NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	222.05
Volume:	212.468
LogP:	1.047
LogD:	1.208
LogS:	-2.32
# Rotatable Bonds:	2
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.78
Synthetic Accessibility Score:	2.233
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.807
MDCK Permeability:	2.6134799554711208e-05
Pgp-inhibitor:	0.011
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.855

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.199
Plasma Protein Binding (PPB):	77.70203399658203%
Volume Distribution (VD):	0.893
Pgp-substrate:	20.335094451904297%

ADMET: Metabolism

CYP1A2-inhibitor:	0.951
CYP1A2-substrate:	0.968
CYP2C19-inhibitor:	0.088
CYP2C19-substrate:	0.427
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.449
CYP2D6-substrate:	0.853
CYP3A4-inhibitor:	0.141
CYP3A4-substrate:	0.335

ADMET: Excretion

Clearance (CL):	12.588
Half-life (T1/2):	0.855

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.724
Drug-inuced Liver Injury (DILI):	0.947
AMES Toxicity:	0.122
Rat Oral Acute Toxicity:	0.452
Maximum Recommended Daily Dose:	0.113
Skin Sensitization:	0.414
Carcinogencity:	0.635
Eye Corrosion:	0.03
Eye Irritation:	0.479
Respiratory Toxicity:	0.368

Download Data

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

Natural Product: NPC82271

Natural Product ID:	NPC82271
*Common Name:**	Leptodactylone
IUPAC Name:	8-hydroxy-5,7-dimethoxychromen-2-one
Synonyms:	leptodactylone
Standard InCHIKey:	TUFLVKBJDSZLAW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10O5/c1-14-7-5-8(15-2)10(13)11-6(7)3-4-9(12)16-11/h3-5,13H,1-2H3
SMILES:	COc1cc(c(c2c1ccc(=O)o2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL595334
PubChem CID:	442134
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins

*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
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14650	Lobelia chinensis	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14650	Lobelia chinensis	Species	Campanulaceae	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
IC50	1
Others	1

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	CC50	>	2000000.0	nM	PMID[467968]
NPT466	Cell Line	U-937	Homo sapiens	IC50	>	400000.0	nM	PMID[467968]

☑ 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 NPC82271 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	420
0.1-0.2	2082
0.2-0.3	5906
0.3-0.4	11104
0.4-0.5	5604
0.5-0.6	4174
0.6-0.7	5331
0.7-0.8	5233
0.8-0.85	1826
0.85-0.9	812
0.9-0.95	193
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC126682
0.9923	High Similarity	NPC76336
0.9923	High Similarity	NPC148835
0.9923	High Similarity	NPC95162
0.9923	High Similarity	NPC20511
0.9923	High Similarity	NPC139548
0.9923	High Similarity	NPC52086
0.9847	High Similarity	NPC13067
0.9767	High Similarity	NPC26673
0.9692	High Similarity	NPC92830
0.9538	High Similarity	NPC137949
0.9466	High Similarity	NPC277021
0.9462	High Similarity	NPC73738
0.9457	High Similarity	NPC27239
0.9457	High Similarity	NPC123127
0.9412	High Similarity	NPC7439
0.9412	High Similarity	NPC236419
0.9412	High Similarity	NPC34245
0.9412	High Similarity	NPC230157
0.9412	High Similarity	NPC110067
0.9412	High Similarity	NPC256555
0.9412	High Similarity	NPC91492
0.9403	High Similarity	NPC164148
0.9403	High Similarity	NPC43500
0.9385	High Similarity	NPC240722
0.9385	High Similarity	NPC244799
0.9281	High Similarity	NPC231149
0.9265	High Similarity	NPC300611
0.9242	High Similarity	NPC137669
0.9214	High Similarity	NPC139839
0.9185	High Similarity	NPC38874
0.9173	High Similarity	NPC241341
0.9173	High Similarity	NPC36437
0.9173	High Similarity	NPC233018
0.9149	High Similarity	NPC30688
0.9149	High Similarity	NPC176903
0.913	High Similarity	NPC138212
0.9104	High Similarity	NPC111635
0.9104	High Similarity	NPC309953
0.9085	High Similarity	NPC120426
0.9085	High Similarity	NPC205727
0.9085	High Similarity	NPC21184
0.9085	High Similarity	NPC294522
0.9078	High Similarity	NPC48366
0.9065	High Similarity	NPC185127
0.9065	High Similarity	NPC471763
0.9044	High Similarity	NPC474886
0.9037	High Similarity	NPC240915
0.9037	High Similarity	NPC472521
0.903	High Similarity	NPC474810
0.9021	High Similarity	NPC213197
0.9014	High Similarity	NPC212670
0.9014	High Similarity	NPC313334
0.9014	High Similarity	NPC206264
0.9007	High Similarity	NPC476347
0.9007	High Similarity	NPC178129
0.9	High Similarity	NPC58279
0.9	High Similarity	NPC300326
0.9	High Similarity	NPC476450
0.8993	High Similarity	NPC6568
0.8971	High Similarity	NPC167517
0.8958	High Similarity	NPC163598
0.8958	High Similarity	NPC264875
0.8958	High Similarity	NPC120774
0.8955	High Similarity	NPC319969
0.8955	High Similarity	NPC245120
0.8947	High Similarity	NPC19242
0.8944	High Similarity	NPC187398
0.8944	High Similarity	NPC476348
0.8939	High Similarity	NPC109275
0.8936	High Similarity	NPC205361
0.8921	High Similarity	NPC469564
0.8905	High Similarity	NPC20796
0.8897	High Similarity	NPC234865
0.8881	High Similarity	NPC147317
0.8881	High Similarity	NPC142530
0.8873	High Similarity	NPC15577
0.8873	High Similarity	NPC41844
0.8872	High Similarity	NPC48315
0.8872	High Similarity	NPC45824
0.8849	High Similarity	NPC279851
0.8849	High Similarity	NPC472520
0.8841	High Similarity	NPC270256
0.8832	High Similarity	NPC286843
0.8832	High Similarity	NPC309031
0.8824	High Similarity	NPC7163
0.8815	High Similarity	NPC474635
0.8811	High Similarity	NPC96294
0.8806	High Similarity	NPC214860
0.8779	High Similarity	NPC183446
0.8768	High Similarity	NPC105493
0.8768	High Similarity	NPC476171
0.8768	High Similarity	NPC276328
0.8759	High Similarity	NPC73071
0.8759	High Similarity	NPC252095
0.875	High Similarity	NPC472522
0.8722	High Similarity	NPC216836
0.8702	High Similarity	NPC238810
0.8692	High Similarity	NPC310373
0.869	High Similarity	NPC114740
0.8686	High Similarity	NPC147030
0.8686	High Similarity	NPC106215
0.8686	High Similarity	NPC474600
0.8676	High Similarity	NPC123954
0.8676	High Similarity	NPC5423
0.8657	High Similarity	NPC474616
0.8623	High Similarity	NPC472337
0.8615	High Similarity	NPC307253
0.8615	High Similarity	NPC302107
0.8613	High Similarity	NPC229442
0.8613	High Similarity	NPC168059
0.8611	High Similarity	NPC275125
0.8611	High Similarity	NPC97937
0.8611	High Similarity	NPC170239
0.8603	High Similarity	NPC82503
0.8593	High Similarity	NPC10225
0.8593	High Similarity	NPC58164
0.8582	High Similarity	NPC194841
0.8582	High Similarity	NPC474670
0.8571	High Similarity	NPC271985
0.8571	High Similarity	NPC27352
0.8561	High Similarity	NPC26954
0.8561	High Similarity	NPC472336
0.8561	High Similarity	NPC38099
0.8561	High Similarity	NPC472334
0.8552	High Similarity	NPC478237
0.8551	High Similarity	NPC50896
0.8551	High Similarity	NPC326600
0.8551	High Similarity	NPC204353
0.855	High Similarity	NPC285289
0.855	High Similarity	NPC52247
0.855	High Similarity	NPC187868
0.8542	High Similarity	NPC40222
0.8542	High Similarity	NPC287275
0.8542	High Similarity	NPC268515
0.854	High Similarity	NPC194277
0.854	High Similarity	NPC86655
0.854	High Similarity	NPC161203
0.854	High Similarity	NPC202762
0.8538	High Similarity	NPC2058
0.8538	High Similarity	NPC247553
0.8529	High Similarity	NPC234488
0.8529	High Similarity	NPC299221
0.8529	High Similarity	NPC311680
0.8529	High Similarity	NPC51840
0.8529	High Similarity	NPC220935
0.8529	High Similarity	NPC91291
0.8521	High Similarity	NPC472332
0.8521	High Similarity	NPC472335
0.8519	High Similarity	NPC474623
0.8519	High Similarity	NPC19694
0.8519	High Similarity	NPC474651
0.8514	High Similarity	NPC150442
0.8511	High Similarity	NPC267291
0.8507	High Similarity	NPC476006
0.8507	High Similarity	NPC127604
0.85	High Similarity	NPC126206
0.85	High Similarity	NPC107551
0.85	High Similarity	NPC294456
0.85	High Similarity	NPC102904
0.85	High Similarity	NPC176051
0.85	High Similarity	NPC212124
0.85	High Similarity	NPC225106
0.85	High Similarity	NPC474282
0.85	High Similarity	NPC184861
0.85	High Similarity	NPC103976
0.85	High Similarity	NPC276490
0.85	High Similarity	NPC281014
0.85	High Similarity	NPC326797
0.8493	Intermediate Similarity	NPC113790
0.8493	Intermediate Similarity	NPC107636
0.8489	Intermediate Similarity	NPC33986
0.8489	Intermediate Similarity	NPC472525
0.8485	Intermediate Similarity	NPC194626
0.8483	Intermediate Similarity	NPC52740
0.8478	Intermediate Similarity	NPC36490
0.8478	Intermediate Similarity	NPC163557
0.8478	Intermediate Similarity	NPC36661
0.8478	Intermediate Similarity	NPC37196
0.8478	Intermediate Similarity	NPC94236
0.8472	Intermediate Similarity	NPC125617
0.8467	Intermediate Similarity	NPC29734
0.8462	Intermediate Similarity	NPC298796
0.8456	Intermediate Similarity	NPC8712
0.8451	Intermediate Similarity	NPC224876
0.8451	Intermediate Similarity	NPC83375
0.8446	Intermediate Similarity	NPC53587
0.8446	Intermediate Similarity	NPC176186
0.8446	Intermediate Similarity	NPC169404
0.8444	Intermediate Similarity	NPC224774
0.8444	Intermediate Similarity	NPC121740
0.8444	Intermediate Similarity	NPC210355
0.8444	Intermediate Similarity	NPC474821
0.8444	Intermediate Similarity	NPC258567
0.844	Intermediate Similarity	NPC151946
0.844	Intermediate Similarity	NPC25966
0.844	Intermediate Similarity	NPC245207
0.844	Intermediate Similarity	NPC127218
0.844	Intermediate Similarity	NPC319647
0.8433	Intermediate Similarity	NPC265483

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 NPC82271 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	401
0.1-0.2	1046
0.2-0.3	2205
0.3-0.4	2581
0.4-0.5	1594
0.5-0.6	868
0.6-0.7	320
0.7-0.8	101
0.8-0.85	20
0.85-0.9	13
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9014	High Similarity	NPD1653	Approved
0.855	High Similarity	NPD422	Phase 1
0.8382	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD1613	Approved
0.8212	Intermediate Similarity	NPD2801	Approved
0.8058	Intermediate Similarity	NPD3027	Phase 3
0.7974	Intermediate Similarity	NPD1465	Phase 2
0.7973	Intermediate Similarity	NPD1511	Approved
0.7958	Intermediate Similarity	NPD447	Suspended
0.7958	Intermediate Similarity	NPD230	Phase 1
0.7945	Intermediate Similarity	NPD1652	Phase 2
0.7908	Intermediate Similarity	NPD1934	Approved
0.7871	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7867	Intermediate Similarity	NPD1512	Approved
0.7806	Intermediate Similarity	NPD3817	Phase 2
0.7756	Intermediate Similarity	NPD3882	Suspended
0.7754	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5844	Phase 1
0.771	Intermediate Similarity	NPD228	Approved
0.7704	Intermediate Similarity	NPD1548	Phase 1
0.7664	Intermediate Similarity	NPD3496	Discontinued
0.7636	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD7549	Discontinued
0.7635	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7606	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD5124	Phase 1
0.7546	Intermediate Similarity	NPD3818	Discontinued
0.7535	Intermediate Similarity	NPD3018	Phase 2
0.7533	Intermediate Similarity	NPD3750	Approved
0.75	Intermediate Similarity	NPD7054	Approved
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD1610	Phase 2
0.7468	Intermediate Similarity	NPD5402	Approved
0.7455	Intermediate Similarity	NPD7472	Approved
0.745	Intermediate Similarity	NPD7266	Discontinued
0.7447	Intermediate Similarity	NPD3225	Approved
0.7438	Intermediate Similarity	NPD919	Approved
0.7423	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6166	Phase 2
0.7417	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD4060	Phase 1
0.7386	Intermediate Similarity	NPD6799	Approved
0.7385	Intermediate Similarity	NPD9697	Approved
0.7383	Intermediate Similarity	NPD2935	Discontinued
0.7379	Intermediate Similarity	NPD1296	Phase 2
0.7376	Intermediate Similarity	NPD2982	Phase 2
0.7376	Intermediate Similarity	NPD2983	Phase 2
0.7368	Intermediate Similarity	NPD6190	Approved
0.7361	Intermediate Similarity	NPD4908	Phase 1
0.7357	Intermediate Similarity	NPD1091	Approved
0.7349	Intermediate Similarity	NPD7074	Phase 3
0.7329	Intermediate Similarity	NPD6234	Discontinued
0.7305	Intermediate Similarity	NPD6797	Phase 2
0.7305	Intermediate Similarity	NPD2981	Phase 2
0.7305	Intermediate Similarity	NPD9717	Approved
0.7305	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD9269	Phase 2
0.7301	Intermediate Similarity	NPD6232	Discontinued
0.7292	Intermediate Similarity	NPD9494	Approved
0.7279	Intermediate Similarity	NPD1558	Phase 1
0.7273	Intermediate Similarity	NPD1358	Approved
0.7273	Intermediate Similarity	NPD1203	Approved
0.7273	Intermediate Similarity	NPD4357	Discontinued
0.7267	Intermediate Similarity	NPD7075	Discontinued
0.7262	Intermediate Similarity	NPD7251	Discontinued
0.726	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4749	Approved
0.7246	Intermediate Similarity	NPD5536	Phase 2
0.7239	Intermediate Similarity	NPD7199	Phase 2
0.7239	Intermediate Similarity	NPD1247	Approved
0.7233	Intermediate Similarity	NPD6801	Discontinued
0.7226	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6671	Approved
0.7219	Intermediate Similarity	NPD7808	Phase 3
0.7214	Intermediate Similarity	NPD1778	Approved
0.72	Intermediate Similarity	NPD1510	Phase 2
0.72	Intermediate Similarity	NPD3748	Approved
0.719	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD5494	Approved
0.7172	Intermediate Similarity	NPD2861	Phase 2
0.7171	Intermediate Similarity	NPD1549	Phase 2
0.7169	Intermediate Similarity	NPD7473	Discontinued
0.7162	Intermediate Similarity	NPD1240	Approved
0.7161	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2797	Approved
0.7152	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD290	Approved
0.7143	Intermediate Similarity	NPD411	Approved
0.7134	Intermediate Similarity	NPD920	Approved
0.7134	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD5403	Approved
0.7125	Intermediate Similarity	NPD37	Approved
0.7115	Intermediate Similarity	NPD5401	Approved
0.7114	Intermediate Similarity	NPD4340	Discontinued
0.7114	Intermediate Similarity	NPD1933	Approved
0.7113	Intermediate Similarity	NPD1611	Approved
0.7113	Intermediate Similarity	NPD1535	Discovery
0.7107	Intermediate Similarity	NPD4380	Phase 2
0.7107	Intermediate Similarity	NPD6599	Discontinued
0.7105	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD4966	Approved
0.7099	Intermediate Similarity	NPD4967	Phase 2
0.7099	Intermediate Similarity	NPD4965	Approved
0.7095	Intermediate Similarity	NPD6233	Phase 2
0.7092	Intermediate Similarity	NPD4626	Approved
0.7089	Intermediate Similarity	NPD3687	Approved
0.7089	Intermediate Similarity	NPD3686	Approved
0.7081	Intermediate Similarity	NPD7819	Suspended
0.7078	Intermediate Similarity	NPD4628	Phase 3
0.7075	Intermediate Similarity	NPD4625	Phase 3
0.707	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7068	Intermediate Similarity	NPD968	Approved
0.7067	Intermediate Similarity	NPD1607	Approved
0.7063	Intermediate Similarity	NPD1481	Phase 2
0.7047	Intermediate Similarity	NPD943	Approved
0.7032	Intermediate Similarity	NPD2219	Phase 1
0.7027	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD3268	Approved
0.7024	Intermediate Similarity	NPD7228	Approved
0.7021	Intermediate Similarity	NPD9268	Approved
0.7013	Intermediate Similarity	NPD1243	Approved
0.7	Intermediate Similarity	NPD4675	Approved
0.7	Intermediate Similarity	NPD4678	Approved
0.7	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.6994	Remote Similarity	NPD7768	Phase 2
0.6993	Remote Similarity	NPD3540	Phase 1
0.6993	Remote Similarity	NPD3705	Approved
0.6974	Remote Similarity	NPD4308	Phase 3
0.697	Remote Similarity	NPD5677	Discontinued
0.6959	Remote Similarity	NPD6559	Discontinued
0.6959	Remote Similarity	NPD7095	Approved
0.6957	Remote Similarity	NPD7411	Suspended
0.6957	Remote Similarity	NPD5283	Phase 1
0.695	Remote Similarity	NPD9545	Approved
0.6944	Remote Similarity	NPD1608	Approved
0.694	Remote Similarity	NPD3134	Approved
0.6933	Remote Similarity	NPD5353	Approved
0.6928	Remote Similarity	NPD3539	Phase 1
0.6928	Remote Similarity	NPD8127	Discontinued
0.6928	Remote Similarity	NPD2796	Approved
0.6913	Remote Similarity	NPD6798	Discontinued
0.6903	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1357	Approved
0.6901	Remote Similarity	NPD5691	Approved
0.6899	Remote Similarity	NPD2532	Approved
0.6899	Remote Similarity	NPD2534	Approved
0.6899	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD2533	Approved
0.6897	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6355	Discontinued
0.6884	Remote Similarity	NPD5535	Approved
0.6883	Remote Similarity	NPD5762	Approved
0.6883	Remote Similarity	NPD5763	Approved
0.6879	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD1019	Discontinued
0.6863	Remote Similarity	NPD651	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7685	Pre-registration
0.6859	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD4110	Phase 3
0.6852	Remote Similarity	NPD5090	Approved
0.6852	Remote Similarity	NPD5089	Approved
0.6849	Remote Similarity	NPD6696	Suspended
0.6848	Remote Similarity	NPD3749	Approved
0.6842	Remote Similarity	NPD6653	Approved
0.6839	Remote Similarity	NPD2424	Discontinued
0.6838	Remote Similarity	NPD2684	Approved
0.6835	Remote Similarity	NPD5297	Approved
0.6832	Remote Similarity	NPD3111	Phase 1
0.6824	Remote Similarity	NPD3751	Discontinued
0.6818	Remote Similarity	NPD1242	Phase 1
0.6818	Remote Similarity	NPD6099	Approved
0.6818	Remote Similarity	NPD6100	Approved
0.6809	Remote Similarity	NPD9493	Approved
0.6803	Remote Similarity	NPD3267	Approved
0.6803	Remote Similarity	NPD3266	Approved
0.68	Remote Similarity	NPD1048	Approved
0.68	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD2800	Approved
0.6795	Remote Similarity	NPD6674	Discontinued
0.6784	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD6832	Phase 2
0.6774	Remote Similarity	NPD1375	Discontinued
0.6767	Remote Similarity	NPD291	Approved
0.6767	Remote Similarity	NPD846	Approved
0.6767	Remote Similarity	NPD940	Approved
0.6763	Remote Similarity	NPD7843	Approved
0.6757	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD7033	Discontinued

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