NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	227.09
Volume:	237.789
LogP:	3.115
LogD:	3.169
LogS:	-3.072
# Rotatable Bonds:	0
TPSA:	42.09
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.751
Synthetic Accessibility Score:	2.617
Fsp3:	0.214
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.811
MDCK Permeability:	2.8488586394814774e-05
Pgp-inhibitor:	0.508
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.018
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.249
Plasma Protein Binding (PPB):	94.7663345336914%
Volume Distribution (VD):	0.564
Pgp-substrate:	1.202121615409851%

ADMET: Metabolism

CYP1A2-inhibitor:	0.971
CYP1A2-substrate:	0.606
CYP2C19-inhibitor:	0.632
CYP2C19-substrate:	0.369
CYP2C9-inhibitor:	0.376
CYP2C9-substrate:	0.854
CYP2D6-inhibitor:	0.593
CYP2D6-substrate:	0.374
CYP3A4-inhibitor:	0.623
CYP3A4-substrate:	0.233

ADMET: Excretion

Clearance (CL):	2.996
Half-life (T1/2):	0.383

ADMET: Toxicity

hERG Blockers:	0.041
Human Hepatotoxicity (H-HT):	0.882
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.221
Rat Oral Acute Toxicity:	0.987
Maximum Recommended Daily Dose:	0.761
Skin Sensitization:	0.213
Carcinogencity:	0.874
Eye Corrosion:	0.003
Eye Irritation:	0.256
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC288943

Natural Product ID:	NPC288943
*Common Name:**	Flindersine
IUPAC Name:	2,2-dimethyl-6H-pyrano[3,2-c]quinolin-5-one
Synonyms:
Standard InCHIKey:	PXNMNABLQWUMCX-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C14H13NO2/c1-14(2)8-7-10-12(17-14)9-5-3-4-6-11(9)15-13(10)16/h3-8H,1-2H3,(H,15,16)
SMILES:	CC1(C)C=Cc2c(c3ccccc3nc2O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1507844
PubChem CID:	68230
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001253] Quinolines and derivatives [CHEMONTID:0000056] Quinolones and derivatives [CHEMONTID:0001291] Pyranoquinolines

*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
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(90)85209-X]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[10021943]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11277748]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921424]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	Hainan, China	n.a.	PMID[19091557]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	fruits	n.a.	n.a.	PMID[19902967]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23806071]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	China	n.a.	PMID[25115700]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26666037]
NPO40082	Conchocarpus fontanesianus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27557347]
NPO25406	Celastrus monospermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28006915]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798955]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28560	Sarcomelicope glauca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22790	Haplophyllum acutifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22790	Haplophyllum acutifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13313	Talipariti tiliaceum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28560	Sarcomelicope glauca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26378	Bistorta manshuriensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26701	Rhynchosia volubilis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3963	Hortonia floribunda	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25259	Schrebera swietenoides	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26690	Lactarius subpiperatus	Species	Lactariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26378	Bistorta manshuriensis	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26080	Ostracion lentiginosus	Species	Ostraciidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25794	Clerodendrum fragrans	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25802	Agave deserti	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24547	Xanthoria parietina	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9324	0techis scutatus	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26789	Tephrosia bidwilli	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22790	Haplophyllum acutifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26160	Thielavia terricola	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1267	Acronychia laurifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3494	Swietenia mahagoni	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26849	Parmelia zollingeri	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28560	Sarcomelicope glauca	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3005	Passiflora morifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26030	Fusarium asiaticum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13313	Talipariti tiliaceum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25833	Asclepias subulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28636	Vernonia lilacina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25998	Clusia congestiflora	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25406	Celastrus monospermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25358	Senecio gilliesi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25714	Solanum spirale	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22890	Eutrochium purpureum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22264	Inula salsoloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8245	Panulirus longipes	Species	Palinuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24918	Jacobaea cannabifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25201	Aglaia pyramidata	Species	Meliaceae	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	2
MIC	1
Others	13
Potency	5

Activity Type	# Activity
Individual Protein	3
NON-MOLECULAR	1
Organism	15
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT56	Individual Protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	112201.8	nM	PMID[458651]
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	19952.6	nM	PMID[458651]
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[458651]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	18526.0	nM	PMID[458651]
NPT2	Others	Unspecified		Potency	n.a.	707.9	nM	PMID[458651]
NPT2633	Organism	Selenastrum capricornutum	Selenastrum capricornutum	IC50	=	17800.0	nM	PMID[458652]
NPT2633	Organism	Selenastrum capricornutum	Selenastrum capricornutum	Activity	=	100.0	uM	PMID[458652]
NPT2633	Organism	Selenastrum capricornutum	Selenastrum capricornutum	Activity	=	10.0	uM	PMID[458652]
NPT2634	Organism	Pseudanabaena sp.	Pseudanabaena sp.	Activity	>	100.0	uM	PMID[458652]
NPT2635	Organism	Planktothrix agardhii	Planktothrix agardhii	Activity	>	100.0	uM	PMID[458652]
NPT2636	Organism	Oscillatoria perornata	Oscillatoria perornata	IC50	=	15900.0	nM	PMID[458652]
NPT2636	Organism	Oscillatoria perornata	Oscillatoria perornata	Activity	=	100.0	uM	PMID[458652]
NPT2636	Organism	Oscillatoria perornata	Oscillatoria perornata	Activity	=	10.0	uM	PMID[458652]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	Inhibition	<	40.0	%	PMID[458652]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	Inhibition	>	65.0	%	PMID[458652]
NPT852	Organism	Phomopsis obscurans	Phomopsis obscurans	Inhibition	>	80.0	%	PMID[458652]
NPT35	Others	n.a.		Solubility	n.a.	67600.0	nM	PMID[458653]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	15.0	ug	PMID[458654]

☑ 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 NPC288943 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	490
0.1-0.2	3503
0.2-0.3	13563
0.3-0.4	3470
0.4-0.5	14728
0.5-0.6	5183
0.6-0.7	1445
0.7-0.8	286
0.8-0.85	20
0.85-0.9	6
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9565	High Similarity	NPC283152
0.9458	High Similarity	NPC66083
0.8935	High Similarity	NPC62069
0.8772	High Similarity	NPC42591
0.8688	High Similarity	NPC26872
0.8642	High Similarity	NPC26850
0.8636	High Similarity	NPC279401
0.8636	High Similarity	NPC79293
0.8506	High Similarity	NPC61350
0.8373	Intermediate Similarity	NPC177404
0.8354	Intermediate Similarity	NPC60553
0.8315	Intermediate Similarity	NPC469390
0.8176	Intermediate Similarity	NPC285016
0.8162	Intermediate Similarity	NPC291535
0.8162	Intermediate Similarity	NPC475085
0.8162	Intermediate Similarity	NPC475112
0.8113	Intermediate Similarity	NPC280853
0.8066	Intermediate Similarity	NPC114335
0.8066	Intermediate Similarity	NPC141915
0.8066	Intermediate Similarity	NPC280964
0.8063	Intermediate Similarity	NPC245657
0.805	Intermediate Similarity	NPC471596
0.8042	Intermediate Similarity	NPC470931
0.8021	Intermediate Similarity	NPC469440
0.8	Intermediate Similarity	NPC118511
0.7989	Intermediate Similarity	NPC312872
0.7978	Intermediate Similarity	NPC320394
0.7937	Intermediate Similarity	NPC476106
0.7914	Intermediate Similarity	NPC471598
0.7889	Intermediate Similarity	NPC473449
0.788	Intermediate Similarity	NPC43787
0.788	Intermediate Similarity	NPC205934
0.7872	Intermediate Similarity	NPC66815
0.7849	Intermediate Similarity	NPC72211
0.7842	Intermediate Similarity	NPC304183
0.7838	Intermediate Similarity	NPC70259
0.7826	Intermediate Similarity	NPC471594
0.7818	Intermediate Similarity	NPC161292
0.7809	Intermediate Similarity	NPC168486
0.7809	Intermediate Similarity	NPC222592
0.7796	Intermediate Similarity	NPC243834
0.7796	Intermediate Similarity	NPC70956
0.779	Intermediate Similarity	NPC204385
0.779	Intermediate Similarity	NPC194040
0.7784	Intermediate Similarity	NPC48353
0.7778	Intermediate Similarity	NPC84478
0.7766	Intermediate Similarity	NPC11017
0.7759	Intermediate Similarity	NPC44161
0.773	Intermediate Similarity	NPC289786
0.7701	Intermediate Similarity	NPC224928
0.7667	Intermediate Similarity	NPC206201
0.7656	Intermediate Similarity	NPC472111
0.7654	Intermediate Similarity	NPC72980
0.7644	Intermediate Similarity	NPC223427
0.7644	Intermediate Similarity	NPC162484
0.7633	Intermediate Similarity	NPC153769
0.7632	Intermediate Similarity	NPC267423
0.7632	Intermediate Similarity	NPC476044
0.7629	Intermediate Similarity	NPC209769
0.7627	Intermediate Similarity	NPC474409
0.7624	Intermediate Similarity	NPC176127
0.7611	Intermediate Similarity	NPC478032
0.7609	Intermediate Similarity	NPC110741
0.7604	Intermediate Similarity	NPC137929
0.7604	Intermediate Similarity	NPC164374
0.7602	Intermediate Similarity	NPC203168
0.7592	Intermediate Similarity	NPC135887
0.7592	Intermediate Similarity	NPC199277
0.759	Intermediate Similarity	NPC219664
0.759	Intermediate Similarity	NPC269367
0.7586	Intermediate Similarity	NPC473057
0.7553	Intermediate Similarity	NPC473053
0.7542	Intermediate Similarity	NPC194724
0.7538	Intermediate Similarity	NPC469589
0.7537	Intermediate Similarity	NPC97746
0.7529	Intermediate Similarity	NPC47298
0.7529	Intermediate Similarity	NPC315214
0.75	Intermediate Similarity	NPC473822
0.7487	Intermediate Similarity	NPC475910
0.7486	Intermediate Similarity	NPC159319
0.7486	Intermediate Similarity	NPC32028
0.7486	Intermediate Similarity	NPC303225
0.7475	Intermediate Similarity	NPC477532
0.7473	Intermediate Similarity	NPC144114
0.7458	Intermediate Similarity	NPC278874
0.7449	Intermediate Similarity	NPC201697
0.7448	Intermediate Similarity	NPC470586
0.7437	Intermediate Similarity	NPC16066
0.7436	Intermediate Similarity	NPC193777
0.7435	Intermediate Similarity	NPC128823
0.7435	Intermediate Similarity	NPC280714
0.7432	Intermediate Similarity	NPC212535
0.743	Intermediate Similarity	NPC208060
0.7429	Intermediate Similarity	NPC224632
0.7426	Intermediate Similarity	NPC469439
0.7426	Intermediate Similarity	NPC128115
0.7416	Intermediate Similarity	NPC477888
0.7407	Intermediate Similarity	NPC131017
0.7405	Intermediate Similarity	NPC314573
0.7396	Intermediate Similarity	NPC329747
0.7391	Intermediate Similarity	NPC190007
0.7387	Intermediate Similarity	NPC471080
0.7387	Intermediate Similarity	NPC469592
0.7377	Intermediate Similarity	NPC118776
0.7376	Intermediate Similarity	NPC213530
0.7376	Intermediate Similarity	NPC193267
0.7374	Intermediate Similarity	NPC476688
0.7374	Intermediate Similarity	NPC476686
0.7374	Intermediate Similarity	NPC105758
0.7371	Intermediate Similarity	NPC285635
0.7368	Intermediate Similarity	NPC251090
0.7363	Intermediate Similarity	NPC88363
0.7363	Intermediate Similarity	NPC472168
0.7351	Intermediate Similarity	NPC94943
0.7337	Intermediate Similarity	NPC112206
0.7337	Intermediate Similarity	NPC202605
0.7333	Intermediate Similarity	NPC118832
0.7333	Intermediate Similarity	NPC47059
0.7333	Intermediate Similarity	NPC470930
0.7333	Intermediate Similarity	NPC329708
0.7333	Intermediate Similarity	NPC165349
0.7333	Intermediate Similarity	NPC285558
0.7333	Intermediate Similarity	NPC264166
0.7333	Intermediate Similarity	NPC274291
0.733	Intermediate Similarity	NPC267928
0.733	Intermediate Similarity	NPC200888
0.7327	Intermediate Similarity	NPC469594
0.7326	Intermediate Similarity	NPC242928
0.732	Intermediate Similarity	NPC295898
0.7318	Intermediate Similarity	NPC473764
0.7318	Intermediate Similarity	NPC126481
0.7318	Intermediate Similarity	NPC314940
0.7317	Intermediate Similarity	NPC205372
0.7314	Intermediate Similarity	NPC84508
0.7303	Intermediate Similarity	NPC108469
0.7291	Intermediate Similarity	NPC148409
0.7291	Intermediate Similarity	NPC298436
0.7283	Intermediate Similarity	NPC470474
0.7283	Intermediate Similarity	NPC474798
0.7283	Intermediate Similarity	NPC477891
0.7282	Intermediate Similarity	NPC317572
0.7273	Intermediate Similarity	NPC174758
0.7273	Intermediate Similarity	NPC174672
0.7268	Intermediate Similarity	NPC232727
0.7263	Intermediate Similarity	NPC230403
0.7263	Intermediate Similarity	NPC475190
0.7263	Intermediate Similarity	NPC307963
0.726	Intermediate Similarity	NPC252251
0.725	Intermediate Similarity	NPC264176
0.7247	Intermediate Similarity	NPC471178
0.7241	Intermediate Similarity	NPC173080
0.724	Intermediate Similarity	NPC474188
0.7238	Intermediate Similarity	NPC259545
0.7238	Intermediate Similarity	NPC471294
0.7225	Intermediate Similarity	NPC209174
0.7216	Intermediate Similarity	NPC234197
0.7216	Intermediate Similarity	NPC315957
0.7216	Intermediate Similarity	NPC329793
0.7213	Intermediate Similarity	NPC211997
0.7211	Intermediate Similarity	NPC195268
0.7211	Intermediate Similarity	NPC133140
0.7209	Intermediate Similarity	NPC288445
0.7208	Intermediate Similarity	NPC474145
0.7208	Intermediate Similarity	NPC475841
0.72	Intermediate Similarity	NPC141353
0.72	Intermediate Similarity	NPC87413
0.7191	Intermediate Similarity	NPC97367
0.719	Intermediate Similarity	NPC477531
0.7189	Intermediate Similarity	NPC219963
0.7189	Intermediate Similarity	NPC161887
0.7189	Intermediate Similarity	NPC266551
0.7188	Intermediate Similarity	NPC13880
0.7184	Intermediate Similarity	NPC36168
0.7182	Intermediate Similarity	NPC258773
0.7182	Intermediate Similarity	NPC14651
0.7182	Intermediate Similarity	NPC121658
0.7181	Intermediate Similarity	NPC46580
0.7172	Intermediate Similarity	NPC193238
0.7171	Intermediate Similarity	NPC174049
0.7167	Intermediate Similarity	NPC1527
0.7165	Intermediate Similarity	NPC18487
0.7158	Intermediate Similarity	NPC134586
0.7158	Intermediate Similarity	NPC84347
0.7157	Intermediate Similarity	NPC476581
0.7157	Intermediate Similarity	NPC16452
0.7157	Intermediate Similarity	NPC36229
0.7143	Intermediate Similarity	NPC8022
0.7143	Intermediate Similarity	NPC470799
0.7143	Intermediate Similarity	NPC296527
0.7136	Intermediate Similarity	NPC287208
0.7136	Intermediate Similarity	NPC82548
0.7135	Intermediate Similarity	NPC59779
0.7135	Intermediate Similarity	NPC124542
0.7135	Intermediate Similarity	NPC471177
0.7129	Intermediate Similarity	NPC478074
0.7128	Intermediate Similarity	NPC19872
0.7128	Intermediate Similarity	NPC176538
0.7128	Intermediate Similarity	NPC249040
0.7127	Intermediate Similarity	NPC476518
0.7127	Intermediate Similarity	NPC164664

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 NPC288943 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	314
0.1-0.2	731
0.2-0.3	854
0.3-0.4	1138
0.4-0.5	2860
0.5-0.6	2353
0.6-0.7	786
0.7-0.8	108
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8391	Intermediate Similarity	NPD5083	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD4203	Approved
0.8382	Intermediate Similarity	NPD4204	Approved
0.8324	Intermediate Similarity	NPD4305	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD1503	Clinical (unspecified phase)
0.8235	Intermediate Similarity	NPD4724	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD6491	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD6590	Discontinued
0.788	Intermediate Similarity	NPD6861	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD7222	Phase 2
0.7797	Intermediate Similarity	NPD6159	Phase 2
0.7742	Intermediate Similarity	NPD5512	Phase 3
0.773	Intermediate Similarity	NPD6361	Phase 2
0.7654	Intermediate Similarity	NPD3920	Phase 2
0.7644	Intermediate Similarity	NPD6991	Approved
0.7617	Intermediate Similarity	NPD7453	Approved
0.7617	Intermediate Similarity	NPD7452	Approved
0.7606	Intermediate Similarity	NPD6988	Phase 1
0.7594	Intermediate Similarity	NPD3810	Clinical (unspecified phase)
0.7581	Intermediate Similarity	NPD6569	Phase 2
0.7557	Intermediate Similarity	NPD6872	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD6550	Discontinued
0.7537	Intermediate Similarity	NPD3925	Approved
0.7529	Intermediate Similarity	NPD1685	Approved
0.7529	Intermediate Similarity	NPD2882	Phase 1
0.7529	Intermediate Similarity	NPD1684	Approved
0.7526	Intermediate Similarity	NPD1768	Approved
0.7513	Intermediate Similarity	NPD6769	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD4418	Discontinued
0.75	Intermediate Similarity	NPD5256	Discontinued
0.75	Intermediate Similarity	NPD648	Clinical (unspecified phase)
0.7487	Intermediate Similarity	NPD7672	Approved
0.7487	Intermediate Similarity	NPD7671	Approved
0.7474	Intermediate Similarity	NPD3003	Approved
0.7474	Intermediate Similarity	NPD5530	Phase 1
0.7473	Intermediate Similarity	NPD3037	Phase 1
0.7473	Intermediate Similarity	NPD3386	Phase 2
0.7446	Intermediate Similarity	NPD4889	Approved
0.7437	Intermediate Similarity	NPD5417	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD5429	Discontinued
0.7433	Intermediate Similarity	NPD2334	Discontinued
0.7427	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7427	Intermediate Similarity	NPD6158	Phase 2
0.7407	Intermediate Similarity	NPD3395	Approved
0.7407	Intermediate Similarity	NPD3396	Approved
0.7377	Intermediate Similarity	NPD7414	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD6220	Phase 3
0.7374	Intermediate Similarity	NPD4502	Phase 2
0.7366	Intermediate Similarity	NPD2383	Phase 1
0.7363	Intermediate Similarity	NPD1620	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7069	Discontinued
0.7333	Intermediate Similarity	NPD4035	Approved
0.7333	Intermediate Similarity	NPD4033	Approved
0.7333	Intermediate Similarity	NPD4034	Approved
0.7333	Intermediate Similarity	NPD4038	Approved
0.7333	Intermediate Similarity	NPD32	Approved
0.7333	Intermediate Similarity	NPD4037	Approved
0.7333	Intermediate Similarity	NPD31	Approved
0.7333	Intermediate Similarity	NPD4122	Approved
0.7333	Intermediate Similarity	NPD4036	Approved
0.7333	Intermediate Similarity	NPD4039	Approved
0.733	Intermediate Similarity	NPD1622	Discontinued
0.7316	Intermediate Similarity	NPD6251	Discontinued
0.7308	Intermediate Similarity	NPD5751	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD4396	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD3842	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6150	Discontinued
0.7291	Intermediate Similarity	NPD3875	Discontinued
0.7286	Intermediate Similarity	NPD5416	Discontinued
0.7282	Intermediate Similarity	NPD6246	Approved
0.7277	Intermediate Similarity	NPD3477	Phase 2
0.7277	Intermediate Similarity	NPD3478	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD5902	Approved
0.7264	Intermediate Similarity	NPD5903	Approved
0.7263	Intermediate Similarity	NPD1038	Approved
0.7263	Intermediate Similarity	NPD4551	Phase 2
0.7259	Intermediate Similarity	NPD1392	Approved
0.7258	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4118	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD925	Approved
0.7247	Intermediate Similarity	NPD926	Approved
0.724	Intermediate Similarity	NPD2952	Discontinued
0.7228	Intermediate Similarity	NPD2433	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD3324	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD5658	Approved
0.7219	Intermediate Similarity	NPD4375	Approved
0.7216	Intermediate Similarity	NPD1739	Approved
0.7216	Intermediate Similarity	NPD1740	Approved
0.7211	Intermediate Similarity	NPD3921	Approved
0.7211	Intermediate Similarity	NPD3924	Approved
0.7211	Intermediate Similarity	NPD3923	Approved
0.7211	Intermediate Similarity	NPD3922	Approved
0.7206	Intermediate Similarity	NPD7194	Discontinued
0.7202	Intermediate Similarity	NPD7889	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD9690	Approved
0.7179	Intermediate Similarity	NPD6592	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6985	Discontinued
0.7157	Intermediate Similarity	NPD4795	Phase 2
0.715	Intermediate Similarity	NPD4673	Phase 2
0.7143	Intermediate Similarity	NPD4021	Phase 2
0.7143	Intermediate Similarity	NPD6208	Discontinued
0.712	Intermediate Similarity	NPD3503	Approved
0.712	Intermediate Similarity	NPD4372	Phase 1
0.712	Intermediate Similarity	NPD3504	Approved
0.7113	Intermediate Similarity	NPD2727	Phase 2
0.7105	Intermediate Similarity	NPD2410	Phase 2
0.7101	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD7538	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD5930	Phase 3
0.7079	Intermediate Similarity	NPD112	Approved
0.7079	Intermediate Similarity	NPD9705	Discontinued
0.7077	Intermediate Similarity	NPD2175	Phase 3
0.7077	Intermediate Similarity	NPD2177	Approved
0.7077	Intermediate Similarity	NPD2176	Approved
0.7074	Intermediate Similarity	NPD2762	Phase 2
0.7073	Intermediate Similarity	NPD7395	Discontinued
0.7062	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD1229	Phase 2
0.7059	Intermediate Similarity	NPD5612	Discontinued
0.7049	Intermediate Similarity	NPD677	Clinical (unspecified phase)
0.7042	Intermediate Similarity	NPD7558	Phase 2
0.7042	Intermediate Similarity	NPD6494	Phase 2
0.703	Intermediate Similarity	NPD5067	Phase 2
0.703	Intermediate Similarity	NPD5066	Phase 2
0.7027	Intermediate Similarity	NPD4071	Approved
0.7027	Intermediate Similarity	NPD1032	Phase 2
0.7027	Intermediate Similarity	NPD4072	Approved
0.7018	Intermediate Similarity	NPD3525	Discontinued
0.7015	Intermediate Similarity	NPD4437	Phase 3
0.7011	Intermediate Similarity	NPD6492	Phase 2
0.701	Intermediate Similarity	NPD6140	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD4897	Phase 2
0.7	Intermediate Similarity	NPD7674	Phase 3
0.7	Intermediate Similarity	NPD6257	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1034	Phase 3
0.7	Intermediate Similarity	NPD7676	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7426	Phase 1
0.7	Intermediate Similarity	NPD7675	Phase 3
0.7	Intermediate Similarity	NPD1033	Clinical (unspecified phase)
0.6985	Remote Similarity	NPD3397	Phase 2
0.6985	Remote Similarity	NPD3946	Clinical (unspecified phase)
0.6976	Remote Similarity	NPD6147	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5003	Discontinued
0.697	Remote Similarity	NPD5669	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD2582	Approved
0.6966	Remote Similarity	NPD2581	Approved
0.6963	Remote Similarity	NPD9714	Clinical (unspecified phase)
0.695	Remote Similarity	NPD4901	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7703	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6938	Remote Similarity	NPD7219	Approved
0.6938	Remote Similarity	NPD7221	Approved
0.6938	Remote Similarity	NPD1954	Phase 1
0.6936	Remote Similarity	NPD1305	Clinical (unspecified phase)
0.6935	Remote Similarity	NPD6641	Approved
0.6935	Remote Similarity	NPD6642	Approved
0.6927	Remote Similarity	NPD6060	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD5255	Approved
0.6915	Remote Similarity	NPD6290	Phase 2
0.6912	Remote Similarity	NPD3816	Phase 1
0.6912	Remote Similarity	NPD3815	Phase 1
0.6911	Remote Similarity	NPD2749	Discontinued
0.6909	Remote Similarity	NPD4350	Approved
0.6909	Remote Similarity	NPD4349	Approved
0.6907	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7548	Discontinued
0.6904	Remote Similarity	NPD3825	Phase 3
0.6902	Remote Similarity	NPD1078	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD4900	Clinical (unspecified phase)
0.6895	Remote Similarity	NPD6227	Discontinued
0.6891	Remote Similarity	NPD1924	Approved
0.6887	Remote Similarity	NPD6326	Phase 2
0.6887	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6327	Phase 1
0.6887	Remote Similarity	NPD6553	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD2781	Approved
0.6882	Remote Similarity	NPD4354	Approved
0.6882	Remote Similarity	NPD5100	Phase 3
0.6881	Remote Similarity	NPD2916	Discontinued
0.6881	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD5945	Phase 1
0.6878	Remote Similarity	NPD5944	Phase 1
0.6875	Remote Similarity	NPD408	Approved
0.6875	Remote Similarity	NPD4334	Discontinued
0.6872	Remote Similarity	NPD6247	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD6962	Phase 2
0.6868	Remote Similarity	NPD2782	Approved
0.6868	Remote Similarity	NPD2780	Approved
0.6866	Remote Similarity	NPD8403	Phase 1
0.6866	Remote Similarity	NPD3932	Clinical (unspecified phase)
0.6865	Remote Similarity	NPD3224	Phase 2
0.6861	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.686	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.686	Remote Similarity	NPD1592	Phase 3
0.685	Remote Similarity	NPD6324	Phase 1

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