NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	180.04
Volume:	177.642
LogP:	1.387
LogD:	5.139
LogS:	-1.266
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.694
Synthetic Accessibility Score:	1.444
Fsp3:	0.111
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:	-5.094
MDCK Permeability:	1.76369594555581e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.782

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.771
Plasma Protein Binding (PPB):	42.42423629760742%
Volume Distribution (VD):	0.186
Pgp-substrate:	31.260704040527344%

ADMET: Metabolism

CYP1A2-inhibitor:	0.14
CYP1A2-substrate:	0.211
CYP2C19-inhibitor:	0.057
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.125
CYP2C9-substrate:	0.227
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.112
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	6.43
Half-life (T1/2):	0.857

ADMET: Toxicity

hERG Blockers:	0.084
Human Hepatotoxicity (H-HT):	0.256
Drug-inuced Liver Injury (DILI):	0.853
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.198
Carcinogencity:	0.014
Eye Corrosion:	0.024
Eye Irritation:	0.99
Respiratory Toxicity:	0.173

Download Data

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

Natural Product: NPC85493

Natural Product ID:	NPC85493
*Common Name:**	2-Methoxycarbonylbenzoic Acid
IUPAC Name:	2-methoxycarbonylbenzoic acid
Synonyms:
Standard InCHIKey:	FNJSWIPFHMKRAT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C9H8O4/c1-13-9(12)7-5-3-2-4-6(7)8(10)11/h2-5H,1H3,(H,10,11)
SMILES:	COC(=O)c1ccccc1C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL243609
PubChem CID:	20392
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic acid esters

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference

☑ 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
Potency	5

Activity Type	# Activity
Individual Protein	1
Others	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT540	Individual Protein	Bile acid receptor FXR	Homo sapiens	Potency	n.a.	50.1	nM	PMID[470702]
NPT2	Others	Unspecified		Potency	n.a.	2187.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	77.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21872.4	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 NPC85493 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	232
0.1-0.2	1333
0.2-0.3	3589
0.3-0.4	9072
0.4-0.5	11118
0.5-0.6	11167
0.6-0.7	5463
0.7-0.8	633
0.8-0.85	55
0.85-0.9	16
0.9-0.95	15
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9804	High Similarity	NPC260818
0.9709	High Similarity	NPC321852
0.96	High Similarity	NPC31786
0.9524	High Similarity	NPC153053
0.9412	High Similarity	NPC119271
0.932	High Similarity	NPC56493
0.93	High Similarity	NPC282895
0.9231	High Similarity	NPC10251
0.9231	High Similarity	NPC17417
0.9143	High Similarity	NPC174099
0.9143	High Similarity	NPC93084
0.9143	High Similarity	NPC196246
0.9143	High Similarity	NPC214067
0.9143	High Similarity	NPC251854
0.91	High Similarity	NPC229242
0.9057	High Similarity	NPC305912
0.9057	High Similarity	NPC1082
0.8972	High Similarity	NPC270699
0.8972	High Similarity	NPC82899
0.8835	High Similarity	NPC284477
0.8835	High Similarity	NPC45613
0.8807	High Similarity	NPC237366
0.88	High Similarity	NPC130398
0.875	High Similarity	NPC89886
0.8716	High Similarity	NPC272524
0.8692	High Similarity	NPC265407
0.8692	High Similarity	NPC83628
0.8679	High Similarity	NPC37622
0.8679	High Similarity	NPC30594
0.8641	High Similarity	NPC203925
0.8636	High Similarity	NPC307651
0.8627	High Similarity	NPC92754
0.8627	High Similarity	NPC249912
0.8627	High Similarity	NPC276775
0.8585	High Similarity	NPC209632
0.8571	High Similarity	NPC60679
0.8571	High Similarity	NPC255676
0.8559	High Similarity	NPC306740
0.8544	High Similarity	NPC225060
0.8544	High Similarity	NPC78701
0.8544	High Similarity	NPC35448
0.8491	Intermediate Similarity	NPC114594
0.8476	Intermediate Similarity	NPC304873
0.8462	Intermediate Similarity	NPC146351
0.8462	Intermediate Similarity	NPC217621
0.8447	Intermediate Similarity	NPC253423
0.84	Intermediate Similarity	NPC62765
0.8396	Intermediate Similarity	NPC301943
0.8396	Intermediate Similarity	NPC474365
0.8393	Intermediate Similarity	NPC81808
0.8393	Intermediate Similarity	NPC474685
0.8381	Intermediate Similarity	NPC42211
0.8381	Intermediate Similarity	NPC70624
0.8364	Intermediate Similarity	NPC476003
0.8364	Intermediate Similarity	NPC474157
0.8364	Intermediate Similarity	NPC210089
0.835	Intermediate Similarity	NPC61944
0.8349	Intermediate Similarity	NPC269023
0.8349	Intermediate Similarity	NPC99846
0.8319	Intermediate Similarity	NPC149691
0.8304	Intermediate Similarity	NPC474363
0.8302	Intermediate Similarity	NPC188895
0.8302	Intermediate Similarity	NPC25458
0.8288	Intermediate Similarity	NPC158282
0.8286	Intermediate Similarity	NPC325497
0.8286	Intermediate Similarity	NPC118343
0.8241	Intermediate Similarity	NPC105899
0.8235	Intermediate Similarity	NPC246166
0.823	Intermediate Similarity	NPC210092
0.822	Intermediate Similarity	NPC223351
0.822	Intermediate Similarity	NPC46634
0.8198	Intermediate Similarity	NPC167504
0.8182	Intermediate Similarity	NPC318327
0.8182	Intermediate Similarity	NPC469636
0.8174	Intermediate Similarity	NPC240664
0.8142	Intermediate Similarity	NPC308744
0.8125	Intermediate Similarity	NPC66208
0.8125	Intermediate Similarity	NPC79496
0.8125	Intermediate Similarity	NPC474314
0.8113	Intermediate Similarity	NPC228435
0.8099	Intermediate Similarity	NPC169913
0.8091	Intermediate Similarity	NPC249811
0.8091	Intermediate Similarity	NPC211439
0.8083	Intermediate Similarity	NPC295664
0.8073	Intermediate Similarity	NPC269457
0.8034	Intermediate Similarity	NPC204784
0.8018	Intermediate Similarity	NPC474364
0.8017	Intermediate Similarity	NPC275576
0.8	Intermediate Similarity	NPC228739
0.8	Intermediate Similarity	NPC318107
0.7981	Intermediate Similarity	NPC261181
0.7941	Intermediate Similarity	NPC173443
0.7931	Intermediate Similarity	NPC131192
0.7931	Intermediate Similarity	NPC128825
0.7931	Intermediate Similarity	NPC158157
0.7913	Intermediate Similarity	NPC186933
0.7895	Intermediate Similarity	NPC161611
0.7895	Intermediate Similarity	NPC128368
0.7886	Intermediate Similarity	NPC51448
0.7886	Intermediate Similarity	NPC115797
0.7876	Intermediate Similarity	NPC243355
0.7876	Intermediate Similarity	NPC474057
0.7851	Intermediate Similarity	NPC471466
0.7845	Intermediate Similarity	NPC100353
0.7826	Intermediate Similarity	NPC477411
0.7826	Intermediate Similarity	NPC196075
0.7818	Intermediate Similarity	NPC329282
0.7807	Intermediate Similarity	NPC212415
0.78	Intermediate Similarity	NPC44546
0.7797	Intermediate Similarity	NPC27633
0.7797	Intermediate Similarity	NPC94637
0.7797	Intermediate Similarity	NPC94298
0.7788	Intermediate Similarity	NPC110704
0.7769	Intermediate Similarity	NPC217756
0.7769	Intermediate Similarity	NPC472703
0.7768	Intermediate Similarity	NPC470391
0.7759	Intermediate Similarity	NPC476357
0.7745	Intermediate Similarity	NPC89377
0.7745	Intermediate Similarity	NPC322387
0.7739	Intermediate Similarity	NPC474176
0.7739	Intermediate Similarity	NPC17693
0.7739	Intermediate Similarity	NPC13784
0.7731	Intermediate Similarity	NPC61779
0.7731	Intermediate Similarity	NPC90522
0.7731	Intermediate Similarity	NPC328459
0.7727	Intermediate Similarity	NPC160382
0.7705	Intermediate Similarity	NPC472704
0.7705	Intermediate Similarity	NPC85511
0.77	Intermediate Similarity	NPC288903
0.77	Intermediate Similarity	NPC285773
0.7699	Intermediate Similarity	NPC281604
0.7692	Intermediate Similarity	NPC226093
0.7685	Intermediate Similarity	NPC175852
0.7685	Intermediate Similarity	NPC210529
0.7685	Intermediate Similarity	NPC160548
0.7679	Intermediate Similarity	NPC187913
0.7672	Intermediate Similarity	NPC196673
0.7667	Intermediate Similarity	NPC72977
0.7667	Intermediate Similarity	NPC473243
0.7661	Intermediate Similarity	NPC475236
0.7658	Intermediate Similarity	NPC249067
0.7642	Intermediate Similarity	NPC265910
0.7642	Intermediate Similarity	NPC145134
0.7642	Intermediate Similarity	NPC91475
0.7638	Intermediate Similarity	NPC7012
0.7636	Intermediate Similarity	NPC222390
0.7636	Intermediate Similarity	NPC244427
0.7636	Intermediate Similarity	NPC320891
0.7632	Intermediate Similarity	NPC234639
0.7623	Intermediate Similarity	NPC67300
0.7619	Intermediate Similarity	NPC272946
0.7611	Intermediate Similarity	NPC156648
0.7611	Intermediate Similarity	NPC34715
0.7607	Intermediate Similarity	NPC228936
0.7607	Intermediate Similarity	NPC221275
0.7603	Intermediate Similarity	NPC165197
0.7603	Intermediate Similarity	NPC50872
0.76	Intermediate Similarity	NPC71525
0.76	Intermediate Similarity	NPC158654
0.7597	Intermediate Similarity	NPC477893
0.7597	Intermediate Similarity	NPC477896
0.7596	Intermediate Similarity	NPC220893
0.7593	Intermediate Similarity	NPC156021
0.7593	Intermediate Similarity	NPC270654
0.7583	Intermediate Similarity	NPC472708
0.7581	Intermediate Similarity	NPC470765
0.7581	Intermediate Similarity	NPC121272
0.7568	Intermediate Similarity	NPC13426
0.7568	Intermediate Similarity	NPC274443
0.7568	Intermediate Similarity	NPC91820
0.7568	Intermediate Similarity	NPC329556
0.7568	Intermediate Similarity	NPC82426
0.7568	Intermediate Similarity	NPC291426
0.7563	Intermediate Similarity	NPC160199
0.7563	Intermediate Similarity	NPC228318
0.7563	Intermediate Similarity	NPC125252
0.7549	Intermediate Similarity	NPC58616
0.7549	Intermediate Similarity	NPC294134
0.7545	Intermediate Similarity	NPC473325
0.7545	Intermediate Similarity	NPC112552
0.7542	Intermediate Similarity	NPC135730
0.7541	Intermediate Similarity	NPC167323
0.7541	Intermediate Similarity	NPC25168
0.7541	Intermediate Similarity	NPC269923
0.754	Intermediate Similarity	NPC473744
0.7524	Intermediate Similarity	NPC274455
0.7524	Intermediate Similarity	NPC86670
0.7524	Intermediate Similarity	NPC70940
0.7522	Intermediate Similarity	NPC475203
0.7522	Intermediate Similarity	NPC472315
0.7522	Intermediate Similarity	NPC136962
0.7522	Intermediate Similarity	NPC474376
0.7522	Intermediate Similarity	NPC472316
0.7522	Intermediate Similarity	NPC37115
0.7521	Intermediate Similarity	NPC233282
0.7521	Intermediate Similarity	NPC87069
0.7521	Intermediate Similarity	NPC109241
0.752	Intermediate Similarity	NPC472706
0.752	Intermediate Similarity	NPC473220
0.752	Intermediate Similarity	NPC51037

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 NPC85493 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	885
0.2-0.3	1383
0.3-0.4	2719
0.4-0.5	2360
0.5-0.6	1179
0.6-0.7	329
0.7-0.8	60
0.8-0.85	6
0.85-0.9	0
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.96	High Similarity	NPD164	Approved
0.9231	High Similarity	NPD2182	Approved
0.8532	High Similarity	NPD2181	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD9258	Approved
0.84	Intermediate Similarity	NPD9256	Approved
0.8286	Intermediate Similarity	NPD1238	Approved
0.8182	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9259	Approved
0.8	Intermediate Similarity	NPD9257	Approved
0.7981	Intermediate Similarity	NPD1202	Approved
0.7931	Intermediate Similarity	NPD9493	Approved
0.7913	Intermediate Similarity	NPD5951	Approved
0.7913	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7797	Intermediate Similarity	NPD9545	Approved
0.776	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.77	Intermediate Similarity	NPD9491	Approved
0.7685	Intermediate Similarity	NPD9495	Approved
0.7658	Intermediate Similarity	NPD1237	Approved
0.7619	Intermediate Similarity	NPD7008	Discontinued
0.7568	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD1930	Approved
0.7568	Intermediate Similarity	NPD1929	Approved
0.7559	Intermediate Similarity	NPD3764	Approved
0.7524	Intermediate Similarity	NPD1089	Approved
0.7524	Intermediate Similarity	NPD1086	Approved
0.7524	Intermediate Similarity	NPD1090	Approved
0.7521	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD9717	Approved
0.7477	Intermediate Similarity	NPD1932	Approved
0.7455	Intermediate Similarity	NPD2066	Phase 3
0.7436	Intermediate Similarity	NPD5277	Phase 2
0.7429	Intermediate Similarity	NPD800	Approved
0.7419	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD6647	Phase 2
0.7407	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD9260	Approved
0.7383	Intermediate Similarity	NPD1088	Approved
0.735	Intermediate Similarity	NPD9508	Approved
0.7345	Intermediate Similarity	NPD5909	Discontinued
0.7333	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD2067	Discontinued
0.7327	Intermediate Similarity	NPD226	Approved
0.7315	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7304	Intermediate Similarity	NPD9263	Approved
0.7304	Intermediate Similarity	NPD9267	Approved
0.7304	Intermediate Similarity	NPD9264	Approved
0.7304	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD9490	Approved
0.729	Intermediate Similarity	NPD1239	Approved
0.7258	Intermediate Similarity	NPD6287	Discontinued
0.7248	Intermediate Similarity	NPD1693	Approved
0.7244	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD2329	Discontinued
0.7241	Intermediate Similarity	NPD9266	Approved
0.7241	Intermediate Similarity	NPD74	Approved
0.7239	Intermediate Similarity	NPD2346	Discontinued
0.7238	Intermediate Similarity	NPD1087	Approved
0.7179	Intermediate Similarity	NPD1317	Discontinued
0.7165	Intermediate Similarity	NPD1203	Approved
0.7154	Intermediate Similarity	NPD2313	Discontinued
0.7121	Intermediate Similarity	NPD230	Phase 1
0.7121	Intermediate Similarity	NPD447	Suspended
0.7117	Intermediate Similarity	NPD1566	Phase 3
0.7117	Intermediate Similarity	NPD1564	Approved
0.7117	Intermediate Similarity	NPD1565	Approved
0.7111	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD1104	Approved
0.7087	Intermediate Similarity	NPD1876	Approved
0.7087	Intermediate Similarity	NPD1283	Approved
0.7075	Intermediate Similarity	NPD650	Approved
0.7037	Intermediate Similarity	NPD2935	Discontinued
0.7031	Intermediate Similarity	NPD1470	Approved
0.703	Intermediate Similarity	NPD225	Approved
0.703	Intermediate Similarity	NPD227	Approved
0.7027	Intermediate Similarity	NPD1989	Approved
0.7025	Intermediate Similarity	NPD9281	Approved
0.7025	Intermediate Similarity	NPD2629	Approved
0.7019	Intermediate Similarity	NPD3971	Phase 1
0.6977	Remote Similarity	NPD6085	Phase 2
0.6977	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD1019	Discontinued
0.6975	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD2799	Discontinued
0.696	Remote Similarity	NPD1362	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9261	Approved
0.6957	Remote Similarity	NPD7003	Approved
0.6957	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD5347	Phase 2
0.6944	Remote Similarity	NPD5346	Phase 2
0.6942	Remote Similarity	NPD1241	Discontinued
0.694	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD4878	Approved
0.6929	Remote Similarity	NPD1481	Phase 2
0.6923	Remote Similarity	NPD3226	Approved
0.6917	Remote Similarity	NPD969	Suspended
0.6916	Remote Similarity	NPD4793	Discontinued
0.69	Remote Similarity	NPD9716	Approved
0.6899	Remote Similarity	NPD2797	Approved
0.6894	Remote Similarity	NPD411	Approved
0.6881	Remote Similarity	NPD3673	Approved
0.6881	Remote Similarity	NPD3672	Approved
0.687	Remote Similarity	NPD6832	Phase 2
0.6861	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7236	Approved
0.685	Remote Similarity	NPD1281	Approved
0.685	Remote Similarity	NPD1535	Discovery
0.6847	Remote Similarity	NPD1563	Approved
0.6846	Remote Similarity	NPD2798	Approved
0.6838	Remote Similarity	NPD4308	Phase 3
0.6835	Remote Similarity	NPD3750	Approved
0.6835	Remote Similarity	NPD4628	Phase 3
0.6829	Remote Similarity	NPD4198	Discontinued
0.6825	Remote Similarity	NPD5305	Approved
0.6825	Remote Similarity	NPD4626	Approved
0.6825	Remote Similarity	NPD5306	Approved
0.6822	Remote Similarity	NPD2198	Approved
0.6822	Remote Similarity	NPD2199	Approved
0.6818	Remote Similarity	NPD7609	Phase 3
0.6806	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.68	Remote Similarity	NPD1894	Discontinued
0.6797	Remote Similarity	NPD3972	Approved
0.6797	Remote Similarity	NPD1608	Approved
0.6794	Remote Similarity	NPD9494	Approved
0.6789	Remote Similarity	NPD689	Discontinued
0.6774	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD4136	Approved
0.6772	Remote Similarity	NPD4106	Approved
0.6772	Remote Similarity	NPD4135	Approved
0.6769	Remote Similarity	NPD1164	Approved
0.6769	Remote Similarity	NPD552	Approved
0.6769	Remote Similarity	NPD553	Approved
0.6769	Remote Similarity	NPD9567	Approved
0.6767	Remote Similarity	NPD3268	Approved
0.6765	Remote Similarity	NPD9294	Approved
0.6763	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7631	Approved
0.6748	Remote Similarity	NPD1246	Approved
0.6746	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD9268	Approved
0.6746	Remote Similarity	NPD4105	Approved
0.6746	Remote Similarity	NPD4102	Approved
0.6723	Remote Similarity	NPD1358	Approved
0.672	Remote Similarity	NPD2347	Approved
0.6719	Remote Similarity	NPD4807	Approved
0.6719	Remote Similarity	NPD4806	Approved
0.6719	Remote Similarity	NPD1201	Approved
0.6695	Remote Similarity	NPD5048	Discontinued
0.6692	Remote Similarity	NPD1888	Phase 1
0.6667	Remote Similarity	NPD1877	Discontinued
0.6667	Remote Similarity	NPD1240	Approved
0.6667	Remote Similarity	NPD9269	Phase 2
0.6667	Remote Similarity	NPD1551	Phase 2
0.6643	Remote Similarity	NPD2534	Approved
0.6643	Remote Similarity	NPD2532	Approved
0.6643	Remote Similarity	NPD2533	Approved
0.6641	Remote Similarity	NPD3496	Discontinued
0.6641	Remote Similarity	NPD3847	Discontinued
0.6639	Remote Similarity	NPD3134	Approved
0.6621	Remote Similarity	NPD7239	Suspended
0.662	Remote Similarity	NPD7440	Discontinued
0.6619	Remote Similarity	NPD2344	Approved
0.6618	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5157	Phase 1
0.6615	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6615	Remote Similarity	NPD5159	Phase 2
0.6614	Remote Similarity	NPD1245	Approved
0.6607	Remote Similarity	NPD1508	Approved
0.6606	Remote Similarity	NPD1282	Approved
0.6597	Remote Similarity	NPD6273	Approved
0.6594	Remote Similarity	NPD3748	Approved
0.6593	Remote Similarity	NPD7961	Discontinued
0.6593	Remote Similarity	NPD520	Approved
0.6591	Remote Similarity	NPD5647	Approved
0.6589	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD1607	Approved
0.6567	Remote Similarity	NPD6966	Discovery
0.6562	Remote Similarity	NPD9272	Approved
0.6562	Remote Similarity	NPD17	Approved
0.6562	Remote Similarity	NPD2345	Approved
0.656	Remote Similarity	NPD256	Approved
0.656	Remote Similarity	NPD255	Approved
0.6547	Remote Similarity	NPD5404	Approved
0.6547	Remote Similarity	NPD5406	Approved
0.6547	Remote Similarity	NPD5405	Approved
0.6547	Remote Similarity	NPD5408	Approved
0.6544	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD2979	Phase 3
0.6544	Remote Similarity	NPD3373	Approved
0.6544	Remote Similarity	NPD4307	Phase 2
0.6538	Remote Similarity	NPD6637	Approved
0.6538	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD2650	Approved
0.6532	Remote Similarity	NPD2652	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