NPASS Compound

Structure

CID6633 OpenBabel06191715332D 23 26 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 6.0622 -1.5000 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 -0.5000 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 5.1962 0.0000 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 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 5.1962 1.0000 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 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 5 1 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 7 2 0 0 0 0 6 9 1 0 0 0 0 7 18 1 0 0 0 0 8 12 2 0 0 0 0 8 13 1 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 10 16 1 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 12 23 1 0 0 0 0 13 14 2 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	310.08
Volume:	308.518
LogP:	4.319
LogD:	2.953
LogS:	-3.555
# Rotatable Bonds:	0
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.621
Synthetic Accessibility Score:	2.925
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.823
MDCK Permeability:	1.9688357497216202e-05
Pgp-inhibitor:	0.829
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.026
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.051

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024
Plasma Protein Binding (PPB):	96.99860382080078%
Volume Distribution (VD):	0.502
Pgp-substrate:	6.244688510894775%

ADMET: Metabolism

CYP1A2-inhibitor:	0.93
CYP1A2-substrate:	0.593
CYP2C19-inhibitor:	0.537
CYP2C19-substrate:	0.093
CYP2C9-inhibitor:	0.825
CYP2C9-substrate:	0.886
CYP2D6-inhibitor:	0.807
CYP2D6-substrate:	0.28
CYP3A4-inhibitor:	0.492
CYP3A4-substrate:	0.129

ADMET: Excretion

Clearance (CL):	1.676
Half-life (T1/2):	0.42

ADMET: Toxicity

hERG Blockers:	0.006
Human Hepatotoxicity (H-HT):	0.903
Drug-inuced Liver Injury (DILI):	0.978
AMES Toxicity:	0.552
Rat Oral Acute Toxicity:	0.787
Maximum Recommended Daily Dose:	0.805
Skin Sensitization:	0.752
Carcinogencity:	0.874
Eye Corrosion:	0.005
Eye Irritation:	0.602
Respiratory Toxicity:	0.76

Download Data

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

Natural Product: NPC6633

Natural Product ID:	NPC6633
*Common Name:**	6-Deoxyjacareubin
IUPAC Name:	5,10-dihydroxy-2,2-dimethylpyrano[3,2-b]xanthen-6-one
Synonyms:	6-Deoxyjacareubin
Standard InCHIKey:	NHNIESSJWQBRJW-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H14O5/c1-18(2)7-6-9-12(23-18)8-13-14(15(9)20)16(21)10-4-3-5-11(19)17(10)22-13/h3-8,19-20H,1-2H3
SMILES:	Oc1c2C=CC(Oc2cc2c1c(=O)c1c(o2)c(O)ccc1)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL457949
PubChem CID:	5281629
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
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[11170668]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	roots	n.a.	n.a.	PMID[12932139]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[14695790]
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]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[16124764]
NPO22503	Salix matsudana	Species	Salicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18794770]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	Zhang County, Gansu Province, China	2002-Sep	PMID[19702283]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	stem	n.a.	PMID[20188156]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	Chinese	n.a.	n.a.	PMID[20624681]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[21534583]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23691978]
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]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29752	Cudrania cochinchinensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20382	Ramalina paludosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2804	Calophyllum inophyllum	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]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20458	Strychnos decussata	Species	Loganiaceae	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]
NPO23186	Verbena bonariensis	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18516	Aplysilla spinifera	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16861	Garcinia nigrolineata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25806	Streptomyces violaceus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21601	Crocus sieberi	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21034	0cardia alba	Species	0cardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26101	Andropogon zizanioides	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21852	Montanoa karwinskii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26671	Hapalosiphon welwitschii	Species	Hapalosiphonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO23156	Maclura cochinchinensis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27363	Gynochthodes officinalis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20458	Strychnos decussata	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20773	Jacobaea persoonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20091	Iotrochota baculifera	Species	Iotrochotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20897	Suberites domuncula	Species	Suberitidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22503	Salix matsudana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20382	Ramalina paludosa	Species	Ramalinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20647	Eugenia myrcianthes	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28994	Acacia horrida	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24502	Rosa roxburghii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19038	Zanha golungensis	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25837	Euphorbia micractina	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2804	Calophyllum inophyllum	Species	Calophyllaceae	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	9
Others	5

Activity Type	# Activity
Cell Line	5
Organism	9
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT924	Cell Line	HSC-2	Homo sapiens	CC50	=	480000.0	nM	PMID[508914]
NPT924	Cell Line	HSC-2	Homo sapiens	Ratio	>	1.4	n.a.	PMID[508914]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	=	26000.0	nM	PMID[508918]
NPT886	Cell Line	NIH3T3	Mus musculus	CC50	=	25300.0	nM	PMID[508918]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2700.0	nM	PMID[508918]
NPT27	Others	Unspecified		CC50	>	650000.0	nM	PMID[508914]
NPT20	Organism	Candida albicans	Candida albicans	MIC	>	128.0	ug.mL-1	PMID[508915]
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	>	128.0	ug.mL-1	PMID[508915]
NPT554	Organism	Candida glabrata	Candida glabrata	MIC	>	128.0	ug.mL-1	PMID[508915]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	>	128.0	ug.mL-1	PMID[508915]
NPT87	Organism	Aspergillus fumigatus	Aspergillus fumigatus	MIC	>	128.0	ug.mL-1	PMID[508915]
NPT925	Organism	Emericella nidulans	Emericella nidulans	MIC	>	128.0	ug.mL-1	PMID[508915]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	32.0	ug.mL-1	PMID[508915]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	4600.0	nM	PMID[508916]
NPT2	Others	Unspecified		Ratio CC50/IC50	=	9.4	n.a.	PMID[508918]

☑ 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 NPC6633 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	446
0.1-0.2	2015
0.2-0.3	4942
0.3-0.4	11386
0.4-0.5	5983
0.5-0.6	3901
0.6-0.7	5148
0.7-0.8	4620
0.8-0.85	2212
0.85-0.9	1344
0.9-0.95	603
0.95-1	97

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133970
1.0	High Similarity	NPC5322
0.9933	High Similarity	NPC474681
0.9933	High Similarity	NPC218313
0.9932	High Similarity	NPC200246
0.9867	High Similarity	NPC204879
0.9799	High Similarity	NPC472280
0.9737	High Similarity	NPC29876
0.9737	High Similarity	NPC167678
0.9737	High Similarity	NPC234644
0.9733	High Similarity	NPC470600
0.9733	High Similarity	NPC472455
0.9732	High Similarity	NPC273462
0.9732	High Similarity	NPC49402
0.9732	High Similarity	NPC33051
0.9732	High Similarity	NPC227337
0.9732	High Similarity	NPC70433
0.9673	High Similarity	NPC472448
0.9673	High Similarity	NPC83922
0.9671	High Similarity	NPC204290
0.9671	High Similarity	NPC188433
0.9671	High Similarity	NPC471973
0.9669	High Similarity	NPC52889
0.9667	High Similarity	NPC152951
0.9667	High Similarity	NPC234255
0.9667	High Similarity	NPC230149
0.9667	High Similarity	NPC57674
0.9667	High Similarity	NPC168247
0.9667	High Similarity	NPC117992
0.9667	High Similarity	NPC256925
0.9664	High Similarity	NPC237994
0.9608	High Similarity	NPC259456
0.9608	High Similarity	NPC57715
0.9605	High Similarity	NPC184755
0.9605	High Similarity	NPC74178
0.9603	High Similarity	NPC471985
0.9597	High Similarity	NPC154345
0.9545	High Similarity	NPC474150
0.9545	High Similarity	NPC474162
0.9542	High Similarity	NPC119209
0.9542	High Similarity	NPC118256
0.9542	High Similarity	NPC476980
0.9542	High Similarity	NPC192686
0.9539	High Similarity	NPC136674
0.9539	High Similarity	NPC161960
0.9539	High Similarity	NPC304008
0.9539	High Similarity	NPC187745
0.953	High Similarity	NPC29231
0.9527	High Similarity	NPC43669
0.9527	High Similarity	NPC196277
0.9527	High Similarity	NPC272721
0.9484	High Similarity	NPC189473
0.9484	High Similarity	NPC303460
0.9484	High Similarity	NPC306321
0.9484	High Similarity	NPC23298
0.9481	High Similarity	NPC134783
0.9481	High Similarity	NPC474038
0.9474	High Similarity	NPC282307
0.9474	High Similarity	NPC138243
0.9474	High Similarity	NPC191146
0.9474	High Similarity	NPC170026
0.9474	High Similarity	NPC115853
0.9474	High Similarity	NPC68093
0.947	High Similarity	NPC170492
0.9467	High Similarity	NPC31363
0.9459	High Similarity	NPC168803
0.9459	High Similarity	NPC77378
0.9423	High Similarity	NPC239752
0.9423	High Similarity	NPC472450
0.9423	High Similarity	NPC275780
0.9419	High Similarity	NPC329760
0.9419	High Similarity	NPC261470
0.9419	High Similarity	NPC474033
0.9419	High Similarity	NPC474034
0.9416	High Similarity	NPC474960
0.9416	High Similarity	NPC475784
0.9416	High Similarity	NPC139036
0.9412	High Similarity	NPC78225
0.9412	High Similarity	NPC219867
0.9412	High Similarity	NPC262286
0.9412	High Similarity	NPC473272
0.9412	High Similarity	NPC291508
0.9412	High Similarity	NPC27337
0.9412	High Similarity	NPC476981
0.9412	High Similarity	NPC284820
0.9412	High Similarity	NPC180011
0.9412	High Similarity	NPC36852
0.9404	High Similarity	NPC60972
0.9404	High Similarity	NPC257648
0.9404	High Similarity	NPC39732
0.9404	High Similarity	NPC477231
0.9404	High Similarity	NPC471982
0.94	High Similarity	NPC3825
0.94	High Similarity	NPC88804
0.9367	High Similarity	NPC288813
0.9363	High Similarity	NPC37870
0.9363	High Similarity	NPC472449
0.9363	High Similarity	NPC39091
0.9359	High Similarity	NPC186686
0.9359	High Similarity	NPC124038
0.9359	High Similarity	NPC472625
0.9355	High Similarity	NPC472632
0.9355	High Similarity	NPC258331
0.9355	High Similarity	NPC471210
0.9355	High Similarity	NPC26326
0.9351	High Similarity	NPC55738
0.9351	High Similarity	NPC235448
0.9346	High Similarity	NPC195796
0.9346	High Similarity	NPC35038
0.9346	High Similarity	NPC472907
0.9346	High Similarity	NPC276444
0.9346	High Similarity	NPC474638
0.9346	High Similarity	NPC291878
0.9346	High Similarity	NPC278778
0.9342	High Similarity	NPC206238
0.9342	High Similarity	NPC292214
0.9342	High Similarity	NPC271779
0.9342	High Similarity	NPC167091
0.9342	High Similarity	NPC472905
0.9342	High Similarity	NPC469550
0.9342	High Similarity	NPC88645
0.9338	High Similarity	NPC251110
0.9338	High Similarity	NPC256406
0.9333	High Similarity	NPC137062
0.9333	High Similarity	NPC183950
0.9333	High Similarity	NPC69430
0.9333	High Similarity	NPC195763
0.9333	High Similarity	NPC264550
0.9333	High Similarity	NPC333691
0.9333	High Similarity	NPC287101
0.9333	High Similarity	NPC142876
0.9333	High Similarity	NPC200060
0.9333	High Similarity	NPC223579
0.9333	High Similarity	NPC40290
0.9333	High Similarity	NPC52005
0.9333	High Similarity	NPC264289
0.9333	High Similarity	NPC139293
0.9299	High Similarity	NPC303174
0.9299	High Similarity	NPC62261
0.9299	High Similarity	NPC300053
0.9299	High Similarity	NPC108433
0.9299	High Similarity	NPC50960
0.9295	High Similarity	NPC78332
0.9295	High Similarity	NPC476247
0.9295	High Similarity	NPC25152
0.9295	High Similarity	NPC229632
0.929	High Similarity	NPC28241
0.929	High Similarity	NPC472624
0.929	High Similarity	NPC174953
0.929	High Similarity	NPC328102
0.9286	High Similarity	NPC129684
0.9286	High Similarity	NPC237418
0.9286	High Similarity	NPC476630
0.9286	High Similarity	NPC472598
0.9286	High Similarity	NPC210084
0.9286	High Similarity	NPC99597
0.9286	High Similarity	NPC218871
0.9286	High Similarity	NPC299520
0.9286	High Similarity	NPC472963
0.9286	High Similarity	NPC471209
0.9286	High Similarity	NPC474055
0.9286	High Similarity	NPC78071
0.9286	High Similarity	NPC67876
0.9281	High Similarity	NPC39184
0.9281	High Similarity	NPC477503
0.9281	High Similarity	NPC256612
0.9281	High Similarity	NPC113906
0.9281	High Similarity	NPC2928
0.9281	High Similarity	NPC45849
0.9281	High Similarity	NPC200761
0.9281	High Similarity	NPC470327
0.9281	High Similarity	NPC20830
0.9276	High Similarity	NPC71334
0.9276	High Similarity	NPC100887
0.9276	High Similarity	NPC37684
0.9276	High Similarity	NPC275836
0.9276	High Similarity	NPC301323
0.9276	High Similarity	NPC25270
0.9276	High Similarity	NPC83508
0.9276	High Similarity	NPC236637
0.9276	High Similarity	NPC239128
0.9276	High Similarity	NPC156222
0.9276	High Similarity	NPC131624
0.9276	High Similarity	NPC180234
0.9276	High Similarity	NPC57030
0.9276	High Similarity	NPC55205
0.9276	High Similarity	NPC120537
0.9276	High Similarity	NPC188203
0.9276	High Similarity	NPC293183
0.9276	High Similarity	NPC256283
0.9276	High Similarity	NPC162313
0.9276	High Similarity	NPC39007
0.9276	High Similarity	NPC472912
0.9276	High Similarity	NPC161277
0.9276	High Similarity	NPC63187
0.9276	High Similarity	NPC187498
0.9276	High Similarity	NPC275722
0.9276	High Similarity	NPC241498
0.9276	High Similarity	NPC157784
0.9276	High Similarity	NPC302950

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 NPC6633 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	428
0.1-0.2	1023
0.2-0.3	1772
0.3-0.4	2708
0.4-0.5	1726
0.5-0.6	980
0.6-0.7	351
0.7-0.8	103
0.8-0.85	40
0.85-0.9	12
0.9-0.95	7
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9276	High Similarity	NPD1934	Approved
0.9216	High Similarity	NPD2801	Approved
0.9216	High Similarity	NPD2393	Clinical (unspecified phase)
0.9128	High Similarity	NPD1511	Approved
0.9007	High Similarity	NPD1512	Approved
0.8974	High Similarity	NPD3882	Suspended
0.882	High Similarity	NPD6168	Clinical (unspecified phase)
0.882	High Similarity	NPD6167	Clinical (unspecified phase)
0.882	High Similarity	NPD6166	Phase 2
0.8816	High Similarity	NPD7410	Clinical (unspecified phase)
0.8774	High Similarity	NPD4380	Phase 2
0.8712	High Similarity	NPD3818	Discontinued
0.8693	High Similarity	NPD4378	Clinical (unspecified phase)
0.8688	High Similarity	NPD5494	Approved
0.8659	High Similarity	NPD7054	Approved
0.8616	High Similarity	NPD4868	Clinical (unspecified phase)
0.8606	High Similarity	NPD7074	Phase 3
0.8606	High Similarity	NPD7472	Approved
0.8562	High Similarity	NPD7075	Discontinued
0.8553	High Similarity	NPD3817	Phase 2
0.8543	High Similarity	NPD1549	Phase 2
0.8491	Intermediate Similarity	NPD1465	Phase 2
0.8491	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8477	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8467	Intermediate Similarity	NPD1510	Phase 2
0.8452	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8447	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD943	Approved
0.8443	Intermediate Similarity	NPD6797	Phase 2
0.8393	Intermediate Similarity	NPD7251	Discontinued
0.8375	Intermediate Similarity	NPD7819	Suspended
0.8365	Intermediate Similarity	NPD7411	Suspended
0.8354	Intermediate Similarity	NPD6232	Discontinued
0.8343	Intermediate Similarity	NPD7808	Phase 3
0.8323	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8322	Intermediate Similarity	NPD1240	Approved
0.8313	Intermediate Similarity	NPD7473	Discontinued
0.8313	Intermediate Similarity	NPD6801	Discontinued
0.8289	Intermediate Similarity	NPD2796	Approved
0.8221	Intermediate Similarity	NPD3749	Approved
0.8214	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD5844	Phase 1
0.8212	Intermediate Similarity	NPD1607	Approved
0.8194	Intermediate Similarity	NPD3750	Approved
0.8182	Intermediate Similarity	NPD1247	Approved
0.8171	Intermediate Similarity	NPD919	Approved
0.8153	Intermediate Similarity	NPD6799	Approved
0.8118	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8072	Intermediate Similarity	NPD6959	Discontinued
0.8054	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD2800	Approved
0.7988	Intermediate Similarity	NPD5402	Approved
0.7987	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD3926	Phase 2
0.7965	Intermediate Similarity	NPD6559	Discontinued
0.7963	Intermediate Similarity	NPD6599	Discontinued
0.7949	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD7768	Phase 2
0.7908	Intermediate Similarity	NPD447	Suspended
0.7898	Intermediate Similarity	NPD1243	Approved
0.7888	Intermediate Similarity	NPD5403	Approved
0.7875	Intermediate Similarity	NPD5401	Approved
0.7871	Intermediate Similarity	NPD3748	Approved
0.7871	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD1613	Approved
0.7829	Intermediate Similarity	NPD2313	Discontinued
0.7821	Intermediate Similarity	NPD2935	Discontinued
0.7792	Intermediate Similarity	NPD230	Phase 1
0.7791	Intermediate Similarity	NPD3226	Approved
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD920	Approved
0.7771	Intermediate Similarity	NPD2346	Discontinued
0.7771	Intermediate Similarity	NPD2344	Approved
0.776	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7756	Intermediate Similarity	NPD2799	Discontinued
0.7756	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD1551	Phase 2
0.7707	Intermediate Similarity	NPD6100	Approved
0.7707	Intermediate Similarity	NPD6099	Approved
0.7677	Intermediate Similarity	NPD1933	Approved
0.7654	Intermediate Similarity	NPD2534	Approved
0.7654	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD2532	Approved
0.7654	Intermediate Similarity	NPD2533	Approved
0.764	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD9494	Approved
0.763	Intermediate Similarity	NPD3751	Discontinued
0.7625	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD5953	Discontinued
0.7584	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD2309	Approved
0.7569	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3027	Phase 3
0.7516	Intermediate Similarity	NPD6651	Approved
0.7516	Intermediate Similarity	NPD4628	Phase 3
0.7514	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1203	Approved
0.7486	Intermediate Similarity	NPD7286	Phase 2
0.7485	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7390	Discontinued
0.7484	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7458	Intermediate Similarity	NPD7685	Pre-registration
0.7442	Intermediate Similarity	NPD7199	Phase 2
0.7427	Intermediate Similarity	NPD6234	Discontinued
0.7421	Intermediate Similarity	NPD4308	Phase 3
0.7419	Intermediate Similarity	NPD4625	Phase 3
0.741	Intermediate Similarity	NPD1653	Approved
0.7405	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7399	Intermediate Similarity	NPD3787	Discontinued
0.7374	Intermediate Similarity	NPD8312	Approved
0.7374	Intermediate Similarity	NPD8313	Approved
0.7362	Intermediate Similarity	NPD6190	Approved
0.7356	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD4908	Phase 1
0.7351	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7338	Intermediate Similarity	NPD2798	Approved
0.733	Intermediate Similarity	NPD7228	Approved
0.733	Intermediate Similarity	NPD7584	Approved
0.7303	Intermediate Similarity	NPD9717	Approved
0.7303	Intermediate Similarity	NPD9269	Phase 2
0.7297	Intermediate Similarity	NPD4363	Phase 3
0.7297	Intermediate Similarity	NPD4360	Phase 2
0.7287	Intermediate Similarity	NPD6780	Approved
0.7287	Intermediate Similarity	NPD6779	Approved
0.7287	Intermediate Similarity	NPD6778	Approved
0.7287	Intermediate Similarity	NPD6776	Approved
0.7287	Intermediate Similarity	NPD6777	Approved
0.7287	Intermediate Similarity	NPD6782	Approved
0.7287	Intermediate Similarity	NPD6781	Approved
0.7273	Intermediate Similarity	NPD1470	Approved
0.7268	Intermediate Similarity	NPD4287	Approved
0.7261	Intermediate Similarity	NPD3268	Approved
0.7253	Intermediate Similarity	NPD8150	Discontinued
0.7251	Intermediate Similarity	NPD4288	Approved
0.7237	Intermediate Similarity	NPD1610	Phase 2
0.7237	Intermediate Similarity	NPD422	Phase 1
0.7235	Intermediate Similarity	NPD37	Approved
0.7233	Intermediate Similarity	NPD5124	Phase 1
0.7233	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4967	Phase 2
0.7209	Intermediate Similarity	NPD4966	Approved
0.7209	Intermediate Similarity	NPD4965	Approved
0.7208	Intermediate Similarity	NPD3225	Approved
0.7205	Intermediate Similarity	NPD7033	Discontinued
0.72	Intermediate Similarity	NPD1548	Phase 1
0.72	Intermediate Similarity	NPD5710	Approved
0.72	Intermediate Similarity	NPD5711	Approved
0.719	Intermediate Similarity	NPD1608	Approved
0.7173	Intermediate Similarity	NPD7435	Discontinued
0.717	Intermediate Similarity	NPD4307	Phase 2
0.7165	Intermediate Similarity	NPD8151	Discontinued
0.7161	Intermediate Similarity	NPD2797	Approved
0.716	Intermediate Similarity	NPD7458	Discontinued
0.716	Intermediate Similarity	NPD5405	Approved
0.716	Intermediate Similarity	NPD5406	Approved
0.716	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD5404	Approved
0.716	Intermediate Similarity	NPD5408	Approved
0.7159	Intermediate Similarity	NPD5242	Approved
0.7158	Intermediate Similarity	NPD8434	Phase 2
0.7152	Intermediate Similarity	NPD2354	Approved
0.7152	Intermediate Similarity	NPD3764	Approved
0.7152	Intermediate Similarity	NPD411	Approved
0.7143	Intermediate Similarity	NPD4749	Approved
0.7135	Intermediate Similarity	NPD6844	Discontinued
0.7134	Intermediate Similarity	NPD6832	Phase 2
0.7126	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7124	Intermediate Similarity	NPD1201	Approved
0.7118	Intermediate Similarity	NPD6585	Discontinued
0.7117	Intermediate Similarity	NPD1471	Phase 3
0.7083	Intermediate Similarity	NPD7697	Approved
0.7083	Intermediate Similarity	NPD7696	Phase 3
0.7083	Intermediate Similarity	NPD7698	Approved
0.7083	Intermediate Similarity	NPD5049	Phase 3
0.7076	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7074	Intermediate Similarity	NPD4361	Phase 2
0.7074	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD2424	Discontinued
0.7066	Intermediate Similarity	NPD4357	Discontinued
0.7052	Intermediate Similarity	NPD5353	Approved
0.7052	Intermediate Similarity	NPD2296	Approved
0.7051	Intermediate Similarity	NPD3267	Approved
0.7051	Intermediate Similarity	NPD3266	Approved
0.7047	Intermediate Similarity	NPD7871	Phase 2
0.7047	Intermediate Similarity	NPD7870	Phase 2
0.7039	Intermediate Similarity	NPD9268	Approved
0.7033	Intermediate Similarity	NPD7549	Discontinued
0.7031	Intermediate Similarity	NPD6823	Phase 2
0.7026	Intermediate Similarity	NPD7701	Phase 2
0.7022	Intermediate Similarity	NPD2403	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