NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	192.12
Volume:	214.586
LogP:	3.793
LogD:	4.157
LogS:	-3.979
# 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:	1.475
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:	-4.221
MDCK Permeability:	3.249342626077123e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.965

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	96.19575500488281%
Volume Distribution (VD):	1.519
Pgp-substrate:	4.065896987915039%

ADMET: Metabolism

CYP1A2-inhibitor:	0.964
CYP1A2-substrate:	0.388
CYP2C19-inhibitor:	0.915
CYP2C19-substrate:	0.187
CYP2C9-inhibitor:	0.819
CYP2C9-substrate:	0.699
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.091
CYP3A4-inhibitor:	0.038
CYP3A4-substrate:	0.197

ADMET: Excretion

Clearance (CL):	12.198
Half-life (T1/2):	0.705

ADMET: Toxicity

hERG Blockers:	0.068
Human Hepatotoxicity (H-HT):	0.012
Drug-inuced Liver Injury (DILI):	0.351
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.009
Skin Sensitization:	0.591
Carcinogencity:	0.118
Eye Corrosion:	0.217
Eye Irritation:	0.991
Respiratory Toxicity:	0.102

Download Data

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

Natural Product: NPC146351

Natural Product ID:	NPC146351
*Common Name:**	Benzoic Acid 1-(3-Methyl)Butyl Ester
IUPAC Name:	3-methylbutyl benzoate
Synonyms:
Standard InCHIKey:	MLLAPOCBLWUFAP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C12H16O2/c1-10(2)8-9-14-12(13)11-6-4-3-5-7-11/h3-7,10H,8-9H2,1-2H3
SMILES:	CC(C)CCOC(=O)c1ccccc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2260711
PubChem CID:	7193
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
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	branch	n.a.	PMID[17202693]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21458	Radix paeoniae rubra	Species	Lymnaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11291	Styrax benzoin	Species	Styracaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15095	Hippophae rhamnoides	Species	Elaeagnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11291	Styrax benzoin	Species	Styracaceae	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
Others	1
Potency	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Potency	n.a.	54954.4	nM	PubChem BioAssay data set
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	pLD50	=	8.75	n.a.	PMID[557445]

☑ 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 NPC146351 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	225
0.1-0.2	1513
0.2-0.3	3888
0.3-0.4	9942
0.4-0.5	11078
0.5-0.6	11416
0.6-0.7	4003
0.7-0.8	517
0.8-0.85	53
0.85-0.9	36
0.9-0.95	15
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
0.9891	High Similarity	NPC78701
0.9891	High Similarity	NPC35448
0.9891	High Similarity	NPC225060
0.9783	High Similarity	NPC92754
0.9783	High Similarity	NPC276775
0.9783	High Similarity	NPC249912
0.9565	High Similarity	NPC130398
0.9479	High Similarity	NPC474365
0.9479	High Similarity	NPC301943
0.9474	High Similarity	NPC70624
0.9368	High Similarity	NPC325497
0.9368	High Similarity	NPC118343
0.9271	High Similarity	NPC42211
0.9175	High Similarity	NPC188895
0.9167	High Similarity	NPC203925
0.9109	High Similarity	NPC196246
0.9109	High Similarity	NPC214067
0.91	High Similarity	NPC56493
0.9091	High Similarity	NPC269457
0.9022	High Similarity	NPC173443
0.9022	High Similarity	NPC220893
0.902	High Similarity	NPC1082
0.902	High Similarity	NPC305912
0.901	High Similarity	NPC17417
0.901	High Similarity	NPC10251
0.901	High Similarity	NPC469636
0.9	High Similarity	NPC119271
0.8932	High Similarity	NPC270699
0.8932	High Similarity	NPC82899
0.8922	High Similarity	NPC251854
0.8922	High Similarity	NPC174099
0.8922	High Similarity	NPC93084
0.8889	High Similarity	NPC89886
0.8846	High Similarity	NPC128368
0.8835	High Similarity	NPC476003
0.8835	High Similarity	NPC474157
0.8824	High Similarity	NPC83628
0.8824	High Similarity	NPC474364
0.8824	High Similarity	NPC265407
0.8804	High Similarity	NPC89377
0.88	High Similarity	NPC31786
0.8762	High Similarity	NPC153053
0.875	High Similarity	NPC321852
0.8713	High Similarity	NPC209632
0.87	High Similarity	NPC60679
0.8696	High Similarity	NPC318107
0.8679	High Similarity	NPC210092
0.8654	High Similarity	NPC260818
0.8654	High Similarity	NPC210089
0.8627	High Similarity	NPC30594
0.8627	High Similarity	NPC37622
0.8614	High Similarity	NPC114594
0.86	High Similarity	NPC45613
0.8587	High Similarity	NPC58616
0.8585	High Similarity	NPC307651
0.8585	High Similarity	NPC474363
0.8491	Intermediate Similarity	NPC161611
0.8491	Intermediate Similarity	NPC272524
0.8476	Intermediate Similarity	NPC167504
0.8462	Intermediate Similarity	NPC85493
0.8462	Intermediate Similarity	NPC99846
0.8462	Intermediate Similarity	NPC269023
0.8454	Intermediate Similarity	NPC261181
0.8438	Intermediate Similarity	NPC119631
0.8411	Intermediate Similarity	NPC308744
0.8396	Intermediate Similarity	NPC158282
0.8396	Intermediate Similarity	NPC79496
0.8396	Intermediate Similarity	NPC474314
0.8387	Intermediate Similarity	NPC294134
0.8384	Intermediate Similarity	NPC270654
0.8384	Intermediate Similarity	NPC253423
0.8333	Intermediate Similarity	NPC474685
0.8333	Intermediate Similarity	NPC62765
0.8318	Intermediate Similarity	NPC474176
0.8316	Intermediate Similarity	NPC304760
0.83	Intermediate Similarity	NPC229242
0.8257	Intermediate Similarity	NPC149691
0.8235	Intermediate Similarity	NPC304873
0.8218	Intermediate Similarity	NPC217621
0.8214	Intermediate Similarity	NPC72977
0.8214	Intermediate Similarity	NPC473243
0.8172	Intermediate Similarity	NPC288903
0.8172	Intermediate Similarity	NPC270507
0.8165	Intermediate Similarity	NPC306740
0.8152	Intermediate Similarity	NPC303245
0.8144	Intermediate Similarity	NPC213156
0.8144	Intermediate Similarity	NPC240108
0.8142	Intermediate Similarity	NPC50872
0.8137	Intermediate Similarity	NPC473325
0.8125	Intermediate Similarity	NPC90522
0.8125	Intermediate Similarity	NPC328459
0.8108	Intermediate Similarity	NPC45104
0.8108	Intermediate Similarity	NPC217423
0.8108	Intermediate Similarity	NPC469574
0.81	Intermediate Similarity	NPC61944
0.8091	Intermediate Similarity	NPC100353
0.8073	Intermediate Similarity	NPC237366
0.8065	Intermediate Similarity	NPC103387
0.8065	Intermediate Similarity	NPC323103
0.8058	Intermediate Similarity	NPC25458
0.8041	Intermediate Similarity	NPC9822
0.8036	Intermediate Similarity	NPC94298
0.8036	Intermediate Similarity	NPC27633
0.8036	Intermediate Similarity	NPC94637
0.8	Intermediate Similarity	NPC81808
0.8	Intermediate Similarity	NPC474095
0.798	Intermediate Similarity	NPC77273
0.7963	Intermediate Similarity	NPC243355
0.7935	Intermediate Similarity	NPC78517
0.7935	Intermediate Similarity	NPC167577
0.7928	Intermediate Similarity	NPC220540
0.7928	Intermediate Similarity	NPC188907
0.7913	Intermediate Similarity	NPC26285
0.7909	Intermediate Similarity	NPC477411
0.7909	Intermediate Similarity	NPC196075
0.7885	Intermediate Similarity	NPC284477
0.7876	Intermediate Similarity	NPC293424
0.7864	Intermediate Similarity	NPC228435
0.7864	Intermediate Similarity	NPC98911
0.7864	Intermediate Similarity	NPC472318
0.7857	Intermediate Similarity	NPC128825
0.7857	Intermediate Similarity	NPC131192
0.785	Intermediate Similarity	NPC470391
0.785	Intermediate Similarity	NPC249811
0.7849	Intermediate Similarity	NPC121800
0.7845	Intermediate Similarity	NPC472703
0.783	Intermediate Similarity	NPC105899
0.7826	Intermediate Similarity	NPC176228
0.781	Intermediate Similarity	NPC160382
0.781	Intermediate Similarity	NPC234305
0.781	Intermediate Similarity	NPC255676
0.7797	Intermediate Similarity	NPC476599
0.7797	Intermediate Similarity	NPC275576
0.7797	Intermediate Similarity	NPC49938
0.7797	Intermediate Similarity	NPC470765
0.7788	Intermediate Similarity	NPC282895
0.7788	Intermediate Similarity	NPC240664
0.7778	Intermediate Similarity	NPC185501
0.7778	Intermediate Similarity	NPC472704
0.7768	Intermediate Similarity	NPC135730
0.7768	Intermediate Similarity	NPC226093
0.7766	Intermediate Similarity	NPC89950
0.7757	Intermediate Similarity	NPC1065
0.7757	Intermediate Similarity	NPC474376
0.7757	Intermediate Similarity	NPC475203
0.7757	Intermediate Similarity	NPC326447
0.7757	Intermediate Similarity	NPC472315
0.7757	Intermediate Similarity	NPC472316
0.7748	Intermediate Similarity	NPC53953
0.7742	Intermediate Similarity	NPC170484
0.7739	Intermediate Similarity	NPC233282
0.7739	Intermediate Similarity	NPC230951
0.7736	Intermediate Similarity	NPC85977
0.7731	Intermediate Similarity	NPC169913
0.7731	Intermediate Similarity	NPC470753
0.7731	Intermediate Similarity	NPC473220
0.7727	Intermediate Similarity	NPC212415
0.7727	Intermediate Similarity	NPC23332
0.7727	Intermediate Similarity	NPC57879
0.7727	Intermediate Similarity	NPC54626
0.7727	Intermediate Similarity	NPC66208
0.7723	Intermediate Similarity	NPC23453
0.7717	Intermediate Similarity	NPC3672
0.7717	Intermediate Similarity	NPC287790
0.7712	Intermediate Similarity	NPC295664
0.7712	Intermediate Similarity	NPC221798
0.7712	Intermediate Similarity	NPC246166
0.7712	Intermediate Similarity	NPC184219
0.7712	Intermediate Similarity	NPC125053
0.77	Intermediate Similarity	NPC110704
0.7699	Intermediate Similarity	NPC470860
0.7692	Intermediate Similarity	NPC291189
0.7692	Intermediate Similarity	NPC69403
0.7692	Intermediate Similarity	NPC223351
0.7684	Intermediate Similarity	NPC106313
0.7679	Intermediate Similarity	NPC252004
0.7679	Intermediate Similarity	NPC228936
0.767	Intermediate Similarity	NPC325499
0.7658	Intermediate Similarity	NPC17693
0.7658	Intermediate Similarity	NPC13784
0.7653	Intermediate Similarity	NPC96625
0.7653	Intermediate Similarity	NPC322387
0.7652	Intermediate Similarity	NPC61779
0.7652	Intermediate Similarity	NPC204784
0.7647	Intermediate Similarity	NPC5472
0.7642	Intermediate Similarity	NPC179686
0.7636	Intermediate Similarity	NPC183648
0.7632	Intermediate Similarity	NPC228318
0.7615	Intermediate Similarity	NPC40178
0.7615	Intermediate Similarity	NPC281604
0.7609	Intermediate Similarity	NPC175393
0.7604	Intermediate Similarity	NPC127491
0.7604	Intermediate Similarity	NPC208183
0.7604	Intermediate Similarity	NPC308619
0.7604	Intermediate Similarity	NPC324835
0.7604	Intermediate Similarity	NPC243289
0.7604	Intermediate Similarity	NPC285773
0.76	Intermediate Similarity	NPC274455
0.76	Intermediate Similarity	NPC70940
0.76	Intermediate Similarity	NPC86670

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 NPC146351 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	213
0.1-0.2	937
0.2-0.3	1284
0.3-0.4	2912
0.4-0.5	2285
0.5-0.6	1099
0.6-0.7	344
0.7-0.8	66
0.8-0.85	4
0.85-0.9	5
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9368	High Similarity	NPD1238	Approved
0.901	High Similarity	NPD2182	Approved
0.8835	High Similarity	NPD2181	Clinical (unspecified phase)
0.88	High Similarity	NPD164	Approved
0.8696	High Similarity	NPD9257	Approved
0.8696	High Similarity	NPD9259	Approved
0.8454	Intermediate Similarity	NPD1202	Approved
0.8333	Intermediate Similarity	NPD9256	Approved
0.8333	Intermediate Similarity	NPD9258	Approved
0.8036	Intermediate Similarity	NPD9545	Approved
0.8	Intermediate Similarity	NPD9260	Approved
0.7857	Intermediate Similarity	NPD9493	Approved
0.7835	Intermediate Similarity	NPD1087	Approved
0.7778	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD3673	Approved
0.7778	Intermediate Similarity	NPD3672	Approved
0.7759	Intermediate Similarity	NPD6287	Discontinued
0.7757	Intermediate Similarity	NPD3134	Approved
0.7745	Intermediate Similarity	NPD1989	Approved
0.7742	Intermediate Similarity	NPD9490	Approved
0.7727	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD2198	Approved
0.7712	Intermediate Similarity	NPD2199	Approved
0.7706	Intermediate Similarity	NPD2067	Discontinued
0.7679	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD800	Approved
0.7604	Intermediate Similarity	NPD9491	Approved
0.76	Intermediate Similarity	NPD1086	Approved
0.76	Intermediate Similarity	NPD1089	Approved
0.76	Intermediate Similarity	NPD1090	Approved
0.7596	Intermediate Similarity	NPD9495	Approved
0.7589	Intermediate Similarity	NPD1241	Discontinued
0.757	Intermediate Similarity	NPD5909	Discontinued
0.757	Intermediate Similarity	NPD1237	Approved
0.7524	Intermediate Similarity	NPD2066	Phase 3
0.7523	Intermediate Similarity	NPD1358	Approved
0.75	Intermediate Similarity	NPD5277	Phase 2
0.75	Intermediate Similarity	NPD9567	Approved
0.75	Intermediate Similarity	NPD552	Approved
0.75	Intermediate Similarity	NPD553	Approved
0.7477	Intermediate Similarity	NPD1929	Approved
0.7477	Intermediate Similarity	NPD1930	Approved
0.7477	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7477	Intermediate Similarity	NPD6647	Phase 2
0.7477	Intermediate Similarity	NPD9261	Approved
0.7475	Intermediate Similarity	NPD1282	Approved
0.7459	Intermediate Similarity	NPD6832	Phase 2
0.7458	Intermediate Similarity	NPD518	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD1088	Approved
0.7447	Intermediate Similarity	NPD227	Approved
0.7447	Intermediate Similarity	NPD225	Approved
0.7438	Intermediate Similarity	NPD1019	Discontinued
0.7436	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5926	Approved
0.7398	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7395	Intermediate Similarity	NPD9717	Approved
0.7368	Intermediate Similarity	NPD5951	Approved
0.7368	Intermediate Similarity	NPD2629	Approved
0.7308	Intermediate Similarity	NPD1693	Approved
0.7258	Intermediate Similarity	NPD7008	Discontinued
0.7257	Intermediate Similarity	NPD9508	Approved
0.7222	Intermediate Similarity	NPD3373	Approved
0.7216	Intermediate Similarity	NPD226	Approved
0.7212	Intermediate Similarity	NPD1563	Approved
0.7212	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD9267	Approved
0.7207	Intermediate Similarity	NPD9263	Approved
0.7207	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7207	Intermediate Similarity	NPD9264	Approved
0.7188	Intermediate Similarity	NPD2567	Approved
0.7188	Intermediate Similarity	NPD2670	Approved
0.7188	Intermediate Similarity	NPD2569	Approved
0.7179	Intermediate Similarity	NPD2347	Approved
0.7167	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD5346	Phase 2
0.7157	Intermediate Similarity	NPD5347	Phase 2
0.7154	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD74	Approved
0.7143	Intermediate Similarity	NPD9266	Approved
0.712	Intermediate Similarity	NPD6039	Approved
0.7107	Intermediate Similarity	NPD3972	Approved
0.708	Intermediate Similarity	NPD5239	Approved
0.708	Intermediate Similarity	NPD5240	Approved
0.708	Intermediate Similarity	NPD5236	Approved
0.708	Intermediate Similarity	NPD5235	Approved
0.708	Intermediate Similarity	NPD5237	Approved
0.7073	Intermediate Similarity	NPD1203	Approved
0.7059	Intermediate Similarity	NPD5585	Approved
0.7031	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD9697	Approved
0.7019	Intermediate Similarity	NPD1239	Approved
0.7018	Intermediate Similarity	NPD2201	Approved
0.7016	Intermediate Similarity	NPD2798	Approved
0.7009	Intermediate Similarity	NPD1564	Approved
0.7009	Intermediate Similarity	NPD1565	Approved
0.7009	Intermediate Similarity	NPD1566	Phase 3
0.7	Intermediate Similarity	NPD17	Approved
0.7	Intermediate Similarity	NPD5305	Approved
0.7	Intermediate Similarity	NPD1110	Approved
0.7	Intermediate Similarity	NPD1362	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5306	Approved
0.7	Intermediate Similarity	NPD1104	Approved
0.7	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1109	Approved
0.7	Intermediate Similarity	NPD3170	Approved
0.6992	Remote Similarity	NPD1876	Approved
0.6992	Remote Similarity	NPD5667	Approved
0.699	Remote Similarity	NPD689	Discontinued
0.6977	Remote Similarity	NPD1654	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD1894	Discontinued
0.6961	Remote Similarity	NPD4793	Discontinued
0.6957	Remote Similarity	NPD969	Suspended
0.6947	Remote Similarity	NPD9716	Approved
0.6942	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD2797	Approved
0.693	Remote Similarity	NPD4234	Approved
0.693	Remote Similarity	NPD1752	Approved
0.693	Remote Similarity	NPD1317	Discontinued
0.693	Remote Similarity	NPD1756	Approved
0.693	Remote Similarity	NPD4233	Approved
0.6909	Remote Similarity	NPD1932	Approved
0.6899	Remote Similarity	NPD230	Phase 1
0.6899	Remote Similarity	NPD1933	Approved
0.6894	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD4807	Approved
0.6885	Remote Similarity	NPD1281	Approved
0.6885	Remote Similarity	NPD4806	Approved
0.6881	Remote Similarity	NPD7798	Approved
0.6875	Remote Similarity	NPD7713	Phase 3
0.687	Remote Similarity	NPD2799	Discontinued
0.6869	Remote Similarity	NPD942	Approved
0.6864	Remote Similarity	NPD4198	Discontinued
0.686	Remote Similarity	NPD1778	Approved
0.6842	Remote Similarity	NPD2329	Discontinued
0.6838	Remote Similarity	NPD2650	Approved
0.6838	Remote Similarity	NPD2652	Approved
0.6829	Remote Similarity	NPD1608	Approved
0.6829	Remote Similarity	NPD6637	Approved
0.6822	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD4307	Phase 2
0.6822	Remote Similarity	NPD3140	Approved
0.6822	Remote Similarity	NPD3142	Approved
0.6804	Remote Similarity	NPD9294	Approved
0.6803	Remote Similarity	NPD4106	Approved
0.6803	Remote Similarity	NPD4136	Approved
0.6803	Remote Similarity	NPD4135	Approved
0.68	Remote Similarity	NPD3266	Approved
0.68	Remote Similarity	NPD3267	Approved
0.6797	Remote Similarity	NPD3764	Approved
0.6797	Remote Similarity	NPD2313	Discontinued
0.6797	Remote Similarity	NPD411	Approved
0.6796	Remote Similarity	NPD650	Approved
0.6792	Remote Similarity	NPD7631	Approved
0.6791	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.678	Remote Similarity	NPD9281	Approved
0.678	Remote Similarity	NPD4766	Approved
0.678	Remote Similarity	NPD1246	Approved
0.6777	Remote Similarity	NPD5691	Approved
0.6774	Remote Similarity	NPD4359	Approved
0.6769	Remote Similarity	NPD447	Suspended
0.6765	Remote Similarity	NPD7236	Approved
0.6752	Remote Similarity	NPD7094	Approved
0.6752	Remote Similarity	NPD6858	Approved
0.6752	Remote Similarity	NPD2607	Approved
0.6746	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD6085	Phase 2
0.6741	Remote Similarity	NPD4628	Phase 3
0.6724	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.672	Remote Similarity	NPD1283	Approved
0.6716	Remote Similarity	NPD6414	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD7609	Phase 3
0.6696	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD9494	Approved
0.6692	Remote Similarity	NPD2935	Discontinued
0.6692	Remote Similarity	NPD2979	Phase 3
0.6692	Remote Similarity	NPD1551	Phase 2
0.6691	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD2558	Approved
0.6667	Remote Similarity	NPD2549	Approved
0.6667	Remote Similarity	NPD694	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5292	Approved
0.6667	Remote Similarity	NPD3496	Discontinued
0.6667	Remote Similarity	NPD2553	Approved
0.6667	Remote Similarity	NPD4576	Approved
0.6667	Remote Similarity	NPD2552	Approved
0.6667	Remote Similarity	NPD3268	Approved
0.6667	Remote Similarity	NPD1889	Phase 1
0.6667	Remote Similarity	NPD9471	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2550	Approved
0.6667	Remote Similarity	NPD5291	Approved
0.6667	Remote Similarity	NPD2555	Approved
0.6667	Remote Similarity	NPD4574	Approved
0.6642	Remote Similarity	NPD7611	Approved
0.6641	Remote Similarity	NPD4622	Approved
0.6641	Remote Similarity	NPD4618	Approved
0.664	Remote Similarity	NPD5157	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