NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	276.06
Volume:	261.953
LogP:	1.766
LogD:	1.363
LogS:	-3.602
# Rotatable Bonds:	1
TPSA:	89.9
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.606
Synthetic Accessibility Score:	4.249
Fsp3:	0.357
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.768
MDCK Permeability:	2.1183714125072584e-05
Pgp-inhibitor:	0.009
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.033
20% Bioavailability (F20%):	0.025
30% Bioavailability (F30%):	0.533

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.241
Plasma Protein Binding (PPB):	81.58699798583984%
Volume Distribution (VD):	0.678
Pgp-substrate:	23.37557601928711%

ADMET: Metabolism

CYP1A2-inhibitor:	0.298
CYP1A2-substrate:	0.635
CYP2C19-inhibitor:	0.201
CYP2C19-substrate:	0.68
CYP2C9-inhibitor:	0.172
CYP2C9-substrate:	0.627
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.204
CYP3A4-inhibitor:	0.314
CYP3A4-substrate:	0.269

ADMET: Excretion

Clearance (CL):	8.584
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.143
Drug-inuced Liver Injury (DILI):	0.785
AMES Toxicity:	0.119
Rat Oral Acute Toxicity:	0.169
Maximum Recommended Daily Dose:	0.605
Skin Sensitization:	0.335
Carcinogencity:	0.107
Eye Corrosion:	0.004
Eye Irritation:	0.536
Respiratory Toxicity:	0.202

Download Data

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

Natural Product: NPC473395

Natural Product ID:	NPC473395
*Common Name:**	Talaroflavone
IUPAC Name:	5',7-dihydroxy-5-methoxy-3'-methylspiro[2-benzofuran-3,4'-cyclopent-2-ene]-1,1'-dione
Synonyms:	talaroflavone
Standard InCHIKey:	ISNKGHIHBITAEG-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H12O6/c1-6-3-10(16)12(17)14(6)8-4-7(19-2)5-9(15)11(8)13(18)20-14/h3-5,12,15,17H,1-2H3
SMILES:	COc1cc(O)c2c(c1)C1(OC2=O)C(=CC(=O)C1O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL408995
PubChem CID:	14824655
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000301] Benzofurans [CHEMONTID:0001578] Benzofuranones

*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
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18494522]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22276679]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25265160]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841051]
NPO32908	Alternaria sp.	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30794407]

☑ 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	26
Others	1

Activity Type	# Activity
Cell Line	1
Individual Protein	25
Protein Complex	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2216	Individual Protein	DNA polymerase beta	Rattus norvegicus	IC50	=	16300.0	nM	PMID[475414]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	IC50	=	86500.0	nM	PMID[475414]
NPT1864	Cell Line	L5178Y	Mus musculus	Activity	=	92.9	%	PMID[475415]
NPT1660	Individual Protein	NUAK family SNF1-like kinase 1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1432	Individual Protein	Serine/threonine-protein kinase Aurora-A	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1433	Individual Protein	Serine/threonine-protein kinase Aurora-B	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1434	Individual Protein	Serine/threonine-protein kinase B-raf	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT285	Individual Protein	Epidermal growth factor receptor erbB1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT2572	Individual Protein	Ephrin type-B receptor 4	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1371	Individual Protein	Cyclin-dependent kinase 2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT286	Individual Protein	Receptor protein-tyrosine kinase erbB-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1436	Individual Protein	Focal adhesion kinase 1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT2571	Individual Protein	Mitogen-activated protein kinase kinase kinase 8	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1438	Individual Protein	Insulin-like growth factor I receptor	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT36	Individual Protein	Tyrosine-protein kinase SRC	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1478	Individual Protein	Vascular endothelial growth factor receptor 2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT2573	Individual Protein	Vascular endothelial growth factor receptor 3	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1650	Individual Protein	Tyrosine-protein kinase receptor FLT3	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT2574	Individual Protein	Insulin receptor	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1337	Individual Protein	Hepatocyte growth factor receptor	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT2575	Individual Protein	Platelet-derived growth factor receptor beta	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1598	Individual Protein	Casein kinase II alpha	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1702	Individual Protein	Serine/threonine-protein kinase PLK4	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT2576	Individual Protein	Tyrosine-protein kinase TIE-2	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT728	Individual Protein	Serine/threonine-protein kinase AKT	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT1560	Protein Complex	Cyclin-dependent kinase 4/cyclin D1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]
NPT831	Individual Protein	Serine/threonine-protein kinase PLK1	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[475415]

☑ 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 NPC473395 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	349
0.1-0.2	1419
0.2-0.3	3597
0.3-0.4	7637
0.4-0.5	10277
0.5-0.6	4506
0.6-0.7	5700
0.7-0.8	7219
0.8-0.85	1669
0.85-0.9	271
0.9-0.95	52
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9211	High Similarity	NPC179178
0.915	High Similarity	NPC200773
0.915	High Similarity	NPC240768
0.9139	High Similarity	NPC14098
0.9051	High Similarity	NPC117985
0.902	High Similarity	NPC4423
0.902	High Similarity	NPC77325
0.9013	High Similarity	NPC210320
0.8993	High Similarity	NPC90411
0.8974	High Similarity	NPC79998
0.8974	High Similarity	NPC99381
0.8961	High Similarity	NPC96501
0.8954	High Similarity	NPC215711
0.8954	High Similarity	NPC73411
0.891	High Similarity	NPC301233
0.8903	High Similarity	NPC215921
0.8903	High Similarity	NPC70016
0.8896	High Similarity	NPC270160
0.8896	High Similarity	NPC237440
0.8896	High Similarity	NPC198927
0.8889	High Similarity	NPC166583
0.8889	High Similarity	NPC53362
0.8874	High Similarity	NPC51106
0.8874	High Similarity	NPC472006
0.8861	High Similarity	NPC246466
0.8861	High Similarity	NPC84935
0.8861	High Similarity	NPC190020
0.8861	High Similarity	NPC77679
0.8854	High Similarity	NPC199926
0.8839	High Similarity	NPC469619
0.8839	High Similarity	NPC469670
0.8824	High Similarity	NPC107625
0.8824	High Similarity	NPC260946
0.8816	High Similarity	NPC210425
0.8816	High Similarity	NPC86373
0.8816	High Similarity	NPC280404
0.8816	High Similarity	NPC277426
0.8805	High Similarity	NPC470339
0.8797	High Similarity	NPC150227
0.879	High Similarity	NPC281477
0.8758	High Similarity	NPC316535
0.875	High Similarity	NPC469542
0.875	High Similarity	NPC472055
0.8742	High Similarity	NPC1704
0.8742	High Similarity	NPC244923
0.8742	High Similarity	NPC67650
0.8734	High Similarity	NPC82592
0.8734	High Similarity	NPC16082
0.8726	High Similarity	NPC167903
0.8725	High Similarity	NPC135837
0.8718	High Similarity	NPC56204
0.871	High Similarity	NPC153417
0.8684	High Similarity	NPC474385
0.8679	High Similarity	NPC472050
0.8671	High Similarity	NPC478231
0.8671	High Similarity	NPC192189
0.8659	High Similarity	NPC473094
0.8645	High Similarity	NPC472036
0.8645	High Similarity	NPC8817
0.8636	High Similarity	NPC83272
0.8616	High Similarity	NPC170189
0.8616	High Similarity	NPC208173
0.8616	High Similarity	NPC478230
0.8616	High Similarity	NPC69043
0.8609	High Similarity	NPC268052
0.8609	High Similarity	NPC275356
0.8609	High Similarity	NPC247409
0.8608	High Similarity	NPC76041
0.8608	High Similarity	NPC184284
0.8608	High Similarity	NPC478224
0.8608	High Similarity	NPC271681
0.8608	High Similarity	NPC115249
0.8606	High Similarity	NPC473096
0.8606	High Similarity	NPC473095
0.8599	High Similarity	NPC472891
0.8599	High Similarity	NPC119929
0.8598	High Similarity	NPC20237
0.8591	High Similarity	NPC180905
0.8591	High Similarity	NPC182496
0.859	High Similarity	NPC470359
0.8589	High Similarity	NPC249181
0.8581	High Similarity	NPC85734
0.8581	High Similarity	NPC32058
0.8581	High Similarity	NPC472033
0.8581	High Similarity	NPC470357
0.8571	High Similarity	NPC27106
0.8562	High Similarity	NPC469579
0.8562	High Similarity	NPC297985
0.8562	High Similarity	NPC82913
0.8562	High Similarity	NPC322112
0.8553	High Similarity	NPC137301
0.8553	High Similarity	NPC158472
0.8545	High Similarity	NPC283041
0.8543	High Similarity	NPC212693
0.8543	High Similarity	NPC94248
0.8543	High Similarity	NPC191835
0.8537	High Similarity	NPC191930
0.8528	High Similarity	NPC48860
0.8526	High Similarity	NPC202494
0.8526	High Similarity	NPC21835
0.8519	High Similarity	NPC470810
0.8516	High Similarity	NPC472034
0.8516	High Similarity	NPC75694
0.8516	High Similarity	NPC297788
0.8509	High Similarity	NPC472889
0.85	High Similarity	NPC478221
0.85	High Similarity	NPC317585
0.85	High Similarity	NPC472890
0.8497	Intermediate Similarity	NPC475730
0.8491	Intermediate Similarity	NPC268992
0.8491	Intermediate Similarity	NPC470340
0.8491	Intermediate Similarity	NPC470338
0.8491	Intermediate Similarity	NPC51824
0.8491	Intermediate Similarity	NPC113608
0.8491	Intermediate Similarity	NPC470337
0.8487	Intermediate Similarity	NPC139634
0.8487	Intermediate Similarity	NPC52358
0.8487	Intermediate Similarity	NPC32360
0.8487	Intermediate Similarity	NPC105456
0.8485	Intermediate Similarity	NPC165460
0.8481	Intermediate Similarity	NPC116822
0.8477	Intermediate Similarity	NPC70380
0.8471	Intermediate Similarity	NPC471642
0.8471	Intermediate Similarity	NPC471641
0.8471	Intermediate Similarity	NPC218569
0.8471	Intermediate Similarity	NPC240622
0.8471	Intermediate Similarity	NPC240253
0.8466	Intermediate Similarity	NPC96031
0.8466	Intermediate Similarity	NPC201560
0.8462	Intermediate Similarity	NPC324220
0.8462	Intermediate Similarity	NPC312630
0.8462	Intermediate Similarity	NPC473023
0.8457	Intermediate Similarity	NPC279732
0.8456	Intermediate Similarity	NPC153783
0.8452	Intermediate Similarity	NPC470932
0.8452	Intermediate Similarity	NPC184702
0.8447	Intermediate Similarity	NPC227062
0.8447	Intermediate Similarity	NPC272550
0.8438	Intermediate Similarity	NPC303950
0.8438	Intermediate Similarity	NPC155686
0.8431	Intermediate Similarity	NPC165172
0.8428	Intermediate Similarity	NPC46882
0.8428	Intermediate Similarity	NPC132990
0.8428	Intermediate Similarity	NPC204350
0.8424	Intermediate Similarity	NPC211592
0.8424	Intermediate Similarity	NPC472049
0.8421	Intermediate Similarity	NPC197666
0.8421	Intermediate Similarity	NPC33144
0.8421	Intermediate Similarity	NPC126739
0.8421	Intermediate Similarity	NPC478200
0.8418	Intermediate Similarity	NPC277032
0.8411	Intermediate Similarity	NPC235115
0.8408	Intermediate Similarity	NPC137296
0.8405	Intermediate Similarity	NPC470358
0.8405	Intermediate Similarity	NPC200594
0.8405	Intermediate Similarity	NPC243701
0.8397	Intermediate Similarity	NPC473692
0.8395	Intermediate Similarity	NPC478225
0.8395	Intermediate Similarity	NPC477833
0.8395	Intermediate Similarity	NPC478226
0.8387	Intermediate Similarity	NPC258307
0.8387	Intermediate Similarity	NPC476164
0.8387	Intermediate Similarity	NPC476310
0.8385	Intermediate Similarity	NPC471456
0.8385	Intermediate Similarity	NPC68727
0.8385	Intermediate Similarity	NPC175192
0.8377	Intermediate Similarity	NPC313123
0.8377	Intermediate Similarity	NPC158634
0.8377	Intermediate Similarity	NPC478217
0.8375	Intermediate Similarity	NPC321363
0.8375	Intermediate Similarity	NPC180944
0.8375	Intermediate Similarity	NPC256141
0.8375	Intermediate Similarity	NPC253904
0.8375	Intermediate Similarity	NPC161159
0.8375	Intermediate Similarity	NPC275878
0.8373	Intermediate Similarity	NPC53640
0.8372	Intermediate Similarity	NPC475148
0.8372	Intermediate Similarity	NPC475656
0.8366	Intermediate Similarity	NPC471819
0.8365	Intermediate Similarity	NPC475717
0.8365	Intermediate Similarity	NPC470908
0.8365	Intermediate Similarity	NPC267117
0.8365	Intermediate Similarity	NPC470107
0.8364	Intermediate Similarity	NPC475985
0.8354	Intermediate Similarity	NPC2569
0.8354	Intermediate Similarity	NPC317544
0.8354	Intermediate Similarity	NPC172329
0.8344	Intermediate Similarity	NPC477410
0.8344	Intermediate Similarity	NPC138978
0.8333	Intermediate Similarity	NPC313717
0.8333	Intermediate Similarity	NPC315306
0.8333	Intermediate Similarity	NPC164427
0.8333	Intermediate Similarity	NPC313922
0.8323	Intermediate Similarity	NPC291510
0.8323	Intermediate Similarity	NPC197188
0.8323	Intermediate Similarity	NPC150023
0.8323	Intermediate Similarity	NPC43872
0.8323	Intermediate Similarity	NPC74397
0.8323	Intermediate Similarity	NPC203080
0.8323	Intermediate Similarity	NPC171870

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 NPC473395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	303
0.1-0.2	899
0.2-0.3	1963
0.3-0.4	2540
0.4-0.5	1881
0.5-0.6	995
0.6-0.7	394
0.7-0.8	154
0.8-0.85	18
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8516	High Similarity	NPD2533	Approved
0.8516	High Similarity	NPD2532	Approved
0.8516	High Similarity	NPD2534	Approved
0.8487	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.811	Intermediate Similarity	NPD3882	Suspended
0.8061	Intermediate Similarity	NPD7075	Discontinued
0.8037	Intermediate Similarity	NPD1934	Approved
0.7988	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6799	Approved
0.7939	Intermediate Similarity	NPD3817	Phase 2
0.7927	Intermediate Similarity	NPD6801	Discontinued
0.7914	Intermediate Similarity	NPD6599	Discontinued
0.7914	Intermediate Similarity	NPD4380	Phase 2
0.7895	Intermediate Similarity	NPD3818	Discontinued
0.7888	Intermediate Similarity	NPD1512	Approved
0.7882	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7882	Intermediate Similarity	NPD6166	Phase 2
0.7879	Intermediate Similarity	NPD7819	Suspended
0.7879	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD6232	Discontinued
0.7857	Intermediate Similarity	NPD230	Phase 1
0.7844	Intermediate Similarity	NPD3749	Approved
0.7836	Intermediate Similarity	NPD7473	Discontinued
0.7834	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5402	Approved
0.7826	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD1510	Phase 2
0.7792	Intermediate Similarity	NPD1240	Approved
0.7785	Intermediate Similarity	NPD1549	Phase 2
0.7784	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD2801	Approved
0.7765	Intermediate Similarity	NPD5711	Approved
0.7765	Intermediate Similarity	NPD5710	Approved
0.7764	Intermediate Similarity	NPD1511	Approved
0.7738	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD2800	Approved
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD919	Approved
0.7692	Intermediate Similarity	NPD1607	Approved
0.7688	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD1465	Phase 2
0.7657	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7657	Intermediate Similarity	NPD6797	Phase 2
0.7644	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.764	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5403	Approved
0.7622	Intermediate Similarity	NPD920	Approved
0.7614	Intermediate Similarity	NPD6559	Discontinued
0.7614	Intermediate Similarity	NPD7251	Discontinued
0.7607	Intermediate Similarity	NPD5401	Approved
0.7602	Intermediate Similarity	NPD6959	Discontinued
0.76	Intermediate Similarity	NPD7074	Phase 3
0.7588	Intermediate Similarity	NPD6234	Discontinued
0.7578	Intermediate Similarity	NPD3750	Approved
0.7574	Intermediate Similarity	NPD4966	Approved
0.7574	Intermediate Similarity	NPD4965	Approved
0.7574	Intermediate Similarity	NPD4967	Phase 2
0.7571	Intermediate Similarity	NPD7808	Phase 3
0.7544	Intermediate Similarity	NPD5494	Approved
0.7543	Intermediate Similarity	NPD5844	Phase 1
0.7543	Intermediate Similarity	NPD7054	Approved
0.7516	Intermediate Similarity	NPD1243	Approved
0.7514	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD1247	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.75	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7472	Approved
0.7486	Intermediate Similarity	NPD3751	Discontinued
0.7469	Intermediate Similarity	NPD4628	Phase 3
0.744	Intermediate Similarity	NPD7411	Suspended
0.7438	Intermediate Similarity	NPD2796	Approved
0.7438	Intermediate Similarity	NPD2935	Discontinued
0.7438	Intermediate Similarity	NPD1551	Phase 2
0.7412	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD447	Suspended
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD7228	Approved
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7342	Intermediate Similarity	NPD943	Approved
0.7321	Intermediate Similarity	NPD3226	Approved
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7314	Intermediate Similarity	NPD3926	Phase 2
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7289	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6005	Phase 3
0.7284	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6004	Phase 3
0.7284	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD6002	Phase 3
0.7273	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD7768	Phase 2
0.7267	Intermediate Similarity	NPD3748	Approved
0.7249	Intermediate Similarity	NPD6776	Approved
0.7249	Intermediate Similarity	NPD6777	Approved
0.7249	Intermediate Similarity	NPD6782	Approved
0.7249	Intermediate Similarity	NPD6780	Approved
0.7249	Intermediate Similarity	NPD6778	Approved
0.7249	Intermediate Similarity	NPD6781	Approved
0.7249	Intermediate Similarity	NPD6779	Approved
0.7222	Intermediate Similarity	NPD7685	Pre-registration
0.7215	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD3764	Approved
0.7212	Intermediate Similarity	NPD6190	Approved
0.7202	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5647	Approved
0.7178	Intermediate Similarity	NPD5762	Approved
0.7178	Intermediate Similarity	NPD5763	Approved
0.7178	Intermediate Similarity	NPD2344	Approved
0.7178	Intermediate Similarity	NPD2346	Discontinued
0.7175	Intermediate Similarity	NPD2403	Approved
0.7152	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD9545	Approved
0.7151	Intermediate Similarity	NPD5760	Phase 2
0.7151	Intermediate Similarity	NPD5761	Phase 2
0.7143	Intermediate Similarity	NPD9717	Approved
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7143	Intermediate Similarity	NPD8313	Approved
0.7143	Intermediate Similarity	NPD8312	Approved
0.7143	Intermediate Similarity	NPD6651	Approved
0.7135	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8151	Discontinued
0.7126	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD7930	Approved
0.7117	Intermediate Similarity	NPD6100	Approved
0.7117	Intermediate Similarity	NPD6099	Approved
0.7107	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7092	Intermediate Similarity	NPD7874	Approved
0.7091	Intermediate Similarity	NPD2654	Approved
0.7091	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD6355	Discontinued
0.7072	Intermediate Similarity	NPD5953	Discontinued
0.7062	Intermediate Similarity	NPD7229	Phase 3
0.7056	Intermediate Similarity	NPD7286	Phase 2
0.7055	Intermediate Similarity	NPD2799	Discontinued
0.7055	Intermediate Similarity	NPD7033	Discontinued
0.7047	Intermediate Similarity	NPD7696	Phase 3
0.7047	Intermediate Similarity	NPD7698	Approved
0.7047	Intermediate Similarity	NPD7697	Approved
0.7041	Intermediate Similarity	NPD6273	Approved
0.7037	Intermediate Similarity	NPD6653	Approved
0.7033	Intermediate Similarity	NPD7240	Approved
0.7033	Intermediate Similarity	NPD6764	Approved
0.7033	Intermediate Similarity	NPD6765	Approved
0.7025	Intermediate Similarity	NPD9494	Approved
0.7024	Intermediate Similarity	NPD7390	Discontinued
0.702	Intermediate Similarity	NPD9493	Approved
0.7019	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD4060	Phase 1
0.7019	Intermediate Similarity	NPD1613	Approved
0.701	Intermediate Similarity	NPD7870	Phase 2
0.701	Intermediate Similarity	NPD7871	Phase 2
0.7006	Intermediate Similarity	NPD1203	Approved
0.7006	Intermediate Similarity	NPD2309	Approved
0.7	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD411	Approved
0.6995	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD9268	Approved
0.699	Remote Similarity	NPD7701	Phase 2
0.6984	Remote Similarity	NPD6534	Approved
0.6984	Remote Similarity	NPD6535	Approved
0.6982	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.697	Remote Similarity	NPD1471	Phase 3
0.6968	Remote Similarity	NPD422	Phase 1
0.6952	Remote Similarity	NPD4287	Approved
0.6937	Remote Similarity	NPD3027	Phase 3
0.6928	Remote Similarity	NPD2424	Discontinued
0.6923	Remote Similarity	NPD1608	Approved
0.6923	Remote Similarity	NPD8320	Phase 1
0.6923	Remote Similarity	NPD8319	Approved
0.6914	Remote Similarity	NPD5353	Approved
0.6894	Remote Similarity	NPD2313	Discontinued
0.6894	Remote Similarity	NPD6798	Discontinued
0.6886	Remote Similarity	NPD1652	Phase 2
0.6884	Remote Similarity	NPD7783	Phase 2
0.6884	Remote Similarity	NPD7801	Approved
0.6884	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6785	Approved
0.6882	Remote Similarity	NPD6784	Approved
0.6875	Remote Similarity	NPD7700	Phase 2
0.6875	Remote Similarity	NPD7699	Phase 2
0.6871	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1653	Approved
0.6855	Remote Similarity	NPD1019	Discontinued
0.6848	Remote Similarity	NPD3658	Clinical (unspecified phase)
0.6833	Remote Similarity	NPD5242	Approved
0.6821	Remote Similarity	NPD6823	Phase 2
0.6821	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD7799	Discontinued
0.6805	Remote Similarity	NPD2354	Approved
0.6792	Remote Similarity	NPD1470	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