NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	238.06
Volume:	247.606
LogP:	3.715
LogD:	2.968
LogS:	-3.652
# Rotatable Bonds:	1
TPSA:	50.44
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.708
Synthetic Accessibility Score:	1.923
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.74
MDCK Permeability:	1.4797291441936977e-05
Pgp-inhibitor:	0.013
Pgp-substrate:	0.253
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.992
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.125
Plasma Protein Binding (PPB):	97.86548614501953%
Volume Distribution (VD):	0.474
Pgp-substrate:	2.6522035598754883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.984
CYP1A2-substrate:	0.572
CYP2C19-inhibitor:	0.846
CYP2C19-substrate:	0.076
CYP2C9-inhibitor:	0.579
CYP2C9-substrate:	0.895
CYP2D6-inhibitor:	0.513
CYP2D6-substrate:	0.895
CYP3A4-inhibitor:	0.196
CYP3A4-substrate:	0.192

ADMET: Excretion

Clearance (CL):	3.512
Half-life (T1/2):	0.344

ADMET: Toxicity

hERG Blockers:	0.057
Human Hepatotoxicity (H-HT):	0.06
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.367
Rat Oral Acute Toxicity:	0.31
Maximum Recommended Daily Dose:	0.048
Skin Sensitization:	0.373
Carcinogencity:	0.748
Eye Corrosion:	0.015
Eye Irritation:	0.969
Respiratory Toxicity:	0.23

Download Data

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

Natural Product: NPC193805

Natural Product ID:	NPC193805
*Common Name:**	2'-Hydroxyflavone
IUPAC Name:	2-(2-hydroxyphenyl)chromen-4-one
Synonyms:	2'-Hydroxy Flavone; 2'-Hydroxyflavone
Standard InCHIKey:	ZZLQHXCRRMUGQJ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O3/c16-12-7-3-1-5-10(12)15-9-13(17)11-6-2-4-8-14(11)18-15/h1-9,16H
SMILES:	Oc1ccccc1c1cc(=O)c2c(o1)cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL144278
PubChem CID:	161860
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

*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
NPO22583	Daedaleopsis confragosa	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11014261]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17711348]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919067]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	The fungus is isolated from the leaves of L. rhodostegia, collected in June 2007 at Nanning, Guangxi Province, China	2007-JUN	PMID[20550196]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23501116]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24328302]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24471493]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28116906]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO24045	Lespedeza homoloba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24284	Hypoestes serpens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24045	Lespedeza homoloba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO15440	Chamaemelum nobile	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24173	Plutella xylostella	Species	Plutellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18557	Epicoccum nigrum	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24045	Lespedeza homoloba	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24284	Hypoestes serpens	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22583	Daedaleopsis confragosa	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24329	Primula farinosa	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20617	Tilletia laevis	Species	Tilletiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24216	Lolium perenne	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23916	Anthocleista grandiflora	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23957	Helleborus caucasicus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17647	Schkuhria multiflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16234	Orgyia australis postica	Species	Lymantriidae	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
ED50	1
IC50	6
Others	2

Activity Type	# Activity
Cell Line	1
Individual Protein	5
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3504	Individual Protein	Aldo-keto-reductase family 1 member C3	Homo sapiens	IC50	=	300.0	nM	PMID[522879]
NPT3507	Individual Protein	Aldo-keto reductase family 1 member C2	Homo sapiens	IC50	=	47100.0	nM	PMID[522879]
NPT3505	Individual Protein	Aldo-keto reductase family 1 member C1	Homo sapiens	IC50	=	6200.0	nM	PMID[522879]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	10000.0	nM	PMID[522880]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	IC50	>	10000.0	nM	PMID[522880]
NPT153	Individual Protein	Androgen Receptor	Homo sapiens	IC50	<	1000.0	nM	PMID[522880]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Protection	=	78.0	%	PMID[522876]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	15.6	mg.kg-1	PMID[522876]
NPT2	Others	Unspecified		logKi	=	-0.678	n.a.	PMID[522877]

☑ 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 NPC193805 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	452
0.1-0.2	2319
0.2-0.3	5457
0.3-0.4	12212
0.4-0.5	4746
0.5-0.6	5579
0.6-0.7	6004
0.7-0.8	4569
0.8-0.85	1090
0.85-0.9	226
0.9-0.95	41
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9431	High Similarity	NPC197425
0.9426	High Similarity	NPC22783
0.9417	High Similarity	NPC93730
0.9402	High Similarity	NPC32298
0.9355	High Similarity	NPC39753
0.9355	High Similarity	NPC115998
0.9322	High Similarity	NPC54243
0.928	High Similarity	NPC137264
0.9213	High Similarity	NPC57601
0.9206	High Similarity	NPC113006
0.92	High Similarity	NPC7569
0.916	High Similarity	NPC35744
0.9141	High Similarity	NPC172262
0.9134	High Similarity	NPC128216
0.9062	High Similarity	NPC274121
0.9062	High Similarity	NPC50898
0.9062	High Similarity	NPC78540
0.9062	High Similarity	NPC213216
0.9048	High Similarity	NPC278787
0.8992	High Similarity	NPC248872
0.8984	High Similarity	NPC287533
0.8976	High Similarity	NPC141549
0.8968	High Similarity	NPC187907
0.8952	High Similarity	NPC4164
0.8934	High Similarity	NPC314329
0.8931	High Similarity	NPC250266
0.8931	High Similarity	NPC228661
0.8931	High Similarity	NPC266597
0.8931	High Similarity	NPC299379
0.8923	High Similarity	NPC239495
0.8923	High Similarity	NPC9985
0.8862	High Similarity	NPC311219
0.8855	High Similarity	NPC47815
0.8855	High Similarity	NPC13408
0.8855	High Similarity	NPC256042
0.8855	High Similarity	NPC281917
0.8855	High Similarity	NPC124784
0.8855	High Similarity	NPC216361
0.8855	High Similarity	NPC127447
0.8855	High Similarity	NPC187432
0.8855	High Similarity	NPC194281
0.8855	High Similarity	NPC231772
0.8855	High Similarity	NPC234133
0.8855	High Similarity	NPC473887
0.8855	High Similarity	NPC116775
0.8855	High Similarity	NPC29353
0.8843	High Similarity	NPC201284
0.881	High Similarity	NPC41721
0.88	High Similarity	NPC2771
0.8788	High Similarity	NPC290291
0.8788	High Similarity	NPC476480
0.8788	High Similarity	NPC84585
0.8788	High Similarity	NPC275055
0.877	High Similarity	NPC233282
0.8731	High Similarity	NPC270883
0.8731	High Similarity	NPC305355
0.8731	High Similarity	NPC269652
0.8731	High Similarity	NPC235239
0.8731	High Similarity	NPC172986
0.8731	High Similarity	NPC475680
0.8731	High Similarity	NPC281207
0.8731	High Similarity	NPC261227
0.8722	High Similarity	NPC188947
0.8722	High Similarity	NPC329225
0.8722	High Similarity	NPC201395
0.8722	High Similarity	NPC280284
0.8722	High Similarity	NPC472460
0.8722	High Similarity	NPC99333
0.8722	High Similarity	NPC18457
0.8722	High Similarity	NPC147686
0.8712	High Similarity	NPC240593
0.8682	High Similarity	NPC270369
0.8682	High Similarity	NPC5515
0.8672	High Similarity	NPC238309
0.8667	High Similarity	NPC156590
0.8667	High Similarity	NPC147688
0.8667	High Similarity	NPC205006
0.8667	High Similarity	NPC118840
0.8667	High Similarity	NPC64908
0.8667	High Similarity	NPC110969
0.8667	High Similarity	NPC136840
0.8661	High Similarity	NPC298884
0.8657	High Similarity	NPC96565
0.8657	High Similarity	NPC55018
0.8657	High Similarity	NPC18260
0.8657	High Similarity	NPC78913
0.8657	High Similarity	NPC220062
0.8657	High Similarity	NPC301217
0.8657	High Similarity	NPC152042
0.8657	High Similarity	NPC143799
0.8657	High Similarity	NPC241838
0.8657	High Similarity	NPC261234
0.8657	High Similarity	NPC216978
0.8657	High Similarity	NPC303633
0.8655	High Similarity	NPC279916
0.8647	High Similarity	NPC160972
0.8647	High Similarity	NPC12296
0.8647	High Similarity	NPC295261
0.8647	High Similarity	NPC243083
0.8647	High Similarity	NPC107586
0.8647	High Similarity	NPC287246
0.8647	High Similarity	NPC296490
0.8647	High Similarity	NPC188879
0.8647	High Similarity	NPC32441
0.8647	High Similarity	NPC254841
0.8647	High Similarity	NPC13768
0.8647	High Similarity	NPC79943
0.8636	High Similarity	NPC39426
0.8636	High Similarity	NPC151113
0.8636	High Similarity	NPC234560
0.8618	High Similarity	NPC470092
0.8615	High Similarity	NPC31872
0.8615	High Similarity	NPC473584
0.8615	High Similarity	NPC308037
0.8615	High Similarity	NPC262359
0.8615	High Similarity	NPC64359
0.8615	High Similarity	NPC313618
0.8615	High Similarity	NPC475589
0.8615	High Similarity	NPC284424
0.8603	High Similarity	NPC1534
0.8603	High Similarity	NPC11561
0.8603	High Similarity	NPC226636
0.8594	High Similarity	NPC196034
0.8594	High Similarity	NPC125887
0.8593	High Similarity	NPC69769
0.8593	High Similarity	NPC145673
0.8593	High Similarity	NPC241100
0.8593	High Similarity	NPC103342
0.8593	High Similarity	NPC146679
0.8593	High Similarity	NPC103904
0.8593	High Similarity	NPC159275
0.8593	High Similarity	NPC184536
0.8593	High Similarity	NPC59951
0.8593	High Similarity	NPC230285
0.8582	High Similarity	NPC118813
0.8582	High Similarity	NPC124269
0.8571	High Similarity	NPC235428
0.8571	High Similarity	NPC87545
0.855	High Similarity	NPC10971
0.855	High Similarity	NPC257756
0.855	High Similarity	NPC129132
0.855	High Similarity	NPC25937
0.855	High Similarity	NPC205468
0.855	High Similarity	NPC87231
0.855	High Similarity	NPC212631
0.854	High Similarity	NPC38219
0.8529	High Similarity	NPC282300
0.8529	High Similarity	NPC14871
0.8529	High Similarity	NPC103362
0.8529	High Similarity	NPC3188
0.8529	High Similarity	NPC90582
0.8529	High Similarity	NPC262094
0.8527	High Similarity	NPC60558
0.8519	High Similarity	NPC329203
0.8519	High Similarity	NPC53181
0.8519	High Similarity	NPC310135
0.8519	High Similarity	NPC20709
0.8519	High Similarity	NPC222342
0.8519	High Similarity	NPC217186
0.8519	High Similarity	NPC225153
0.8519	High Similarity	NPC274784
0.8519	High Similarity	NPC316480
0.8519	High Similarity	NPC265871
0.8519	High Similarity	NPC150648
0.8507	High Similarity	NPC7013
0.8507	High Similarity	NPC332594
0.8507	High Similarity	NPC209560
0.8507	High Similarity	NPC181124
0.8507	High Similarity	NPC162680
0.8507	High Similarity	NPC294409
0.8507	High Similarity	NPC303644
0.8507	High Similarity	NPC212767
0.8507	High Similarity	NPC116632
0.8492	Intermediate Similarity	NPC472888
0.8485	Intermediate Similarity	NPC263670
0.8485	Intermediate Similarity	NPC472365
0.8485	Intermediate Similarity	NPC108113
0.8485	Intermediate Similarity	NPC242294
0.8485	Intermediate Similarity	NPC93756
0.8485	Intermediate Similarity	NPC175098
0.8485	Intermediate Similarity	NPC188646
0.8485	Intermediate Similarity	NPC56031
0.8485	Intermediate Similarity	NPC139813
0.8485	Intermediate Similarity	NPC337373
0.8485	Intermediate Similarity	NPC292998
0.8485	Intermediate Similarity	NPC223457
0.8485	Intermediate Similarity	NPC312318
0.8485	Intermediate Similarity	NPC192304
0.8478	Intermediate Similarity	NPC234629
0.8478	Intermediate Similarity	NPC70136
0.8478	Intermediate Similarity	NPC311741
0.8473	Intermediate Similarity	NPC278556
0.8473	Intermediate Similarity	NPC475008
0.8473	Intermediate Similarity	NPC186097
0.8473	Intermediate Similarity	NPC475009
0.8468	Intermediate Similarity	NPC230951
0.8468	Intermediate Similarity	NPC474874
0.8467	Intermediate Similarity	NPC217083
0.8467	Intermediate Similarity	NPC299080
0.8467	Intermediate Similarity	NPC473042

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 NPC193805 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	450
0.1-0.2	1005
0.2-0.3	1371
0.3-0.4	2708
0.4-0.5	1957
0.5-0.6	1152
0.6-0.7	350
0.7-0.8	121
0.8-0.85	21
0.85-0.9	14
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9262	High Similarity	NPD1203	Approved
0.8934	High Similarity	NPD1547	Clinical (unspecified phase)
0.8862	High Similarity	NPD9717	Approved
0.875	High Similarity	NPD2313	Discontinued
0.8722	High Similarity	NPD1549	Phase 2
0.8647	High Similarity	NPD1552	Clinical (unspecified phase)
0.8647	High Similarity	NPD1550	Clinical (unspecified phase)
0.8636	High Similarity	NPD1510	Phase 2
0.8615	High Similarity	NPD1240	Approved
0.8583	High Similarity	NPD2798	Approved
0.8504	High Similarity	NPD2797	Approved
0.8485	Intermediate Similarity	NPD1607	Approved
0.845	Intermediate Similarity	NPD6832	Phase 2
0.8443	Intermediate Similarity	NPD9493	Approved
0.8433	Intermediate Similarity	NPD1551	Phase 2
0.8406	Intermediate Similarity	NPD1511	Approved
0.837	Intermediate Similarity	NPD2344	Approved
0.8358	Intermediate Similarity	NPD4308	Phase 3
0.8345	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8345	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD3268	Approved
0.8321	Intermediate Similarity	NPD3750	Approved
0.8296	Intermediate Similarity	NPD2796	Approved
0.8286	Intermediate Similarity	NPD1512	Approved
0.8222	Intermediate Similarity	NPD2799	Discontinued
0.8182	Intermediate Similarity	NPD411	Approved
0.8162	Intermediate Similarity	NPD2935	Discontinued
0.814	Intermediate Similarity	NPD3225	Approved
0.8134	Intermediate Similarity	NPD447	Suspended
0.8134	Intermediate Similarity	NPD1933	Approved
0.8129	Intermediate Similarity	NPD2309	Approved
0.8102	Intermediate Similarity	NPD2346	Discontinued
0.8099	Intermediate Similarity	NPD5403	Approved
0.8085	Intermediate Similarity	NPD5401	Approved
0.8083	Intermediate Similarity	NPD74	Approved
0.8083	Intermediate Similarity	NPD9266	Approved
0.8077	Intermediate Similarity	NPD3267	Approved
0.8077	Intermediate Similarity	NPD3266	Approved
0.806	Intermediate Similarity	NPD4307	Phase 2
0.8049	Intermediate Similarity	NPD1241	Discontinued
0.8015	Intermediate Similarity	NPD1019	Discontinued
0.8	Intermediate Similarity	NPD9267	Approved
0.8	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD9263	Approved
0.8	Intermediate Similarity	NPD9264	Approved
0.7956	Intermediate Similarity	NPD3748	Approved
0.7931	Intermediate Similarity	NPD4380	Phase 2
0.7929	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD1201	Approved
0.7891	Intermediate Similarity	NPD2801	Approved
0.7887	Intermediate Similarity	NPD6799	Approved
0.7877	Intermediate Similarity	NPD7411	Suspended
0.7874	Intermediate Similarity	NPD1548	Phase 1
0.7857	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7846	Intermediate Similarity	NPD1481	Phase 2
0.7823	Intermediate Similarity	NPD1934	Approved
0.7803	Intermediate Similarity	NPD1164	Approved
0.7803	Intermediate Similarity	NPD1470	Approved
0.7786	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7769	Intermediate Similarity	NPD1535	Discovery
0.7769	Intermediate Similarity	NPD422	Phase 1
0.774	Intermediate Similarity	NPD3226	Approved
0.7733	Intermediate Similarity	NPD7075	Discontinued
0.7733	Intermediate Similarity	NPD3749	Approved
0.773	Intermediate Similarity	NPD1243	Approved
0.7718	Intermediate Similarity	NPD5402	Approved
0.7718	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD6801	Discontinued
0.7686	Intermediate Similarity	NPD9697	Approved
0.7667	Intermediate Similarity	NPD9261	Approved
0.7667	Intermediate Similarity	NPD3882	Suspended
0.7667	Intermediate Similarity	NPD7768	Phase 2
0.7651	Intermediate Similarity	NPD7819	Suspended
0.7651	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7623	Intermediate Similarity	NPD968	Approved
0.7597	Intermediate Similarity	NPD1894	Discontinued
0.7589	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4661	Approved
0.7586	Intermediate Similarity	NPD4662	Approved
0.7584	Intermediate Similarity	NPD6844	Discontinued
0.7576	Intermediate Similarity	NPD3972	Approved
0.7576	Intermediate Similarity	NPD1608	Approved
0.7571	Intermediate Similarity	NPD7033	Discontinued
0.7569	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD6599	Discontinued
0.7559	Intermediate Similarity	NPD9281	Approved
0.7536	Intermediate Similarity	NPD943	Approved
0.7518	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1610	Phase 2
0.75	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2296	Approved
0.7483	Intermediate Similarity	NPD3817	Phase 2
0.7483	Intermediate Similarity	NPD2800	Approved
0.7466	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD1471	Phase 3
0.7463	Intermediate Similarity	NPD1876	Approved
0.7462	Intermediate Similarity	NPD9545	Approved
0.7452	Intermediate Similarity	NPD3818	Discontinued
0.745	Intermediate Similarity	NPD6585	Discontinued
0.7436	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD5890	Approved
0.74	Intermediate Similarity	NPD5889	Approved
0.7394	Intermediate Similarity	NPD6099	Approved
0.7394	Intermediate Similarity	NPD6100	Approved
0.7391	Intermediate Similarity	NPD6798	Discontinued
0.7391	Intermediate Similarity	NPD3764	Approved
0.7386	Intermediate Similarity	NPD955	Approved
0.7379	Intermediate Similarity	NPD3295	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD920	Approved
0.7348	Intermediate Similarity	NPD17	Approved
0.7338	Intermediate Similarity	NPD520	Approved
0.7329	Intermediate Similarity	NPD7440	Discontinued
0.7325	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7325	Intermediate Similarity	NPD6166	Phase 2
0.7325	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4628	Phase 3
0.731	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7003	Approved
0.7296	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7054	Approved
0.7285	Intermediate Similarity	NPD2366	Approved
0.728	Intermediate Similarity	NPD290	Approved
0.7266	Intermediate Similarity	NPD1296	Phase 2
0.726	Intermediate Similarity	NPD2354	Approved
0.7255	Intermediate Similarity	NPD4288	Approved
0.725	Intermediate Similarity	NPD7472	Approved
0.7244	Intermediate Similarity	NPD6959	Discontinued
0.7234	Intermediate Similarity	NPD1184	Approved
0.7231	Intermediate Similarity	NPD6671	Approved
0.7214	Intermediate Similarity	NPD6233	Phase 2
0.7208	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6797	Phase 2
0.7188	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD6651	Approved
0.7181	Intermediate Similarity	NPD5049	Phase 3
0.7177	Intermediate Similarity	NPD1237	Approved
0.7174	Intermediate Similarity	NPD9494	Approved
0.7163	Intermediate Similarity	NPD3140	Approved
0.7163	Intermediate Similarity	NPD3142	Approved
0.716	Intermediate Similarity	NPD6559	Discontinued
0.716	Intermediate Similarity	NPD7251	Discontinued
0.7153	Intermediate Similarity	NPD5404	Approved
0.7153	Intermediate Similarity	NPD5406	Approved
0.7153	Intermediate Similarity	NPD5405	Approved
0.7153	Intermediate Similarity	NPD5408	Approved
0.7143	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7074	Phase 3
0.7132	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD5535	Approved
0.7131	Intermediate Similarity	NPD1238	Approved
0.7122	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7122	Intermediate Similarity	NPD4908	Phase 1
0.7117	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD7808	Phase 3
0.7117	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD6355	Discontinued
0.7103	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD2353	Approved
0.7099	Intermediate Similarity	NPD5953	Discontinued
0.709	Intermediate Similarity	NPD1778	Approved
0.7081	Intermediate Similarity	NPD7286	Phase 2
0.708	Intermediate Similarity	NPD1283	Approved
0.7078	Intermediate Similarity	NPD1465	Phase 2
0.7071	Intermediate Similarity	NPD4625	Phase 3
0.707	Intermediate Similarity	NPD5494	Approved
0.7067	Intermediate Similarity	NPD6273	Approved
0.705	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD7458	Discontinued
0.7037	Intermediate Similarity	NPD3496	Discontinued
0.7034	Intermediate Similarity	NPD4477	Approved
0.7034	Intermediate Similarity	NPD4476	Approved
0.7021	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1651	Approved
0.7015	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7013	Intermediate Similarity	NPD7577	Discontinued
0.7013	Intermediate Similarity	NPD6279	Approved
0.7013	Intermediate Similarity	NPD6280	Approved
0.7007	Intermediate Similarity	NPD4749	Approved
0.7006	Intermediate Similarity	NPD919	Approved
0.7	Intermediate Similarity	NPD2614	Approved
0.7	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4618	Approved
0.6993	Remote Similarity	NPD4622	Approved
0.6981	Remote Similarity	NPD6232	Discontinued
0.6978	Remote Similarity	NPD5647	Approved
0.6972	Remote Similarity	NPD4062	Phase 3
0.697	Remote Similarity	NPD8313	Approved
0.697	Remote Similarity	NPD8312	Approved
0.6966	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3446	Phase 1
0.6957	Remote Similarity	NPD7473	Discontinued
0.6943	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD2861	Phase 2
0.6929	Remote Similarity	NPD454	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