NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	270.05
Volume:	265.186
LogP:	3.651
LogD:	2.828
LogS:	-3.918
# Rotatable Bonds:	2
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.622
Synthetic Accessibility Score:	2.633
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.955
MDCK Permeability:	1.063938452716684e-05
Pgp-inhibitor:	0.005
Pgp-substrate:	0.327
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.02
Plasma Protein Binding (PPB):	94.8760986328125%
Volume Distribution (VD):	0.723
Pgp-substrate:	3.080359935760498%

ADMET: Metabolism

CYP1A2-inhibitor:	0.985
CYP1A2-substrate:	0.118
CYP2C19-inhibitor:	0.205
CYP2C19-substrate:	0.049
CYP2C9-inhibitor:	0.368
CYP2C9-substrate:	0.87
CYP2D6-inhibitor:	0.635
CYP2D6-substrate:	0.61
CYP3A4-inhibitor:	0.929
CYP3A4-substrate:	0.087

ADMET: Excretion

Clearance (CL):	8.499
Half-life (T1/2):	0.83

ADMET: Toxicity

hERG Blockers:	0.039
Human Hepatotoxicity (H-HT):	0.083
Drug-inuced Liver Injury (DILI):	0.403
AMES Toxicity:	0.129
Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.947
Skin Sensitization:	0.927
Carcinogencity:	0.045
Eye Corrosion:	0.076
Eye Irritation:	0.938
Respiratory Toxicity:	0.801

Download Data

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

Natural Product: NPC253872

Natural Product ID:	NPC253872
*Common Name:**	2-(3,5-Dihydroxyphenyl)-6-Hydroxybenzofuran-5-Carbaldehyde
IUPAC Name:	2-(3,5-dihydroxyphenyl)-6-hydroxy-1-benzofuran-5-carbaldehyde
Synonyms:
Standard InCHIKey:	JPEZKGGHIXXEFQ-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H10O5/c16-7-10-1-8-4-14(20-15(8)6-13(10)19)9-2-11(17)5-12(18)3-9/h1-7,17-19H
SMILES:	O=Cc1cc2cc(oc2cc1O)c1cc(O)cc(c1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3397405
PubChem CID:	46177530
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

*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
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20815207]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	bark	n.a.	PMID[21319773]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	leaf	n.a.	PMID[22207282]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[23806866]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	Konya, Turkey	2007-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	root bark	University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic	2011-APR	PMID[24901948]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	leaves	Chungbuk, Korea	n.a.	PMID[25935644]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	root	n.a.	PMID[25981820]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	latex	n.a.	PMID[27294120]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	Root barks	n.a.	n.a.	PMID[3097265]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28265	Morus alba	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28265	Morus alba	Species	Moraceae	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	5
MIC	3

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	>	10.0	ug.mL-1	PMID[483567]
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	6.9	ug.mL-1	PMID[483567]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[483567]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	>	100.0	ug.mL-1	PMID[483567]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[483567]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.8	ug.mL-1	PMID[483567]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7.6	ug.mL-1	PMID[483567]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	6.3	ug.mL-1	PMID[483567]

☑ 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 NPC253872 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	514
0.1-0.2	2083
0.2-0.3	5007
0.3-0.4	11551
0.4-0.5	6082
0.5-0.6	4383
0.6-0.7	5445
0.7-0.8	4365
0.8-0.85	2507
0.85-0.9	670
0.9-0.95	87
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.966	High Similarity	NPC116604
0.9595	High Similarity	NPC263676
0.9539	High Similarity	NPC304387
0.9477	High Similarity	NPC193998
0.94	High Similarity	NPC183874
0.9396	High Similarity	NPC170169
0.9392	High Similarity	NPC178202
0.9388	High Similarity	NPC17816
0.9384	High Similarity	NPC155144
0.9355	High Similarity	NPC38914
0.9338	High Similarity	NPC198490
0.9333	High Similarity	NPC130015
0.9333	High Similarity	NPC38361
0.9329	High Similarity	NPC230713
0.9329	High Similarity	NPC78335
0.9276	High Similarity	NPC247677
0.9276	High Similarity	NPC160015
0.9262	High Similarity	NPC226644
0.9262	High Similarity	NPC37226
0.9257	High Similarity	NPC198427
0.9252	High Similarity	NPC98926
0.9236	High Similarity	NPC241820
0.9216	High Similarity	NPC260902
0.9216	High Similarity	NPC296957
0.9211	High Similarity	NPC233776
0.9211	High Similarity	NPC148938
0.9205	High Similarity	NPC5871
0.9205	High Similarity	NPC67654
0.92	High Similarity	NPC135303
0.92	High Similarity	NPC148423
0.9195	High Similarity	NPC306788
0.9189	High Similarity	NPC190572
0.9156	High Similarity	NPC476350
0.9156	High Similarity	NPC476349
0.9156	High Similarity	NPC472877
0.915	High Similarity	NPC180924
0.9145	High Similarity	NPC122365
0.9145	High Similarity	NPC235333
0.9145	High Similarity	NPC213608
0.9145	High Similarity	NPC472462
0.9145	High Similarity	NPC1477
0.9139	High Similarity	NPC115324
0.9139	High Similarity	NPC156244
0.9139	High Similarity	NPC106372
0.9139	High Similarity	NPC472407
0.9139	High Similarity	NPC58668
0.9133	High Similarity	NPC39929
0.9133	High Similarity	NPC296030
0.9128	High Similarity	NPC12148
0.9128	High Similarity	NPC130581
0.9116	High Similarity	NPC53192
0.911	High Similarity	NPC28337
0.9097	High Similarity	NPC304839
0.9097	High Similarity	NPC220582
0.9091	High Similarity	NPC246647
0.9091	High Similarity	NPC96342
0.9091	High Similarity	NPC212967
0.9091	High Similarity	NPC164110
0.9085	High Similarity	NPC297531
0.9085	High Similarity	NPC213936
0.9079	High Similarity	NPC207624
0.9073	High Similarity	NPC167576
0.9073	High Similarity	NPC155882
0.9073	High Similarity	NPC472406
0.9067	High Similarity	NPC135325
0.906	High Similarity	NPC300267
0.906	High Similarity	NPC210826
0.906	High Similarity	NPC51641
0.9054	High Similarity	NPC225884
0.9054	High Similarity	NPC302181
0.9038	High Similarity	NPC30655
0.9038	High Similarity	NPC74854
0.9038	High Similarity	NPC45124
0.902	High Similarity	NPC41719
0.9013	High Similarity	NPC23668
0.9013	High Similarity	NPC193976
0.8993	High Similarity	NPC230943
0.8981	High Similarity	NPC219861
0.8968	High Similarity	NPC268360
0.8968	High Similarity	NPC65504
0.8954	High Similarity	NPC125300
0.8954	High Similarity	NPC142308
0.8944	High Similarity	NPC157522
0.8924	High Similarity	NPC472581
0.8924	High Similarity	NPC109180
0.891	High Similarity	NPC40583
0.8903	High Similarity	NPC45131
0.8896	High Similarity	NPC72370
0.8889	High Similarity	NPC277510
0.8882	High Similarity	NPC37208
0.8882	High Similarity	NPC317492
0.8882	High Similarity	NPC221868
0.8882	High Similarity	NPC131866
0.8868	High Similarity	NPC291110
0.8868	High Similarity	NPC37183
0.8851	High Similarity	NPC182421
0.8846	High Similarity	NPC269495
0.8846	High Similarity	NPC270044
0.8839	High Similarity	NPC99199
0.8836	High Similarity	NPC29638
0.8827	High Similarity	NPC28589
0.8827	High Similarity	NPC248593
0.8816	High Similarity	NPC168085
0.8816	High Similarity	NPC272194
0.8812	High Similarity	NPC277480
0.8812	High Similarity	NPC53640
0.8808	High Similarity	NPC290133
0.8808	High Similarity	NPC24136
0.8808	High Similarity	NPC187282
0.8805	High Similarity	NPC65846
0.88	High Similarity	NPC251182
0.88	High Similarity	NPC262935
0.88	High Similarity	NPC172182
0.8797	High Similarity	NPC24761
0.879	High Similarity	NPC16935
0.879	High Similarity	NPC196879
0.8784	High Similarity	NPC137009
0.8784	High Similarity	NPC37206
0.8782	High Similarity	NPC137100
0.8782	High Similarity	NPC472461
0.8782	High Similarity	NPC474386
0.8774	High Similarity	NPC158261
0.8774	High Similarity	NPC42458
0.8758	High Similarity	NPC266499
0.8758	High Similarity	NPC247973
0.8758	High Similarity	NPC88445
0.875	High Similarity	NPC304443
0.875	High Similarity	NPC136641
0.875	High Similarity	NPC74539
0.8742	High Similarity	NPC110776
0.8742	High Similarity	NPC271590
0.8742	High Similarity	NPC246903
0.8734	High Similarity	NPC260296
0.8734	High Similarity	NPC115432
0.8734	High Similarity	NPC169
0.8733	High Similarity	NPC169479
0.8733	High Similarity	NPC73028
0.8733	High Similarity	NPC159855
0.8726	High Similarity	NPC196448
0.871	High Similarity	NPC41326
0.8707	High Similarity	NPC222633
0.8707	High Similarity	NPC193792
0.8701	High Similarity	NPC191104
0.8701	High Similarity	NPC13282
0.8701	High Similarity	NPC472421
0.8701	High Similarity	NPC202595
0.8701	High Similarity	NPC119929
0.8693	High Similarity	NPC37135
0.8693	High Similarity	NPC39195
0.8693	High Similarity	NPC186397
0.8688	High Similarity	NPC38591
0.8684	High Similarity	NPC2416
0.8684	High Similarity	NPC476153
0.8684	High Similarity	NPC73320
0.8684	High Similarity	NPC215885
0.8679	High Similarity	NPC264293
0.8679	High Similarity	NPC188486
0.8671	High Similarity	NPC244750
0.8671	High Similarity	NPC250076
0.8667	High Similarity	NPC171870
0.8667	High Similarity	NPC3188
0.8654	High Similarity	NPC208806
0.8649	High Similarity	NPC212767
0.8645	High Similarity	NPC318424
0.8645	High Similarity	NPC474744
0.8645	High Similarity	NPC472423
0.8645	High Similarity	NPC474772
0.8642	High Similarity	NPC167479
0.8642	High Similarity	NPC50394
0.8639	High Similarity	NPC60667
0.8636	High Similarity	NPC214493
0.8636	High Similarity	NPC223988
0.8634	High Similarity	NPC474591
0.8627	High Similarity	NPC22005
0.8627	High Similarity	NPC308200
0.8627	High Similarity	NPC7943
0.8627	High Similarity	NPC123202
0.8625	High Similarity	NPC477239
0.8625	High Similarity	NPC84515
0.8625	High Similarity	NPC3448
0.8625	High Similarity	NPC272722
0.8625	High Similarity	NPC312056
0.8618	High Similarity	NPC297788
0.8618	High Similarity	NPC234629
0.8618	High Similarity	NPC303185
0.8618	High Similarity	NPC184649
0.8618	High Similarity	NPC470890
0.8618	High Similarity	NPC224714
0.8618	High Similarity	NPC311741
0.8616	High Similarity	NPC49009
0.8609	High Similarity	NPC470636
0.8609	High Similarity	NPC166858
0.8609	High Similarity	NPC51146
0.8609	High Similarity	NPC96791
0.8609	High Similarity	NPC226942
0.86	High Similarity	NPC101366
0.86	High Similarity	NPC253822
0.8599	High Similarity	NPC473193
0.8598	High Similarity	NPC307286
0.8591	High Similarity	NPC329225

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 NPC253872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	473
0.1-0.2	1033
0.2-0.3	1848
0.3-0.4	2695
0.4-0.5	1745
0.5-0.6	936
0.6-0.7	267
0.7-0.8	103
0.8-0.85	39
0.85-0.9	11
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD920	Approved
0.8742	High Similarity	NPD642	Clinical (unspecified phase)
0.8679	High Similarity	NPD1247	Approved
0.8609	High Similarity	NPD643	Clinical (unspecified phase)
0.8591	High Similarity	NPD1549	Phase 2
0.8523	High Similarity	NPD1550	Clinical (unspecified phase)
0.8523	High Similarity	NPD1552	Clinical (unspecified phase)
0.8514	High Similarity	NPD1510	Phase 2
0.8497	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD6559	Discontinued
0.8418	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1243	Approved
0.8408	Intermediate Similarity	NPD7411	Suspended
0.8375	Intermediate Similarity	NPD3749	Approved
0.8367	Intermediate Similarity	NPD1240	Approved
0.8365	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8323	Intermediate Similarity	NPD919	Approved
0.8313	Intermediate Similarity	NPD3882	Suspended
0.8312	Intermediate Similarity	NPD1511	Approved
0.8289	Intermediate Similarity	NPD2800	Approved
0.8278	Intermediate Similarity	NPD2344	Approved
0.8258	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1607	Approved
0.8239	Intermediate Similarity	NPD1934	Approved
0.8228	Intermediate Similarity	NPD4380	Phase 2
0.8221	Intermediate Similarity	NPD6959	Discontinued
0.8212	Intermediate Similarity	NPD1551	Phase 2
0.8205	Intermediate Similarity	NPD1512	Approved
0.8187	Intermediate Similarity	NPD7819	Suspended
0.8182	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD2532	Approved
0.8141	Intermediate Similarity	NPD2534	Approved
0.8141	Intermediate Similarity	NPD2533	Approved
0.8092	Intermediate Similarity	NPD2796	Approved
0.8084	Intermediate Similarity	NPD3818	Discontinued
0.8075	Intermediate Similarity	NPD2801	Approved
0.8065	Intermediate Similarity	NPD2309	Approved
0.8052	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD5494	Approved
0.8037	Intermediate Similarity	NPD7075	Discontinued
0.7987	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD7768	Phase 2
0.7963	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7904	Intermediate Similarity	NPD3926	Phase 2
0.7857	Intermediate Similarity	NPD6166	Phase 2
0.7857	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7848	Intermediate Similarity	NPD6799	Approved
0.7844	Intermediate Similarity	NPD6232	Discontinued
0.7826	Intermediate Similarity	NPD3226	Approved
0.7811	Intermediate Similarity	NPD7473	Discontinued
0.7792	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6801	Discontinued
0.7771	Intermediate Similarity	NPD3750	Approved
0.7763	Intermediate Similarity	NPD943	Approved
0.7697	Intermediate Similarity	NPD3817	Phase 2
0.7692	Intermediate Similarity	NPD1471	Phase 3
0.7669	Intermediate Similarity	NPD6599	Discontinued
0.7636	Intermediate Similarity	NPD1465	Phase 2
0.7632	Intermediate Similarity	NPD2313	Discontinued
0.763	Intermediate Similarity	NPD5953	Discontinued
0.7616	Intermediate Similarity	NPD7286	Phase 2
0.7616	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5844	Phase 1
0.759	Intermediate Similarity	NPD5402	Approved
0.7572	Intermediate Similarity	NPD7074	Phase 3
0.7564	Intermediate Similarity	NPD2799	Discontinued
0.7558	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD6651	Approved
0.7547	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD1203	Approved
0.7529	Intermediate Similarity	NPD5711	Approved
0.7529	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD5710	Approved
0.7516	Intermediate Similarity	NPD7390	Discontinued
0.7516	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7514	Intermediate Similarity	NPD7054	Approved
0.7485	Intermediate Similarity	NPD2296	Approved
0.7484	Intermediate Similarity	NPD230	Phase 1
0.7471	Intermediate Similarity	NPD7472	Approved
0.7468	Intermediate Similarity	NPD2346	Discontinued
0.7452	Intermediate Similarity	NPD3748	Approved
0.7443	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6797	Phase 2
0.7427	Intermediate Similarity	NPD7229	Phase 3
0.7389	Intermediate Similarity	NPD4287	Approved
0.7386	Intermediate Similarity	NPD7251	Discontinued
0.7383	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD5403	Approved
0.7374	Intermediate Similarity	NPD8434	Phase 2
0.7371	Intermediate Similarity	NPD1729	Discontinued
0.7362	Intermediate Similarity	NPD5401	Approved
0.7345	Intermediate Similarity	NPD7808	Phase 3
0.7326	Intermediate Similarity	NPD6808	Phase 2
0.7321	Intermediate Similarity	NPD5761	Phase 2
0.7321	Intermediate Similarity	NPD5760	Phase 2
0.7296	Intermediate Similarity	NPD6100	Approved
0.7296	Intermediate Similarity	NPD6099	Approved
0.729	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD1610	Phase 2
0.7262	Intermediate Similarity	NPD6280	Approved
0.7262	Intermediate Similarity	NPD6279	Approved
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7261	Intermediate Similarity	NPD447	Suspended
0.7256	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD1548	Phase 1
0.7222	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD4628	Phase 3
0.7219	Intermediate Similarity	NPD9717	Approved
0.7219	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD1613	Approved
0.7197	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD1470	Approved
0.7186	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD3764	Approved
0.7161	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD6832	Phase 2
0.7161	Intermediate Similarity	NPD4908	Phase 1
0.716	Intermediate Similarity	NPD2654	Approved
0.7159	Intermediate Similarity	NPD3751	Discontinued
0.7143	Intermediate Similarity	NPD2403	Approved
0.7111	Intermediate Similarity	NPD8312	Approved
0.7111	Intermediate Similarity	NPD8313	Approved
0.7105	Intermediate Similarity	NPD1608	Approved
0.7097	Intermediate Similarity	NPD9494	Approved
0.7097	Intermediate Similarity	NPD4361	Phase 2
0.7097	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD3658	Clinical (unspecified phase)
0.7081	Intermediate Similarity	NPD5405	Approved
0.7081	Intermediate Similarity	NPD5404	Approved
0.7081	Intermediate Similarity	NPD5408	Approved
0.7081	Intermediate Similarity	NPD5406	Approved
0.7078	Intermediate Similarity	NPD1164	Approved
0.707	Intermediate Similarity	NPD3268	Approved
0.707	Intermediate Similarity	NPD411	Approved
0.7052	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD4360	Phase 2
0.7043	Intermediate Similarity	NPD4363	Phase 3
0.7039	Intermediate Similarity	NPD422	Phase 1
0.7039	Intermediate Similarity	NPD1201	Approved
0.7027	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD7033	Discontinued
0.7011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD4625	Phase 3
0.7	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD9545	Approved
0.6988	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD7199	Phase 2
0.6968	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD37	Approved
0.6954	Remote Similarity	NPD6234	Discontinued
0.6936	Remote Similarity	NPD4965	Approved
0.6936	Remote Similarity	NPD4967	Phase 2
0.6936	Remote Similarity	NPD4966	Approved
0.6932	Remote Similarity	NPD3787	Discontinued
0.6923	Remote Similarity	NPD8151	Discontinued
0.6923	Remote Similarity	NPD1019	Discontinued
0.6923	Remote Similarity	NPD2798	Approved
0.6914	Remote Similarity	NPD4308	Phase 3
0.6908	Remote Similarity	NPD17	Approved
0.6903	Remote Similarity	NPD3225	Approved
0.6893	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6892	Remote Similarity	NPD1241	Discontinued
0.6883	Remote Similarity	NPD9269	Phase 2
0.6879	Remote Similarity	NPD4288	Approved
0.6879	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD2861	Phase 2
0.6872	Remote Similarity	NPD7177	Discontinued
0.6867	Remote Similarity	NPD9493	Approved
0.686	Remote Similarity	NPD6844	Discontinued
0.6859	Remote Similarity	NPD3267	Approved
0.6859	Remote Similarity	NPD3266	Approved
0.6855	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.6855	Remote Similarity	NPD1296	Phase 2
0.6854	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD1252	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD9268	Approved
0.6807	Remote Similarity	NPD7003	Approved
0.6802	Remote Similarity	NPD5890	Approved
0.6802	Remote Similarity	NPD5889	Approved
0.68	Remote Similarity	NPD6971	Discontinued
0.6795	Remote Similarity	NPD1283	Approved
0.6792	Remote Similarity	NPD3027	Phase 3
0.6788	Remote Similarity	NPD2424	Discontinued
0.6784	Remote Similarity	NPD7458	Discontinued
0.6778	Remote Similarity	NPD2163	Approved
0.6774	Remote Similarity	NPD1481	Phase 2
0.6774	Remote Similarity	NPD3972	Approved
0.6771	Remote Similarity	NPD6782	Approved
0.6771	Remote Similarity	NPD6777	Approved
0.6771	Remote Similarity	NPD6779	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