NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	374.17
Volume:	371.185
LogP:	2.922
LogD:	2.505
LogS:	-4.461
# 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:	0.8
Synthetic Accessibility Score:	6.221
Fsp3:	0.667
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:	-4.766
MDCK Permeability:	2.205624696216546e-05
Pgp-inhibitor:	0.778
Pgp-substrate:	0.682
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.728
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.549
Plasma Protein Binding (PPB):	93.15452575683594%
Volume Distribution (VD):	2.737
Pgp-substrate:	3.723464250564575%

ADMET: Metabolism

CYP1A2-inhibitor:	0.048
CYP1A2-substrate:	0.83
CYP2C19-inhibitor:	0.265
CYP2C19-substrate:	0.654
CYP2C9-inhibitor:	0.452
CYP2C9-substrate:	0.042
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.367
CYP3A4-inhibitor:	0.809
CYP3A4-substrate:	0.272

ADMET: Excretion

Clearance (CL):	9.204
Half-life (T1/2):	0.506

ADMET: Toxicity

hERG Blockers:	0.271
Human Hepatotoxicity (H-HT):	0.493
Drug-inuced Liver Injury (DILI):	0.079
AMES Toxicity:	0.936
Rat Oral Acute Toxicity:	0.996
Maximum Recommended Daily Dose:	0.969
Skin Sensitization:	0.615
Carcinogencity:	0.958
Eye Corrosion:	0.004
Eye Irritation:	0.142
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC476942

Natural Product ID:	NPC476942
*Common Name:**	methyl (1R,2R,4S,6R,8S,9S,16S)-6-(furan-3-yl)-2-hydroxy-16-methyl-3,5-dioxatetracyclo[6.5.3.01,9.04,8]hexadec-12-ene-13-carboxylate
IUPAC Name:	methyl (1R,2R,4S,6R,8S,9S,16S)-6-(furan-3-yl)-2-hydroxy-16-methyl-3,5-dioxatetracyclo[6.5.3.01,9.04,8]hexadec-12-ene-13-carboxylate
Synonyms:
Standard InCHIKey:	FTIIWSAYPGBNDS-ISZXVOLMSA-N
Standard InCHI:	InChI=1S/C21H26O6/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/h4,7,9,11-12,15-16,18-19,23H,3,5-6,8,10H2,1-2H3/t12-,15+,16+,18+,19-,20-,21-/m0/s1
SMILES:	C[C@H]1CC[C@]23[C@H]([C@]14C[C@@H](O[C@H]4O[C@H]2O)C5=COC=C5)CCC=C3C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	90676775
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 NPC476942 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	312
0.1-0.2	1198
0.2-0.3	2759
0.3-0.4	5153
0.4-0.5	10417
0.5-0.6	11781
0.6-0.7	9599
0.7-0.8	1149
0.8-0.85	242
0.85-0.9	69
0.9-0.95	12
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476941
0.9929	High Similarity	NPC476937
0.9929	High Similarity	NPC476938
0.9586	High Similarity	NPC476940
0.9586	High Similarity	NPC476939
0.9375	High Similarity	NPC250228
0.9241	High Similarity	NPC10088
0.9178	High Similarity	NPC7388
0.9139	High Similarity	NPC262872
0.9085	High Similarity	NPC90953
0.9054	High Similarity	NPC476936
0.9041	High Similarity	NPC276676
0.9041	High Similarity	NPC346
0.9032	High Similarity	NPC100333
0.902	High Similarity	NPC211777
0.9	High Similarity	NPC57998
0.8961	High Similarity	NPC198047
0.8944	High Similarity	NPC310830
0.8936	High Similarity	NPC92941
0.8933	High Similarity	NPC147168
0.8904	High Similarity	NPC476944
0.8896	High Similarity	NPC207978
0.8861	High Similarity	NPC160818
0.8861	High Similarity	NPC169299
0.8859	High Similarity	NPC195325
0.8836	High Similarity	NPC267632
0.8816	High Similarity	NPC214541
0.8816	High Similarity	NPC44675
0.8816	High Similarity	NPC35000
0.8811	High Similarity	NPC470742
0.8811	High Similarity	NPC186626
0.8808	High Similarity	NPC469503
0.8797	High Similarity	NPC82602
0.8782	High Similarity	NPC146991
0.875	High Similarity	NPC178932
0.875	High Similarity	NPC476943
0.875	High Similarity	NPC30222
0.875	High Similarity	NPC220094
0.8726	High Similarity	NPC97574
0.8726	High Similarity	NPC93172
0.8707	High Similarity	NPC470741
0.8707	High Similarity	NPC223415
0.8701	High Similarity	NPC261597
0.8693	High Similarity	NPC469336
0.8684	High Similarity	NPC75906
0.8645	High Similarity	NPC475967
0.8645	High Similarity	NPC307383
0.8611	High Similarity	NPC146872
0.8609	High Similarity	NPC472654
0.8599	High Similarity	NPC419
0.8581	High Similarity	NPC472778
0.8581	High Similarity	NPC36655
0.8581	High Similarity	NPC299038
0.8581	High Similarity	NPC472776
0.8581	High Similarity	NPC187149
0.8581	High Similarity	NPC472777
0.8571	High Similarity	NPC264943
0.8571	High Similarity	NPC20500
0.8562	High Similarity	NPC44577
0.8523	High Similarity	NPC251865
0.8523	High Similarity	NPC142113
0.8521	High Similarity	NPC89133
0.8506	High Similarity	NPC282445
0.85	High Similarity	NPC95567
0.85	High Similarity	NPC319140
0.8491	Intermediate Similarity	NPC214600
0.8477	Intermediate Similarity	NPC221809
0.8477	Intermediate Similarity	NPC470941
0.8472	Intermediate Similarity	NPC471998
0.8471	Intermediate Similarity	NPC477402
0.8466	Intermediate Similarity	NPC262386
0.8462	Intermediate Similarity	NPC45101
0.8462	Intermediate Similarity	NPC472772
0.8452	Intermediate Similarity	NPC281258
0.8446	Intermediate Similarity	NPC205765
0.844	Intermediate Similarity	NPC207294
0.844	Intermediate Similarity	NPC112706
0.8431	Intermediate Similarity	NPC159927
0.8431	Intermediate Similarity	NPC469335
0.8428	Intermediate Similarity	NPC123088
0.8428	Intermediate Similarity	NPC470182
0.8418	Intermediate Similarity	NPC69028
0.8418	Intermediate Similarity	NPC5079
0.8408	Intermediate Similarity	NPC477403
0.84	Intermediate Similarity	NPC137295
0.8392	Intermediate Similarity	NPC298190
0.8392	Intermediate Similarity	NPC61788
0.8375	Intermediate Similarity	NPC472141
0.8369	Intermediate Similarity	NPC83178
0.8367	Intermediate Similarity	NPC236532
0.8365	Intermediate Similarity	NPC51568
0.8365	Intermediate Similarity	NPC472139
0.8365	Intermediate Similarity	NPC234660
0.8365	Intermediate Similarity	NPC165218
0.8355	Intermediate Similarity	NPC471174
0.8354	Intermediate Similarity	NPC335761
0.8344	Intermediate Similarity	NPC41182
0.8344	Intermediate Similarity	NPC249021
0.8333	Intermediate Similarity	NPC476946
0.8323	Intermediate Similarity	NPC476850
0.8323	Intermediate Similarity	NPC476861
0.8323	Intermediate Similarity	NPC472651
0.8322	Intermediate Similarity	NPC21460
0.8313	Intermediate Similarity	NPC472664
0.8313	Intermediate Similarity	NPC276551
0.8312	Intermediate Similarity	NPC476122
0.8312	Intermediate Similarity	NPC477404
0.8312	Intermediate Similarity	NPC470997
0.8312	Intermediate Similarity	NPC196864
0.8302	Intermediate Similarity	NPC472771
0.8302	Intermediate Similarity	NPC200782
0.8302	Intermediate Similarity	NPC149896
0.8298	Intermediate Similarity	NPC23086
0.8298	Intermediate Similarity	NPC46536
0.8298	Intermediate Similarity	NPC138139
0.8291	Intermediate Similarity	NPC474611
0.8291	Intermediate Similarity	NPC475226
0.8289	Intermediate Similarity	NPC262198
0.8288	Intermediate Similarity	NPC158525
0.828	Intermediate Similarity	NPC469485
0.8272	Intermediate Similarity	NPC472652
0.8272	Intermediate Similarity	NPC271235
0.8269	Intermediate Similarity	NPC34421
0.8269	Intermediate Similarity	NPC237259
0.8269	Intermediate Similarity	NPC98206
0.8267	Intermediate Similarity	NPC121158
0.8267	Intermediate Similarity	NPC473152
0.8261	Intermediate Similarity	NPC472670
0.8261	Intermediate Similarity	NPC307781
0.8261	Intermediate Similarity	NPC470875
0.8261	Intermediate Similarity	NPC478178
0.8258	Intermediate Similarity	NPC18135
0.8252	Intermediate Similarity	NPC120836
0.8252	Intermediate Similarity	NPC223063
0.825	Intermediate Similarity	NPC39986
0.825	Intermediate Similarity	NPC292389
0.825	Intermediate Similarity	NPC224394
0.825	Intermediate Similarity	NPC134254
0.825	Intermediate Similarity	NPC302369
0.825	Intermediate Similarity	NPC663
0.825	Intermediate Similarity	NPC469338
0.825	Intermediate Similarity	NPC477405
0.825	Intermediate Similarity	NPC472773
0.8239	Intermediate Similarity	NPC25255
0.8239	Intermediate Similarity	NPC472653
0.8235	Intermediate Similarity	NPC216755
0.8228	Intermediate Similarity	NPC173544
0.8228	Intermediate Similarity	NPC304692
0.8221	Intermediate Similarity	NPC472660
0.8217	Intermediate Similarity	NPC469850
0.8217	Intermediate Similarity	NPC92979
0.8217	Intermediate Similarity	NPC141538
0.8217	Intermediate Similarity	NPC296807
0.8217	Intermediate Similarity	NPC155939
0.8207	Intermediate Similarity	NPC471995
0.8205	Intermediate Similarity	NPC268905
0.8205	Intermediate Similarity	NPC33938
0.8205	Intermediate Similarity	NPC472672
0.8205	Intermediate Similarity	NPC476201
0.8204	Intermediate Similarity	NPC470938
0.8199	Intermediate Similarity	NPC271657
0.8199	Intermediate Similarity	NPC476857
0.8199	Intermediate Similarity	NPC469849
0.8199	Intermediate Similarity	NPC476856
0.8199	Intermediate Similarity	NPC470940
0.8199	Intermediate Similarity	NPC476858
0.8194	Intermediate Similarity	NPC46551
0.8187	Intermediate Similarity	NPC263432
0.8187	Intermediate Similarity	NPC472767
0.8187	Intermediate Similarity	NPC117986
0.8187	Intermediate Similarity	NPC18347
0.8187	Intermediate Similarity	NPC193798
0.8187	Intermediate Similarity	NPC82851
0.8176	Intermediate Similarity	NPC42400
0.8171	Intermediate Similarity	NPC159232
0.8169	Intermediate Similarity	NPC74612
0.8165	Intermediate Similarity	NPC60973
0.8165	Intermediate Similarity	NPC209364
0.8165	Intermediate Similarity	NPC104736
0.816	Intermediate Similarity	NPC471397
0.816	Intermediate Similarity	NPC472673
0.8158	Intermediate Similarity	NPC86935
0.8153	Intermediate Similarity	NPC253201
0.8153	Intermediate Similarity	NPC302054
0.8151	Intermediate Similarity	NPC470740
0.8151	Intermediate Similarity	NPC218838
0.8148	Intermediate Similarity	NPC23387
0.8141	Intermediate Similarity	NPC272590
0.8141	Intermediate Similarity	NPC471000
0.8133	Intermediate Similarity	NPC67003
0.8129	Intermediate Similarity	NPC211625
0.8129	Intermediate Similarity	NPC125182
0.8129	Intermediate Similarity	NPC69647
0.8129	Intermediate Similarity	NPC234494
0.8129	Intermediate Similarity	NPC329180
0.8125	Intermediate Similarity	NPC305016
0.8121	Intermediate Similarity	NPC472376
0.8117	Intermediate Similarity	NPC255414
0.8113	Intermediate Similarity	NPC286722
0.8113	Intermediate Similarity	NPC470118

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 NPC476942 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	841
0.2-0.3	1946
0.3-0.4	2695
0.4-0.5	2134
0.5-0.6	992
0.6-0.7	260
0.7-0.8	16
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
0.8217	Intermediate Similarity	NPD5760	Phase 2
0.8217	Intermediate Similarity	NPD5761	Phase 2
0.7602	Intermediate Similarity	NPD6559	Discontinued
0.7486	Intermediate Similarity	NPD8434	Phase 2
0.747	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD6765	Approved
0.7299	Intermediate Similarity	NPD6764	Approved
0.7233	Intermediate Similarity	NPD4628	Phase 3
0.7222	Intermediate Similarity	NPD6273	Approved
0.7216	Intermediate Similarity	NPD8312	Approved
0.7216	Intermediate Similarity	NPD8313	Approved
0.7152	Intermediate Similarity	NPD2346	Discontinued
0.7143	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD4965	Approved
0.7143	Intermediate Similarity	NPD4967	Phase 2
0.7135	Intermediate Similarity	NPD6785	Approved
0.7135	Intermediate Similarity	NPD6784	Approved
0.7125	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD920	Approved
0.7055	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD2799	Discontinued
0.7024	Intermediate Similarity	NPD7819	Suspended
0.7019	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD1551	Phase 2
0.6974	Remote Similarity	NPD1049	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD3818	Discontinued
0.6971	Remote Similarity	NPD7228	Approved
0.6968	Remote Similarity	NPD2313	Discontinued
0.6964	Remote Similarity	NPD37	Approved
0.6959	Remote Similarity	NPD6234	Discontinued
0.6951	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6937	Remote Similarity	NPD6004	Phase 3
0.6937	Remote Similarity	NPD6002	Phase 3
0.6937	Remote Similarity	NPD6005	Phase 3
0.6937	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6903	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3749	Approved
0.6886	Remote Similarity	NPD3226	Approved
0.6886	Remote Similarity	NPD7458	Discontinued
0.6848	Remote Similarity	NPD2532	Approved
0.6848	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD2534	Approved
0.6848	Remote Similarity	NPD2533	Approved
0.6845	Remote Similarity	NPD6599	Discontinued
0.6839	Remote Similarity	NPD6832	Phase 2
0.6836	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD1933	Approved
0.6829	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD8455	Phase 2
0.6818	Remote Similarity	NPD2798	Approved
0.6816	Remote Similarity	NPD7240	Approved
0.681	Remote Similarity	NPD3750	Approved
0.6805	Remote Similarity	NPD7411	Suspended
0.6802	Remote Similarity	NPD7075	Discontinued
0.678	Remote Similarity	NPD7799	Discontinued
0.6776	Remote Similarity	NPD9717	Approved
0.677	Remote Similarity	NPD2935	Discontinued
0.6753	Remote Similarity	NPD2797	Approved
0.6748	Remote Similarity	NPD2800	Approved
0.6748	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD7768	Phase 2
0.6742	Remote Similarity	NPD5844	Phase 1
0.6724	Remote Similarity	NPD5494	Approved
0.671	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD7033	Discontinued
0.6708	Remote Similarity	NPD4308	Phase 3
0.6708	Remote Similarity	NPD3748	Approved
0.6707	Remote Similarity	NPD7003	Approved
0.6704	Remote Similarity	NPD7074	Phase 3
0.6687	Remote Similarity	NPD1549	Phase 2
0.6687	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD7199	Phase 2
0.6686	Remote Similarity	NPD5402	Approved
0.6686	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6686	Remote Similarity	NPD8127	Discontinued
0.6685	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD8404	Phase 2
0.6667	Remote Similarity	NPD2796	Approved
0.6667	Remote Similarity	NPD5403	Approved
0.6667	Remote Similarity	NPD4140	Approved
0.6667	Remote Similarity	NPD6801	Discontinued
0.6667	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6648	Remote Similarity	NPD7054	Approved
0.6647	Remote Similarity	NPD4380	Phase 2
0.6647	Remote Similarity	NPD5401	Approved
0.6647	Remote Similarity	NPD4378	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD7028	Phase 2
0.6646	Remote Similarity	NPD3268	Approved
0.6646	Remote Similarity	NPD1243	Approved
0.6646	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD3764	Approved
0.6645	Remote Similarity	NPD1203	Approved
0.663	Remote Similarity	NPD7685	Pre-registration
0.6628	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD1471	Phase 3
0.6626	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6626	Remote Similarity	NPD2344	Approved
0.6625	Remote Similarity	NPD447	Suspended
0.6625	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD7472	Approved
0.6603	Remote Similarity	NPD1019	Discontinued
0.6603	Remote Similarity	NPD5647	Approved
0.6601	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD6799	Approved
0.6585	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD6797	Phase 2
0.6573	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD919	Approved
0.6569	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6568	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD4307	Phase 2
0.6558	Remote Similarity	NPD1608	Approved
0.6552	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6543	Remote Similarity	NPD7097	Phase 1
0.6541	Remote Similarity	NPD411	Approved
0.6538	Remote Similarity	NPD7251	Discontinued
0.6527	Remote Similarity	NPD7236	Approved
0.6522	Remote Similarity	NPD6355	Discontinued
0.6517	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6506	Remote Similarity	NPD4110	Phase 3
0.6506	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6503	Remote Similarity	NPD7808	Phase 3
0.65	Remote Similarity	NPD3751	Discontinued
0.65	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.65	Remote Similarity	NPD8032	Phase 2
0.6497	Remote Similarity	NPD6959	Discontinued
0.6495	Remote Similarity	NPD7435	Discontinued
0.6494	Remote Similarity	NPD1091	Approved
0.6474	Remote Similarity	NPD1934	Approved
0.6471	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1778	Approved
0.6467	Remote Similarity	NPD2309	Approved
0.6463	Remote Similarity	NPD6100	Approved
0.6463	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD6099	Approved
0.6461	Remote Similarity	NPD5711	Approved
0.6461	Remote Similarity	NPD5710	Approved
0.6461	Remote Similarity	NPD6232	Discontinued
0.646	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7473	Discontinued
0.6438	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD6362	Approved
0.6433	Remote Similarity	NPD3267	Approved
0.6433	Remote Similarity	NPD3266	Approved
0.6425	Remote Similarity	NPD6780	Approved
0.6425	Remote Similarity	NPD6777	Approved
0.6425	Remote Similarity	NPD6776	Approved
0.6425	Remote Similarity	NPD6781	Approved
0.6425	Remote Similarity	NPD6778	Approved
0.6425	Remote Similarity	NPD6779	Approved
0.6425	Remote Similarity	NPD6782	Approved
0.642	Remote Similarity	NPD5124	Phase 1
0.642	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6416	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD5585	Approved
0.6404	Remote Similarity	NPD1247	Approved
0.6402	Remote Similarity	NPD1510	Phase 2
0.64	Remote Similarity	NPD3817	Phase 2
0.64	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6398	Remote Similarity	NPD6233	Phase 2
0.6395	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6386	Remote Similarity	NPD2424	Discontinued
0.638	Remote Similarity	NPD6653	Approved
0.6379	Remote Similarity	NPD6844	Discontinued
0.6374	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6369	Remote Similarity	NPD6808	Phase 2
0.6369	Remote Similarity	NPD1283	Approved
0.6369	Remote Similarity	NPD7229	Phase 3
0.6369	Remote Similarity	NPD3787	Discontinued
0.6364	Remote Similarity	NPD8150	Discontinued
0.6364	Remote Similarity	NPD3882	Suspended
0.6364	Remote Similarity	NPD17	Approved
0.6359	Remote Similarity	NPD6823	Phase 2
0.6358	Remote Similarity	NPD2979	Phase 3
0.6353	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.635	Remote Similarity	NPD7783	Phase 2
0.635	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6347	Remote Similarity	NPD6674	Discontinued
0.6346	Remote Similarity	NPD3972	Approved
0.6344	Remote Similarity	NPD8407	Phase 2
0.6337	Remote Similarity	NPD1653	Approved
0.6337	Remote Similarity	NPD7239	Suspended
0.6335	Remote Similarity	NPD6798	Discontinued
0.6333	Remote Similarity	NPD1241	Discontinued
0.6327	Remote Similarity	NPD7696	Phase 3
0.6327	Remote Similarity	NPD7680	Approved
0.6327	Remote Similarity	NPD7697	Approved
0.6327	Remote Similarity	NPD7698	Approved
0.6325	Remote Similarity	NPD5763	Approved
0.6325	Remote Similarity	NPD5762	Approved
0.6321	Remote Similarity	NPD4420	Approved
0.6319	Remote Similarity	NPD5735	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