NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	206.06
Volume:	203.678
LogP:	1.659
LogD:	1.56
LogS:	-2.109
# Rotatable Bonds:	1
TPSA:	59.67
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.723
Synthetic Accessibility Score:	2.238
Fsp3:	0.182
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.752
MDCK Permeability:	1.4942892448743805e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.964
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.02
30% Bioavailability (F30%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.12
Plasma Protein Binding (PPB):	85.91268157958984%
Volume Distribution (VD):	0.725
Pgp-substrate:	18.39182472229004%

ADMET: Metabolism

CYP1A2-inhibitor:	0.97
CYP1A2-substrate:	0.965
CYP2C19-inhibitor:	0.259
CYP2C19-substrate:	0.192
CYP2C9-inhibitor:	0.167
CYP2C9-substrate:	0.876
CYP2D6-inhibitor:	0.393
CYP2D6-substrate:	0.855
CYP3A4-inhibitor:	0.25
CYP3A4-substrate:	0.299

ADMET: Excretion

Clearance (CL):	13.147
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.114
Drug-inuced Liver Injury (DILI):	0.627
AMES Toxicity:	0.213
Rat Oral Acute Toxicity:	0.106
Maximum Recommended Daily Dose:	0.369
Skin Sensitization:	0.403
Carcinogencity:	0.559
Eye Corrosion:	0.913
Eye Irritation:	0.991
Respiratory Toxicity:	0.28

Download Data

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

Natural Product: NPC248786

Natural Product ID:	NPC248786
*Common Name:**	6-Hydroxy-4-Methoxy-5-Methylchromen-2-One
IUPAC Name:	6-hydroxy-4-methoxy-5-methylchromen-2-one
Synonyms:
Standard InCHIKey:	XGCHWRRIHYVQRO-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C11H10O4/c1-6-7(12)3-4-8-11(6)9(14-2)5-10(13)15-8/h3-5,12H,1-2H3
SMILES:	COc1cc(=O)oc2c1c(C)c(cc2)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL121357
PubChem CID:	23260079
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
NPO22473	Aspergillus clavatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24838010]
NPO21013	Lonchocarpus castilloi	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22473	Aspergillus clavatus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22124	Senecio integrifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15107	Eledone moschata	Species	Octopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9969	Nassarius reticulatus	Species	Nassariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11676	[candida] zeylanoides	Species	Debaryomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21185	Manica rubida	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23161	Dosidicus gigas	Species	Ommastrephidae	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

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	4.8	ug.mL-1	PMID[523190]

☑ 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 NPC248786 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	375
0.1-0.2	1927
0.2-0.3	5213
0.3-0.4	11367
0.4-0.5	6339
0.5-0.6	4867
0.6-0.7	5968
0.7-0.8	5879
0.8-0.85	683
0.85-0.9	69
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9062	High Similarity	NPC51087
0.9062	High Similarity	NPC161856
0.9062	High Similarity	NPC291119
0.9062	High Similarity	NPC281169
0.9	High Similarity	NPC14177
0.8992	High Similarity	NPC115861
0.8983	High Similarity	NPC163398
0.8814	High Similarity	NPC87563
0.881	High Similarity	NPC81261
0.878	High Similarity	NPC302211
0.8632	High Similarity	NPC141068
0.8537	High Similarity	NPC193193
0.8537	High Similarity	NPC31314
0.8512	High Similarity	NPC33717
0.8473	Intermediate Similarity	NPC277021
0.8456	Intermediate Similarity	NPC230157
0.8438	Intermediate Similarity	NPC95034
0.8438	Intermediate Similarity	NPC142087
0.843	Intermediate Similarity	NPC301321
0.8421	Intermediate Similarity	NPC126682
0.8421	Intermediate Similarity	NPC82271
0.84	Intermediate Similarity	NPC52247
0.84	Intermediate Similarity	NPC476165
0.84	Intermediate Similarity	NPC187868
0.839	Intermediate Similarity	NPC149545
0.8387	Intermediate Similarity	NPC474874
0.8372	Intermediate Similarity	NPC176590
0.8359	Intermediate Similarity	NPC101894
0.8358	Intermediate Similarity	NPC95162
0.8358	Intermediate Similarity	NPC139548
0.8358	Intermediate Similarity	NPC148835
0.8358	Intermediate Similarity	NPC20511
0.8358	Intermediate Similarity	NPC52086
0.8358	Intermediate Similarity	NPC76336
0.8347	Intermediate Similarity	NPC470837
0.8333	Intermediate Similarity	NPC474920
0.8333	Intermediate Similarity	NPC476332
0.8333	Intermediate Similarity	NPC473464
0.8296	Intermediate Similarity	NPC13067
0.8258	Intermediate Similarity	NPC329427
0.8258	Intermediate Similarity	NPC137949
0.8258	Intermediate Similarity	NPC194277
0.8258	Intermediate Similarity	NPC317601
0.8226	Intermediate Similarity	NPC283616
0.8222	Intermediate Similarity	NPC38874
0.822	Intermediate Similarity	NPC233320
0.8211	Intermediate Similarity	NPC290470
0.8211	Intermediate Similarity	NPC154256
0.8203	Intermediate Similarity	NPC474237
0.8203	Intermediate Similarity	NPC265910
0.8203	Intermediate Similarity	NPC91475
0.8195	Intermediate Similarity	NPC26673
0.8195	Intermediate Similarity	NPC163557
0.8189	Intermediate Similarity	NPC477151
0.8189	Intermediate Similarity	NPC46634
0.8189	Intermediate Similarity	NPC132518
0.8188	Intermediate Similarity	NPC7439
0.8188	Intermediate Similarity	NPC256555
0.8188	Intermediate Similarity	NPC110067
0.8188	Intermediate Similarity	NPC91492
0.8188	Intermediate Similarity	NPC34245
0.8182	Intermediate Similarity	NPC142530
0.8175	Intermediate Similarity	NPC100108
0.8175	Intermediate Similarity	NPC307253
0.8175	Intermediate Similarity	NPC322569
0.8175	Intermediate Similarity	NPC277798
0.8175	Intermediate Similarity	NPC302107
0.8168	Intermediate Similarity	NPC123127
0.8168	Intermediate Similarity	NPC27239
0.8162	Intermediate Similarity	NPC164148
0.8162	Intermediate Similarity	NPC43500
0.816	Intermediate Similarity	NPC471449
0.816	Intermediate Similarity	NPC98748
0.8154	Intermediate Similarity	NPC71525
0.8151	Intermediate Similarity	NPC241549
0.814	Intermediate Similarity	NPC93219
0.814	Intermediate Similarity	NPC244495
0.814	Intermediate Similarity	NPC168259
0.8134	Intermediate Similarity	NPC92830
0.813	Intermediate Similarity	NPC473718
0.8129	Intermediate Similarity	NPC36732
0.8125	Intermediate Similarity	NPC477152
0.812	Intermediate Similarity	NPC474635
0.8106	Intermediate Similarity	NPC244799
0.8106	Intermediate Similarity	NPC240722
0.8099	Intermediate Similarity	NPC275627
0.8095	Intermediate Similarity	NPC247553
0.8092	Intermediate Similarity	NPC201419
0.8092	Intermediate Similarity	NPC185066
0.8088	Intermediate Similarity	NPC476171
0.8088	Intermediate Similarity	NPC105493
0.8088	Intermediate Similarity	NPC474886
0.8085	Intermediate Similarity	NPC178129
0.8085	Intermediate Similarity	NPC60389
0.808	Intermediate Similarity	NPC96705
0.8077	Intermediate Similarity	NPC329272
0.8065	Intermediate Similarity	NPC128633
0.8062	Intermediate Similarity	NPC147896
0.8062	Intermediate Similarity	NPC190086
0.8062	Intermediate Similarity	NPC276962
0.8062	Intermediate Similarity	NPC140521
0.806	Intermediate Similarity	NPC474810
0.806	Intermediate Similarity	NPC31849
0.8058	Intermediate Similarity	NPC6568
0.8051	Intermediate Similarity	NPC227255
0.8051	Intermediate Similarity	NPC139891
0.8051	Intermediate Similarity	NPC288760
0.8047	Intermediate Similarity	NPC325301
0.8047	Intermediate Similarity	NPC74137
0.8045	Intermediate Similarity	NPC147317
0.8033	Intermediate Similarity	NPC280760
0.8031	Intermediate Similarity	NPC45663
0.8016	Intermediate Similarity	NPC298796
0.8016	Intermediate Similarity	NPC51341
0.8015	Intermediate Similarity	NPC243688
0.8015	Intermediate Similarity	NPC92932
0.8015	Intermediate Similarity	NPC121740
0.8015	Intermediate Similarity	NPC258567
0.8015	Intermediate Similarity	NPC224774
0.8015	Intermediate Similarity	NPC181715
0.8	Intermediate Similarity	NPC50896
0.8	Intermediate Similarity	NPC204353
0.8	Intermediate Similarity	NPC249836
0.8	Intermediate Similarity	NPC326600
0.8	Intermediate Similarity	NPC169450
0.8	Intermediate Similarity	NPC211164
0.8	Intermediate Similarity	NPC27394
0.7985	Intermediate Similarity	NPC137669
0.7985	Intermediate Similarity	NPC319969
0.7984	Intermediate Similarity	NPC296526
0.7984	Intermediate Similarity	NPC261992
0.797	Intermediate Similarity	NPC32463
0.797	Intermediate Similarity	NPC2989
0.7969	Intermediate Similarity	NPC168707
0.7969	Intermediate Similarity	NPC48623
0.7966	Intermediate Similarity	NPC130817
0.7966	Intermediate Similarity	NPC93831
0.7958	Intermediate Similarity	NPC211565
0.7956	Intermediate Similarity	NPC131198
0.7955	Intermediate Similarity	NPC469453
0.7953	Intermediate Similarity	NPC328485
0.7953	Intermediate Similarity	NPC2058
0.7943	Intermediate Similarity	NPC86069
0.7941	Intermediate Similarity	NPC234865
0.7937	Intermediate Similarity	NPC124916
0.7937	Intermediate Similarity	NPC63010
0.7937	Intermediate Similarity	NPC152306
0.7937	Intermediate Similarity	NPC329980
0.7937	Intermediate Similarity	NPC265547
0.7929	Intermediate Similarity	NPC236419
0.7926	Intermediate Similarity	NPC241341
0.7926	Intermediate Similarity	NPC36437
0.7926	Intermediate Similarity	NPC233018
0.7926	Intermediate Similarity	NPC185777
0.7926	Intermediate Similarity	NPC472524
0.7923	Intermediate Similarity	NPC61685
0.7923	Intermediate Similarity	NPC78446
0.7923	Intermediate Similarity	NPC229113
0.792	Intermediate Similarity	NPC69539
0.7914	Intermediate Similarity	NPC300611
0.791	Intermediate Similarity	NPC191395
0.791	Intermediate Similarity	NPC250727
0.791	Intermediate Similarity	NPC73738
0.7907	Intermediate Similarity	NPC188997
0.7907	Intermediate Similarity	NPC327070
0.7907	Intermediate Similarity	NPC311219
0.7903	Intermediate Similarity	NPC41851
0.7902	Intermediate Similarity	NPC139839
0.7902	Intermediate Similarity	NPC142863
0.7899	Intermediate Similarity	NPC127676
0.7895	Intermediate Similarity	NPC271832
0.7895	Intermediate Similarity	NPC474289
0.7895	Intermediate Similarity	NPC59654
0.7895	Intermediate Similarity	NPC238309
0.7895	Intermediate Similarity	NPC168710
0.7891	Intermediate Similarity	NPC163200
0.7891	Intermediate Similarity	NPC473875
0.7891	Intermediate Similarity	NPC129176
0.7891	Intermediate Similarity	NPC96423
0.7886	Intermediate Similarity	NPC98372
0.7886	Intermediate Similarity	NPC266116
0.7883	Intermediate Similarity	NPC38099
0.7883	Intermediate Similarity	NPC26954
0.7883	Intermediate Similarity	NPC286843
0.7879	Intermediate Similarity	NPC474670
0.7877	Intermediate Similarity	NPC477690
0.7874	Intermediate Similarity	NPC281356
0.7874	Intermediate Similarity	NPC32152
0.7868	Intermediate Similarity	NPC213173
0.7868	Intermediate Similarity	NPC473054
0.7868	Intermediate Similarity	NPC131950
0.7868	Intermediate Similarity	NPC180716
0.7868	Intermediate Similarity	NPC309953
0.7868	Intermediate Similarity	NPC62366
0.7868	Intermediate Similarity	NPC224475
0.7863	Intermediate Similarity	NPC320847
0.7863	Intermediate Similarity	NPC471827
0.7863	Intermediate Similarity	NPC471828
0.7863	Intermediate Similarity	NPC170749
0.7857	Intermediate Similarity	NPC220106

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 NPC248786 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	367
0.1-0.2	1031
0.2-0.3	1759
0.3-0.4	2660
0.4-0.5	1823
0.5-0.6	1033
0.6-0.7	333
0.7-0.8	120
0.8-0.85	19
0.85-0.9	5
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8618	High Similarity	NPD3496	Discontinued
0.84	Intermediate Similarity	NPD1611	Approved
0.84	Intermediate Similarity	NPD422	Phase 1
0.814	Intermediate Similarity	NPD2797	Approved
0.813	Intermediate Similarity	NPD6671	Approved
0.8095	Intermediate Similarity	NPD4626	Approved
0.8051	Intermediate Similarity	NPD9697	Approved
0.7985	Intermediate Similarity	NPD4060	Phase 1
0.797	Intermediate Similarity	NPD3268	Approved
0.7923	Intermediate Similarity	NPD3225	Approved
0.7907	Intermediate Similarity	NPD9717	Approved
0.7874	Intermediate Similarity	NPD5691	Approved
0.7863	Intermediate Similarity	NPD1203	Approved
0.7842	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD968	Approved
0.7826	Intermediate Similarity	NPD2935	Discontinued
0.7823	Intermediate Similarity	NPD1398	Phase 1
0.7794	Intermediate Similarity	NPD447	Suspended
0.7727	Intermediate Similarity	NPD3266	Approved
0.7727	Intermediate Similarity	NPD3267	Approved
0.7717	Intermediate Similarity	NPD7644	Approved
0.7704	Intermediate Similarity	NPD411	Approved
0.7692	Intermediate Similarity	NPD1535	Discovery
0.7674	Intermediate Similarity	NPD1778	Approved
0.7652	Intermediate Similarity	NPD6696	Suspended
0.7638	Intermediate Similarity	NPD7340	Approved
0.7634	Intermediate Similarity	NPD1481	Phase 2
0.7626	Intermediate Similarity	NPD4308	Phase 3
0.7606	Intermediate Similarity	NPD3750	Approved
0.7603	Intermediate Similarity	NPD1653	Approved
0.7574	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7536	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD1548	Phase 1
0.7518	Intermediate Similarity	NPD2346	Discontinued
0.75	Intermediate Similarity	NPD1608	Approved
0.75	Intermediate Similarity	NPD4625	Phase 3
0.7483	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD2861	Phase 2
0.7481	Intermediate Similarity	NPD2237	Approved
0.748	Intermediate Similarity	NPD290	Approved
0.7464	Intermediate Similarity	NPD4140	Approved
0.7462	Intermediate Similarity	NPD5585	Approved
0.746	Intermediate Similarity	NPD5535	Approved
0.7445	Intermediate Similarity	NPD7985	Registered
0.7444	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD4749	Approved
0.7426	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD6832	Phase 2
0.7424	Intermediate Similarity	NPD1610	Phase 2
0.7422	Intermediate Similarity	NPD709	Approved
0.7417	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD1652	Phase 2
0.741	Intermediate Similarity	NPD5124	Phase 1
0.741	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD1019	Discontinued
0.7394	Intermediate Similarity	NPD5762	Approved
0.7394	Intermediate Similarity	NPD5763	Approved
0.7388	Intermediate Similarity	NPD1283	Approved
0.7364	Intermediate Similarity	NPD9493	Approved
0.7357	Intermediate Similarity	NPD6653	Approved
0.7339	Intermediate Similarity	NPD1358	Approved
0.7338	Intermediate Similarity	NPD4307	Phase 2
0.7324	Intermediate Similarity	NPD1551	Phase 2
0.7319	Intermediate Similarity	NPD2313	Discontinued
0.7319	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD3226	Approved
0.7315	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD4908	Phase 1
0.7293	Intermediate Similarity	NPD1091	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.7266	Intermediate Similarity	NPD6233	Phase 2
0.7258	Intermediate Similarity	NPD3134	Approved
0.7254	Intermediate Similarity	NPD3748	Approved
0.7246	Intermediate Similarity	NPD7095	Approved
0.7244	Intermediate Similarity	NPD228	Approved
0.7241	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1613	Approved
0.7214	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD6032	Approved
0.7194	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1296	Phase 2
0.7194	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD1048	Approved
0.7185	Intermediate Similarity	NPD4359	Approved
0.7164	Intermediate Similarity	NPD1281	Approved
0.7163	Intermediate Similarity	NPD6355	Discontinued
0.7162	Intermediate Similarity	NPD1578	Phase 2
0.7133	Intermediate Similarity	NPD7033	Discontinued
0.7133	Intermediate Similarity	NPD2370	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD2799	Discontinued
0.7132	Intermediate Similarity	NPD1241	Discontinued
0.7125	Intermediate Similarity	NPD5844	Phase 1
0.7124	Intermediate Similarity	NPD1465	Phase 2
0.7124	Intermediate Similarity	NPD7819	Suspended
0.7124	Intermediate Similarity	NPD2801	Approved
0.7123	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD1894	Discontinued
0.7114	Intermediate Similarity	NPD2675	Approved
0.7114	Intermediate Similarity	NPD2676	Approved
0.7111	Intermediate Similarity	NPD2232	Approved
0.7111	Intermediate Similarity	NPD2233	Approved
0.7111	Intermediate Similarity	NPD2230	Approved
0.7101	Intermediate Similarity	NPD1712	Approved
0.7095	Intermediate Similarity	NPD1511	Approved
0.7083	Intermediate Similarity	NPD4477	Approved
0.7083	Intermediate Similarity	NPD6100	Approved
0.7083	Intermediate Similarity	NPD6099	Approved
0.7083	Intermediate Similarity	NPD4476	Approved
0.708	Intermediate Similarity	NPD6362	Approved
0.7078	Intermediate Similarity	NPD5402	Approved
0.7071	Intermediate Similarity	NPD6798	Discontinued
0.7059	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7054	Intermediate Similarity	NPD7635	Approved
0.705	Intermediate Similarity	NPD596	Approved
0.705	Intermediate Similarity	NPD600	Approved
0.7047	Intermediate Similarity	NPD2532	Approved
0.7047	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2534	Approved
0.7047	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD2533	Approved
0.7034	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6002	Phase 3
0.7034	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7034	Intermediate Similarity	NPD6004	Phase 3
0.7034	Intermediate Similarity	NPD6005	Phase 3
0.7029	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD288	Approved
0.7023	Intermediate Similarity	NPD7157	Approved
0.7021	Intermediate Similarity	NPD8032	Phase 2
0.7021	Intermediate Similarity	NPD840	Approved
0.7021	Intermediate Similarity	NPD839	Approved
0.7009	Intermediate Similarity	NPD9295	Approved
0.7008	Intermediate Similarity	NPD2684	Approved
0.7	Intermediate Similarity	NPD6273	Approved
0.7	Intermediate Similarity	NPD1512	Approved
0.6986	Remote Similarity	NPD2424	Discontinued
0.6985	Remote Similarity	NPD2235	Phase 2
0.6985	Remote Similarity	NPD2231	Phase 2
0.6985	Remote Similarity	NPD1840	Phase 2
0.6972	Remote Similarity	NPD2979	Phase 3
0.6963	Remote Similarity	NPD3847	Discontinued
0.6957	Remote Similarity	NPD987	Approved
0.6942	Remote Similarity	NPD844	Approved
0.694	Remote Similarity	NPD1651	Approved
0.694	Remote Similarity	NPD3445	Approved
0.694	Remote Similarity	NPD3444	Approved
0.694	Remote Similarity	NPD3443	Approved
0.6939	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2614	Approved
0.6923	Remote Similarity	NPD7843	Approved
0.6923	Remote Similarity	NPD1933	Approved
0.6923	Remote Similarity	NPD4340	Discontinued
0.6923	Remote Similarity	NPD821	Approved
0.6918	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6906	Remote Similarity	NPD6584	Phase 3
0.6906	Remote Similarity	NPD2798	Approved
0.6901	Remote Similarity	NPD4870	Approved
0.6897	Remote Similarity	NPD1510	Phase 2
0.6892	Remote Similarity	NPD4628	Phase 3
0.6892	Remote Similarity	NPD7003	Approved
0.6887	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6090	Discontinued
0.6879	Remote Similarity	NPD3749	Approved
0.6879	Remote Similarity	NPD3027	Phase 3
0.6875	Remote Similarity	NPD4097	Suspended
0.6871	Remote Similarity	NPD1549	Phase 2
0.687	Remote Similarity	NPD5283	Phase 1
0.6866	Remote Similarity	NPD9545	Approved
0.6859	Remote Similarity	NPD3817	Phase 2
0.6853	Remote Similarity	NPD1240	Approved
0.6849	Remote Similarity	NPD1519	Approved
0.6849	Remote Similarity	NPD1538	Phase 1
0.6849	Remote Similarity	NPD1537	Approved
0.6848	Remote Similarity	NPD7549	Discontinued
0.6842	Remote Similarity	NPD920	Approved
0.6842	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD1934	Approved
0.6831	Remote Similarity	NPD3764	Approved
0.6828	Remote Similarity	NPD7097	Phase 1
0.6822	Remote Similarity	NPD4750	Phase 3
0.6815	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD7768	Phase 2
0.6813	Remote Similarity	NPD6232	Discontinued
0.6812	Remote Similarity	NPD5327	Phase 3
0.6806	Remote Similarity	NPD230	Phase 1
0.6803	Remote Similarity	NPD6800	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD2344	Approved
0.68	Remote Similarity	NPD6667	Approved
0.68	Remote Similarity	NPD6666	Approved
0.6795	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5929	Approved
0.6794	Remote Similarity	NPD1138	Approved
0.6791	Remote Similarity	NPD5536	Phase 2

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