NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	242.06
Volume:	241.737
LogP:	2.861
LogD:	2.149
LogS:	-3.446
# Rotatable Bonds:	1
TPSA:	70.67
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.507
Synthetic Accessibility Score:	2.471
Fsp3:	0.071
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:	-4.942
MDCK Permeability:	1.6023581338231452e-05
Pgp-inhibitor:	0.137
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.045
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.018
Plasma Protein Binding (PPB):	95.66523742675781%
Volume Distribution (VD):	0.551
Pgp-substrate:	8.527486801147461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.982
CYP1A2-substrate:	0.343
CYP2C19-inhibitor:	0.398
CYP2C19-substrate:	0.106
CYP2C9-inhibitor:	0.59
CYP2C9-substrate:	0.593
CYP2D6-inhibitor:	0.632
CYP2D6-substrate:	0.295
CYP3A4-inhibitor:	0.185
CYP3A4-substrate:	0.123

ADMET: Excretion

Clearance (CL):	4.548
Half-life (T1/2):	0.811

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.165
Drug-inuced Liver Injury (DILI):	0.974
AMES Toxicity:	0.546
Rat Oral Acute Toxicity:	0.335
Maximum Recommended Daily Dose:	0.582
Skin Sensitization:	0.819
Carcinogencity:	0.826
Eye Corrosion:	0.003
Eye Irritation:	0.805
Respiratory Toxicity:	0.661

Download Data

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

Natural Product: NPC471613

Natural Product ID:	NPC471613
*Common Name:**	2-(1-Hydroethyl)Naphtho[2,3-B]Furan-4,9-Dione
IUPAC Name:	2-(1-hydroxyethyl)benzo[f][1]benzofuran-4,9-dione
Synonyms:
Standard InCHIKey:	SAXKEWRSGLPYPB-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H10O4/c1-7(15)11-6-10-12(16)8-4-2-3-5-9(8)13(17)14(10)18-11/h2-7,15H,1H3
SMILES:	CC(c1cc2C(=O)c3ccccc3C(=O)c2o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL294323
PubChem CID:	150068
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001634] Naphthofurans

*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
NPO20768	Ekmanianthe longiflora	Species	Bignoniaceae	Eukaryota	roots	n.a.	n.a.	PMID[10785421]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000047]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309308]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7153777]
NPO29177	Crescentia cujete	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8254347]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29177	Crescentia cujete	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16767	Kigelia pinnata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29177	Crescentia cujete	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20768	Ekmanianthe longiflora	Species	Bignoniaceae	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
ED50	13
IC50	16
MIC	1
Others	9

Activity Type	# Activity
Cell Line	23
NON-MOLECULAR	7
Organism	7
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[550583]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	8.9	uM	PMID[550584]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	1.8	ug ml-1	PMID[550585]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	0.5	ug ml-1	PMID[550585]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	3.5	ug ml-1	PMID[550585]
NPT2345	Cell Line	SW626	Homo sapiens	ED50	=	0.3	ug ml-1	PMID[550585]
NPT136	Cell Line	SK-N-SH	Homo sapiens	ED50	=	4.0	ug ml-1	PMID[550585]
NPT726	Cell Line	M109	Mus musculus	ED50	=	1.8	ug ml-1	PMID[550585]
NPT168	Cell Line	P388	Mus musculus	T/C	=	110.0	%	PMID[550585]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	2.0	ug ml-1	PMID[550586]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	0.41	ug.mL-1	PMID[550587]
NPT1851	Cell Line	Col2	Homo sapiens	IC50	=	7400.0	nM	PMID[550588]
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2100.0	nM	PMID[550588]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	=	14500.0	nM	PMID[550588]
NPT1034	Cell Line	Lu1	Homo sapiens	IC50	=	800.0	nM	PMID[550588]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	2500.0	nM	PMID[550588]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	IC50	=	1200.0	nM	PMID[550588]
NPT168	Cell Line	P388	Mus musculus	IC50	=	400.0	nM	PMID[550588]
NPT2345	Cell Line	SW626	Homo sapiens	IC50	=	1200.0	nM	PMID[550588]
NPT1034	Cell Line	Lu1	Homo sapiens	Inhibition	=	0.0	%	PMID[550588]
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	3000.0	nM	PMID[550589]
NPT941	Cell Line	HaCaT	Homo sapiens	IC50	=	3700.0	nM	PMID[550590]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	627.0	nM	PMID[550584]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	718.0	nM	PMID[550584]
NPT27	Others	Unspecified		Ratio	=	6.18	n.a.	PMID[550584]
NPT27	Others	Unspecified		Ratio	=	5.4	n.a.	PMID[550584]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	3.2	ug ml-1	PMID[550585]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	0.2	ug ml-1	PMID[550585]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	1.2	ug ml-1	PMID[550585]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	2.0	ug ml-1	PMID[550585]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	14.0	ug ml-1	PMID[550587]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	180.0	ug ml-1	PMID[550587]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	13200.0	nM	PMID[550588]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	4900.0	nM	PMID[550588]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	-0.4	g	PMID[550588]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	14.0	ug ml-1	PMID[550589]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	15000.0	nM	PMID[550589]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	41200.0	nM	PMID[550592]

☑ 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 NPC471613 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	370
0.1-0.2	1527
0.2-0.3	3416
0.3-0.4	8583
0.4-0.5	10251
0.5-0.6	4639
0.6-0.7	6756
0.7-0.8	6980
0.8-0.85	144
0.85-0.9	20
0.9-0.95	2
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9664	High Similarity	NPC473282
0.9664	High Similarity	NPC317900
0.9664	High Similarity	NPC104380
0.9664	High Similarity	NPC294300
0.9664	High Similarity	NPC476404
0.9664	High Similarity	NPC217602
0.9655	High Similarity	NPC280025
0.9195	High Similarity	NPC226578
0.9097	High Similarity	NPC265181
0.906	High Similarity	NPC252208
0.8831	High Similarity	NPC88958
0.8812	High Similarity	NPC44602
0.8782	High Similarity	NPC299094
0.8782	High Similarity	NPC10051
0.8616	High Similarity	NPC472780
0.8616	High Similarity	NPC269117
0.8616	High Similarity	NPC472783
0.859	High Similarity	NPC179170
0.8562	High Similarity	NPC469425
0.8553	High Similarity	NPC472781
0.8553	High Similarity	NPC472782
0.8471	Intermediate Similarity	NPC158261
0.8471	Intermediate Similarity	NPC42458
0.8466	Intermediate Similarity	NPC186392
0.8462	Intermediate Similarity	NPC145830
0.8457	Intermediate Similarity	NPC472784
0.8408	Intermediate Similarity	NPC275878
0.8395	Intermediate Similarity	NPC475779
0.8387	Intermediate Similarity	NPC192069
0.8375	Intermediate Similarity	NPC287559
0.8375	Intermediate Similarity	NPC228501
0.8366	Intermediate Similarity	NPC469385
0.8365	Intermediate Similarity	NPC221992
0.8354	Intermediate Similarity	NPC95715
0.8354	Intermediate Similarity	NPC472786
0.8323	Intermediate Similarity	NPC18986
0.8313	Intermediate Similarity	NPC140952
0.8301	Intermediate Similarity	NPC117674
0.8282	Intermediate Similarity	NPC121995
0.8282	Intermediate Similarity	NPC472581
0.8278	Intermediate Similarity	NPC18904
0.8278	Intermediate Similarity	NPC477408
0.8267	Intermediate Similarity	NPC177262
0.8253	Intermediate Similarity	NPC313717
0.8253	Intermediate Similarity	NPC315306
0.8253	Intermediate Similarity	NPC28042
0.825	Intermediate Similarity	NPC81405
0.825	Intermediate Similarity	NPC478223
0.8247	Intermediate Similarity	NPC93241
0.8247	Intermediate Similarity	NPC27798
0.8239	Intermediate Similarity	NPC84721
0.8239	Intermediate Similarity	NPC75310
0.8239	Intermediate Similarity	NPC290927
0.8235	Intermediate Similarity	NPC475996
0.8221	Intermediate Similarity	NPC219861
0.8221	Intermediate Similarity	NPC56358
0.8214	Intermediate Similarity	NPC472665
0.821	Intermediate Similarity	NPC472961
0.821	Intermediate Similarity	NPC472962
0.8182	Intermediate Similarity	NPC53640
0.8182	Intermediate Similarity	NPC191012
0.8176	Intermediate Similarity	NPC60211
0.8171	Intermediate Similarity	NPC109180
0.817	Intermediate Similarity	NPC52412
0.816	Intermediate Similarity	NPC478134
0.816	Intermediate Similarity	NPC24761
0.8155	Intermediate Similarity	NPC277510
0.8148	Intermediate Similarity	NPC476350
0.8148	Intermediate Similarity	NPC476349
0.8141	Intermediate Similarity	NPC471346
0.8141	Intermediate Similarity	NPC281398
0.8133	Intermediate Similarity	NPC476459
0.8129	Intermediate Similarity	NPC477409
0.8121	Intermediate Similarity	NPC136641
0.8121	Intermediate Similarity	NPC270312
0.8118	Intermediate Similarity	NPC5671
0.8113	Intermediate Similarity	NPC475777
0.8113	Intermediate Similarity	NPC472423
0.8113	Intermediate Similarity	NPC474772
0.8113	Intermediate Similarity	NPC175617
0.8113	Intermediate Similarity	NPC474744
0.8113	Intermediate Similarity	NPC115324
0.8113	Intermediate Similarity	NPC156244
0.8113	Intermediate Similarity	NPC121615
0.8113	Intermediate Similarity	NPC294511
0.811	Intermediate Similarity	NPC193998
0.8105	Intermediate Similarity	NPC477537
0.8098	Intermediate Similarity	NPC313368
0.8098	Intermediate Similarity	NPC470810
0.8089	Intermediate Similarity	NPC478018
0.8086	Intermediate Similarity	NPC212967
0.8086	Intermediate Similarity	NPC472823
0.8086	Intermediate Similarity	NPC96342
0.8086	Intermediate Similarity	NPC164110
0.8086	Intermediate Similarity	NPC116639
0.8086	Intermediate Similarity	NPC246647
0.8084	Intermediate Similarity	NPC202470
0.8081	Intermediate Similarity	NPC228209
0.8079	Intermediate Similarity	NPC141934
0.8079	Intermediate Similarity	NPC232996
0.8077	Intermediate Similarity	NPC160777
0.8077	Intermediate Similarity	NPC233763
0.8077	Intermediate Similarity	NPC73416
0.8075	Intermediate Similarity	NPC148938
0.8075	Intermediate Similarity	NPC478159
0.8075	Intermediate Similarity	NPC268008
0.8075	Intermediate Similarity	NPC478161
0.8072	Intermediate Similarity	NPC472895
0.8072	Intermediate Similarity	NPC296558
0.807	Intermediate Similarity	NPC104682
0.8063	Intermediate Similarity	NPC207624
0.8063	Intermediate Similarity	NPC67654
0.8063	Intermediate Similarity	NPC471349
0.8063	Intermediate Similarity	NPC471347
0.8063	Intermediate Similarity	NPC171651
0.8063	Intermediate Similarity	NPC263676
0.8063	Intermediate Similarity	NPC35567
0.8063	Intermediate Similarity	NPC243171
0.8063	Intermediate Similarity	NPC285623
0.8061	Intermediate Similarity	NPC263092
0.8061	Intermediate Similarity	NPC1755
0.8061	Intermediate Similarity	NPC59295
0.8061	Intermediate Similarity	NPC1706
0.8061	Intermediate Similarity	NPC39305
0.8061	Intermediate Similarity	NPC476931
0.805	Intermediate Similarity	NPC472421
0.805	Intermediate Similarity	NPC144010
0.805	Intermediate Similarity	NPC267117
0.8049	Intermediate Similarity	NPC96031
0.8049	Intermediate Similarity	NPC74854
0.8049	Intermediate Similarity	NPC283209
0.8049	Intermediate Similarity	NPC476929
0.8049	Intermediate Similarity	NPC45124
0.8049	Intermediate Similarity	NPC30655
0.8047	Intermediate Similarity	NPC30550
0.8039	Intermediate Similarity	NPC114620
0.8039	Intermediate Similarity	NPC90296
0.8039	Intermediate Similarity	NPC103337
0.8038	Intermediate Similarity	NPC218569
0.8037	Intermediate Similarity	NPC477410
0.8025	Intermediate Similarity	NPC7059
0.8025	Intermediate Similarity	NPC1940
0.8025	Intermediate Similarity	NPC148011
0.8025	Intermediate Similarity	NPC247677
0.8025	Intermediate Similarity	NPC180924
0.8025	Intermediate Similarity	NPC160015
0.8024	Intermediate Similarity	NPC150131
0.8013	Intermediate Similarity	NPC114513
0.8013	Intermediate Similarity	NPC245522
0.8012	Intermediate Similarity	NPC474000
0.8012	Intermediate Similarity	NPC314653
0.8012	Intermediate Similarity	NPC472049
0.8012	Intermediate Similarity	NPC203080
0.8012	Intermediate Similarity	NPC316262
0.8012	Intermediate Similarity	NPC472785
0.8012	Intermediate Similarity	NPC235333
0.8012	Intermediate Similarity	NPC469966
0.8012	Intermediate Similarity	NPC293286
0.8	Intermediate Similarity	NPC272722
0.8	Intermediate Similarity	NPC262038
0.8	Intermediate Similarity	NPC243577
0.8	Intermediate Similarity	NPC261184
0.8	Intermediate Similarity	NPC473201
0.8	Intermediate Similarity	NPC278476
0.8	Intermediate Similarity	NPC58668
0.8	Intermediate Similarity	NPC472664
0.8	Intermediate Similarity	NPC106372
0.8	Intermediate Similarity	NPC289244
0.8	Intermediate Similarity	NPC319910
0.8	Intermediate Similarity	NPC302783
0.8	Intermediate Similarity	NPC238995
0.8	Intermediate Similarity	NPC472580
0.8	Intermediate Similarity	NPC64568
0.8	Intermediate Similarity	NPC193976
0.8	Intermediate Similarity	NPC262039
0.8	Intermediate Similarity	NPC471229
0.8	Intermediate Similarity	NPC23668
0.8	Intermediate Similarity	NPC254412
0.7988	Intermediate Similarity	NPC91650
0.7988	Intermediate Similarity	NPC43490
0.7988	Intermediate Similarity	NPC69028
0.7988	Intermediate Similarity	NPC220582
0.7988	Intermediate Similarity	NPC329938
0.7988	Intermediate Similarity	NPC306978
0.7988	Intermediate Similarity	NPC475107
0.7988	Intermediate Similarity	NPC68848
0.7988	Intermediate Similarity	NPC79571
0.7988	Intermediate Similarity	NPC472584
0.7988	Intermediate Similarity	NPC169
0.7988	Intermediate Similarity	NPC304839
0.7988	Intermediate Similarity	NPC263432
0.7988	Intermediate Similarity	NPC118128
0.7987	Intermediate Similarity	NPC228842
0.7987	Intermediate Similarity	NPC296030
0.7987	Intermediate Similarity	NPC277032
0.7987	Intermediate Similarity	NPC205360
0.7987	Intermediate Similarity	NPC478219
0.7987	Intermediate Similarity	NPC477535
0.7987	Intermediate Similarity	NPC39929
0.7977	Intermediate Similarity	NPC8927

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 NPC471613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	340
0.1-0.2	930
0.2-0.3	1560
0.3-0.4	2651
0.4-0.5	2014
0.5-0.6	1111
0.6-0.7	403
0.7-0.8	138
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9097	High Similarity	NPD1471	Phase 3
0.8212	Intermediate Similarity	NPD2344	Approved
0.8129	Intermediate Similarity	NPD8434	Phase 2
0.8025	Intermediate Similarity	NPD3882	Suspended
0.8	Intermediate Similarity	NPD2309	Approved
0.7987	Intermediate Similarity	NPD3226	Approved
0.7935	Intermediate Similarity	NPD4628	Phase 3
0.7901	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7075	Discontinued
0.784	Intermediate Similarity	NPD6801	Discontinued
0.7831	Intermediate Similarity	NPD1247	Approved
0.7826	Intermediate Similarity	NPD6599	Discontinued
0.7785	Intermediate Similarity	NPD6799	Approved
0.7711	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD1549	Phase 2
0.7643	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD3926	Phase 2
0.7628	Intermediate Similarity	NPD2346	Discontinued
0.7628	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD1934	Approved
0.7607	Intermediate Similarity	NPD4380	Phase 2
0.7605	Intermediate Similarity	NPD919	Approved
0.7602	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD7819	Suspended
0.7545	Intermediate Similarity	NPD3749	Approved
0.7542	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD5403	Approved
0.753	Intermediate Similarity	NPD5402	Approved
0.753	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD6559	Discontinued
0.7516	Intermediate Similarity	NPD5401	Approved
0.7516	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1510	Phase 2
0.75	Intermediate Similarity	NPD2799	Discontinued
0.75	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD3751	Discontinued
0.7485	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD6166	Phase 2
0.7484	Intermediate Similarity	NPD1607	Approved
0.747	Intermediate Similarity	NPD5760	Phase 2
0.747	Intermediate Similarity	NPD5761	Phase 2
0.7469	Intermediate Similarity	NPD1512	Approved
0.7468	Intermediate Similarity	NPD1240	Approved
0.7467	Intermediate Similarity	NPD1470	Approved
0.7457	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD5494	Approved
0.7455	Intermediate Similarity	NPD7411	Suspended
0.7452	Intermediate Similarity	NPD2796	Approved
0.744	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7429	Intermediate Similarity	NPD6765	Approved
0.7429	Intermediate Similarity	NPD6764	Approved
0.7425	Intermediate Similarity	NPD3817	Phase 2
0.7425	Intermediate Similarity	NPD2296	Approved
0.7423	Intermediate Similarity	NPD920	Approved
0.7419	Intermediate Similarity	NPD6355	Discontinued
0.7368	Intermediate Similarity	NPD6808	Phase 2
0.7365	Intermediate Similarity	NPD2801	Approved
0.7346	Intermediate Similarity	NPD1511	Approved
0.7338	Intermediate Similarity	NPD2313	Discontinued
0.7329	Intermediate Similarity	NPD9092	Discovery
0.7312	Intermediate Similarity	NPD1243	Approved
0.7312	Intermediate Similarity	NPD2800	Approved
0.731	Intermediate Similarity	NPD6959	Discontinued
0.7305	Intermediate Similarity	NPD6280	Approved
0.7305	Intermediate Similarity	NPD6279	Approved
0.7301	Intermediate Similarity	NPD2532	Approved
0.7301	Intermediate Similarity	NPD2534	Approved
0.7301	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD2533	Approved
0.7299	Intermediate Similarity	NPD2163	Approved
0.7296	Intermediate Similarity	NPD5762	Approved
0.7296	Intermediate Similarity	NPD5763	Approved
0.7285	Intermediate Similarity	NPD1876	Approved
0.7284	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD6797	Phase 2
0.7267	Intermediate Similarity	NPD6232	Discontinued
0.7263	Intermediate Similarity	NPD6785	Approved
0.7263	Intermediate Similarity	NPD6784	Approved
0.7257	Intermediate Similarity	NPD5844	Phase 1
0.7256	Intermediate Similarity	NPD6273	Approved
0.725	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD8312	Approved
0.7247	Intermediate Similarity	NPD8313	Approved
0.7244	Intermediate Similarity	NPD4060	Phase 1
0.7241	Intermediate Similarity	NPD7473	Discontinued
0.7233	Intermediate Similarity	NPD1551	Phase 2
0.7232	Intermediate Similarity	NPD7251	Discontinued
0.7226	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD2354	Approved
0.72	Intermediate Similarity	NPD1201	Approved
0.7195	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD7808	Phase 3
0.7184	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD3787	Discontinued
0.7166	Intermediate Similarity	NPD6779	Approved
0.7166	Intermediate Similarity	NPD6777	Approved
0.7166	Intermediate Similarity	NPD6776	Approved
0.7166	Intermediate Similarity	NPD6782	Approved
0.7166	Intermediate Similarity	NPD6778	Approved
0.7166	Intermediate Similarity	NPD6781	Approved
0.7166	Intermediate Similarity	NPD6780	Approved
0.716	Intermediate Similarity	NPD3750	Approved
0.7152	Intermediate Similarity	NPD1608	Approved
0.7152	Intermediate Similarity	NPD3972	Approved
0.7143	Intermediate Similarity	NPD7435	Discontinued
0.7126	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD2935	Discontinued
0.7124	Intermediate Similarity	NPD1203	Approved
0.7119	Intermediate Similarity	NPD7074	Phase 3
0.7117	Intermediate Similarity	NPD3887	Approved
0.7115	Intermediate Similarity	NPD3764	Approved
0.7091	Intermediate Similarity	NPD4662	Approved
0.7091	Intermediate Similarity	NPD4661	Approved
0.7089	Intermediate Similarity	NPD447	Suspended
0.7078	Intermediate Similarity	NPD2798	Approved
0.7076	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD7033	Discontinued
0.7062	Intermediate Similarity	NPD7054	Approved
0.7055	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD9717	Approved
0.7033	Intermediate Similarity	NPD8150	Discontinued
0.7032	Intermediate Similarity	NPD9494	Approved
0.7025	Intermediate Similarity	NPD943	Approved
0.7024	Intermediate Similarity	NPD2651	Approved
0.7024	Intermediate Similarity	NPD7458	Discontinued
0.7024	Intermediate Similarity	NPD2649	Approved
0.7022	Intermediate Similarity	NPD7472	Approved
0.7006	Intermediate Similarity	NPD3268	Approved
0.6988	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6832	Phase 2
0.6983	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD7768	Phase 2
0.6975	Remote Similarity	NPD2353	Approved
0.6975	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.697	Remote Similarity	NPD8404	Phase 2
0.6968	Remote Similarity	NPD5647	Approved
0.6963	Remote Similarity	NPD7697	Approved
0.6963	Remote Similarity	NPD7696	Phase 3
0.6963	Remote Similarity	NPD7698	Approved
0.6962	Remote Similarity	NPD6233	Phase 2
0.6962	Remote Similarity	NPD4062	Phase 3
0.6959	Remote Similarity	NPD1465	Phase 2
0.6957	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD3748	Approved
0.6954	Remote Similarity	NPD17	Approved
0.6948	Remote Similarity	NPD1283	Approved
0.6946	Remote Similarity	NPD5049	Phase 3
0.6939	Remote Similarity	NPD1241	Discontinued
0.6932	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6928	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD7870	Phase 2
0.6927	Remote Similarity	NPD7871	Phase 2
0.6923	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7874	Approved
0.6913	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD7701	Phase 2
0.6906	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD37	Approved
0.6901	Remote Similarity	NPD6844	Discontinued
0.6899	Remote Similarity	NPD411	Approved
0.6898	Remote Similarity	NPD6534	Approved
0.6898	Remote Similarity	NPD6535	Approved
0.6895	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6893	Remote Similarity	NPD2403	Approved
0.6889	Remote Similarity	NPD5953	Discontinued
0.6887	Remote Similarity	NPD1651	Approved
0.6879	Remote Similarity	NPD4965	Approved
0.6879	Remote Similarity	NPD4967	Phase 2
0.6879	Remote Similarity	NPD4966	Approved
0.6875	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD4308	Phase 3
0.6848	Remote Similarity	NPD7003	Approved
0.6835	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7095	Approved
0.6829	Remote Similarity	NPD4534	Discontinued
0.6829	Remote Similarity	NPD2424	Discontinued
0.6829	Remote Similarity	NPD5958	Discontinued
0.6825	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6823	Remote Similarity	NPD3057	Approved
0.6821	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD9545	Approved
0.6818	Remote Similarity	NPD7199	Phase 2
0.6818	Remote Similarity	NPD8127	Discontinued
0.6816	Remote Similarity	NPD7177	Discontinued
0.6807	Remote Similarity	NPD6190	Approved
0.6802	Remote Similarity	NPD7801	Approved
0.68	Remote Similarity	NPD6234	Discontinued
0.6795	Remote Similarity	NPD3267	Approved
0.6795	Remote Similarity	NPD3266	Approved
0.6792	Remote Similarity	NPD1699	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