NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	380.18
Volume:	379.793
LogP:	0.396
LogD:	0.582
LogS:	-2.04
# Rotatable Bonds:	6
TPSA:	110.13
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.416
Synthetic Accessibility Score:	4.978
Fsp3:	0.75
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	3
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.993
MDCK Permeability:	0.00012542335025500506
Pgp-inhibitor:	0.001
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.061
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.174

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.426
Plasma Protein Binding (PPB):	48.32459259033203%
Volume Distribution (VD):	0.649
Pgp-substrate:	70.4761962890625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.014
CYP2C19-substrate:	0.238
CYP2C9-inhibitor:	0.009
CYP2C9-substrate:	0.087
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.073
CYP3A4-inhibitor:	0.357
CYP3A4-substrate:	0.226

ADMET: Excretion

Clearance (CL):	6.369
Half-life (T1/2):	0.88

ADMET: Toxicity

hERG Blockers:	0.076
Human Hepatotoxicity (H-HT):	0.765
Drug-inuced Liver Injury (DILI):	0.767
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.536
Skin Sensitization:	0.907
Carcinogencity:	0.036
Eye Corrosion:	0.005
Eye Irritation:	0.02
Respiratory Toxicity:	0.165

Download Data

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

Natural Product: NPC476806

Natural Product ID:	NPC476806
*Common Name:**	[(3R,3aR,4S,5aR,6R,9R,9bR)-9-formyl-6-hydroxy-3,5a-dimethyl-2-oxo-3,3a,4,5,6,7,8,9,9a,9b-decahydrobenzo[g][1]benzofuran-4-yl] 4-hydroxy-2-methylidenebutanoate
IUPAC Name:	[(3R,3aR,4S,5aR,6R,9R,9bR)-9-formyl-6-hydroxy-3,5a-dimethyl-2-oxo-3,3a,4,5,6,7,8,9,9a,9b-decahydrobenzo[g][1]benzofuran-4-yl] 4-hydroxy-2-methylidenebutanoate
Synonyms:
Standard InCHIKey:	OWTWBLYOTMJQME-ZTNIVYPMSA-N
Standard InCHI:	InChI=1S/C20H28O7/c1-10(6-7-21)18(24)26-13-8-20(3)14(23)5-4-12(9-22)16(20)17-15(13)11(2)19(25)27-17/h9,11-17,21,23H,1,4-8H2,2-3H3/t11-,12+,13+,14-,15-,16?,17+,20+/m1/s1
SMILES:	C[C@@H]1[C@@H]2[C@H](C[C@]3([C@@H](CC[C@H](C3[C@H]2OC1=O)C=O)O)C)OC(=O)C(=C)CCO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44445514
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001543] Sesquiterpene lactones [CHEMONTID:0001772] Eudesmanolides, secoeudesmanolides, and derivatives

*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
NPO10212	Centaurea pullata	Species	Asteraceae	Eukaryota	Aerial parts	Chra Mountain in Blida (North Algeria)	2006-APR	PMID[17979247]
NPO10212	Centaurea pullata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18280170]
NPO10212	Centaurea pullata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
MIC	14
Others	14

Activity Type	# Activity
Organism	28

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.2	ug/ml	PMID[17979247]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	=	0.3	ug/ml	PMID[17979247]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.2	ug/ml	PMID[17979247]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MBC	=	0.3	ug/ml	PMID[17979247]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MIC	=	0.4	ug/ml	PMID[17979247]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MBC	=	0.5	ug/ml	PMID[17979247]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	0.4	ug/ml	PMID[17979247]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	=	0.5	ug/ml	PMID[17979247]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MIC	=	0.4	ug/ml	PMID[17979247]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MBC	=	0.4	ug/ml	PMID[17979247]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	0.4	ug/ml	PMID[17979247]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	0.4	ug/ml	PMID[17979247]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	=	0.2	ug/ml	PMID[17979247]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MFC	=	0.3	ug/ml	PMID[17979247]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	0.2	ug/ml	PMID[17979247]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MFC	=	0.3	ug/ml	PMID[17979247]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MIC	=	0.2	ug/ml	PMID[17979247]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MFC	=	0.3	ug/ml	PMID[17979247]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MIC	=	0.3	ug/ml	PMID[17979247]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MFC	=	0.4	ug/ml	PMID[17979247]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MIC	=	0.3	ug/ml	PMID[17979247]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MFC	=	0.4	ug/ml	PMID[17979247]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MIC	=	0.3	ug/ml	PMID[17979247]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MFC	=	0.4	ug/ml	PMID[17979247]
NPT4945	Organism	Fusarium tricinctum	Fusarium tricinctum	MIC	=	0.2	ug/ml	PMID[17979247]
NPT4945	Organism	Fusarium tricinctum	Fusarium tricinctum	MFC	=	0.3	ug/ml	PMID[17979247]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	=	0.2	ug/ml	PMID[17979247]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MFC	=	0.3	ug/ml	PMID[17979247]

☑ 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 NPC476806 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	227
0.1-0.2	1515
0.2-0.3	5096
0.3-0.4	8410
0.4-0.5	12601
0.5-0.6	6231
0.6-0.7	6469
0.7-0.8	1948
0.8-0.85	136
0.85-0.9	38
0.9-0.95	24
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476807
0.9457	High Similarity	NPC259042
0.9457	High Similarity	NPC157686
0.9348	High Similarity	NPC225474
0.9348	High Similarity	NPC148000
0.9348	High Similarity	NPC469596
0.9286	High Similarity	NPC78966
0.9286	High Similarity	NPC284732
0.9255	High Similarity	NPC473963
0.9192	High Similarity	NPC37628
0.9167	High Similarity	NPC475958
0.9149	High Similarity	NPC93245
0.9149	High Similarity	NPC473964
0.914	High Similarity	NPC24861
0.91	High Similarity	NPC474243
0.9062	High Similarity	NPC47024
0.9022	High Similarity	NPC475776
0.8947	High Similarity	NPC228766
0.8947	High Similarity	NPC284518
0.8947	High Similarity	NPC165528
0.8913	High Similarity	NPC116620
0.8878	High Similarity	NPC164551
0.8854	High Similarity	NPC136781
0.8854	High Similarity	NPC474921
0.8842	High Similarity	NPC90014
0.8788	High Similarity	NPC61442
0.8788	High Similarity	NPC156681
0.8776	High Similarity	NPC242666
0.8763	High Similarity	NPC216478
0.8737	High Similarity	NPC474841
0.8737	High Similarity	NPC473434
0.8737	High Similarity	NPC471446
0.871	High Similarity	NPC194642
0.8696	High Similarity	NPC175293
0.8696	High Similarity	NPC305029
0.8646	High Similarity	NPC56369
0.8632	High Similarity	NPC147272
0.8587	High Similarity	NPC185638
0.8587	High Similarity	NPC85698
0.8586	High Similarity	NPC308824
0.8586	High Similarity	NPC111292
0.8571	High Similarity	NPC20479
0.8571	High Similarity	NPC162459
0.8571	High Similarity	NPC38471
0.8571	High Similarity	NPC98837
0.8571	High Similarity	NPC28864
0.8571	High Similarity	NPC38296
0.8571	High Similarity	NPC89099
0.85	High Similarity	NPC170615
0.8495	Intermediate Similarity	NPC181103
0.8485	Intermediate Similarity	NPC293890
0.8485	Intermediate Similarity	NPC293866
0.8469	Intermediate Similarity	NPC10864
0.8469	Intermediate Similarity	NPC474395
0.8462	Intermediate Similarity	NPC15091
0.8447	Intermediate Similarity	NPC275539
0.8447	Intermediate Similarity	NPC189075
0.8421	Intermediate Similarity	NPC153853
0.8416	Intermediate Similarity	NPC120321
0.8416	Intermediate Similarity	NPC99510
0.8416	Intermediate Similarity	NPC96217
0.8416	Intermediate Similarity	NPC72842
0.84	Intermediate Similarity	NPC148279
0.84	Intermediate Similarity	NPC46848
0.8387	Intermediate Similarity	NPC9231
0.837	Intermediate Similarity	NPC97505
0.8367	Intermediate Similarity	NPC256227
0.8367	Intermediate Similarity	NPC219353
0.8367	Intermediate Similarity	NPC200054
0.8367	Intermediate Similarity	NPC29410
0.835	Intermediate Similarity	NPC110496
0.8317	Intermediate Similarity	NPC88203
0.8317	Intermediate Similarity	NPC148628
0.8317	Intermediate Similarity	NPC246736
0.8317	Intermediate Similarity	NPC275990
0.8317	Intermediate Similarity	NPC214946
0.8317	Intermediate Similarity	NPC76866
0.8317	Intermediate Similarity	NPC476081
0.8317	Intermediate Similarity	NPC286519
0.8317	Intermediate Similarity	NPC304832
0.8298	Intermediate Similarity	NPC470012
0.8283	Intermediate Similarity	NPC111348
0.8265	Intermediate Similarity	NPC98639
0.8252	Intermediate Similarity	NPC469607
0.8252	Intermediate Similarity	NPC28791
0.8252	Intermediate Similarity	NPC295366
0.8242	Intermediate Similarity	NPC475743
0.8235	Intermediate Similarity	NPC87927
0.8218	Intermediate Similarity	NPC253886
0.8218	Intermediate Similarity	NPC289148
0.8218	Intermediate Similarity	NPC163963
0.8218	Intermediate Similarity	NPC52899
0.8218	Intermediate Similarity	NPC471412
0.8218	Intermediate Similarity	NPC121218
0.8208	Intermediate Similarity	NPC474846
0.8208	Intermediate Similarity	NPC469656
0.8208	Intermediate Similarity	NPC469655
0.82	Intermediate Similarity	NPC26270
0.82	Intermediate Similarity	NPC471038
0.82	Intermediate Similarity	NPC474793
0.8191	Intermediate Similarity	NPC477920
0.8173	Intermediate Similarity	NPC86852
0.8173	Intermediate Similarity	NPC251824
0.8163	Intermediate Similarity	NPC250075
0.8163	Intermediate Similarity	NPC272635
0.8163	Intermediate Similarity	NPC169751
0.8163	Intermediate Similarity	NPC66581
0.8155	Intermediate Similarity	NPC84928
0.8155	Intermediate Similarity	NPC283850
0.8155	Intermediate Similarity	NPC301787
0.8152	Intermediate Similarity	NPC226988
0.8144	Intermediate Similarity	NPC186363
0.8144	Intermediate Similarity	NPC233345
0.8137	Intermediate Similarity	NPC162973
0.8131	Intermediate Similarity	NPC194951
0.8131	Intermediate Similarity	NPC12046
0.8119	Intermediate Similarity	NPC287676
0.8119	Intermediate Similarity	NPC267921
0.8119	Intermediate Similarity	NPC471413
0.8113	Intermediate Similarity	NPC124053
0.8113	Intermediate Similarity	NPC478209
0.81	Intermediate Similarity	NPC474343
0.8095	Intermediate Similarity	NPC218123
0.8095	Intermediate Similarity	NPC476802
0.8095	Intermediate Similarity	NPC112895
0.8095	Intermediate Similarity	NPC273155
0.8095	Intermediate Similarity	NPC89171
0.8095	Intermediate Similarity	NPC231278
0.8095	Intermediate Similarity	NPC306265
0.8081	Intermediate Similarity	NPC470232
0.8077	Intermediate Similarity	NPC37600
0.8077	Intermediate Similarity	NPC478208
0.8077	Intermediate Similarity	NPC138908
0.8077	Intermediate Similarity	NPC200957
0.8077	Intermediate Similarity	NPC222833
0.8061	Intermediate Similarity	NPC294263
0.8061	Intermediate Similarity	NPC199543
0.8058	Intermediate Similarity	NPC216114
0.8058	Intermediate Similarity	NPC139347
0.8058	Intermediate Similarity	NPC254202
0.8056	Intermediate Similarity	NPC157441
0.8056	Intermediate Similarity	NPC25909
0.8043	Intermediate Similarity	NPC209318
0.8043	Intermediate Similarity	NPC223330
0.8041	Intermediate Similarity	NPC158488
0.8039	Intermediate Similarity	NPC471790
0.8039	Intermediate Similarity	NPC295276
0.8039	Intermediate Similarity	NPC236585
0.8039	Intermediate Similarity	NPC39683
0.8039	Intermediate Similarity	NPC252614
0.8037	Intermediate Similarity	NPC94650
0.8021	Intermediate Similarity	NPC277771
0.8021	Intermediate Similarity	NPC50847
0.802	Intermediate Similarity	NPC23364
0.802	Intermediate Similarity	NPC473155
0.802	Intermediate Similarity	NPC78427
0.802	Intermediate Similarity	NPC16911
0.8	Intermediate Similarity	NPC471246
0.8	Intermediate Similarity	NPC176949
0.8	Intermediate Similarity	NPC13949
0.8	Intermediate Similarity	NPC329910
0.8	Intermediate Similarity	NPC264979
0.8	Intermediate Similarity	NPC134072
0.8	Intermediate Similarity	NPC234993
0.8	Intermediate Similarity	NPC201908
0.8	Intermediate Similarity	NPC135548
0.8	Intermediate Similarity	NPC96333
0.8	Intermediate Similarity	NPC179380
0.8	Intermediate Similarity	NPC187435
0.8	Intermediate Similarity	NPC88833
0.8	Intermediate Similarity	NPC67321
0.8	Intermediate Similarity	NPC61071
0.8	Intermediate Similarity	NPC166993
0.7981	Intermediate Similarity	NPC47281
0.7981	Intermediate Similarity	NPC477127
0.7981	Intermediate Similarity	NPC474558
0.7981	Intermediate Similarity	NPC98603
0.7981	Intermediate Similarity	NPC13149
0.7981	Intermediate Similarity	NPC202793
0.798	Intermediate Similarity	NPC470385
0.798	Intermediate Similarity	NPC470386
0.798	Intermediate Similarity	NPC57117
0.798	Intermediate Similarity	NPC475118
0.7979	Intermediate Similarity	NPC470011
0.7963	Intermediate Similarity	NPC476964
0.7963	Intermediate Similarity	NPC269530
0.7961	Intermediate Similarity	NPC165250
0.7961	Intermediate Similarity	NPC469606
0.7961	Intermediate Similarity	NPC31058
0.7961	Intermediate Similarity	NPC273005
0.7961	Intermediate Similarity	NPC295791
0.7959	Intermediate Similarity	NPC72845
0.7944	Intermediate Similarity	NPC100908
0.7944	Intermediate Similarity	NPC253906
0.7944	Intermediate Similarity	NPC5103
0.7941	Intermediate Similarity	NPC470388
0.7925	Intermediate Similarity	NPC476479
0.7921	Intermediate Similarity	NPC91695
0.7921	Intermediate Similarity	NPC96839
0.7921	Intermediate Similarity	NPC70145

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 NPC476806 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	218
0.1-0.2	2015
0.2-0.3	3813
0.3-0.4	2020
0.4-0.5	612
0.5-0.6	233
0.6-0.7	183
0.7-0.8	56
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7593	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4225	Approved
0.75	Intermediate Similarity	NPD7638	Approved
0.7429	Intermediate Similarity	NPD7640	Approved
0.7429	Intermediate Similarity	NPD7639	Approved
0.7364	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD8034	Phase 2
0.7255	Intermediate Similarity	NPD8035	Phase 2
0.7248	Intermediate Similarity	NPD6008	Approved
0.7182	Intermediate Similarity	NPD5697	Approved
0.7167	Intermediate Similarity	NPD7507	Approved
0.7131	Intermediate Similarity	NPD7319	Approved
0.7117	Intermediate Similarity	NPD6899	Approved
0.7117	Intermediate Similarity	NPD6881	Approved
0.7117	Intermediate Similarity	NPD6686	Approved
0.7091	Intermediate Similarity	NPD7128	Approved
0.7091	Intermediate Similarity	NPD6675	Approved
0.7091	Intermediate Similarity	NPD6402	Approved
0.7091	Intermediate Similarity	NPD5739	Approved
0.708	Intermediate Similarity	NPD6649	Approved
0.708	Intermediate Similarity	NPD6650	Approved
0.7054	Intermediate Similarity	NPD6013	Approved
0.7054	Intermediate Similarity	NPD6372	Approved
0.7054	Intermediate Similarity	NPD6014	Approved
0.7054	Intermediate Similarity	NPD6012	Approved
0.7054	Intermediate Similarity	NPD6373	Approved
0.7048	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5701	Approved
0.7027	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD6399	Phase 3
0.7	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.6991	Remote Similarity	NPD6883	Approved
0.6991	Remote Similarity	NPD7290	Approved
0.6991	Remote Similarity	NPD7102	Approved
0.6981	Remote Similarity	NPD4697	Phase 3
0.6972	Remote Similarity	NPD7632	Discontinued
0.6964	Remote Similarity	NPD7320	Approved
0.6964	Remote Similarity	NPD6011	Approved
0.6957	Remote Similarity	NPD8133	Approved
0.6957	Remote Similarity	NPD4632	Approved
0.693	Remote Similarity	NPD6847	Approved
0.693	Remote Similarity	NPD6617	Approved
0.693	Remote Similarity	NPD6869	Approved
0.693	Remote Similarity	NPD8130	Phase 1
0.6923	Remote Similarity	NPD7115	Discovery
0.6916	Remote Similarity	NPD7902	Approved
0.6891	Remote Similarity	NPD6319	Approved
0.687	Remote Similarity	NPD6882	Approved
0.687	Remote Similarity	NPD8297	Approved
0.6869	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD6921	Approved
0.6832	Remote Similarity	NPD1694	Approved
0.6818	Remote Similarity	NPD5211	Phase 2
0.6804	Remote Similarity	NPD6697	Approved
0.6804	Remote Similarity	NPD6118	Approved
0.6804	Remote Similarity	NPD6115	Approved
0.6804	Remote Similarity	NPD6114	Approved
0.6803	Remote Similarity	NPD7492	Approved
0.6792	Remote Similarity	NPD7748	Approved
0.6789	Remote Similarity	NPD5286	Approved
0.6789	Remote Similarity	NPD4696	Approved
0.6789	Remote Similarity	NPD5285	Approved
0.678	Remote Similarity	NPD6009	Approved
0.6765	Remote Similarity	NPD3618	Phase 1
0.6762	Remote Similarity	NPD7515	Phase 2
0.6762	Remote Similarity	NPD6079	Approved
0.6759	Remote Similarity	NPD4755	Approved
0.675	Remote Similarity	NPD6054	Approved
0.6748	Remote Similarity	NPD6616	Approved
0.6731	Remote Similarity	NPD5328	Approved
0.6724	Remote Similarity	NPD6053	Discontinued
0.6701	Remote Similarity	NPD6116	Phase 1
0.6698	Remote Similarity	NPD5779	Approved
0.6698	Remote Similarity	NPD5778	Approved
0.6696	Remote Similarity	NPD5141	Approved
0.6695	Remote Similarity	NPD6274	Approved
0.6694	Remote Similarity	NPD7078	Approved
0.6694	Remote Similarity	NPD6015	Approved
0.6694	Remote Similarity	NPD5983	Phase 2
0.6694	Remote Similarity	NPD6016	Approved
0.6667	Remote Similarity	NPD5225	Approved
0.6667	Remote Similarity	NPD4633	Approved
0.6667	Remote Similarity	NPD5226	Approved
0.6667	Remote Similarity	NPD5224	Approved
0.6667	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5222	Approved
0.6667	Remote Similarity	NPD3703	Phase 2
0.6667	Remote Similarity	NPD5221	Approved
0.664	Remote Similarity	NPD7736	Approved
0.6639	Remote Similarity	NPD6370	Approved
0.6639	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6639	Remote Similarity	NPD5988	Approved
0.6638	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7900	Approved
0.6636	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4700	Approved
0.6612	Remote Similarity	NPD6059	Approved
0.6609	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD5174	Approved
0.6607	Remote Similarity	NPD5175	Approved
0.6606	Remote Similarity	NPD5173	Approved
0.6604	Remote Similarity	NPD6411	Approved
0.6598	Remote Similarity	NPD6117	Approved
0.6585	Remote Similarity	NPD8328	Phase 3
0.6585	Remote Similarity	NPD7604	Phase 2
0.6577	Remote Similarity	NPD5223	Approved
0.6577	Remote Similarity	NPD5344	Discontinued
0.656	Remote Similarity	NPD8293	Discontinued
0.6557	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4634	Approved
0.6538	Remote Similarity	NPD3573	Approved
0.6535	Remote Similarity	NPD3667	Approved
0.6529	Remote Similarity	NPD7101	Approved
0.6529	Remote Similarity	NPD7100	Approved
0.6509	Remote Similarity	NPD46	Approved
0.6509	Remote Similarity	NPD6698	Approved
0.6505	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6317	Approved
0.648	Remote Similarity	NPD6336	Discontinued
0.6455	Remote Similarity	NPD6083	Phase 2
0.6455	Remote Similarity	NPD6084	Phase 2
0.6449	Remote Similarity	NPD7637	Suspended
0.6446	Remote Similarity	NPD7328	Approved
0.6446	Remote Similarity	NPD6314	Approved
0.6446	Remote Similarity	NPD6313	Approved
0.6446	Remote Similarity	NPD6335	Approved
0.6446	Remote Similarity	NPD7327	Approved
0.6435	Remote Similarity	NPD6412	Phase 2
0.6429	Remote Similarity	NPD1700	Approved
0.6423	Remote Similarity	NPD8515	Approved
0.6423	Remote Similarity	NPD8517	Approved
0.6423	Remote Similarity	NPD8516	Approved
0.6423	Remote Similarity	NPD8513	Phase 3
0.6417	Remote Similarity	NPD6868	Approved
0.6415	Remote Similarity	NPD1695	Approved
0.6415	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6101	Approved
0.641	Remote Similarity	NPD6371	Approved
0.6408	Remote Similarity	NPD4786	Approved
0.6396	Remote Similarity	NPD5696	Approved
0.6393	Remote Similarity	NPD7516	Approved
0.6392	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD4202	Approved
0.6379	Remote Similarity	NPD5128	Approved
0.6379	Remote Similarity	NPD4729	Approved
0.6379	Remote Similarity	NPD4730	Approved
0.6348	Remote Similarity	NPD4768	Approved
0.6348	Remote Similarity	NPD4767	Approved
0.6339	Remote Similarity	NPD6648	Approved
0.633	Remote Similarity	NPD5282	Discontinued
0.6316	Remote Similarity	NPD4754	Approved
0.6311	Remote Similarity	NPD4788	Approved
0.6293	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.629	Remote Similarity	NPD6909	Approved
0.629	Remote Similarity	NPD6908	Approved
0.629	Remote Similarity	NPD8296	Approved
0.629	Remote Similarity	NPD8380	Approved
0.629	Remote Similarity	NPD8033	Approved
0.629	Remote Similarity	NPD8379	Approved
0.629	Remote Similarity	NPD8378	Approved
0.629	Remote Similarity	NPD8335	Approved
0.6286	Remote Similarity	NPD6409	Approved
0.6286	Remote Similarity	NPD7334	Approved
0.6286	Remote Similarity	NPD5330	Approved
0.6286	Remote Similarity	NPD6684	Approved
0.6286	Remote Similarity	NPD7146	Approved
0.6286	Remote Similarity	NPD7521	Approved
0.6273	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD5695	Phase 3
0.6271	Remote Similarity	NPD5250	Approved
0.6271	Remote Similarity	NPD5247	Approved
0.6271	Remote Similarity	NPD5248	Approved
0.6271	Remote Similarity	NPD5249	Phase 3
0.6271	Remote Similarity	NPD5251	Approved
0.625	Remote Similarity	NPD3665	Phase 1
0.625	Remote Similarity	NPD3666	Approved
0.625	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3133	Approved
0.6231	Remote Similarity	NPD7260	Phase 2
0.6218	Remote Similarity	NPD5215	Approved
0.6218	Remote Similarity	NPD5217	Approved
0.6218	Remote Similarity	NPD5216	Approved
0.621	Remote Similarity	NPD8294	Approved
0.621	Remote Similarity	NPD8377	Approved
0.6204	Remote Similarity	NPD5785	Approved
0.6183	Remote Similarity	NPD6845	Suspended
0.6172	Remote Similarity	NPD8074	Phase 3
0.6168	Remote Similarity	NPD6903	Approved
0.6168	Remote Similarity	NPD6672	Approved
0.6168	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD5737	Approved
0.6162	Remote Similarity	NPD3702	Approved
0.616	Remote Similarity	NPD7503	Approved
0.6154	Remote Similarity	NPD6695	Phase 3
0.6147	Remote Similarity	NPD5693	Phase 1
0.6147	Remote Similarity	NPD7983	Approved
0.6146	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5135	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