NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	480.25
Volume:	501.644
LogP:	4.986
LogD:	4.376
LogS:	-4.9
# Rotatable Bonds:	5
TPSA:	82.2
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.452
Synthetic Accessibility Score:	5.151
Fsp3:	0.621
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:	-4.932
MDCK Permeability:	3.273686161264777e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.086
30% Bioavailability (F30%):	0.804

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.053
Plasma Protein Binding (PPB):	92.41211700439453%
Volume Distribution (VD):	2.644
Pgp-substrate:	7.351131916046143%

ADMET: Metabolism

CYP1A2-inhibitor:	0.057
CYP1A2-substrate:	0.129
CYP2C19-inhibitor:	0.392
CYP2C19-substrate:	0.2
CYP2C9-inhibitor:	0.672
CYP2C9-substrate:	0.065
CYP2D6-inhibitor:	0.077
CYP2D6-substrate:	0.118
CYP3A4-inhibitor:	0.886
CYP3A4-substrate:	0.529

ADMET: Excretion

Clearance (CL):	5.914
Half-life (T1/2):	0.227

ADMET: Toxicity

hERG Blockers:	0.793
Human Hepatotoxicity (H-HT):	0.926
Drug-inuced Liver Injury (DILI):	0.683
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.384
Maximum Recommended Daily Dose:	0.52
Skin Sensitization:	0.945
Carcinogencity:	0.091
Eye Corrosion:	0.004
Eye Irritation:	0.022
Respiratory Toxicity:	0.866

Download Data

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

Natural Product: NPC477360

Natural Product ID:	NPC477360
*Common Name:**	[(1R,2R,4R,7S,9S,10E,13R,15S,16S)-16-acetyloxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-13-yl] benzoate
IUPAC Name:	[(1R,2R,4R,7S,9S,10E,13R,15S,16S)-16-acetyloxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-13-yl] benzoate
Synonyms:
Standard InCHIKey:	KXWUYCUPBXTAIE-AAEWGYDNSA-N
Standard InCHI:	InChI=1S/C29H36O6/c1-16-14-21-20(27(21,4)5)12-13-28(6)25(34-28)22-23(33-18(3)30)17(2)15-29(22,24(16)31)35-26(32)19-10-8-7-9-11-19/h7-11,14,17,20-23,25H,12-13,15H2,1-6H3/b16-14+/t17-,20-,21-,22+,23-,25+,28+,29+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)C)[C@@H]3[C@](O3)(CC[C@H]4[C@@H](C4(C)C)/C=C(/C2=O)\C)C)OC(=O)C5=CC=CC=C5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56669870
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	=	41	%	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 NPC477360 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	327
0.1-0.2	1384
0.2-0.3	2767
0.3-0.4	8231
0.4-0.5	12964
0.5-0.6	13678
0.6-0.7	2961
0.7-0.8	235
0.8-0.85	66
0.85-0.9	56
0.9-0.95	24
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9839	High Similarity	NPC42234
0.9688	High Similarity	NPC477358
0.9685	High Similarity	NPC477359
0.9531	High Similarity	NPC477368
0.9457	High Similarity	NPC477367
0.9457	High Similarity	NPC232888
0.9457	High Similarity	NPC270364
0.9453	High Similarity	NPC477364
0.9394	High Similarity	NPC473654
0.9254	High Similarity	NPC477096
0.9254	High Similarity	NPC477094
0.9242	High Similarity	NPC276652
0.9219	High Similarity	NPC272946
0.92	High Similarity	NPC8990
0.916	High Similarity	NPC475262
0.916	High Similarity	NPC290833
0.916	High Similarity	NPC265459
0.9141	High Similarity	NPC37968
0.9134	High Similarity	NPC477357
0.9127	High Similarity	NPC477369
0.9091	High Similarity	NPC285221
0.9091	High Similarity	NPC194769
0.9084	High Similarity	NPC472250
0.907	High Similarity	NPC475452
0.907	High Similarity	NPC475671
0.9051	High Similarity	NPC477095
0.9023	High Similarity	NPC86772
0.8971	High Similarity	NPC82467
0.8955	High Similarity	NPC325805
0.8955	High Similarity	NPC272523
0.8915	High Similarity	NPC477370
0.8906	High Similarity	NPC477366
0.8906	High Similarity	NPC477363
0.8898	High Similarity	NPC477362
0.8889	High Similarity	NPC475660
0.8889	High Similarity	NPC251294
0.8872	High Similarity	NPC472247
0.8857	High Similarity	NPC477101
0.8857	High Similarity	NPC477099
0.8857	High Similarity	NPC477097
0.8837	High Similarity	NPC477365
0.8824	High Similarity	NPC473497
0.8779	High Similarity	NPC3450
0.8779	High Similarity	NPC122504
0.8731	High Similarity	NPC79699
0.8696	High Similarity	NPC45307
0.8696	High Similarity	NPC153214
0.8686	High Similarity	NPC475413
0.8686	High Similarity	NPC474303
0.8671	High Similarity	NPC477100
0.8671	High Similarity	NPC477098
0.8592	High Similarity	NPC25484
0.8592	High Similarity	NPC232583
0.8592	High Similarity	NPC125033
0.8511	High Similarity	NPC170668
0.8496	Intermediate Similarity	NPC475508
0.8451	Intermediate Similarity	NPC205389
0.8417	Intermediate Similarity	NPC187566
0.8382	Intermediate Similarity	NPC153617
0.837	Intermediate Similarity	NPC233692
0.837	Intermediate Similarity	NPC239358
0.837	Intermediate Similarity	NPC233860
0.8333	Intermediate Similarity	NPC476599
0.8309	Intermediate Similarity	NPC472248
0.8295	Intermediate Similarity	NPC473243
0.8248	Intermediate Similarity	NPC311492
0.8248	Intermediate Similarity	NPC28836
0.8248	Intermediate Similarity	NPC134937
0.8248	Intermediate Similarity	NPC324898
0.8248	Intermediate Similarity	NPC298547
0.8188	Intermediate Similarity	NPC279637
0.8188	Intermediate Similarity	NPC200154
0.8188	Intermediate Similarity	NPC149401
0.8156	Intermediate Similarity	NPC242355
0.8134	Intermediate Similarity	NPC472706
0.8129	Intermediate Similarity	NPC217673
0.8129	Intermediate Similarity	NPC52523
0.8129	Intermediate Similarity	NPC202729
0.8099	Intermediate Similarity	NPC183540
0.8074	Intermediate Similarity	NPC472707
0.8071	Intermediate Similarity	NPC327511
0.8071	Intermediate Similarity	NPC27721
0.8071	Intermediate Similarity	NPC205305
0.8065	Intermediate Similarity	NPC469636
0.8045	Intermediate Similarity	NPC472704
0.8042	Intermediate Similarity	NPC191387
0.8042	Intermediate Similarity	NPC131966
0.8031	Intermediate Similarity	NPC307651
0.8029	Intermediate Similarity	NPC470278
0.8014	Intermediate Similarity	NPC121268
0.8014	Intermediate Similarity	NPC53361
0.8014	Intermediate Similarity	NPC473301
0.7986	Intermediate Similarity	NPC329913
0.7972	Intermediate Similarity	NPC475135
0.797	Intermediate Similarity	NPC472703
0.7955	Intermediate Similarity	NPC50872
0.7939	Intermediate Similarity	NPC472708
0.7933	Intermediate Similarity	NPC70344
0.7874	Intermediate Similarity	NPC270699
0.7874	Intermediate Similarity	NPC82899
0.7857	Intermediate Similarity	NPC126516
0.7842	Intermediate Similarity	NPC238370
0.7812	Intermediate Similarity	NPC161611
0.7808	Intermediate Similarity	NPC471100
0.7808	Intermediate Similarity	NPC471162
0.7808	Intermediate Similarity	NPC25043
0.7808	Intermediate Similarity	NPC471107
0.7808	Intermediate Similarity	NPC134131
0.7795	Intermediate Similarity	NPC305912
0.7795	Intermediate Similarity	NPC1082
0.7792	Intermediate Similarity	NPC55744
0.7786	Intermediate Similarity	NPC472656
0.7762	Intermediate Similarity	NPC170718
0.7755	Intermediate Similarity	NPC475552
0.7748	Intermediate Similarity	NPC469456
0.7733	Intermediate Similarity	NPC138641
0.7733	Intermediate Similarity	NPC22571
0.7733	Intermediate Similarity	NPC283875
0.7733	Intermediate Similarity	NPC469648
0.7733	Intermediate Similarity	NPC469647
0.773	Intermediate Similarity	NPC203486
0.7724	Intermediate Similarity	NPC51181
0.7717	Intermediate Similarity	NPC214067
0.7717	Intermediate Similarity	NPC93084
0.7717	Intermediate Similarity	NPC251854
0.7717	Intermediate Similarity	NPC196246
0.7698	Intermediate Similarity	NPC82712
0.7698	Intermediate Similarity	NPC147561
0.7674	Intermediate Similarity	NPC128368
0.7671	Intermediate Similarity	NPC95449
0.7667	Intermediate Similarity	NPC472398
0.7661	Intermediate Similarity	NPC474365
0.7661	Intermediate Similarity	NPC301943
0.7651	Intermediate Similarity	NPC473403
0.7643	Intermediate Similarity	NPC72915
0.7638	Intermediate Similarity	NPC265407
0.7638	Intermediate Similarity	NPC83628
0.7638	Intermediate Similarity	NPC17417
0.7638	Intermediate Similarity	NPC10251
0.7634	Intermediate Similarity	NPC149691
0.7616	Intermediate Similarity	NPC233581
0.7616	Intermediate Similarity	NPC145649
0.7609	Intermediate Similarity	NPC169913
0.7603	Intermediate Similarity	NPC182869
0.76	Intermediate Similarity	NPC254558
0.7591	Intermediate Similarity	NPC246166
0.7582	Intermediate Similarity	NPC11410
0.7571	Intermediate Similarity	NPC473247
0.7571	Intermediate Similarity	NPC471832
0.7568	Intermediate Similarity	NPC478264
0.7568	Intermediate Similarity	NPC127857
0.7559	Intermediate Similarity	NPC56493
0.7554	Intermediate Similarity	NPC115797
0.7554	Intermediate Similarity	NPC51448
0.7551	Intermediate Similarity	NPC477894
0.755	Intermediate Similarity	NPC471103
0.755	Intermediate Similarity	NPC51602
0.755	Intermediate Similarity	NPC161955
0.7536	Intermediate Similarity	NPC121272
0.7536	Intermediate Similarity	NPC275576
0.7534	Intermediate Similarity	NPC282973
0.7519	Intermediate Similarity	NPC94425
0.7518	Intermediate Similarity	NPC469519
0.7517	Intermediate Similarity	NPC9905
0.7517	Intermediate Similarity	NPC478263
0.7516	Intermediate Similarity	NPC251139
0.75	Intermediate Similarity	NPC470231
0.75	Intermediate Similarity	NPC226093
0.7484	Intermediate Similarity	NPC161151
0.7484	Intermediate Similarity	NPC159692
0.7483	Intermediate Similarity	NPC48929
0.7483	Intermediate Similarity	NPC471911
0.7483	Intermediate Similarity	NPC4242
0.7483	Intermediate Similarity	NPC474608
0.7482	Intermediate Similarity	NPC51292
0.7481	Intermediate Similarity	NPC153053
0.748	Intermediate Similarity	NPC119271
0.7467	Intermediate Similarity	NPC132652
0.7466	Intermediate Similarity	NPC87934
0.7466	Intermediate Similarity	NPC162613
0.7465	Intermediate Similarity	NPC475569
0.7465	Intermediate Similarity	NPC125153
0.7465	Intermediate Similarity	NPC472394
0.7465	Intermediate Similarity	NPC469499
0.7464	Intermediate Similarity	NPC295664
0.7448	Intermediate Similarity	NPC184109
0.7448	Intermediate Similarity	NPC475373
0.7442	Intermediate Similarity	NPC174099
0.7434	Intermediate Similarity	NPC306799
0.7434	Intermediate Similarity	NPC101043
0.7431	Intermediate Similarity	NPC477893
0.7431	Intermediate Similarity	NPC291638
0.7431	Intermediate Similarity	NPC477896
0.7431	Intermediate Similarity	NPC17877
0.7431	Intermediate Similarity	NPC66761
0.7431	Intermediate Similarity	NPC472577
0.7431	Intermediate Similarity	NPC195647
0.7421	Intermediate Similarity	NPC477491
0.7419	Intermediate Similarity	NPC325497
0.7419	Intermediate Similarity	NPC146351

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 NPC477360 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	280
0.1-0.2	892
0.2-0.3	1698
0.3-0.4	3078
0.4-0.5	2164
0.5-0.6	921
0.6-0.7	109
0.7-0.8	8
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.831	Intermediate Similarity	NPD7236	Approved
0.8027	Intermediate Similarity	NPD7239	Suspended
0.7795	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD2182	Approved
0.7548	Intermediate Similarity	NPD7058	Phase 2
0.7548	Intermediate Similarity	NPD7057	Phase 3
0.7442	Intermediate Similarity	NPD2067	Discontinued
0.7426	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD164	Approved
0.7293	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD7799	Discontinued
0.7226	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD7961	Discontinued
0.7143	Intermediate Similarity	NPD7094	Approved
0.7143	Intermediate Similarity	NPD6858	Approved
0.7122	Intermediate Similarity	NPD6287	Discontinued
0.7113	Intermediate Similarity	NPD6085	Phase 2
0.7113	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD6685	Approved
0.7068	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD1238	Approved
0.6977	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6912	Remote Similarity	NPD2629	Approved
0.6861	Remote Similarity	NPD4198	Discontinued
0.6846	Remote Similarity	NPD6647	Phase 2
0.6846	Remote Similarity	NPD5765	Approved
0.6842	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD7305	Phase 1
0.6752	Remote Similarity	NPD6273	Approved
0.6736	Remote Similarity	NPD1876	Approved
0.6735	Remote Similarity	NPD7008	Discontinued
0.6713	Remote Similarity	NPD3972	Approved
0.671	Remote Similarity	NPD3887	Approved
0.6691	Remote Similarity	NPD6912	Phase 3
0.669	Remote Similarity	NPD6362	Approved
0.6667	Remote Similarity	NPD6355	Discontinued
0.6667	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6002	Phase 3
0.6667	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6764	Approved
0.6667	Remote Similarity	NPD1237	Approved
0.6667	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6005	Phase 3
0.6667	Remote Similarity	NPD6004	Phase 3
0.6667	Remote Similarity	NPD6765	Approved
0.6645	Remote Similarity	NPD4628	Phase 3
0.6623	Remote Similarity	NPD6653	Approved
0.6621	Remote Similarity	NPD5667	Approved
0.6596	Remote Similarity	NPD7741	Discontinued
0.6596	Remote Similarity	NPD9545	Approved
0.6591	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD1930	Approved
0.6591	Remote Similarity	NPD1929	Approved
0.6584	Remote Similarity	NPD6599	Discontinued
0.6579	Remote Similarity	NPD2569	Approved
0.6579	Remote Similarity	NPD2567	Approved
0.6571	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.657	Remote Similarity	NPD8368	Discontinued
0.6564	Remote Similarity	NPD5761	Phase 2
0.6564	Remote Similarity	NPD5760	Phase 2
0.6558	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6554	Remote Similarity	NPD6832	Phase 2
0.6554	Remote Similarity	NPD7055	Discontinued
0.6552	Remote Similarity	NPD8407	Phase 2
0.6549	Remote Similarity	NPD5585	Approved
0.6547	Remote Similarity	NPD4766	Approved
0.6547	Remote Similarity	NPD5951	Approved
0.6533	Remote Similarity	NPD6663	Approved
0.6533	Remote Similarity	NPD7713	Phase 3
0.6531	Remote Similarity	NPD5647	Approved
0.6514	Remote Similarity	NPD6784	Approved
0.6514	Remote Similarity	NPD6785	Approved
0.6506	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7137	Phase 2
0.6489	Remote Similarity	NPD2066	Phase 3
0.6486	Remote Similarity	NPD5736	Approved
0.6484	Remote Similarity	NPD1202	Approved
0.6483	Remote Similarity	NPD6637	Approved
0.6479	Remote Similarity	NPD7009	Phase 2
0.6467	Remote Similarity	NPD3764	Approved
0.6463	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD9257	Approved
0.6452	Remote Similarity	NPD9259	Approved
0.6452	Remote Similarity	NPD2353	Approved
0.6452	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6434	Remote Similarity	NPD1693	Approved
0.6429	Remote Similarity	NPD2799	Discontinued
0.6424	Remote Similarity	NPD8032	Phase 2
0.642	Remote Similarity	NPD7458	Discontinued
0.6418	Remote Similarity	NPD5909	Discontinued
0.6415	Remote Similarity	NPD6799	Approved
0.6414	Remote Similarity	NPD4806	Approved
0.6414	Remote Similarity	NPD4807	Approved
0.6412	Remote Similarity	NPD9495	Approved
0.6408	Remote Similarity	NPD7610	Discontinued
0.64	Remote Similarity	NPD6039	Approved
0.6395	Remote Similarity	NPD2199	Approved
0.6395	Remote Similarity	NPD2198	Approved
0.6389	Remote Similarity	NPD5306	Approved
0.6389	Remote Similarity	NPD5305	Approved
0.6385	Remote Similarity	NPD1989	Approved
0.6384	Remote Similarity	NPD8434	Phase 2
0.6378	Remote Similarity	NPD3673	Approved
0.6378	Remote Similarity	NPD3672	Approved
0.6377	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6376	Remote Similarity	NPD3662	Phase 3
0.6376	Remote Similarity	NPD3664	Approved
0.6376	Remote Similarity	NPD3661	Approved
0.6376	Remote Similarity	NPD3663	Approved
0.6358	Remote Similarity	NPD2313	Discontinued
0.6357	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD2652	Approved
0.6357	Remote Similarity	NPD2650	Approved
0.6351	Remote Similarity	NPD3267	Approved
0.6351	Remote Similarity	NPD3266	Approved
0.6347	Remote Similarity	NPD7075	Discontinued
0.6346	Remote Similarity	NPD1471	Phase 3
0.6346	Remote Similarity	NPD5762	Approved
0.6346	Remote Similarity	NPD5763	Approved
0.634	Remote Similarity	NPD230	Phase 1
0.6338	Remote Similarity	NPD9493	Approved
0.6338	Remote Similarity	NPD4230	Clinical (unspecified phase)
0.6331	Remote Similarity	NPD969	Suspended
0.6327	Remote Similarity	NPD4359	Approved
0.6313	Remote Similarity	NPD8435	Approved
0.6309	Remote Similarity	NPD2798	Approved
0.6309	Remote Similarity	NPD1019	Discontinued
0.6309	Remote Similarity	NPD2788	Approved
0.6304	Remote Similarity	NPD4234	Approved
0.6304	Remote Similarity	NPD4233	Approved
0.6289	Remote Similarity	NPD2354	Approved
0.6289	Remote Similarity	NPD6190	Approved
0.6282	Remote Similarity	NPD2796	Approved
0.6279	Remote Similarity	NPD1088	Approved
0.6276	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6276	Remote Similarity	NPD17	Approved
0.6275	Remote Similarity	NPD4307	Phase 2
0.6273	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.627	Remote Similarity	NPD1087	Approved
0.6269	Remote Similarity	NPD1932	Approved
0.6266	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.625	Remote Similarity	NPD9258	Approved
0.625	Remote Similarity	NPD9256	Approved
0.625	Remote Similarity	NPD3268	Approved
0.6242	Remote Similarity	NPD2346	Discontinued
0.6241	Remote Similarity	NPD6010	Discontinued
0.6241	Remote Similarity	NPD7798	Approved
0.6241	Remote Similarity	NPD1241	Discontinued
0.6236	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6234	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6233	Remote Similarity	NPD4135	Approved
0.6233	Remote Similarity	NPD4136	Approved
0.6233	Remote Similarity	NPD4106	Approved
0.6232	Remote Similarity	NPD2329	Discontinued
0.6226	Remote Similarity	NPD8166	Discontinued
0.6222	Remote Similarity	NPD8361	Approved
0.6222	Remote Similarity	NPD8360	Approved
0.6209	Remote Similarity	NPD4870	Approved
0.6209	Remote Similarity	NPD6233	Phase 2
0.6207	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6205	Remote Similarity	NPD6801	Discontinued
0.6204	Remote Similarity	NPD3134	Approved
0.6196	Remote Similarity	NPD7606	Phase 3
0.6196	Remote Similarity	NPD920	Approved
0.6194	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.619	Remote Similarity	NPD518	Clinical (unspecified phase)
0.6187	Remote Similarity	NPD5237	Approved
0.6187	Remote Similarity	NPD1317	Discontinued
0.6187	Remote Similarity	NPD5235	Approved
0.6187	Remote Similarity	NPD5236	Approved
0.6187	Remote Similarity	NPD5240	Approved
0.6187	Remote Similarity	NPD5239	Approved
0.6184	Remote Similarity	NPD7095	Approved
0.6184	Remote Similarity	NPD2598	Clinical (unspecified phase)
0.6178	Remote Similarity	NPD2935	Discontinued
0.6173	Remote Similarity	NPD2534	Approved
0.6173	Remote Similarity	NPD2533	Approved
0.6173	Remote Similarity	NPD2532	Approved
0.6169	Remote Similarity	NPD2979	Phase 3
0.6169	Remote Similarity	NPD4140	Approved
0.6168	Remote Similarity	NPD7819	Suspended
0.6159	Remote Similarity	NPD7084	Phase 3
0.6159	Remote Similarity	NPD6881	Approved
0.6159	Remote Similarity	NPD5204	Approved
0.6159	Remote Similarity	NPD6899	Approved
0.6149	Remote Similarity	NPD9717	Approved
0.6149	Remote Similarity	NPD1608	Approved
0.6144	Remote Similarity	NPD6798	Discontinued
0.6143	Remote Similarity	NPD2201	Approved
0.6143	Remote Similarity	NPD6649	Approved
0.6143	Remote Similarity	NPD6650	Approved
0.614	Remote Similarity	NPD8127	Discontinued
0.6139	Remote Similarity	NPD7611	Approved
0.6133	Remote Similarity	NPD2797	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