NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	436.19
Volume:	458.959
LogP:	5.772
LogD:	4.036
LogS:	-3.544
# Rotatable Bonds:	7
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.226
Synthetic Accessibility Score:	3.597
Fsp3:	0.269
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.948
MDCK Permeability:	1.7860123989521526e-05
Pgp-inhibitor:	0.656
Pgp-substrate:	0.005
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.016
30% Bioavailability (F30%):	0.023

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003
Plasma Protein Binding (PPB):	101.1530990600586%
Volume Distribution (VD):	0.584
Pgp-substrate:	2.169116973876953%

ADMET: Metabolism

CYP1A2-inhibitor:	0.871
CYP1A2-substrate:	0.446
CYP2C19-inhibitor:	0.728
CYP2C19-substrate:	0.156
CYP2C9-inhibitor:	0.82
CYP2C9-substrate:	0.936
CYP2D6-inhibitor:	0.931
CYP2D6-substrate:	0.414
CYP3A4-inhibitor:	0.797
CYP3A4-substrate:	0.21

ADMET: Excretion

Clearance (CL):	11.359
Half-life (T1/2):	0.65

ADMET: Toxicity

hERG Blockers:	0.132
Human Hepatotoxicity (H-HT):	0.798
Drug-inuced Liver Injury (DILI):	0.178
AMES Toxicity:	0.104
Rat Oral Acute Toxicity:	0.769
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.948
Carcinogencity:	0.763
Eye Corrosion:	0.003
Eye Irritation:	0.651
Respiratory Toxicity:	0.884

Download Data

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

Natural Product: NPC476981

Natural Product ID:	NPC476981
*Common Name:**	(E)-1-[2-Methyl-2-(4-methyl-3-pentenyl)-5-hydroxy-8-methoxy-2H-1-benzopyran-6-yl]-3-(2,5-dihydroxyphenyl)-2-propene-1-one
IUPAC Name:	(E)-3-(2,5-dihydroxyphenyl)-1-[5-hydroxy-8-methoxy-2-methyl-2-(4-methylpent-3-enyl)chromen-6-yl]prop-2-en-1-one
Synonyms:
Standard InCHIKey:	VSHVGAUGDJWOFM-VQHVLOKHSA-N
Standard InCHI:	InChI=1S/C26H28O6/c1-16(2)6-5-12-26(3)13-11-19-24(30)20(15-23(31-4)25(19)32-26)22(29)9-7-17-14-18(27)8-10-21(17)28/h6-11,13-15,27-28,30H,5,12H2,1-4H3/b9-7+
SMILES:	CC(=CCCC1(C=CC2=C(C(=CC(=C2O1)OC)C(=O)/C=C/C3=C(C=CC(=C3)O)O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	122185280
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003467] Linear 1,3-diarylpropanoids [CHEMONTID:0001630] Chalcones and dihydrochalcones [CHEMONTID:0003472] 2'-Hydroxychalcones

*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
NPO33641	Desmodium congestum	Species	Fabaceae	Eukaryota	whole plant	tropical rainforest surrounding villages near Bintulu, Sarawak, Malaysia	2014-SEP	PMID[26284978]

☑ 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
MIC	7

Activity Type	# Activity
Cell Line	1
Organism	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT71	Cell Line	HEK293	Homo sapiens	IC50	=	21000	nM	PMID[26284978]
NPT1118	Organism	Streptococcus pneumoniae	Streptococcus pneumoniae	MIC	=	32	ug/ml	PMID[26284978]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32	ug/ml	PMID[26284978]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	32	ug/ml	PMID[26284978]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	=	16	ug/ml	PMID[26284978]
NPT1531	Organism	Enterococcus faecium	Enterococcus faecium	MIC	=	32	ug/ml	PMID[26284978]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	32	ug/ml	PMID[26284978]

☑ 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 NPC476981 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	422
0.1-0.2	1719
0.2-0.3	4396
0.3-0.4	10564
0.4-0.5	7250
0.5-0.6	3349
0.6-0.7	4887
0.7-0.8	5431
0.8-0.85	2409
0.85-0.9	1647
0.9-0.95	598
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9868	High Similarity	NPC476980
0.9739	High Similarity	NPC472448
0.9739	High Similarity	NPC83922
0.9673	High Similarity	NPC167678
0.9673	High Similarity	NPC29876
0.9673	High Similarity	NPC259456
0.9673	High Similarity	NPC258331
0.9669	High Similarity	NPC472455
0.9667	High Similarity	NPC280937
0.9664	High Similarity	NPC226973
0.9664	High Similarity	NPC208043
0.9664	High Similarity	NPC308451
0.961	High Similarity	NPC261470
0.961	High Similarity	NPC229632
0.9608	High Similarity	NPC204290
0.9605	High Similarity	NPC36852
0.9605	High Similarity	NPC262286
0.9605	High Similarity	NPC78225
0.9603	High Similarity	NPC256612
0.9603	High Similarity	NPC20830
0.9603	High Similarity	NPC472280
0.9603	High Similarity	NPC234255
0.9597	High Similarity	NPC306821
0.9545	High Similarity	NPC40037
0.9542	High Similarity	NPC204879
0.9539	High Similarity	NPC138243
0.9539	High Similarity	NPC191146
0.9539	High Similarity	NPC68093
0.9536	High Similarity	NPC86485
0.9536	High Similarity	NPC274327
0.9536	High Similarity	NPC47781
0.9536	High Similarity	NPC69394
0.9536	High Similarity	NPC231018
0.9536	High Similarity	NPC255350
0.9536	High Similarity	NPC176775
0.9536	High Similarity	NPC472408
0.9536	High Similarity	NPC22519
0.9536	High Similarity	NPC472915
0.9536	High Similarity	NPC183878
0.9536	High Similarity	NPC145379
0.9536	High Similarity	NPC160951
0.9533	High Similarity	NPC149614
0.9533	High Similarity	NPC117579
0.9533	High Similarity	NPC262623
0.953	High Similarity	NPC328119
0.9487	High Similarity	NPC275780
0.9487	High Similarity	NPC50960
0.9487	High Similarity	NPC239752
0.9487	High Similarity	NPC472450
0.9484	High Similarity	NPC81679
0.9481	High Similarity	NPC246478
0.9477	High Similarity	NPC181960
0.9477	High Similarity	NPC217677
0.9477	High Similarity	NPC473272
0.9477	High Similarity	NPC474681
0.9477	High Similarity	NPC284820
0.9477	High Similarity	NPC218313
0.9477	High Similarity	NPC165977
0.9474	High Similarity	NPC163780
0.9474	High Similarity	NPC117992
0.9474	High Similarity	NPC113906
0.9474	High Similarity	NPC230149
0.9474	High Similarity	NPC39184
0.9474	High Similarity	NPC50715
0.9474	High Similarity	NPC167815
0.9474	High Similarity	NPC472909
0.9474	High Similarity	NPC134287
0.9474	High Similarity	NPC201136
0.9474	High Similarity	NPC227325
0.9474	High Similarity	NPC130589
0.9474	High Similarity	NPC213622
0.9474	High Similarity	NPC37392
0.9474	High Similarity	NPC208197
0.9474	High Similarity	NPC57674
0.9474	High Similarity	NPC2476
0.9474	High Similarity	NPC146165
0.9474	High Similarity	NPC256925
0.9474	High Similarity	NPC4455
0.9474	High Similarity	NPC280339
0.9474	High Similarity	NPC138360
0.9474	High Similarity	NPC92659
0.9474	High Similarity	NPC152951
0.9474	High Similarity	NPC196439
0.9474	High Similarity	NPC32557
0.9474	High Similarity	NPC168247
0.9474	High Similarity	NPC183597
0.9474	High Similarity	NPC189960
0.9474	High Similarity	NPC128863
0.947	High Similarity	NPC275722
0.947	High Similarity	NPC301323
0.947	High Similarity	NPC83508
0.947	High Similarity	NPC162313
0.947	High Similarity	NPC275836
0.947	High Similarity	NPC166201
0.947	High Similarity	NPC256283
0.947	High Similarity	NPC471982
0.947	High Similarity	NPC60972
0.947	High Similarity	NPC237994
0.947	High Similarity	NPC25270
0.947	High Similarity	NPC241498
0.947	High Similarity	NPC131624
0.947	High Similarity	NPC198826
0.947	High Similarity	NPC39732
0.947	High Similarity	NPC239128
0.947	High Similarity	NPC120163
0.947	High Similarity	NPC100887
0.947	High Similarity	NPC187498
0.947	High Similarity	NPC301123
0.947	High Similarity	NPC293183
0.947	High Similarity	NPC71334
0.947	High Similarity	NPC212678
0.947	High Similarity	NPC188203
0.947	High Similarity	NPC57030
0.947	High Similarity	NPC156222
0.947	High Similarity	NPC222830
0.9467	High Similarity	NPC179183
0.9467	High Similarity	NPC239363
0.9467	High Similarity	NPC156953
0.9463	High Similarity	NPC195202
0.9427	High Similarity	NPC39091
0.9427	High Similarity	NPC120593
0.9423	High Similarity	NPC23298
0.9423	High Similarity	NPC189473
0.9423	High Similarity	NPC306321
0.9423	High Similarity	NPC303460
0.9419	High Similarity	NPC66288
0.9419	High Similarity	NPC266314
0.9419	High Similarity	NPC474187
0.9419	High Similarity	NPC61010
0.9416	High Similarity	NPC250214
0.9416	High Similarity	NPC152904
0.9416	High Similarity	NPC95936
0.9416	High Similarity	NPC184755
0.9416	High Similarity	NPC74178
0.9412	High Similarity	NPC178854
0.9412	High Similarity	NPC276444
0.9412	High Similarity	NPC133970
0.9412	High Similarity	NPC6633
0.9412	High Similarity	NPC472916
0.9412	High Similarity	NPC5322
0.9412	High Similarity	NPC49824
0.9412	High Similarity	NPC471985
0.9408	High Similarity	NPC128961
0.9408	High Similarity	NPC250822
0.9408	High Similarity	NPC49402
0.9408	High Similarity	NPC206238
0.9408	High Similarity	NPC70433
0.9408	High Similarity	NPC75279
0.9408	High Similarity	NPC88645
0.9408	High Similarity	NPC33051
0.9408	High Similarity	NPC167091
0.9408	High Similarity	NPC292214
0.9408	High Similarity	NPC227337
0.9408	High Similarity	NPC271779
0.9408	High Similarity	NPC273462
0.9408	High Similarity	NPC276409
0.9408	High Similarity	NPC124714
0.9404	High Similarity	NPC154345
0.94	High Similarity	NPC266499
0.9396	High Similarity	NPC93034
0.9396	High Similarity	NPC62536
0.9396	High Similarity	NPC12200
0.9396	High Similarity	NPC119660
0.9396	High Similarity	NPC33265
0.9396	High Similarity	NPC205522
0.9359	High Similarity	NPC329760
0.9359	High Similarity	NPC474162
0.9359	High Similarity	NPC474150
0.9355	High Similarity	NPC228785
0.9355	High Similarity	NPC328102
0.9355	High Similarity	NPC474287
0.9355	High Similarity	NPC475784
0.9355	High Similarity	NPC119209
0.9355	High Similarity	NPC14353
0.9355	High Similarity	NPC118256
0.9355	High Similarity	NPC192686
0.9355	High Similarity	NPC475886
0.9355	High Similarity	NPC56085
0.9351	High Similarity	NPC210084
0.9351	High Similarity	NPC475267
0.9351	High Similarity	NPC78103
0.9351	High Similarity	NPC93376
0.9351	High Similarity	NPC470402
0.9351	High Similarity	NPC110070
0.9351	High Similarity	NPC227192
0.9351	High Similarity	NPC203891
0.9351	High Similarity	NPC472910
0.9351	High Similarity	NPC474208
0.9351	High Similarity	NPC291508
0.9351	High Similarity	NPC75215
0.9351	High Similarity	NPC224137
0.9351	High Similarity	NPC474836
0.9351	High Similarity	NPC101830
0.9351	High Similarity	NPC52889
0.9351	High Similarity	NPC96167
0.9351	High Similarity	NPC472914
0.9351	High Similarity	NPC245758
0.9351	High Similarity	NPC223787
0.9351	High Similarity	NPC99597
0.9351	High Similarity	NPC472911

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 NPC476981 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	380
0.1-0.2	992
0.2-0.3	1726
0.3-0.4	2636
0.4-0.5	1773
0.5-0.6	995
0.6-0.7	443
0.7-0.8	152
0.8-0.85	31
0.85-0.9	17
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9536	High Similarity	NPD2801	Approved
0.9156	High Similarity	NPD2393	Clinical (unspecified phase)
0.9091	High Similarity	NPD1934	Approved
0.9007	High Similarity	NPD4378	Clinical (unspecified phase)
0.8987	High Similarity	NPD5494	Approved
0.894	High Similarity	NPD1511	Approved
0.8917	High Similarity	NPD3882	Suspended
0.8824	High Similarity	NPD1512	Approved
0.8773	High Similarity	NPD3818	Discontinued
0.8758	High Similarity	NPD7410	Clinical (unspecified phase)
0.8734	High Similarity	NPD3817	Phase 2
0.8718	High Similarity	NPD4380	Phase 2
0.865	High Similarity	NPD6168	Clinical (unspecified phase)
0.865	High Similarity	NPD6166	Phase 2
0.865	High Similarity	NPD6167	Clinical (unspecified phase)
0.8642	High Similarity	NPD6232	Discontinued
0.8598	High Similarity	NPD7473	Discontinued
0.858	High Similarity	NPD1247	Approved
0.8533	High Similarity	NPD1510	Phase 2
0.8512	High Similarity	NPD4338	Clinical (unspecified phase)
0.8509	High Similarity	NPD7075	Discontinued
0.8494	Intermediate Similarity	NPD5844	Phase 1
0.8494	Intermediate Similarity	NPD7054	Approved
0.8487	Intermediate Similarity	NPD1549	Phase 2
0.8477	Intermediate Similarity	NPD2796	Approved
0.8447	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD7472	Approved
0.8443	Intermediate Similarity	NPD7074	Phase 3
0.8438	Intermediate Similarity	NPD7819	Suspended
0.8438	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8421	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8389	Intermediate Similarity	NPD1240	Approved
0.8375	Intermediate Similarity	NPD6801	Discontinued
0.8355	Intermediate Similarity	NPD2935	Discontinued
0.8313	Intermediate Similarity	NPD7411	Suspended
0.8294	Intermediate Similarity	NPD7808	Phase 3
0.8284	Intermediate Similarity	NPD6797	Phase 2
0.8278	Intermediate Similarity	NPD1607	Approved
0.8272	Intermediate Similarity	NPD5402	Approved
0.8272	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD7251	Discontinued
0.8232	Intermediate Similarity	NPD919	Approved
0.8217	Intermediate Similarity	NPD6799	Approved
0.8166	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD943	Approved
0.8144	Intermediate Similarity	NPD3926	Phase 2
0.8133	Intermediate Similarity	NPD6959	Discontinued
0.8098	Intermediate Similarity	NPD1465	Phase 2
0.8077	Intermediate Similarity	NPD2800	Approved
0.8025	Intermediate Similarity	NPD3750	Approved
0.8025	Intermediate Similarity	NPD6599	Discontinued
0.8023	Intermediate Similarity	NPD6559	Discontinued
0.8013	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7768	Phase 2
0.7988	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD447	Suspended
0.7965	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7962	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD3749	Approved
0.795	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD920	Approved
0.7937	Intermediate Similarity	NPD2532	Approved
0.7937	Intermediate Similarity	NPD2533	Approved
0.7937	Intermediate Similarity	NPD2534	Approved
0.7895	Intermediate Similarity	NPD2313	Discontinued
0.7853	Intermediate Similarity	NPD3226	Approved
0.7848	Intermediate Similarity	NPD1243	Approved
0.784	Intermediate Similarity	NPD5403	Approved
0.7826	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7821	Intermediate Similarity	NPD2799	Discontinued
0.7821	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7814	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7809	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD1551	Phase 2
0.7763	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7759	Intermediate Similarity	NPD5953	Discontinued
0.7746	Intermediate Similarity	NPD7286	Phase 2
0.7742	Intermediate Similarity	NPD230	Phase 1
0.7722	Intermediate Similarity	NPD2344	Approved
0.7722	Intermediate Similarity	NPD2346	Discontinued
0.7722	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD5401	Approved
0.7707	Intermediate Similarity	NPD3748	Approved
0.7702	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6651	Approved
0.7688	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD1613	Approved
0.7677	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD6100	Approved
0.7658	Intermediate Similarity	NPD6099	Approved
0.7654	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1933	Approved
0.7597	Intermediate Similarity	NPD3027	Phase 3
0.7595	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3751	Discontinued
0.7578	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD4628	Phase 3
0.7576	Intermediate Similarity	NPD1653	Approved
0.7546	Intermediate Similarity	NPD7390	Discontinued
0.7542	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD2309	Approved
0.7531	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD37	Approved
0.75	Intermediate Similarity	NPD7199	Phase 2
0.7485	Intermediate Similarity	NPD6234	Discontinued
0.7471	Intermediate Similarity	NPD4965	Approved
0.7471	Intermediate Similarity	NPD4967	Phase 2
0.7471	Intermediate Similarity	NPD4966	Approved
0.7468	Intermediate Similarity	NPD9494	Approved
0.7457	Intermediate Similarity	NPD3787	Discontinued
0.7451	Intermediate Similarity	NPD1203	Approved
0.7436	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7434	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7414	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD5242	Approved
0.7403	Intermediate Similarity	NPD8434	Phase 2
0.7403	Intermediate Similarity	NPD2798	Approved
0.7396	Intermediate Similarity	NPD6844	Discontinued
0.7375	Intermediate Similarity	NPD4308	Phase 3
0.7375	Intermediate Similarity	NPD7033	Discontinued
0.7372	Intermediate Similarity	NPD4625	Phase 3
0.7366	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD5711	Approved
0.7356	Intermediate Similarity	NPD5710	Approved
0.7351	Intermediate Similarity	NPD4363	Phase 3
0.7351	Intermediate Similarity	NPD4360	Phase 2
0.7333	Intermediate Similarity	NPD8313	Approved
0.7333	Intermediate Similarity	NPD8312	Approved
0.7325	Intermediate Similarity	NPD3268	Approved
0.7318	Intermediate Similarity	NPD7685	Pre-registration
0.7316	Intermediate Similarity	NPD7435	Discontinued
0.7316	Intermediate Similarity	NPD7696	Phase 3
0.7316	Intermediate Similarity	NPD7697	Approved
0.7316	Intermediate Similarity	NPD7698	Approved
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7308	Intermediate Similarity	NPD6832	Phase 2
0.7308	Intermediate Similarity	NPD4908	Phase 1
0.7303	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD7584	Approved
0.7278	Intermediate Similarity	NPD7549	Discontinued
0.7277	Intermediate Similarity	NPD7871	Phase 2
0.7277	Intermediate Similarity	NPD7870	Phase 2
0.7273	Intermediate Similarity	NPD2403	Approved
0.7267	Intermediate Similarity	NPD1548	Phase 1
0.7257	Intermediate Similarity	NPD7229	Phase 3
0.7255	Intermediate Similarity	NPD9717	Approved
0.7235	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6386	Approved
0.7235	Intermediate Similarity	NPD6385	Approved
0.7229	Intermediate Similarity	NPD4357	Discontinued
0.7226	Intermediate Similarity	NPD1470	Approved
0.7226	Intermediate Similarity	NPD2797	Approved
0.7219	Intermediate Similarity	NPD4361	Phase 2
0.7219	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7458	Discontinued
0.7209	Intermediate Similarity	NPD5353	Approved
0.72	Intermediate Similarity	NPD5536	Phase 2
0.7191	Intermediate Similarity	NPD7228	Approved
0.719	Intermediate Similarity	NPD422	Phase 1
0.719	Intermediate Similarity	NPD1610	Phase 2
0.7188	Intermediate Similarity	NPD5124	Phase 1
0.7188	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD6823	Phase 2
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.7143	Intermediate Similarity	NPD1608	Approved
0.7143	Intermediate Similarity	NPD7783	Phase 2
0.7143	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD9269	Phase 2
0.7134	Intermediate Similarity	NPD2424	Discontinued
0.7134	Intermediate Similarity	NPD2861	Phase 2
0.7134	Intermediate Similarity	NPD3018	Phase 2
0.7128	Intermediate Similarity	NPD8151	Discontinued
0.7125	Intermediate Similarity	NPD4307	Phase 2
0.7118	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5404	Approved
0.7117	Intermediate Similarity	NPD5406	Approved
0.7117	Intermediate Similarity	NPD5405	Approved
0.7117	Intermediate Similarity	NPD5408	Approved
0.7111	Intermediate Similarity	NPD1729	Discontinued
0.711	Intermediate Similarity	NPD4288	Approved
0.7107	Intermediate Similarity	NPD411	Approved
0.7107	Intermediate Similarity	NPD3764	Approved
0.7105	Intermediate Similarity	NPD9268	Approved
0.7097	Intermediate Similarity	NPD4749	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