NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	226.1
Volume:	250.009
LogP:	3.834
LogD:	3.838
LogS:	-4.498
# Rotatable Bonds:	5
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.749
Synthetic Accessibility Score:	1.332
Fsp3:	0.133
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:	-4.51
MDCK Permeability:	2.622914507810492e-05
Pgp-inhibitor:	0.052
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.899
30% Bioavailability (F30%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.151
Plasma Protein Binding (PPB):	98.45659637451172%
Volume Distribution (VD):	0.812
Pgp-substrate:	1.7088817358016968%

ADMET: Metabolism

CYP1A2-inhibitor:	0.987
CYP1A2-substrate:	0.238
CYP2C19-inhibitor:	0.971
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.854
CYP2C9-substrate:	0.185
CYP2D6-inhibitor:	0.192
CYP2D6-substrate:	0.12
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.256

ADMET: Excretion

Clearance (CL):	12.286
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.19
Human Hepatotoxicity (H-HT):	0.019
Drug-inuced Liver Injury (DILI):	0.427
AMES Toxicity:	0.018
Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.02
Skin Sensitization:	0.873
Carcinogencity:	0.414
Eye Corrosion:	0.041
Eye Irritation:	0.988
Respiratory Toxicity:	0.044

Download Data

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

Natural Product: NPC42211

Natural Product ID:	NPC42211
*Common Name:**	Phenethyl Benzoate
IUPAC Name:	2-phenylethyl benzoate
Synonyms:
Standard InCHIKey:	OSORMYZMWHVFOZ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O2/c16-15(14-9-5-2-6-10-14)17-12-11-13-7-3-1-4-8-13/h1-10H,11-12H2
SMILES:	c1ccc(cc1)CCOC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2252208
PubChem CID:	7194
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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO32976	balantiopsis cancellata	Species	Balantiopsidaceae	Eukaryota	n.a.	Chile	n.a.	PMID[15656657]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	1
Others	2
Potency	11

Activity Type	# Activity
Individual Protein	2
Organism	3
Others	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT1780	Organism	Davidiella tassiana	Davidiella tassiana	MIC	=	0.1	mg	PMID[469588]
NPT776	Organism	Spodoptera littoralis	Spodoptera littoralis	Ratio	=	0.56	n.a.	PMID[469588]
NPT176	Organism	Artemia salina	Artemia salina	LC50	<	2.5	ppm	PMID[469588]
NPT2	Others	Unspecified		Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	13685.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	19496.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	21689.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	611.3	nM	PubChem BioAssay data set
NPT74	Individual Protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	13802.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	385.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	61652.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified		Potency	n.a.	1722.9	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 NPC42211 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	287
0.1-0.2	1762
0.2-0.3	3929
0.3-0.4	10427
0.4-0.5	10160
0.5-0.6	10998
0.6-0.7	4594
0.7-0.8	425
0.8-0.85	61
0.85-0.9	37
0.9-0.95	15
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9892	High Similarity	NPC118343
0.9468	High Similarity	NPC92754
0.9468	High Similarity	NPC249912
0.9468	High Similarity	NPC276775
0.9388	High Similarity	NPC269457
0.9368	High Similarity	NPC225060
0.9368	High Similarity	NPC35448
0.9368	High Similarity	NPC78701
0.9271	High Similarity	NPC146351
0.9255	High Similarity	NPC130398
0.9175	High Similarity	NPC70624
0.9062	High Similarity	NPC270654
0.9029	High Similarity	NPC79496
0.9029	High Similarity	NPC158282
0.899	High Similarity	NPC301943
0.899	High Similarity	NPC89886
0.899	High Similarity	NPC60679
0.899	High Similarity	NPC474365
0.8947	High Similarity	NPC261181
0.8936	High Similarity	NPC119631
0.8911	High Similarity	NPC119271
0.89	High Similarity	NPC114594
0.8889	High Similarity	NPC188895
0.8878	High Similarity	NPC325497
0.8878	High Similarity	NPC203925
0.8824	High Similarity	NPC56493
0.8812	High Similarity	NPC209632
0.8762	High Similarity	NPC128368
0.875	High Similarity	NPC167504
0.875	High Similarity	NPC210089
0.875	High Similarity	NPC474157
0.8738	High Similarity	NPC265407
0.8738	High Similarity	NPC83628
0.8738	High Similarity	NPC17417
0.8738	High Similarity	NPC469636
0.8738	High Similarity	NPC10251
0.8723	High Similarity	NPC173443
0.8713	High Similarity	NPC31786
0.87	High Similarity	NPC45613
0.8654	High Similarity	NPC93084
0.8654	High Similarity	NPC251854
0.8654	High Similarity	NPC174099
0.8654	High Similarity	NPC214067
0.8654	High Similarity	NPC196246
0.8632	High Similarity	NPC213156
0.8632	High Similarity	NPC240108
0.8602	High Similarity	NPC318107
0.8585	High Similarity	NPC272524
0.8571	High Similarity	NPC1082
0.8571	High Similarity	NPC305912
0.8571	High Similarity	NPC260818
0.8558	High Similarity	NPC99846
0.8558	High Similarity	NPC269023
0.8558	High Similarity	NPC474364
0.8544	High Similarity	NPC37622
0.8544	High Similarity	NPC30594
0.8526	High Similarity	NPC9822
0.8511	High Similarity	NPC89377
0.8505	High Similarity	NPC308744
0.8491	Intermediate Similarity	NPC82899
0.8491	Intermediate Similarity	NPC321852
0.8491	Intermediate Similarity	NPC270699
0.8431	Intermediate Similarity	NPC255676
0.8426	Intermediate Similarity	NPC306740
0.8426	Intermediate Similarity	NPC210092
0.8426	Intermediate Similarity	NPC474685
0.8411	Intermediate Similarity	NPC474176
0.8396	Intermediate Similarity	NPC476003
0.8381	Intermediate Similarity	NPC85493
0.8364	Intermediate Similarity	NPC45104
0.8364	Intermediate Similarity	NPC469574
0.8349	Intermediate Similarity	NPC149691
0.8349	Intermediate Similarity	NPC100353
0.8333	Intermediate Similarity	NPC153053
0.8333	Intermediate Similarity	NPC220893
0.8333	Intermediate Similarity	NPC307651
0.8318	Intermediate Similarity	NPC474314
0.8298	Intermediate Similarity	NPC58616
0.8298	Intermediate Similarity	NPC294134
0.8269	Intermediate Similarity	NPC105899
0.8247	Intermediate Similarity	NPC62765
0.8241	Intermediate Similarity	NPC161611
0.8229	Intermediate Similarity	NPC304760
0.8224	Intermediate Similarity	NPC243355
0.8218	Intermediate Similarity	NPC229242
0.8198	Intermediate Similarity	NPC228318
0.8173	Intermediate Similarity	NPC249067
0.8173	Intermediate Similarity	NPC269644
0.8165	Intermediate Similarity	NPC237366
0.8165	Intermediate Similarity	NPC474363
0.8142	Intermediate Similarity	NPC473243
0.8142	Intermediate Similarity	NPC233282
0.8137	Intermediate Similarity	NPC217621
0.8137	Intermediate Similarity	NPC472318
0.8137	Intermediate Similarity	NPC98911
0.8119	Intermediate Similarity	NPC253423
0.8085	Intermediate Similarity	NPC288903
0.8081	Intermediate Similarity	NPC77273
0.8065	Intermediate Similarity	NPC165212
0.8058	Intermediate Similarity	NPC473325
0.8037	Intermediate Similarity	NPC318327
0.8037	Intermediate Similarity	NPC281604
0.802	Intermediate Similarity	NPC61944
0.8	Intermediate Similarity	NPC477411
0.8	Intermediate Similarity	NPC196075
0.7981	Intermediate Similarity	NPC25458
0.7981	Intermediate Similarity	NPC284477
0.7981	Intermediate Similarity	NPC304873
0.7949	Intermediate Similarity	NPC295664
0.7946	Intermediate Similarity	NPC128249
0.7944	Intermediate Similarity	NPC156648
0.7944	Intermediate Similarity	NPC470391
0.7913	Intermediate Similarity	NPC50872
0.7905	Intermediate Similarity	NPC234305
0.7895	Intermediate Similarity	NPC208183
0.7895	Intermediate Similarity	NPC243289
0.7885	Intermediate Similarity	NPC282895
0.7876	Intermediate Similarity	NPC217423
0.7857	Intermediate Similarity	NPC226093
0.783	Intermediate Similarity	NPC85977
0.7818	Intermediate Similarity	NPC212415
0.7818	Intermediate Similarity	NPC66208
0.7807	Intermediate Similarity	NPC94298
0.7807	Intermediate Similarity	NPC94637
0.7807	Intermediate Similarity	NPC27633
0.78	Intermediate Similarity	NPC110704
0.7789	Intermediate Similarity	NPC323103
0.7788	Intermediate Similarity	NPC228435
0.7788	Intermediate Similarity	NPC316062
0.7778	Intermediate Similarity	NPC223351
0.7778	Intermediate Similarity	NPC211439
0.7768	Intermediate Similarity	NPC474095
0.7768	Intermediate Similarity	NPC81808
0.7768	Intermediate Similarity	NPC474408
0.7767	Intermediate Similarity	NPC289201
0.7766	Intermediate Similarity	NPC121800
0.7759	Intermediate Similarity	NPC144547
0.7755	Intermediate Similarity	NPC96625
0.7748	Intermediate Similarity	NPC13784
0.7742	Intermediate Similarity	NPC176228
0.7739	Intermediate Similarity	NPC328459
0.7739	Intermediate Similarity	NPC90522
0.7739	Intermediate Similarity	NPC201284
0.7736	Intermediate Similarity	NPC329556
0.7736	Intermediate Similarity	NPC160382
0.7731	Intermediate Similarity	NPC275576
0.7731	Intermediate Similarity	NPC470765
0.7731	Intermediate Similarity	NPC4164
0.7719	Intermediate Similarity	NPC469954
0.7708	Intermediate Similarity	NPC308619
0.7708	Intermediate Similarity	NPC127491
0.7708	Intermediate Similarity	NPC324835
0.7708	Intermediate Similarity	NPC270507
0.7708	Intermediate Similarity	NPC285773
0.7706	Intermediate Similarity	NPC206341
0.7706	Intermediate Similarity	NPC40178
0.77	Intermediate Similarity	NPC185501
0.7699	Intermediate Similarity	NPC188907
0.7699	Intermediate Similarity	NPC220540
0.7699	Intermediate Similarity	NPC135730
0.7692	Intermediate Similarity	NPC160548
0.7692	Intermediate Similarity	NPC175852
0.7692	Intermediate Similarity	NPC210529
0.7692	Intermediate Similarity	NPC314329
0.7692	Intermediate Similarity	NPC26285
0.7686	Intermediate Similarity	NPC301857
0.7686	Intermediate Similarity	NPC2596
0.7685	Intermediate Similarity	NPC472316
0.7685	Intermediate Similarity	NPC472315
0.7685	Intermediate Similarity	NPC1065
0.7685	Intermediate Similarity	NPC475203
0.7685	Intermediate Similarity	NPC474376
0.7679	Intermediate Similarity	NPC87069
0.7679	Intermediate Similarity	NPC279916
0.7672	Intermediate Similarity	NPC988
0.7672	Intermediate Similarity	NPC72977
0.7672	Intermediate Similarity	NPC289432
0.7667	Intermediate Similarity	NPC114096
0.7667	Intermediate Similarity	NPC473220
0.7667	Intermediate Similarity	NPC470753
0.7667	Intermediate Similarity	NPC169913
0.7664	Intermediate Similarity	NPC280616
0.7664	Intermediate Similarity	NPC242913
0.7664	Intermediate Similarity	NPC171831
0.766	Intermediate Similarity	NPC78517
0.766	Intermediate Similarity	NPC170484
0.766	Intermediate Similarity	NPC167577
0.7658	Intermediate Similarity	NPC23332
0.7652	Intermediate Similarity	NPC32298
0.7647	Intermediate Similarity	NPC125053
0.7647	Intermediate Similarity	NPC107846
0.7647	Intermediate Similarity	NPC23453
0.7636	Intermediate Similarity	NPC273837
0.7632	Intermediate Similarity	NPC190298
0.7632	Intermediate Similarity	NPC128825
0.7632	Intermediate Similarity	NPC470860
0.7632	Intermediate Similarity	NPC131192
0.7627	Intermediate Similarity	NPC475692
0.7627	Intermediate Similarity	NPC474283
0.7627	Intermediate Similarity	NPC472703

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 NPC42211 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	986
0.2-0.3	1104
0.3-0.4	2888
0.4-0.5	2324
0.5-0.6	1136
0.6-0.7	359
0.7-0.8	79
0.8-0.85	4
0.85-0.9	6
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9892	High Similarity	NPD1238	Approved
0.8947	High Similarity	NPD1202	Approved
0.8738	High Similarity	NPD2182	Approved
0.8713	High Similarity	NPD164	Approved
0.8602	High Similarity	NPD9257	Approved
0.8602	High Similarity	NPD9259	Approved
0.8571	High Similarity	NPD2181	Clinical (unspecified phase)
0.8247	Intermediate Similarity	NPD9256	Approved
0.8247	Intermediate Similarity	NPD9258	Approved
0.8173	Intermediate Similarity	NPD1237	Approved
0.802	Intermediate Similarity	NPD1989	Approved
0.8	Intermediate Similarity	NPD6287	Discontinued
0.7921	Intermediate Similarity	NPD9260	Approved
0.7849	Intermediate Similarity	NPD9490	Approved
0.7818	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7807	Intermediate Similarity	NPD9545	Approved
0.7736	Intermediate Similarity	NPD1930	Approved
0.7736	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD1929	Approved
0.7708	Intermediate Similarity	NPD9491	Approved
0.7706	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD9495	Approved
0.7686	Intermediate Similarity	NPD6832	Phase 2
0.7679	Intermediate Similarity	NPD1241	Discontinued
0.7664	Intermediate Similarity	NPD5909	Discontinued
0.7647	Intermediate Similarity	NPD2198	Approved
0.7647	Intermediate Similarity	NPD2199	Approved
0.7632	Intermediate Similarity	NPD9493	Approved
0.7624	Intermediate Similarity	NPD1239	Approved
0.7623	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD5951	Approved
0.7611	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD2347	Approved
0.7553	Intermediate Similarity	NPD225	Approved
0.7553	Intermediate Similarity	NPD227	Approved
0.7524	Intermediate Similarity	NPD5926	Approved
0.75	Intermediate Similarity	NPD942	Approved
0.75	Intermediate Similarity	NPD1894	Discontinued
0.748	Intermediate Similarity	NPD7008	Discontinued
0.7477	Intermediate Similarity	NPD1932	Approved
0.7477	Intermediate Similarity	NPD2067	Discontinued
0.7476	Intermediate Similarity	NPD1563	Approved
0.7453	Intermediate Similarity	NPD2066	Phase 3
0.744	Intermediate Similarity	NPD3373	Approved
0.7438	Intermediate Similarity	NPD1203	Approved
0.7407	Intermediate Similarity	NPD9261	Approved
0.7404	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1087	Approved
0.74	Intermediate Similarity	NPD1282	Approved
0.7395	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7373	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD3672	Approved
0.7353	Intermediate Similarity	NPD3673	Approved
0.7333	Intermediate Similarity	NPD3972	Approved
0.732	Intermediate Similarity	NPD226	Approved
0.7304	Intermediate Similarity	NPD2629	Approved
0.7295	Intermediate Similarity	NPD9567	Approved
0.7295	Intermediate Similarity	NPD553	Approved
0.7295	Intermediate Similarity	NPD552	Approved
0.729	Intermediate Similarity	NPD7798	Approved
0.728	Intermediate Similarity	NPD3764	Approved
0.728	Intermediate Similarity	NPD2313	Discontinued
0.7264	Intermediate Similarity	NPD1564	Approved
0.7264	Intermediate Similarity	NPD1565	Approved
0.7264	Intermediate Similarity	NPD1566	Phase 3
0.7255	Intermediate Similarity	NPD800	Approved
0.7244	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7236	Intermediate Similarity	NPD1019	Discontinued
0.7236	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7227	Intermediate Similarity	NPD17	Approved
0.7227	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD5667	Approved
0.7213	Intermediate Similarity	NPD1876	Approved
0.7207	Intermediate Similarity	NPD3134	Approved
0.72	Intermediate Similarity	NPD6039	Approved
0.7193	Intermediate Similarity	NPD9508	Approved
0.719	Intermediate Similarity	NPD9717	Approved
0.7188	Intermediate Similarity	NPD3528	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD1086	Approved
0.7184	Intermediate Similarity	NPD1090	Approved
0.7184	Intermediate Similarity	NPD1089	Approved
0.7168	Intermediate Similarity	NPD5237	Approved
0.7168	Intermediate Similarity	NPD5240	Approved
0.7168	Intermediate Similarity	NPD5236	Approved
0.7168	Intermediate Similarity	NPD5235	Approved
0.7168	Intermediate Similarity	NPD5239	Approved
0.7165	Intermediate Similarity	NPD4307	Phase 2
0.7143	Intermediate Similarity	NPD1358	Approved
0.7143	Intermediate Similarity	NPD9267	Approved
0.7143	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9264	Approved
0.7143	Intermediate Similarity	NPD9263	Approved
0.713	Intermediate Similarity	NPD5277	Phase 2
0.7117	Intermediate Similarity	NPD9697	Approved
0.7109	Intermediate Similarity	NPD1933	Approved
0.7107	Intermediate Similarity	NPD1281	Approved
0.7099	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2798	Approved
0.7091	Intermediate Similarity	NPD6647	Phase 2
0.7087	Intermediate Similarity	NPD7713	Phase 3
0.708	Intermediate Similarity	NPD9266	Approved
0.708	Intermediate Similarity	NPD74	Approved
0.708	Intermediate Similarity	NPD2329	Discontinued
0.7049	Intermediate Similarity	NPD1481	Phase 2
0.7049	Intermediate Similarity	NPD1608	Approved
0.7048	Intermediate Similarity	NPD1088	Approved
0.7041	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1889	Phase 1
0.7025	Intermediate Similarity	NPD4136	Approved
0.7025	Intermediate Similarity	NPD4135	Approved
0.7025	Intermediate Similarity	NPD4106	Approved
0.7023	Intermediate Similarity	NPD1551	Phase 2
0.7018	Intermediate Similarity	NPD3646	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD2797	Approved
0.7016	Intermediate Similarity	NPD3266	Approved
0.7016	Intermediate Similarity	NPD3267	Approved
0.7	Intermediate Similarity	NPD2569	Approved
0.7	Intermediate Similarity	NPD5585	Approved
0.7	Intermediate Similarity	NPD2567	Approved
0.6992	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD1535	Discovery
0.6949	Remote Similarity	NPD4198	Discontinued
0.6947	Remote Similarity	NPD2799	Discontinued
0.6947	Remote Similarity	NPD4308	Phase 3
0.6947	Remote Similarity	NPD3748	Approved
0.6942	Remote Similarity	NPD5305	Approved
0.6942	Remote Similarity	NPD5306	Approved
0.694	Remote Similarity	NPD4628	Phase 3
0.6935	Remote Similarity	NPD1283	Approved
0.6923	Remote Similarity	NPD689	Discontinued
0.6916	Remote Similarity	NPD1693	Approved
0.6909	Remote Similarity	NPD2553	Approved
0.6909	Remote Similarity	NPD2552	Approved
0.6909	Remote Similarity	NPD2555	Approved
0.6909	Remote Similarity	NPD2549	Approved
0.6909	Remote Similarity	NPD2550	Approved
0.6909	Remote Similarity	NPD2558	Approved
0.6897	Remote Similarity	NPD969	Suspended
0.6894	Remote Similarity	NPD2935	Discontinued
0.6893	Remote Similarity	NPD4793	Discontinued
0.6893	Remote Similarity	NPD650	Approved
0.6889	Remote Similarity	NPD3887	Approved
0.6887	Remote Similarity	NPD1508	Approved
0.6885	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.688	Remote Similarity	NPD1164	Approved
0.6875	Remote Similarity	NPD9716	Approved
0.687	Remote Similarity	NPD1756	Approved
0.687	Remote Similarity	NPD1752	Approved
0.686	Remote Similarity	NPD4102	Approved
0.686	Remote Similarity	NPD4105	Approved
0.6855	Remote Similarity	NPD5159	Phase 2
0.6855	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD5157	Phase 1
0.6852	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4188	Approved
0.6847	Remote Similarity	NPD4189	Approved
0.6842	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD2353	Approved
0.6842	Remote Similarity	NPD2346	Discontinued
0.6842	Remote Similarity	NPD7611	Approved
0.6838	Remote Similarity	NPD7440	Discontinued
0.6838	Remote Similarity	NPD5535	Approved
0.6829	Remote Similarity	NPD4807	Approved
0.6829	Remote Similarity	NPD4806	Approved
0.6814	Remote Similarity	NPD5048	Discontinued
0.681	Remote Similarity	NPD2201	Approved
0.68	Remote Similarity	NPD1888	Phase 1
0.6794	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD6799	Approved
0.6774	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6769	Remote Similarity	NPD3142	Approved
0.6769	Remote Similarity	NPD2979	Phase 3
0.6769	Remote Similarity	NPD3140	Approved
0.6769	Remote Similarity	NPD1240	Approved
0.6767	Remote Similarity	NPD2796	Approved
0.6762	Remote Similarity	NPD5347	Phase 2
0.6762	Remote Similarity	NPD5346	Phase 2
0.675	Remote Similarity	NPD4574	Approved
0.675	Remote Similarity	NPD4576	Approved
0.6748	Remote Similarity	NPD3847	Discontinued
0.6744	Remote Similarity	NPD3268	Approved
0.6744	Remote Similarity	NPD6798	Discontinued
0.6744	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD2670	Approved
0.6739	Remote Similarity	NPD5401	Approved
0.6735	Remote Similarity	NPD9294	Approved
0.6726	Remote Similarity	NPD3048	Approved
0.6726	Remote Similarity	NPD3047	Approved
0.6726	Remote Similarity	NPD3046	Approved
0.6724	Remote Similarity	NPD4234	Approved
0.6724	Remote Similarity	NPD4233	Approved
0.6723	Remote Similarity	NPD9281	Approved
0.6723	Remote Similarity	NPD1246	Approved
0.6721	Remote Similarity	NPD1651	Approved
0.672	Remote Similarity	NPD4359	Approved
0.6718	Remote Similarity	NPD4618	Approved
0.6718	Remote Similarity	NPD230	Phase 1

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