NPASS Compound

Structure

CID200246 OpenBabel06191715592D 24 27 0 0 0 0 0 0 0 0999 V2000 -1.8320 -0.7588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 0.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 4 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 5 6 2 0 0 0 0 5 8 1 0 0 0 0 6 18 1 0 0 0 0 7 11 2 0 0 0 0 7 12 1 0 0 0 0 8 11 1 0 0 0 0 8 14 2 0 0 0 0 9 15 1 0 0 0 0 9 17 2 0 0 0 0 10 16 2 0 0 0 0 10 19 1 0 0 0 0 11 24 1 0 0 0 0 12 13 2 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 22 1 0 0 0 0 17 23 1 0 0 0 0 18 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.08
Volume:	317.308
LogP:	3.92
LogD:	2.536
LogS:	-3.643
# Rotatable Bonds:	0
TPSA:	100.13
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.433
Synthetic Accessibility Score:	3.024
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.899
MDCK Permeability:	1.82864059752319e-05
Pgp-inhibitor:	0.745
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.058
20% Bioavailability (F20%):	0.005
30% Bioavailability (F30%):	0.064

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012
Plasma Protein Binding (PPB):	96.68595123291016%
Volume Distribution (VD):	0.536
Pgp-substrate:	9.070840835571289%

ADMET: Metabolism

CYP1A2-inhibitor:	0.873
CYP1A2-substrate:	0.462
CYP2C19-inhibitor:	0.123
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.765
CYP2C9-substrate:	0.747
CYP2D6-inhibitor:	0.5
CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	0.235
CYP3A4-substrate:	0.107

ADMET: Excretion

Clearance (CL):	2.204
Half-life (T1/2):	0.728

ADMET: Toxicity

hERG Blockers:	0.004
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.981
AMES Toxicity:	0.557
Rat Oral Acute Toxicity:	0.456
Maximum Recommended Daily Dose:	0.871
Skin Sensitization:	0.895
Carcinogencity:	0.86
Eye Corrosion:	0.003
Eye Irritation:	0.756
Respiratory Toxicity:	0.459

Download Data

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

Natural Product: NPC200246

Natural Product ID:	NPC200246
*Common Name:**	Jacareubin
IUPAC Name:	5,9,10-trihydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
Synonyms:	Jacareubin
Standard InCHIKey:	UCLUVPCGXYTYEK-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O6/c1-18(2)6-5-8-11(24-18)7-12-13(14(8)20)15(21)9-3-4-10(19)16(22)17(9)23-12/h3-7,19-20,22H,1-2H3
SMILES:	CC1(C)C=Cc2c(cc3c(c2O)c(=O)c2ccc(c(c2o3)O)O)O1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1254294
PubChem CID:	5281644
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003521] Pyranoxanthones

*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
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[11908963]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12662094]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104480]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15340243]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15678383]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16045947]
NPO22503	Salix matsudana	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18794770]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO15264	Garcinia paucinervis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20594858]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	Chinese	n.a.	n.a.	PMID[20624681]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	PMID[23397723]
NPO5259	Garcinia buchananii	Species	Clusiaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[25625705]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288442]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7400820]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	Malaysian	n.a.	PMID[7506311]
NPO30556	Senecio abrotanifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30337	Calophyllum sp	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5449	Emilia coccinea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11656	Calophyllum sp.	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29168	Jacobaea abrotanifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5449	Emilia coccinea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20382	Ramalina paludosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30556	Senecio abrotanifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5449	Emilia coccinea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15264	Garcinia paucinervis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21601	Crocus sieberi	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22503	Salix matsudana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20897	Suberites domuncula	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21034	0cardia alba	Species	0cardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20382	Ramalina paludosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21852	Montanoa karwinskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20647	Eugenia myrcianthes	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20773	Jacobaea persoonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25528	Calophyllum brasiliense	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23186	Verbena bonariensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5449	Emilia coccinea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19901	Emilia sonchifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18516	Aplysilla spinifera	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5259	Garcinia buchananii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29168	Jacobaea abrotanifolia	Species	Asteraceae	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
EC50	1
IC50	2
Others	6

Activity Type	# Activity
Cell Line	3
Others	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	4800.0	nM	PMID[534567]
NPT886	Cell Line	NIH3T3	Mus musculus	CC50	=	10200.0	nM	PMID[534567]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	1000.0	nM	PMID[534567]
NPT35	Others	n.a.		EC50	=	26300.0	nM	PMID[534566]
NPT35	Others	n.a.		Activity	=	2.06	mmolequiv/mmol	PMID[534566]
NPT35	Others	n.a.		Activity	=	0.84	mmolequiv/mmol	PMID[534566]
NPT35	Others	n.a.		Activity	=	2.74	mmolequiv/mmol	PMID[534566]
NPT35	Others	n.a.		Activity	=	1.16	mmolequiv/mmol	PMID[534566]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	10.2	n.a.	PMID[534567]

☑ 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 NPC200246 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	445
0.1-0.2	2083
0.2-0.3	5195
0.3-0.4	11571
0.4-0.5	5633
0.5-0.6	4043
0.6-0.7	5099
0.7-0.8	4621
0.8-0.85	2133
0.85-0.9	1261
0.9-0.95	547
0.95-1	66

Similarity Score	Similarity Level	Natural Product ID
0.9932	High Similarity	NPC133970
0.9932	High Similarity	NPC5322
0.9932	High Similarity	NPC6633
0.9866	High Similarity	NPC218313
0.9866	High Similarity	NPC474681
0.98	High Similarity	NPC204879
0.9799	High Similarity	NPC470600
0.9735	High Similarity	NPC188433
0.9732	High Similarity	NPC256925
0.9732	High Similarity	NPC472280
0.9671	High Similarity	NPC57715
0.9671	High Similarity	NPC167678
0.9671	High Similarity	NPC234644
0.9671	High Similarity	NPC29876
0.9667	High Similarity	NPC472455
0.9664	High Similarity	NPC49402
0.9664	High Similarity	NPC227337
0.9664	High Similarity	NPC273462
0.9664	High Similarity	NPC70433
0.9664	High Similarity	NPC33051
0.9608	High Similarity	NPC83922
0.9608	High Similarity	NPC472448
0.9605	High Similarity	NPC204290
0.9605	High Similarity	NPC471973
0.9603	High Similarity	NPC52889
0.96	High Similarity	NPC117992
0.96	High Similarity	NPC152951
0.96	High Similarity	NPC57674
0.96	High Similarity	NPC234255
0.96	High Similarity	NPC230149
0.96	High Similarity	NPC168247
0.9597	High Similarity	NPC237994
0.9545	High Similarity	NPC303460
0.9545	High Similarity	NPC306321
0.9542	High Similarity	NPC259456
0.9539	High Similarity	NPC74178
0.9539	High Similarity	NPC184755
0.9536	High Similarity	NPC471985
0.9536	High Similarity	NPC115853
0.953	High Similarity	NPC154345
0.9524	High Similarity	NPC77378
0.9481	High Similarity	NPC474150
0.9481	High Similarity	NPC261470
0.9481	High Similarity	NPC474162
0.9477	High Similarity	NPC192686
0.9477	High Similarity	NPC118256
0.9477	High Similarity	NPC119209
0.9477	High Similarity	NPC476980
0.9474	High Similarity	NPC219867
0.9474	High Similarity	NPC161960
0.9474	High Similarity	NPC187745
0.9474	High Similarity	NPC304008
0.9474	High Similarity	NPC136674
0.9474	High Similarity	NPC180011
0.9463	High Similarity	NPC29231
0.9459	High Similarity	NPC43669
0.9459	High Similarity	NPC272721
0.9459	High Similarity	NPC196277
0.9419	High Similarity	NPC189473
0.9419	High Similarity	NPC23298
0.9416	High Similarity	NPC474038
0.9416	High Similarity	NPC134783
0.9408	High Similarity	NPC170026
0.9408	High Similarity	NPC68093
0.9408	High Similarity	NPC191146
0.9408	High Similarity	NPC282307
0.9408	High Similarity	NPC138243
0.9404	High Similarity	NPC170492
0.94	High Similarity	NPC31363
0.9392	High Similarity	NPC168803
0.9359	High Similarity	NPC275780
0.9359	High Similarity	NPC472450
0.9359	High Similarity	NPC50960
0.9359	High Similarity	NPC239752
0.9355	High Similarity	NPC329760
0.9355	High Similarity	NPC474034
0.9355	High Similarity	NPC474033
0.9351	High Similarity	NPC475784
0.9351	High Similarity	NPC139036
0.9351	High Similarity	NPC474960
0.9346	High Similarity	NPC27337
0.9346	High Similarity	NPC78225
0.9346	High Similarity	NPC284820
0.9346	High Similarity	NPC262286
0.9346	High Similarity	NPC291508
0.9346	High Similarity	NPC473272
0.9346	High Similarity	NPC476981
0.9346	High Similarity	NPC36852
0.9338	High Similarity	NPC60972
0.9338	High Similarity	NPC471982
0.9338	High Similarity	NPC477231
0.9338	High Similarity	NPC39732
0.9338	High Similarity	NPC39007
0.9338	High Similarity	NPC161277
0.9338	High Similarity	NPC257648
0.9333	High Similarity	NPC248102
0.9333	High Similarity	NPC88804
0.9333	High Similarity	NPC3825
0.9304	High Similarity	NPC288813
0.9299	High Similarity	NPC472449
0.9299	High Similarity	NPC39091
0.9299	High Similarity	NPC37870
0.9295	High Similarity	NPC472625
0.9295	High Similarity	NPC124038
0.9295	High Similarity	NPC186686
0.929	High Similarity	NPC26326
0.929	High Similarity	NPC472632
0.929	High Similarity	NPC258331
0.929	High Similarity	NPC471210
0.9286	High Similarity	NPC235448
0.9286	High Similarity	NPC55738
0.9281	High Similarity	NPC472907
0.9281	High Similarity	NPC35038
0.9281	High Similarity	NPC278778
0.9281	High Similarity	NPC474638
0.9281	High Similarity	NPC195796
0.9281	High Similarity	NPC276444
0.9281	High Similarity	NPC291878
0.9276	High Similarity	NPC292214
0.9276	High Similarity	NPC469550
0.9276	High Similarity	NPC88645
0.9276	High Similarity	NPC271779
0.9276	High Similarity	NPC206238
0.9276	High Similarity	NPC167091
0.9276	High Similarity	NPC472905
0.9272	High Similarity	NPC256406
0.9272	High Similarity	NPC251110
0.9272	High Similarity	NPC171010
0.9267	High Similarity	NPC264289
0.9267	High Similarity	NPC223579
0.9267	High Similarity	NPC333691
0.9267	High Similarity	NPC287101
0.9267	High Similarity	NPC142876
0.9267	High Similarity	NPC40290
0.9267	High Similarity	NPC52005
0.9267	High Similarity	NPC200060
0.9267	High Similarity	NPC264550
0.9267	High Similarity	NPC139293
0.9267	High Similarity	NPC69430
0.9267	High Similarity	NPC137062
0.9267	High Similarity	NPC195763
0.9267	High Similarity	NPC183950
0.9245	High Similarity	NPC472276
0.9236	High Similarity	NPC303174
0.9236	High Similarity	NPC108433
0.9236	High Similarity	NPC62261
0.9236	High Similarity	NPC300053
0.9231	High Similarity	NPC476247
0.9231	High Similarity	NPC25152
0.9231	High Similarity	NPC229632
0.9231	High Similarity	NPC78332
0.9226	High Similarity	NPC28241
0.9226	High Similarity	NPC174953
0.9226	High Similarity	NPC328102
0.9226	High Similarity	NPC472624
0.9221	High Similarity	NPC237418
0.9221	High Similarity	NPC471209
0.9221	High Similarity	NPC99597
0.9221	High Similarity	NPC476630
0.9221	High Similarity	NPC474055
0.9221	High Similarity	NPC67876
0.9221	High Similarity	NPC79053
0.9221	High Similarity	NPC472598
0.9221	High Similarity	NPC210084
0.9221	High Similarity	NPC218871
0.9221	High Similarity	NPC78071
0.9221	High Similarity	NPC472963
0.9221	High Similarity	NPC129684
0.9221	High Similarity	NPC299520
0.9216	High Similarity	NPC45849
0.9216	High Similarity	NPC20830
0.9216	High Similarity	NPC39184
0.9216	High Similarity	NPC470327
0.9216	High Similarity	NPC113906
0.9216	High Similarity	NPC200761
0.9216	High Similarity	NPC256612
0.9216	High Similarity	NPC477503
0.9216	High Similarity	NPC2928
0.9211	High Similarity	NPC301323
0.9211	High Similarity	NPC101996
0.9211	High Similarity	NPC25270
0.9211	High Similarity	NPC236637
0.9211	High Similarity	NPC71334
0.9211	High Similarity	NPC198826
0.9211	High Similarity	NPC156222
0.9211	High Similarity	NPC180234
0.9211	High Similarity	NPC166201
0.9211	High Similarity	NPC239128
0.9211	High Similarity	NPC131624
0.9211	High Similarity	NPC293183
0.9211	High Similarity	NPC120537
0.9211	High Similarity	NPC57030
0.9211	High Similarity	NPC256283
0.9211	High Similarity	NPC162313
0.9211	High Similarity	NPC55205
0.9211	High Similarity	NPC187498
0.9211	High Similarity	NPC188203
0.9211	High Similarity	NPC63187
0.9211	High Similarity	NPC472912
0.9211	High Similarity	NPC157784

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 NPC200246 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	426
0.1-0.2	1045
0.2-0.3	1852
0.3-0.4	2720
0.4-0.5	1663
0.5-0.6	977
0.6-0.7	311
0.7-0.8	99
0.8-0.85	39
0.85-0.9	12
0.9-0.95	6
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9211	High Similarity	NPD1934	Approved
0.915	High Similarity	NPD2801	Approved
0.915	High Similarity	NPD2393	Clinical (unspecified phase)
0.906	High Similarity	NPD1511	Approved
0.894	High Similarity	NPD1512	Approved
0.891	High Similarity	NPD3882	Suspended
0.8758	High Similarity	NPD6168	Clinical (unspecified phase)
0.8758	High Similarity	NPD6166	Phase 2
0.8758	High Similarity	NPD6167	Clinical (unspecified phase)
0.875	High Similarity	NPD7410	Clinical (unspecified phase)
0.871	High Similarity	NPD4380	Phase 2
0.865	High Similarity	NPD3818	Discontinued
0.8627	High Similarity	NPD4378	Clinical (unspecified phase)
0.8625	High Similarity	NPD5494	Approved
0.8598	High Similarity	NPD7054	Approved
0.8553	High Similarity	NPD4868	Clinical (unspecified phase)
0.8545	High Similarity	NPD7472	Approved
0.8545	High Similarity	NPD7074	Phase 3
0.8544	High Similarity	NPD1465	Phase 2
0.85	High Similarity	NPD7075	Discontinued
0.8491	Intermediate Similarity	NPD3817	Phase 2
0.8477	Intermediate Similarity	NPD1549	Phase 2
0.8428	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8411	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1510	Phase 2
0.8393	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8385	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8383	Intermediate Similarity	NPD6797	Phase 2
0.8378	Intermediate Similarity	NPD943	Approved
0.8365	Intermediate Similarity	NPD6801	Discontinued
0.8333	Intermediate Similarity	NPD7251	Discontinued
0.8313	Intermediate Similarity	NPD7819	Suspended
0.8302	Intermediate Similarity	NPD7411	Suspended
0.8293	Intermediate Similarity	NPD6232	Discontinued
0.8284	Intermediate Similarity	NPD7808	Phase 3
0.8261	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8255	Intermediate Similarity	NPD1240	Approved
0.8253	Intermediate Similarity	NPD7473	Discontinued
0.8224	Intermediate Similarity	NPD2796	Approved
0.816	Intermediate Similarity	NPD3749	Approved
0.8155	Intermediate Similarity	NPD5844	Phase 1
0.8155	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8146	Intermediate Similarity	NPD1607	Approved
0.8129	Intermediate Similarity	NPD3750	Approved
0.8121	Intermediate Similarity	NPD1247	Approved
0.8121	Intermediate Similarity	NPD6959	Discontinued
0.811	Intermediate Similarity	NPD919	Approved
0.8089	Intermediate Similarity	NPD6799	Approved
0.8065	Intermediate Similarity	NPD2800	Approved
0.8059	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD5402	Approved
0.7919	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD3926	Phase 2
0.7907	Intermediate Similarity	NPD6559	Discontinued
0.7901	Intermediate Similarity	NPD6599	Discontinued
0.7885	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7768	Phase 2
0.7843	Intermediate Similarity	NPD447	Suspended
0.7834	Intermediate Similarity	NPD1243	Approved
0.7826	Intermediate Similarity	NPD5403	Approved
0.7826	Intermediate Similarity	NPD920	Approved
0.7812	Intermediate Similarity	NPD5401	Approved
0.7806	Intermediate Similarity	NPD3748	Approved
0.7806	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD1613	Approved
0.7778	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD2313	Discontinued
0.7756	Intermediate Similarity	NPD2935	Discontinued
0.773	Intermediate Similarity	NPD3226	Approved
0.7727	Intermediate Similarity	NPD230	Phase 1
0.7722	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7716	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD2344	Approved
0.7707	Intermediate Similarity	NPD2346	Discontinued
0.7705	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD2799	Discontinued
0.7643	Intermediate Similarity	NPD6099	Approved
0.7643	Intermediate Similarity	NPD6100	Approved
0.7643	Intermediate Similarity	NPD1551	Phase 2
0.7613	Intermediate Similarity	NPD1933	Approved
0.7598	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD2534	Approved
0.7593	Intermediate Similarity	NPD2533	Approved
0.7593	Intermediate Similarity	NPD2532	Approved
0.7578	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7572	Intermediate Similarity	NPD3751	Discontinued
0.7566	Intermediate Similarity	NPD9494	Approved
0.7564	Intermediate Similarity	NPD6651	Approved
0.7562	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7562	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD5953	Discontinued
0.7529	Intermediate Similarity	NPD7286	Phase 2
0.7528	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2309	Approved
0.7514	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7468	Intermediate Similarity	NPD3027	Phase 3
0.7458	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD4628	Phase 3
0.7434	Intermediate Similarity	NPD1203	Approved
0.7423	Intermediate Similarity	NPD7390	Discontinued
0.7423	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD7685	Pre-registration
0.7384	Intermediate Similarity	NPD7199	Phase 2
0.7368	Intermediate Similarity	NPD6234	Discontinued
0.7358	Intermediate Similarity	NPD4308	Phase 3
0.7355	Intermediate Similarity	NPD4625	Phase 3
0.7351	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7349	Intermediate Similarity	NPD1653	Approved
0.7341	Intermediate Similarity	NPD3787	Discontinued
0.7318	Intermediate Similarity	NPD8312	Approved
0.7318	Intermediate Similarity	NPD8313	Approved
0.7301	Intermediate Similarity	NPD6190	Approved
0.7299	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD4908	Phase 1
0.7285	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7277	Intermediate Similarity	NPD7584	Approved
0.7273	Intermediate Similarity	NPD7228	Approved
0.7273	Intermediate Similarity	NPD2798	Approved
0.7243	Intermediate Similarity	NPD4360	Phase 2
0.7243	Intermediate Similarity	NPD4363	Phase 3
0.7237	Intermediate Similarity	NPD9717	Approved
0.7237	Intermediate Similarity	NPD9269	Phase 2
0.7234	Intermediate Similarity	NPD6782	Approved
0.7234	Intermediate Similarity	NPD6781	Approved
0.7234	Intermediate Similarity	NPD6780	Approved
0.7234	Intermediate Similarity	NPD6777	Approved
0.7234	Intermediate Similarity	NPD6776	Approved
0.7234	Intermediate Similarity	NPD6778	Approved
0.7234	Intermediate Similarity	NPD6779	Approved
0.7213	Intermediate Similarity	NPD4287	Approved
0.7208	Intermediate Similarity	NPD1470	Approved
0.7198	Intermediate Similarity	NPD8150	Discontinued
0.7197	Intermediate Similarity	NPD3268	Approved
0.7193	Intermediate Similarity	NPD4288	Approved
0.7176	Intermediate Similarity	NPD37	Approved
0.7171	Intermediate Similarity	NPD1610	Phase 2
0.7171	Intermediate Similarity	NPD422	Phase 1
0.717	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5124	Phase 1
0.7169	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD4965	Approved
0.7151	Intermediate Similarity	NPD4967	Phase 2
0.7151	Intermediate Similarity	NPD4966	Approved
0.7143	Intermediate Similarity	NPD5711	Approved
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD3225	Approved
0.7143	Intermediate Similarity	NPD5710	Approved
0.7133	Intermediate Similarity	NPD1548	Phase 1
0.7124	Intermediate Similarity	NPD1608	Approved
0.712	Intermediate Similarity	NPD7435	Discontinued
0.7113	Intermediate Similarity	NPD8151	Discontinued
0.7107	Intermediate Similarity	NPD4307	Phase 2
0.7104	Intermediate Similarity	NPD8434	Phase 2
0.7102	Intermediate Similarity	NPD5242	Approved
0.7101	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7458	Discontinued
0.7099	Intermediate Similarity	NPD5405	Approved
0.7099	Intermediate Similarity	NPD5404	Approved
0.7099	Intermediate Similarity	NPD5408	Approved
0.7099	Intermediate Similarity	NPD5406	Approved
0.7097	Intermediate Similarity	NPD2797	Approved
0.7091	Intermediate Similarity	NPD2354	Approved
0.7089	Intermediate Similarity	NPD411	Approved
0.7089	Intermediate Similarity	NPD3764	Approved
0.7078	Intermediate Similarity	NPD4749	Approved
0.7076	Intermediate Similarity	NPD6844	Discontinued
0.707	Intermediate Similarity	NPD6832	Phase 2
0.7066	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD2403	Approved
0.7059	Intermediate Similarity	NPD1201	Approved
0.7059	Intermediate Similarity	NPD6585	Discontinued
0.7055	Intermediate Similarity	NPD1471	Phase 3
0.7031	Intermediate Similarity	NPD7696	Phase 3
0.7031	Intermediate Similarity	NPD7698	Approved
0.7031	Intermediate Similarity	NPD7697	Approved
0.7024	Intermediate Similarity	NPD5049	Phase 3
0.7021	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4361	Phase 2
0.7018	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD2424	Discontinued
0.7006	Intermediate Similarity	NPD4357	Discontinued
0.7	Intermediate Similarity	NPD1729	Discontinued
0.6995	Remote Similarity	NPD7870	Phase 2
0.6995	Remote Similarity	NPD7871	Phase 2
0.6994	Remote Similarity	NPD5353	Approved
0.6994	Remote Similarity	NPD2296	Approved
0.6987	Remote Similarity	NPD3266	Approved
0.6987	Remote Similarity	NPD3267	Approved
0.6979	Remote Similarity	NPD6823	Phase 2
0.6978	Remote Similarity	NPD7549	Discontinued
0.6974	Remote Similarity	NPD9268	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data