NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	372.16
Volume:	368.549
LogP:	1.901
LogD:	1.85
LogS:	-4.466
# Rotatable Bonds:	3
TPSA:	78.13
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.634
Synthetic Accessibility Score:	6.281
Fsp3:	0.571
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.808
MDCK Permeability:	2.421485260128975e-05
Pgp-inhibitor:	0.244
Pgp-substrate:	0.103
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.811
Plasma Protein Binding (PPB):	88.32575225830078%
Volume Distribution (VD):	2.677
Pgp-substrate:	6.242248058319092%

ADMET: Metabolism

CYP1A2-inhibitor:	0.018
CYP1A2-substrate:	0.87
CYP2C19-inhibitor:	0.164
CYP2C19-substrate:	0.616
CYP2C9-inhibitor:	0.487
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.023
CYP2D6-substrate:	0.515
CYP3A4-inhibitor:	0.788
CYP3A4-substrate:	0.279

ADMET: Excretion

Clearance (CL):	3.572
Half-life (T1/2):	0.806

ADMET: Toxicity

hERG Blockers:	0.113
Human Hepatotoxicity (H-HT):	0.407
Drug-inuced Liver Injury (DILI):	0.15
AMES Toxicity:	0.975
Rat Oral Acute Toxicity:	0.999
Maximum Recommended Daily Dose:	0.983
Skin Sensitization:	0.737
Carcinogencity:	0.927
Eye Corrosion:	0.003
Eye Irritation:	0.207
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC476937

Natural Product ID:	NPC476937
*Common Name:**	methyl (1R,2S,4S,6R,8R,9R)-6-(furan-3-yl)-2-hydroxy-16-methylidene-3,5-dioxatetracyclo[6.5.3.01,9.04,8]hexadec-12-ene-13-carboxylate
IUPAC Name:	methyl (1R,2S,4S,6R,8R,9R)-6-(furan-3-yl)-2-hydroxy-16-methylidene-3,5-dioxatetracyclo[6.5.3.01,9.04,8]hexadec-12-ene-13-carboxylate
Synonyms:
Standard InCHIKey:	BQEWXAMCMSCDQX-HDHGSYJOSA-N
Standard InCHI:	InChI=1S/C21H24O6/c1-12-6-8-20-14(17(22)24-2)4-3-5-16(20)21(12)10-15(13-7-9-25-11-13)26-19(21)27-18(20)23/h4,7,9,11,15-16,18-19,23H,1,3,5-6,8,10H2,2H3/t15-,16-,18+,19+,20+,21+/m1/s1
SMILES:	COC(=O)C1=CCC[C@@H]2[C@]13CCC(=C)[C@@]24C[C@@H](O[C@H]4O[C@@H]3O)C5=COC=C5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90676779
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane 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
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 NPC476937 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	309
0.1-0.2	1183
0.2-0.3	2744
0.3-0.4	5188
0.4-0.5	10580
0.5-0.6	11583
0.6-0.7	9689
0.7-0.8	1130
0.8-0.85	208
0.85-0.9	66
0.9-0.95	11
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476938
0.9929	High Similarity	NPC476942
0.9929	High Similarity	NPC476941
0.9653	High Similarity	NPC476940
0.9653	High Similarity	NPC476939
0.9306	High Similarity	NPC250228
0.9241	High Similarity	NPC7388
0.9172	High Similarity	NPC10088
0.9116	High Similarity	NPC476936
0.9103	High Similarity	NPC276676
0.9073	High Similarity	NPC262872
0.9014	High Similarity	NPC90953
0.8993	High Similarity	NPC147168
0.8973	High Similarity	NPC346
0.8968	High Similarity	NPC100333
0.8954	High Similarity	NPC211777
0.8933	High Similarity	NPC57998
0.8896	High Similarity	NPC198047
0.8873	High Similarity	NPC310830
0.8873	High Similarity	NPC186626
0.8865	High Similarity	NPC92941
0.8836	High Similarity	NPC476944
0.8831	High Similarity	NPC207978
0.8797	High Similarity	NPC160818
0.8797	High Similarity	NPC169299
0.8792	High Similarity	NPC195325
0.8767	High Similarity	NPC267632
0.8767	High Similarity	NPC223415
0.875	High Similarity	NPC44675
0.875	High Similarity	NPC214541
0.875	High Similarity	NPC35000
0.8742	High Similarity	NPC469503
0.8741	High Similarity	NPC470742
0.8734	High Similarity	NPC82602
0.8718	High Similarity	NPC146991
0.8684	High Similarity	NPC30222
0.8684	High Similarity	NPC178932
0.8681	High Similarity	NPC476943
0.8681	High Similarity	NPC220094
0.8662	High Similarity	NPC93172
0.8662	High Similarity	NPC97574
0.8639	High Similarity	NPC470741
0.8636	High Similarity	NPC472777
0.8636	High Similarity	NPC261597
0.8636	High Similarity	NPC472776
0.8636	High Similarity	NPC472778
0.863	High Similarity	NPC20500
0.8627	High Similarity	NPC469336
0.8618	High Similarity	NPC75906
0.8582	High Similarity	NPC89133
0.8581	High Similarity	NPC307383
0.8581	High Similarity	NPC475967
0.8561	High Similarity	NPC319140
0.8561	High Similarity	NPC95567
0.8543	High Similarity	NPC472654
0.8542	High Similarity	NPC146872
0.8535	High Similarity	NPC419
0.8516	High Similarity	NPC187149
0.8516	High Similarity	NPC36655
0.8516	High Similarity	NPC299038
0.8506	High Similarity	NPC264943
0.8497	Intermediate Similarity	NPC44577
0.8456	Intermediate Similarity	NPC137295
0.8456	Intermediate Similarity	NPC251865
0.8456	Intermediate Similarity	NPC142113
0.8442	Intermediate Similarity	NPC282445
0.8428	Intermediate Similarity	NPC214600
0.8411	Intermediate Similarity	NPC470941
0.8411	Intermediate Similarity	NPC221809
0.8408	Intermediate Similarity	NPC477402
0.8405	Intermediate Similarity	NPC262386
0.8403	Intermediate Similarity	NPC471998
0.8397	Intermediate Similarity	NPC472772
0.8397	Intermediate Similarity	NPC45101
0.8387	Intermediate Similarity	NPC281258
0.838	Intermediate Similarity	NPC21460
0.8378	Intermediate Similarity	NPC205765
0.8369	Intermediate Similarity	NPC112706
0.8369	Intermediate Similarity	NPC207294
0.8366	Intermediate Similarity	NPC159927
0.8366	Intermediate Similarity	NPC469335
0.8365	Intermediate Similarity	NPC470182
0.8365	Intermediate Similarity	NPC123088
0.8357	Intermediate Similarity	NPC138139
0.8357	Intermediate Similarity	NPC46536
0.8354	Intermediate Similarity	NPC69028
0.8354	Intermediate Similarity	NPC5079
0.8344	Intermediate Similarity	NPC477403
0.8322	Intermediate Similarity	NPC61788
0.8322	Intermediate Similarity	NPC298190
0.8313	Intermediate Similarity	NPC472141
0.8302	Intermediate Similarity	NPC165218
0.8302	Intermediate Similarity	NPC51568
0.8302	Intermediate Similarity	NPC472139
0.8302	Intermediate Similarity	NPC234660
0.8299	Intermediate Similarity	NPC236532
0.8298	Intermediate Similarity	NPC83178
0.8291	Intermediate Similarity	NPC335761
0.8289	Intermediate Similarity	NPC471174
0.828	Intermediate Similarity	NPC249021
0.8278	Intermediate Similarity	NPC41182
0.8267	Intermediate Similarity	NPC476946
0.8261	Intermediate Similarity	NPC472651
0.8261	Intermediate Similarity	NPC476850
0.8261	Intermediate Similarity	NPC476861
0.825	Intermediate Similarity	NPC472664
0.825	Intermediate Similarity	NPC276551
0.8247	Intermediate Similarity	NPC470997
0.8247	Intermediate Similarity	NPC196864
0.8247	Intermediate Similarity	NPC476122
0.8247	Intermediate Similarity	NPC477404
0.8239	Intermediate Similarity	NPC149896
0.8239	Intermediate Similarity	NPC472771
0.8239	Intermediate Similarity	NPC200782
0.8239	Intermediate Similarity	NPC472767
0.8231	Intermediate Similarity	NPC42400
0.8228	Intermediate Similarity	NPC475226
0.8228	Intermediate Similarity	NPC474611
0.8227	Intermediate Similarity	NPC74612
0.8227	Intermediate Similarity	NPC23086
0.8224	Intermediate Similarity	NPC262198
0.8219	Intermediate Similarity	NPC158525
0.8217	Intermediate Similarity	NPC469485
0.8212	Intermediate Similarity	NPC86935
0.821	Intermediate Similarity	NPC271235
0.821	Intermediate Similarity	NPC472652
0.8205	Intermediate Similarity	NPC237259
0.8205	Intermediate Similarity	NPC34421
0.8205	Intermediate Similarity	NPC98206
0.82	Intermediate Similarity	NPC121158
0.82	Intermediate Similarity	NPC473152
0.8199	Intermediate Similarity	NPC307781
0.8199	Intermediate Similarity	NPC478178
0.8199	Intermediate Similarity	NPC470875
0.8199	Intermediate Similarity	NPC472670
0.8194	Intermediate Similarity	NPC18135
0.8187	Intermediate Similarity	NPC39986
0.8187	Intermediate Similarity	NPC663
0.8187	Intermediate Similarity	NPC292389
0.8187	Intermediate Similarity	NPC472773
0.8187	Intermediate Similarity	NPC302369
0.8187	Intermediate Similarity	NPC224394
0.8187	Intermediate Similarity	NPC477405
0.8187	Intermediate Similarity	NPC469338
0.8187	Intermediate Similarity	NPC134254
0.8182	Intermediate Similarity	NPC223063
0.8182	Intermediate Similarity	NPC329180
0.8182	Intermediate Similarity	NPC120836
0.8176	Intermediate Similarity	NPC472376
0.8176	Intermediate Similarity	NPC25255
0.8176	Intermediate Similarity	NPC472653
0.817	Intermediate Similarity	NPC216755
0.8165	Intermediate Similarity	NPC304692
0.8165	Intermediate Similarity	NPC173544
0.816	Intermediate Similarity	NPC472660
0.8156	Intermediate Similarity	NPC179354
0.8153	Intermediate Similarity	NPC296807
0.8153	Intermediate Similarity	NPC469850
0.8153	Intermediate Similarity	NPC155939
0.8153	Intermediate Similarity	NPC92979
0.8153	Intermediate Similarity	NPC141538
0.8144	Intermediate Similarity	NPC470938
0.8143	Intermediate Similarity	NPC16922
0.8141	Intermediate Similarity	NPC472672
0.8141	Intermediate Similarity	NPC476201
0.8141	Intermediate Similarity	NPC33938
0.8141	Intermediate Similarity	NPC268905
0.8138	Intermediate Similarity	NPC471995
0.8137	Intermediate Similarity	NPC476857
0.8137	Intermediate Similarity	NPC469849
0.8137	Intermediate Similarity	NPC470940
0.8137	Intermediate Similarity	NPC476858
0.8137	Intermediate Similarity	NPC271657
0.8137	Intermediate Similarity	NPC476856
0.8129	Intermediate Similarity	NPC46551
0.8125	Intermediate Similarity	NPC263432
0.8125	Intermediate Similarity	NPC18347
0.8125	Intermediate Similarity	NPC82851
0.8125	Intermediate Similarity	NPC193798
0.8125	Intermediate Similarity	NPC117986
0.811	Intermediate Similarity	NPC159232
0.8101	Intermediate Similarity	NPC60973
0.8101	Intermediate Similarity	NPC209364
0.8101	Intermediate Similarity	NPC104736
0.8098	Intermediate Similarity	NPC472673
0.8098	Intermediate Similarity	NPC471397
0.8089	Intermediate Similarity	NPC253201
0.8089	Intermediate Similarity	NPC302054
0.8086	Intermediate Similarity	NPC23387
0.8082	Intermediate Similarity	NPC470740
0.8082	Intermediate Similarity	NPC218838
0.8077	Intermediate Similarity	NPC471000
0.8077	Intermediate Similarity	NPC272590
0.8071	Intermediate Similarity	NPC477967
0.8067	Intermediate Similarity	NPC67003
0.8065	Intermediate Similarity	NPC69647
0.8065	Intermediate Similarity	NPC125182
0.8065	Intermediate Similarity	NPC234494
0.8065	Intermediate Similarity	NPC211625
0.8063	Intermediate Similarity	NPC305016

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 NPC476937 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	257
0.1-0.2	840
0.2-0.3	1947
0.3-0.4	2674
0.4-0.5	2168
0.5-0.6	985
0.6-0.7	262
0.7-0.8	15
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
0.8153	Intermediate Similarity	NPD5760	Phase 2
0.8153	Intermediate Similarity	NPD5761	Phase 2
0.7544	Intermediate Similarity	NPD6559	Discontinued
0.7429	Intermediate Similarity	NPD8434	Phase 2
0.7419	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD6764	Approved
0.7241	Intermediate Similarity	NPD6765	Approved
0.717	Intermediate Similarity	NPD4628	Phase 3
0.716	Intermediate Similarity	NPD6273	Approved
0.7159	Intermediate Similarity	NPD8313	Approved
0.7159	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD920	Approved
0.7089	Intermediate Similarity	NPD2346	Discontinued
0.7083	Intermediate Similarity	NPD4967	Phase 2
0.7083	Intermediate Similarity	NPD4965	Approved
0.7083	Intermediate Similarity	NPD4966	Approved
0.7079	Intermediate Similarity	NPD6784	Approved
0.7079	Intermediate Similarity	NPD6785	Approved
0.707	Intermediate Similarity	NPD2799	Discontinued
0.7066	Intermediate Similarity	NPD7819	Suspended
0.7063	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD1049	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD2313	Discontinued
0.7011	Intermediate Similarity	NPD3818	Discontinued
0.6994	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6002	Phase 3
0.6981	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6004	Phase 3
0.6981	Remote Similarity	NPD6005	Phase 3
0.6964	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD3749	Approved
0.6918	Remote Similarity	NPD1551	Phase 2
0.6914	Remote Similarity	NPD7228	Approved
0.6905	Remote Similarity	NPD37	Approved
0.6901	Remote Similarity	NPD6234	Discontinued
0.6883	Remote Similarity	NPD6832	Phase 2
0.6879	Remote Similarity	NPD1933	Approved
0.6875	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6864	Remote Similarity	NPD8455	Phase 2
0.6863	Remote Similarity	NPD2798	Approved
0.6852	Remote Similarity	NPD3750	Approved
0.6845	Remote Similarity	NPD7411	Suspended
0.6842	Remote Similarity	NPD7075	Discontinued
0.6839	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD7458	Discontinued
0.6826	Remote Similarity	NPD3226	Approved
0.6821	Remote Similarity	NPD9717	Approved
0.6813	Remote Similarity	NPD2935	Discontinued
0.6797	Remote Similarity	NPD2797	Approved
0.6793	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.679	Remote Similarity	NPD2800	Approved
0.679	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD2532	Approved
0.6788	Remote Similarity	NPD2534	Approved
0.6788	Remote Similarity	NPD2533	Approved
0.6786	Remote Similarity	NPD6599	Discontinued
0.6784	Remote Similarity	NPD7768	Phase 2
0.6763	Remote Similarity	NPD5494	Approved
0.676	Remote Similarity	NPD7240	Approved
0.6753	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.675	Remote Similarity	NPD7033	Discontinued
0.675	Remote Similarity	NPD3748	Approved
0.6742	Remote Similarity	NPD7074	Phase 3
0.6728	Remote Similarity	NPD1549	Phase 2
0.6727	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6725	Remote Similarity	NPD5402	Approved
0.6725	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7199	Phase 2
0.6723	Remote Similarity	NPD7799	Discontinued
0.6722	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD2796	Approved
0.6707	Remote Similarity	NPD5403	Approved
0.6706	Remote Similarity	NPD6801	Discontinued
0.6688	Remote Similarity	NPD3268	Approved
0.6688	Remote Similarity	NPD1203	Approved
0.6688	Remote Similarity	NPD3764	Approved
0.6687	Remote Similarity	NPD5401	Approved
0.6687	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD1243	Approved
0.6686	Remote Similarity	NPD4380	Phase 2
0.6685	Remote Similarity	NPD7054	Approved
0.6685	Remote Similarity	NPD5844	Phase 1
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD7685	Pre-registration
0.6667	Remote Similarity	NPD447	Suspended
0.6648	Remote Similarity	NPD7472	Approved
0.6646	Remote Similarity	NPD4308	Phase 3
0.6646	Remote Similarity	NPD7003	Approved
0.6645	Remote Similarity	NPD1019	Discontinued
0.6645	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD5647	Approved
0.6633	Remote Similarity	NPD8404	Phase 2
0.6629	Remote Similarity	NPD8127	Discontinued
0.6627	Remote Similarity	NPD6799	Approved
0.6626	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6797	Phase 2
0.661	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD919	Approved
0.6607	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6604	Remote Similarity	NPD4140	Approved
0.6601	Remote Similarity	NPD1608	Approved
0.659	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD7028	Phase 2
0.6584	Remote Similarity	NPD7097	Phase 1
0.6582	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD7251	Discontinued
0.6564	Remote Similarity	NPD1471	Phase 3
0.6562	Remote Similarity	NPD6355	Discontinued
0.6554	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD7808	Phase 3
0.6536	Remote Similarity	NPD1091	Approved
0.6536	Remote Similarity	NPD3751	Discontinued
0.652	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD1934	Approved
0.6507	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD2309	Approved
0.65	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4307	Phase 2
0.6478	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6478	Remote Similarity	NPD411	Approved
0.6474	Remote Similarity	NPD3266	Approved
0.6474	Remote Similarity	NPD6362	Approved
0.6474	Remote Similarity	NPD3267	Approved
0.6467	Remote Similarity	NPD7236	Approved
0.646	Remote Similarity	NPD5124	Phase 1
0.646	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6453	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD5585	Approved
0.6446	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD4110	Phase 3
0.6444	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD7435	Discontinued
0.6442	Remote Similarity	NPD1510	Phase 2
0.6441	Remote Similarity	NPD6959	Discontinued
0.6441	Remote Similarity	NPD1247	Approved
0.6438	Remote Similarity	NPD8032	Phase 2
0.6438	Remote Similarity	NPD6233	Phase 2
0.6437	Remote Similarity	NPD3817	Phase 2
0.6424	Remote Similarity	NPD2424	Discontinued
0.642	Remote Similarity	NPD6653	Approved
0.6417	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD6844	Discontinued
0.6405	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD1778	Approved
0.6405	Remote Similarity	NPD17	Approved
0.6404	Remote Similarity	NPD7229	Phase 3
0.6404	Remote Similarity	NPD6808	Phase 2
0.6404	Remote Similarity	NPD3787	Discontinued
0.6404	Remote Similarity	NPD6232	Discontinued
0.6404	Remote Similarity	NPD5710	Approved
0.6404	Remote Similarity	NPD5711	Approved
0.6402	Remote Similarity	NPD6099	Approved
0.6402	Remote Similarity	NPD6100	Approved
0.64	Remote Similarity	NPD3882	Suspended
0.6391	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD7473	Discontinued
0.6376	Remote Similarity	NPD1241	Discontinued
0.6375	Remote Similarity	NPD6798	Discontinued
0.6375	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD1653	Approved
0.6373	Remote Similarity	NPD6779	Approved
0.6373	Remote Similarity	NPD6778	Approved
0.6373	Remote Similarity	NPD6781	Approved
0.6373	Remote Similarity	NPD6780	Approved
0.6373	Remote Similarity	NPD6776	Approved
0.6373	Remote Similarity	NPD6782	Approved
0.6373	Remote Similarity	NPD6777	Approved
0.6358	Remote Similarity	NPD4622	Approved
0.6358	Remote Similarity	NPD9493	Approved
0.6358	Remote Similarity	NPD4618	Approved
0.6354	Remote Similarity	NPD4420	Approved
0.6343	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD6166	Phase 2
0.6333	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6319	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6313	Remote Similarity	NPD7315	Approved
0.631	Remote Similarity	NPD8150	Discontinued
0.6308	Remote Similarity	NPD6823	Phase 2
0.6306	Remote Similarity	NPD1283	Approved
0.6306	Remote Similarity	NPD3225	Approved
0.6306	Remote Similarity	NPD1876	Approved
0.6303	Remote Similarity	NPD4477	Approved
0.6303	Remote Similarity	NPD4476	Approved
0.63	Remote Similarity	NPD7783	Phase 2
0.63	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD2979	Phase 3

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