NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.12
Volume:	214.586
LogP:	3.392
LogD:	4.229
LogS:	-3.583
# Rotatable Bonds:	5
TPSA:	26.3
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	1
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.686
Synthetic Accessibility Score:	1.525
Fsp3:	0.417
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.312
MDCK Permeability:	5.079210677649826e-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.745
Plasma Protein Binding (PPB):	87.8484115600586%
Volume Distribution (VD):	0.639
Pgp-substrate:	13.577847480773926%

ADMET: Metabolism

CYP1A2-inhibitor:	0.948
CYP1A2-substrate:	0.116
CYP2C19-inhibitor:	0.908
CYP2C19-substrate:	0.264
CYP2C9-inhibitor:	0.76
CYP2C9-substrate:	0.333
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.392

ADMET: Excretion

Clearance (CL):	14.175
Half-life (T1/2):	0.852

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.097
Drug-inuced Liver Injury (DILI):	0.777
AMES Toxicity:	0.072
Rat Oral Acute Toxicity:	0.072
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.668
Carcinogencity:	0.484
Eye Corrosion:	0.523
Eye Irritation:	0.979
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: NPC220893

Natural Product ID:	NPC220893
*Common Name:**	Benzyl 3-Methylbutanoate
IUPAC Name:	benzyl 3-methylbutanoate
Synonyms:
Standard InCHIKey:	HVJKZICIMIWFCP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16O2/c1-10(2)8-12(13)14-9-11-6-4-3-5-7-11/h3-7,10H,8-9H2,1-2H3
SMILES:	CC(C)CC(=O)OCc1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3184059
PubChem CID:	7651
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0001097] Benzyloxycarbonyls

*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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26589	Artemisia annua L.	Strain	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
Potency	4

Activity Type	# Activity
Others	4

Target ID	Target Type	Target Name	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	Potency	n.a.	12301.3	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 NPC220893 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	195
0.1-0.2	1226
0.2-0.3	4063
0.3-0.4	11616
0.4-0.5	12570
0.5-0.6	10430
0.6-0.7	2220
0.7-0.8	314
0.8-0.85	39
0.85-0.9	18
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9759	High Similarity	NPC89377
0.9518	High Similarity	NPC58616
0.9302	High Similarity	NPC173443
0.9186	High Similarity	NPC304760
0.9048	High Similarity	NPC270507
0.9022	High Similarity	NPC146351
0.8929	High Similarity	NPC103387
0.8929	High Similarity	NPC323103
0.8913	High Similarity	NPC225060
0.8913	High Similarity	NPC78701
0.8913	High Similarity	NPC35448
0.8804	High Similarity	NPC276775
0.8804	High Similarity	NPC92754
0.8804	High Similarity	NPC249912
0.869	High Similarity	NPC121800
0.8667	High Similarity	NPC119631
0.8587	High Similarity	NPC130398
0.8571	High Similarity	NPC170484
0.8542	High Similarity	NPC474365
0.8542	High Similarity	NPC301943
0.8526	High Similarity	NPC70624
0.8488	Intermediate Similarity	NPC106313
0.8434	Intermediate Similarity	NPC175393
0.8421	Intermediate Similarity	NPC325497
0.8421	Intermediate Similarity	NPC118343
0.8409	Intermediate Similarity	NPC294134
0.8404	Intermediate Similarity	NPC325499
0.8372	Intermediate Similarity	NPC303245
0.8372	Intermediate Similarity	NPC165212
0.8352	Intermediate Similarity	NPC240108
0.8352	Intermediate Similarity	NPC213156
0.8333	Intermediate Similarity	NPC42211
0.8247	Intermediate Similarity	NPC188895
0.8229	Intermediate Similarity	NPC203925
0.8218	Intermediate Similarity	NPC214067
0.8218	Intermediate Similarity	NPC196246
0.82	Intermediate Similarity	NPC56493
0.8182	Intermediate Similarity	NPC269457
0.8182	Intermediate Similarity	NPC288903
0.8152	Intermediate Similarity	NPC185501
0.814	Intermediate Similarity	NPC78517
0.814	Intermediate Similarity	NPC167577
0.8137	Intermediate Similarity	NPC1082
0.8137	Intermediate Similarity	NPC305912
0.8119	Intermediate Similarity	NPC469636
0.8119	Intermediate Similarity	NPC17417
0.8119	Intermediate Similarity	NPC10251
0.81	Intermediate Similarity	NPC119271
0.8085	Intermediate Similarity	NPC23453
0.8058	Intermediate Similarity	NPC270699
0.8058	Intermediate Similarity	NPC82899
0.8043	Intermediate Similarity	NPC9822
0.8041	Intermediate Similarity	NPC98911
0.8041	Intermediate Similarity	NPC472318
0.8039	Intermediate Similarity	NPC174099
0.8039	Intermediate Similarity	NPC251854
0.8039	Intermediate Similarity	NPC93084
0.8023	Intermediate Similarity	NPC176228
0.8022	Intermediate Similarity	NPC96625
0.8021	Intermediate Similarity	NPC270654
0.8	Intermediate Similarity	NPC5472
0.8	Intermediate Similarity	NPC473855
0.8	Intermediate Similarity	NPC238115
0.7981	Intermediate Similarity	NPC128368
0.798	Intermediate Similarity	NPC89886
0.798	Intermediate Similarity	NPC234305
0.7961	Intermediate Similarity	NPC474157
0.7961	Intermediate Similarity	NPC476003
0.7955	Intermediate Similarity	NPC89950
0.7941	Intermediate Similarity	NPC83628
0.7941	Intermediate Similarity	NPC474364
0.7941	Intermediate Similarity	NPC265407
0.7921	Intermediate Similarity	NPC475203
0.7921	Intermediate Similarity	NPC472316
0.7921	Intermediate Similarity	NPC472315
0.7921	Intermediate Similarity	NPC326447
0.7921	Intermediate Similarity	NPC474376
0.7907	Intermediate Similarity	NPC287790
0.7907	Intermediate Similarity	NPC3672
0.7905	Intermediate Similarity	NPC153053
0.79	Intermediate Similarity	NPC85977
0.79	Intermediate Similarity	NPC31786
0.7885	Intermediate Similarity	NPC321852
0.7857	Intermediate Similarity	NPC171843
0.783	Intermediate Similarity	NPC210092
0.7826	Intermediate Similarity	NPC169050
0.7826	Intermediate Similarity	NPC286608
0.7822	Intermediate Similarity	NPC209632
0.7802	Intermediate Similarity	NPC53299
0.7802	Intermediate Similarity	NPC475710
0.78	Intermediate Similarity	NPC60679
0.78	Intermediate Similarity	NPC160382
0.78	Intermediate Similarity	NPC179686
0.7788	Intermediate Similarity	NPC260818
0.7788	Intermediate Similarity	NPC210089
0.7778	Intermediate Similarity	NPC324835
0.7778	Intermediate Similarity	NPC208183
0.7778	Intermediate Similarity	NPC243289
0.7778	Intermediate Similarity	NPC308619
0.7778	Intermediate Similarity	NPC127491
0.7767	Intermediate Similarity	NPC469511
0.7745	Intermediate Similarity	NPC37622
0.7745	Intermediate Similarity	NPC176971
0.7745	Intermediate Similarity	NPC30594
0.7745	Intermediate Similarity	NPC1065
0.7745	Intermediate Similarity	NPC136962
0.7736	Intermediate Similarity	NPC190212
0.7736	Intermediate Similarity	NPC474363
0.7736	Intermediate Similarity	NPC307651
0.7723	Intermediate Similarity	NPC114594
0.7723	Intermediate Similarity	NPC283546
0.7717	Intermediate Similarity	NPC318107
0.77	Intermediate Similarity	NPC45613
0.7692	Intermediate Similarity	NPC273837
0.767	Intermediate Similarity	NPC157473
0.767	Intermediate Similarity	NPC151530
0.7667	Intermediate Similarity	NPC99240
0.7647	Intermediate Similarity	NPC128730
0.7647	Intermediate Similarity	NPC472919
0.7642	Intermediate Similarity	NPC26615
0.7642	Intermediate Similarity	NPC272524
0.7642	Intermediate Similarity	NPC161611
0.7634	Intermediate Similarity	NPC322387
0.7624	Intermediate Similarity	NPC82426
0.7624	Intermediate Similarity	NPC304638
0.7624	Intermediate Similarity	NPC91820
0.7619	Intermediate Similarity	NPC167504
0.7615	Intermediate Similarity	NPC45794
0.7604	Intermediate Similarity	NPC77273
0.76	Intermediate Similarity	NPC107101
0.76	Intermediate Similarity	NPC469481
0.7596	Intermediate Similarity	NPC85493
0.7596	Intermediate Similarity	NPC269023
0.7596	Intermediate Similarity	NPC99846
0.7596	Intermediate Similarity	NPC31274
0.7596	Intermediate Similarity	NPC291837
0.7582	Intermediate Similarity	NPC285773
0.7579	Intermediate Similarity	NPC70940
0.7579	Intermediate Similarity	NPC84288
0.7579	Intermediate Similarity	NPC274455
0.7579	Intermediate Similarity	NPC86670
0.7576	Intermediate Similarity	NPC175852
0.7576	Intermediate Similarity	NPC475954
0.7576	Intermediate Similarity	NPC210529
0.7576	Intermediate Similarity	NPC160548
0.7573	Intermediate Similarity	NPC477251
0.757	Intermediate Similarity	NPC308744
0.7549	Intermediate Similarity	NPC280616
0.7549	Intermediate Similarity	NPC171831
0.7549	Intermediate Similarity	NPC242913
0.7549	Intermediate Similarity	NPC109637
0.7547	Intermediate Similarity	NPC474314
0.7547	Intermediate Similarity	NPC158282
0.7547	Intermediate Similarity	NPC79496
0.7545	Intermediate Similarity	NPC254233
0.7545	Intermediate Similarity	NPC293424
0.7526	Intermediate Similarity	NPC261181
0.7525	Intermediate Similarity	NPC307425
0.7524	Intermediate Similarity	NPC234639
0.7524	Intermediate Similarity	NPC259554
0.75	Intermediate Similarity	NPC221275
0.75	Intermediate Similarity	NPC474685
0.75	Intermediate Similarity	NPC66655
0.75	Intermediate Similarity	NPC277788
0.75	Intermediate Similarity	NPC304538
0.7477	Intermediate Similarity	NPC474176
0.7477	Intermediate Similarity	NPC234956
0.7476	Intermediate Similarity	NPC227255
0.7476	Intermediate Similarity	NPC473393
0.7475	Intermediate Similarity	NPC253423
0.7473	Intermediate Similarity	NPC329319
0.7473	Intermediate Similarity	NPC103326
0.7473	Intermediate Similarity	NPC87299
0.7473	Intermediate Similarity	NPC99394
0.7453	Intermediate Similarity	NPC25067
0.7453	Intermediate Similarity	NPC231251
0.7453	Intermediate Similarity	NPC88868
0.7451	Intermediate Similarity	NPC298224
0.7444	Intermediate Similarity	NPC328178
0.7444	Intermediate Similarity	NPC127343
0.7431	Intermediate Similarity	NPC149691
0.7431	Intermediate Similarity	NPC216387
0.7429	Intermediate Similarity	NPC206341
0.7426	Intermediate Similarity	NPC253746
0.7411	Intermediate Similarity	NPC476183
0.7411	Intermediate Similarity	NPC72977
0.7411	Intermediate Similarity	NPC473243
0.7407	Intermediate Similarity	NPC109241
0.7407	Intermediate Similarity	NPC172525
0.7404	Intermediate Similarity	NPC37115
0.74	Intermediate Similarity	NPC229242
0.7396	Intermediate Similarity	NPC62765
0.7391	Intermediate Similarity	NPC44830
0.7391	Intermediate Similarity	NPC172984
0.7387	Intermediate Similarity	NPC159916
0.7379	Intermediate Similarity	NPC2518
0.7379	Intermediate Similarity	NPC38209
0.7368	Intermediate Similarity	NPC329064
0.7364	Intermediate Similarity	NPC190298
0.7363	Intermediate Similarity	NPC117180

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 NPC220893 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	892
0.2-0.3	1324
0.3-0.4	3091
0.4-0.5	2112
0.5-0.6	1158
0.6-0.7	345
0.7-0.8	56
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8421	Intermediate Similarity	NPD1238	Approved
0.8119	Intermediate Similarity	NPD2182	Approved
0.7961	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7957	Intermediate Similarity	NPD3673	Approved
0.7957	Intermediate Similarity	NPD3672	Approved
0.7921	Intermediate Similarity	NPD3134	Approved
0.79	Intermediate Similarity	NPD164	Approved
0.7826	Intermediate Similarity	NPD1282	Approved
0.7826	Intermediate Similarity	NPD1087	Approved
0.7755	Intermediate Similarity	NPD5926	Approved
0.7732	Intermediate Similarity	NPD1989	Approved
0.7727	Intermediate Similarity	NPD9490	Approved
0.7717	Intermediate Similarity	NPD9257	Approved
0.7717	Intermediate Similarity	NPD9259	Approved
0.7692	Intermediate Similarity	NPD5235	Approved
0.7692	Intermediate Similarity	NPD5237	Approved
0.7692	Intermediate Similarity	NPD5240	Approved
0.7692	Intermediate Similarity	NPD5236	Approved
0.7692	Intermediate Similarity	NPD5239	Approved
0.767	Intermediate Similarity	NPD1358	Approved
0.766	Intermediate Similarity	NPD800	Approved
0.7619	Intermediate Similarity	NPD2201	Approved
0.7614	Intermediate Similarity	NPD225	Approved
0.7614	Intermediate Similarity	NPD227	Approved
0.7582	Intermediate Similarity	NPD9491	Approved
0.7579	Intermediate Similarity	NPD1086	Approved
0.7579	Intermediate Similarity	NPD1090	Approved
0.7579	Intermediate Similarity	NPD1089	Approved
0.7576	Intermediate Similarity	NPD9495	Approved
0.7526	Intermediate Similarity	NPD1202	Approved
0.7524	Intermediate Similarity	NPD2067	Discontinued
0.75	Intermediate Similarity	NPD9294	Approved
0.7477	Intermediate Similarity	NPD5585	Approved
0.7451	Intermediate Similarity	NPD6647	Phase 2
0.7431	Intermediate Similarity	NPD4198	Discontinued
0.7423	Intermediate Similarity	NPD1088	Approved
0.7396	Intermediate Similarity	NPD9256	Approved
0.7396	Intermediate Similarity	NPD9258	Approved
0.7379	Intermediate Similarity	NPD5909	Discontinued
0.7363	Intermediate Similarity	NPD226	Approved
0.7339	Intermediate Similarity	NPD2629	Approved
0.7292	Intermediate Similarity	NPD5346	Phase 2
0.7292	Intermediate Similarity	NPD5347	Phase 2
0.7292	Intermediate Similarity	NPD689	Discontinued
0.7273	Intermediate Similarity	NPD1693	Approved
0.7257	Intermediate Similarity	NPD1778	Approved
0.7255	Intermediate Similarity	NPD2549	Approved
0.7255	Intermediate Similarity	NPD2553	Approved
0.7255	Intermediate Similarity	NPD2558	Approved
0.7255	Intermediate Similarity	NPD2555	Approved
0.7255	Intermediate Similarity	NPD2550	Approved
0.7255	Intermediate Similarity	NPD2552	Approved
0.7232	Intermediate Similarity	NPD9545	Approved
0.7222	Intermediate Similarity	NPD969	Suspended
0.7207	Intermediate Similarity	NPD5292	Approved
0.7207	Intermediate Similarity	NPD5291	Approved
0.7184	Intermediate Similarity	NPD4189	Approved
0.7184	Intermediate Similarity	NPD4188	Approved
0.7182	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD9250	Approved
0.7172	Intermediate Similarity	NPD1563	Approved
0.7172	Intermediate Similarity	NPD1066	Discontinued
0.7156	Intermediate Similarity	NPD5535	Approved
0.7155	Intermediate Similarity	NPD4359	Approved
0.7143	Intermediate Similarity	NPD9697	Approved
0.7115	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD9260	Approved
0.7091	Intermediate Similarity	NPD1241	Discontinued
0.7083	Intermediate Similarity	NPD4793	Discontinued
0.708	Intermediate Similarity	NPD1894	Discontinued
0.7079	Intermediate Similarity	NPD9716	Approved
0.7054	Intermediate Similarity	NPD9493	Approved
0.7048	Intermediate Similarity	NPD3048	Approved
0.7048	Intermediate Similarity	NPD3046	Approved
0.7048	Intermediate Similarity	NPD3047	Approved
0.7018	Intermediate Similarity	NPD5691	Approved
0.7	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.699	Remote Similarity	NPD7798	Approved
0.699	Remote Similarity	NPD2066	Phase 3
0.6983	Remote Similarity	NPD6287	Discontinued
0.6983	Remote Similarity	NPD4480	Approved
0.6981	Remote Similarity	NPD794	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1239	Approved
0.6961	Remote Similarity	NPD1564	Approved
0.6961	Remote Similarity	NPD1565	Approved
0.6961	Remote Similarity	NPD1566	Phase 3
0.6957	Remote Similarity	NPD5306	Approved
0.6957	Remote Similarity	NPD5305	Approved
0.6957	Remote Similarity	NPD17	Approved
0.6949	Remote Similarity	NPD2198	Approved
0.6949	Remote Similarity	NPD5667	Approved
0.6949	Remote Similarity	NPD2199	Approved
0.6944	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD2684	Approved
0.6916	Remote Similarity	NPD812	Approved
0.6916	Remote Similarity	NPD810	Approved
0.6916	Remote Similarity	NPD3524	Approved
0.6916	Remote Similarity	NPD3526	Approved
0.6916	Remote Similarity	NPD2559	Approved
0.6916	Remote Similarity	NPD2551	Approved
0.6916	Remote Similarity	NPD811	Approved
0.6916	Remote Similarity	NPD6685	Approved
0.6909	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD3496	Discontinued
0.6897	Remote Similarity	NPD3847	Discontinued
0.6881	Remote Similarity	NPD1752	Approved
0.6881	Remote Similarity	NPD4233	Approved
0.6881	Remote Similarity	NPD1756	Approved
0.6881	Remote Similarity	NPD4234	Approved
0.6852	Remote Similarity	NPD290	Approved
0.6842	Remote Similarity	NPD2347	Approved
0.6842	Remote Similarity	NPD3971	Phase 1
0.6838	Remote Similarity	NPD4806	Approved
0.6838	Remote Similarity	NPD1281	Approved
0.6838	Remote Similarity	NPD4807	Approved
0.6837	Remote Similarity	NPD531	Approved
0.6833	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6085	Phase 2
0.6827	Remote Similarity	NPD9712	Approved
0.6822	Remote Similarity	NPD5048	Discontinued
0.681	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2650	Approved
0.6786	Remote Similarity	NPD6010	Discontinued
0.6786	Remote Similarity	NPD2652	Approved
0.678	Remote Similarity	NPD1608	Approved
0.678	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6759	Remote Similarity	NPD5705	Approved
0.6759	Remote Similarity	NPD5704	Approved
0.6759	Remote Similarity	NPD5706	Approved
0.6759	Remote Similarity	NPD968	Approved
0.6757	Remote Similarity	NPD1139	Approved
0.6757	Remote Similarity	NPD1137	Approved
0.6752	Remote Similarity	NPD4135	Approved
0.6752	Remote Similarity	NPD4136	Approved
0.6752	Remote Similarity	NPD4106	Approved
0.675	Remote Similarity	NPD552	Approved
0.675	Remote Similarity	NPD9567	Approved
0.675	Remote Similarity	NPD2797	Approved
0.675	Remote Similarity	NPD6362	Approved
0.675	Remote Similarity	NPD553	Approved
0.6731	Remote Similarity	NPD9711	Approved
0.6731	Remote Similarity	NPD9710	Approved
0.6729	Remote Similarity	NPD1237	Approved
0.6727	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4766	Approved
0.6721	Remote Similarity	NPD6832	Phase 2
0.6701	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.6696	Remote Similarity	NPD821	Approved
0.6696	Remote Similarity	NPD2607	Approved
0.6696	Remote Similarity	NPD1138	Approved
0.6696	Remote Similarity	NPD7843	Approved
0.6696	Remote Similarity	NPD5277	Phase 2
0.6695	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD1019	Discontinued
0.6694	Remote Similarity	NPD4870	Approved
0.6667	Remote Similarity	NPD845	Approved
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD4626	Approved
0.6667	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.664	Remote Similarity	NPD2979	Phase 3
0.6639	Remote Similarity	NPD4006	Discontinued
0.6639	Remote Similarity	NPD9717	Approved
0.6636	Remote Similarity	NPD1930	Approved
0.6636	Remote Similarity	NPD9261	Approved
0.6636	Remote Similarity	NPD1929	Approved
0.6636	Remote Similarity	NPD5765	Approved
0.6636	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6613	Remote Similarity	NPD6798	Discontinued
0.6612	Remote Similarity	NPD3267	Approved
0.6612	Remote Similarity	NPD3266	Approved
0.6609	Remote Similarity	NPD4576	Approved
0.6609	Remote Similarity	NPD4574	Approved
0.6607	Remote Similarity	NPD4573	Approved
0.6607	Remote Similarity	NPD4571	Approved
0.6607	Remote Similarity	NPD4572	Approved
0.6602	Remote Similarity	NPD2934	Approved
0.6602	Remote Similarity	NPD2933	Approved
0.66	Remote Similarity	NPD9249	Phase 1
0.6587	Remote Similarity	NPD4622	Approved
0.6587	Remote Similarity	NPD4618	Approved
0.6587	Remote Similarity	NPD6355	Discontinued
0.6581	Remote Similarity	NPD4102	Approved
0.6581	Remote Similarity	NPD1651	Approved
0.6581	Remote Similarity	NPD4105	Approved
0.6579	Remote Similarity	NPD5951	Approved
0.6577	Remote Similarity	NPD5451	Approved
0.6577	Remote Similarity	NPD551	Approved
0.6577	Remote Similarity	NPD550	Approved
0.656	Remote Similarity	NPD4062	Phase 3
0.656	Remote Similarity	NPD6233	Phase 2
0.6557	Remote Similarity	NPD5647	Approved
0.6555	Remote Similarity	NPD5338	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD1535	Discovery
0.6552	Remote Similarity	NPD5536	Phase 2
0.6549	Remote Similarity	NPD6858	Approved
0.6549	Remote Similarity	NPD2497	Approved
0.6549	Remote Similarity	NPD2496	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