NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	480.25
Volume:	507.564
LogP:	4.322
LogD:	4.228
LogS:	-4.466
# Rotatable Bonds:	5
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.5
Synthetic Accessibility Score:	5.083
Fsp3:	0.552
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.817
MDCK Permeability:	2.399075856374111e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.194
30% Bioavailability (F30%):	0.984

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.336
Plasma Protein Binding (PPB):	95.34539031982422%
Volume Distribution (VD):	1.974
Pgp-substrate:	4.555611610412598%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.098
CYP2C19-inhibitor:	0.543
CYP2C19-substrate:	0.135
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.124
CYP2D6-inhibitor:	0.191
CYP2D6-substrate:	0.126
CYP3A4-inhibitor:	0.913
CYP3A4-substrate:	0.47

ADMET: Excretion

Clearance (CL):	7.027
Half-life (T1/2):	0.399

ADMET: Toxicity

hERG Blockers:	0.511
Human Hepatotoxicity (H-HT):	0.894
Drug-inuced Liver Injury (DILI):	0.388
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.269
Maximum Recommended Daily Dose:	0.823
Skin Sensitization:	0.949
Carcinogencity:	0.065
Eye Corrosion:	0.004
Eye Irritation:	0.02
Respiratory Toxicity:	0.876

Download Data

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

Natural Product: NPC477367

Natural Product ID:	NPC477367
*Common Name:**	[(1R,3E,5S,7S,9Z,11R,12R,13S,14S)-13-acetyloxy-11-hydroxy-3,6,6,10,14-pentamethyl-2-oxo-1-tricyclo[10.3.0.05,7]pentadeca-3,9-dienyl] benzoate
IUPAC Name:	[(1R,3E,5S,7S,9Z,11R,12R,13S,14S)-13-acetyloxy-11-hydroxy-3,6,6,10,14-pentamethyl-2-oxo-1-tricyclo[10.3.0.05,7]pentadeca-3,9-dienyl] benzoate
Synonyms:
Standard InCHIKey:	MZSLFIHMXSUKAF-NLZFDMNXSA-N
Standard InCHI:	InChI=1S/C29H36O6/c1-16-12-13-21-22(28(21,5)6)14-17(2)26(32)29(35-27(33)20-10-8-7-9-11-20)15-18(3)25(34-19(4)30)23(29)24(16)31/h7-12,14,18,21-25,31H,13,15H2,1-6H3/b16-12-,17-14+/t18-,21-,22-,23+,24-,25-,29+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@@H]([C@H]1OC(=O)C)[C@H](/C(=C\C[C@H]3[C@@H](C3(C)C)/C=C(/C2=O)\C)/C)O)OC(=O)C4=CC=CC=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56683354
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19036584]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	Eukaryota	stems	Botanical Garden, Osmania University, Hyderabad, Andhra Pradesh	2006-AUG	PMID[21534583]
NPO28682	Jatropha multifida	Species	Euphorbiaceae	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

Activity Type	# Activity
Tissue	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT177	Tissue	Aorta	Rattus norvegicus	Activity	=	48	%	PMID[21534583]

☑ 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 NPC477367 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	274
0.1-0.2	1039
0.2-0.3	2320
0.3-0.4	5924
0.4-0.5	11771
0.5-0.6	14556
0.6-0.7	6006
0.7-0.8	634
0.8-0.85	37
0.85-0.9	94
0.9-0.95	33
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC232888
0.9921	High Similarity	NPC477368
0.9843	High Similarity	NPC477364
0.9612	High Similarity	NPC477359
0.9606	High Similarity	NPC42234
0.9457	High Similarity	NPC477360
0.9453	High Similarity	NPC272946
0.9449	High Similarity	NPC477370
0.937	High Similarity	NPC477365
0.9291	High Similarity	NPC477363
0.9291	High Similarity	NPC477366
0.9242	High Similarity	NPC270364
0.9242	High Similarity	NPC472247
0.9225	High Similarity	NPC37968
0.9173	High Similarity	NPC477358
0.9134	High Similarity	NPC477362
0.9071	High Similarity	NPC477099
0.9071	High Similarity	NPC477097
0.9071	High Similarity	NPC477101
0.907	High Similarity	NPC477357
0.9044	High Similarity	NPC473497
0.9037	High Similarity	NPC276652
0.8984	High Similarity	NPC8990
0.8955	High Similarity	NPC265459
0.8955	High Similarity	NPC290833
0.8955	High Similarity	NPC475262
0.8915	High Similarity	NPC477369
0.8913	High Similarity	NPC45307
0.8913	High Similarity	NPC153214
0.8905	High Similarity	NPC473654
0.8905	High Similarity	NPC475413
0.8905	High Similarity	NPC474303
0.8889	High Similarity	NPC194769
0.8889	High Similarity	NPC285221
0.8881	High Similarity	NPC477098
0.8881	High Similarity	NPC477100
0.8881	High Similarity	NPC472250
0.8872	High Similarity	NPC233692
0.8824	High Similarity	NPC86772
0.8803	High Similarity	NPC125033
0.8803	High Similarity	NPC25484
0.8803	High Similarity	NPC232583
0.8794	High Similarity	NPC205389
0.8777	High Similarity	NPC477094
0.8777	High Similarity	NPC477096
0.8759	High Similarity	NPC272523
0.8759	High Similarity	NPC325805
0.8741	High Similarity	NPC28836
0.8741	High Similarity	NPC311492
0.8731	High Similarity	NPC239358
0.8723	High Similarity	NPC170668
0.8696	High Similarity	NPC251294
0.8696	High Similarity	NPC475660
0.8667	High Similarity	NPC472248
0.8643	High Similarity	NPC82467
0.8633	High Similarity	NPC242355
0.8613	High Similarity	NPC217673
0.8613	High Similarity	NPC202729
0.8613	High Similarity	NPC52523
0.8593	High Similarity	NPC233860
0.8592	High Similarity	NPC477095
0.8582	High Similarity	NPC475452
0.8582	High Similarity	NPC475671
0.8551	High Similarity	NPC27721
0.854	High Similarity	NPC79699
0.854	High Similarity	NPC200154
0.8496	Intermediate Similarity	NPC472706
0.8489	Intermediate Similarity	NPC473301
0.845	Intermediate Similarity	NPC472708
0.8433	Intermediate Similarity	NPC472707
0.831	Intermediate Similarity	NPC183540
0.8309	Intermediate Similarity	NPC475508
0.8309	Intermediate Similarity	NPC122504
0.8309	Intermediate Similarity	NPC3450
0.8271	Intermediate Similarity	NPC472704
0.8264	Intermediate Similarity	NPC25043
0.8264	Intermediate Similarity	NPC134131
0.8239	Intermediate Similarity	NPC187566
0.8201	Intermediate Similarity	NPC126516
0.8201	Intermediate Similarity	NPC329913
0.8201	Intermediate Similarity	NPC153617
0.8195	Intermediate Similarity	NPC472703
0.8176	Intermediate Similarity	NPC22571
0.8176	Intermediate Similarity	NPC283875
0.8176	Intermediate Similarity	NPC469648
0.8176	Intermediate Similarity	NPC469647
0.8176	Intermediate Similarity	NPC138641
0.8148	Intermediate Similarity	NPC476599
0.8138	Intermediate Similarity	NPC471162
0.8133	Intermediate Similarity	NPC70344
0.8125	Intermediate Similarity	NPC95449
0.8108	Intermediate Similarity	NPC472398
0.8106	Intermediate Similarity	NPC473243
0.8099	Intermediate Similarity	NPC170718
0.8088	Intermediate Similarity	NPC169913
0.8071	Intermediate Similarity	NPC134937
0.8071	Intermediate Similarity	NPC298547
0.8071	Intermediate Similarity	NPC324898
0.8071	Intermediate Similarity	NPC203486
0.8067	Intermediate Similarity	NPC469456
0.8054	Intermediate Similarity	NPC233581
0.8054	Intermediate Similarity	NPC145649
0.8043	Intermediate Similarity	NPC82712
0.8015	Intermediate Similarity	NPC275576
0.8014	Intermediate Similarity	NPC149401
0.8014	Intermediate Similarity	NPC279637
0.8013	Intermediate Similarity	NPC11410
0.7987	Intermediate Similarity	NPC161955
0.7987	Intermediate Similarity	NPC55744
0.7986	Intermediate Similarity	NPC72915
0.7972	Intermediate Similarity	NPC9905
0.7931	Intermediate Similarity	NPC51181
0.7931	Intermediate Similarity	NPC182869
0.7917	Intermediate Similarity	NPC87934
0.7917	Intermediate Similarity	NPC162613
0.7905	Intermediate Similarity	NPC132652
0.7902	Intermediate Similarity	NPC327511
0.7902	Intermediate Similarity	NPC205305
0.7899	Intermediate Similarity	NPC115797
0.7899	Intermediate Similarity	NPC51448
0.7898	Intermediate Similarity	NPC161151
0.7891	Intermediate Similarity	NPC478264
0.7887	Intermediate Similarity	NPC477896
0.7887	Intermediate Similarity	NPC477893
0.7877	Intermediate Similarity	NPC477894
0.7877	Intermediate Similarity	NPC191387
0.7877	Intermediate Similarity	NPC131966
0.7874	Intermediate Similarity	NPC469636
0.7868	Intermediate Similarity	NPC471466
0.7867	Intermediate Similarity	NPC471103
0.7857	Intermediate Similarity	NPC470278
0.7847	Intermediate Similarity	NPC121268
0.7847	Intermediate Similarity	NPC53361
0.7846	Intermediate Similarity	NPC153053
0.7846	Intermediate Similarity	NPC307651
0.7838	Intermediate Similarity	NPC478263
0.7829	Intermediate Similarity	NPC473632
0.7829	Intermediate Similarity	NPC251139
0.7829	Intermediate Similarity	NPC469730
0.7829	Intermediate Similarity	NPC132599
0.7829	Intermediate Similarity	NPC473670
0.7829	Intermediate Similarity	NPC21410
0.7817	Intermediate Similarity	NPC48929
0.781	Intermediate Similarity	NPC246166
0.7808	Intermediate Similarity	NPC192658
0.7808	Intermediate Similarity	NPC475135
0.7786	Intermediate Similarity	NPC471832
0.7778	Intermediate Similarity	NPC50872
0.777	Intermediate Similarity	NPC127857
0.7748	Intermediate Similarity	NPC51602
0.7733	Intermediate Similarity	NPC60509
0.7733	Intermediate Similarity	NPC250046
0.7733	Intermediate Similarity	NPC81698
0.7718	Intermediate Similarity	NPC312393
0.7712	Intermediate Similarity	NPC259144
0.7712	Intermediate Similarity	NPC114357
0.7712	Intermediate Similarity	NPC473611
0.7712	Intermediate Similarity	NPC155329
0.7703	Intermediate Similarity	NPC34943
0.7692	Intermediate Similarity	NPC82899
0.7692	Intermediate Similarity	NPC270699
0.7692	Intermediate Similarity	NPC321852
0.7687	Intermediate Similarity	NPC140021
0.7682	Intermediate Similarity	NPC198455
0.7682	Intermediate Similarity	NPC165260
0.7682	Intermediate Similarity	NPC7095
0.7682	Intermediate Similarity	NPC161239
0.7681	Intermediate Similarity	NPC295664
0.7677	Intermediate Similarity	NPC159692
0.7676	Intermediate Similarity	NPC125153
0.7662	Intermediate Similarity	NPC106895
0.7651	Intermediate Similarity	NPC471100
0.7651	Intermediate Similarity	NPC92867
0.7651	Intermediate Similarity	NPC471107
0.7651	Intermediate Similarity	NPC311825
0.7651	Intermediate Similarity	NPC125882
0.7647	Intermediate Similarity	NPC11588
0.7647	Intermediate Similarity	NPC134685
0.7647	Intermediate Similarity	NPC229545
0.7647	Intermediate Similarity	NPC248265
0.7647	Intermediate Similarity	NPC219419
0.7634	Intermediate Similarity	NPC161611
0.7632	Intermediate Similarity	NPC101043
0.7632	Intermediate Similarity	NPC306799
0.763	Intermediate Similarity	NPC204784
0.7622	Intermediate Similarity	NPC472656
0.7619	Intermediate Similarity	NPC266374
0.7619	Intermediate Similarity	NPC471862
0.7616	Intermediate Similarity	NPC473215
0.7615	Intermediate Similarity	NPC305912
0.7615	Intermediate Similarity	NPC476003
0.7615	Intermediate Similarity	NPC1082
0.7615	Intermediate Similarity	NPC260818
0.761	Intermediate Similarity	NPC477491
0.76	Intermediate Similarity	NPC240115
0.76	Intermediate Similarity	NPC20255
0.76	Intermediate Similarity	NPC477737
0.76	Intermediate Similarity	NPC475552
0.7597	Intermediate Similarity	NPC282239
0.7576	Intermediate Similarity	NPC474363

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 NPC477367 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	223
0.1-0.2	790
0.2-0.3	1623
0.3-0.4	2800
0.4-0.5	2335
0.5-0.6	1097
0.6-0.7	259
0.7-0.8	21
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
0.8652	High Similarity	NPD7236	Approved
0.8356	Intermediate Similarity	NPD7239	Suspended
0.7857	Intermediate Similarity	NPD7058	Phase 2
0.7857	Intermediate Similarity	NPD7057	Phase 3
0.7826	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7615	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7571	Intermediate Similarity	NPD6085	Phase 2
0.7531	Intermediate Similarity	NPD7799	Discontinued
0.7519	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.748	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD2182	Approved
0.7442	Intermediate Similarity	NPD6685	Approved
0.7431	Intermediate Similarity	NPD7961	Discontinued
0.7388	Intermediate Similarity	NPD2629	Approved
0.7379	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7344	Intermediate Similarity	NPD6647	Phase 2
0.7292	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD2067	Discontinued
0.7266	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD5765	Approved
0.7197	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7305	Phase 1
0.7154	Intermediate Similarity	NPD1237	Approved
0.7154	Intermediate Similarity	NPD164	Approved
0.7086	Intermediate Similarity	NPD6002	Phase 3
0.7086	Intermediate Similarity	NPD6005	Phase 3
0.7086	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD6004	Phase 3
0.7086	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD4198	Discontinued
0.7071	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD4628	Phase 3
0.7055	Intermediate Similarity	NPD7008	Discontinued
0.7051	Intermediate Similarity	NPD6273	Approved
0.705	Intermediate Similarity	NPD7741	Discontinued
0.7047	Intermediate Similarity	NPD6653	Approved
0.7037	Intermediate Similarity	NPD6912	Phase 3
0.7014	Intermediate Similarity	NPD6362	Approved
0.6985	Remote Similarity	NPD6858	Approved
0.6985	Remote Similarity	NPD7094	Approved
0.6972	Remote Similarity	NPD6287	Discontinued
0.6966	Remote Similarity	NPD5647	Approved
0.6957	Remote Similarity	NPD5760	Phase 2
0.6957	Remote Similarity	NPD5761	Phase 2
0.6941	Remote Similarity	NPD6764	Approved
0.6941	Remote Similarity	NPD7685	Pre-registration
0.6941	Remote Similarity	NPD6765	Approved
0.6929	Remote Similarity	NPD9545	Approved
0.6912	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD7137	Phase 2
0.6899	Remote Similarity	NPD9495	Approved
0.6884	Remote Similarity	NPD5951	Approved
0.6867	Remote Similarity	NPD6355	Discontinued
0.6863	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6663	Approved
0.6846	Remote Similarity	NPD1238	Approved
0.6842	Remote Similarity	NPD8368	Discontinued
0.6839	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD8407	Phase 2
0.6818	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1930	Approved
0.6818	Remote Similarity	NPD1929	Approved
0.6803	Remote Similarity	NPD5736	Approved
0.6782	Remote Similarity	NPD6785	Approved
0.6782	Remote Similarity	NPD6784	Approved
0.6779	Remote Similarity	NPD3764	Approved
0.6753	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD8434	Phase 2
0.6736	Remote Similarity	NPD4807	Approved
0.6736	Remote Similarity	NPD4806	Approved
0.6718	Remote Similarity	NPD2066	Phase 3
0.6715	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD5305	Approved
0.6713	Remote Similarity	NPD5306	Approved
0.6708	Remote Similarity	NPD7458	Discontinued
0.669	Remote Similarity	NPD7009	Phase 2
0.6689	Remote Similarity	NPD3661	Approved
0.6689	Remote Similarity	NPD3663	Approved
0.6689	Remote Similarity	NPD3662	Phase 3
0.6689	Remote Similarity	NPD3664	Approved
0.6688	Remote Similarity	NPD6190	Approved
0.6667	Remote Similarity	NPD1693	Approved
0.6667	Remote Similarity	NPD9493	Approved
0.6667	Remote Similarity	NPD6599	Discontinued
0.6667	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5762	Approved
0.6645	Remote Similarity	NPD5763	Approved
0.6645	Remote Similarity	NPD230	Phase 1
0.6642	Remote Similarity	NPD5909	Discontinued
0.6627	Remote Similarity	NPD7075	Discontinued
0.6623	Remote Similarity	NPD2799	Discontinued
0.662	Remote Similarity	NPD7610	Discontinued
0.6614	Remote Similarity	NPD9258	Approved
0.6614	Remote Similarity	NPD9256	Approved
0.6601	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD1876	Approved
0.6597	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5048	Discontinued
0.6589	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD3887	Approved
0.6575	Remote Similarity	NPD3972	Approved
0.6573	Remote Similarity	NPD8435	Approved
0.6573	Remote Similarity	NPD8361	Approved
0.6573	Remote Similarity	NPD8360	Approved
0.6571	Remote Similarity	NPD6010	Discontinued
0.6571	Remote Similarity	NPD2652	Approved
0.6571	Remote Similarity	NPD2650	Approved
0.6561	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD2313	Discontinued
0.6556	Remote Similarity	NPD3268	Approved
0.6552	Remote Similarity	NPD4135	Approved
0.6552	Remote Similarity	NPD4136	Approved
0.6552	Remote Similarity	NPD4106	Approved
0.6547	Remote Similarity	NPD969	Suspended
0.6528	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD8166	Discontinued
0.6516	Remote Similarity	NPD7033	Discontinued
0.6513	Remote Similarity	NPD7715	Approved
0.6513	Remote Similarity	NPD7714	Approved
0.6512	Remote Similarity	NPD1088	Approved
0.6503	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6799	Approved
0.6497	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6899	Approved
0.6496	Remote Similarity	NPD6881	Approved
0.6493	Remote Similarity	NPD1932	Approved
0.6486	Remote Similarity	NPD5667	Approved
0.6485	Remote Similarity	NPD6801	Discontinued
0.6478	Remote Similarity	NPD2354	Approved
0.6475	Remote Similarity	NPD6649	Approved
0.6475	Remote Similarity	NPD6650	Approved
0.6474	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD2935	Discontinued
0.6471	Remote Similarity	NPD4140	Approved
0.6467	Remote Similarity	NPD5204	Approved
0.6463	Remote Similarity	NPD9717	Approved
0.6461	Remote Similarity	NPD8150	Discontinued
0.646	Remote Similarity	NPD2533	Approved
0.646	Remote Similarity	NPD2532	Approved
0.646	Remote Similarity	NPD2534	Approved
0.6452	Remote Similarity	NPD2569	Approved
0.6452	Remote Similarity	NPD2567	Approved
0.6449	Remote Similarity	NPD2329	Discontinued
0.6448	Remote Similarity	NPD8485	Approved
0.6443	Remote Similarity	NPD2797	Approved
0.6433	Remote Similarity	NPD2346	Discontinued
0.6424	Remote Similarity	NPD6832	Phase 2
0.6424	Remote Similarity	NPD7055	Discontinued
0.6423	Remote Similarity	NPD5697	Approved
0.6415	Remote Similarity	NPD7003	Approved
0.6415	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD2575	Approved
0.6415	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD5585	Approved
0.6414	Remote Similarity	NPD4102	Approved
0.6414	Remote Similarity	NPD4105	Approved
0.6412	Remote Similarity	NPD8127	Discontinued
0.641	Remote Similarity	NPD4308	Phase 3
0.6408	Remote Similarity	NPD4766	Approved
0.6407	Remote Similarity	NPD5402	Approved
0.6405	Remote Similarity	NPD7713	Phase 3
0.6405	Remote Similarity	NPD6233	Phase 2
0.6403	Remote Similarity	NPD7102	Approved
0.6403	Remote Similarity	NPD6883	Approved
0.6403	Remote Similarity	NPD7290	Approved
0.6403	Remote Similarity	NPD1317	Discontinued
0.6402	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.64	Remote Similarity	NPD2798	Approved
0.6391	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD7095	Approved
0.638	Remote Similarity	NPD5403	Approved
0.6377	Remote Similarity	NPD6406	Approved
0.6358	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD1089	Approved
0.6357	Remote Similarity	NPD8130	Phase 1
0.6357	Remote Similarity	NPD6869	Approved
0.6357	Remote Similarity	NPD5785	Approved
0.6357	Remote Similarity	NPD6617	Approved
0.6357	Remote Similarity	NPD6847	Approved
0.6357	Remote Similarity	NPD1090	Approved
0.6357	Remote Similarity	NPD1086	Approved
0.6351	Remote Similarity	NPD1608	Approved
0.6351	Remote Similarity	NPD6637	Approved
0.635	Remote Similarity	NPD6675	Approved
0.635	Remote Similarity	NPD6402	Approved
0.635	Remote Similarity	NPD5739	Approved
0.635	Remote Similarity	NPD7128	Approved
0.6347	Remote Similarity	NPD7819	Suspended
0.6344	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.634	Remote Similarity	NPD6798	Discontinued
0.6336	Remote Similarity	NPD1202	Approved
0.6333	Remote Similarity	NPD2160	Approved
0.6333	Remote Similarity	NPD2626	Approved
0.6333	Remote Similarity	NPD2627	Approved
0.6333	Remote Similarity	NPD2625	Approved
0.6333	Remote Similarity	NPD2159	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