NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	209.11
Volume:	217.077
LogP:	1.228
LogD:	1.276
LogS:	-1.241
# Rotatable Bonds:	5
TPSA:	59.42
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	1
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.765
Synthetic Accessibility Score:	2.227
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.579
MDCK Permeability:	2.6158166292589158e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.054
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.811
Plasma Protein Binding (PPB):	43.73219680786133%
Volume Distribution (VD):	0.928
Pgp-substrate:	51.17831802368164%

ADMET: Metabolism

CYP1A2-inhibitor:	0.464
CYP1A2-substrate:	0.78
CYP2C19-inhibitor:	0.141
CYP2C19-substrate:	0.2
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.618
CYP2D6-inhibitor:	0.104
CYP2D6-substrate:	0.698
CYP3A4-inhibitor:	0.076
CYP3A4-substrate:	0.273

ADMET: Excretion

Clearance (CL):	11.434
Half-life (T1/2):	0.87

ADMET: Toxicity

hERG Blockers:	0.033
Human Hepatotoxicity (H-HT):	0.253
Drug-inuced Liver Injury (DILI):	0.212
AMES Toxicity:	0.09
Rat Oral Acute Toxicity:	0.069
Maximum Recommended Daily Dose:	0.289
Skin Sensitization:	0.176
Carcinogencity:	0.582
Eye Corrosion:	0.012
Eye Irritation:	0.103
Respiratory Toxicity:	0.513

Download Data

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

Natural Product: NPC116573

Natural Product ID:	NPC116573
*Common Name:**	Methyl Multijuguinate
IUPAC Name:	methyl 4-(5-hydroxy-6-methylpyridin-2-yl)butanoate
Synonyms:	methyl multijuguinate
Standard InCHIKey:	GCAMBACYWCGZAG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H15NO3/c1-8-10(13)7-6-9(12-8)4-3-5-11(14)15-2/h6-7,13H,3-5H2,1-2H3
SMILES:	Cc1c(ccc(CCCC(=O)OC)n1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2023557
PubChem CID:	57379201
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000089] Pyridines and derivatives [CHEMONTID:0004152] Methylpyridines

*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
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[20000694]
NPO9634	Senna multijuga	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22304303]
NPO9634	Senna multijuga	Species	Fabaceae	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	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	MIC	=	3.0	ug	PMID[450887]
NPT66	Individual Protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	40.0	%	PMID[450887]

☑ 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 NPC116573 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	251
0.1-0.2	3125
0.2-0.3	13510
0.3-0.4	11461
0.4-0.5	10168
0.5-0.6	3102
0.6-0.7	998
0.7-0.8	75
0.8-0.85	0
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9122	High Similarity	NPC257142
0.9067	High Similarity	NPC284348
0.86	High Similarity	NPC470404
0.86	High Similarity	NPC470403
0.86	High Similarity	NPC470394
0.8487	Intermediate Similarity	NPC470395
0.7987	Intermediate Similarity	NPC153769
0.7853	Intermediate Similarity	NPC230403
0.7848	Intermediate Similarity	NPC161292
0.7806	Intermediate Similarity	NPC85443
0.7798	Intermediate Similarity	NPC253810
0.7736	Intermediate Similarity	NPC220523
0.7701	Intermediate Similarity	NPC320394
0.7614	Intermediate Similarity	NPC194040
0.7602	Intermediate Similarity	NPC303225
0.7584	Intermediate Similarity	NPC144381
0.7568	Intermediate Similarity	NPC317572
0.7545	Intermediate Similarity	NPC79911
0.7485	Intermediate Similarity	NPC120798
0.7473	Intermediate Similarity	NPC476098
0.7471	Intermediate Similarity	NPC44161
0.7458	Intermediate Similarity	NPC241025
0.743	Intermediate Similarity	NPC183805
0.7429	Intermediate Similarity	NPC478032
0.7389	Intermediate Similarity	NPC328029
0.7375	Intermediate Similarity	NPC60553
0.7358	Intermediate Similarity	NPC118228
0.7355	Intermediate Similarity	NPC174421
0.7354	Intermediate Similarity	NPC321428
0.7351	Intermediate Similarity	NPC280714
0.7349	Intermediate Similarity	NPC63562
0.7312	Intermediate Similarity	NPC318935
0.731	Intermediate Similarity	NPC41717
0.7306	Intermediate Similarity	NPC250448
0.7297	Intermediate Similarity	NPC472284
0.7297	Intermediate Similarity	NPC306376
0.7278	Intermediate Similarity	NPC322644
0.7268	Intermediate Similarity	NPC45850
0.7263	Intermediate Similarity	NPC42591
0.7262	Intermediate Similarity	NPC132680
0.7262	Intermediate Similarity	NPC269919
0.725	Intermediate Similarity	NPC280853
0.7245	Intermediate Similarity	NPC314270
0.7228	Intermediate Similarity	NPC276517
0.7219	Intermediate Similarity	NPC84508
0.7211	Intermediate Similarity	NPC472287
0.7211	Intermediate Similarity	NPC472286
0.7207	Intermediate Similarity	NPC207851
0.7205	Intermediate Similarity	NPC285016
0.7205	Intermediate Similarity	NPC245657
0.72	Intermediate Similarity	NPC95898
0.7195	Intermediate Similarity	NPC302159
0.7193	Intermediate Similarity	NPC263439
0.7188	Intermediate Similarity	NPC471596
0.7186	Intermediate Similarity	NPC36168
0.7182	Intermediate Similarity	NPC206186
0.7178	Intermediate Similarity	NPC471598
0.7176	Intermediate Similarity	NPC322976
0.7176	Intermediate Similarity	NPC63338
0.7176	Intermediate Similarity	NPC25899
0.7176	Intermediate Similarity	NPC324203
0.7168	Intermediate Similarity	NPC470894
0.7135	Intermediate Similarity	NPC52831
0.7135	Intermediate Similarity	NPC325705
0.7128	Intermediate Similarity	NPC213308
0.7127	Intermediate Similarity	NPC314573
0.7126	Intermediate Similarity	NPC473764
0.7126	Intermediate Similarity	NPC314940
0.7121	Intermediate Similarity	NPC315804
0.7121	Intermediate Similarity	NPC313804
0.7113	Intermediate Similarity	NPC294375
0.7093	Intermediate Similarity	NPC211187
0.7093	Intermediate Similarity	NPC118511
0.7083	Intermediate Similarity	NPC53344
0.7083	Intermediate Similarity	NPC283117
0.7083	Intermediate Similarity	NPC316403
0.7071	Intermediate Similarity	NPC184408
0.7065	Intermediate Similarity	NPC51388
0.7062	Intermediate Similarity	NPC84347
0.7049	Intermediate Similarity	NPC110741
0.7047	Intermediate Similarity	NPC39679
0.7037	Intermediate Similarity	NPC315491
0.7037	Intermediate Similarity	NPC45459
0.7035	Intermediate Similarity	NPC48192
0.7	Intermediate Similarity	NPC219963
0.7	Intermediate Similarity	NPC266551
0.7	Intermediate Similarity	NPC161887
0.6989	Remote Similarity	NPC252590
0.6975	Remote Similarity	NPC471594
0.6971	Remote Similarity	NPC1527
0.697	Remote Similarity	NPC469928
0.6966	Remote Similarity	NPC194724
0.6961	Remote Similarity	NPC244536
0.6942	Remote Similarity	NPC474701
0.6936	Remote Similarity	NPC47298
0.6936	Remote Similarity	NPC315214
0.6932	Remote Similarity	NPC256828
0.6932	Remote Similarity	NPC126481
0.6931	Remote Similarity	NPC478141
0.6927	Remote Similarity	NPC283152
0.6923	Remote Similarity	NPC325297
0.6923	Remote Similarity	NPC62069
0.6907	Remote Similarity	NPC88008
0.6905	Remote Similarity	NPC13432
0.6902	Remote Similarity	NPC36498
0.6897	Remote Similarity	NPC159319
0.6897	Remote Similarity	NPC32028
0.6888	Remote Similarity	NPC309845
0.6884	Remote Similarity	NPC330009
0.6882	Remote Similarity	NPC26872
0.6878	Remote Similarity	NPC186351
0.6878	Remote Similarity	NPC90229
0.6878	Remote Similarity	NPC141454
0.6872	Remote Similarity	NPC288943
0.6869	Remote Similarity	NPC39500
0.6862	Remote Similarity	NPC146724
0.6859	Remote Similarity	NPC151489
0.6854	Remote Similarity	NPC191310
0.6853	Remote Similarity	NPC87413
0.685	Remote Similarity	NPC293151
0.6839	Remote Similarity	NPC177404
0.6839	Remote Similarity	NPC165599
0.6821	Remote Similarity	NPC193238
0.6821	Remote Similarity	NPC113812
0.6821	Remote Similarity	NPC270918
0.6816	Remote Similarity	NPC174576
0.6811	Remote Similarity	NPC66083
0.6809	Remote Similarity	NPC226202
0.6804	Remote Similarity	NPC472259
0.68	Remote Similarity	NPC3207
0.6798	Remote Similarity	NPC273532
0.6793	Remote Similarity	NPC20249
0.6784	Remote Similarity	NPC232225
0.6782	Remote Similarity	NPC285635
0.678	Remote Similarity	NPC179287
0.6778	Remote Similarity	NPC286195
0.6774	Remote Similarity	NPC44354
0.6769	Remote Similarity	NPC300156
0.6768	Remote Similarity	NPC220337
0.6763	Remote Similarity	NPC26850
0.6761	Remote Similarity	NPC471178
0.676	Remote Similarity	NPC474409
0.676	Remote Similarity	NPC259545
0.676	Remote Similarity	NPC471294
0.6758	Remote Similarity	NPC478023
0.6753	Remote Similarity	NPC134848
0.6748	Remote Similarity	NPC29702
0.6738	Remote Similarity	NPC3715
0.6735	Remote Similarity	NPC244741
0.6734	Remote Similarity	NPC472098
0.6732	Remote Similarity	NPC205372
0.6721	Remote Similarity	NPC118776
0.6718	Remote Similarity	NPC314648
0.6716	Remote Similarity	NPC74969
0.6716	Remote Similarity	NPC60621
0.6705	Remote Similarity	NPC473057
0.6704	Remote Similarity	NPC14651
0.6704	Remote Similarity	NPC121658
0.6703	Remote Similarity	NPC219336
0.6703	Remote Similarity	NPC295158
0.6703	Remote Similarity	NPC88363
0.6703	Remote Similarity	NPC164340
0.6702	Remote Similarity	NPC156704
0.6701	Remote Similarity	NPC57398
0.67	Remote Similarity	NPC89508
0.6686	Remote Similarity	NPC315829
0.6685	Remote Similarity	NPC243058
0.6683	Remote Similarity	NPC146418
0.6683	Remote Similarity	NPC9894
0.6683	Remote Similarity	NPC274640
0.6667	Remote Similarity	NPC90415
0.6667	Remote Similarity	NPC278451
0.665	Remote Similarity	NPC4687
0.665	Remote Similarity	NPC94842
0.6649	Remote Similarity	NPC203635
0.6649	Remote Similarity	NPC470586
0.6649	Remote Similarity	NPC109922
0.6648	Remote Similarity	NPC217372
0.6648	Remote Similarity	NPC183662
0.6648	Remote Similarity	NPC219848
0.6648	Remote Similarity	NPC476518
0.6648	Remote Similarity	NPC15573
0.6634	Remote Similarity	NPC148183
0.6634	Remote Similarity	NPC152768
0.6632	Remote Similarity	NPC123395
0.6632	Remote Similarity	NPC128823
0.6632	Remote Similarity	NPC192306
0.6632	Remote Similarity	NPC476167
0.6629	Remote Similarity	NPC108469
0.6616	Remote Similarity	NPC86834
0.6616	Remote Similarity	NPC210828
0.6614	Remote Similarity	NPC114974
0.6612	Remote Similarity	NPC232340
0.6612	Remote Similarity	NPC256268
0.6612	Remote Similarity	NPC72980
0.6611	Remote Similarity	NPC258773
0.6611	Remote Similarity	NPC249614
0.6611	Remote Similarity	NPC158129
0.6604	Remote Similarity	NPC182222
0.6602	Remote Similarity	NPC144452

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 NPC116573 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	632
0.2-0.3	1014
0.3-0.4	1523
0.4-0.5	3477
0.5-0.6	1926
0.6-0.7	380
0.7-0.8	15
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7818	Intermediate Similarity	NPD861	Approved
0.7818	Intermediate Similarity	NPD862	Approved
0.7818	Intermediate Similarity	NPD863	Approved
0.7744	Intermediate Similarity	NPD604	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD158	Discontinued
0.7293	Intermediate Similarity	NPD5316	Approved
0.7273	Intermediate Similarity	NPD5352	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD9383	Approved
0.7262	Intermediate Similarity	NPD9382	Approved
0.7216	Intermediate Similarity	NPD6159	Phase 2
0.7189	Intermediate Similarity	NPD5512	Phase 3
0.7176	Intermediate Similarity	NPD9398	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD9510	Approved
0.7113	Intermediate Similarity	NPD7703	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD2844	Phase 3
0.7062	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD484	Approved
0.7024	Intermediate Similarity	NPD9706	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD8356	Approved
0.7011	Intermediate Similarity	NPD1213	Phase 3
0.697	Remote Similarity	NPD2433	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD4086	Phase 1
0.6954	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4805	Approved
0.6936	Remote Similarity	NPD1685	Approved
0.6936	Remote Similarity	NPD1684	Approved
0.6927	Remote Similarity	NPD6641	Approved
0.6927	Remote Similarity	NPD6642	Approved
0.6919	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.691	Remote Similarity	NPD9690	Approved
0.6909	Remote Similarity	NPD3525	Discontinued
0.6907	Remote Similarity	NPD5429	Discontinued
0.6902	Remote Similarity	NPD9363	Approved
0.6902	Remote Similarity	NPD9364	Phase 2
0.6895	Remote Similarity	NPD2176	Approved
0.6895	Remote Similarity	NPD2175	Phase 3
0.6895	Remote Similarity	NPD2177	Approved
0.6891	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5003	Discontinued
0.6878	Remote Similarity	NPD8430	Approved
0.6871	Remote Similarity	NPD203	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD3779	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD5416	Discontinued
0.6831	Remote Similarity	NPD5083	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4804	Approved
0.6828	Remote Similarity	NPD2565	Phase 2
0.6828	Remote Similarity	NPD2564	Approved
0.6824	Remote Similarity	NPD9595	Approved
0.6824	Remote Similarity	NPD9596	Approved
0.6811	Remote Similarity	NPD2383	Phase 1
0.68	Remote Similarity	NPD5088	Discontinued
0.6796	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD1229	Phase 2
0.6786	Remote Similarity	NPD2916	Discontinued
0.6784	Remote Similarity	NPD180	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD9705	Discontinued
0.6782	Remote Similarity	NPD112	Approved
0.6763	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD5317	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7538	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD565	Phase 2
0.6721	Remote Similarity	NPD4204	Approved
0.6721	Remote Similarity	NPD4203	Approved
0.6705	Remote Similarity	NPD1631	Approved
0.6703	Remote Similarity	NPD3920	Phase 2
0.6684	Remote Similarity	NPD4396	Clinical (unspecified phase)
0.6684	Remote Similarity	NPD5975	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD852	Discontinued
0.6667	Remote Similarity	NPD925	Approved
0.6667	Remote Similarity	NPD926	Approved
0.665	Remote Similarity	NPD6290	Phase 2
0.6649	Remote Similarity	NPD6550	Discontinued
0.6647	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD9695	Approved
0.6631	Remote Similarity	NPD6393	Clinical (unspecified phase)
0.6631	Remote Similarity	NPD1034	Phase 3
0.6631	Remote Similarity	NPD1033	Clinical (unspecified phase)
0.663	Remote Similarity	NPD3178	Discontinued
0.663	Remote Similarity	NPD9362	Approved
0.6629	Remote Similarity	NPD5255	Approved
0.6619	Remote Similarity	NPD7284	Clinical (unspecified phase)
0.6618	Remote Similarity	NPD3258	Approved
0.6617	Remote Similarity	NPD3243	Approved
0.6615	Remote Similarity	NPD6988	Phase 1
0.6615	Remote Similarity	NPD2779	Approved
0.6613	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD1503	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4502	Phase 2
0.6598	Remote Similarity	NPD5497	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD4602	Approved
0.6596	Remote Similarity	NPD408	Approved
0.6596	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD6872	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD3263	Phase 3
0.658	Remote Similarity	NPD772	Phase 3
0.6579	Remote Similarity	NPD6665	Discontinued
0.6578	Remote Similarity	NPD5256	Discontinued
0.6569	Remote Similarity	NPD7395	Discontinued
0.6567	Remote Similarity	NPD5866	Approved
0.6566	Remote Similarity	NPD9076	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD4081	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD721	Approved
0.6557	Remote Similarity	NPD5751	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD1573	Approved
0.6556	Remote Similarity	NPD1575	Approved
0.655	Remote Similarity	NPD5420	Discontinued
0.6548	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.654	Remote Similarity	NPD1867	Approved
0.6536	Remote Similarity	NPD425	Approved
0.6536	Remote Similarity	NPD424	Approved
0.6534	Remote Similarity	NPD1630	Approved
0.6529	Remote Similarity	NPD9074	Approved
0.6529	Remote Similarity	NPD9075	Approved
0.6524	Remote Similarity	NPD4889	Approved
0.6522	Remote Similarity	NPD8304	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD2123	Phase 3
0.6519	Remote Similarity	NPD6739	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD5936	Approved
0.6517	Remote Similarity	NPD5939	Approved
0.6502	Remote Similarity	NPD3257	Approved
0.6498	Remote Similarity	NPD6716	Phase 1
0.6488	Remote Similarity	NPD3354	Phase 2
0.6486	Remote Similarity	NPD6452	Discontinued
0.6485	Remote Similarity	NPD7069	Discontinued
0.6482	Remote Similarity	NPD7222	Phase 2
0.6471	Remote Similarity	NPD1096	Discontinued
0.6467	Remote Similarity	NPD2896	Discontinued
0.6464	Remote Similarity	NPD4724	Clinical (unspecified phase)
0.6464	Remote Similarity	NPD5319	Approved
0.6464	Remote Similarity	NPD5320	Approved
0.6462	Remote Similarity	NPD2778	Approved
0.6458	Remote Similarity	NPD4526	Approved
0.6458	Remote Similarity	NPD4528	Approved
0.6458	Remote Similarity	NPD4529	Approved
0.6448	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6437	Remote Similarity	NPD6158	Phase 2
0.6437	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD2762	Phase 2
0.6429	Remote Similarity	NPD7603	Discontinued
0.6425	Remote Similarity	NPD4418	Discontinued
0.6425	Remote Similarity	NPD6590	Discontinued
0.6422	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD4897	Phase 2
0.6417	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD2920	Discontinued
0.641	Remote Similarity	NPD7778	Approved
0.641	Remote Similarity	NPD7777	Approved
0.641	Remote Similarity	NPD712	Clinical (unspecified phase)
0.641	Remote Similarity	NPD7946	Pre-registration
0.641	Remote Similarity	NPD53	Approved
0.641	Remote Similarity	NPD7889	Clinical (unspecified phase)
0.641	Remote Similarity	NPD2727	Phase 2
0.6409	Remote Similarity	NPD2781	Approved
0.6408	Remote Similarity	NPD5632	Approved
0.6408	Remote Similarity	NPD8109	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4429	Discontinued
0.6406	Remote Similarity	NPD9689	Approved
0.6398	Remote Similarity	NPD5445	Approved
0.6394	Remote Similarity	NPD7726	Phase 1
0.6393	Remote Similarity	NPD750	Phase 2
0.6393	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6182	Approved
0.6393	Remote Similarity	NPD43	Approved
0.6389	Remote Similarity	NPD2780	Approved
0.6389	Remote Similarity	NPD2782	Approved
0.6386	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD1166	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD1467	Approved
0.6385	Remote Similarity	NPD1466	Phase 3
0.6384	Remote Similarity	NPD2582	Approved
0.6384	Remote Similarity	NPD9574	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD2581	Approved
0.6377	Remote Similarity	NPD6974	Phase 3
0.6377	Remote Similarity	NPD4312	Approved
0.6376	Remote Similarity	NPD9507	Approved
0.6364	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD1783	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD9284	Approved
0.6358	Remote Similarity	NPD9271	Approved
0.6355	Remote Similarity	NPD7468	Clinical (unspecified phase)
0.6353	Remote Similarity	NPD5020	Approved
0.6353	Remote Similarity	NPD1592	Phase 3
0.6346	Remote Similarity	NPD7180	Phase 3
0.6344	Remote Similarity	NPD1587	Approved
0.6343	Remote Similarity	NPD2882	Phase 1
0.6333	Remote Similarity	NPD7547	Clinical (unspecified phase)
0.6327	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD749	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD3923	Approved
0.6321	Remote Similarity	NPD3921	Approved
0.6321	Remote Similarity	NPD3922	Approved
0.6321	Remote Similarity	NPD6569	Phase 2
0.6321	Remote Similarity	NPD3924	Approved
0.6321	Remote Similarity	NPD9243	Approved
0.6321	Remote Similarity	NPD4328	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