NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	252.08
Volume:	264.902
LogP:	3.276
LogD:	2.892
LogS:	-3.569
# 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:	0.721
Synthetic Accessibility Score:	1.942
Fsp3:	0.062
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:	-4.72
MDCK Permeability:	2.0643081370508298e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.109
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.627

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.039
Plasma Protein Binding (PPB):	97.16168975830078%
Volume Distribution (VD):	0.436
Pgp-substrate:	1.537392497062683%

ADMET: Metabolism

CYP1A2-inhibitor:	0.973
CYP1A2-substrate:	0.822
CYP2C19-inhibitor:	0.792
CYP2C19-substrate:	0.094
CYP2C9-inhibitor:	0.6
CYP2C9-substrate:	0.931
CYP2D6-inhibitor:	0.554
CYP2D6-substrate:	0.871
CYP3A4-inhibitor:	0.341
CYP3A4-substrate:	0.236

ADMET: Excretion

Clearance (CL):	2.365
Half-life (T1/2):	0.453

ADMET: Toxicity

hERG Blockers:	0.08
Human Hepatotoxicity (H-HT):	0.501
Drug-inuced Liver Injury (DILI):	0.93
AMES Toxicity:	0.514
Rat Oral Acute Toxicity:	0.159
Maximum Recommended Daily Dose:	0.413
Skin Sensitization:	0.485
Carcinogencity:	0.489
Eye Corrosion:	0.01
Eye Irritation:	0.941
Respiratory Toxicity:	0.135

Download Data

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

Natural Product: NPC228661

Natural Product ID:	NPC228661
*Common Name:**	7-Hydroxy-2-Methyl-3-Phenylchromen-4-One
IUPAC Name:	7-hydroxy-2-methyl-3-phenylchromen-4-one
Synonyms:	NSC-108340
Standard InCHIKey:	BBCDTCKKROIGAB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O3/c1-10-15(11-5-3-2-4-6-11)16(18)13-8-7-12(17)9-14(13)19-10/h2-9,17H,1H3
SMILES:	Oc1ccc2c(c1)oc(c(c2=O)c1ccccc1)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489340
PubChem CID:	5380976
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002901] Isoflav-2-enes [CHEMONTID:0000494] Isoflavones

*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
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	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
Others	1
Potency	11

Activity Type	# Activity
Individual Protein	7
Organism	2
Others	1
Uncleic Acid	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	31622.8	nM	PMID[518740]
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	3981.1	nM	PMID[518740]
NPT156	Individual Protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	25118.9	nM	PMID[518740]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[518740]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	32642.7	nM	PMID[518740]
NPT536	Uncleic Acid	microRNA 21	Homo sapiens	Potency	=	13091.8	nM	PMID[518740]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	35481.3	nM	PMID[518740]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2616.9	nM	PMID[518740]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	2078.7	nM	PMID[518740]
NPT7	Individual Protein	Thioredoxin reductase 1, cytoplasmic	Rattus norvegicus	Potency	n.a.	79432.8	nM	PMID[518740]
NPT35	Others	n.a.		LogD7.4	n.a.	2.95	n.a.	PMID[518741]

☑ 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 NPC228661 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	483
0.1-0.2	2028
0.2-0.3	4813
0.3-0.4	12189
0.4-0.5	5323
0.5-0.6	4438
0.6-0.7	5682
0.7-0.8	4271
0.8-0.85	1785
0.85-0.9	1298
0.9-0.95	347
0.95-1	40

Similarity Score	Similarity Level	Natural Product ID
0.9699	High Similarity	NPC266597
0.9699	High Similarity	NPC250266
0.9695	High Similarity	NPC57601
0.963	High Similarity	NPC172986
0.963	High Similarity	NPC270883
0.963	High Similarity	NPC305355
0.963	High Similarity	NPC475680
0.963	High Similarity	NPC261227
0.9627	High Similarity	NPC201395
0.9624	High Similarity	NPC13408
0.9624	High Similarity	NPC124784
0.9624	High Similarity	NPC29353
0.9624	High Similarity	NPC194281
0.9624	High Similarity	NPC234133
0.9624	High Similarity	NPC231772
0.9624	High Similarity	NPC127447
0.9624	High Similarity	NPC473887
0.9624	High Similarity	NPC47815
0.9621	High Similarity	NPC172262
0.9559	High Similarity	NPC205006
0.9559	High Similarity	NPC156590
0.9559	High Similarity	NPC110969
0.9559	High Similarity	NPC118840
0.9559	High Similarity	NPC64908
0.9559	High Similarity	NPC147688
0.9556	High Similarity	NPC96565
0.9556	High Similarity	NPC78913
0.9556	High Similarity	NPC216978
0.9556	High Similarity	NPC301217
0.9556	High Similarity	NPC220062
0.9556	High Similarity	NPC303633
0.9556	High Similarity	NPC18260
0.9556	High Similarity	NPC55018
0.9552	High Similarity	NPC162680
0.9552	High Similarity	NPC7013
0.9552	High Similarity	NPC209560
0.9552	High Similarity	NPC294409
0.9552	High Similarity	NPC181124
0.9552	High Similarity	NPC116632
0.9552	High Similarity	NPC303644
0.9549	High Similarity	NPC239495
0.9549	High Similarity	NPC9985
0.9545	High Similarity	NPC274121
0.9545	High Similarity	NPC50898
0.9545	High Similarity	NPC78540
0.9545	High Similarity	NPC213216
0.9545	High Similarity	NPC292998
0.9493	High Similarity	NPC234629
0.9493	High Similarity	NPC311741
0.9489	High Similarity	NPC11561
0.9489	High Similarity	NPC226636
0.9489	High Similarity	NPC144499
0.9489	High Similarity	NPC473042
0.9489	High Similarity	NPC202981
0.9485	High Similarity	NPC269652
0.9485	High Similarity	NPC241100
0.9485	High Similarity	NPC281207
0.9485	High Similarity	NPC69769
0.9485	High Similarity	NPC159275
0.9485	High Similarity	NPC235239
0.9481	High Similarity	NPC99333
0.9481	High Similarity	NPC309154
0.9481	High Similarity	NPC90665
0.9481	High Similarity	NPC12175
0.9481	High Similarity	NPC55162
0.9481	High Similarity	NPC124269
0.9481	High Similarity	NPC280284
0.9481	High Similarity	NPC278323
0.9481	High Similarity	NPC279668
0.9481	High Similarity	NPC188947
0.9478	High Similarity	NPC240593
0.942	High Similarity	NPC9117
0.942	High Similarity	NPC166138
0.942	High Similarity	NPC219915
0.942	High Similarity	NPC24821
0.942	High Similarity	NPC106985
0.942	High Similarity	NPC190637
0.942	High Similarity	NPC11700
0.942	High Similarity	NPC38219
0.942	High Similarity	NPC212932
0.942	High Similarity	NPC293053
0.942	High Similarity	NPC18585
0.9416	High Similarity	NPC103362
0.9416	High Similarity	NPC3188
0.9416	High Similarity	NPC136840
0.9416	High Similarity	NPC282300
0.9412	High Similarity	NPC217186
0.9412	High Similarity	NPC143799
0.9412	High Similarity	NPC152042
0.9412	High Similarity	NPC265871
0.9412	High Similarity	NPC274784
0.9412	High Similarity	NPC150648
0.9412	High Similarity	NPC261234
0.9412	High Similarity	NPC295384
0.9412	High Similarity	NPC241838
0.9412	High Similarity	NPC329203
0.9412	High Similarity	NPC222342
0.9412	High Similarity	NPC53181
0.9412	High Similarity	NPC310135
0.9412	High Similarity	NPC225153
0.9412	High Similarity	NPC20709
0.9407	High Similarity	NPC476480
0.9407	High Similarity	NPC275055
0.9407	High Similarity	NPC290291
0.9407	High Similarity	NPC188879
0.9407	High Similarity	NPC84585
0.9407	High Similarity	NPC299379
0.9403	High Similarity	NPC151113
0.9403	High Similarity	NPC234560
0.9403	High Similarity	NPC39426
0.9394	High Similarity	NPC113006
0.9394	High Similarity	NPC64359
0.9394	High Similarity	NPC284424
0.9394	High Similarity	NPC313618
0.9394	High Similarity	NPC308037
0.9389	High Similarity	NPC39753
0.9389	High Similarity	NPC115998
0.9357	High Similarity	NPC237635
0.9357	High Similarity	NPC79469
0.9357	High Similarity	NPC24673
0.9357	High Similarity	NPC97716
0.9357	High Similarity	NPC104406
0.9357	High Similarity	NPC201731
0.9353	High Similarity	NPC273538
0.9353	High Similarity	NPC303185
0.9353	High Similarity	NPC216538
0.9353	High Similarity	NPC326500
0.9353	High Similarity	NPC184649
0.9348	High Similarity	NPC78803
0.9348	High Similarity	NPC62840
0.9348	High Similarity	NPC214236
0.9348	High Similarity	NPC1534
0.9348	High Similarity	NPC293852
0.9348	High Similarity	NPC299080
0.9348	High Similarity	NPC217083
0.9348	High Similarity	NPC200694
0.9348	High Similarity	NPC59739
0.9343	High Similarity	NPC6407
0.9343	High Similarity	NPC188243
0.9343	High Similarity	NPC284550
0.9343	High Similarity	NPC213659
0.9343	High Similarity	NPC230285
0.9343	High Similarity	NPC101366
0.9343	High Similarity	NPC326109
0.9343	High Similarity	NPC204985
0.9343	High Similarity	NPC76445
0.9343	High Similarity	NPC48624
0.9343	High Similarity	NPC184536
0.9343	High Similarity	NPC215311
0.9343	High Similarity	NPC172250
0.9343	High Similarity	NPC103342
0.9343	High Similarity	NPC103904
0.9343	High Similarity	NPC129853
0.9343	High Similarity	NPC110228
0.9343	High Similarity	NPC144118
0.9343	High Similarity	NPC146679
0.9343	High Similarity	NPC80962
0.9343	High Similarity	NPC259166
0.9343	High Similarity	NPC59951
0.9343	High Similarity	NPC219917
0.9343	High Similarity	NPC150522
0.9338	High Similarity	NPC472460
0.9338	High Similarity	NPC329225
0.9338	High Similarity	NPC118813
0.9338	High Similarity	NPC147686
0.9333	High Similarity	NPC281917
0.9333	High Similarity	NPC216361
0.9333	High Similarity	NPC235428
0.9333	High Similarity	NPC187432
0.9333	High Similarity	NPC256042
0.9333	High Similarity	NPC87545
0.9333	High Similarity	NPC116775
0.9333	High Similarity	NPC254741
0.9328	High Similarity	NPC286336
0.9323	High Similarity	NPC10971
0.9323	High Similarity	NPC205468
0.9323	High Similarity	NPC257756
0.9323	High Similarity	NPC212631
0.9323	High Similarity	NPC129132
0.9323	High Similarity	NPC87231
0.9318	High Similarity	NPC5515
0.9318	High Similarity	NPC270369
0.9318	High Similarity	NPC137264
0.9313	High Similarity	NPC197425
0.9291	High Similarity	NPC272194
0.9291	High Similarity	NPC266572
0.9291	High Similarity	NPC168085
0.9291	High Similarity	NPC6511
0.9286	High Similarity	NPC477955
0.9286	High Similarity	NPC5820
0.9286	High Similarity	NPC196114
0.9286	High Similarity	NPC306488
0.9286	High Similarity	NPC178343
0.9286	High Similarity	NPC124729
0.9286	High Similarity	NPC299011
0.9286	High Similarity	NPC154217
0.9281	High Similarity	NPC68104
0.9281	High Similarity	NPC75049
0.9281	High Similarity	NPC149026
0.9281	High Similarity	NPC257097

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 NPC228661 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	469
0.1-0.2	1001
0.2-0.3	1509
0.3-0.4	2717
0.4-0.5	1851
0.5-0.6	1095
0.6-0.7	332
0.7-0.8	113
0.8-0.85	34
0.85-0.9	22
0.9-0.95	6
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9403	High Similarity	NPD1510	Phase 2
0.9394	High Similarity	NPD1240	Approved
0.9353	High Similarity	NPD4378	Clinical (unspecified phase)
0.9338	High Similarity	NPD1549	Phase 2
0.9333	High Similarity	NPD2796	Approved
0.9265	High Similarity	NPD1550	Clinical (unspecified phase)
0.9265	High Similarity	NPD1552	Clinical (unspecified phase)
0.9254	High Similarity	NPD1607	Approved
0.9214	High Similarity	NPD7410	Clinical (unspecified phase)
0.9007	High Similarity	NPD1511	Approved
0.8929	High Similarity	NPD3750	Approved
0.8881	High Similarity	NPD1512	Approved
0.8776	High Similarity	NPD1934	Approved
0.8767	High Similarity	NPD4380	Phase 2
0.8716	High Similarity	NPD2801	Approved
0.8716	High Similarity	NPD2393	Clinical (unspecified phase)
0.8707	High Similarity	NPD7411	Suspended
0.8667	High Similarity	NPD4381	Clinical (unspecified phase)
0.8667	High Similarity	NPD7075	Discontinued
0.8658	High Similarity	NPD8443	Clinical (unspecified phase)
0.8611	High Similarity	NPD6799	Approved
0.8592	High Similarity	NPD1243	Approved
0.8591	High Similarity	NPD7819	Suspended
0.8591	High Similarity	NPD7096	Clinical (unspecified phase)
0.8582	High Similarity	NPD2344	Approved
0.8571	High Similarity	NPD3748	Approved
0.8543	High Similarity	NPD3749	Approved
0.8523	High Similarity	NPD6801	Discontinued
0.8521	High Similarity	NPD970	Clinical (unspecified phase)
0.8511	High Similarity	NPD1551	Phase 2
0.8477	Intermediate Similarity	NPD3882	Suspended
0.8462	Intermediate Similarity	NPD2800	Approved
0.8389	Intermediate Similarity	NPD6599	Discontinued
0.8355	Intermediate Similarity	NPD7768	Phase 2
0.8345	Intermediate Similarity	NPD2309	Approved
0.8333	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8309	Intermediate Similarity	NPD1203	Approved
0.8289	Intermediate Similarity	NPD3817	Phase 2
0.8288	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8273	Intermediate Similarity	NPD2313	Discontinued
0.8273	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8248	Intermediate Similarity	NPD2798	Approved
0.8228	Intermediate Similarity	NPD3818	Discontinued
0.8217	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8217	Intermediate Similarity	NPD6166	Phase 2
0.8217	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8188	Intermediate Similarity	NPD920	Approved
0.8188	Intermediate Similarity	NPD5403	Approved
0.8182	Intermediate Similarity	NPD2799	Discontinued
0.8176	Intermediate Similarity	NPD5401	Approved
0.8176	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8156	Intermediate Similarity	NPD943	Approved
0.8148	Intermediate Similarity	NPD422	Phase 1
0.8148	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD6959	Discontinued
0.8125	Intermediate Similarity	NPD6099	Approved
0.8125	Intermediate Similarity	NPD6100	Approved
0.8125	Intermediate Similarity	NPD2935	Discontinued
0.812	Intermediate Similarity	NPD1548	Phase 1
0.8088	Intermediate Similarity	NPD9717	Approved
0.8063	Intermediate Similarity	NPD7054	Approved
0.8056	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.8056	Intermediate Similarity	NPD4308	Phase 3
0.8043	Intermediate Similarity	NPD2797	Approved
0.8042	Intermediate Similarity	NPD6651	Approved
0.8015	Intermediate Similarity	NPD1610	Phase 2
0.8014	Intermediate Similarity	NPD3268	Approved
0.8012	Intermediate Similarity	NPD7074	Phase 3
0.8012	Intermediate Similarity	NPD7472	Approved
0.8	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD5953	Discontinued
0.7963	Intermediate Similarity	NPD6797	Phase 2
0.7962	Intermediate Similarity	NPD5494	Approved
0.7961	Intermediate Similarity	NPD3226	Approved
0.7935	Intermediate Similarity	NPD5402	Approved
0.7914	Intermediate Similarity	NPD7251	Discontinued
0.7905	Intermediate Similarity	NPD4628	Phase 3
0.7872	Intermediate Similarity	NPD6832	Phase 2
0.7872	Intermediate Similarity	NPD4908	Phase 1
0.7866	Intermediate Similarity	NPD7808	Phase 3
0.7862	Intermediate Similarity	NPD6232	Discontinued
0.7842	Intermediate Similarity	NPD3225	Approved
0.784	Intermediate Similarity	NPD7286	Phase 2
0.7826	Intermediate Similarity	NPD7473	Discontinued
0.7826	Intermediate Similarity	NPD1608	Approved
0.7823	Intermediate Similarity	NPD2346	Discontinued
0.7821	Intermediate Similarity	NPD4288	Approved
0.7815	Intermediate Similarity	NPD2533	Approved
0.7815	Intermediate Similarity	NPD2532	Approved
0.7815	Intermediate Similarity	NPD2534	Approved
0.7808	Intermediate Similarity	NPD7033	Discontinued
0.7805	Intermediate Similarity	NPD6559	Discontinued
0.7786	Intermediate Similarity	NPD3266	Approved
0.7786	Intermediate Similarity	NPD3267	Approved
0.7785	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD919	Approved
0.7778	Intermediate Similarity	NPD4307	Phase 2
0.7762	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7758	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD1465	Phase 2
0.7721	Intermediate Similarity	NPD9545	Approved
0.7707	Intermediate Similarity	NPD2296	Approved
0.7704	Intermediate Similarity	NPD9493	Approved
0.7702	Intermediate Similarity	NPD3926	Phase 2
0.7698	Intermediate Similarity	NPD3972	Approved
0.7688	Intermediate Similarity	NPD1247	Approved
0.7639	Intermediate Similarity	NPD1296	Phase 2
0.7639	Intermediate Similarity	NPD3764	Approved
0.7639	Intermediate Similarity	NPD411	Approved
0.7632	Intermediate Similarity	NPD7390	Discontinued
0.7626	Intermediate Similarity	NPD1201	Approved
0.7622	Intermediate Similarity	NPD5844	Phase 1
0.7622	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7612	Intermediate Similarity	NPD1241	Discontinued
0.7609	Intermediate Similarity	NPD17	Approved
0.7603	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD447	Suspended
0.7603	Intermediate Similarity	NPD1933	Approved
0.76	Intermediate Similarity	NPD2654	Approved
0.7597	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7569	Intermediate Similarity	NPD4625	Phase 3
0.7552	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7535	Intermediate Similarity	NPD1164	Approved
0.7535	Intermediate Similarity	NPD1470	Approved
0.753	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7518	Intermediate Similarity	NPD4749	Approved
0.7514	Intermediate Similarity	NPD4363	Phase 3
0.7514	Intermediate Similarity	NPD4360	Phase 2
0.7485	Intermediate Similarity	NPD4287	Approved
0.7483	Intermediate Similarity	NPD230	Phase 1
0.7471	Intermediate Similarity	NPD4361	Phase 2
0.7471	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.747	Intermediate Similarity	NPD1729	Discontinued
0.7467	Intermediate Similarity	NPD1471	Phase 3
0.7465	Intermediate Similarity	NPD1876	Approved
0.745	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD1613	Approved
0.7386	Intermediate Similarity	NPD2354	Approved
0.7365	Intermediate Similarity	NPD5124	Phase 1
0.7365	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD1019	Discontinued
0.7355	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD5940	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1481	Phase 2
0.732	Intermediate Similarity	NPD7003	Approved
0.7296	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD5408	Approved
0.7285	Intermediate Similarity	NPD5404	Approved
0.7285	Intermediate Similarity	NPD5405	Approved
0.7285	Intermediate Similarity	NPD5406	Approved
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7278	Intermediate Similarity	NPD7458	Discontinued
0.7278	Intermediate Similarity	NPD6104	Discontinued
0.726	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD1535	Discovery
0.725	Intermediate Similarity	NPD6279	Approved
0.725	Intermediate Similarity	NPD6280	Approved
0.725	Intermediate Similarity	NPD6844	Discontinued
0.7246	Intermediate Similarity	NPD3751	Discontinued
0.7244	Intermediate Similarity	NPD4661	Approved
0.7244	Intermediate Similarity	NPD4662	Approved
0.7239	Intermediate Similarity	NPD74	Approved
0.7239	Intermediate Similarity	NPD9266	Approved
0.7237	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD2353	Approved
0.7233	Intermediate Similarity	NPD6585	Discontinued
0.7229	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD1894	Discontinued
0.7212	Intermediate Similarity	NPD5711	Approved
0.7212	Intermediate Similarity	NPD5710	Approved
0.7207	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2861	Phase 2
0.7192	Intermediate Similarity	NPD9494	Approved
0.7188	Intermediate Similarity	NPD5890	Approved
0.7188	Intermediate Similarity	NPD5889	Approved
0.7181	Intermediate Similarity	NPD3140	Approved
0.7181	Intermediate Similarity	NPD3142	Approved
0.7178	Intermediate Similarity	NPD6971	Discontinued
0.717	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9267	Approved
0.7164	Intermediate Similarity	NPD9263	Approved
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9264	Approved
0.7163	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7584	Approved
0.7152	Intermediate Similarity	NPD7199	Phase 2
0.7143	Intermediate Similarity	NPD7577	Discontinued
0.7134	Intermediate Similarity	NPD7447	Phase 1
0.7133	Intermediate Similarity	NPD6355	Discontinued
0.7126	Intermediate Similarity	NPD2403	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