	Approved
0.6777	Remote Similarity	NPD4135	Approved
0.6777	Remote Similarity	NPD4106	Approved
0.6777	Remote Similarity	NPD4136	Approved
0.6772	Remote Similarity	NPD2313	Discontinued
0.6765	Remote Similarity	NPD506	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD7631	Approved
0.6759	Remote Similarity	NPD253	Approved
0.6754	Remote Similarity	NPD2067	Discontinued
0.6744	Remote Similarity	NPD230	Phase 1
0.6742	Remote Similarity	NPD2346	Discontinued
0.6733	Remote Similarity	NPD111	Approved
0.6723	Remote Similarity	NPD1758	Phase 1
0.6723	Remote Similarity	NPD7610	Discontinued
0.6721	Remote Similarity	NPD4806	Approved
0.6721	Remote Similarity	NPD4807	Approved
0.672	Remote Similarity	NPD2798	Approved
0.6719	Remote Similarity	NPD520	Approved
0.6716	Remote Similarity	NPD7003	Approved
0.6716	Remote Similarity	NPD4628	Phase 3
0.6698	Remote Similarity	NPD1066	Discontinued
0.6697	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD5048	Discontinued
0.6695	Remote Similarity	NPD4198	Discontinued
0.6694	Remote Similarity	NPD2198	Approved
0.6694	Remote Similarity	NPD2199	Approved
0.6694	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1778	Approved
0.6667	Remote Similarity	NPD1759	Phase 1
0.6667	Remote Similarity	NPD1608	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD2935	Discontinued
0.6667	Remote Similarity	NPD7009	Phase 2
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD1241	Discontinued
0.6667	Remote Similarity	NPD9494	Approved
0.6667	Remote Similarity	NPD3495	Discontinued
0.664	Remote Similarity	NPD553	Approved
0.664	Remote Similarity	NPD9567	Approved
0.664	Remote Similarity	NPD2797	Approved
0.664	Remote Similarity	NPD552	Approved
0.6636	Remote Similarity	NPD6049	Phase 2
0.6636	Remote Similarity	NPD2934	Approved
0.6636	Remote Similarity	NPD2933	Approved
0.6636	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD1616	Discontinued
0.6636	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.6617	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD159	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD1282	Approved
0.6591	Remote Similarity	NPD2799	Discontinued
0.6589	Remote Similarity	NPD7715	Approved
0.6589	Remote Similarity	NPD7714	Approved
0.6587	Remote Similarity	NPD4980	Approved
0.6587	Remote Similarity	NPD1019	Discontinued
0.6585	Remote Similarity	NPD1281	Approved
0.6581	Remote Similarity	NPD181	Approved
0.6574	Remote Similarity	NPD2859	Approved
0.6574	Remote Similarity	NPD2860	Approved
0.6566	Remote Similarity	NPD1507	Clinical (unspecified phase)
0.6565	Remote Similarity	NPD1607	Approved
0.6565	Remote Similarity	NPD6817	Clinical (unspecified phase)
0.656	Remote Similarity	NPD1574	Approved
0.6557	Remote Similarity	NPD3019	Approved
0.6557	Remote Similarity	NPD2932	Approved
0.6557	Remote Similarity	NPD4626	Approved
0.6552	Remote Similarity	NPD3642	Approved
0.6552	Remote Similarity	NPD3643	Approved
0.6552	Remote Similarity	NPD3644	Approved
0.6545	Remote Similarity	NPD3020	Approved
0.6542	Remote Similarity	NPD845	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