NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	212.08
Volume:	232.713
LogP:	3.43
LogD:	3.503
LogS:	-3.417
# Rotatable Bonds:	3
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.849
Synthetic Accessibility Score:	1.417
Fsp3:	0.071
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.796
MDCK Permeability:	2.8080805350327864e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.551
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.385
Plasma Protein Binding (PPB):	96.31035614013672%
Volume Distribution (VD):	0.198
Pgp-substrate:	1.8254188299179077%

ADMET: Metabolism

CYP1A2-inhibitor:	0.18
CYP1A2-substrate:	0.078
CYP2C19-inhibitor:	0.079
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.483
CYP2C9-substrate:	0.08
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.094
CYP3A4-inhibitor:	0.013
CYP3A4-substrate:	0.238

ADMET: Excretion

Clearance (CL):	2.972
Half-life (T1/2):	0.868

ADMET: Toxicity

hERG Blockers:	0.126
Human Hepatotoxicity (H-HT):	0.739
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.116
Carcinogencity:	0.044
Eye Corrosion:	0.007
Eye Irritation:	0.972
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC255676

Natural Product ID:	NPC255676
*Common Name:**	2-Benzylbenzoic Acid
IUPAC Name:	2-benzylbenzoic acid
Synonyms:
Standard InCHIKey:	FESDHLLVLYZNFY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O2/c15-14(16)13-9-5-4-8-12(13)10-11-6-2-1-3-7-11/h1-9H,10H2,(H,15,16)
SMILES:	OC(=O)c1ccccc1Cc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1879588
PubChem CID:	11924
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000369] Diphenylmethanes

*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
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121251]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22612410]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12088	Conyza canadensis	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
IC50	1
Potency	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	26679.5	nM	PMID[468448]
NPT5475	Individual Protein	Beta-lactamase VIM-2	Pseudomonas aeruginosa	IC50	>	1000000.0	nM	PMID[468449]

☑ 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 NPC255676 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	286
0.1-0.2	1466
0.2-0.3	3427
0.3-0.4	10090
0.4-0.5	11193
0.5-0.6	11250
0.6-0.7	4241
0.7-0.8	681
0.8-0.85	40
0.85-0.9	15
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.95	High Similarity	NPC318327
0.9394	High Similarity	NPC105899
0.9375	High Similarity	NPC229242
0.9223	High Similarity	NPC66208
0.9091	High Similarity	NPC284477
0.9091	High Similarity	NPC304873
0.9082	High Similarity	NPC217621
0.899	High Similarity	NPC282895
0.89	High Similarity	NPC25458
0.8878	High Similarity	NPC253423
0.8842	High Similarity	NPC62765
0.8796	High Similarity	NPC158157
0.8785	High Similarity	NPC186933
0.8776	High Similarity	NPC61944
0.8763	High Similarity	NPC261181
0.8673	High Similarity	NPC172925
0.8654	High Similarity	NPC249811
0.8654	High Similarity	NPC211439
0.8627	High Similarity	NPC329556
0.8571	High Similarity	NPC85493
0.8544	High Similarity	NPC249067
0.8519	High Similarity	NPC196673
0.8515	High Similarity	NPC228435
0.844	Intermediate Similarity	NPC306740
0.8431	Intermediate Similarity	NPC42211
0.8421	Intermediate Similarity	NPC318107
0.8411	Intermediate Similarity	NPC260818
0.8411	Intermediate Similarity	NPC474057
0.8365	Intermediate Similarity	NPC114594
0.8333	Intermediate Similarity	NPC158282
0.8333	Intermediate Similarity	NPC321852
0.8333	Intermediate Similarity	NPC118343
0.8333	Intermediate Similarity	NPC79496
0.8286	Intermediate Similarity	NPC209632
0.8286	Intermediate Similarity	NPC134120
0.8273	Intermediate Similarity	NPC476357
0.8269	Intermediate Similarity	NPC60679
0.8257	Intermediate Similarity	NPC272524
0.819	Intermediate Similarity	NPC31786
0.8182	Intermediate Similarity	NPC153053
0.8182	Intermediate Similarity	NPC110704
0.8174	Intermediate Similarity	NPC269923
0.8174	Intermediate Similarity	NPC167323
0.8173	Intermediate Similarity	NPC45613
0.8144	Intermediate Similarity	NPC322387
0.8131	Intermediate Similarity	NPC141523
0.812	Intermediate Similarity	NPC236189
0.8119	Intermediate Similarity	NPC130398
0.8105	Intermediate Similarity	NPC285773
0.8103	Intermediate Similarity	NPC244351
0.8103	Intermediate Similarity	NPC283514
0.8095	Intermediate Similarity	NPC89886
0.8073	Intermediate Similarity	NPC475002
0.8073	Intermediate Similarity	NPC210089
0.8073	Intermediate Similarity	NPC95126
0.8073	Intermediate Similarity	NPC167504
0.8061	Intermediate Similarity	NPC329064
0.8056	Intermediate Similarity	NPC269023
0.8056	Intermediate Similarity	NPC265407
0.8056	Intermediate Similarity	NPC99846
0.8056	Intermediate Similarity	NPC83628
0.8053	Intermediate Similarity	NPC228318
0.8037	Intermediate Similarity	NPC119271
0.8037	Intermediate Similarity	NPC30594
0.8037	Intermediate Similarity	NPC37622
0.8036	Intermediate Similarity	NPC322197
0.8034	Intermediate Similarity	NPC85511
0.8019	Intermediate Similarity	NPC329282
0.8018	Intermediate Similarity	NPC237366
0.8017	Intermediate Similarity	NPC198336
0.7981	Intermediate Similarity	NPC203925
0.7963	Intermediate Similarity	NPC56493
0.7961	Intermediate Similarity	NPC249912
0.7961	Intermediate Similarity	NPC156021
0.7961	Intermediate Similarity	NPC92754
0.7961	Intermediate Similarity	NPC289201
0.7961	Intermediate Similarity	NPC276775
0.7946	Intermediate Similarity	NPC474685
0.7944	Intermediate Similarity	NPC269457
0.7928	Intermediate Similarity	NPC128368
0.7925	Intermediate Similarity	NPC291426
0.7925	Intermediate Similarity	NPC274443
0.7913	Intermediate Similarity	NPC184579
0.7913	Intermediate Similarity	NPC233165
0.7909	Intermediate Similarity	NPC474157
0.7905	Intermediate Similarity	NPC70624
0.79	Intermediate Similarity	NPC274455
0.79	Intermediate Similarity	NPC70940
0.79	Intermediate Similarity	NPC86670
0.7895	Intermediate Similarity	NPC125252
0.789	Intermediate Similarity	NPC17525
0.789	Intermediate Similarity	NPC17417
0.789	Intermediate Similarity	NPC10251
0.7885	Intermediate Similarity	NPC78701
0.7885	Intermediate Similarity	NPC175852
0.7885	Intermediate Similarity	NPC35448
0.7885	Intermediate Similarity	NPC210529
0.7885	Intermediate Similarity	NPC225060
0.7885	Intermediate Similarity	NPC160548
0.7881	Intermediate Similarity	NPC275145
0.787	Intermediate Similarity	NPC187913
0.787	Intermediate Similarity	NPC37914
0.7863	Intermediate Similarity	NPC120545
0.7857	Intermediate Similarity	NPC307651
0.7857	Intermediate Similarity	NPC471721
0.7851	Intermediate Similarity	NPC95537
0.785	Intermediate Similarity	NPC324786
0.785	Intermediate Similarity	NPC472221
0.785	Intermediate Similarity	NPC472222
0.7838	Intermediate Similarity	NPC270699
0.7838	Intermediate Similarity	NPC186128
0.7838	Intermediate Similarity	NPC82899
0.783	Intermediate Similarity	NPC244427
0.783	Intermediate Similarity	NPC188895
0.783	Intermediate Similarity	NPC222390
0.7826	Intermediate Similarity	NPC328694
0.7818	Intermediate Similarity	NPC93084
0.7818	Intermediate Similarity	NPC196246
0.7818	Intermediate Similarity	NPC214067
0.7818	Intermediate Similarity	NPC174099
0.7818	Intermediate Similarity	NPC251854
0.7815	Intermediate Similarity	NPC295664
0.781	Intermediate Similarity	NPC325497
0.781	Intermediate Similarity	NPC146351
0.7798	Intermediate Similarity	NPC156648
0.7798	Intermediate Similarity	NPC34715
0.7797	Intermediate Similarity	NPC300274
0.7797	Intermediate Similarity	NPC91478
0.7797	Intermediate Similarity	NPC223351
0.7797	Intermediate Similarity	NPC68167
0.7797	Intermediate Similarity	NPC46634
0.7789	Intermediate Similarity	NPC127343
0.7788	Intermediate Similarity	NPC270654
0.7788	Intermediate Similarity	NPC274839
0.7778	Intermediate Similarity	NPC179092
0.7778	Intermediate Similarity	NPC26433
0.7778	Intermediate Similarity	NPC244994
0.7778	Intermediate Similarity	NPC222876
0.7778	Intermediate Similarity	NPC115188
0.7778	Intermediate Similarity	NPC292665
0.7778	Intermediate Similarity	NPC35856
0.7778	Intermediate Similarity	NPC472981
0.7778	Intermediate Similarity	NPC172483
0.7778	Intermediate Similarity	NPC272454
0.7778	Intermediate Similarity	NPC178395
0.7778	Intermediate Similarity	NPC301987
0.7778	Intermediate Similarity	NPC159760
0.7769	Intermediate Similarity	NPC115797
0.7769	Intermediate Similarity	NPC51448
0.7768	Intermediate Similarity	NPC93287
0.7768	Intermediate Similarity	NPC231717
0.7759	Intermediate Similarity	NPC472708
0.7757	Intermediate Similarity	NPC247976
0.775	Intermediate Similarity	NPC275576
0.7748	Intermediate Similarity	NPC476003
0.7748	Intermediate Similarity	NPC1082
0.7748	Intermediate Similarity	NPC133308
0.7748	Intermediate Similarity	NPC116842
0.7748	Intermediate Similarity	NPC305912
0.7748	Intermediate Similarity	NPC243355
0.7739	Intermediate Similarity	NPC160199
0.7736	Intermediate Similarity	NPC52472
0.7732	Intermediate Similarity	NPC44830
0.7731	Intermediate Similarity	NPC375356
0.7724	Intermediate Similarity	NPC31539
0.7719	Intermediate Similarity	NPC149691
0.7714	Intermediate Similarity	NPC329387
0.7714	Intermediate Similarity	NPC317280
0.7706	Intermediate Similarity	NPC69332
0.7706	Intermediate Similarity	NPC29989
0.7706	Intermediate Similarity	NPC95178
0.7706	Intermediate Similarity	NPC184658
0.7699	Intermediate Similarity	NPC211421
0.7699	Intermediate Similarity	NPC308744
0.7686	Intermediate Similarity	NPC169913
0.7679	Intermediate Similarity	NPC268388
0.7667	Intermediate Similarity	NPC164014
0.7667	Intermediate Similarity	NPC142956
0.7664	Intermediate Similarity	NPC320891
0.7658	Intermediate Similarity	NPC88141
0.7658	Intermediate Similarity	NPC95172
0.7652	Intermediate Similarity	NPC108288
0.7652	Intermediate Similarity	NPC212891
0.7652	Intermediate Similarity	NPC477453
0.7642	Intermediate Similarity	NPC245561
0.7636	Intermediate Similarity	NPC203732
0.7636	Intermediate Similarity	NPC29883
0.7636	Intermediate Similarity	NPC226699
0.7632	Intermediate Similarity	NPC221275
0.7632	Intermediate Similarity	NPC81808
0.7632	Intermediate Similarity	NPC210092
0.7632	Intermediate Similarity	NPC93181
0.7627	Intermediate Similarity	NPC165197
0.7627	Intermediate Similarity	NPC216216
0.7624	Intermediate Similarity	NPC9822
0.7624	Intermediate Similarity	NPC199567
0.7607	Intermediate Similarity	NPC204784
0.7603	Intermediate Similarity	NPC103540
0.7603	Intermediate Similarity	NPC470765
0.7593	Intermediate Similarity	NPC474365

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 NPC255676 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	926
0.2-0.3	1140
0.3-0.4	2647
0.4-0.5	2511
0.5-0.6	1185
0.6-0.7	362
0.7-0.8	81
0.8-0.85	9
0.85-0.9	8
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8962	High Similarity	NPD5951	Approved
0.8842	High Similarity	NPD9256	Approved
0.8842	High Similarity	NPD9258	Approved
0.8763	High Similarity	NPD1202	Approved
0.8673	High Similarity	NPD688	Clinical (unspecified phase)
0.8627	High Similarity	NPD1930	Approved
0.8627	High Similarity	NPD1929	Approved
0.8627	High Similarity	NPD1931	Clinical (unspecified phase)
0.8571	High Similarity	NPD6831	Clinical (unspecified phase)
0.8544	High Similarity	NPD1237	Approved
0.8482	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD9259	Approved
0.8421	Intermediate Similarity	NPD9257	Approved
0.8367	Intermediate Similarity	NPD1239	Approved
0.835	Intermediate Similarity	NPD1932	Approved
0.8333	Intermediate Similarity	NPD1238	Approved
0.819	Intermediate Similarity	NPD164	Approved
0.8155	Intermediate Similarity	NPD2066	Phase 3
0.8105	Intermediate Similarity	NPD9491	Approved
0.7961	Intermediate Similarity	NPD1566	Phase 3
0.7961	Intermediate Similarity	NPD1565	Approved
0.7961	Intermediate Similarity	NPD1564	Approved
0.7909	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.79	Intermediate Similarity	NPD1086	Approved
0.79	Intermediate Similarity	NPD1089	Approved
0.79	Intermediate Similarity	NPD1090	Approved
0.7895	Intermediate Similarity	NPD226	Approved
0.789	Intermediate Similarity	NPD2329	Discontinued
0.789	Intermediate Similarity	NPD2182	Approved
0.7885	Intermediate Similarity	NPD9495	Approved
0.7838	Intermediate Similarity	NPD9508	Approved
0.78	Intermediate Similarity	NPD800	Approved
0.7787	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD7008	Discontinued
0.7767	Intermediate Similarity	NPD9260	Approved
0.775	Intermediate Similarity	NPD1164	Approved
0.7745	Intermediate Similarity	NPD1088	Approved
0.7731	Intermediate Similarity	NPD182	Clinical (unspecified phase)
0.7724	Intermediate Similarity	NPD3764	Approved
0.7712	Intermediate Similarity	NPD1201	Approved
0.7685	Intermediate Similarity	NPD5909	Discontinued
0.7684	Intermediate Similarity	NPD9490	Approved
0.767	Intermediate Similarity	NPD1563	Approved
0.767	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7652	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD4878	Approved
0.7636	Intermediate Similarity	NPD9264	Approved
0.7636	Intermediate Similarity	NPD9267	Approved
0.7636	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD9263	Approved
0.7611	Intermediate Similarity	NPD5277	Phase 2
0.7603	Intermediate Similarity	NPD1470	Approved
0.76	Intermediate Similarity	NPD1087	Approved
0.7596	Intermediate Similarity	NPD1693	Approved
0.7579	Intermediate Similarity	NPD225	Approved
0.7579	Intermediate Similarity	NPD227	Approved
0.7568	Intermediate Similarity	NPD74	Approved
0.7568	Intermediate Similarity	NPD9266	Approved
0.7551	Intermediate Similarity	NPD3971	Phase 1
0.7526	Intermediate Similarity	NPD942	Approved
0.7524	Intermediate Similarity	NPD1989	Approved
0.7522	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7478	Intermediate Similarity	NPD2629	Approved
0.7478	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4793	Discontinued
0.7404	Intermediate Similarity	NPD1508	Approved
0.7398	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD2345	Approved
0.7377	Intermediate Similarity	NPD1888	Phase 1
0.736	Intermediate Similarity	NPD6966	Discovery
0.735	Intermediate Similarity	NPD9493	Approved
0.7311	Intermediate Similarity	NPD4102	Approved
0.7311	Intermediate Similarity	NPD4105	Approved
0.7308	Intermediate Similarity	NPD5405	Approved
0.7308	Intermediate Similarity	NPD5404	Approved
0.7308	Intermediate Similarity	NPD5406	Approved
0.7308	Intermediate Similarity	NPD5408	Approved
0.7282	Intermediate Similarity	NPD5346	Phase 2
0.7282	Intermediate Similarity	NPD5347	Phase 2
0.7281	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6287	Discontinued
0.7273	Intermediate Similarity	NPD9261	Approved
0.7263	Intermediate Similarity	NPD9716	Approved
0.7255	Intermediate Similarity	NPD650	Approved
0.725	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1283	Approved
0.7227	Intermediate Similarity	NPD9545	Approved
0.7196	Intermediate Similarity	NPD1843	Approved
0.7196	Intermediate Similarity	NPD5206	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD1317	Discontinued
0.719	Intermediate Similarity	NPD4136	Approved
0.719	Intermediate Similarity	NPD4106	Approved
0.719	Intermediate Similarity	NPD4135	Approved
0.7179	Intermediate Similarity	NPD1246	Approved
0.7179	Intermediate Similarity	NPD9281	Approved
0.7177	Intermediate Similarity	NPD1203	Approved
0.7165	Intermediate Similarity	NPD2313	Discontinued
0.7154	Intermediate Similarity	NPD5157	Phase 1
0.7154	Intermediate Similarity	NPD5159	Phase 2
0.7154	Intermediate Similarity	NPD5158	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7609	Phase 3
0.7121	Intermediate Similarity	NPD2346	Discontinued
0.712	Intermediate Similarity	NPD2798	Approved
0.712	Intermediate Similarity	NPD4980	Approved
0.7117	Intermediate Similarity	NPD6647	Phase 2
0.7107	Intermediate Similarity	NPD5305	Approved
0.7107	Intermediate Similarity	NPD5306	Approved
0.7107	Intermediate Similarity	NPD1104	Approved
0.7097	Intermediate Similarity	NPD1876	Approved
0.709	Intermediate Similarity	NPD7003	Approved
0.709	Intermediate Similarity	NPD3750	Approved
0.7077	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD7631	Approved
0.7073	Intermediate Similarity	NPD1608	Approved
0.7071	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD4879	Approved
0.7049	Intermediate Similarity	NPD1889	Phase 1
0.704	Intermediate Similarity	NPD2797	Approved
0.7025	Intermediate Similarity	NPD1245	Approved
0.7025	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3020	Approved
0.6992	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4806	Approved
0.6992	Remote Similarity	NPD4807	Approved
0.6992	Remote Similarity	NPD1281	Approved
0.6991	Remote Similarity	NPD5048	Discontinued
0.6972	Remote Similarity	NPD3495	Discontinued
0.697	Remote Similarity	NPD4308	Phase 3
0.697	Remote Similarity	NPD2799	Discontinued
0.6967	Remote Similarity	NPD2932	Approved
0.6967	Remote Similarity	NPD3019	Approved
0.6967	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1574	Approved
0.6944	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD6049	Phase 2
0.6939	Remote Similarity	NPD9294	Approved
0.6935	Remote Similarity	NPD9717	Approved
0.6917	Remote Similarity	NPD2935	Discontinued
0.6909	Remote Similarity	NPD253	Approved
0.6893	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD1625	Approved
0.6887	Remote Similarity	NPD3673	Approved
0.6887	Remote Similarity	NPD3672	Approved
0.6881	Remote Similarity	NPD2860	Approved
0.6881	Remote Similarity	NPD2859	Approved
0.6866	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7610	Discontinued
0.6842	Remote Similarity	NPD3748	Approved
0.6842	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD4628	Phase 3
0.6833	Remote Similarity	NPD255	Approved
0.6833	Remote Similarity	NPD256	Approved
0.6829	Remote Similarity	NPD9272	Approved
0.6829	Remote Similarity	NPD17	Approved
0.6814	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD1894	Discontinued
0.6803	Remote Similarity	NPD7009	Phase 2
0.68	Remote Similarity	NPD1481	Phase 2
0.68	Remote Similarity	NPD3972	Approved
0.6797	Remote Similarity	NPD5204	Approved
0.6794	Remote Similarity	NPD4453	Approved
0.6794	Remote Similarity	NPD4445	Approved
0.6794	Remote Similarity	NPD943	Approved
0.6794	Remote Similarity	NPD4452	Approved
0.6789	Remote Similarity	NPD2933	Approved
0.6789	Remote Similarity	NPD2934	Approved
0.6786	Remote Similarity	NPD1616	Discontinued
0.6777	Remote Similarity	NPD3797	Approved
0.6769	Remote Similarity	NPD3268	Approved
0.6748	Remote Similarity	NPD9268	Approved
0.6744	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4617	Approved
0.6744	Remote Similarity	NPD5203	Approved
0.6744	Remote Similarity	NPD4620	Approved
0.6744	Remote Similarity	NPD5201	Approved
0.6741	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD2342	Discontinued
0.672	Remote Similarity	NPD1535	Discovery
0.672	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6718	Remote Similarity	NPD7714	Approved
0.6718	Remote Similarity	NPD6663	Approved
0.6718	Remote Similarity	NPD7715	Approved
0.6714	Remote Similarity	NPD6273	Approved
0.6696	Remote Similarity	NPD7798	Approved
0.6696	Remote Similarity	NPD9712	Approved
0.6696	Remote Similarity	NPD3097	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD3644	Approved
0.6695	Remote Similarity	NPD3642	Approved
0.6695	Remote Similarity	NPD3643	Approved
0.6694	Remote Similarity	NPD4198	Discontinued
0.669	Remote Similarity	NPD3226	Approved
0.669	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5086	Approved
0.669	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3798	Phase 3
0.6667	Remote Similarity	NPD1280	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD4307	Phase 2
0.6667	Remote Similarity	NPD1240	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