NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	542.27
Volume:	571.658
LogP:	6.384
LogD:	5.117
LogS:	-4.911
# Rotatable Bonds:	6
TPSA:	82.2
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.338
Synthetic Accessibility Score:	5.05
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.981
MDCK Permeability:	2.488042628101539e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.213
30% Bioavailability (F30%):	0.626

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	99.57149505615234%
Volume Distribution (VD):	2.29
Pgp-substrate:	3.0652973651885986%

ADMET: Metabolism

CYP1A2-inhibitor:	0.072
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.464
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.613
CYP2C9-substrate:	0.111
CYP2D6-inhibitor:	0.256
CYP2D6-substrate:	0.08
CYP3A4-inhibitor:	0.888
CYP3A4-substrate:	0.576

ADMET: Excretion

Clearance (CL):	8.53
Half-life (T1/2):	0.111

ADMET: Toxicity

hERG Blockers:	0.923
Human Hepatotoxicity (H-HT):	0.912
Drug-inuced Liver Injury (DILI):	0.779
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.425
Maximum Recommended Daily Dose:	0.758
Skin Sensitization:	0.938
Carcinogencity:	0.085
Eye Corrosion:	0.003
Eye Irritation:	0.031
Respiratory Toxicity:	0.676

Download Data

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

Natural Product: NPC477358

Natural Product ID:	NPC477358
*Common Name:**	[(1R,2R,4R,7S,9S,10E,13R,15S,16S)-13-benzoyloxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-16-yl] benzoate
IUPAC Name:	[(1R,2R,4R,7S,9S,10E,13R,15S,16S)-13-benzoyloxy-4,8,8,11,15-pentamethyl-12-oxo-3-oxatetracyclo[11.3.0.02,4.07,9]hexadec-10-en-16-yl] benzoate
Synonyms:
Standard InCHIKey:	KIJAQQYGTDMBNC-WZJYHAIHSA-N
Standard InCHI:	InChI=1S/C34H38O6/c1-20-18-25-24(32(25,3)4)16-17-33(5)29(39-33)26-27(38-30(36)22-12-8-6-9-13-22)21(2)19-34(26,28(20)35)40-31(37)23-14-10-7-11-15-23/h6-15,18,21,24-27,29H,16-17,19H2,1-5H3/b20-18+/t21-,24-,25-,26+,27-,29+,33+,34+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1OC(=O)C3=CC=CC=C3)[C@@H]4[C@](O4)(CC[C@H]5[C@@H](C5(C)C)/C=C(/C2=O)\C)C)OC(=O)C6=CC=CC=C6
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56673372
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	<	30	%	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 NPC477358 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	345
0.1-0.2	1350
0.2-0.3	2580
0.3-0.4	7410
0.4-0.5	13122
0.5-0.6	13907
0.6-0.7	3530
0.7-0.8	316
0.8-0.85	57
0.85-0.9	61
0.9-0.95	16
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9697	High Similarity	NPC473654
0.9688	High Similarity	NPC477360
0.9545	High Similarity	NPC276652
0.9531	High Similarity	NPC42234
0.9389	High Similarity	NPC477359
0.9343	High Similarity	NPC477095
0.9318	High Similarity	NPC270364
0.9265	High Similarity	NPC82467
0.9242	High Similarity	NPC477368
0.9185	High Similarity	NPC475660
0.9173	High Similarity	NPC232888
0.9173	High Similarity	NPC477367
0.9167	High Similarity	NPC477364
0.9124	High Similarity	NPC477096
0.9124	High Similarity	NPC477094
0.9062	High Similarity	NPC8990
0.903	High Similarity	NPC475262
0.903	High Similarity	NPC290833
0.903	High Similarity	NPC265459
0.8992	High Similarity	NPC477369
0.8963	High Similarity	NPC285221
0.8963	High Similarity	NPC194769
0.8955	High Similarity	NPC472250
0.8951	High Similarity	NPC477100
0.8951	High Similarity	NPC477098
0.8939	High Similarity	NPC272946
0.8939	High Similarity	NPC475452
0.8939	High Similarity	NPC475671
0.8905	High Similarity	NPC251294
0.8897	High Similarity	NPC86772
0.8873	High Similarity	NPC25484
0.8873	High Similarity	NPC232583
0.8864	High Similarity	NPC37968
0.8855	High Similarity	NPC477357
0.8832	High Similarity	NPC325805
0.8832	High Similarity	NPC272523
0.875	High Similarity	NPC472247
0.8741	High Similarity	NPC477099
0.8741	High Similarity	NPC125033
0.8741	High Similarity	NPC477097
0.8741	High Similarity	NPC477101
0.8732	High Similarity	NPC205389
0.8714	High Similarity	NPC153214
0.8705	High Similarity	NPC473497
0.8676	High Similarity	NPC153617
0.8657	High Similarity	NPC3450
0.8657	High Similarity	NPC122504
0.8647	High Similarity	NPC477370
0.8636	High Similarity	NPC477363
0.8636	High Similarity	NPC477366
0.8626	High Similarity	NPC477362
0.8613	High Similarity	NPC79699
0.8582	High Similarity	NPC45307
0.8571	High Similarity	NPC474303
0.8571	High Similarity	NPC475413
0.8571	High Similarity	NPC477365
0.844	Intermediate Similarity	NPC242355
0.844	Intermediate Similarity	NPC187566
0.8403	Intermediate Similarity	NPC170668
0.8382	Intermediate Similarity	NPC475508
0.8357	Intermediate Similarity	NPC205305
0.8357	Intermediate Similarity	NPC327511
0.8321	Intermediate Similarity	NPC473243
0.8298	Intermediate Similarity	NPC473301
0.8298	Intermediate Similarity	NPC121268
0.8298	Intermediate Similarity	NPC53361
0.8273	Intermediate Similarity	NPC324898
0.8273	Intermediate Similarity	NPC134937
0.8273	Intermediate Similarity	NPC298547
0.8261	Intermediate Similarity	NPC233860
0.8222	Intermediate Similarity	NPC476599
0.8214	Intermediate Similarity	NPC279637
0.8214	Intermediate Similarity	NPC149401
0.8201	Intermediate Similarity	NPC472248
0.8194	Intermediate Similarity	NPC131966
0.8194	Intermediate Similarity	NPC191387
0.8188	Intermediate Similarity	NPC470278
0.8143	Intermediate Similarity	NPC28836
0.8129	Intermediate Similarity	NPC239358
0.8129	Intermediate Similarity	NPC233692
0.8125	Intermediate Similarity	NPC183540
0.8125	Intermediate Similarity	NPC475135
0.8085	Intermediate Similarity	NPC200154
0.8082	Intermediate Similarity	NPC25043
0.8082	Intermediate Similarity	NPC134131
0.8079	Intermediate Similarity	NPC70344
0.8052	Intermediate Similarity	NPC55744
0.8028	Intermediate Similarity	NPC202729
0.8014	Intermediate Similarity	NPC311492
0.8014	Intermediate Similarity	NPC329913
0.7972	Intermediate Similarity	NPC27721
0.7959	Intermediate Similarity	NPC471162
0.7943	Intermediate Similarity	NPC472656
0.7905	Intermediate Similarity	NPC475552
0.7902	Intermediate Similarity	NPC217673
0.7902	Intermediate Similarity	NPC52523
0.7899	Intermediate Similarity	NPC472706
0.7887	Intermediate Similarity	NPC203486
0.7887	Intermediate Similarity	NPC126516
0.7881	Intermediate Similarity	NPC22571
0.7881	Intermediate Similarity	NPC469647
0.7881	Intermediate Similarity	NPC283875
0.7881	Intermediate Similarity	NPC138641
0.7881	Intermediate Similarity	NPC469648
0.7872	Intermediate Similarity	NPC238370
0.7867	Intermediate Similarity	NPC254558
0.7852	Intermediate Similarity	NPC50872
0.7842	Intermediate Similarity	NPC472707
0.7838	Intermediate Similarity	NPC471100
0.7838	Intermediate Similarity	NPC471107
0.7823	Intermediate Similarity	NPC95449
0.7812	Intermediate Similarity	NPC469636
0.781	Intermediate Similarity	NPC472704
0.78	Intermediate Similarity	NPC473403
0.7786	Intermediate Similarity	NPC307651
0.7778	Intermediate Similarity	NPC469456
0.777	Intermediate Similarity	NPC470231
0.7763	Intermediate Similarity	NPC233581
0.7763	Intermediate Similarity	NPC145649
0.7737	Intermediate Similarity	NPC472703
0.773	Intermediate Similarity	NPC471832
0.773	Intermediate Similarity	NPC147561
0.7727	Intermediate Similarity	NPC11410
0.771	Intermediate Similarity	NPC128368
0.7704	Intermediate Similarity	NPC472708
0.7697	Intermediate Similarity	NPC472398
0.7697	Intermediate Similarity	NPC51602
0.7687	Intermediate Similarity	NPC266374
0.7676	Intermediate Similarity	NPC72915
0.7662	Intermediate Similarity	NPC251139
0.7662	Intermediate Similarity	NPC282239
0.7643	Intermediate Similarity	NPC169913
0.7639	Intermediate Similarity	NPC471911
0.7639	Intermediate Similarity	NPC4242
0.7635	Intermediate Similarity	NPC182869
0.7634	Intermediate Similarity	NPC270699
0.7634	Intermediate Similarity	NPC82899
0.7626	Intermediate Similarity	NPC295664
0.7622	Intermediate Similarity	NPC167340
0.7622	Intermediate Similarity	NPC472394
0.7619	Intermediate Similarity	NPC162613
0.7619	Intermediate Similarity	NPC87934
0.7613	Intermediate Similarity	NPC217091
0.7613	Intermediate Similarity	NPC106895
0.7606	Intermediate Similarity	NPC82712
0.7606	Intermediate Similarity	NPC473247
0.7603	Intermediate Similarity	NPC475373
0.7603	Intermediate Similarity	NPC184109
0.76	Intermediate Similarity	NPC127857
0.76	Intermediate Similarity	NPC478264
0.7589	Intermediate Similarity	NPC115797
0.7589	Intermediate Similarity	NPC51448
0.7584	Intermediate Similarity	NPC477894
0.7582	Intermediate Similarity	NPC471103
0.7578	Intermediate Similarity	NPC40138
0.7576	Intermediate Similarity	NPC161611
0.7571	Intermediate Similarity	NPC275576
0.7568	Intermediate Similarity	NPC471862
0.7566	Intermediate Similarity	NPC473215
0.7564	Intermediate Similarity	NPC472393
0.7562	Intermediate Similarity	NPC477491
0.7557	Intermediate Similarity	NPC305912
0.7557	Intermediate Similarity	NPC1082
0.7551	Intermediate Similarity	NPC210591
0.7551	Intermediate Similarity	NPC9905
0.7551	Intermediate Similarity	NPC214550
0.7551	Intermediate Similarity	NPC170718
0.7551	Intermediate Similarity	NPC475652
0.755	Intermediate Similarity	NPC478263
0.7548	Intermediate Similarity	NPC21410
0.7548	Intermediate Similarity	NPC473611
0.7548	Intermediate Similarity	NPC473670
0.7537	Intermediate Similarity	NPC149691
0.7518	Intermediate Similarity	NPC48992
0.7518	Intermediate Similarity	NPC473220
0.7518	Intermediate Similarity	NPC470753
0.7517	Intermediate Similarity	NPC472546
0.7517	Intermediate Similarity	NPC51181
0.7517	Intermediate Similarity	NPC474608
0.7517	Intermediate Similarity	NPC192658
0.7517	Intermediate Similarity	NPC471856
0.7517	Intermediate Similarity	NPC48929
0.7516	Intermediate Similarity	NPC112216
0.7516	Intermediate Similarity	NPC470245
0.7516	Intermediate Similarity	NPC473214
0.7516	Intermediate Similarity	NPC161151
0.7516	Intermediate Similarity	NPC471102
0.7516	Intermediate Similarity	NPC7095
0.7516	Intermediate Similarity	NPC159692
0.75	Intermediate Similarity	NPC184747
0.75	Intermediate Similarity	NPC475569
0.75	Intermediate Similarity	NPC200592
0.75	Intermediate Similarity	NPC473112
0.75	Intermediate Similarity	NPC4341
0.75	Intermediate Similarity	NPC473081
0.75	Intermediate Similarity	NPC473109
0.75	Intermediate Similarity	NPC475400
0.75	Intermediate Similarity	NPC471863
0.75	Intermediate Similarity	NPC473758
0.75	Intermediate Similarity	NPC473613

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 NPC477358 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	283
0.1-0.2	864
0.2-0.3	1524
0.3-0.4	2986
0.4-0.5	2331
0.5-0.6	987
0.6-0.7	166
0.7-0.8	9
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
0.8333	Intermediate Similarity	NPD7236	Approved
0.8054	Intermediate Similarity	NPD7239	Suspended
0.758	Intermediate Similarity	NPD7057	Phase 3
0.758	Intermediate Similarity	NPD7058	Phase 2
0.7557	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7464	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2182	Approved
0.7394	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7379	Intermediate Similarity	NPD7961	Discontinued
0.7378	Intermediate Similarity	NPD7799	Discontinued
0.7286	Intermediate Similarity	NPD6287	Discontinued
0.7266	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7218	Intermediate Similarity	NPD2067	Discontinued
0.7188	Intermediate Similarity	NPD1238	Approved
0.7185	Intermediate Similarity	NPD6858	Approved
0.7185	Intermediate Similarity	NPD7094	Approved
0.7123	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD164	Approved
0.7095	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.708	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD2629	Approved
0.6928	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD6085	Phase 2
0.6906	Remote Similarity	NPD4198	Discontinued
0.6901	Remote Similarity	NPD7685	Pre-registration
0.6899	Remote Similarity	NPD6273	Approved
0.6897	Remote Similarity	NPD1876	Approved
0.6892	Remote Similarity	NPD7008	Discontinued
0.6875	Remote Similarity	NPD3972	Approved
0.6866	Remote Similarity	NPD6685	Approved
0.6859	Remote Similarity	NPD3887	Approved
0.6842	Remote Similarity	NPD1237	Approved
0.6821	Remote Similarity	NPD6355	Discontinued
0.68	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7713	Phase 3
0.6797	Remote Similarity	NPD7305	Phase 1
0.6795	Remote Similarity	NPD4628	Phase 3
0.6781	Remote Similarity	NPD5667	Approved
0.6767	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1929	Approved
0.6767	Remote Similarity	NPD5738	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD1930	Approved
0.6765	Remote Similarity	NPD6831	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD7741	Discontinued
0.6728	Remote Similarity	NPD6599	Discontinued
0.6714	Remote Similarity	NPD5951	Approved
0.6713	Remote Similarity	NPD5585	Approved
0.6711	Remote Similarity	NPD6832	Phase 2
0.671	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD6764	Approved
0.6705	Remote Similarity	NPD6765	Approved
0.6705	Remote Similarity	NPD8368	Discontinued
0.6686	Remote Similarity	NPD8407	Phase 2
0.6667	Remote Similarity	NPD1202	Approved
0.6642	Remote Similarity	NPD6647	Phase 2
0.6642	Remote Similarity	NPD5765	Approved
0.6623	Remote Similarity	NPD3764	Approved
0.661	Remote Similarity	NPD8434	Phase 2
0.6606	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5761	Phase 2
0.6606	Remote Similarity	NPD5760	Phase 2
0.6603	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD2353	Approved
0.66	Remote Similarity	NPD7055	Discontinued
0.6593	Remote Similarity	NPD5909	Discontinued
0.6581	Remote Similarity	NPD2799	Discontinued
0.6579	Remote Similarity	NPD6663	Approved
0.6579	Remote Similarity	NPD8032	Phase 2
0.6565	Remote Similarity	NPD1989	Approved
0.6564	Remote Similarity	NPD7458	Discontinued
0.6562	Remote Similarity	NPD6799	Approved
0.6556	Remote Similarity	NPD6039	Approved
0.6554	Remote Similarity	NPD6784	Approved
0.6554	Remote Similarity	NPD6785	Approved
0.6541	Remote Similarity	NPD2066	Phase 3
0.6541	Remote Similarity	NPD7798	Approved
0.6536	Remote Similarity	NPD8435	Approved
0.6533	Remote Similarity	NPD5736	Approved
0.6528	Remote Similarity	NPD7009	Phase 2
0.6516	Remote Similarity	NPD2569	Approved
0.6516	Remote Similarity	NPD2567	Approved
0.6513	Remote Similarity	NPD2313	Discontinued
0.651	Remote Similarity	NPD6362	Approved
0.651	Remote Similarity	NPD3266	Approved
0.651	Remote Similarity	NPD3267	Approved
0.65	Remote Similarity	NPD6912	Phase 3
0.6497	Remote Similarity	NPD1471	Phase 3
0.6497	Remote Similarity	NPD6005	Phase 3
0.6497	Remote Similarity	NPD6002	Phase 3
0.6497	Remote Similarity	NPD6004	Phase 3
0.6497	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD7075	Discontinued
0.6486	Remote Similarity	NPD4359	Approved
0.6467	Remote Similarity	NPD2788	Approved
0.6467	Remote Similarity	NPD2798	Approved
0.6463	Remote Similarity	NPD4806	Approved
0.6463	Remote Similarity	NPD4807	Approved
0.6461	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD7610	Discontinued
0.6452	Remote Similarity	NPD6653	Approved
0.645	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD1932	Approved
0.6444	Remote Similarity	NPD8360	Approved
0.6444	Remote Similarity	NPD8361	Approved
0.6443	Remote Similarity	NPD2198	Approved
0.6443	Remote Similarity	NPD2199	Approved
0.6438	Remote Similarity	NPD6190	Approved
0.6438	Remote Similarity	NPD5306	Approved
0.6438	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD17	Approved
0.6438	Remote Similarity	NPD5305	Approved
0.6438	Remote Similarity	NPD2354	Approved
0.6433	Remote Similarity	NPD7137	Phase 2
0.6433	Remote Similarity	NPD2796	Approved
0.6429	Remote Similarity	NPD4307	Phase 2
0.642	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD6637	Approved
0.6415	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD9545	Approved
0.6407	Remote Similarity	NPD7819	Suspended
0.6405	Remote Similarity	NPD3268	Approved
0.6403	Remote Similarity	NPD2329	Discontinued
0.6395	Remote Similarity	NPD4136	Approved
0.6395	Remote Similarity	NPD4106	Approved
0.6395	Remote Similarity	NPD4135	Approved
0.6392	Remote Similarity	NPD5763	Approved
0.6392	Remote Similarity	NPD2346	Discontinued
0.6392	Remote Similarity	NPD5762	Approved
0.6387	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD8166	Discontinued
0.6364	Remote Similarity	NPD7714	Approved
0.6364	Remote Similarity	NPD6233	Phase 2
0.6364	Remote Similarity	NPD4870	Approved
0.6364	Remote Similarity	NPD4766	Approved
0.6364	Remote Similarity	NPD7715	Approved
0.6358	Remote Similarity	NPD5647	Approved
0.6357	Remote Similarity	NPD5239	Approved
0.6357	Remote Similarity	NPD5235	Approved
0.6357	Remote Similarity	NPD5236	Approved
0.6357	Remote Similarity	NPD5240	Approved
0.6357	Remote Similarity	NPD5237	Approved
0.6351	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6801	Discontinued
0.6346	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.634	Remote Similarity	NPD7095	Approved
0.6333	Remote Similarity	NPD8150	Discontinued
0.6329	Remote Similarity	NPD2935	Discontinued
0.6324	Remote Similarity	NPD8485	Approved
0.6323	Remote Similarity	NPD2979	Phase 3
0.6316	Remote Similarity	NPD5204	Approved
0.6312	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.6309	Remote Similarity	NPD1608	Approved
0.6304	Remote Similarity	NPD5048	Discontinued
0.6299	Remote Similarity	NPD6798	Discontinued
0.6291	Remote Similarity	NPD2797	Approved
0.6289	Remote Similarity	NPD7611	Approved
0.6288	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD8127	Discontinued
0.6273	Remote Similarity	NPD7003	Approved
0.6273	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6272	Remote Similarity	NPD3817	Phase 2
0.6272	Remote Similarity	NPD5402	Approved
0.6266	Remote Similarity	NPD7033	Discontinued
0.6266	Remote Similarity	NPD3748	Approved
0.6266	Remote Similarity	NPD4308	Phase 3
0.6265	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6259	Remote Similarity	NPD4102	Approved
0.6259	Remote Similarity	NPD4105	Approved
0.625	Remote Similarity	NPD9259	Approved
0.625	Remote Similarity	NPD4534	Discontinued
0.625	Remote Similarity	NPD5958	Discontinued
0.625	Remote Similarity	NPD9257	Approved
0.6243	Remote Similarity	NPD6808	Phase 2
0.6242	Remote Similarity	NPD920	Approved
0.6242	Remote Similarity	NPD7606	Phase 3
0.6242	Remote Similarity	NPD5403	Approved
0.6242	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6241	Remote Similarity	NPD1693	Approved
0.6233	Remote Similarity	NPD6065	Approved
0.6233	Remote Similarity	NPD2347	Approved
0.6226	Remote Similarity	NPD2438	Suspended
0.6223	Remote Similarity	NPD8486	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD5926	Approved
0.6222	Remote Similarity	NPD9495	Approved
0.6221	Remote Similarity	NPD5494	Approved
0.622	Remote Similarity	NPD5401	Approved
0.622	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD4140	Approved
0.6218	Remote Similarity	NPD3373	Approved
0.6214	Remote Similarity	NPD6881	Approved
0.6214	Remote Similarity	NPD6899	Approved
0.6212	Remote Similarity	NPD1508	Approved
0.6209	Remote Similarity	NPD3661	Approved
0.6209	Remote Similarity	NPD3662	Phase 3
0.6209	Remote Similarity	NPD3664	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