NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	430.16
Volume:	418.085
LogP:	1.898
LogD:	1.391
LogS:	-4.404
# Rotatable Bonds:	5
TPSA:	104.43
# H-Bond Aceptor:	8
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.577
Synthetic Accessibility Score:	6.401
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.885
MDCK Permeability:	5.1179489673813805e-05
Pgp-inhibitor:	0.628
Pgp-substrate:	0.093
Human Intestinal Absorption (HIA):	0.079
20% Bioavailability (F20%):	0.031
30% Bioavailability (F30%):	0.663

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.826
Plasma Protein Binding (PPB):	70.48580169677734%
Volume Distribution (VD):	2.556
Pgp-substrate:	23.571998596191406%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.283
CYP2C19-inhibitor:	0.035
CYP2C19-substrate:	0.268
CYP2C9-inhibitor:	0.082
CYP2C9-substrate:	0.033
CYP2D6-inhibitor:	0.052
CYP2D6-substrate:	0.285
CYP3A4-inhibitor:	0.68
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	2.674
Half-life (T1/2):	0.72

ADMET: Toxicity

hERG Blockers:	0.487
Human Hepatotoxicity (H-HT):	0.533
Drug-inuced Liver Injury (DILI):	0.338
AMES Toxicity:	0.987
Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	0.992
Skin Sensitization:	0.648
Carcinogencity:	0.934
Eye Corrosion:	0.003
Eye Irritation:	0.053
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC476940

Natural Product ID:	NPC476940
*Common Name:**	methyl (1R,2R,4S,6R,8R,9S,14S)-14-acetyloxy-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,2R,4S,6R,8R,9S,14S)-14-acetyloxy-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:	HTVMZRDDOHBSER-CDSWCQBOSA-N
Standard InCHI:	InChI=1S/C23H26O8/c1-12-9-18(29-13(2)24)23-15(19(25)27-3)5-4-6-17(23)22(12)10-16(14-7-8-28-11-14)30-21(22)31-20(23)26/h5,7-8,11,16-18,20-21,26H,1,4,6,9-10H2,2-3H3/t16-,17+,18+,20-,21+,22+,23+/m1/s1
SMILES:	CC(=O)O[C@H]1CC(=C)[C@]23C[C@@H](O[C@H]2O[C@H]([C@@]14[C@H]3CCC=C4C(=O)OC)O)C5=COC=C5
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90676778
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 NPC476940 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	322
0.1-0.2	1247
0.2-0.3	2826
0.3-0.4	5031
0.4-0.5	9836
0.5-0.6	11034
0.6-0.7	10177
0.7-0.8	1817
0.8-0.85	291
0.85-0.9	85
0.9-0.95	24
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476939
0.9653	High Similarity	NPC476938
0.9653	High Similarity	NPC476937
0.9586	High Similarity	NPC476941
0.9586	High Similarity	NPC476942
0.9324	High Similarity	NPC476936
0.932	High Similarity	NPC7388
0.929	High Similarity	NPC100333
0.9281	High Similarity	NPC211777
0.9221	High Similarity	NPC198047
0.92	High Similarity	NPC147168
0.9139	High Similarity	NPC57998
0.9122	High Similarity	NPC250228
0.9114	High Similarity	NPC160818
0.9114	High Similarity	NPC169299
0.9073	High Similarity	NPC469503
0.9051	High Similarity	NPC82602
0.9032	High Similarity	NPC207978
0.9026	High Similarity	NPC262872
0.9	High Similarity	NPC195325
0.8981	High Similarity	NPC97574
0.8981	High Similarity	NPC93172
0.8961	High Similarity	NPC472777
0.8961	High Similarity	NPC472778
0.8961	High Similarity	NPC472776
0.8954	High Similarity	NPC469336
0.8954	High Similarity	NPC44675
0.8954	High Similarity	NPC214541
0.8954	High Similarity	NPC35000
0.8926	High Similarity	NPC346
0.8903	High Similarity	NPC307383
0.8889	High Similarity	NPC178932
0.8889	High Similarity	NPC30222
0.8867	High Similarity	NPC10088
0.8854	High Similarity	NPC419
0.8851	High Similarity	NPC223415
0.8839	High Similarity	NPC36655
0.8839	High Similarity	NPC261597
0.8836	High Similarity	NPC90953
0.8828	High Similarity	NPC186626
0.88	High Similarity	NPC276676
0.8792	High Similarity	NPC476944
0.8782	High Similarity	NPC475967
0.8766	High Similarity	NPC282445
0.875	High Similarity	NPC472654
0.8742	High Similarity	NPC221809
0.8718	High Similarity	NPC187149
0.8718	High Similarity	NPC472772
0.8718	High Similarity	NPC299038
0.8712	High Similarity	NPC262386
0.871	High Similarity	NPC264943
0.8701	High Similarity	NPC75906
0.8699	High Similarity	NPC470742
0.8693	High Similarity	NPC159927
0.8693	High Similarity	NPC469335
0.8679	High Similarity	NPC146991
0.8679	High Similarity	NPC470182
0.8671	High Similarity	NPC69028
0.8667	High Similarity	NPC251865
0.8625	High Similarity	NPC472141
0.8625	High Similarity	NPC214600
0.8618	High Similarity	NPC470941
0.8616	High Similarity	NPC472139
0.8616	High Similarity	NPC165218
0.8608	High Similarity	NPC477402
0.86	High Similarity	NPC470741
0.8599	High Similarity	NPC249021
0.8599	High Similarity	NPC45101
0.8591	High Similarity	NPC20500
0.8571	High Similarity	NPC476850
0.8571	High Similarity	NPC476861
0.8571	High Similarity	NPC476122
0.8571	High Similarity	NPC472651
0.8571	High Similarity	NPC310830
0.8562	High Similarity	NPC123088
0.8562	High Similarity	NPC92941
0.8562	High Similarity	NPC276551
0.8553	High Similarity	NPC5079
0.8553	High Similarity	NPC472771
0.8553	High Similarity	NPC200782
0.8553	High Similarity	NPC472767
0.8544	High Similarity	NPC477403
0.8544	High Similarity	NPC475226
0.8519	High Similarity	NPC472652
0.8519	High Similarity	NPC271235
0.8516	High Similarity	NPC18135
0.8509	High Similarity	NPC307781
0.8509	High Similarity	NPC472670
0.8509	High Similarity	NPC478178
0.8509	High Similarity	NPC470875
0.85	High Similarity	NPC51568
0.85	High Similarity	NPC302369
0.85	High Similarity	NPC292389
0.85	High Similarity	NPC39986
0.85	High Similarity	NPC477405
0.85	High Similarity	NPC234660
0.85	High Similarity	NPC469338
0.85	High Similarity	NPC472773
0.85	High Similarity	NPC134254
0.8497	Intermediate Similarity	NPC471174
0.8491	Intermediate Similarity	NPC335761
0.8491	Intermediate Similarity	NPC472653
0.8487	Intermediate Similarity	NPC41182
0.8477	Intermediate Similarity	NPC267632
0.8471	Intermediate Similarity	NPC469850
0.8462	Intermediate Similarity	NPC476201
0.8462	Intermediate Similarity	NPC472672
0.8452	Intermediate Similarity	NPC196864
0.8452	Intermediate Similarity	NPC477404
0.8447	Intermediate Similarity	NPC469849
0.8447	Intermediate Similarity	NPC476856
0.8447	Intermediate Similarity	NPC470940
0.8447	Intermediate Similarity	NPC271657
0.8447	Intermediate Similarity	NPC476857
0.8447	Intermediate Similarity	NPC476858
0.8447	Intermediate Similarity	NPC472664
0.8443	Intermediate Similarity	NPC470938
0.8438	Intermediate Similarity	NPC82851
0.8438	Intermediate Similarity	NPC117986
0.8438	Intermediate Similarity	NPC149896
0.8428	Intermediate Similarity	NPC474611
0.8421	Intermediate Similarity	NPC137295
0.8414	Intermediate Similarity	NPC61788
0.8411	Intermediate Similarity	NPC121158
0.8408	Intermediate Similarity	NPC237259
0.8408	Intermediate Similarity	NPC302054
0.8408	Intermediate Similarity	NPC98206
0.8408	Intermediate Similarity	NPC253201
0.8408	Intermediate Similarity	NPC34421
0.8405	Intermediate Similarity	NPC472673
0.8405	Intermediate Similarity	NPC471397
0.8395	Intermediate Similarity	NPC23387
0.8389	Intermediate Similarity	NPC220094
0.8389	Intermediate Similarity	NPC476943
0.8385	Intermediate Similarity	NPC663
0.8385	Intermediate Similarity	NPC224394
0.8377	Intermediate Similarity	NPC216755
0.8375	Intermediate Similarity	NPC25255
0.8365	Intermediate Similarity	NPC304692
0.8365	Intermediate Similarity	NPC286722
0.8365	Intermediate Similarity	NPC472283
0.8365	Intermediate Similarity	NPC470118
0.8365	Intermediate Similarity	NPC197137
0.8355	Intermediate Similarity	NPC476946
0.8354	Intermediate Similarity	NPC476262
0.8354	Intermediate Similarity	NPC141538
0.8354	Intermediate Similarity	NPC296807
0.8354	Intermediate Similarity	NPC92979
0.8354	Intermediate Similarity	NPC472660
0.8354	Intermediate Similarity	NPC155939
0.8344	Intermediate Similarity	NPC472775
0.8344	Intermediate Similarity	NPC472282
0.8344	Intermediate Similarity	NPC472764
0.8344	Intermediate Similarity	NPC173516
0.8344	Intermediate Similarity	NPC476853
0.8344	Intermediate Similarity	NPC478179
0.8344	Intermediate Similarity	NPC268905
0.8344	Intermediate Similarity	NPC472774
0.8344	Intermediate Similarity	NPC44577
0.8333	Intermediate Similarity	NPC476860
0.8333	Intermediate Similarity	NPC470997
0.8333	Intermediate Similarity	NPC156189
0.8323	Intermediate Similarity	NPC193798
0.8323	Intermediate Similarity	NPC470792
0.8323	Intermediate Similarity	NPC290400
0.8323	Intermediate Similarity	NPC18347
0.8323	Intermediate Similarity	NPC96443
0.8323	Intermediate Similarity	NPC329938
0.8323	Intermediate Similarity	NPC263432
0.8313	Intermediate Similarity	NPC475295
0.8313	Intermediate Similarity	NPC473473
0.8312	Intermediate Similarity	NPC262198
0.8303	Intermediate Similarity	NPC159232
0.8302	Intermediate Similarity	NPC204663
0.8302	Intermediate Similarity	NPC469485
0.8302	Intermediate Similarity	NPC126723
0.8302	Intermediate Similarity	NPC209364
0.8302	Intermediate Similarity	NPC104736
0.8293	Intermediate Similarity	NPC472766
0.8293	Intermediate Similarity	NPC472765
0.8288	Intermediate Similarity	NPC298190
0.8288	Intermediate Similarity	NPC89133
0.8282	Intermediate Similarity	NPC149945
0.828	Intermediate Similarity	NPC471000
0.8278	Intermediate Similarity	NPC67003
0.8272	Intermediate Similarity	NPC469846
0.8269	Intermediate Similarity	NPC470790
0.8269	Intermediate Similarity	NPC470791
0.8269	Intermediate Similarity	NPC125182
0.8269	Intermediate Similarity	NPC69647
0.8269	Intermediate Similarity	NPC211625
0.8267	Intermediate Similarity	NPC236532
0.8264	Intermediate Similarity	NPC319140
0.8264	Intermediate Similarity	NPC95567
0.8261	Intermediate Similarity	NPC470789
0.8261	Intermediate Similarity	NPC305016
0.8258	Intermediate Similarity	NPC255414
0.8255	Intermediate Similarity	NPC146872
0.825	Intermediate Similarity	NPC195131
0.825	Intermediate Similarity	NPC470119

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 NPC476940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	863
0.2-0.3	2013
0.3-0.4	2647
0.4-0.5	2050
0.5-0.6	990
0.6-0.7	282
0.7-0.8	26
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8354	Intermediate Similarity	NPD5760	Phase 2
0.8354	Intermediate Similarity	NPD5761	Phase 2
0.7836	Intermediate Similarity	NPD6559	Discontinued
0.7714	Intermediate Similarity	NPD8434	Phase 2
0.7711	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7365	Intermediate Similarity	NPD7819	Suspended
0.7345	Intermediate Similarity	NPD8313	Approved
0.7345	Intermediate Similarity	NPD8312	Approved
0.7337	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6765	Approved
0.733	Intermediate Similarity	NPD6764	Approved
0.7299	Intermediate Similarity	NPD3818	Discontinued
0.7296	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD920	Approved
0.7202	Intermediate Similarity	NPD37	Approved
0.72	Intermediate Similarity	NPD7228	Approved
0.7193	Intermediate Similarity	NPD6234	Discontinued
0.7167	Intermediate Similarity	NPD6785	Approved
0.7167	Intermediate Similarity	NPD6784	Approved
0.716	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4628	Phase 3
0.7152	Intermediate Similarity	NPD6273	Approved
0.7091	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD2346	Discontinued
0.7065	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD2799	Discontinued
0.7062	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD8455	Phase 2
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD7411	Suspended
0.7039	Intermediate Similarity	NPD7240	Approved
0.7035	Intermediate Similarity	NPD3749	Approved
0.7035	Intermediate Similarity	NPD7075	Discontinued
0.7024	Intermediate Similarity	NPD3226	Approved
0.7024	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7074	Phase 3
0.7011	Intermediate Similarity	NPD7199	Phase 2
0.7006	Intermediate Similarity	NPD7799	Discontinued
0.7	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD2532	Approved
0.6988	Remote Similarity	NPD2533	Approved
0.6988	Remote Similarity	NPD2534	Approved
0.6975	Remote Similarity	NPD6004	Phase 3
0.6975	Remote Similarity	NPD6002	Phase 3
0.6975	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD6005	Phase 3
0.697	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7054	Approved
0.6954	Remote Similarity	NPD5494	Approved
0.6951	Remote Similarity	NPD3750	Approved
0.6927	Remote Similarity	NPD7472	Approved
0.6919	Remote Similarity	NPD5402	Approved
0.6919	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD1551	Phase 2
0.6914	Remote Similarity	NPD8127	Discontinued
0.6914	Remote Similarity	NPD2935	Discontinued
0.6901	Remote Similarity	NPD6801	Discontinued
0.6899	Remote Similarity	NPD2313	Discontinued
0.689	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.689	Remote Similarity	NPD2800	Approved
0.6889	Remote Similarity	NPD6797	Phase 2
0.6885	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8404	Phase 2
0.6882	Remote Similarity	NPD4380	Phase 2
0.6882	Remote Similarity	NPD6599	Discontinued
0.6879	Remote Similarity	NPD6832	Phase 2
0.6879	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD7768	Phase 2
0.6872	Remote Similarity	NPD5844	Phase 1
0.686	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3748	Approved
0.6851	Remote Similarity	NPD7251	Discontinued
0.6851	Remote Similarity	NPD7685	Pre-registration
0.6836	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD1549	Phase 2
0.6826	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7458	Discontinued
0.6813	Remote Similarity	NPD7808	Phase 3
0.681	Remote Similarity	NPD2796	Approved
0.6805	Remote Similarity	NPD5403	Approved
0.6805	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.68	Remote Similarity	NPD919	Approved
0.6798	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD1243	Approved
0.6786	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD5401	Approved
0.677	Remote Similarity	NPD1933	Approved
0.6768	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6765	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6752	Remote Similarity	NPD2798	Approved
0.6748	Remote Similarity	NPD7033	Discontinued
0.6726	Remote Similarity	NPD6799	Approved
0.6724	Remote Similarity	NPD3817	Phase 2
0.6723	Remote Similarity	NPD6959	Discontinued
0.6722	Remote Similarity	NPD3751	Discontinued
0.671	Remote Similarity	NPD9717	Approved
0.6705	Remote Similarity	NPD1934	Approved
0.6701	Remote Similarity	NPD7435	Discontinued
0.6688	Remote Similarity	NPD2797	Approved
0.6687	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7097	Phase 1
0.6687	Remote Similarity	NPD3764	Approved
0.6685	Remote Similarity	NPD6232	Discontinued
0.6684	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD2344	Approved
0.6667	Remote Similarity	NPD1653	Approved
0.6667	Remote Similarity	NPD447	Suspended
0.6647	Remote Similarity	NPD7003	Approved
0.6646	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6777	Approved
0.6632	Remote Similarity	NPD6780	Approved
0.6632	Remote Similarity	NPD6779	Approved
0.6632	Remote Similarity	NPD6778	Approved
0.6632	Remote Similarity	NPD6776	Approved
0.6632	Remote Similarity	NPD6782	Approved
0.6632	Remote Similarity	NPD6781	Approved
0.6629	Remote Similarity	NPD1247	Approved
0.6625	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6166	Phase 2
0.6611	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4140	Approved
0.6603	Remote Similarity	NPD1608	Approved
0.6593	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6592	Remote Similarity	NPD5710	Approved
0.6592	Remote Similarity	NPD3787	Discontinued
0.6592	Remote Similarity	NPD5711	Approved
0.6592	Remote Similarity	NPD7229	Phase 3
0.6591	Remote Similarity	NPD3882	Suspended
0.659	Remote Similarity	NPD7028	Phase 2
0.6588	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6584	Remote Similarity	NPD3268	Approved
0.6584	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD1203	Approved
0.6568	Remote Similarity	NPD7236	Approved
0.6564	Remote Similarity	NPD5124	Phase 1
0.6564	Remote Similarity	NPD6355	Discontinued
0.6564	Remote Similarity	NPD6823	Phase 2
0.6564	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD8407	Phase 2
0.6552	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.655	Remote Similarity	NPD7783	Phase 2
0.655	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD4308	Phase 3
0.6545	Remote Similarity	NPD1510	Phase 2
0.6541	Remote Similarity	NPD1019	Discontinued
0.6538	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD1091	Approved
0.6535	Remote Similarity	NPD7930	Approved
0.6531	Remote Similarity	NPD7696	Phase 3
0.6531	Remote Similarity	NPD7698	Approved
0.6531	Remote Similarity	NPD7697	Approved
0.6531	Remote Similarity	NPD7680	Approved
0.6528	Remote Similarity	NPD4420	Approved
0.6522	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD2309	Approved
0.6506	Remote Similarity	NPD6100	Approved
0.6506	Remote Similarity	NPD6099	Approved
0.6503	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7874	Approved
0.65	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD7870	Phase 2
0.6497	Remote Similarity	NPD7871	Phase 2
0.6495	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD8150	Discontinued
0.6486	Remote Similarity	NPD8368	Discontinued
0.6481	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD411	Approved
0.6477	Remote Similarity	NPD1465	Phase 2
0.6477	Remote Similarity	NPD2801	Approved
0.6474	Remote Similarity	NPD7239	Suspended
0.6467	Remote Similarity	NPD7266	Discontinued
0.6464	Remote Similarity	NPD3926	Phase 2
0.645	Remote Similarity	NPD8151	Discontinued
0.645	Remote Similarity	NPD4110	Phase 3
0.645	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD8032	Phase 2
0.6438	Remote Similarity	NPD5647	Approved
0.6432	Remote Similarity	NPD5953	Discontinued
0.6429	Remote Similarity	NPD2424	Discontinued
0.6424	Remote Similarity	NPD6651	Approved
0.642	Remote Similarity	NPD6844	Discontinued
0.6414	Remote Similarity	NPD8320	Phase 1
0.6414	Remote Similarity	NPD8319	Approved
0.641	Remote Similarity	NPD1778	Approved
0.641	Remote Similarity	NPD17	Approved
0.6409	Remote Similarity	NPD6808	Phase 2

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