NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.09
Volume:	258.799
LogP:	3.27
LogD:	3.881
LogS:	-3.656
# Rotatable Bonds:	5
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.773
Synthetic Accessibility Score:	1.427
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:	-4.601
MDCK Permeability:	3.167868999298662e-05
Pgp-inhibitor:	0.084
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.865

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.329
Plasma Protein Binding (PPB):	97.65361022949219%
Volume Distribution (VD):	0.846
Pgp-substrate:	2.880237579345703%

ADMET: Metabolism

CYP1A2-inhibitor:	0.986
CYP1A2-substrate:	0.876
CYP2C19-inhibitor:	0.973
CYP2C19-substrate:	0.107
CYP2C9-inhibitor:	0.694
CYP2C9-substrate:	0.649
CYP2D6-inhibitor:	0.377
CYP2D6-substrate:	0.658
CYP3A4-inhibitor:	0.321
CYP3A4-substrate:	0.359

ADMET: Excretion

Clearance (CL):	11.754
Half-life (T1/2):	0.903

ADMET: Toxicity

hERG Blockers:	0.181
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.802
AMES Toxicity:	0.162
Rat Oral Acute Toxicity:	0.015
Maximum Recommended Daily Dose:	0.007
Skin Sensitization:	0.339
Carcinogencity:	0.711
Eye Corrosion:	0.023
Eye Irritation:	0.973
Respiratory Toxicity:	0.036

Download Data

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

Natural Product: NPC45104

Natural Product ID:	NPC45104
*Common Name:**	2-Methoxybenzyl Benzoate
IUPAC Name:	(2-methoxyphenyl)methyl benzoate
Synonyms:	2-Methoxybenzyl Benzoate
Standard InCHIKey:	BZUHSQFJABFAHL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H14O3/c1-17-14-10-6-5-9-13(14)11-18-15(16)12-7-3-2-4-8-12/h2-10H,11H2,1H3
SMILES:	COc1ccccc1COC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498647
PubChem CID:	3085295
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
NPO32880	uvaria dac	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22676269]
NPO32880	uvaria dac	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23092429]
NPO40206	Monanthotaxis trichocarpa	Species	Annonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31986029]

☑ 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
Others	4

Activity Type	# Activity
Cell Line	3
Individual Protein	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1222	Individual Protein	Type-1A angiotensin II receptor	Mus musculus	IC50	=	117.4	ug.mL-1	PMID[486742]
NPT461	Cell Line	PANC-1	Homo sapiens	PC50	=	137.0	uM	PMID[486743]
NPT2107	Cell Line	PSN1	Homo sapiens	PC50	=	185.0	uM	PMID[486743]
NPT783	Cell Line	MIA PaCa-2	Homo sapiens	PC50	=	131.0	uM	PMID[486743]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	PC50	>	200.0	uM	PMID[486743]

☑ 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 NPC45104 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	318
0.1-0.2	1986
0.2-0.3	4813
0.3-0.4	11091
0.4-0.5	6435
0.5-0.6	5299
0.6-0.7	9493
0.7-0.8	3122
0.8-0.85	121
0.85-0.9	14
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9464	High Similarity	NPC217423
0.9286	High Similarity	NPC188907
0.9237	High Similarity	NPC4164
0.9052	High Similarity	NPC230951
0.8934	High Similarity	NPC238309
0.8926	High Similarity	NPC264428
0.8889	High Similarity	NPC233282
0.8772	High Similarity	NPC53953
0.8718	High Similarity	NPC94637
0.871	High Similarity	NPC12694
0.8667	High Similarity	NPC311219
0.8644	High Similarity	NPC90522
0.8644	High Similarity	NPC328459
0.8644	High Similarity	NPC201284
0.8621	High Similarity	NPC220540
0.8609	High Similarity	NPC279916
0.8584	High Similarity	NPC149545
0.8583	High Similarity	NPC314329
0.8571	High Similarity	NPC72977
0.8559	High Similarity	NPC32298
0.8547	High Similarity	NPC316062
0.8547	High Similarity	NPC128825
0.8525	High Similarity	NPC107846
0.8487	Intermediate Similarity	NPC35744
0.8487	Intermediate Similarity	NPC54243
0.8482	Intermediate Similarity	NPC1065
0.8475	Intermediate Similarity	NPC240664
0.8475	Intermediate Similarity	NPC469954
0.8455	Intermediate Similarity	NPC165556
0.844	Intermediate Similarity	NPC118343
0.8435	Intermediate Similarity	NPC57879
0.8435	Intermediate Similarity	NPC54626
0.8435	Intermediate Similarity	NPC23332
0.8417	Intermediate Similarity	NPC474874
0.8413	Intermediate Similarity	NPC473271
0.84	Intermediate Similarity	NPC2596
0.8393	Intermediate Similarity	NPC227255
0.839	Intermediate Similarity	NPC470860
0.8378	Intermediate Similarity	NPC179686
0.8376	Intermediate Similarity	NPC252004
0.8374	Intermediate Similarity	NPC193805
0.8374	Intermediate Similarity	NPC6888
0.8374	Intermediate Similarity	NPC470163
0.8374	Intermediate Similarity	NPC470162
0.8372	Intermediate Similarity	NPC66705
0.8364	Intermediate Similarity	NPC42211
0.8361	Intermediate Similarity	NPC291189
0.8361	Intermediate Similarity	NPC69403
0.8348	Intermediate Similarity	NPC183648
0.8333	Intermediate Similarity	NPC66246
0.8333	Intermediate Similarity	NPC61779
0.8333	Intermediate Similarity	NPC170546
0.832	Intermediate Similarity	NPC71525
0.832	Intermediate Similarity	NPC41721
0.832	Intermediate Similarity	NPC293387
0.8306	Intermediate Similarity	NPC2771
0.8288	Intermediate Similarity	NPC84325
0.8276	Intermediate Similarity	NPC233238
0.8268	Intermediate Similarity	NPC228184
0.8268	Intermediate Similarity	NPC282230
0.8268	Intermediate Similarity	NPC183348
0.8264	Intermediate Similarity	NPC246214
0.8264	Intermediate Similarity	NPC193193
0.8264	Intermediate Similarity	NPC470092
0.8264	Intermediate Similarity	NPC31314
0.8261	Intermediate Similarity	NPC234639
0.8257	Intermediate Similarity	NPC92754
0.8257	Intermediate Similarity	NPC276775
0.8257	Intermediate Similarity	NPC249912
0.825	Intermediate Similarity	NPC293424
0.825	Intermediate Similarity	NPC206007
0.825	Intermediate Similarity	NPC171023
0.824	Intermediate Similarity	NPC474264
0.8235	Intermediate Similarity	NPC33717
0.8235	Intermediate Similarity	NPC128633
0.823	Intermediate Similarity	NPC128730
0.823	Intermediate Similarity	NPC139891
0.8226	Intermediate Similarity	NPC221798
0.8226	Intermediate Similarity	NPC56332
0.8226	Intermediate Similarity	NPC89630
0.8226	Intermediate Similarity	NPC255073
0.8217	Intermediate Similarity	NPC287533
0.8203	Intermediate Similarity	NPC196979
0.8203	Intermediate Similarity	NPC15083
0.8203	Intermediate Similarity	NPC470977
0.8203	Intermediate Similarity	NPC470976
0.8195	Intermediate Similarity	NPC136095
0.819	Intermediate Similarity	NPC474157
0.8189	Intermediate Similarity	NPC211120
0.8182	Intermediate Similarity	NPC264976
0.8182	Intermediate Similarity	NPC35448
0.8182	Intermediate Similarity	NPC281356
0.8182	Intermediate Similarity	NPC225060
0.8182	Intermediate Similarity	NPC78701
0.8175	Intermediate Similarity	NPC37512
0.8175	Intermediate Similarity	NPC298884
0.8175	Intermediate Similarity	NPC161322
0.8158	Intermediate Similarity	NPC326447
0.8158	Intermediate Similarity	NPC176971
0.8145	Intermediate Similarity	NPC141252
0.8145	Intermediate Similarity	NPC93730
0.8145	Intermediate Similarity	NPC11799
0.8142	Intermediate Similarity	NPC38209
0.8142	Intermediate Similarity	NPC109637
0.814	Intermediate Similarity	NPC175159
0.814	Intermediate Similarity	NPC284424
0.8125	Intermediate Similarity	NPC42292
0.8125	Intermediate Similarity	NPC247779
0.8125	Intermediate Similarity	NPC307732
0.811	Intermediate Similarity	NPC2401
0.811	Intermediate Similarity	NPC125887
0.811	Intermediate Similarity	NPC475017
0.8108	Intermediate Similarity	NPC146351
0.8103	Intermediate Similarity	NPC259554
0.8099	Intermediate Similarity	NPC94298
0.8099	Intermediate Similarity	NPC166591
0.8099	Intermediate Similarity	NPC27633
0.8099	Intermediate Similarity	NPC152159
0.8099	Intermediate Similarity	NPC265547
0.8095	Intermediate Similarity	NPC475236
0.8092	Intermediate Similarity	NPC125269
0.8092	Intermediate Similarity	NPC470844
0.8087	Intermediate Similarity	NPC151530
0.8087	Intermediate Similarity	NPC157473
0.8083	Intermediate Similarity	NPC19290
0.808	Intermediate Similarity	NPC265910
0.808	Intermediate Similarity	NPC145134
0.808	Intermediate Similarity	NPC91475
0.8077	Intermediate Similarity	NPC182428
0.8077	Intermediate Similarity	NPC472591
0.8073	Intermediate Similarity	NPC130398
0.807	Intermediate Similarity	NPC209632
0.807	Intermediate Similarity	NPC269457
0.807	Intermediate Similarity	NPC238115
0.8067	Intermediate Similarity	NPC114144
0.8067	Intermediate Similarity	NPC87563
0.8067	Intermediate Similarity	NPC81808
0.8065	Intermediate Similarity	NPC217756
0.8065	Intermediate Similarity	NPC46634
0.8062	Intermediate Similarity	NPC472517
0.8053	Intermediate Similarity	NPC474365
0.8053	Intermediate Similarity	NPC301943
0.8053	Intermediate Similarity	NPC298224
0.8049	Intermediate Similarity	NPC235190
0.8049	Intermediate Similarity	NPC163200
0.8049	Intermediate Similarity	NPC180006
0.8047	Intermediate Similarity	NPC473019
0.8045	Intermediate Similarity	NPC103001
0.8036	Intermediate Similarity	NPC70624
0.8034	Intermediate Similarity	NPC141068
0.8034	Intermediate Similarity	NPC473809
0.8033	Intermediate Similarity	NPC298796
0.803	Intermediate Similarity	NPC223616
0.8017	Intermediate Similarity	NPC474364
0.8016	Intermediate Similarity	NPC88403
0.8016	Intermediate Similarity	NPC65041
0.8016	Intermediate Similarity	NPC224657
0.8016	Intermediate Similarity	NPC470858
0.8015	Intermediate Similarity	NPC274876
0.8015	Intermediate Similarity	NPC292998
0.8015	Intermediate Similarity	NPC223354
0.8	Intermediate Similarity	NPC164236
0.8	Intermediate Similarity	NPC308037
0.8	Intermediate Similarity	NPC182646
0.8	Intermediate Similarity	NPC128348
0.8	Intermediate Similarity	NPC313618
0.8	Intermediate Similarity	NPC262359
0.8	Intermediate Similarity	NPC112192
0.8	Intermediate Similarity	NPC64359
0.8	Intermediate Similarity	NPC245219
0.8	Intermediate Similarity	NPC473942
0.8	Intermediate Similarity	NPC472888
0.8	Intermediate Similarity	NPC66384
0.8	Intermediate Similarity	NPC31081
0.8	Intermediate Similarity	NPC309717
0.8	Intermediate Similarity	NPC278556
0.8	Intermediate Similarity	NPC470160
0.8	Intermediate Similarity	NPC189106
0.8	Intermediate Similarity	NPC51345
0.7984	Intermediate Similarity	NPC2989
0.7984	Intermediate Similarity	NPC109778
0.7984	Intermediate Similarity	NPC469929
0.7984	Intermediate Similarity	NPC245395
0.7983	Intermediate Similarity	NPC308744
0.7983	Intermediate Similarity	NPC109241
0.7982	Intermediate Similarity	NPC2518
0.7982	Intermediate Similarity	NPC114594
0.797	Intermediate Similarity	NPC472516
0.797	Intermediate Similarity	NPC254741
0.797	Intermediate Similarity	NPC240593
0.7969	Intermediate Similarity	NPC293453
0.7951	Intermediate Similarity	NPC96705
0.7951	Intermediate Similarity	NPC152306
0.7946	Intermediate Similarity	NPC325497
0.7939	Intermediate Similarity	NPC129132
0.7939	Intermediate Similarity	NPC473655
0.7939	Intermediate Similarity	NPC205468
0.7939	Intermediate Similarity	NPC212631
0.7939	Intermediate Similarity	NPC55147
0.7939	Intermediate Similarity	NPC101294

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 NPC45104 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	291
0.1-0.2	1034
0.2-0.3	1348
0.3-0.4	2541
0.4-0.5	1971
0.5-0.6	1273
0.6-0.7	532
0.7-0.8	142
0.8-0.85	11
0.85-0.9	6
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9008	High Similarity	NPD6832	Phase 2
0.876	High Similarity	NPD1203	Approved
0.8689	High Similarity	NPD1019	Discontinued
0.8667	High Similarity	NPD9717	Approved
0.8651	High Similarity	NPD1899	Clinical (unspecified phase)
0.8583	High Similarity	NPD1547	Clinical (unspecified phase)
0.8547	High Similarity	NPD9493	Approved
0.8504	High Similarity	NPD1933	Approved
0.8448	Intermediate Similarity	NPD1241	Discontinued
0.844	Intermediate Similarity	NPD1238	Approved
0.8425	Intermediate Similarity	NPD4307	Phase 2
0.8306	Intermediate Similarity	NPD3266	Approved
0.8306	Intermediate Similarity	NPD2797	Approved
0.8306	Intermediate Similarity	NPD3267	Approved
0.8244	Intermediate Similarity	NPD1551	Phase 2
0.823	Intermediate Similarity	NPD9697	Approved
0.8214	Intermediate Similarity	NPD9261	Approved
0.8168	Intermediate Similarity	NPD4308	Phase 3
0.8158	Intermediate Similarity	NPD3134	Approved
0.8106	Intermediate Similarity	NPD2935	Discontinued
0.8099	Intermediate Similarity	NPD9545	Approved
0.8095	Intermediate Similarity	NPD2798	Approved
0.8087	Intermediate Similarity	NPD1358	Approved
0.8065	Intermediate Similarity	NPD3972	Approved
0.803	Intermediate Similarity	NPD3748	Approved
0.8	Intermediate Similarity	NPD1240	Approved
0.7984	Intermediate Similarity	NPD411	Approved
0.7984	Intermediate Similarity	NPD2313	Discontinued
0.7984	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7984	Intermediate Similarity	NPD3268	Approved
0.797	Intermediate Similarity	NPD2796	Approved
0.7967	Intermediate Similarity	NPD17	Approved
0.7956	Intermediate Similarity	NPD6799	Approved
0.7951	Intermediate Similarity	NPD1894	Discontinued
0.7939	Intermediate Similarity	NPD447	Suspended
0.7937	Intermediate Similarity	NPD3225	Approved
0.7937	Intermediate Similarity	NPD1876	Approved
0.7931	Intermediate Similarity	NPD9264	Approved
0.7931	Intermediate Similarity	NPD9267	Approved
0.7931	Intermediate Similarity	NPD9263	Approved
0.7926	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD2799	Discontinued
0.7886	Intermediate Similarity	NPD5585	Approved
0.7879	Intermediate Similarity	NPD1607	Approved
0.7863	Intermediate Similarity	NPD74	Approved
0.7863	Intermediate Similarity	NPD9266	Approved
0.784	Intermediate Similarity	NPD1281	Approved
0.7778	Intermediate Similarity	NPD1608	Approved
0.777	Intermediate Similarity	NPD5401	Approved
0.7761	Intermediate Similarity	NPD1510	Phase 2
0.7737	Intermediate Similarity	NPD3750	Approved
0.7737	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1549	Phase 2
0.771	Intermediate Similarity	NPD6798	Discontinued
0.768	Intermediate Similarity	NPD1778	Approved
0.7669	Intermediate Similarity	NPD4618	Approved
0.7669	Intermediate Similarity	NPD4622	Approved
0.7664	Intermediate Similarity	NPD1243	Approved
0.766	Intermediate Similarity	NPD5403	Approved
0.7658	Intermediate Similarity	NPD1202	Approved
0.7656	Intermediate Similarity	NPD1283	Approved
0.7647	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2346	Discontinued
0.7647	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD1481	Phase 2
0.7626	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD6599	Discontinued
0.7609	Intermediate Similarity	NPD4628	Phase 3
0.7609	Intermediate Similarity	NPD7003	Approved
0.7603	Intermediate Similarity	NPD5535	Approved
0.76	Intermediate Similarity	NPD5691	Approved
0.7591	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4359	Approved
0.7576	Intermediate Similarity	NPD1296	Phase 2
0.7569	Intermediate Similarity	NPD7411	Suspended
0.7563	Intermediate Similarity	NPD2182	Approved
0.7559	Intermediate Similarity	NPD1535	Discovery
0.7559	Intermediate Similarity	NPD422	Phase 1
0.7556	Intermediate Similarity	NPD5688	Approved
0.7556	Intermediate Similarity	NPD5689	Approved
0.7554	Intermediate Similarity	NPD3887	Approved
0.7552	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7537	Intermediate Similarity	NPD6355	Discontinued
0.7535	Intermediate Similarity	NPD920	Approved
0.7521	Intermediate Similarity	NPD164	Approved
0.7519	Intermediate Similarity	NPD6233	Phase 2
0.7518	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD2353	Approved
0.748	Intermediate Similarity	NPD3847	Discontinued
0.748	Intermediate Similarity	NPD9281	Approved
0.748	Intermediate Similarity	NPD3496	Discontinued
0.7479	Intermediate Similarity	NPD290	Approved
0.7466	Intermediate Similarity	NPD7819	Suspended
0.7466	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7463	Intermediate Similarity	NPD3140	Approved
0.7463	Intermediate Similarity	NPD3142	Approved
0.7463	Intermediate Similarity	NPD2979	Phase 3
0.7462	Intermediate Similarity	NPD1164	Approved
0.746	Intermediate Similarity	NPD1651	Approved
0.7448	Intermediate Similarity	NPD5889	Approved
0.7448	Intermediate Similarity	NPD5890	Approved
0.7445	Intermediate Similarity	NPD4476	Approved
0.7445	Intermediate Similarity	NPD4477	Approved
0.744	Intermediate Similarity	NPD5536	Phase 2
0.7397	Intermediate Similarity	NPD6801	Discontinued
0.7395	Intermediate Similarity	NPD968	Approved
0.7391	Intermediate Similarity	NPD2344	Approved
0.7388	Intermediate Similarity	NPD4062	Phase 3
0.7388	Intermediate Similarity	NPD520	Approved
0.7376	Intermediate Similarity	NPD7440	Discontinued
0.7372	Intermediate Similarity	NPD7033	Discontinued
0.7365	Intermediate Similarity	NPD7768	Phase 2
0.7348	Intermediate Similarity	NPD9494	Approved
0.7343	Intermediate Similarity	NPD6273	Approved
0.7339	Intermediate Similarity	NPD9257	Approved
0.7339	Intermediate Similarity	NPD9259	Approved
0.7338	Intermediate Similarity	NPD2897	Discontinued
0.7333	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD2366	Approved
0.7319	Intermediate Similarity	NPD2438	Suspended
0.7315	Intermediate Similarity	NPD7075	Discontinued
0.7313	Intermediate Similarity	NPD3764	Approved
0.731	Intermediate Similarity	NPD7458	Discontinued
0.7305	Intermediate Similarity	NPD2354	Approved
0.7297	Intermediate Similarity	NPD5402	Approved
0.7297	Intermediate Similarity	NPD3817	Phase 2
0.7293	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7287	Intermediate Similarity	NPD1611	Approved
0.7279	Intermediate Similarity	NPD230	Phase 1
0.7279	Intermediate Similarity	NPD1184	Approved
0.7273	Intermediate Similarity	NPD4661	Approved
0.7273	Intermediate Similarity	NPD4662	Approved
0.7273	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD4626	Approved
0.726	Intermediate Similarity	NPD6585	Discontinued
0.7244	Intermediate Similarity	NPD1548	Phase 1
0.7236	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5049	Phase 3
0.7218	Intermediate Similarity	NPD454	Approved
0.7194	Intermediate Similarity	NPD2531	Phase 2
0.7192	Intermediate Similarity	NPD3226	Approved
0.7183	Intermediate Similarity	NPD2309	Approved
0.7183	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD2379	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6287	Discontinued
0.7153	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD919	Approved
0.7143	Intermediate Similarity	NPD2557	Approved
0.7143	Intermediate Similarity	NPD1471	Phase 3
0.7143	Intermediate Similarity	NPD4380	Phase 2
0.7133	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD4870	Approved
0.7117	Intermediate Similarity	NPD1282	Approved
0.7113	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6385	Approved
0.7095	Intermediate Similarity	NPD6386	Approved
0.7083	Intermediate Similarity	NPD5909	Discontinued
0.7083	Intermediate Similarity	NPD1237	Approved
0.7083	Intermediate Similarity	NPD1511	Approved
0.708	Intermediate Similarity	NPD9258	Approved
0.708	Intermediate Similarity	NPD9256	Approved
0.7073	Intermediate Similarity	NPD5451	Approved
0.7071	Intermediate Similarity	NPD1501	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4288	Approved
0.7063	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD1934	Approved
0.7045	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD2614	Approved
0.7032	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7023	Intermediate Similarity	NPD1610	Phase 2
0.7021	Intermediate Similarity	NPD6800	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD3882	Suspended
0.7014	Intermediate Similarity	NPD6652	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD6808	Phase 2
0.7008	Intermediate Similarity	NPD709	Approved
0.7007	Intermediate Similarity	NPD8032	Phase 2
0.7	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD196	Phase 1
0.6992	Remote Similarity	NPD2198	Approved
0.6992	Remote Similarity	NPD2199	Approved
0.6992	Remote Similarity	NPD2684	Approved
0.6986	Remote Similarity	NPD2186	Approved
0.6986	Remote Similarity	NPD1512	Approved
0.6985	Remote Similarity	NPD5163	Phase 2
0.6974	Remote Similarity	NPD3749	Approved
0.6974	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD955	Approved
0.6972	Remote Similarity	NPD4534	Discontinued
0.6966	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2651	Approved
0.6959	Remote Similarity	NPD2649	Approved
0.6957	Remote Similarity	NPD4060	Phase 1
0.6954	Remote Similarity	NPD8443	Clinical (unspecified phase)

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data