NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.06
Volume:	256.396
LogP:	2.695
LogD:	2.657
LogS:	-3.436
# Rotatable Bonds:	1
TPSA:	66.76
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.768
Synthetic Accessibility Score:	2.197
Fsp3:	0.0
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.928
MDCK Permeability:	1.812569098547101e-05
Pgp-inhibitor:	0.008
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.022

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.094
Plasma Protein Binding (PPB):	98.75884246826172%
Volume Distribution (VD):	0.524
Pgp-substrate:	1.4306591749191284%

ADMET: Metabolism

CYP1A2-inhibitor:	0.972
CYP1A2-substrate:	0.086
CYP2C19-inhibitor:	0.844
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.704
CYP2C9-substrate:	0.875
CYP2D6-inhibitor:	0.665
CYP2D6-substrate:	0.697
CYP3A4-inhibitor:	0.891
CYP3A4-substrate:	0.207

ADMET: Excretion

Clearance (CL):	9.791
Half-life (T1/2):	0.869

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.172
Drug-inuced Liver Injury (DILI):	0.469
AMES Toxicity:	0.882
Rat Oral Acute Toxicity:	0.48
Maximum Recommended Daily Dose:	0.906
Skin Sensitization:	0.898
Carcinogencity:	0.828
Eye Corrosion:	0.004
Eye Irritation:	0.96
Respiratory Toxicity:	0.155

Download Data

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

Natural Product: NPC254841

Natural Product ID:	NPC254841
*Common Name:**	2-(4'-Hydroxybenzylidene)-6-Hydroxybenzofuran-3(2H)-One
IUPAC Name:	(2Z)-6-hydroxy-2-[(4-hydroxyphenyl)methylidene]-1-benzofuran-3-one
Synonyms:
Standard InCHIKey:	KEZLDSPIRVZOKZ-AUWJEWJLSA-N
Standard InCHI:	InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)7-14-15(18)12-6-5-11(17)8-13(12)19-14/h1-8,16-17H/b14-7-
SMILES:	c1cc(ccc1/C=C1/C(=O)c2ccc(cc2O1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL426110
PubChem CID:	5281254
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0001631] Aurone 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
NPO13593	Cladonia chlorophaea	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11675	Kyllinga erecta	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14584	Pinus orientalis	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28745	Heterotheca villosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO269	Leptospermum polygalifolium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13593	Cladonia chlorophaea	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10573	Lilium mackliniae	Species	Liliaceae	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	11
Ki	4
MIC	2
Others	16

Activity Type	# Activity
Cell Line	7
Individual Protein	16
Organism	3
Others	7

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	38700.0	nM	PMID[493366]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1060.0	nM	PMID[493366]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	99790.0	nM	PMID[493366]
NPT139	Cell Line	HT-29	Homo sapiens	Inhibition	=	80.3	%	PMID[493370]
NPT139	Cell Line	HT-29	Homo sapiens	IC50	=	500.0	nM	PMID[493370]
NPT139	Cell Line	HT-29	Homo sapiens	Ratio IC50	=	40000.0	n.a.	PMID[493370]
NPT139	Cell Line	HT-29	Homo sapiens	Ratio	>	12.0	n.a.	PMID[493370]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	IC50	=	260.0	nM	PMID[493371]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	IC50	=	2450.0	nM	PMID[493371]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Inhibition	=	29.8	%	PMID[493371]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Inhibition	=	83.7	%	PMID[493371]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Activity	=	87.5	%	PMID[493371]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Activity	=	28.0	%	PMID[493371]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Ki	=	100.0	nM	PMID[493371]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Ki	=	510.0	nM	PMID[493371]
NPT43	Individual Protein	Tyrosinase	Agaricus bisporus	IC50	=	38400.0	nM	PMID[493373]
NPT1315	Individual Protein	Adenosine A1 receptor	Rattus norvegicus	Ki	=	352.0	nM	PMID[493374]
NPT1316	Individual Protein	Adenosine A2a receptor	Rattus norvegicus	Ki	>	100000.0	nM	PMID[493374]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	IC50	=	38400.0	nM	PMID[493363]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	69.0	%	PMID[493363]
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	FC	=	1.01	n.a.	PMID[493364]
NPT935	Individual Protein	Quinone reductase 1)	Homo sapiens	FC	=	1.8	n.a.	PMID[493364]
NPT27	Others	Unspecified		Activity	=	100.0	%	PMID[493364]
NPT27	Others	Unspecified		Activity	=	98.0	%	PMID[493364]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	130000.0	nM	PMID[493365]
NPT2	Others	Unspecified		Inhibition	=	35.0	%	PMID[493367]
NPT2	Others	Unspecified		IC50	>	20000.0	nM	PMID[493367]
NPT2	Others	Unspecified		IC50	=	76710.0	nM	PMID[493368]
NPT2	Others	Unspecified		Ratio IC50	=	9.4	n.a.	PMID[493369]
NPT2	Others	Unspecified		Ratio IC50	=	9.4	n.a.	PMID[493371]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	500000.0	nM	PMID[493372]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	500000.0	nM	PMID[493372]
NPT741	Individual Protein	Tyrosinase	Homo sapiens	Inhibition	=	69.0	%	PMID[493373]

☑ 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 NPC254841 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	429
0.1-0.2	2082
0.2-0.3	5552
0.3-0.4	11670
0.4-0.5	5163
0.5-0.6	4430
0.6-0.7	5874
0.7-0.8	4818
0.8-0.85	1761
0.85-0.9	776
0.9-0.95	139
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9632	High Similarity	NPC471520
0.9559	High Similarity	NPC310128
0.9552	High Similarity	NPC299379
0.9478	High Similarity	NPC256042
0.9478	High Similarity	NPC216361
0.9478	High Similarity	NPC116775
0.9478	High Similarity	NPC281917
0.9478	High Similarity	NPC187432
0.9474	High Similarity	NPC172262
0.9416	High Similarity	NPC136840
0.9403	High Similarity	NPC239495
0.9403	High Similarity	NPC9985
0.9398	High Similarity	NPC78540
0.9398	High Similarity	NPC50898
0.9398	High Similarity	NPC213216
0.9398	High Similarity	NPC274121
0.9398	High Similarity	NPC57601
0.9357	High Similarity	NPC140840
0.9357	High Similarity	NPC86847
0.9353	High Similarity	NPC71210
0.9343	High Similarity	NPC146679
0.9343	High Similarity	NPC184536
0.9343	High Similarity	NPC281207
0.9343	High Similarity	NPC230285
0.9343	High Similarity	NPC103342
0.9343	High Similarity	NPC103904
0.9343	High Similarity	NPC269652
0.9343	High Similarity	NPC59951
0.9328	High Similarity	NPC248872
0.9291	High Similarity	NPC19545
0.9275	High Similarity	NPC90582
0.9275	High Similarity	NPC262094
0.927	High Similarity	NPC241838
0.927	High Similarity	NPC152042
0.927	High Similarity	NPC143799
0.9265	High Similarity	NPC250266
0.9265	High Similarity	NPC266597
0.9265	High Similarity	NPC290291
0.9265	High Similarity	NPC188879
0.9265	High Similarity	NPC275055
0.9248	High Similarity	NPC113006
0.9209	High Similarity	NPC53192
0.9197	High Similarity	NPC188947
0.9197	High Similarity	NPC124269
0.9197	High Similarity	NPC280284
0.9197	High Similarity	NPC147686
0.9197	High Similarity	NPC329225
0.9197	High Similarity	NPC472460
0.9197	High Similarity	NPC99333
0.9191	High Similarity	NPC231772
0.9191	High Similarity	NPC194281
0.9191	High Similarity	NPC124784
0.9191	High Similarity	NPC47815
0.9191	High Similarity	NPC240593
0.9191	High Similarity	NPC13408
0.9191	High Similarity	NPC29353
0.9191	High Similarity	NPC234133
0.9191	High Similarity	NPC127447
0.9191	High Similarity	NPC473887
0.9179	High Similarity	NPC205468
0.9179	High Similarity	NPC87231
0.9179	High Similarity	NPC129132
0.9179	High Similarity	NPC212631
0.9179	High Similarity	NPC128216
0.9179	High Similarity	NPC257756
0.9173	High Similarity	NPC5515
0.9173	High Similarity	NPC270369
0.9161	High Similarity	NPC260582
0.9143	High Similarity	NPC302181
0.9143	High Similarity	NPC470216
0.913	High Similarity	NPC261234
0.9124	High Similarity	NPC243083
0.9124	High Similarity	NPC84585
0.9124	High Similarity	NPC476480
0.9124	High Similarity	NPC228661
0.9124	High Similarity	NPC13768
0.9124	High Similarity	NPC287246
0.9124	High Similarity	NPC107586
0.9124	High Similarity	NPC12296
0.9124	High Similarity	NPC79943
0.9124	High Similarity	NPC295261
0.9124	High Similarity	NPC32441
0.9124	High Similarity	NPC296490
0.9111	High Similarity	NPC139813
0.9111	High Similarity	NPC472365
0.9111	High Similarity	NPC263670
0.9111	High Similarity	NPC188646
0.9111	High Similarity	NPC242294
0.9111	High Similarity	NPC56031
0.9111	High Similarity	NPC175098
0.9111	High Similarity	NPC192304
0.9111	High Similarity	NPC312318
0.9111	High Similarity	NPC337373
0.9104	High Similarity	NPC64359
0.9104	High Similarity	NPC31872
0.9104	High Similarity	NPC473584
0.9104	High Similarity	NPC308037
0.9104	High Similarity	NPC475589
0.9104	High Similarity	NPC262359
0.9104	High Similarity	NPC313618
0.9078	High Similarity	NPC155144
0.9078	High Similarity	NPC230943
0.9071	High Similarity	NPC473042
0.9071	High Similarity	NPC200694
0.9065	High Similarity	NPC172986
0.9065	High Similarity	NPC270883
0.9065	High Similarity	NPC261227
0.9065	High Similarity	NPC69769
0.9058	High Similarity	NPC118813
0.9058	High Similarity	NPC276905
0.9058	High Similarity	NPC201395
0.9044	High Similarity	NPC286336
0.9037	High Similarity	NPC25937
0.9037	High Similarity	NPC10971
0.9034	High Similarity	NPC304954
0.903	High Similarity	NPC137264
0.9023	High Similarity	NPC197425
0.9014	High Similarity	NPC178343
0.9014	High Similarity	NPC148011
0.9014	High Similarity	NPC1940
0.9014	High Similarity	NPC306488
0.9014	High Similarity	NPC5820
0.9014	High Similarity	NPC153758
0.9014	High Similarity	NPC210826
0.9014	High Similarity	NPC229190
0.9007	High Similarity	NPC190637
0.9007	High Similarity	NPC212932
0.9007	High Similarity	NPC158874
0.9007	High Similarity	NPC9117
0.9007	High Similarity	NPC293053
0.9007	High Similarity	NPC24821
0.9007	High Similarity	NPC225884
0.9	High Similarity	NPC147688
0.9	High Similarity	NPC156590
0.9	High Similarity	NPC3188
0.9	High Similarity	NPC150023
0.9	High Similarity	NPC205006
0.9	High Similarity	NPC64908
0.9	High Similarity	NPC110969
0.9	High Similarity	NPC118840
0.8993	High Similarity	NPC18260
0.8993	High Similarity	NPC303633
0.8993	High Similarity	NPC310135
0.8993	High Similarity	NPC96565
0.8993	High Similarity	NPC20709
0.8993	High Similarity	NPC78913
0.8993	High Similarity	NPC316480
0.8993	High Similarity	NPC220062
0.8993	High Similarity	NPC265871
0.8993	High Similarity	NPC301217
0.8993	High Similarity	NPC329203
0.8993	High Similarity	NPC216978
0.8993	High Similarity	NPC274784
0.8993	High Similarity	NPC55018
0.8993	High Similarity	NPC222342
0.8993	High Similarity	NPC150648
0.8993	High Similarity	NPC225153
0.8986	High Similarity	NPC160972
0.8978	High Similarity	NPC234560
0.8978	High Similarity	NPC39426
0.8978	High Similarity	NPC151113
0.8973	High Similarity	NPC189130
0.8971	High Similarity	NPC223457
0.8971	High Similarity	NPC204960
0.8971	High Similarity	NPC108113
0.8971	High Similarity	NPC294593
0.8971	High Similarity	NPC93756
0.8971	High Similarity	NPC144051
0.8971	High Similarity	NPC82225
0.8971	High Similarity	NPC159623
0.8971	High Similarity	NPC18877
0.8971	High Similarity	NPC28753
0.8971	High Similarity	NPC20560
0.8963	High Similarity	NPC65060
0.8955	High Similarity	NPC115998
0.8955	High Similarity	NPC247779
0.8955	High Similarity	NPC185497
0.8955	High Similarity	NPC39753
0.8951	High Similarity	NPC12148
0.8951	High Similarity	NPC74881
0.8951	High Similarity	NPC51443
0.8951	High Similarity	NPC130581
0.8947	High Similarity	NPC80694
0.8947	High Similarity	NPC186098
0.8944	High Similarity	NPC208176
0.8944	High Similarity	NPC273538
0.8944	High Similarity	NPC279417
0.8944	High Similarity	NPC142731
0.8944	High Similarity	NPC49130
0.8944	High Similarity	NPC62290
0.8944	High Similarity	NPC216538
0.8944	High Similarity	NPC4152
0.8944	High Similarity	NPC306607
0.8944	High Similarity	NPC326500
0.8944	High Similarity	NPC326506
0.8936	High Similarity	NPC159855
0.8936	High Similarity	NPC11561
0.8936	High Similarity	NPC202981
0.8936	High Similarity	NPC226636
0.8936	High Similarity	NPC169479

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 NPC254841 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	404
0.1-0.2	1026
0.2-0.3	1622
0.3-0.4	2736
0.4-0.5	1757
0.5-0.6	1106
0.6-0.7	323
0.7-0.8	131
0.8-0.85	30
0.85-0.9	10
0.9-0.95	5
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9197	High Similarity	NPD1549	Phase 2
0.9124	High Similarity	NPD1550	Clinical (unspecified phase)
0.9124	High Similarity	NPD1552	Clinical (unspecified phase)
0.9104	High Similarity	NPD1240	Approved
0.8978	High Similarity	NPD1510	Phase 2
0.8971	High Similarity	NPD1607	Approved
0.8944	High Similarity	NPD4378	Clinical (unspecified phase)
0.8881	High Similarity	NPD1512	Approved
0.8873	High Similarity	NPD6799	Approved
0.8851	High Similarity	NPD3882	Suspended
0.8741	High Similarity	NPD1511	Approved
0.8681	High Similarity	NPD7410	Clinical (unspecified phase)
0.8543	High Similarity	NPD7075	Discontinued
0.8514	High Similarity	NPD6599	Discontinued
0.8511	High Similarity	NPD2796	Approved
0.8511	High Similarity	NPD1551	Phase 2
0.8467	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8444	Intermediate Similarity	NPD1203	Approved
0.8421	Intermediate Similarity	NPD3749	Approved
0.8403	Intermediate Similarity	NPD3750	Approved
0.84	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD2800	Approved
0.8333	Intermediate Similarity	NPD7411	Suspended
0.8333	Intermediate Similarity	NPD1243	Approved
0.8322	Intermediate Similarity	NPD2344	Approved
0.8311	Intermediate Similarity	NPD5403	Approved
0.8299	Intermediate Similarity	NPD5401	Approved
0.8278	Intermediate Similarity	NPD1934	Approved
0.8267	Intermediate Similarity	NPD4380	Phase 2
0.8264	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD2801	Approved
0.8182	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.817	Intermediate Similarity	NPD3817	Phase 2
0.817	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8163	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.8143	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8105	Intermediate Similarity	NPD7819	Suspended
0.8095	Intermediate Similarity	NPD2309	Approved
0.8088	Intermediate Similarity	NPD9717	Approved
0.8067	Intermediate Similarity	NPD920	Approved
0.8056	Intermediate Similarity	NPD3748	Approved
0.8054	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.8028	Intermediate Similarity	NPD943	Approved
0.8013	Intermediate Similarity	NPD919	Approved
0.8	Intermediate Similarity	NPD3818	Discontinued
0.7987	Intermediate Similarity	NPD6166	Phase 2
0.7987	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7959	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD5402	Approved
0.7911	Intermediate Similarity	NPD1247	Approved
0.7905	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7885	Intermediate Similarity	NPD7768	Phase 2
0.7883	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7883	Intermediate Similarity	NPD422	Phase 1
0.7875	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7853	Intermediate Similarity	NPD6797	Phase 2
0.7852	Intermediate Similarity	NPD1548	Phase 1
0.7823	Intermediate Similarity	NPD1471	Phase 3
0.7812	Intermediate Similarity	NPD3926	Phase 2
0.7808	Intermediate Similarity	NPD2799	Discontinued
0.7805	Intermediate Similarity	NPD7251	Discontinued
0.7793	Intermediate Similarity	NPD6651	Approved
0.7762	Intermediate Similarity	NPD2313	Discontinued
0.7758	Intermediate Similarity	NPD7808	Phase 3
0.7758	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD2935	Discontinued
0.7746	Intermediate Similarity	NPD6832	Phase 2
0.7736	Intermediate Similarity	NPD5494	Approved
0.7718	Intermediate Similarity	NPD2654	Approved
0.7697	Intermediate Similarity	NPD2532	Approved
0.7697	Intermediate Similarity	NPD2533	Approved
0.7697	Intermediate Similarity	NPD2534	Approved
0.7688	Intermediate Similarity	NPD6959	Discontinued
0.7687	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7687	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7636	Intermediate Similarity	NPD5953	Discontinued
0.7626	Intermediate Similarity	NPD1610	Phase 2
0.7622	Intermediate Similarity	NPD7054	Approved
0.7622	Intermediate Similarity	NPD7286	Phase 2
0.7591	Intermediate Similarity	NPD9545	Approved
0.759	Intermediate Similarity	NPD6559	Discontinued
0.7589	Intermediate Similarity	NPD3225	Approved
0.7576	Intermediate Similarity	NPD7472	Approved
0.7576	Intermediate Similarity	NPD7074	Phase 3
0.7574	Intermediate Similarity	NPD9493	Approved
0.755	Intermediate Similarity	NPD4628	Phase 3
0.7532	Intermediate Similarity	NPD1465	Phase 2
0.7517	Intermediate Similarity	NPD3268	Approved
0.7517	Intermediate Similarity	NPD6099	Approved
0.7517	Intermediate Similarity	NPD6100	Approved
0.7517	Intermediate Similarity	NPD1296	Phase 2
0.7517	Intermediate Similarity	NPD3764	Approved
0.7517	Intermediate Similarity	NPD411	Approved
0.75	Intermediate Similarity	NPD2354	Approved
0.75	Intermediate Similarity	NPD3226	Approved
0.7484	Intermediate Similarity	NPD2296	Approved
0.7483	Intermediate Similarity	NPD447	Suspended
0.7483	Intermediate Similarity	NPD2798	Approved
0.7481	Intermediate Similarity	NPD1241	Discontinued
0.747	Intermediate Similarity	NPD1729	Discontinued
0.745	Intermediate Similarity	NPD7033	Discontinued
0.745	Intermediate Similarity	NPD4308	Phase 3
0.7447	Intermediate Similarity	NPD1481	Phase 2
0.7447	Intermediate Similarity	NPD1608	Approved
0.7425	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD6232	Discontinued
0.7413	Intermediate Similarity	NPD2797	Approved
0.7394	Intermediate Similarity	NPD7473	Discontinued
0.7384	Intermediate Similarity	NPD4287	Approved
0.7379	Intermediate Similarity	NPD4908	Phase 1
0.7379	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD1535	Discovery
0.7375	Intermediate Similarity	NPD4288	Approved
0.7372	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD230	Phase 1
0.7365	Intermediate Similarity	NPD1933	Approved
0.7361	Intermediate Similarity	NPD1019	Discontinued
0.7351	Intermediate Similarity	NPD2346	Discontinued
0.7351	Intermediate Similarity	NPD2355	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD2353	Approved
0.7349	Intermediate Similarity	NPD3751	Discontinued
0.7333	Intermediate Similarity	NPD2403	Approved
0.733	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD3972	Approved
0.732	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD1470	Approved
0.7292	Intermediate Similarity	NPD3267	Approved
0.7292	Intermediate Similarity	NPD3266	Approved
0.7292	Intermediate Similarity	NPD1164	Approved
0.7279	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7279	Intermediate Similarity	NPD6798	Discontinued
0.7254	Intermediate Similarity	NPD1201	Approved
0.7248	Intermediate Similarity	NPD6355	Discontinued
0.7239	Intermediate Similarity	NPD74	Approved
0.7239	Intermediate Similarity	NPD9266	Approved
0.7234	Intermediate Similarity	NPD17	Approved
0.7229	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD5844	Phase 1
0.7197	Intermediate Similarity	NPD5049	Phase 3
0.7181	Intermediate Similarity	NPD4307	Phase 2
0.7181	Intermediate Similarity	NPD1613	Approved
0.7181	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7390	Discontinued
0.7175	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD4361	Phase 2
0.7169	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9267	Approved
0.7164	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD9263	Approved
0.7164	Intermediate Similarity	NPD9264	Approved
0.7161	Intermediate Similarity	NPD3887	Approved
0.7143	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD6233	Phase 2
0.7108	Intermediate Similarity	NPD5710	Approved
0.7108	Intermediate Similarity	NPD5711	Approved
0.7108	Intermediate Similarity	NPD3787	Discontinued
0.7103	Intermediate Similarity	NPD1876	Approved
0.7092	Intermediate Similarity	NPD1894	Discontinued
0.7076	Intermediate Similarity	NPD6104	Discontinued
0.7071	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD6279	Approved
0.7037	Intermediate Similarity	NPD6280	Approved
0.7022	Intermediate Similarity	NPD4360	Phase 2
0.7022	Intermediate Similarity	NPD4363	Phase 3
0.7006	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4062	Phase 3
0.698	Remote Similarity	NPD4625	Phase 3
0.6975	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD8434	Phase 2
0.697	Remote Similarity	NPD6971	Discontinued
0.6966	Remote Similarity	NPD9269	Phase 2
0.6959	Remote Similarity	NPD9494	Approved
0.6954	Remote Similarity	NPD3140	Approved
0.6954	Remote Similarity	NPD3142	Approved
0.6948	Remote Similarity	NPD5404	Approved
0.6948	Remote Similarity	NPD5405	Approved
0.6948	Remote Similarity	NPD5406	Approved
0.6948	Remote Similarity	NPD5408	Approved
0.6946	Remote Similarity	NPD7199	Phase 2
0.6943	Remote Similarity	NPD6190	Approved
0.6941	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD9281	Approved
0.6923	Remote Similarity	NPD4575	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD9268	Approved
0.6918	Remote Similarity	NPD4662	Approved
0.6918	Remote Similarity	NPD4661	Approved
0.6918	Remote Similarity	NPD4749	Approved
0.6908	Remote Similarity	NPD5124	Phase 1
0.6908	Remote Similarity	NPD4340	Discontinued
0.6908	Remote Similarity	NPD5123	Clinical (unspecified phase)

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