NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	282.15
Volume:	281.005
LogP:	0.379
LogD:	0.65
LogS:	-1.503
# Rotatable Bonds:	1
TPSA:	83.83
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.541
Synthetic Accessibility Score:	4.794
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.929
MDCK Permeability:	0.00013021712948102504
Pgp-inhibitor:	0.002
Pgp-substrate:	0.953
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.924

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.886
Plasma Protein Binding (PPB):	36.714691162109375%
Volume Distribution (VD):	1.095
Pgp-substrate:	73.14214324951172%

ADMET: Metabolism

CYP1A2-inhibitor:	0.028
CYP1A2-substrate:	0.214
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.689
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.133
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.2

ADMET: Excretion

Clearance (CL):	7.164
Half-life (T1/2):	0.863

ADMET: Toxicity

hERG Blockers:	0.078
Human Hepatotoxicity (H-HT):	0.374
Drug-inuced Liver Injury (DILI):	0.167
AMES Toxicity:	0.024
Rat Oral Acute Toxicity:	0.411
Maximum Recommended Daily Dose:	0.384
Skin Sensitization:	0.847
Carcinogencity:	0.045
Eye Corrosion:	0.12
Eye Irritation:	0.125
Respiratory Toxicity:	0.469

Download Data

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

Natural Product: NPC15091

Natural Product ID:	NPC15091
*Common Name:**	8-Alpha-Hydroxy-11B,13-Dihydro-4-Epi-Sonchucarpolide
IUPAC Name:	(3S,3aR,4S,5aR,6R,9S,9aS,9bR)-4,6-dihydroxy-3,5a-dimethyl-2-oxo-3,3a,4,5,6,7,8,9,9a,9b-decahydrobenzo[g][1]benzofuran-9-carbaldehyde
Synonyms:
Standard InCHIKey:	PJGXBSCTZLDUJY-YFUJPLHVSA-N
Standard InCHI:	InChI=1S/C15H22O5/c1-7-11-9(17)5-15(2)10(18)4-3-8(6-16)12(15)13(11)20-14(7)19/h6-13,17-18H,3-5H2,1-2H3/t7-,8+,9-,10+,11+,12+,13-,15-/m0/s1
SMILES:	O=C[C@H]1CC[C@H]([C@]2([C@H]1[C@H]1OC(=O)[C@H]([C@@H]1[C@H](C2)O)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL515375
PubChem CID:	44567329
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
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MBC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MBC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MIC	=	1.0	10'-3micromol/ml	PMID[457023]
NPT17	Organism	Staphylococcus epidermidis	Staphylococcus epidermidis	MBC	=	1.4	10'-3micromol/ml	PMID[457023]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	1.0	10'-3micromol/ml	PMID[457023]
NPT19	Organism	Escherichia coli	Escherichia coli	MBC	=	1.4	10'-3micromol/ml	PMID[457023]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MIC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT3729	Organism	Pseudomonas tolaasii	Pseudomonas tolaasii	MBC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MIC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MBC	=	1.0	10'-3micromol/ml	PMID[457023]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MIC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT2567	Organism	Trichoderma viride	Hypocrea rufa	MFC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MIC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT6344	Organism	Penicillium ochrochloron	Penicillium ochrochloron	MFC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MIC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT3695	Organism	Penicillium funiculosum	Penicillium funiculosum	MFC	=	0.7	10'-3micromol/ml	PMID[457023]
NPT4945	Organism	Fusarium tricinctum	Fusarium tricinctum	MIC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT4945	Organism	Fusarium tricinctum	Fusarium tricinctum	MFC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MIC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT3176	Organism	Aspergillus ochraceus	Aspergillus ochraceus	MFC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MIC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT21	Organism	Aspergillus niger	Aspergillus niger	MFC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MIC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT185	Organism	Aspergillus flavus	Aspergillus flavus	MFC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MIC	=	0.3	10'-3micromol/ml	PMID[457023]
NPT962	Organism	Alternaria alternata	Alternaria alternata	MFC	=	0.3	10'-3micromol/ml	PMID[457023]

☑ 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 NPC15091 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	356
0.1-0.2	2928
0.2-0.3	7582
0.3-0.4	14616
0.4-0.5	6354
0.5-0.6	6524
0.6-0.7	3570
0.7-0.8	697
0.8-0.85	57
0.85-0.9	11
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.974	High Similarity	NPC475743
0.8734	High Similarity	NPC143250
0.8734	High Similarity	NPC307865
0.8675	High Similarity	NPC473299
0.8675	High Similarity	NPC477434
0.8571	High Similarity	NPC473350
0.8571	High Similarity	NPC477445
0.8488	Intermediate Similarity	NPC476435
0.8462	Intermediate Similarity	NPC476806
0.8462	Intermediate Similarity	NPC476807
0.8415	Intermediate Similarity	NPC134227
0.8415	Intermediate Similarity	NPC125366
0.8409	Intermediate Similarity	NPC475878
0.8391	Intermediate Similarity	NPC471459
0.8391	Intermediate Similarity	NPC477443
0.8391	Intermediate Similarity	NPC67653
0.8391	Intermediate Similarity	NPC477440
0.8354	Intermediate Similarity	NPC55508
0.8295	Intermediate Similarity	NPC475211
0.8295	Intermediate Similarity	NPC477433
0.8295	Intermediate Similarity	NPC470114
0.8295	Intermediate Similarity	NPC477444
0.8295	Intermediate Similarity	NPC477442
0.8295	Intermediate Similarity	NPC88337
0.8276	Intermediate Similarity	NPC471221
0.8276	Intermediate Similarity	NPC131104
0.8276	Intermediate Similarity	NPC473319
0.8276	Intermediate Similarity	NPC3032
0.8256	Intermediate Similarity	NPC83242
0.8242	Intermediate Similarity	NPC235109
0.8182	Intermediate Similarity	NPC200580
0.8182	Intermediate Similarity	NPC194642
0.8161	Intermediate Similarity	NPC239938
0.8152	Intermediate Similarity	NPC472145
0.8148	Intermediate Similarity	NPC474020
0.814	Intermediate Similarity	NPC477205
0.8132	Intermediate Similarity	NPC62407
0.8132	Intermediate Similarity	NPC82633
0.8132	Intermediate Similarity	NPC287354
0.8111	Intermediate Similarity	NPC476189
0.8111	Intermediate Similarity	NPC147272
0.8068	Intermediate Similarity	NPC477614
0.8068	Intermediate Similarity	NPC226491
0.8068	Intermediate Similarity	NPC236459
0.8065	Intermediate Similarity	NPC472144
0.8046	Intermediate Similarity	NPC248216
0.8043	Intermediate Similarity	NPC475785
0.8043	Intermediate Similarity	NPC163685
0.8043	Intermediate Similarity	NPC193785
0.8043	Intermediate Similarity	NPC475765
0.8023	Intermediate Similarity	NPC237938
0.8023	Intermediate Similarity	NPC475689
0.8023	Intermediate Similarity	NPC97505
0.8023	Intermediate Similarity	NPC219535
0.8022	Intermediate Similarity	NPC470424
0.8022	Intermediate Similarity	NPC148000
0.8022	Intermediate Similarity	NPC225474
0.8022	Intermediate Similarity	NPC469596
0.8	Intermediate Similarity	NPC474755
0.8	Intermediate Similarity	NPC474065
0.8	Intermediate Similarity	NPC109510
0.7978	Intermediate Similarity	NPC61688
0.7955	Intermediate Similarity	NPC470920
0.7935	Intermediate Similarity	NPC157686
0.7935	Intermediate Similarity	NPC259042
0.7931	Intermediate Similarity	NPC476715
0.7907	Intermediate Similarity	NPC227170
0.7895	Intermediate Similarity	NPC475958
0.7889	Intermediate Similarity	NPC153853
0.7889	Intermediate Similarity	NPC77756
0.7889	Intermediate Similarity	NPC472146
0.7889	Intermediate Similarity	NPC185529
0.7882	Intermediate Similarity	NPC470156
0.7872	Intermediate Similarity	NPC98837
0.7872	Intermediate Similarity	NPC20479
0.7872	Intermediate Similarity	NPC38471
0.7872	Intermediate Similarity	NPC162459
0.7872	Intermediate Similarity	NPC474724
0.7872	Intermediate Similarity	NPC89099
0.7872	Intermediate Similarity	NPC253995
0.7872	Intermediate Similarity	NPC28864
0.7872	Intermediate Similarity	NPC38296
0.7865	Intermediate Similarity	NPC476379
0.7857	Intermediate Similarity	NPC80891
0.7857	Intermediate Similarity	NPC78966
0.7857	Intermediate Similarity	NPC284732
0.7857	Intermediate Similarity	NPC201276
0.7849	Intermediate Similarity	NPC116683
0.7849	Intermediate Similarity	NPC256227
0.7849	Intermediate Similarity	NPC93245
0.7841	Intermediate Similarity	NPC302111
0.7841	Intermediate Similarity	NPC474215
0.7841	Intermediate Similarity	NPC476717
0.7841	Intermediate Similarity	NPC477441
0.7841	Intermediate Similarity	NPC475729
0.7826	Intermediate Similarity	NPC24861
0.7816	Intermediate Similarity	NPC65133
0.7816	Intermediate Similarity	NPC9060
0.7816	Intermediate Similarity	NPC79308
0.7816	Intermediate Similarity	NPC473336
0.7816	Intermediate Similarity	NPC181871
0.7816	Intermediate Similarity	NPC471044
0.7802	Intermediate Similarity	NPC216137
0.7802	Intermediate Similarity	NPC52756
0.7791	Intermediate Similarity	NPC477447
0.7791	Intermediate Similarity	NPC477446
0.7791	Intermediate Similarity	NPC470155
0.7789	Intermediate Similarity	NPC293890
0.7789	Intermediate Similarity	NPC293866
0.7778	Intermediate Similarity	NPC37628
0.7766	Intermediate Similarity	NPC10864
0.7766	Intermediate Similarity	NPC473963
0.7766	Intermediate Similarity	NPC471241
0.7765	Intermediate Similarity	NPC472951
0.7765	Intermediate Similarity	NPC477851
0.7765	Intermediate Similarity	NPC472943
0.7738	Intermediate Similarity	NPC475725
0.7738	Intermediate Similarity	NPC224802
0.7738	Intermediate Similarity	NPC171426
0.7738	Intermediate Similarity	NPC324700
0.7738	Intermediate Similarity	NPC34046
0.7738	Intermediate Similarity	NPC80089
0.7732	Intermediate Similarity	NPC96217
0.7727	Intermediate Similarity	NPC478111
0.7727	Intermediate Similarity	NPC474572
0.7727	Intermediate Similarity	NPC62572
0.7708	Intermediate Similarity	NPC253886
0.7708	Intermediate Similarity	NPC46848
0.7708	Intermediate Similarity	NPC148279
0.7708	Intermediate Similarity	NPC121218
0.77	Intermediate Similarity	NPC474243
0.7692	Intermediate Similarity	NPC18536
0.7692	Intermediate Similarity	NPC50443
0.7674	Intermediate Similarity	NPC280781
0.7674	Intermediate Similarity	NPC470154
0.7674	Intermediate Similarity	NPC476071
0.7674	Intermediate Similarity	NPC209318
0.7674	Intermediate Similarity	NPC48756
0.7674	Intermediate Similarity	NPC223330
0.7674	Intermediate Similarity	NPC58631
0.766	Intermediate Similarity	NPC165528
0.766	Intermediate Similarity	NPC219353
0.766	Intermediate Similarity	NPC200054
0.766	Intermediate Similarity	NPC228766
0.766	Intermediate Similarity	NPC473964
0.766	Intermediate Similarity	NPC29410
0.7653	Intermediate Similarity	NPC88469
0.7647	Intermediate Similarity	NPC320144
0.764	Intermediate Similarity	NPC472272
0.764	Intermediate Similarity	NPC120395
0.7634	Intermediate Similarity	NPC309127
0.7634	Intermediate Similarity	NPC247877
0.7629	Intermediate Similarity	NPC170615
0.7629	Intermediate Similarity	NPC244969
0.7629	Intermediate Similarity	NPC213528
0.7629	Intermediate Similarity	NPC275990
0.7629	Intermediate Similarity	NPC471254
0.7619	Intermediate Similarity	NPC207010
0.7619	Intermediate Similarity	NPC317913
0.7614	Intermediate Similarity	NPC50438
0.7614	Intermediate Similarity	NPC291310
0.7604	Intermediate Similarity	NPC47024
0.759	Intermediate Similarity	NPC159789
0.7586	Intermediate Similarity	NPC268040
0.7586	Intermediate Similarity	NPC121121
0.7586	Intermediate Similarity	NPC61107
0.7586	Intermediate Similarity	NPC208912
0.7586	Intermediate Similarity	NPC289486
0.7586	Intermediate Similarity	NPC2096
0.7582	Intermediate Similarity	NPC56962
0.7582	Intermediate Similarity	NPC24705
0.7582	Intermediate Similarity	NPC116620
0.7579	Intermediate Similarity	NPC472273
0.7579	Intermediate Similarity	NPC136781
0.7558	Intermediate Similarity	NPC474714
0.7553	Intermediate Similarity	NPC17336
0.7553	Intermediate Similarity	NPC90014
0.7553	Intermediate Similarity	NPC98639
0.7529	Intermediate Similarity	NPC191345
0.7529	Intermediate Similarity	NPC185465
0.7529	Intermediate Similarity	NPC472608
0.7529	Intermediate Similarity	NPC252483
0.7527	Intermediate Similarity	NPC161035
0.7526	Intermediate Similarity	NPC295276
0.7526	Intermediate Similarity	NPC39683
0.7526	Intermediate Similarity	NPC259654
0.7526	Intermediate Similarity	NPC298266
0.75	Intermediate Similarity	NPC4209
0.75	Intermediate Similarity	NPC471038
0.75	Intermediate Similarity	NPC474253
0.75	Intermediate Similarity	NPC474346
0.75	Intermediate Similarity	NPC216478
0.75	Intermediate Similarity	NPC474793
0.75	Intermediate Similarity	NPC474284
0.75	Intermediate Similarity	NPC26270
0.75	Intermediate Similarity	NPC471046
0.75	Intermediate Similarity	NPC475776
0.75	Intermediate Similarity	NPC213737
0.75	Intermediate Similarity	NPC475820
0.75	Intermediate Similarity	NPC471246

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 NPC15091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	396
0.1-0.2	3325
0.2-0.3	3455
0.3-0.4	1203
0.4-0.5	382
0.5-0.6	239
0.6-0.7	136
0.7-0.8	14
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
0.7738	Intermediate Similarity	NPD6697	Approved
0.7738	Intermediate Similarity	NPD6115	Approved
0.7738	Intermediate Similarity	NPD6118	Approved
0.7738	Intermediate Similarity	NPD6114	Approved
0.7619	Intermediate Similarity	NPD6116	Phase 1
0.759	Intermediate Similarity	NPD3703	Phase 2
0.75	Intermediate Similarity	NPD6117	Approved
0.7347	Intermediate Similarity	NPD1700	Approved
0.7262	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3702	Approved
0.6875	Remote Similarity	NPD8035	Phase 2
0.6875	Remote Similarity	NPD8034	Phase 2
0.6824	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD1779	Approved
0.6703	Remote Similarity	NPD1780	Approved
0.6698	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD229	Approved
0.6636	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD5777	Approved
0.6627	Remote Similarity	NPD4224	Phase 2
0.6596	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD3698	Phase 2
0.6571	Remote Similarity	NPD6008	Approved
0.6571	Remote Similarity	NPD5739	Approved
0.6571	Remote Similarity	NPD7128	Approved
0.6571	Remote Similarity	NPD6675	Approved
0.6571	Remote Similarity	NPD6402	Approved
0.6542	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6372	Approved
0.6542	Remote Similarity	NPD6373	Approved
0.6512	Remote Similarity	NPD4245	Approved
0.6512	Remote Similarity	NPD4244	Approved
0.6509	Remote Similarity	NPD5697	Approved
0.6509	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD7638	Approved
0.6465	Remote Similarity	NPD6399	Phase 3
0.6449	Remote Similarity	NPD6881	Approved
0.6449	Remote Similarity	NPD7320	Approved
0.6449	Remote Similarity	NPD6899	Approved
0.6437	Remote Similarity	NPD6081	Approved
0.6436	Remote Similarity	NPD4697	Phase 3
0.6429	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD6650	Approved
0.6422	Remote Similarity	NPD6649	Approved
0.6413	Remote Similarity	NPD6928	Phase 2
0.6408	Remote Similarity	NPD7640	Approved
0.6408	Remote Similarity	NPD7639	Approved
0.6389	Remote Similarity	NPD6012	Approved
0.6389	Remote Similarity	NPD6013	Approved
0.6389	Remote Similarity	NPD6014	Approved
0.6386	Remote Similarity	NPD371	Approved
0.6383	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6383	Remote Similarity	NPD3669	Approved
0.6374	Remote Similarity	NPD3671	Phase 1
0.6373	Remote Similarity	NPD7902	Approved
0.6355	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6348	Remote Similarity	NPD6921	Approved
0.633	Remote Similarity	NPD7290	Approved
0.633	Remote Similarity	NPD6883	Approved
0.633	Remote Similarity	NPD7102	Approved
0.6322	Remote Similarity	NPD4789	Approved
0.631	Remote Similarity	NPD9496	Clinical (unspecified phase)
0.6306	Remote Similarity	NPD4632	Approved
0.6296	Remote Similarity	NPD6011	Approved
0.6286	Remote Similarity	NPD7632	Discontinued
0.6279	Remote Similarity	NPD5360	Phase 3
0.6279	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6847	Approved
0.6273	Remote Similarity	NPD6869	Approved
0.6273	Remote Similarity	NPD6617	Approved
0.6273	Remote Similarity	NPD8130	Phase 1
0.6271	Remote Similarity	NPD7507	Approved
0.6261	Remote Similarity	NPD6319	Approved
0.625	Remote Similarity	NPD7319	Approved
0.625	Remote Similarity	NPD8418	Phase 2
0.6238	Remote Similarity	NPD7748	Approved
0.6216	Remote Similarity	NPD6882	Approved
0.6216	Remote Similarity	NPD8297	Approved
0.6214	Remote Similarity	NPD4755	Approved
0.6207	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7515	Phase 2
0.6186	Remote Similarity	NPD3618	Phase 1
0.6186	Remote Similarity	NPD7492	Approved
0.6162	Remote Similarity	NPD5328	Approved
0.6161	Remote Similarity	NPD8133	Approved
0.6154	Remote Similarity	NPD4225	Approved
0.614	Remote Similarity	NPD6009	Approved
0.6136	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6616	Approved
0.6126	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD6054	Approved
0.6121	Remote Similarity	NPD6059	Approved
0.6102	Remote Similarity	NPD8328	Phase 3
0.6095	Remote Similarity	NPD4700	Approved
0.6095	Remote Similarity	NPD4696	Approved
0.6095	Remote Similarity	NPD5285	Approved
0.6095	Remote Similarity	NPD5286	Approved
0.6083	Remote Similarity	NPD8293	Discontinued
0.6083	Remote Similarity	NPD7078	Approved
0.6078	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6078	Remote Similarity	NPD7900	Approved
0.6076	Remote Similarity	NPD615	Clinical (unspecified phase)
0.6076	Remote Similarity	NPD3729	Clinical (unspecified phase)
0.6068	Remote Similarity	NPD5983	Phase 2
0.6068	Remote Similarity	NPD6016	Approved
0.6068	Remote Similarity	NPD6015	Approved
0.6067	Remote Similarity	NPD4758	Discontinued
0.6053	Remote Similarity	NPD6274	Approved
0.6053	Remote Similarity	NPD6940	Discontinued
0.604	Remote Similarity	NPD6079	Approved
0.604	Remote Similarity	NPD6411	Approved
0.6033	Remote Similarity	NPD7736	Approved
0.6022	Remote Similarity	NPD4238	Approved
0.6022	Remote Similarity	NPD4802	Phase 2
0.6017	Remote Similarity	NPD5988	Approved
0.6017	Remote Similarity	NPD6370	Approved
0.6	Remote Similarity	NPD7909	Approved
0.6	Remote Similarity	NPD6686	Approved
0.5981	Remote Similarity	NPD4633	Approved
0.5981	Remote Similarity	NPD5211	Phase 2
0.5981	Remote Similarity	NPD5224	Approved
0.5981	Remote Similarity	NPD5226	Approved
0.5981	Remote Similarity	NPD5225	Approved
0.598	Remote Similarity	NPD8171	Discontinued
0.598	Remote Similarity	NPD5779	Approved
0.598	Remote Similarity	NPD5778	Approved
0.5966	Remote Similarity	NPD7604	Phase 2
0.5962	Remote Similarity	NPD5221	Approved
0.5962	Remote Similarity	NPD5222	Approved
0.5962	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD3667	Approved
0.5934	Remote Similarity	NPD1811	Approved
0.5934	Remote Similarity	NPD1810	Approved
0.5932	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5926	Remote Similarity	NPD5174	Approved
0.5926	Remote Similarity	NPD5175	Approved
0.5918	Remote Similarity	NPD1694	Approved
0.5909	Remote Similarity	NPD6412	Phase 2
0.5905	Remote Similarity	NPD5173	Approved
0.5905	Remote Similarity	NPD6084	Phase 2
0.5905	Remote Similarity	NPD6083	Phase 2
0.5904	Remote Similarity	NPD3198	Approved
0.5897	Remote Similarity	NPD7101	Approved
0.5897	Remote Similarity	NPD7100	Approved
0.5893	Remote Similarity	NPD4634	Approved
0.5888	Remote Similarity	NPD5223	Approved
0.5872	Remote Similarity	NPD5141	Approved
0.5872	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.5872	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.5868	Remote Similarity	NPD6336	Discontinued
0.5865	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5862	Remote Similarity	NPD6317	Approved
0.5851	Remote Similarity	NPD5364	Discontinued
0.5849	Remote Similarity	NPD5696	Approved
0.5842	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD6101	Approved
0.5825	Remote Similarity	NPD4202	Approved
0.5818	Remote Similarity	NPD4768	Approved
0.5818	Remote Similarity	NPD4767	Approved
0.5816	Remote Similarity	NPD4786	Approved
0.5812	Remote Similarity	NPD6313	Approved
0.5812	Remote Similarity	NPD6335	Approved
0.5812	Remote Similarity	NPD6314	Approved
0.58	Remote Similarity	NPD3573	Approved
0.5798	Remote Similarity	NPD6908	Approved
0.5798	Remote Similarity	NPD6909	Approved
0.578	Remote Similarity	NPD4754	Approved
0.5776	Remote Similarity	NPD6868	Approved
0.5773	Remote Similarity	NPD6435	Approved
0.5728	Remote Similarity	NPD7637	Suspended
0.5726	Remote Similarity	NPD7115	Discovery
0.5714	Remote Similarity	NPD5128	Approved
0.5714	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4729	Approved
0.5714	Remote Similarity	NPD5695	Phase 3
0.5714	Remote Similarity	NPD4730	Approved
0.57	Remote Similarity	NPD6684	Approved
0.57	Remote Similarity	NPD6409	Approved
0.57	Remote Similarity	NPD5330	Approved
0.57	Remote Similarity	NPD7334	Approved
0.57	Remote Similarity	NPD7521	Approved
0.57	Remote Similarity	NPD7146	Approved
0.567	Remote Similarity	NPD1448	Clinical (unspecified phase)
0.5657	Remote Similarity	NPD3666	Approved
0.5657	Remote Similarity	NPD3133	Approved
0.5657	Remote Similarity	NPD3665	Phase 1
0.5652	Remote Similarity	NPD6053	Discontinued
0.5645	Remote Similarity	NPD6033	Approved
0.5619	Remote Similarity	NPD5282	Discontinued
0.5614	Remote Similarity	NPD5247	Approved
0.5614	Remote Similarity	NPD5249	Phase 3
0.5614	Remote Similarity	NPD5251	Approved
0.5614	Remote Similarity	NPD5248	Approved
0.5614	Remote Similarity	NPD5250	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