NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	344.865
LogP:	3.406
LogD:	3.332
LogS:	-4.613
# Rotatable Bonds:	1
TPSA:	56.51
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.72
Synthetic Accessibility Score:	4.472
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.7
MDCK Permeability:	2.359924474149011e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.05
30% Bioavailability (F30%):	0.857

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.719
Plasma Protein Binding (PPB):	92.0824203491211%
Volume Distribution (VD):	1.447
Pgp-substrate:	7.44027853012085%

ADMET: Metabolism

CYP1A2-inhibitor:	0.089
CYP1A2-substrate:	0.377
CYP2C19-inhibitor:	0.372
CYP2C19-substrate:	0.494
CYP2C9-inhibitor:	0.41
CYP2C9-substrate:	0.107
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.679
CYP3A4-inhibitor:	0.758
CYP3A4-substrate:	0.327

ADMET: Excretion

Clearance (CL):	12.294
Half-life (T1/2):	0.249

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.341
Drug-inuced Liver Injury (DILI):	0.24
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.972
Maximum Recommended Daily Dose:	0.898
Skin Sensitization:	0.097
Carcinogencity:	0.537
Eye Corrosion:	0.021
Eye Irritation:	0.07
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC476943

Natural Product ID:	NPC476943
*Common Name:**	(2S,4aR,6aR,7S,10aS,10bR)-2-(furan-3-yl)-6a,7,10b-trimethyl-2,4a,5,6,7,9,10,10a-octahydro-1H-benzo[f]isochromene-4,8-dione
IUPAC Name:	(2S,4aR,6aR,7S,10aS,10bR)-2-(furan-3-yl)-6a,7,10b-trimethyl-2,4a,5,6,7,9,10,10a-octahydro-1H-benzo[f]isochromene-4,8-dione
Synonyms:
Standard InCHIKey:	YXIXITUSOJUAND-VZXMROHQSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-12-15(21)4-5-17-19(12,2)8-6-14-18(22)24-16(10-20(14,17)3)13-7-9-23-11-13/h7,9,11-12,14,16-17H,4-6,8,10H2,1-3H3/t12-,14+,16+,17+,19+,20+/m1/s1
SMILES:	C[C@@H]1C(=O)CC[C@H]2[C@]1(CC[C@@H]3[C@@]2(C[C@H](OC3=O)C4=COC=C4)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90676772
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene lactones

*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
NPO33579	Croton laui	Species	Euphorbiaceae	Eukaryota	Twigs	Hainan Province, China	n.a.	PMID[24735527]

☑ 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
IC50	2
MIC	11

Activity Type	# Activity
Cell Line	2
Organism	10
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>=	10000	nM	PMID[24735527]
NPT168	Cell Line	P388	Mus musculus	IC50	>=	10000	nM	PMID[24735527]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	150000	nM	PMID[24735527]
NPT1277	Organism	Staphylococcus epidermidis ATCC 12228	Staphylococcus epidermidis ATCC 12228	MIC	>	150000	nM	PMID[24735527]
NPT2	Others	Unspecified		MIC	>	150000	nM	PMID[24735527]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	>	150000	nM	PMID[24735527]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	150000	nM	PMID[24735527]
NPT2909	Organism	Shigella flexneri	Shigella flexneri	MIC	>	150000	nM	PMID[24735527]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	150000	nM	PMID[24735527]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	150000	nM	PMID[24735527]
NPT1533	Organism	Saccharomyces	Saccharomyces	MIC	>	150000	nM	PMID[24735527]
NPT327	Organism	Microsporum gypseum	Microsporum gypseum	MIC	>	150000	nM	PMID[24735527]
NPT329	Organism	Trichophyton rubrum	Trichophyton rubrum	MIC	>	150000	nM	PMID[24735527]

☑ 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 NPC476943 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	350
0.1-0.2	1398
0.2-0.3	2844
0.3-0.4	6127
0.4-0.5	12013
0.5-0.6	9857
0.6-0.7	8818
0.7-0.8	906
0.8-0.85	291
0.85-0.9	76
0.9-0.95	14
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9771	High Similarity	NPC310830
0.9697	High Similarity	NPC220094
0.9559	High Similarity	NPC142113
0.942	High Similarity	NPC262198
0.9416	High Similarity	NPC476944
0.9203	High Similarity	NPC267632
0.9185	High Similarity	NPC42400
0.9179	High Similarity	NPC92941
0.9155	High Similarity	NPC477404
0.9155	High Similarity	NPC469335
0.9155	High Similarity	NPC46551
0.9155	High Similarity	NPC196864
0.9155	High Similarity	NPC159927
0.9143	High Similarity	NPC346
0.9078	High Similarity	NPC470941
0.9078	High Similarity	NPC250228
0.9077	High Similarity	NPC74612
0.9044	High Similarity	NPC470742
0.9021	High Similarity	NPC476122
0.9	High Similarity	NPC179354
0.8971	High Similarity	NPC146872
0.8966	High Similarity	NPC178932
0.8947	High Similarity	NPC21460
0.8944	High Similarity	NPC221809
0.8929	High Similarity	NPC223415
0.8929	High Similarity	NPC470741
0.8921	High Similarity	NPC20500
0.8904	High Similarity	NPC469850
0.8904	High Similarity	NPC281258
0.8904	High Similarity	NPC469336
0.8897	High Similarity	NPC476201
0.8897	High Similarity	NPC469503
0.8849	High Similarity	NPC56197
0.8846	High Similarity	NPC16922
0.8844	High Similarity	NPC263265
0.8844	High Similarity	NPC107646
0.8844	High Similarity	NPC209364
0.8844	High Similarity	NPC60973
0.8836	High Similarity	NPC282445
0.8836	High Similarity	NPC30222
0.8819	High Similarity	NPC195325
0.8811	High Similarity	NPC10088
0.8786	High Similarity	NPC205765
0.8784	High Similarity	NPC167142
0.8784	High Similarity	NPC249021
0.8784	High Similarity	NPC286722
0.8784	High Similarity	NPC472283
0.8784	High Similarity	NPC472772
0.8776	High Similarity	NPC35000
0.8776	High Similarity	NPC264943
0.8776	High Similarity	NPC476262
0.8767	High Similarity	NPC75906
0.8759	High Similarity	NPC156189
0.875	High Similarity	NPC470740
0.875	High Similarity	NPC476941
0.875	High Similarity	NPC476942
0.8741	High Similarity	NPC471292
0.8741	High Similarity	NPC62799
0.8732	High Similarity	NPC199044
0.8732	High Similarity	NPC238843
0.8725	High Similarity	NPC473473
0.8725	High Similarity	NPC475295
0.8725	High Similarity	NPC237155
0.8722	High Similarity	NPC319140
0.8722	High Similarity	NPC95567
0.8716	High Similarity	NPC126723
0.8707	High Similarity	NPC57998
0.8705	High Similarity	NPC236532
0.8699	High Similarity	NPC18135
0.869	High Similarity	NPC472654
0.8681	High Similarity	NPC476938
0.8681	High Similarity	NPC476937
0.8676	High Similarity	NPC471817
0.8667	High Similarity	NPC305016
0.8667	High Similarity	NPC475381
0.8667	High Similarity	NPC25255
0.8658	High Similarity	NPC299038
0.8649	High Similarity	NPC214541
0.8649	High Similarity	NPC44675
0.8647	High Similarity	NPC138139
0.8647	High Similarity	NPC46536
0.8643	High Similarity	NPC474722
0.8639	High Similarity	NPC44577
0.863	High Similarity	NPC470997
0.8621	High Similarity	NPC19747
0.8611	High Similarity	NPC276676
0.8611	High Similarity	NPC233763
0.8609	High Similarity	NPC193798
0.8609	High Similarity	NPC207978
0.8609	High Similarity	NPC82851
0.8609	High Similarity	NPC470939
0.8609	High Similarity	NPC263432
0.8609	High Similarity	NPC472771
0.8609	High Similarity	NPC69028
0.8609	High Similarity	NPC5079
0.8603	High Similarity	NPC298190
0.8601	High Similarity	NPC86935
0.8601	High Similarity	NPC251865
0.86	High Similarity	NPC477403
0.86	High Similarity	NPC474611
0.86	High Similarity	NPC307383
0.86	High Similarity	NPC475967
0.86	High Similarity	NPC262872
0.8593	High Similarity	NPC198904
0.8592	High Similarity	NPC121158
0.8592	High Similarity	NPC473152
0.8562	High Similarity	NPC211625
0.8562	High Similarity	NPC470790
0.8562	High Similarity	NPC470791
0.8562	High Similarity	NPC329180
0.8561	High Similarity	NPC46896
0.8553	High Similarity	NPC292389
0.8553	High Similarity	NPC472773
0.8553	High Similarity	NPC51568
0.8553	High Similarity	NPC469338
0.8553	High Similarity	NPC476197
0.8553	High Similarity	NPC477405
0.8553	High Similarity	NPC234660
0.8553	High Similarity	NPC419
0.8551	High Similarity	NPC471998
0.855	High Similarity	NPC1848
0.8543	High Similarity	NPC472653
0.8543	High Similarity	NPC335761
0.8543	High Similarity	NPC477402
0.8542	High Similarity	NPC41182
0.8533	High Similarity	NPC261597
0.8533	High Similarity	NPC45101
0.8531	High Similarity	NPC476946
0.8519	High Similarity	NPC207294
0.8519	High Similarity	NPC327527
0.8519	High Similarity	NPC476917
0.8519	High Similarity	NPC112706
0.8514	High Similarity	NPC33938
0.8511	High Similarity	NPC90953
0.8503	High Similarity	NPC476936
0.85	High Similarity	NPC307401
0.85	High Similarity	NPC310043
0.8497	Intermediate Similarity	NPC123088
0.8497	Intermediate Similarity	NPC476860
0.8497	Intermediate Similarity	NPC476858
0.8497	Intermediate Similarity	NPC469849
0.8497	Intermediate Similarity	NPC476856
0.8497	Intermediate Similarity	NPC276551
0.8497	Intermediate Similarity	NPC476857
0.8497	Intermediate Similarity	NPC470940
0.8489	Intermediate Similarity	NPC158525
0.8487	Intermediate Similarity	NPC329938
0.8487	Intermediate Similarity	NPC200782
0.8485	Intermediate Similarity	NPC36255
0.8478	Intermediate Similarity	NPC471006
0.8472	Intermediate Similarity	NPC84479
0.8467	Intermediate Similarity	NPC89133
0.8467	Intermediate Similarity	NPC469485
0.8467	Intermediate Similarity	NPC204663
0.8444	Intermediate Similarity	NPC83178
0.8442	Intermediate Similarity	NPC23387
0.8442	Intermediate Similarity	NPC470875
0.8435	Intermediate Similarity	NPC471001
0.8435	Intermediate Similarity	NPC234494
0.8433	Intermediate Similarity	NPC230979
0.8431	Intermediate Similarity	NPC469846
0.8431	Intermediate Similarity	NPC224394
0.8431	Intermediate Similarity	NPC165218
0.8431	Intermediate Similarity	NPC134254
0.8431	Intermediate Similarity	NPC302369
0.8431	Intermediate Similarity	NPC39986
0.8431	Intermediate Similarity	NPC663
0.8429	Intermediate Similarity	NPC214572
0.8425	Intermediate Similarity	NPC471174
0.8425	Intermediate Similarity	NPC255414
0.8425	Intermediate Similarity	NPC216755
0.8425	Intermediate Similarity	NPC71821
0.8421	Intermediate Similarity	NPC191828
0.8411	Intermediate Similarity	NPC36655
0.8411	Intermediate Similarity	NPC173544
0.8411	Intermediate Similarity	NPC187149
0.8411	Intermediate Similarity	NPC195131
0.8403	Intermediate Similarity	NPC205071
0.8403	Intermediate Similarity	NPC243577
0.8394	Intermediate Similarity	NPC476925
0.8389	Intermediate Similarity	NPC476939
0.8389	Intermediate Similarity	NPC476940
0.8387	Intermediate Similarity	NPC472282
0.8387	Intermediate Similarity	NPC473753
0.8387	Intermediate Similarity	NPC473766
0.8387	Intermediate Similarity	NPC476853
0.8387	Intermediate Similarity	NPC173516
0.8387	Intermediate Similarity	NPC476861
0.8387	Intermediate Similarity	NPC472774
0.8387	Intermediate Similarity	NPC476850
0.8387	Intermediate Similarity	NPC472775
0.8382	Intermediate Similarity	NPC477040
0.838	Intermediate Similarity	NPC202260
0.8378	Intermediate Similarity	NPC212257
0.8377	Intermediate Similarity	NPC470182
0.8366	Intermediate Similarity	NPC188649
0.8366	Intermediate Similarity	NPC197596
0.8366	Intermediate Similarity	NPC117986
0.8366	Intermediate Similarity	NPC18347
0.8366	Intermediate Similarity	NPC149896

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 NPC476943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	947
0.2-0.3	1819
0.3-0.4	2730
0.4-0.5	2065
0.5-0.6	987
0.6-0.7	270
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
0.8278	Intermediate Similarity	NPD5761	Phase 2
0.8278	Intermediate Similarity	NPD5760	Phase 2
0.7834	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD920	Approved
0.7619	Intermediate Similarity	NPD8434	Phase 2
0.7517	Intermediate Similarity	NPD2346	Discontinued
0.7517	Intermediate Similarity	NPD1471	Phase 3
0.7516	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD6832	Phase 2
0.7386	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD2799	Discontinued
0.7368	Intermediate Similarity	NPD4628	Phase 3
0.7358	Intermediate Similarity	NPD7819	Suspended
0.7355	Intermediate Similarity	NPD6273	Approved
0.7346	Intermediate Similarity	NPD5494	Approved
0.7333	Intermediate Similarity	NPD2796	Approved
0.7329	Intermediate Similarity	NPD2313	Discontinued
0.7321	Intermediate Similarity	NPD6764	Approved
0.7321	Intermediate Similarity	NPD6765	Approved
0.7305	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD6599	Discontinued
0.7254	Intermediate Similarity	NPD3972	Approved
0.725	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD3749	Approved
0.7222	Intermediate Similarity	NPD3266	Approved
0.7222	Intermediate Similarity	NPD3267	Approved
0.7215	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1243	Approved
0.7181	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD2344	Approved
0.7163	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD8032	Phase 2
0.7152	Intermediate Similarity	NPD6808	Phase 2
0.7151	Intermediate Similarity	NPD6784	Approved
0.7151	Intermediate Similarity	NPD6785	Approved
0.7125	Intermediate Similarity	NPD7411	Suspended
0.7118	Intermediate Similarity	NPD6559	Discontinued
0.7117	Intermediate Similarity	NPD7075	Discontinued
0.7114	Intermediate Similarity	NPD4307	Phase 2
0.7107	Intermediate Similarity	NPD3226	Approved
0.7095	Intermediate Similarity	NPD3268	Approved
0.7083	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7078	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD919	Approved
0.7067	Intermediate Similarity	NPD1933	Approved
0.7055	Intermediate Similarity	NPD1019	Discontinued
0.7055	Intermediate Similarity	NPD2798	Approved
0.7039	Intermediate Similarity	NPD3748	Approved
0.7013	Intermediate Similarity	NPD1549	Phase 2
0.7006	Intermediate Similarity	NPD6799	Approved
0.7	Intermediate Similarity	NPD7458	Discontinued
0.6994	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD1551	Phase 2
0.6993	Remote Similarity	NPD2935	Discontinued
0.6987	Remote Similarity	NPD2309	Approved
0.6986	Remote Similarity	NPD2797	Approved
0.6975	Remote Similarity	NPD6801	Discontinued
0.6972	Remote Similarity	NPD5585	Approved
0.6962	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD2534	Approved
0.6962	Remote Similarity	NPD2532	Approved
0.6962	Remote Similarity	NPD2533	Approved
0.6948	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD4308	Phase 3
0.6923	Remote Similarity	NPD17	Approved
0.6923	Remote Similarity	NPD7003	Approved
0.6923	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1876	Approved
0.6914	Remote Similarity	NPD5889	Approved
0.6914	Remote Similarity	NPD5890	Approved
0.6897	Remote Similarity	NPD9717	Approved
0.6887	Remote Similarity	NPD2979	Phase 3
0.6886	Remote Similarity	NPD1247	Approved
0.6879	Remote Similarity	NPD3887	Approved
0.6871	Remote Similarity	NPD6280	Approved
0.6871	Remote Similarity	NPD1203	Approved
0.6871	Remote Similarity	NPD6279	Approved
0.6864	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD2800	Approved
0.6852	Remote Similarity	NPD4380	Phase 2
0.6842	Remote Similarity	NPD4618	Approved
0.6842	Remote Similarity	NPD4622	Approved
0.6842	Remote Similarity	NPD5844	Phase 1
0.6835	Remote Similarity	NPD7236	Approved
0.6818	Remote Similarity	NPD7033	Discontinued
0.6815	Remote Similarity	NPD3750	Approved
0.6807	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD3817	Phase 2
0.6788	Remote Similarity	NPD5402	Approved
0.6786	Remote Similarity	NPD1241	Discontinued
0.6786	Remote Similarity	NPD6959	Discontinued
0.6781	Remote Similarity	NPD1608	Approved
0.6776	Remote Similarity	NPD4140	Approved
0.6774	Remote Similarity	NPD6100	Approved
0.6774	Remote Similarity	NPD2438	Suspended
0.6774	Remote Similarity	NPD6099	Approved
0.677	Remote Similarity	NPD5403	Approved
0.677	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1934	Approved
0.6757	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD5688	Approved
0.6753	Remote Similarity	NPD5689	Approved
0.675	Remote Similarity	NPD5401	Approved
0.6748	Remote Similarity	NPD6585	Discontinued
0.6747	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD7768	Phase 2
0.6743	Remote Similarity	NPD8312	Approved
0.6743	Remote Similarity	NPD8313	Approved
0.6735	Remote Similarity	NPD4359	Approved
0.6732	Remote Similarity	NPD447	Suspended
0.6732	Remote Similarity	NPD6355	Discontinued
0.6725	Remote Similarity	NPD7473	Discontinued
0.6712	Remote Similarity	NPD1281	Approved
0.6711	Remote Similarity	NPD5647	Approved
0.671	Remote Similarity	NPD1510	Phase 2
0.6709	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD4110	Phase 3
0.6706	Remote Similarity	NPD3926	Phase 2
0.6688	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD3818	Discontinued
0.6686	Remote Similarity	NPD8127	Discontinued
0.6667	Remote Similarity	NPD3140	Approved
0.6667	Remote Similarity	NPD3142	Approved
0.6667	Remote Similarity	NPD2182	Approved
0.6647	Remote Similarity	NPD3882	Suspended
0.6647	Remote Similarity	NPD6232	Discontinued
0.6646	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD411	Approved
0.6645	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD3764	Approved
0.6643	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD7239	Suspended
0.6624	Remote Similarity	NPD2353	Approved
0.6624	Remote Similarity	NPD6002	Phase 3
0.6624	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6005	Phase 3
0.6624	Remote Similarity	NPD6004	Phase 3
0.6622	Remote Similarity	NPD5327	Phase 3
0.6604	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD4870	Approved
0.6601	Remote Similarity	NPD6233	Phase 2
0.6598	Remote Similarity	NPD8404	Phase 2
0.6582	Remote Similarity	NPD2897	Discontinued
0.6581	Remote Similarity	NPD1607	Approved
0.6577	Remote Similarity	NPD1283	Approved
0.6575	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD6844	Discontinued
0.6561	Remote Similarity	NPD2531	Phase 2
0.6558	Remote Similarity	NPD1240	Approved
0.6552	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.655	Remote Similarity	NPD5710	Approved
0.655	Remote Similarity	NPD7229	Phase 3
0.655	Remote Similarity	NPD5711	Approved
0.6538	Remote Similarity	NPD7097	Phase 1
0.6536	Remote Similarity	NPD6798	Discontinued
0.6536	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6527	Remote Similarity	NPD2801	Approved
0.6507	Remote Similarity	NPD5691	Approved
0.6507	Remote Similarity	NPD1651	Approved
0.6505	Remote Similarity	NPD4107	Approved
0.65	Remote Similarity	NPD8166	Discontinued
0.649	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD2296	Approved
0.6486	Remote Similarity	NPD6287	Discontinued
0.6479	Remote Similarity	NPD5535	Approved
0.6478	Remote Similarity	NPD2424	Discontinued
0.6477	Remote Similarity	NPD5953	Discontinued
0.6474	Remote Similarity	NPD6166	Phase 2
0.6474	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6474	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD7008	Discontinued
0.6467	Remote Similarity	NPD37	Approved
0.6463	Remote Similarity	NPD1778	Approved
0.6463	Remote Similarity	NPD3869	Phase 3
0.6463	Remote Similarity	NPD3873	Phase 3
0.646	Remote Similarity	NPD2354	Approved
0.6457	Remote Similarity	NPD7286	Phase 2
0.6456	Remote Similarity	NPD4477	Approved
0.6456	Remote Similarity	NPD4476	Approved
0.6452	Remote Similarity	NPD8285	Discontinued
0.645	Remote Similarity	NPD4967	Phase 2
0.645	Remote Similarity	NPD4965	Approved
0.645	Remote Similarity	NPD4966	Approved
0.6444	Remote Similarity	NPD8150	Discontinued
0.6424	Remote Similarity	NPD6362	Approved
0.642	Remote Similarity	NPD7440	Discontinued
0.642	Remote Similarity	NPD7074	Phase 3
0.6419	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6419	Remote Similarity	NPD3496	Discontinued
0.6414	Remote Similarity	NPD9493	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