NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	258.05
Volume:	250.527
LogP:	2.99
LogD:	2.123
LogS:	-3.452
# Rotatable Bonds:	1
TPSA:	90.9
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.461
Synthetic Accessibility Score:	2.727
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:	-5.018
MDCK Permeability:	1.2012060324195772e-05
Pgp-inhibitor:	0.062
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.229
20% Bioavailability (F20%):	0.048
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	95.10094451904297%
Volume Distribution (VD):	0.574
Pgp-substrate:	10.643951416015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.978
CYP1A2-substrate:	0.427
CYP2C19-inhibitor:	0.18
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.672
CYP2C9-substrate:	0.669
CYP2D6-inhibitor:	0.618
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.172
CYP3A4-substrate:	0.102

ADMET: Excretion

Clearance (CL):	4.565
Half-life (T1/2):	0.854

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.121
Drug-inuced Liver Injury (DILI):	0.975
AMES Toxicity:	0.664
Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.612
Skin Sensitization:	0.85
Carcinogencity:	0.669
Eye Corrosion:	0.004
Eye Irritation:	0.9
Respiratory Toxicity:	0.368

Download Data

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

Natural Product: NPC217602

Natural Product ID:	NPC217602
*Common Name:**	(S)-5-Hydroxy-2-(1-Hydroxyethyl)Naphtho[2,3-B]Furan-4,9-Dione
IUPAC Name:	5-hydroxy-2-[(1S)-1-hydroxyethyl]benzo[f][1]benzofuran-4,9-dione
Synonyms:
Standard InCHIKey:	XJGFVZBTNKODFQ-LURJTMIESA-N
Standard InCHI:	InChI=1S/C14H10O5/c1-6(15)10-5-8-12(17)11-7(3-2-4-9(11)16)13(18)14(8)19-10/h2-6,15-16H,1H3/t6-/m0/s1
SMILES:	C[C@@H](c1cc2C(=O)c3c(cccc3O)C(=O)c2o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL392591
PubChem CID:	14159819
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
NPO30968	Tabebuia impetiginosa	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/P19910002323]
NPO31330	Tabebuia ochracea	Species	Bignoniaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1076/phbi.35.4.227.13306]
NPO30050	Tabebuia incana	Species	Bignoniaceae	Eukaryota	n.a.	bark	n.a.	DOI[10.1590/S0044-59672007000100011]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	bark	n.a.	PMID[17950604]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	Brazilian	n.a.	PMID[19674905]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32044231]
NPO12083	Hydnellum zonatum	Species	Thelephoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO487	Tabebuia avellanedae	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3751	Orthantha lutea	n.a.	n.a.	n.a.	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
EC50	16
IC50	6
MIC	12
Others	28

Activity Type	# Activity
Cell Line	15
Individual Protein	8
Organism	17
Others	22

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT306	Cell Line	PC-3	Homo sapiens	EC50	=	140.0	nM	PMID[537952]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	960.0	nM	PMID[537952]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	3500.0	nM	PMID[537952]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[537952]
NPT80	Cell Line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[537952]
NPT306	Cell Line	PC-3	Homo sapiens	EC50	=	140.0	nM	PMID[537953]
NPT83	Cell Line	MCF7	Homo sapiens	EC50	=	510.0	nM	PMID[537953]
NPT81	Cell Line	A549	Homo sapiens	EC50	=	780.0	nM	PMID[537953]
NPT611	Cell Line	Hepatocyte	Homo sapiens	EC50	=	11100.0	nM	PMID[537953]
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[537953]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Inhibition	=	100.0	%	PMID[537954]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	410.0	nM	PMID[537954]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	500.0	nM	PMID[537954]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	130.0	nM	PMID[537954]
NPT1689	Individual Protein	Tyrosine-protein kinase JAK1	Homo sapiens	Inhibition	=	94.8	%	PMID[537954]
NPT3246	Individual Protein	Tyrosine-protein kinase JAK2	Homo sapiens	Inhibition	=	80.6	%	PMID[537954]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	IC50	=	2000.0	nM	PMID[537954]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Activity	=	76.0	%	PMID[537954]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Activity	=	75.0	%	PMID[537954]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Activity	=	43.0	%	PMID[537954]
NPT38	Individual Protein	Signal transducer and activator of transcription 3	Homo sapiens	Activity	=	3.0	%	PMID[537954]
NPT27	Others	Unspecified		EC50	=	11100.0	nM	PMID[537952]
NPT27	Others	Unspecified		EC50	=	29700.0	nM	PMID[537952]
NPT27	Others	Unspecified		EC50	=	54500.0	nM	PMID[537952]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	0.0	%	PMID[537952]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	4.4	%	PMID[537952]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	16.9	%	PMID[537952]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	50.0	%	PMID[537952]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	IC50	=	33200.0	nM	PMID[537952]
NPT2	Others	Unspecified		Activity	=	67.0	%	PMID[537953]
NPT2	Others	Unspecified		Activity	=	7.0	%	PMID[537953]
NPT2	Others	Unspecified		Activity	=	47.0	%	PMID[537953]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	0.78	ug.mL-1	PMID[537953]
NPT3658	Organism	Bacillus mycoides	Bacillus mycoides	MIC	=	0.78	ug.mL-1	PMID[537953]
NPT3657	Organism	Cryptococcus albidus	Cryptococcus albidus	MIC	=	1.56	ug.mL-1	PMID[537953]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	3.13	ug.mL-1	PMID[537953]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	MIC	=	3.13	ug.mL-1	PMID[537953]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	=	12.5	ug.mL-1	PMID[537953]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	25.0	ug.mL-1	PMID[537953]
NPT3086	Organism	Penicillium expansum	Penicillium expansum	MIC	=	25.0	ug.mL-1	PMID[537953]
NPT3656	Organism	Paecilomyces variotii	Paecilomyces variotii	MIC	=	25.0	ug.mL-1	PMID[537953]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100.0	ug.mL-1	PMID[537953]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	100.0	ug.mL-1	PMID[537953]
NPT3608	Organism	Salmonella enteritidis	Salmonella enterica subsp. enterica serovar Enteritidis	MIC	>	100.0	ug.mL-1	PMID[537953]
NPT27	Others	Unspecified		EC50	=	3360.0	nM	PMID[537953]
NPT27	Others	Unspecified		EC50	=	5510.0	nM	PMID[537953]
NPT27	Others	Unspecified		EC50	=	11100.0	nM	PMID[537953]
NPT27	Others	Unspecified		EC50	=	29700.0	nM	PMID[537953]
NPT27	Others	Unspecified		EC50	=	54500.0	nM	PMID[537953]
NPT2	Others	Unspecified		IC50	=	33200.0	nM	PMID[537953]
NPT2	Others	Unspecified		Activity	=	50.0	%	PMID[537953]
NPT2	Others	Unspecified		Activity	=	16.9	%	PMID[537953]
NPT2	Others	Unspecified		Activity	=	4.4	%	PMID[537953]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[537953]
NPT2	Others	Unspecified		Activity	=	3.9	n.a.	PMID[537953]
NPT2	Others	Unspecified		Activity	=	68.0	%	PMID[537954]
NPT2	Others	Unspecified		Activity	=	78.0	%	PMID[537954]
NPT2	Others	Unspecified		Activity	=	21.0	%	PMID[537954]
NPT2	Others	Unspecified		Activity	=	35.0	%	PMID[537954]

☑ 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 NPC217602 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	386
0.1-0.2	1603
0.2-0.3	3557
0.3-0.4	8837
0.4-0.5	9707
0.5-0.6	4139
0.6-0.7	6306
0.7-0.8	7082
0.8-0.85	1036
0.85-0.9	31
0.9-0.95	4
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC473282
1.0	High Similarity	NPC104380
0.9867	High Similarity	NPC317900
0.9867	High Similarity	NPC476404
0.9867	High Similarity	NPC294300
0.9664	High Similarity	NPC471613
0.953	High Similarity	NPC226578
0.9333	High Similarity	NPC280025
0.9267	High Similarity	NPC252208
0.8931	High Similarity	NPC269117
0.8792	High Similarity	NPC265181
0.8773	High Similarity	NPC186392
0.8688	High Similarity	NPC228501
0.8659	High Similarity	NPC95715
0.8659	High Similarity	NPC44602
0.8645	High Similarity	NPC469425
0.8625	High Similarity	NPC10051
0.8625	High Similarity	NPC299094
0.8608	High Similarity	NPC275878
0.8571	High Similarity	NPC469385
0.8562	High Similarity	NPC478223
0.8554	High Similarity	NPC28042
0.8554	High Similarity	NPC315306
0.8554	High Similarity	NPC313717
0.8553	High Similarity	NPC88958
0.8553	High Similarity	NPC158261
0.8553	High Similarity	NPC42458
0.8553	High Similarity	NPC290927
0.8529	High Similarity	NPC475996
0.8519	High Similarity	NPC472961
0.8519	High Similarity	NPC472962
0.8485	Intermediate Similarity	NPC53640
0.8476	Intermediate Similarity	NPC472581
0.8466	Intermediate Similarity	NPC478134
0.8466	Intermediate Similarity	NPC472780
0.8466	Intermediate Similarity	NPC472783
0.8466	Intermediate Similarity	NPC24761
0.8452	Intermediate Similarity	NPC277510
0.8452	Intermediate Similarity	NPC477409
0.8438	Intermediate Similarity	NPC179170
0.8438	Intermediate Similarity	NPC84721
0.8428	Intermediate Similarity	NPC115324
0.8415	Intermediate Similarity	NPC219861
0.8415	Intermediate Similarity	NPC193998
0.8412	Intermediate Similarity	NPC5671
0.8411	Intermediate Similarity	NPC141934
0.8405	Intermediate Similarity	NPC472782
0.8405	Intermediate Similarity	NPC472781
0.8405	Intermediate Similarity	NPC470810
0.8405	Intermediate Similarity	NPC313368
0.8395	Intermediate Similarity	NPC96342
0.8395	Intermediate Similarity	NPC164110
0.8395	Intermediate Similarity	NPC246647
0.8395	Intermediate Similarity	NPC212967
0.8385	Intermediate Similarity	NPC148938
0.8385	Intermediate Similarity	NPC268008
0.8383	Intermediate Similarity	NPC202470
0.8375	Intermediate Similarity	NPC60211
0.8375	Intermediate Similarity	NPC207624
0.8373	Intermediate Similarity	NPC191012
0.8372	Intermediate Similarity	NPC228209
0.8366	Intermediate Similarity	NPC477408
0.8366	Intermediate Similarity	NPC114620
0.8366	Intermediate Similarity	NPC103337
0.8364	Intermediate Similarity	NPC1706
0.8364	Intermediate Similarity	NPC39305
0.8364	Intermediate Similarity	NPC109180
0.8364	Intermediate Similarity	NPC59295
0.8364	Intermediate Similarity	NPC1755
0.8364	Intermediate Similarity	NPC263092
0.8354	Intermediate Similarity	NPC96031
0.8354	Intermediate Similarity	NPC45124
0.8354	Intermediate Similarity	NPC74854
0.8354	Intermediate Similarity	NPC218569
0.8354	Intermediate Similarity	NPC30655
0.8344	Intermediate Similarity	NPC476349
0.8344	Intermediate Similarity	NPC477410
0.8344	Intermediate Similarity	NPC476350
0.8344	Intermediate Similarity	NPC471346
0.8343	Intermediate Similarity	NPC30550
0.8333	Intermediate Similarity	NPC180924
0.8323	Intermediate Similarity	NPC476459
0.8323	Intermediate Similarity	NPC235333
0.8313	Intermediate Similarity	NPC314653
0.8313	Intermediate Similarity	NPC474772
0.8313	Intermediate Similarity	NPC58668
0.8313	Intermediate Similarity	NPC193976
0.8313	Intermediate Similarity	NPC175617
0.8313	Intermediate Similarity	NPC472784
0.8313	Intermediate Similarity	NPC136641
0.8313	Intermediate Similarity	NPC156244
0.8313	Intermediate Similarity	NPC106372
0.8313	Intermediate Similarity	NPC472423
0.8313	Intermediate Similarity	NPC23668
0.8313	Intermediate Similarity	NPC316262
0.8313	Intermediate Similarity	NPC145830
0.8313	Intermediate Similarity	NPC302783
0.8313	Intermediate Similarity	NPC472049
0.8313	Intermediate Similarity	NPC473201
0.8313	Intermediate Similarity	NPC474744
0.8303	Intermediate Similarity	NPC272722
0.8303	Intermediate Similarity	NPC238995
0.8302	Intermediate Similarity	NPC478219
0.8294	Intermediate Similarity	NPC289244
0.8293	Intermediate Similarity	NPC304839
0.8293	Intermediate Similarity	NPC220582
0.8291	Intermediate Similarity	NPC21835
0.8284	Intermediate Similarity	NPC91650
0.8282	Intermediate Similarity	NPC477833
0.8282	Intermediate Similarity	NPC201127
0.828	Intermediate Similarity	NPC73416
0.828	Intermediate Similarity	NPC98926
0.828	Intermediate Similarity	NPC160777
0.8274	Intermediate Similarity	NPC473096
0.8274	Intermediate Similarity	NPC473095
0.8272	Intermediate Similarity	NPC213936
0.8272	Intermediate Similarity	NPC297531
0.8272	Intermediate Similarity	NPC80489
0.8266	Intermediate Similarity	NPC8927
0.8263	Intermediate Similarity	NPC472895
0.8263	Intermediate Similarity	NPC477517
0.8261	Intermediate Similarity	NPC154683
0.8261	Intermediate Similarity	NPC35567
0.8261	Intermediate Similarity	NPC142308
0.8261	Intermediate Similarity	NPC253872
0.8261	Intermediate Similarity	NPC471347
0.8261	Intermediate Similarity	NPC243171
0.8261	Intermediate Similarity	NPC40356
0.8261	Intermediate Similarity	NPC171651
0.8261	Intermediate Similarity	NPC285623
0.8261	Intermediate Similarity	NPC471349
0.8261	Intermediate Similarity	NPC67654
0.8261	Intermediate Similarity	NPC304954
0.8256	Intermediate Similarity	NPC104682
0.8253	Intermediate Similarity	NPC476931
0.8253	Intermediate Similarity	NPC475779
0.8253	Intermediate Similarity	NPC472582
0.825	Intermediate Similarity	NPC202595
0.825	Intermediate Similarity	NPC260582
0.825	Intermediate Similarity	NPC267117
0.825	Intermediate Similarity	NPC255641
0.825	Intermediate Similarity	NPC290954
0.825	Intermediate Similarity	NPC472421
0.8247	Intermediate Similarity	NPC1268
0.8242	Intermediate Similarity	NPC476929
0.8239	Intermediate Similarity	NPC295436
0.8235	Intermediate Similarity	NPC154986
0.8235	Intermediate Similarity	NPC98776
0.8232	Intermediate Similarity	NPC287559
0.8229	Intermediate Similarity	NPC240808
0.8228	Intermediate Similarity	NPC1940
0.8228	Intermediate Similarity	NPC148011
0.8221	Intermediate Similarity	NPC472461
0.8221	Intermediate Similarity	NPC160015
0.8221	Intermediate Similarity	NPC247677
0.8221	Intermediate Similarity	NPC221992
0.8217	Intermediate Similarity	NPC19896
0.8214	Intermediate Similarity	NPC473094
0.8214	Intermediate Similarity	NPC150131
0.8214	Intermediate Similarity	NPC241820
0.8214	Intermediate Similarity	NPC247973
0.821	Intermediate Similarity	NPC189130
0.821	Intermediate Similarity	NPC208806
0.821	Intermediate Similarity	NPC303950
0.821	Intermediate Similarity	NPC27532
0.821	Intermediate Similarity	NPC301233
0.821	Intermediate Similarity	NPC256346
0.821	Intermediate Similarity	NPC472786
0.821	Intermediate Similarity	NPC203080
0.821	Intermediate Similarity	NPC474000
0.821	Intermediate Similarity	NPC214632
0.821	Intermediate Similarity	NPC293286
0.821	Intermediate Similarity	NPC246328
0.821	Intermediate Similarity	NPC325028
0.8204	Intermediate Similarity	NPC45449
0.8204	Intermediate Similarity	NPC36320
0.8199	Intermediate Similarity	NPC262038
0.8199	Intermediate Similarity	NPC470569
0.8199	Intermediate Similarity	NPC132990
0.8199	Intermediate Similarity	NPC319910
0.8199	Intermediate Similarity	NPC230848
0.8199	Intermediate Similarity	NPC262039
0.8199	Intermediate Similarity	NPC170169
0.8199	Intermediate Similarity	NPC254412
0.8199	Intermediate Similarity	NPC472580
0.8199	Intermediate Similarity	NPC278476
0.8199	Intermediate Similarity	NPC46882
0.8199	Intermediate Similarity	NPC471229
0.8198	Intermediate Similarity	NPC23553
0.8198	Intermediate Similarity	NPC77179
0.8194	Intermediate Similarity	NPC477537
0.8193	Intermediate Similarity	NPC212099
0.8193	Intermediate Similarity	NPC278329
0.8193	Intermediate Similarity	NPC101116
0.8193	Intermediate Similarity	NPC478229
0.8193	Intermediate Similarity	NPC211107
0.8193	Intermediate Similarity	NPC472402
0.8193	Intermediate Similarity	NPC146837
0.8192	Intermediate Similarity	NPC60848
0.8187	Intermediate Similarity	NPC296030

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 NPC217602 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	341
0.1-0.2	943
0.2-0.3	1676
0.3-0.4	2624
0.4-0.5	1910
0.5-0.6	1062
0.6-0.7	423
0.7-0.8	161
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8792	High Similarity	NPD1471	Phase 3
0.8333	Intermediate Similarity	NPD3882	Suspended
0.8301	Intermediate Similarity	NPD2344	Approved
0.8187	Intermediate Similarity	NPD3226	Approved
0.8089	Intermediate Similarity	NPD2309	Approved
0.8061	Intermediate Similarity	NPD7075	Discontinued
0.8024	Intermediate Similarity	NPD1247	Approved
0.8	Intermediate Similarity	NPD8434	Phase 2
0.7988	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD1934	Approved
0.7927	Intermediate Similarity	NPD6801	Discontinued
0.7914	Intermediate Similarity	NPD6599	Discontinued
0.7911	Intermediate Similarity	NPD4628	Phase 3
0.7898	Intermediate Similarity	NPD1549	Phase 2
0.7879	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD6799	Approved
0.7834	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7826	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD3926	Phase 2
0.7821	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD6559	Discontinued
0.7805	Intermediate Similarity	NPD4380	Phase 2
0.7798	Intermediate Similarity	NPD919	Approved
0.7791	Intermediate Similarity	NPD3818	Discontinued
0.7778	Intermediate Similarity	NPD1512	Approved
0.7778	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6166	Phase 2
0.7771	Intermediate Similarity	NPD7819	Suspended
0.7738	Intermediate Similarity	NPD3749	Approved
0.7736	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7725	Intermediate Similarity	NPD5402	Approved
0.7725	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD2346	Discontinued
0.7707	Intermediate Similarity	NPD1510	Phase 2
0.7692	Intermediate Similarity	NPD1607	Approved
0.7688	Intermediate Similarity	NPD7893	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD3751	Discontinued
0.7682	Intermediate Similarity	NPD1470	Approved
0.7677	Intermediate Similarity	NPD1240	Approved
0.7665	Intermediate Similarity	NPD2801	Approved
0.7654	Intermediate Similarity	NPD1511	Approved
0.7647	Intermediate Similarity	NPD5494	Approved
0.7644	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7633	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7622	Intermediate Similarity	NPD5403	Approved
0.7619	Intermediate Similarity	NPD3817	Phase 2
0.7607	Intermediate Similarity	NPD2532	Approved
0.7607	Intermediate Similarity	NPD5401	Approved
0.7607	Intermediate Similarity	NPD2534	Approved
0.7607	Intermediate Similarity	NPD2533	Approved
0.7602	Intermediate Similarity	NPD6959	Discontinued
0.7588	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD6232	Discontinued
0.7557	Intermediate Similarity	NPD6797	Phase 2
0.7547	Intermediate Similarity	NPD2796	Approved
0.7545	Intermediate Similarity	NPD7411	Suspended
0.7529	Intermediate Similarity	NPD7473	Discontinued
0.7528	Intermediate Similarity	NPD8313	Approved
0.7528	Intermediate Similarity	NPD8312	Approved
0.7516	Intermediate Similarity	NPD2800	Approved
0.7515	Intermediate Similarity	NPD920	Approved
0.7515	Intermediate Similarity	NPD2296	Approved
0.7514	Intermediate Similarity	NPD7251	Discontinued
0.75	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2163	Approved
0.7484	Intermediate Similarity	NPD2799	Discontinued
0.7484	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7472	Intermediate Similarity	NPD7808	Phase 3
0.7472	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7471	Intermediate Similarity	NPD4575	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD4060	Phase 1
0.7443	Intermediate Similarity	NPD5844	Phase 1
0.7438	Intermediate Similarity	NPD1551	Phase 2
0.7433	Intermediate Similarity	NPD6779	Approved
0.7433	Intermediate Similarity	NPD6780	Approved
0.7433	Intermediate Similarity	NPD6781	Approved
0.7433	Intermediate Similarity	NPD6777	Approved
0.7433	Intermediate Similarity	NPD6782	Approved
0.7433	Intermediate Similarity	NPD6776	Approved
0.7433	Intermediate Similarity	NPD6778	Approved
0.7417	Intermediate Similarity	NPD1201	Approved
0.7417	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD7435	Discontinued
0.7407	Intermediate Similarity	NPD1243	Approved
0.7405	Intermediate Similarity	NPD6355	Discontinued
0.7401	Intermediate Similarity	NPD7074	Phase 3
0.7394	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD5762	Approved
0.7391	Intermediate Similarity	NPD5763	Approved
0.7378	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7362	Intermediate Similarity	NPD3750	Approved
0.7356	Intermediate Similarity	NPD6808	Phase 2
0.7356	Intermediate Similarity	NPD3787	Discontinued
0.7353	Intermediate Similarity	NPD5761	Phase 2
0.7353	Intermediate Similarity	NPD5760	Phase 2
0.7345	Intermediate Similarity	NPD7054	Approved
0.7329	Intermediate Similarity	NPD2935	Discontinued
0.7325	Intermediate Similarity	NPD2313	Discontinued
0.7322	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD6765	Approved
0.7318	Intermediate Similarity	NPD6764	Approved
0.7308	Intermediate Similarity	NPD8150	Discontinued
0.7303	Intermediate Similarity	NPD7472	Approved
0.7294	Intermediate Similarity	NPD6279	Approved
0.7294	Intermediate Similarity	NPD6280	Approved
0.7263	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1608	Approved
0.7253	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD1465	Phase 2
0.7246	Intermediate Similarity	NPD6273	Approved
0.7233	Intermediate Similarity	NPD943	Approved
0.7226	Intermediate Similarity	NPD1203	Approved
0.7225	Intermediate Similarity	NPD7698	Approved
0.7225	Intermediate Similarity	NPD7696	Phase 3
0.7225	Intermediate Similarity	NPD7697	Approved
0.7219	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD6798	Discontinued
0.7215	Intermediate Similarity	NPD3764	Approved
0.7188	Intermediate Similarity	NPD7871	Phase 2
0.7188	Intermediate Similarity	NPD447	Suspended
0.7188	Intermediate Similarity	NPD7870	Phase 2
0.7186	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD7874	Approved
0.7179	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7168	Intermediate Similarity	NPD7768	Phase 2
0.7166	Intermediate Similarity	NPD6534	Approved
0.7166	Intermediate Similarity	NPD6535	Approved
0.7165	Intermediate Similarity	NPD7701	Phase 2
0.7161	Intermediate Similarity	NPD1876	Approved
0.716	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD7033	Discontinued
0.7158	Intermediate Similarity	NPD6784	Approved
0.7158	Intermediate Similarity	NPD6785	Approved
0.7134	Intermediate Similarity	NPD9494	Approved
0.7133	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7118	Intermediate Similarity	NPD2649	Approved
0.7118	Intermediate Similarity	NPD2651	Approved
0.7108	Intermediate Similarity	NPD2354	Approved
0.7088	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD9092	Discovery
0.7083	Intermediate Similarity	NPD4661	Approved
0.7083	Intermediate Similarity	NPD4662	Approved
0.7072	Intermediate Similarity	NPD5953	Discontinued
0.707	Intermediate Similarity	NPD2798	Approved
0.7068	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD5710	Approved
0.7062	Intermediate Similarity	NPD5711	Approved
0.7059	Intermediate Similarity	NPD17	Approved
0.7056	Intermediate Similarity	NPD7801	Approved
0.7055	Intermediate Similarity	NPD3748	Approved
0.7053	Intermediate Similarity	NPD7700	Phase 2
0.7053	Intermediate Similarity	NPD7699	Phase 2
0.7032	Intermediate Similarity	NPD3972	Approved
0.7032	Intermediate Similarity	NPD9717	Approved
0.7024	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD7458	Discontinued
0.7012	Intermediate Similarity	NPD6099	Approved
0.7012	Intermediate Similarity	NPD6100	Approved
0.701	Intermediate Similarity	NPD8319	Approved
0.701	Intermediate Similarity	NPD8320	Phase 1
0.7006	Intermediate Similarity	NPD7199	Phase 2
0.7006	Intermediate Similarity	NPD3887	Approved
0.7006	Intermediate Similarity	NPD6190	Approved
0.7	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD411	Approved
0.7	Intermediate Similarity	NPD7177	Discontinued
0.7	Intermediate Similarity	NPD3268	Approved
0.6995	Remote Similarity	NPD3057	Approved
0.6994	Remote Similarity	NPD37	Approved
0.6994	Remote Similarity	NPD6844	Discontinued
0.6989	Remote Similarity	NPD6234	Discontinued
0.6983	Remote Similarity	NPD2403	Approved
0.6981	Remote Similarity	NPD6832	Phase 2
0.6975	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6971	Remote Similarity	NPD4967	Phase 2
0.6971	Remote Similarity	NPD4966	Approved
0.6971	Remote Similarity	NPD4965	Approved
0.6943	Remote Similarity	NPD1283	Approved
0.6941	Remote Similarity	NPD5049	Phase 3
0.6928	Remote Similarity	NPD9545	Approved
0.6914	Remote Similarity	NPD1613	Approved
0.6914	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5616	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD2972	Approved
0.6907	Remote Similarity	NPD3533	Approved
0.6907	Remote Similarity	NPD6823	Phase 2
0.6894	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6886	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6883	Remote Similarity	NPD1651	Approved
0.6882	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD8404	Phase 2

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