NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	272.07
Volume:	273.743
LogP:	2.593
LogD:	1.897
LogS:	-2.379
# Rotatable Bonds:	3
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.391
Synthetic Accessibility Score:	2.296
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.072
MDCK Permeability:	1.1802326298493426e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.094
30% Bioavailability (F30%):	0.099

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.049
Plasma Protein Binding (PPB):	100.00890350341797%
Volume Distribution (VD):	0.407
Pgp-substrate:	1.2094533443450928%

ADMET: Metabolism

CYP1A2-inhibitor:	0.817
CYP1A2-substrate:	0.1
CYP2C19-inhibitor:	0.147
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.622
CYP2C9-substrate:	0.633
CYP2D6-inhibitor:	0.482
CYP2D6-substrate:	0.474
CYP3A4-inhibitor:	0.6
CYP3A4-substrate:	0.148

ADMET: Excretion

Clearance (CL):	14.044
Half-life (T1/2):	0.942

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.461
Drug-inuced Liver Injury (DILI):	0.624
AMES Toxicity:	0.763
Rat Oral Acute Toxicity:	0.641
Maximum Recommended Daily Dose:	0.492
Skin Sensitization:	0.959
Carcinogencity:	0.536
Eye Corrosion:	0.007
Eye Irritation:	0.943
Respiratory Toxicity:	0.469

Download Data

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

Natural Product: NPC469526

Natural Product ID:	NPC469526
*Common Name:**	(E)-3,2',4'-Trihydroxy-3'-Methoxychalcone
IUPAC Name:	(E)-3-(3-hydroxyphenyl)-1-(2,3,4-trihydroxyphenyl)prop-2-en-1-one
Synonyms:
Standard InCHIKey:	GADGMUTUOCVUJQ-GQCTYLIASA-N
Standard InCHI:	InChI=1S/C15H12O5/c16-10-3-1-2-9(8-10)4-6-12(17)11-5-7-13(18)15(20)14(11)19/h1-8,16,18-20H/b6-4+
SMILES:	Oc1cccc(c1)/C=C/C(=O)c1ccc(c(c1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1082538
PubChem CID:	45279391
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
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	leaf	n.a.	n.a.	PMID[20035557]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
MIC	2
Others	2

Activity Type	# Activity
Cell Line	1
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	333200.0	nM	PMID[558944]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	174800.0	nM	PMID[558944]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	Inhibition	=	99.5	%	PMID[558944]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	104800.0	nM	PMID[558944]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MBC	=	183.7	uM	PMID[558944]

☑ 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 NPC469526 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	426
0.1-0.2	1915
0.2-0.3	5378
0.3-0.4	12469
0.4-0.5	5010
0.5-0.6	5023
0.6-0.7	5950
0.7-0.8	5534
0.8-0.85	820
0.85-0.9	129
0.9-0.95	37
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC34070
0.992	High Similarity	NPC135801
0.9919	High Similarity	NPC26697
0.976	High Similarity	NPC233056
0.952	High Similarity	NPC107672
0.9462	High Similarity	NPC264112
0.9462	High Similarity	NPC194764
0.9462	High Similarity	NPC65005
0.9449	High Similarity	NPC244441
0.944	High Similarity	NPC8745
0.9435	High Similarity	NPC13238
0.9389	High Similarity	NPC290030
0.936	High Similarity	NPC10926
0.9323	High Similarity	NPC203063
0.9318	High Similarity	NPC175552
0.9248	High Similarity	NPC472903
0.9194	High Similarity	NPC19174
0.9194	High Similarity	NPC73532
0.9194	High Similarity	NPC143427
0.9194	High Similarity	NPC267552
0.9194	High Similarity	NPC115159
0.9194	High Similarity	NPC224273
0.9194	High Similarity	NPC45438
0.912	High Similarity	NPC32032
0.912	High Similarity	NPC133909
0.9118	High Similarity	NPC287722
0.9118	High Similarity	NPC238629
0.9113	High Similarity	NPC297186
0.9111	High Similarity	NPC472904
0.9098	High Similarity	NPC170742
0.9062	High Similarity	NPC214620
0.9051	High Similarity	NPC142165
0.9044	High Similarity	NPC284556
0.9044	High Similarity	NPC301178
0.904	High Similarity	NPC156139
0.904	High Similarity	NPC242895
0.9023	High Similarity	NPC223836
0.8978	High Similarity	NPC254659
0.8978	High Similarity	NPC471417
0.896	High Similarity	NPC248363
0.8952	High Similarity	NPC158222
0.8947	High Similarity	NPC72918
0.8915	High Similarity	NPC156539
0.8913	High Similarity	NPC38065
0.8913	High Similarity	NPC242893
0.888	High Similarity	NPC159525
0.8872	High Similarity	NPC282780
0.8872	High Similarity	NPC166480
0.8872	High Similarity	NPC44437
0.8857	High Similarity	NPC125449
0.8857	High Similarity	NPC188074
0.8857	High Similarity	NPC168803
0.8849	High Similarity	NPC70136
0.8806	High Similarity	NPC129752
0.88	High Similarity	NPC161617
0.8797	High Similarity	NPC294226
0.8794	High Similarity	NPC287395
0.8794	High Similarity	NPC43669
0.8794	High Similarity	NPC183655
0.8794	High Similarity	NPC12367
0.8794	High Similarity	NPC272721
0.8794	High Similarity	NPC196277
0.8794	High Similarity	NPC218490
0.8794	High Similarity	NPC118726
0.8779	High Similarity	NPC109123
0.8779	High Similarity	NPC92624
0.8779	High Similarity	NPC474998
0.8777	High Similarity	NPC279121
0.8769	High Similarity	NPC105157
0.8769	High Similarity	NPC162612
0.8769	High Similarity	NPC190043
0.8769	High Similarity	NPC266689
0.8769	High Similarity	NPC98254
0.8769	High Similarity	NPC169250
0.8769	High Similarity	NPC103356
0.8769	High Similarity	NPC23126
0.8769	High Similarity	NPC100067
0.8769	High Similarity	NPC72158
0.8769	High Similarity	NPC30501
0.8768	High Similarity	NPC312256
0.8759	High Similarity	NPC50823
0.875	High Similarity	NPC416
0.875	High Similarity	NPC61398
0.874	High Similarity	NPC196976
0.8732	High Similarity	NPC69430
0.8732	High Similarity	NPC92722
0.8732	High Similarity	NPC40290
0.8732	High Similarity	NPC139293
0.8732	High Similarity	NPC333691
0.8732	High Similarity	NPC142876
0.8732	High Similarity	NPC200060
0.8732	High Similarity	NPC264550
0.8732	High Similarity	NPC264289
0.8732	High Similarity	NPC195763
0.8732	High Similarity	NPC102003
0.8723	High Similarity	NPC77378
0.8723	High Similarity	NPC140840
0.8723	High Similarity	NPC86847
0.8723	High Similarity	NPC275772
0.8723	High Similarity	NPC239312
0.8723	High Similarity	NPC74881
0.8723	High Similarity	NPC51443
0.8723	High Similarity	NPC130230
0.8723	High Similarity	NPC95864
0.872	High Similarity	NPC40649
0.872	High Similarity	NPC209486
0.8712	High Similarity	NPC259942
0.8712	High Similarity	NPC117609
0.8712	High Similarity	NPC147757
0.8705	High Similarity	NPC175013
0.8705	High Similarity	NPC119663
0.8702	High Similarity	NPC21305
0.8702	High Similarity	NPC179898
0.8702	High Similarity	NPC221777
0.8702	High Similarity	NPC473017
0.8696	High Similarity	NPC110419
0.8692	High Similarity	NPC62952
0.8692	High Similarity	NPC267846
0.8676	High Similarity	NPC147418
0.8676	High Similarity	NPC53206
0.8676	High Similarity	NPC53414
0.8672	High Similarity	NPC225710
0.8671	High Similarity	NPC472279
0.8671	High Similarity	NPC10467
0.8671	High Similarity	NPC45873
0.8671	High Similarity	NPC260582
0.8671	High Similarity	NPC29231
0.8662	High Similarity	NPC254702
0.8662	High Similarity	NPC19545
0.8662	High Similarity	NPC80710
0.8662	High Similarity	NPC15329
0.8662	High Similarity	NPC276930
0.8662	High Similarity	NPC131451
0.8662	High Similarity	NPC194856
0.8662	High Similarity	NPC194653
0.8662	High Similarity	NPC471907
0.8662	High Similarity	NPC139364
0.8662	High Similarity	NPC203747
0.8661	High Similarity	NPC146642
0.8652	High Similarity	NPC20791
0.8652	High Similarity	NPC179271
0.8643	High Similarity	NPC105213
0.8643	High Similarity	NPC257025
0.8643	High Similarity	NPC207732
0.864	High Similarity	NPC150919
0.8636	High Similarity	NPC120488
0.8636	High Similarity	NPC102829
0.8633	High Similarity	NPC291078
0.8626	High Similarity	NPC116513
0.8613	High Similarity	NPC123714
0.8611	High Similarity	NPC31363
0.8611	High Similarity	NPC227485
0.8611	High Similarity	NPC251110
0.8603	High Similarity	NPC254847
0.8601	High Similarity	NPC216318
0.8601	High Similarity	NPC183959
0.8601	High Similarity	NPC105512
0.8601	High Similarity	NPC17286
0.8601	High Similarity	NPC1612
0.8601	High Similarity	NPC296197
0.8601	High Similarity	NPC195351
0.8601	High Similarity	NPC259713
0.8601	High Similarity	NPC38545
0.8601	High Similarity	NPC171916
0.8592	High Similarity	NPC108406
0.8592	High Similarity	NPC93034
0.8592	High Similarity	NPC207729
0.8592	High Similarity	NPC119660
0.8583	High Similarity	NPC294037
0.8582	High Similarity	NPC17843
0.8582	High Similarity	NPC478190
0.8561	High Similarity	NPC247250
0.8561	High Similarity	NPC767
0.8552	High Similarity	NPC35763
0.8552	High Similarity	NPC245382
0.8552	High Similarity	NPC60972
0.8552	High Similarity	NPC100263
0.8552	High Similarity	NPC257648
0.8552	High Similarity	NPC291802
0.8552	High Similarity	NPC100971
0.8552	High Similarity	NPC269451
0.8552	High Similarity	NPC477231
0.8552	High Similarity	NPC121522
0.8552	High Similarity	NPC149889
0.8552	High Similarity	NPC181209
0.8552	High Similarity	NPC312338
0.8552	High Similarity	NPC39732
0.8552	High Similarity	NPC209487
0.8552	High Similarity	NPC131266
0.8552	High Similarity	NPC216769
0.8551	High Similarity	NPC471819
0.8551	High Similarity	NPC242994
0.8551	High Similarity	NPC138099
0.8542	High Similarity	NPC62042
0.8542	High Similarity	NPC248102
0.8542	High Similarity	NPC85131
0.8542	High Similarity	NPC77858
0.8542	High Similarity	NPC184136
0.8542	High Similarity	NPC61620
0.854	High Similarity	NPC471905

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 NPC469526 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	405
0.1-0.2	988
0.2-0.3	1691
0.3-0.4	3048
0.4-0.5	1712
0.5-0.6	911
0.6-0.7	285
0.7-0.8	90
0.8-0.85	15
0.85-0.9	3
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.992	High Similarity	NPD943	Approved
0.9167	High Similarity	NPD651	Clinical (unspecified phase)
0.8777	High Similarity	NPD1511	Approved
0.8672	High Similarity	NPD9269	Phase 2
0.8652	High Similarity	NPD1512	Approved
0.8603	High Similarity	NPD1509	Clinical (unspecified phase)
0.8378	Intermediate Similarity	NPD3882	Suspended
0.8367	Intermediate Similarity	NPD2801	Approved
0.8359	Intermediate Similarity	NPD9268	Approved
0.8333	Intermediate Similarity	NPD1510	Phase 2
0.8309	Intermediate Similarity	NPD1240	Approved
0.8299	Intermediate Similarity	NPD1934	Approved
0.8248	Intermediate Similarity	NPD230	Phase 1
0.8243	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8195	Intermediate Similarity	NPD1470	Approved
0.8188	Intermediate Similarity	NPD1607	Approved
0.803	Intermediate Similarity	NPD1201	Approved
0.8028	Intermediate Similarity	NPD1549	Phase 2
0.7984	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7958	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD3818	Discontinued
0.7877	Intermediate Similarity	NPD7390	Discontinued
0.78	Intermediate Similarity	NPD4380	Phase 2
0.7794	Intermediate Similarity	NPD1164	Approved
0.7778	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6166	Phase 2
0.7771	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD3817	Phase 2
0.7703	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD1465	Phase 2
0.7643	Intermediate Similarity	NPD6232	Discontinued
0.7639	Intermediate Similarity	NPD5405	Approved
0.7639	Intermediate Similarity	NPD5406	Approved
0.7639	Intermediate Similarity	NPD5404	Approved
0.7639	Intermediate Similarity	NPD5408	Approved
0.7638	Intermediate Similarity	NPD9266	Approved
0.7638	Intermediate Similarity	NPD74	Approved
0.7635	Intermediate Similarity	NPD6799	Approved
0.7625	Intermediate Similarity	NPD7054	Approved
0.761	Intermediate Similarity	NPD7473	Discontinued
0.7584	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7472	Approved
0.7578	Intermediate Similarity	NPD7074	Phase 3
0.7559	Intermediate Similarity	NPD9264	Approved
0.7559	Intermediate Similarity	NPD9263	Approved
0.7559	Intermediate Similarity	NPD9267	Approved
0.7559	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD9494	Approved
0.7546	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD6797	Phase 2
0.7517	Intermediate Similarity	NPD1551	Phase 2
0.7517	Intermediate Similarity	NPD2796	Approved
0.7517	Intermediate Similarity	NPD2935	Discontinued
0.75	Intermediate Similarity	NPD7075	Discontinued
0.75	Intermediate Similarity	NPD6190	Approved
0.75	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1242	Phase 1
0.7485	Intermediate Similarity	NPD7251	Discontinued
0.7483	Intermediate Similarity	NPD447	Suspended
0.7444	Intermediate Similarity	NPD9493	Approved
0.7432	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD3750	Approved
0.7419	Intermediate Similarity	NPD7819	Suspended
0.7419	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD1203	Approved
0.7405	Intermediate Similarity	NPD5494	Approved
0.7389	Intermediate Similarity	NPD3749	Approved
0.7376	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD2344	Approved
0.7338	Intermediate Similarity	NPD6599	Discontinued
0.7333	Intermediate Similarity	NPD7808	Phase 3
0.7317	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD3021	Approved
0.7308	Intermediate Similarity	NPD3022	Approved
0.7305	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD9281	Approved
0.729	Intermediate Similarity	NPD7411	Suspended
0.7267	Intermediate Similarity	NPD3926	Phase 2
0.7266	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD5402	Approved
0.7255	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD1247	Approved
0.7248	Intermediate Similarity	NPD2800	Approved
0.7244	Intermediate Similarity	NPD6801	Discontinued
0.7244	Intermediate Similarity	NPD9261	Approved
0.7233	Intermediate Similarity	NPD919	Approved
0.7219	Intermediate Similarity	NPD3300	Phase 2
0.7206	Intermediate Similarity	NPD9545	Approved
0.7172	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD1613	Approved
0.7165	Intermediate Similarity	NPD940	Approved
0.7165	Intermediate Similarity	NPD846	Approved
0.7153	Intermediate Similarity	NPD3764	Approved
0.7153	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD2309	Approved
0.7143	Intermediate Similarity	NPD5403	Approved
0.7133	Intermediate Similarity	NPD1243	Approved
0.7124	Intermediate Similarity	NPD2532	Approved
0.7124	Intermediate Similarity	NPD2534	Approved
0.7124	Intermediate Similarity	NPD2533	Approved
0.7124	Intermediate Similarity	NPD5401	Approved
0.7095	Intermediate Similarity	NPD2799	Discontinued
0.7095	Intermediate Similarity	NPD3748	Approved
0.7083	Intermediate Similarity	NPD3027	Phase 3
0.7075	Intermediate Similarity	NPD6651	Approved
0.7071	Intermediate Similarity	NPD9717	Approved
0.7037	Intermediate Similarity	NPD6959	Discontinued
0.7034	Intermediate Similarity	NPD2313	Discontinued
0.7034	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD920	Approved
0.7013	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7768	Phase 2
0.6993	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD2798	Approved
0.6988	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6988	Remote Similarity	NPD5844	Phase 1
0.6964	Remote Similarity	NPD6559	Discontinued
0.6943	Remote Similarity	NPD3226	Approved
0.6933	Remote Similarity	NPD9570	Approved
0.6918	Remote Similarity	NPD411	Approved
0.6917	Remote Similarity	NPD4750	Phase 3
0.6908	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD5953	Discontinued
0.6892	Remote Similarity	NPD1933	Approved
0.6887	Remote Similarity	NPD2346	Discontinued
0.6879	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD257	Approved
0.6875	Remote Similarity	NPD258	Approved
0.6871	Remote Similarity	NPD520	Approved
0.6863	Remote Similarity	NPD8166	Discontinued
0.6863	Remote Similarity	NPD4628	Phase 3
0.6839	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD3455	Phase 2
0.6828	Remote Similarity	NPD9569	Approved
0.6826	Remote Similarity	NPD3751	Discontinued
0.6821	Remote Similarity	NPD6100	Approved
0.6821	Remote Similarity	NPD6099	Approved
0.6816	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2654	Approved
0.6794	Remote Similarity	NPD1237	Approved
0.6786	Remote Similarity	NPD7286	Phase 2
0.6782	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6832	Phase 2
0.6779	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6776	Remote Similarity	NPD7266	Discontinued
0.6763	Remote Similarity	NPD5536	Phase 2
0.6761	Remote Similarity	NPD422	Phase 1
0.6755	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6741	Remote Similarity	NPD9280	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD2932	Approved
0.6738	Remote Similarity	NPD3019	Approved
0.6731	Remote Similarity	NPD4357	Discontinued
0.6714	Remote Similarity	NPD1548	Phase 1
0.6713	Remote Similarity	NPD3972	Approved
0.6713	Remote Similarity	NPD1608	Approved
0.6707	Remote Similarity	NPD1220	Phase 1
0.6707	Remote Similarity	NPD6234	Discontinued
0.6693	Remote Similarity	NPD2934	Approved
0.6693	Remote Similarity	NPD2933	Approved
0.6691	Remote Similarity	NPD228	Approved
0.6686	Remote Similarity	NPD6020	Phase 2
0.6667	Remote Similarity	NPD1471	Phase 3
0.6667	Remote Similarity	NPD8150	Discontinued
0.6667	Remote Similarity	NPD1653	Approved
0.6647	Remote Similarity	NPD5242	Approved
0.6645	Remote Similarity	NPD4308	Phase 3
0.6645	Remote Similarity	NPD1196	Approved
0.6645	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD259	Phase 1
0.6643	Remote Similarity	NPD1610	Phase 2
0.6642	Remote Similarity	NPD9379	Approved
0.6642	Remote Similarity	NPD9377	Approved
0.6641	Remote Similarity	NPD2860	Approved
0.6641	Remote Similarity	NPD2859	Approved
0.6628	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD7199	Phase 2
0.6626	Remote Similarity	NPD2296	Approved
0.6624	Remote Similarity	NPD1543	Discontinued
0.6622	Remote Similarity	NPD9537	Phase 1
0.6622	Remote Similarity	NPD9536	Phase 1
0.6615	Remote Similarity	NPD3020	Approved
0.6613	Remote Similarity	NPD9094	Approved
0.661	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6609	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD37	Approved
0.66	Remote Similarity	NPD825	Approved
0.66	Remote Similarity	NPD826	Approved
0.6599	Remote Similarity	NPD3018	Phase 2
0.6588	Remote Similarity	NPD1221	Approved
0.6587	Remote Similarity	NPD5710	Approved
0.6587	Remote Similarity	NPD5711	Approved
0.6587	Remote Similarity	NPD3787	Discontinued
0.6581	Remote Similarity	NPD1195	Approved
0.6577	Remote Similarity	NPD3268	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