NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	422.25
Volume:	458.028
LogP:	5.29
LogD:	4.526
LogS:	-5.227
# Rotatable Bonds:	3
TPSA:	63.6
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	5.061
Fsp3:	0.556
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.699
MDCK Permeability:	2.7515752663020976e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.015
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.042
30% Bioavailability (F30%):	0.058

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.406
Plasma Protein Binding (PPB):	99.5220718383789%
Volume Distribution (VD):	1.913
Pgp-substrate:	2.161860466003418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.347
CYP1A2-substrate:	0.256
CYP2C19-inhibitor:	0.82
CYP2C19-substrate:	0.444
CYP2C9-inhibitor:	0.935
CYP2C9-substrate:	0.561
CYP2D6-inhibitor:	0.345
CYP2D6-substrate:	0.134
CYP3A4-inhibitor:	0.928
CYP3A4-substrate:	0.513

ADMET: Excretion

Clearance (CL):	10.024
Half-life (T1/2):	0.1

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.832
Drug-inuced Liver Injury (DILI):	0.948
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.896
Maximum Recommended Daily Dose:	0.883
Skin Sensitization:	0.067
Carcinogencity:	0.139
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC477364

Natural Product ID:	NPC477364
*Common Name:**	[(1R,3E,5S,7S,10E,12S,13S,14S)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxo-1-tricyclo[10.3.0.05,7]pentadeca-3,10-dienyl] benzoate
IUPAC Name:	[(1R,3E,5S,7S,10E,12S,13S,14S)-13-hydroxy-3,6,6,10,14-pentamethyl-2-oxo-1-tricyclo[10.3.0.05,7]pentadeca-3,10-dienyl] benzoate
Synonyms:
Standard InCHIKey:	JQVANXRIXMMSKB-QBIOUWPCSA-N
Standard InCHI:	InChI=1S/C27H34O4/c1-16-11-12-20-21(26(20,4)5)14-17(2)24(29)27(15-18(3)23(28)22(27)13-16)31-25(30)19-9-7-6-8-10-19/h6-10,13-14,18,20-23,28H,11-12,15H2,1-5H3/b16-13+,17-14+/t18-,20-,21-,22-,23-,27+/m0/s1
SMILES:	C[C@H]1C[C@]2([C@H]([C@H]1O)/C=C(/CC[C@H]3[C@@H](C3(C)C)/C=C(/C2=O)\C)\C)OC(=O)C4=CC=CC=C4
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	56683353
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	=	42	%	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 NPC477364 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	268
0.1-0.2	1020
0.2-0.3	2303
0.3-0.4	6386
0.4-0.5	12130
0.5-0.6	14807
0.6-0.7	5048
0.7-0.8	564
0.8-0.85	41
0.85-0.9	91
0.9-0.95	30
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9921	High Similarity	NPC477368
0.9843	High Similarity	NPC232888
0.9843	High Similarity	NPC477367
0.9609	High Similarity	NPC477359
0.9603	High Similarity	NPC272946
0.9603	High Similarity	NPC42234
0.9453	High Similarity	NPC477360
0.944	High Similarity	NPC477363
0.9291	High Similarity	NPC477370
0.9286	High Similarity	NPC477366
0.928	High Similarity	NPC477362
0.9237	High Similarity	NPC270364
0.9219	High Similarity	NPC37968
0.9213	High Similarity	NPC477365
0.9167	High Similarity	NPC477358
0.9091	High Similarity	NPC472247
0.9062	High Similarity	NPC477357
0.9037	High Similarity	NPC473497
0.903	High Similarity	NPC276652
0.8976	High Similarity	NPC8990
0.8947	High Similarity	NPC265459
0.8947	High Similarity	NPC290833
0.8947	High Similarity	NPC475262
0.8929	High Similarity	NPC477099
0.8929	High Similarity	NPC477101
0.8929	High Similarity	NPC477097
0.8906	High Similarity	NPC477369
0.8905	High Similarity	NPC153214
0.8905	High Similarity	NPC45307
0.8897	High Similarity	NPC473654
0.8897	High Similarity	NPC474303
0.8897	High Similarity	NPC475413
0.8881	High Similarity	NPC194769
0.8881	High Similarity	NPC285221
0.8872	High Similarity	NPC472250
0.8815	High Similarity	NPC86772
0.8794	High Similarity	NPC125033
0.8794	High Similarity	NPC25484
0.8794	High Similarity	NPC232583
0.8786	High Similarity	NPC205389
0.8768	High Similarity	NPC477096
0.8768	High Similarity	NPC477094
0.875	High Similarity	NPC272523
0.875	High Similarity	NPC325805
0.8741	High Similarity	NPC477098
0.8741	High Similarity	NPC477100
0.8722	High Similarity	NPC233692
0.8722	High Similarity	NPC239358
0.8714	High Similarity	NPC170668
0.8686	High Similarity	NPC251294
0.8686	High Similarity	NPC475660
0.8657	High Similarity	NPC472248
0.8633	High Similarity	NPC82467
0.8593	High Similarity	NPC28836
0.8593	High Similarity	NPC311492
0.8582	High Similarity	NPC477095
0.8582	High Similarity	NPC233860
0.8571	High Similarity	NPC475671
0.8571	High Similarity	NPC475452
0.8529	High Similarity	NPC200154
0.8529	High Similarity	NPC79699
0.8489	Intermediate Similarity	NPC242355
0.8485	Intermediate Similarity	NPC472706
0.8467	Intermediate Similarity	NPC217673
0.8467	Intermediate Similarity	NPC52523
0.8467	Intermediate Similarity	NPC202729
0.8421	Intermediate Similarity	NPC472707
0.8406	Intermediate Similarity	NPC27721
0.8345	Intermediate Similarity	NPC473301
0.8298	Intermediate Similarity	NPC183540
0.8296	Intermediate Similarity	NPC122504
0.8296	Intermediate Similarity	NPC3450
0.8296	Intermediate Similarity	NPC475508
0.8295	Intermediate Similarity	NPC472708
0.8258	Intermediate Similarity	NPC472704
0.8227	Intermediate Similarity	NPC187566
0.8188	Intermediate Similarity	NPC329913
0.8188	Intermediate Similarity	NPC153617
0.8188	Intermediate Similarity	NPC126516
0.8182	Intermediate Similarity	NPC472703
0.8134	Intermediate Similarity	NPC476599
0.8125	Intermediate Similarity	NPC134131
0.8125	Intermediate Similarity	NPC25043
0.8125	Intermediate Similarity	NPC471162
0.8121	Intermediate Similarity	NPC70344
0.8092	Intermediate Similarity	NPC473243
0.8085	Intermediate Similarity	NPC170718
0.8058	Intermediate Similarity	NPC134937
0.8058	Intermediate Similarity	NPC324898
0.8058	Intermediate Similarity	NPC298547
0.8058	Intermediate Similarity	NPC203486
0.8054	Intermediate Similarity	NPC469456
0.8042	Intermediate Similarity	NPC51181
0.8041	Intermediate Similarity	NPC469648
0.8041	Intermediate Similarity	NPC138641
0.8041	Intermediate Similarity	NPC283875
0.8041	Intermediate Similarity	NPC469647
0.8041	Intermediate Similarity	NPC22571
0.8029	Intermediate Similarity	NPC82712
0.8	Intermediate Similarity	NPC469636
0.8	Intermediate Similarity	NPC279637
0.8	Intermediate Similarity	NPC149401
0.7986	Intermediate Similarity	NPC95449
0.7974	Intermediate Similarity	NPC55744
0.7973	Intermediate Similarity	NPC472398
0.7971	Intermediate Similarity	NPC72915
0.7941	Intermediate Similarity	NPC169913
0.7919	Intermediate Similarity	NPC145649
0.7919	Intermediate Similarity	NPC233581
0.7917	Intermediate Similarity	NPC182869
0.7887	Intermediate Similarity	NPC327511
0.7887	Intermediate Similarity	NPC205305
0.7881	Intermediate Similarity	NPC11410
0.7877	Intermediate Similarity	NPC478264
0.7868	Intermediate Similarity	NPC275576
0.7862	Intermediate Similarity	NPC191387
0.7862	Intermediate Similarity	NPC131966
0.7852	Intermediate Similarity	NPC471466
0.7852	Intermediate Similarity	NPC471103
0.7852	Intermediate Similarity	NPC161955
0.7842	Intermediate Similarity	NPC470278
0.7832	Intermediate Similarity	NPC9905
0.7832	Intermediate Similarity	NPC121268
0.7832	Intermediate Similarity	NPC53361
0.7829	Intermediate Similarity	NPC153053
0.7829	Intermediate Similarity	NPC307651
0.7823	Intermediate Similarity	NPC478263
0.7812	Intermediate Similarity	NPC270699
0.7812	Intermediate Similarity	NPC82899
0.7801	Intermediate Similarity	NPC48929
0.7794	Intermediate Similarity	NPC295664
0.7794	Intermediate Similarity	NPC246166
0.7793	Intermediate Similarity	NPC475135
0.7778	Intermediate Similarity	NPC162613
0.7778	Intermediate Similarity	NPC87934
0.7771	Intermediate Similarity	NPC161151
0.777	Intermediate Similarity	NPC132652
0.777	Intermediate Similarity	NPC471832
0.7761	Intermediate Similarity	NPC50872
0.7755	Intermediate Similarity	NPC127857
0.7754	Intermediate Similarity	NPC51448
0.7754	Intermediate Similarity	NPC115797
0.7752	Intermediate Similarity	NPC161611
0.7746	Intermediate Similarity	NPC477896
0.7746	Intermediate Similarity	NPC477893
0.7744	Intermediate Similarity	NPC204784
0.774	Intermediate Similarity	NPC477894
0.7734	Intermediate Similarity	NPC1082
0.7734	Intermediate Similarity	NPC305912
0.7733	Intermediate Similarity	NPC51602
0.7718	Intermediate Similarity	NPC250046
0.7718	Intermediate Similarity	NPC81698
0.7718	Intermediate Similarity	NPC60509
0.7697	Intermediate Similarity	NPC469730
0.7697	Intermediate Similarity	NPC251139
0.7697	Intermediate Similarity	NPC21410
0.7697	Intermediate Similarity	NPC473670
0.7697	Intermediate Similarity	NPC132599
0.7697	Intermediate Similarity	NPC473632
0.7692	Intermediate Similarity	NPC474363
0.7674	Intermediate Similarity	NPC321852
0.7671	Intermediate Similarity	NPC192658
0.7667	Intermediate Similarity	NPC198455
0.7667	Intermediate Similarity	NPC7095
0.7667	Intermediate Similarity	NPC165260
0.7667	Intermediate Similarity	NPC161239
0.7662	Intermediate Similarity	NPC159692
0.766	Intermediate Similarity	NPC125153
0.7656	Intermediate Similarity	NPC251854
0.7656	Intermediate Similarity	NPC93084
0.7656	Intermediate Similarity	NPC196246
0.7656	Intermediate Similarity	NPC214067
0.7647	Intermediate Similarity	NPC106895
0.7635	Intermediate Similarity	NPC471100
0.7635	Intermediate Similarity	NPC471107
0.7632	Intermediate Similarity	NPC219419
0.7616	Intermediate Similarity	NPC101043
0.7616	Intermediate Similarity	NPC306799
0.7606	Intermediate Similarity	NPC472656
0.7603	Intermediate Similarity	NPC266374
0.7603	Intermediate Similarity	NPC471862
0.76	Intermediate Similarity	NPC473215
0.76	Intermediate Similarity	NPC301943
0.76	Intermediate Similarity	NPC474365
0.7597	Intermediate Similarity	NPC260818
0.7597	Intermediate Similarity	NPC476003
0.7595	Intermediate Similarity	NPC477491
0.7584	Intermediate Similarity	NPC312393
0.7584	Intermediate Similarity	NPC475552
0.7584	Intermediate Similarity	NPC477737
0.7582	Intermediate Similarity	NPC259144
0.7582	Intermediate Similarity	NPC114357
0.7582	Intermediate Similarity	NPC282239
0.7582	Intermediate Similarity	NPC473611
0.7582	Intermediate Similarity	NPC155329
0.7578	Intermediate Similarity	NPC10251
0.7578	Intermediate Similarity	NPC17417
0.7578	Intermediate Similarity	NPC83628
0.7578	Intermediate Similarity	NPC265407
0.7568	Intermediate Similarity	NPC34943

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 NPC477364 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	222
0.1-0.2	774
0.2-0.3	1629
0.3-0.4	2859
0.4-0.5	2319
0.5-0.6	1083
0.6-0.7	244
0.7-0.8	19
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
0.8643	High Similarity	NPD7236	Approved
0.8345	Intermediate Similarity	NPD7239	Suspended
0.7843	Intermediate Similarity	NPD7058	Phase 2
0.7843	Intermediate Similarity	NPD7057	Phase 3
0.781	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7734	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2182	Approved
0.7516	Intermediate Similarity	NPD7799	Discontinued
0.75	Intermediate Similarity	NPD690	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD5738	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD5740	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6085	Phase 2
0.7422	Intermediate Similarity	NPD6685	Approved
0.7413	Intermediate Similarity	NPD7961	Discontinued
0.7385	Intermediate Similarity	NPD2067	Discontinued
0.7361	Intermediate Similarity	NPD7966	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD6647	Phase 2
0.7266	Intermediate Similarity	NPD164	Approved
0.7246	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD2629	Approved
0.7188	Intermediate Similarity	NPD5765	Approved
0.7176	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1237	Approved
0.7113	Intermediate Similarity	NPD6362	Approved
0.7059	Intermediate Similarity	NPD4198	Discontinued
0.705	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD7305	Phase 1
0.7032	Intermediate Similarity	NPD6273	Approved
0.7015	Intermediate Similarity	NPD6912	Phase 3
0.7015	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD7094	Approved
0.6963	Remote Similarity	NPD6858	Approved
0.6954	Remote Similarity	NPD6002	Phase 3
0.6954	Remote Similarity	NPD7702	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD6005	Phase 3
0.6954	Remote Similarity	NPD6004	Phase 3
0.6953	Remote Similarity	NPD1238	Approved
0.695	Remote Similarity	NPD6287	Discontinued
0.6944	Remote Similarity	NPD5647	Approved
0.6928	Remote Similarity	NPD4628	Phase 3
0.6923	Remote Similarity	NPD6765	Approved
0.6923	Remote Similarity	NPD6764	Approved
0.6918	Remote Similarity	NPD7008	Discontinued
0.6913	Remote Similarity	NPD6653	Approved
0.6906	Remote Similarity	NPD7741	Discontinued
0.6906	Remote Similarity	NPD9545	Approved
0.6875	Remote Similarity	NPD9495	Approved
0.6846	Remote Similarity	NPD6355	Discontinued
0.6832	Remote Similarity	NPD5760	Phase 2
0.6832	Remote Similarity	NPD5761	Phase 2
0.6824	Remote Similarity	NPD7685	Pre-registration
0.6824	Remote Similarity	NPD8368	Discontinued
0.6822	Remote Similarity	NPD2066	Phase 3
0.6821	Remote Similarity	NPD8424	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD8407	Phase 2
0.6794	Remote Similarity	NPD1931	Clinical (unspecified phase)
0.6794	Remote Similarity	NPD1930	Approved
0.6794	Remote Similarity	NPD1929	Approved
0.6776	Remote Similarity	NPD7137	Phase 2
0.6772	Remote Similarity	NPD1693	Approved
0.6763	Remote Similarity	NPD6784	Approved
0.6763	Remote Similarity	NPD6785	Approved
0.675	Remote Similarity	NPD6599	Discontinued
0.6739	Remote Similarity	NPD5951	Approved
0.6732	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD4807	Approved
0.6713	Remote Similarity	NPD4806	Approved
0.6711	Remote Similarity	NPD6663	Approved
0.6693	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD4141	Clinical (unspecified phase)
0.669	Remote Similarity	NPD5306	Approved
0.669	Remote Similarity	NPD5305	Approved
0.6667	Remote Similarity	NPD3661	Approved
0.6667	Remote Similarity	NPD2650	Approved
0.6667	Remote Similarity	NPD3972	Approved
0.6667	Remote Similarity	NPD2652	Approved
0.6667	Remote Similarity	NPD5736	Approved
0.6667	Remote Similarity	NPD3662	Phase 3
0.6667	Remote Similarity	NPD7009	Phase 2
0.6667	Remote Similarity	NPD6010	Discontinued
0.6667	Remote Similarity	NPD3887	Approved
0.6667	Remote Similarity	NPD3663	Approved
0.6667	Remote Similarity	NPD3664	Approved
0.6644	Remote Similarity	NPD3764	Approved
0.6643	Remote Similarity	NPD9493	Approved
0.6642	Remote Similarity	NPD969	Suspended
0.6629	Remote Similarity	NPD8434	Phase 2
0.6626	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD5763	Approved
0.6623	Remote Similarity	NPD5762	Approved
0.6617	Remote Similarity	NPD5909	Discontinued
0.6614	Remote Similarity	NPD1088	Approved
0.6601	Remote Similarity	NPD2799	Discontinued
0.6596	Remote Similarity	NPD7610	Discontinued
0.6587	Remote Similarity	NPD9258	Approved
0.6587	Remote Similarity	NPD9256	Approved
0.6584	Remote Similarity	NPD7458	Discontinued
0.6582	Remote Similarity	NPD6799	Approved
0.6575	Remote Similarity	NPD5667	Approved
0.6575	Remote Similarity	NPD1876	Approved
0.6567	Remote Similarity	NPD5048	Discontinued
0.6561	Remote Similarity	NPD6190	Approved
0.6561	Remote Similarity	NPD2354	Approved
0.6554	Remote Similarity	NPD8435	Approved
0.6541	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD2569	Approved
0.6536	Remote Similarity	NPD2567	Approved
0.6533	Remote Similarity	NPD3268	Approved
0.6533	Remote Similarity	NPD2313	Discontinued
0.6528	Remote Similarity	NPD4136	Approved
0.6528	Remote Similarity	NPD4135	Approved
0.6528	Remote Similarity	NPD4106	Approved
0.6513	Remote Similarity	NPD230	Phase 1
0.651	Remote Similarity	NPD6832	Phase 2
0.6506	Remote Similarity	NPD7075	Discontinued
0.6503	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6494	Remote Similarity	NPD7033	Discontinued
0.649	Remote Similarity	NPD7713	Phase 3
0.649	Remote Similarity	NPD6233	Phase 2
0.6471	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6899	Approved
0.6471	Remote Similarity	NPD6881	Approved
0.6466	Remote Similarity	NPD1932	Approved
0.6463	Remote Similarity	NPD6801	Discontinued
0.6461	Remote Similarity	NPD8360	Approved
0.6461	Remote Similarity	NPD8361	Approved
0.6458	Remote Similarity	NPD7163	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD1090	Approved
0.6457	Remote Similarity	NPD1089	Approved
0.6457	Remote Similarity	NPD1086	Approved
0.6453	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6649	Approved
0.6449	Remote Similarity	NPD6650	Approved
0.6447	Remote Similarity	NPD4140	Approved
0.6443	Remote Similarity	NPD5204	Approved
0.6438	Remote Similarity	NPD9717	Approved
0.6434	Remote Similarity	NPD1202	Approved
0.6424	Remote Similarity	NPD6798	Discontinued
0.6423	Remote Similarity	NPD2329	Discontinued
0.6419	Remote Similarity	NPD2797	Approved
0.641	Remote Similarity	NPD2353	Approved
0.641	Remote Similarity	NPD2346	Discontinued
0.641	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.64	Remote Similarity	NPD9259	Approved
0.64	Remote Similarity	NPD9257	Approved
0.64	Remote Similarity	NPD7055	Discontinued
0.6397	Remote Similarity	NPD5697	Approved
0.6392	Remote Similarity	NPD8166	Discontinued
0.6392	Remote Similarity	NPD7488	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD2575	Approved
0.6391	Remote Similarity	NPD8127	Discontinued
0.6389	Remote Similarity	NPD4102	Approved
0.6389	Remote Similarity	NPD4105	Approved
0.6389	Remote Similarity	NPD5585	Approved
0.6384	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD4766	Approved
0.6382	Remote Similarity	NPD7715	Approved
0.6382	Remote Similarity	NPD7714	Approved
0.638	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6378	Remote Similarity	NPD800	Approved
0.6377	Remote Similarity	NPD1317	Discontinued
0.6377	Remote Similarity	NPD7102	Approved
0.6377	Remote Similarity	NPD7290	Approved
0.6377	Remote Similarity	NPD6883	Approved
0.6376	Remote Similarity	NPD2798	Approved
0.6369	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6358	Remote Similarity	NPD6039	Approved
0.6358	Remote Similarity	NPD7095	Approved
0.6358	Remote Similarity	NPD5403	Approved
0.6351	Remote Similarity	NPD2198	Approved
0.6351	Remote Similarity	NPD2199	Approved
0.635	Remote Similarity	NPD6406	Approved
0.6348	Remote Similarity	NPD8150	Discontinued
0.6346	Remote Similarity	NPD2935	Discontinued
0.6339	Remote Similarity	NPD8485	Approved
0.6336	Remote Similarity	NPD1989	Approved
0.6335	Remote Similarity	NPD2534	Approved
0.6335	Remote Similarity	NPD5401	Approved
0.6335	Remote Similarity	NPD2532	Approved
0.6335	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6335	Remote Similarity	NPD2533	Approved
0.6331	Remote Similarity	NPD8130	Phase 1
0.6331	Remote Similarity	NPD6847	Approved
0.6331	Remote Similarity	NPD6617	Approved
0.6331	Remote Similarity	NPD6869	Approved
0.6328	Remote Similarity	NPD3673	Approved
0.6328	Remote Similarity	NPD5785	Approved
0.6328	Remote Similarity	NPD3672	Approved
0.6327	Remote Similarity	NPD6637	Approved
0.6327	Remote Similarity	NPD1608	Approved
0.6325	Remote Similarity	NPD7819	Suspended
0.6324	Remote Similarity	NPD6675	Approved
0.6324	Remote Similarity	NPD7128	Approved
0.6324	Remote Similarity	NPD6402	Approved
0.6324	Remote Similarity	NPD5739	Approved
0.6316	Remote Similarity	NPD6859	Clinical (unspecified phase)

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