NPASS Compound

Structure

NPC156244 OpenBabel07101719242D 22 24 0 0 0 0 0 0 0 0999 V2000 -3.5491 1.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -3.4071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 0.0570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3090 -2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6831 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0878 -1.6750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 -0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3601 -3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5878 -0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 0.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5878 -2.5411 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 21 1 0 0 0 0 3 5 2 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 4 11 1 0 0 0 0 5 13 1 0 0 0 0 6 12 1 0 0 0 0 7 10 2 0 0 0 0 7 15 1 0 0 0 0 8 11 2 0 0 0 0 8 16 1 0 0 0 0 9 14 1 0 0 0 0 9 18 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 14 1 0 0 0 0 12 16 2 0 0 0 0 13 15 2 0 0 0 0 13 17 1 0 0 0 0 14 17 2 0 0 0 0 15 21 1 0 0 0 0 16 22 1 0 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	299.778
LogP:	3.474
LogD:	3.283
LogS:	-4.54
# Rotatable Bonds:	4
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.745
Synthetic Accessibility Score:	2.382
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.719
MDCK Permeability:	1.7647478671278805e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.042
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.146

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.058
Plasma Protein Binding (PPB):	95.29769134521484%
Volume Distribution (VD):	0.91
Pgp-substrate:	4.922812461853027%

ADMET: Metabolism

CYP1A2-inhibitor:	0.981
CYP1A2-substrate:	0.921
CYP2C19-inhibitor:	0.903
CYP2C19-substrate:	0.197
CYP2C9-inhibitor:	0.586
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.841
CYP2D6-substrate:	0.928
CYP3A4-inhibitor:	0.941
CYP3A4-substrate:	0.19

ADMET: Excretion

Clearance (CL):	9.77
Half-life (T1/2):	0.438

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.387
Drug-inuced Liver Injury (DILI):	0.952
AMES Toxicity:	0.769
Rat Oral Acute Toxicity:	0.034
Maximum Recommended Daily Dose:	0.876
Skin Sensitization:	0.224
Carcinogencity:	0.575
Eye Corrosion:	0.052
Eye Irritation:	0.909
Respiratory Toxicity:	0.666

Download Data

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

Natural Product: NPC156244

Natural Product ID:	NPC156244
*Common Name:**	Spinosan B
IUPAC Name:	2-(4-hydroxy-2-methoxyphenyl)-6-methoxy-1-benzofuran-3-carbaldehyde
Synonyms:
Standard InCHIKey:	HHCUPEXQXWEBHY-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-20-11-4-6-12-14(9-18)17(22-16(12)8-11)13-5-3-10(19)7-15(13)21-2/h3-9,19H,1-2H3
SMILES:	O=Cc1c(oc2c1ccc(c2)OC)c1ccc(cc1OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL480073
PubChem CID:	11709174
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO32589	dalea spinosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499327]

☑ 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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	140000.0	nM	PMID[575378]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	140000.0	nM	PMID[575378]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	140000.0	nM	PMID[575378]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	>	140000.0	nM	PMID[575378]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	140000.0	nM	PMID[575378]
NPT3006	Organism	Enterococcus faecalis V583	Enterococcus faecalis V583	MIC	>	140000.0	nM	PMID[575378]

☑ 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 NPC156244 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	404
0.1-0.2	1822
0.2-0.3	4248
0.3-0.4	10839
0.4-0.5	7346
0.5-0.6	4133
0.6-0.7	5919
0.7-0.8	4638
0.8-0.85	2078
0.85-0.9	1066
0.9-0.95	181
0.95-1	23

Similarity Score	Similarity Level	Natural Product ID
0.9931	High Similarity	NPC67654
0.973	High Similarity	NPC247677
0.973	High Similarity	NPC160015
0.9664	High Similarity	NPC296957
0.9664	High Similarity	NPC260902
0.96	High Similarity	NPC476349
0.96	High Similarity	NPC476350
0.9583	High Similarity	NPC230943
0.9514	High Similarity	NPC302181
0.9444	High Similarity	NPC53192
0.9396	High Similarity	NPC263676
0.9388	High Similarity	NPC135325
0.9342	High Similarity	NPC472877
0.9333	High Similarity	NPC122365
0.9333	High Similarity	NPC213608
0.9333	High Similarity	NPC1477
0.9329	High Similarity	NPC116604
0.9329	High Similarity	NPC115324
0.9324	High Similarity	NPC296030
0.9324	High Similarity	NPC37226
0.9324	High Similarity	NPC39929
0.9324	High Similarity	NPC226644
0.932	High Similarity	NPC130581
0.932	High Similarity	NPC12148
0.932	High Similarity	NPC17816
0.9267	High Similarity	NPC5871
0.9267	High Similarity	NPC207624
0.9252	High Similarity	NPC210826
0.9252	High Similarity	NPC300267
0.9252	High Similarity	NPC51641
0.9247	High Similarity	NPC225884
0.92	High Similarity	NPC193976
0.92	High Similarity	NPC58668
0.92	High Similarity	NPC106372
0.92	High Similarity	NPC170169
0.92	High Similarity	NPC23668
0.9184	High Similarity	NPC98926
0.9184	High Similarity	NPC155144
0.9167	High Similarity	NPC291110
0.9156	High Similarity	NPC260296
0.9156	High Similarity	NPC115432
0.915	High Similarity	NPC65504
0.9145	High Similarity	NPC474542
0.9145	High Similarity	NPC198490
0.9145	High Similarity	NPC148938
0.9139	High Similarity	NPC142308
0.9139	High Similarity	NPC253872
0.9139	High Similarity	NPC41326
0.9133	High Similarity	NPC167576
0.9133	High Similarity	NPC230713
0.9133	High Similarity	NPC78335
0.9097	High Similarity	NPC304387
0.9091	High Similarity	NPC244750
0.9091	High Similarity	NPC40583
0.9079	High Similarity	NPC42458
0.9079	High Similarity	NPC158261
0.9079	High Similarity	NPC183874
0.9079	High Similarity	NPC235333
0.9067	High Similarity	NPC37208
0.9067	High Similarity	NPC178202
0.9067	High Similarity	NPC221868
0.906	High Similarity	NPC198427
0.9054	High Similarity	NPC184649
0.9054	High Similarity	NPC303185
0.9048	High Similarity	NPC202981
0.9045	High Similarity	NPC136641
0.9038	High Similarity	NPC193998
0.9034	High Similarity	NPC124269
0.9026	High Similarity	NPC96342
0.9026	High Similarity	NPC270044
0.9026	High Similarity	NPC164110
0.9026	High Similarity	NPC212967
0.9026	High Similarity	NPC246647
0.902	High Similarity	NPC213936
0.902	High Similarity	NPC99199
0.902	High Similarity	NPC297531
0.9007	High Similarity	NPC148423
0.9007	High Similarity	NPC135303
0.9007	High Similarity	NPC472406
0.9	High Similarity	NPC272194
0.8993	High Similarity	NPC299011
0.8986	High Similarity	NPC113770
0.8981	High Similarity	NPC38591
0.8981	High Similarity	NPC155640
0.8966	High Similarity	NPC188879
0.8961	High Similarity	NPC13879
0.8961	High Similarity	NPC180924
0.8954	High Similarity	NPC72370
0.8954	High Similarity	NPC472462
0.894	High Similarity	NPC317492
0.8931	High Similarity	NPC320789
0.8926	High Similarity	NPC311144
0.8904	High Similarity	NPC280284
0.8904	High Similarity	NPC309154
0.8904	High Similarity	NPC99333
0.8904	High Similarity	NPC12175
0.8904	High Similarity	NPC55162
0.8904	High Similarity	NPC90665
0.8904	High Similarity	NPC278323
0.8904	High Similarity	NPC279668
0.8904	High Similarity	NPC188947
0.8903	High Similarity	NPC269495
0.8903	High Similarity	NPC268360
0.8897	High Similarity	NPC240593
0.8889	High Similarity	NPC130015
0.8889	High Similarity	NPC38361
0.8889	High Similarity	NPC236327
0.8889	High Similarity	NPC290304
0.8882	High Similarity	NPC155882
0.8874	High Similarity	NPC168085
0.8874	High Similarity	NPC39195
0.8874	High Similarity	NPC306788
0.8867	High Similarity	NPC190572
0.8861	High Similarity	NPC109180
0.8854	High Similarity	NPC188486
0.8851	High Similarity	NPC3188
0.8844	High Similarity	NPC274784
0.8844	High Similarity	NPC316480
0.8844	High Similarity	NPC329203
0.8844	High Similarity	NPC310135
0.8844	High Similarity	NPC150648
0.8844	High Similarity	NPC261234
0.8844	High Similarity	NPC225153
0.8844	High Similarity	NPC222342
0.8844	High Similarity	NPC265871
0.8844	High Similarity	NPC20709
0.8839	High Similarity	NPC137100
0.8839	High Similarity	NPC45131
0.8836	High Similarity	NPC275055
0.8836	High Similarity	NPC250266
0.8836	High Similarity	NPC181124
0.8836	High Similarity	NPC209560
0.8836	High Similarity	NPC7013
0.8836	High Similarity	NPC116632
0.8836	High Similarity	NPC294409
0.8836	High Similarity	NPC228661
0.8836	High Similarity	NPC303644
0.8836	High Similarity	NPC266597
0.8836	High Similarity	NPC290291
0.8836	High Similarity	NPC162680
0.8831	High Similarity	NPC41719
0.8824	High Similarity	NPC472407
0.882	High Similarity	NPC120220
0.882	High Similarity	NPC131866
0.8816	High Similarity	NPC88445
0.8808	High Similarity	NPC308200
0.8805	High Similarity	NPC38914
0.88	High Similarity	NPC311741
0.88	High Similarity	NPC271288
0.88	High Similarity	NPC234629
0.8797	High Similarity	NPC84515
0.8797	High Similarity	NPC219861
0.8797	High Similarity	NPC312056
0.8792	High Similarity	NPC96791
0.8792	High Similarity	NPC470636
0.8792	High Similarity	NPC226942
0.879	High Similarity	NPC304839
0.879	High Similarity	NPC220582
0.879	High Similarity	NPC169
0.8784	High Similarity	NPC6407
0.8784	High Similarity	NPC76445
0.8784	High Similarity	NPC110228
0.8784	High Similarity	NPC129853
0.8784	High Similarity	NPC284550
0.8784	High Similarity	NPC188243
0.8784	High Similarity	NPC28337
0.8784	High Similarity	NPC101366
0.8776	High Similarity	NPC118813
0.8776	High Similarity	NPC147686
0.8776	High Similarity	NPC471620
0.8776	High Similarity	NPC329225
0.8776	High Similarity	NPC472460
0.8774	High Similarity	NPC233776
0.8767	High Similarity	NPC47815
0.8767	High Similarity	NPC213603
0.8767	High Similarity	NPC127447
0.8767	High Similarity	NPC231772
0.8767	High Similarity	NPC235428
0.8767	High Similarity	NPC29353
0.8767	High Similarity	NPC234133
0.8767	High Similarity	NPC194281
0.8767	High Similarity	NPC87545
0.8767	High Similarity	NPC473887
0.8767	High Similarity	NPC124784
0.8765	High Similarity	NPC472584
0.8759	High Similarity	NPC286336
0.8758	High Similarity	NPC191104
0.8758	High Similarity	NPC472421
0.8758	High Similarity	NPC321896
0.8758	High Similarity	NPC53252
0.8758	High Similarity	NPC476185
0.8758	High Similarity	NPC267117
0.875	High Similarity	NPC145467
0.875	High Similarity	NPC212631
0.875	High Similarity	NPC257756
0.875	High Similarity	NPC129132
0.875	High Similarity	NPC277480
0.875	High Similarity	NPC53640
0.875	High Similarity	NPC266572
0.875	High Similarity	NPC205468

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 NPC156244 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	374
0.1-0.2	993
0.2-0.3	1577
0.3-0.4	2665
0.4-0.5	1901
0.5-0.6	1126
0.6-0.7	340
0.7-0.8	115
0.8-0.85	40
0.85-0.9	16
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD2344	Approved
0.8851	High Similarity	NPD2309	Approved
0.8782	High Similarity	NPD3749	Approved
0.8776	High Similarity	NPD1549	Phase 2
0.8707	High Similarity	NPD1550	Clinical (unspecified phase)
0.8707	High Similarity	NPD1552	Clinical (unspecified phase)
0.8699	High Similarity	NPD1510	Phase 2
0.8684	High Similarity	NPD920	Approved
0.8681	High Similarity	NPD1240	Approved
0.8562	High Similarity	NPD1607	Approved
0.8553	High Similarity	NPD642	Clinical (unspecified phase)
0.8553	High Similarity	NPD4378	Clinical (unspecified phase)
0.8543	High Similarity	NPD643	Clinical (unspecified phase)
0.8514	High Similarity	NPD2796	Approved
0.8481	Intermediate Similarity	NPD3882	Suspended
0.8467	Intermediate Similarity	NPD2800	Approved
0.8431	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8418	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD3926	Phase 2
0.8389	Intermediate Similarity	NPD1551	Phase 2
0.8344	Intermediate Similarity	NPD7411	Suspended
0.8344	Intermediate Similarity	NPD1243	Approved
0.8291	Intermediate Similarity	NPD1934	Approved
0.8263	Intermediate Similarity	NPD6559	Discontinued
0.825	Intermediate Similarity	NPD7768	Phase 2
0.8247	Intermediate Similarity	NPD6799	Approved
0.8239	Intermediate Similarity	NPD7819	Suspended
0.8239	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8232	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8212	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7075	Discontinued
0.8187	Intermediate Similarity	NPD2296	Approved
0.817	Intermediate Similarity	NPD3750	Approved
0.8165	Intermediate Similarity	NPD6599	Discontinued
0.8165	Intermediate Similarity	NPD4380	Phase 2
0.816	Intermediate Similarity	NPD1247	Approved
0.8148	Intermediate Similarity	NPD919	Approved
0.8129	Intermediate Similarity	NPD1511	Approved
0.8125	Intermediate Similarity	NPD2801	Approved
0.8125	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8086	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6959	Discontinued
0.8039	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8025	Intermediate Similarity	NPD1512	Approved
0.8024	Intermediate Similarity	NPD3818	Discontinued
0.7988	Intermediate Similarity	NPD5494	Approved
0.7987	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD2533	Approved
0.7962	Intermediate Similarity	NPD2532	Approved
0.7962	Intermediate Similarity	NPD2534	Approved
0.795	Intermediate Similarity	NPD6279	Approved
0.795	Intermediate Similarity	NPD6801	Discontinued
0.795	Intermediate Similarity	NPD6280	Approved
0.7919	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD6166	Phase 2
0.7892	Intermediate Similarity	NPD6232	Discontinued
0.7882	Intermediate Similarity	NPD5953	Discontinued
0.7857	Intermediate Similarity	NPD1471	Phase 3
0.7857	Intermediate Similarity	NPD7473	Discontinued
0.7843	Intermediate Similarity	NPD2799	Discontinued
0.7843	Intermediate Similarity	NPD3748	Approved
0.7811	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD6808	Phase 2
0.7744	Intermediate Similarity	NPD3817	Phase 2
0.7727	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4287	Approved
0.7712	Intermediate Similarity	NPD6651	Approved
0.7707	Intermediate Similarity	NPD4628	Phase 3
0.7703	Intermediate Similarity	NPD1203	Approved
0.7697	Intermediate Similarity	NPD943	Approved
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7667	Intermediate Similarity	NPD4908	Phase 1
0.7661	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7286	Phase 2
0.7654	Intermediate Similarity	NPD3226	Approved
0.764	Intermediate Similarity	NPD5403	Approved
0.7625	Intermediate Similarity	NPD5401	Approved
0.7616	Intermediate Similarity	NPD7074	Phase 3
0.7566	Intermediate Similarity	NPD2313	Discontinued
0.7566	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD3764	Approved
0.7558	Intermediate Similarity	NPD7054	Approved
0.7558	Intermediate Similarity	NPD5844	Phase 1
0.7551	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1610	Phase 2
0.755	Intermediate Similarity	NPD6832	Phase 2
0.753	Intermediate Similarity	NPD5402	Approved
0.7514	Intermediate Similarity	NPD8434	Phase 2
0.7514	Intermediate Similarity	NPD7472	Approved
0.75	Intermediate Similarity	NPD9717	Approved
0.7471	Intermediate Similarity	NPD6797	Phase 2
0.747	Intermediate Similarity	NPD5760	Phase 2
0.747	Intermediate Similarity	NPD5761	Phase 2
0.747	Intermediate Similarity	NPD1465	Phase 2
0.7452	Intermediate Similarity	NPD6099	Approved
0.7452	Intermediate Similarity	NPD6100	Approved
0.7429	Intermediate Similarity	NPD7251	Discontinued
0.7423	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2654	Approved
0.7417	Intermediate Similarity	NPD2798	Approved
0.7414	Intermediate Similarity	NPD1729	Discontinued
0.7407	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD2346	Discontinued
0.74	Intermediate Similarity	NPD1876	Approved
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7389	Intermediate Similarity	NPD7033	Discontinued
0.7386	Intermediate Similarity	NPD7808	Phase 3
0.7386	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD3972	Approved
0.7371	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5711	Approved
0.7368	Intermediate Similarity	NPD7229	Phase 3
0.7368	Intermediate Similarity	NPD5710	Approved
0.7346	Intermediate Similarity	NPD7390	Discontinued
0.7338	Intermediate Similarity	NPD3268	Approved
0.7322	Intermediate Similarity	NPD4361	Phase 2
0.7322	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7308	Intermediate Similarity	NPD230	Phase 1
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD3751	Discontinued
0.7283	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD9545	Approved
0.7278	Intermediate Similarity	NPD4308	Phase 3
0.7267	Intermediate Similarity	NPD1608	Approved
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD3269	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD1470	Approved
0.7237	Intermediate Similarity	NPD2797	Approved
0.7232	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4288	Approved
0.7209	Intermediate Similarity	NPD7199	Phase 2
0.7197	Intermediate Similarity	NPD447	Suspended
0.7184	Intermediate Similarity	NPD2403	Approved
0.7174	Intermediate Similarity	NPD4363	Phase 3
0.7174	Intermediate Similarity	NPD4360	Phase 2
0.7172	Intermediate Similarity	NPD1241	Discontinued
0.717	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD9493	Approved
0.7134	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1164	Approved
0.7124	Intermediate Similarity	NPD3266	Approved
0.7124	Intermediate Similarity	NPD3267	Approved
0.7115	Intermediate Similarity	NPD411	Approved
0.7097	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7089	Intermediate Similarity	NPD1933	Approved
0.7078	Intermediate Similarity	NPD1019	Discontinued
0.7074	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD17	Approved
0.7065	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3225	Approved
0.7055	Intermediate Similarity	NPD7003	Approved
0.7051	Intermediate Similarity	NPD4625	Phase 3
0.7041	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD6104	Discontinued
0.7025	Intermediate Similarity	NPD4307	Phase 2
0.7025	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD1613	Approved
0.7024	Intermediate Similarity	NPD7458	Discontinued
0.7019	Intermediate Similarity	NPD5405	Approved
0.7019	Intermediate Similarity	NPD5404	Approved
0.7019	Intermediate Similarity	NPD5406	Approved
0.7019	Intermediate Similarity	NPD5408	Approved
0.7018	Intermediate Similarity	NPD5616	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD1296	Phase 2
0.7006	Intermediate Similarity	NPD6798	Discontinued
0.6987	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD1201	Approved
0.6971	Remote Similarity	NPD3787	Discontinued
0.6971	Remote Similarity	NPD5668	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD8312	Approved
0.6961	Remote Similarity	NPD8313	Approved
0.6957	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6936	Remote Similarity	NPD6971	Discontinued
0.6923	Remote Similarity	NPD2861	Phase 2
0.6923	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD405	Clinical (unspecified phase)
0.691	Remote Similarity	NPD7177	Discontinued
0.6909	Remote Similarity	NPD2354	Approved
0.6901	Remote Similarity	NPD7577	Discontinued
0.6901	Remote Similarity	NPD6844	Discontinued
0.6901	Remote Similarity	NPD37	Approved
0.6897	Remote Similarity	NPD6234	Discontinued
0.6886	Remote Similarity	NPD4661	Approved
0.6886	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD4662	Approved
0.6883	Remote Similarity	NPD4749	Approved
0.6879	Remote Similarity	NPD4967	Phase 2
0.6879	Remote Similarity	NPD4966	Approved
0.6879	Remote Similarity	NPD4965	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