NPASS Compound

Structure

CID214919 OpenBabel06191716002D 25 27 0 0 0 0 0 0 0 0999 V2000 3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 4.3301 3.5000 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 2.5981 0.5000 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 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 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 -0.8660 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 0.8660 0.5000 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 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 22 1 0 0 0 0 3 23 1 0 0 0 0 4 24 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 12 1 0 0 0 0 7 13 2 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 15 1 0 0 0 0 10 11 1 0 0 0 0 10 16 2 0 0 0 0 11 17 1 0 0 0 0 11 20 2 0 0 0 0 12 18 2 0 0 0 0 12 21 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 0 0 0 0 14 17 2 0 0 0 0 14 25 1 0 0 0 0 15 19 2 0 0 0 0 15 23 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 19 1 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	342.11
Volume:	343.16
LogP:	2.607
LogD:	2.591
LogS:	-4.088
# Rotatable Bonds:	5
TPSA:	67.13
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	2.264
Fsp3:	0.211
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.623
MDCK Permeability:	4.319411891628988e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.021

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.304
Plasma Protein Binding (PPB):	73.30571746826172%
Volume Distribution (VD):	0.79
Pgp-substrate:	16.60853385925293%

ADMET: Metabolism

CYP1A2-inhibitor:	0.871
CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.881
CYP2C19-substrate:	0.871
CYP2C9-inhibitor:	0.796
CYP2C9-substrate:	0.927
CYP2D6-inhibitor:	0.069
CYP2D6-substrate:	0.945
CYP3A4-inhibitor:	0.833
CYP3A4-substrate:	0.747

ADMET: Excretion

Clearance (CL):	4.632
Half-life (T1/2):	0.253

ADMET: Toxicity

hERG Blockers:	0.197
Human Hepatotoxicity (H-HT):	0.099
Drug-inuced Liver Injury (DILI):	0.898
AMES Toxicity:	0.551
Rat Oral Acute Toxicity:	0.186
Maximum Recommended Daily Dose:	0.026
Skin Sensitization:	0.056
Carcinogencity:	0.136
Eye Corrosion:	0.003
Eye Irritation:	0.209
Respiratory Toxicity:	0.324

Download Data

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

Natural Product: NPC214919

Natural Product ID:	NPC214919
*Common Name:**	Zapotin
IUPAC Name:	2-(2,6-dimethoxyphenyl)-5,6-dimethoxychromen-4-one
Synonyms:	5,6,2',6'-Tetramethoxyflavone
Standard InCHIKey:	PBQMALAAFQMDSP-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C19H18O6/c1-21-12-6-5-7-13(22-2)18(12)16-10-11(20)17-14(25-16)8-9-15(23-3)19(17)24-4/h5-10H,1-4H3
SMILES:	COc1cccc(c1c1cc(=O)c2c(o1)ccc(c2OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL375582
PubChem CID:	629965
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002591] 6-O-methylated flavonoids

*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
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	seed	n.a.	PMID[10075120]
NPO7344	Spiraea prunifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473429]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499335]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17228877]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[18484537]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[19615910]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29323912]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	root	n.a.	PMID[731398]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[731398]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7714541]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7760071]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[7798964]
NPO19895	Plectranthus hereroensis	Species	Lamiaceae	Eukaryota	Roots	n.a.	n.a.	PMID[7931371]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7964801]
NPO23356	Ascodesmis sphaerospora	Species	Ascodesmidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9868168]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7344	Spiraea prunifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23588	Ursinia anthemoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17492	Amomum reticulatum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23356	Ascodesmis sphaerospora	Species	Ascodesmidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19895	Plectranthus hereroensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24396	Grosvenoria rimbachii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO15572	Espeletiopsis purpurascens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23398	Caralluma russeliana	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23911	Alpinia officinarum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24280	Helianthus californicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24038	Casimiroa edulis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23822	Polypodium aureum	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23628	Imperata cylindrica	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23490	Dalbergia monetaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9814	Lactarius fuliginosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
IC50	2
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2680	Individual Protein	Ornithine decarboxylase	Homo sapiens	IC50	=	3400.0	nM	PMID[570862]
NPT116	Cell Line	HL-60	Homo sapiens	ED50	=	0.5	uM	PMID[570862]
NPT116	Cell Line	HL-60	Homo sapiens	Activity	=	61.0	%	PMID[570862]
NPT2	Others	Unspecified		IC50	=	7600.0	nM	PMID[570862]

☑ 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 NPC214919 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	496
0.1-0.2	1988
0.2-0.3	5267
0.3-0.4	11872
0.4-0.5	5444
0.5-0.6	4144
0.6-0.7	5731
0.7-0.8	4950
0.8-0.85	1693
0.85-0.9	802
0.9-0.95	279
0.95-1	31

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC124467
0.9854	High Similarity	NPC23955
0.9712	High Similarity	NPC110639
0.9712	High Similarity	NPC215932
0.9712	High Similarity	NPC14958
0.9712	High Similarity	NPC106461
0.9712	High Similarity	NPC40818
0.9643	High Similarity	NPC85233
0.9643	High Similarity	NPC205522
0.9571	High Similarity	NPC302408
0.9571	High Similarity	NPC283002
0.9507	High Similarity	NPC69752
0.95	High Similarity	NPC136278
0.95	High Similarity	NPC165512
0.9496	High Similarity	NPC70853
0.9496	High Similarity	NPC9966
0.9441	High Similarity	NPC259058
0.9441	High Similarity	NPC201547
0.9437	High Similarity	NPC10304
0.9437	High Similarity	NPC63256
0.9429	High Similarity	NPC113089
0.9424	High Similarity	NPC29536
0.9375	High Similarity	NPC208043
0.9375	High Similarity	NPC226973
0.9371	High Similarity	NPC238366
0.9371	High Similarity	NPC181250
0.931	High Similarity	NPC134677
0.9306	High Similarity	NPC306821
0.9296	High Similarity	NPC231013
0.9296	High Similarity	NPC120924
0.9296	High Similarity	NPC310259
0.9296	High Similarity	NPC195919
0.9296	High Similarity	NPC216314
0.9247	High Similarity	NPC183878
0.9247	High Similarity	NPC86485
0.9247	High Similarity	NPC255350
0.9247	High Similarity	NPC160951
0.9247	High Similarity	NPC176775
0.9247	High Similarity	NPC186507
0.9247	High Similarity	NPC47781
0.9247	High Similarity	NPC22519
0.9247	High Similarity	NPC145379
0.9247	High Similarity	NPC472408
0.9247	High Similarity	NPC231018
0.9247	High Similarity	NPC274327
0.9247	High Similarity	NPC69394
0.9241	High Similarity	NPC308451
0.9236	High Similarity	NPC328119
0.9231	High Similarity	NPC299923
0.9231	High Similarity	NPC46941
0.9225	High Similarity	NPC471590
0.9214	High Similarity	NPC58229
0.9184	High Similarity	NPC146165
0.9184	High Similarity	NPC196439
0.9184	High Similarity	NPC128863
0.9184	High Similarity	NPC50715
0.9184	High Similarity	NPC227325
0.9184	High Similarity	NPC163780
0.9184	High Similarity	NPC2476
0.9184	High Similarity	NPC201136
0.9184	High Similarity	NPC92659
0.9184	High Similarity	NPC256612
0.9184	High Similarity	NPC122623
0.9184	High Similarity	NPC167815
0.9184	High Similarity	NPC276059
0.9184	High Similarity	NPC189960
0.9184	High Similarity	NPC138360
0.9184	High Similarity	NPC241774
0.9184	High Similarity	NPC213622
0.9184	High Similarity	NPC280339
0.9184	High Similarity	NPC32557
0.9184	High Similarity	NPC4455
0.9184	High Similarity	NPC34725
0.9184	High Similarity	NPC20830
0.9184	High Similarity	NPC183597
0.9178	High Similarity	NPC222830
0.9178	High Similarity	NPC120163
0.9178	High Similarity	NPC239128
0.9178	High Similarity	NPC293183
0.9178	High Similarity	NPC162313
0.9178	High Similarity	NPC188203
0.9178	High Similarity	NPC156222
0.9178	High Similarity	NPC301123
0.9178	High Similarity	NPC241498
0.9178	High Similarity	NPC275836
0.9178	High Similarity	NPC166201
0.9178	High Similarity	NPC301323
0.9178	High Similarity	NPC83508
0.9178	High Similarity	NPC100887
0.9178	High Similarity	NPC187498
0.9178	High Similarity	NPC212678
0.9178	High Similarity	NPC275722
0.9178	High Similarity	NPC57030
0.9178	High Similarity	NPC131624
0.9178	High Similarity	NPC25270
0.9178	High Similarity	NPC292460
0.9178	High Similarity	NPC256283
0.9178	High Similarity	NPC198826
0.9178	High Similarity	NPC71334
0.9167	High Similarity	NPC261548
0.9167	High Similarity	NPC195202
0.9155	High Similarity	NPC293201
0.9155	High Similarity	NPC182842
0.913	High Similarity	NPC77955
0.9122	High Similarity	NPC257277
0.9122	High Similarity	NPC49824
0.9122	High Similarity	NPC178854
0.9116	High Similarity	NPC276409
0.9116	High Similarity	NPC250822
0.9116	High Similarity	NPC476289
0.9116	High Similarity	NPC75279
0.9116	High Similarity	NPC280937
0.9116	High Similarity	NPC472915
0.9116	High Similarity	NPC128961
0.911	High Similarity	NPC117579
0.9103	High Similarity	NPC294502
0.9103	High Similarity	NPC200221
0.9097	High Similarity	NPC33265
0.9097	High Similarity	NPC62536
0.9097	High Similarity	NPC12200
0.906	High Similarity	NPC476981
0.906	High Similarity	NPC19097
0.906	High Similarity	NPC470402
0.906	High Similarity	NPC227192
0.906	High Similarity	NPC110070
0.906	High Similarity	NPC189179
0.906	High Similarity	NPC75215
0.906	High Similarity	NPC224137
0.906	High Similarity	NPC203891
0.906	High Similarity	NPC93376
0.906	High Similarity	NPC101830
0.9054	High Similarity	NPC37392
0.9054	High Similarity	NPC26227
0.9054	High Similarity	NPC44079
0.9054	High Similarity	NPC201451
0.9054	High Similarity	NPC208197
0.9054	High Similarity	NPC472909
0.9048	High Similarity	NPC39732
0.9048	High Similarity	NPC75069
0.9048	High Similarity	NPC142540
0.9048	High Similarity	NPC60972
0.9041	High Similarity	NPC166753
0.9041	High Similarity	NPC184136
0.9041	High Similarity	NPC50728
0.9034	High Similarity	NPC476342
0.9014	High Similarity	NPC185607
0.9	High Similarity	NPC238405
0.9	High Similarity	NPC288669
0.9	High Similarity	NPC191459
0.9	High Similarity	NPC115798
0.9	High Similarity	NPC204854
0.9	High Similarity	NPC130894
0.9	High Similarity	NPC143828
0.9	High Similarity	NPC4481
0.9	High Similarity	NPC261004
0.9	High Similarity	NPC18772
0.9	High Similarity	NPC18607
0.9	High Similarity	NPC300943
0.9	High Similarity	NPC152166
0.9	High Similarity	NPC9609
0.9	High Similarity	NPC104459
0.9	High Similarity	NPC176300
0.9	High Similarity	NPC22472
0.9	High Similarity	NPC257914
0.9	High Similarity	NPC7846
0.9	High Similarity	NPC25495
0.9	High Similarity	NPC105242
0.9	High Similarity	NPC44573
0.9	High Similarity	NPC253634
0.9	High Similarity	NPC19687
0.8993	High Similarity	NPC98661
0.8993	High Similarity	NPC43243
0.8993	High Similarity	NPC180340
0.8993	High Similarity	NPC247017
0.8993	High Similarity	NPC472916
0.8993	High Similarity	NPC245546
0.8993	High Similarity	NPC303255
0.8993	High Similarity	NPC474520
0.8993	High Similarity	NPC292107
0.8993	High Similarity	NPC266960
0.8986	High Similarity	NPC246204
0.898	High Similarity	NPC236769
0.898	High Similarity	NPC474170
0.898	High Similarity	NPC474663
0.898	High Similarity	NPC262623
0.898	High Similarity	NPC474388
0.898	High Similarity	NPC198615
0.898	High Similarity	NPC472535
0.898	High Similarity	NPC149614
0.8973	High Similarity	NPC177298
0.8973	High Similarity	NPC52005
0.8973	High Similarity	NPC137062
0.8973	High Similarity	NPC159103
0.8973	High Similarity	NPC183950
0.8973	High Similarity	NPC287101
0.8973	High Similarity	NPC223579
0.8973	High Similarity	NPC259713
0.8973	High Similarity	NPC17286
0.8973	High Similarity	NPC216318
0.8973	High Similarity	NPC296197

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 NPC214919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	437
0.1-0.2	999
0.2-0.3	1730
0.3-0.4	2734
0.4-0.5	1825
0.5-0.6	921
0.6-0.7	354
0.7-0.8	111
0.8-0.85	27
0.85-0.9	10
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9247	High Similarity	NPD2801	Approved
0.8816	High Similarity	NPD5494	Approved
0.88	High Similarity	NPD3817	Phase 2
0.8667	High Similarity	NPD1934	Approved
0.863	High Similarity	NPD1511	Approved
0.8553	High Similarity	NPD5402	Approved
0.8531	High Similarity	NPD2796	Approved
0.8514	High Similarity	NPD1512	Approved
0.8497	Intermediate Similarity	NPD3882	Suspended
0.8487	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD1247	Approved
0.8322	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8252	Intermediate Similarity	NPD1933	Approved
0.825	Intermediate Similarity	NPD3818	Discontinued
0.8239	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD6166	Phase 2
0.8221	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD7054	Approved
0.8176	Intermediate Similarity	NPD3926	Phase 2
0.8148	Intermediate Similarity	NPD7472	Approved
0.8133	Intermediate Similarity	NPD6799	Approved
0.8125	Intermediate Similarity	NPD447	Suspended
0.8092	Intermediate Similarity	NPD5403	Approved
0.8079	Intermediate Similarity	NPD5401	Approved
0.8038	Intermediate Similarity	NPD919	Approved
0.8037	Intermediate Similarity	NPD7074	Phase 3
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD7808	Phase 3
0.7988	Intermediate Similarity	NPD6797	Phase 2
0.7974	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7973	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7963	Intermediate Similarity	NPD7473	Discontinued
0.7959	Intermediate Similarity	NPD3748	Approved
0.7959	Intermediate Similarity	NPD1510	Phase 2
0.7939	Intermediate Similarity	NPD7251	Discontinued
0.7935	Intermediate Similarity	NPD4380	Phase 2
0.7919	Intermediate Similarity	NPD1549	Phase 2
0.7911	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7902	Intermediate Similarity	NPD6832	Phase 2
0.7898	Intermediate Similarity	NPD7819	Suspended
0.7898	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD5844	Phase 1
0.7862	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7843	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7834	Intermediate Similarity	NPD6801	Discontinued
0.7821	Intermediate Similarity	NPD6599	Discontinued
0.7808	Intermediate Similarity	NPD1240	Approved
0.7793	Intermediate Similarity	NPD2313	Discontinued
0.7786	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7785	Intermediate Similarity	NPD1551	Phase 2
0.7785	Intermediate Similarity	NPD2935	Discontinued
0.775	Intermediate Similarity	NPD7075	Discontinued
0.7742	Intermediate Similarity	NPD920	Approved
0.7703	Intermediate Similarity	NPD1607	Approved
0.7697	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7697	Intermediate Similarity	NPD3750	Approved
0.7682	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD7411	Suspended
0.7639	Intermediate Similarity	NPD2798	Approved
0.7632	Intermediate Similarity	NPD1243	Approved
0.7625	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2346	Discontinued
0.7613	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6844	Discontinued
0.7568	Intermediate Similarity	NPD943	Approved
0.7562	Intermediate Similarity	NPD1465	Phase 2
0.7554	Intermediate Similarity	NPD5536	Phase 2
0.7551	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7534	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD3226	Approved
0.7515	Intermediate Similarity	NPD6559	Discontinued
0.75	Intermediate Similarity	NPD6959	Discontinued
0.7484	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2799	Discontinued
0.747	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD7768	Phase 2
0.7466	Intermediate Similarity	NPD3018	Phase 2
0.7466	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7456	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.745	Intermediate Similarity	NPD1613	Approved
0.745	Intermediate Similarity	NPD4307	Phase 2
0.7448	Intermediate Similarity	NPD1203	Approved
0.7448	Intermediate Similarity	NPD3266	Approved
0.7448	Intermediate Similarity	NPD3267	Approved
0.741	Intermediate Similarity	NPD5242	Approved
0.7403	Intermediate Similarity	NPD2800	Approved
0.7397	Intermediate Similarity	NPD1019	Discontinued
0.7365	Intermediate Similarity	NPD3027	Phase 3
0.7362	Intermediate Similarity	NPD5019	Clinical (unspecified phase)
0.7361	Intermediate Similarity	NPD2981	Phase 2
0.7361	Intermediate Similarity	NPD9717	Approved
0.7358	Intermediate Similarity	NPD1653	Approved
0.7349	Intermediate Similarity	NPD3787	Discontinued
0.7342	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD6386	Approved
0.7329	Intermediate Similarity	NPD2797	Approved
0.7329	Intermediate Similarity	NPD6385	Approved
0.7325	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD6099	Approved
0.732	Intermediate Similarity	NPD6100	Approved
0.7317	Intermediate Similarity	NPD3749	Approved
0.7315	Intermediate Similarity	NPD3268	Approved
0.731	Intermediate Similarity	NPD2982	Phase 2
0.731	Intermediate Similarity	NPD2983	Phase 2
0.7301	Intermediate Similarity	NPD5353	Approved
0.729	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2654	Approved
0.7289	Intermediate Similarity	NPD7199	Phase 2
0.7285	Intermediate Similarity	NPD230	Phase 1
0.7284	Intermediate Similarity	NPD37	Approved
0.7278	Intermediate Similarity	NPD3751	Discontinued
0.7278	Intermediate Similarity	NPD2534	Approved
0.7278	Intermediate Similarity	NPD2533	Approved
0.7278	Intermediate Similarity	NPD2532	Approved
0.7273	Intermediate Similarity	NPD17	Approved
0.7262	Intermediate Similarity	NPD2403	Approved
0.7262	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7256	Intermediate Similarity	NPD4966	Approved
0.7256	Intermediate Similarity	NPD4965	Approved
0.7256	Intermediate Similarity	NPD4967	Phase 2
0.7255	Intermediate Similarity	NPD4308	Phase 3
0.7244	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD411	Approved
0.72	Intermediate Similarity	NPD1296	Phase 2
0.7192	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6234	Discontinued
0.7161	Intermediate Similarity	NPD2344	Approved
0.7152	Intermediate Similarity	NPD6233	Phase 2
0.7143	Intermediate Similarity	NPD3225	Approved
0.7143	Intermediate Similarity	NPD5283	Phase 1
0.7143	Intermediate Similarity	NPD1241	Discontinued
0.7143	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7033	Discontinued
0.7143	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4628	Phase 3
0.7133	Intermediate Similarity	NPD1548	Phase 1
0.7123	Intermediate Similarity	NPD1608	Approved
0.7107	Intermediate Similarity	NPD4357	Discontinued
0.7103	Intermediate Similarity	NPD3496	Discontinued
0.7069	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7067	Intermediate Similarity	NPD4908	Phase 1
0.7063	Intermediate Similarity	NPD4661	Approved
0.7063	Intermediate Similarity	NPD4662	Approved
0.7055	Intermediate Similarity	NPD422	Phase 1
0.7052	Intermediate Similarity	NPD5953	Discontinued
0.7051	Intermediate Similarity	NPD1471	Phase 3
0.7039	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD7286	Phase 2
0.7032	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD8313	Approved
0.7029	Intermediate Similarity	NPD8312	Approved
0.702	Intermediate Similarity	NPD4625	Phase 3
0.7013	Intermediate Similarity	NPD6651	Approved
0.7012	Intermediate Similarity	NPD5889	Approved
0.7012	Intermediate Similarity	NPD5890	Approved
0.7007	Intermediate Similarity	NPD3972	Approved
0.7	Intermediate Similarity	NPD9494	Approved
0.6988	Remote Similarity	NPD4288	Approved
0.6987	Remote Similarity	NPD3539	Phase 1
0.6981	Remote Similarity	NPD6190	Approved
0.6981	Remote Similarity	NPD2309	Approved
0.698	Remote Similarity	NPD1470	Approved
0.6974	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD6798	Discontinued
0.6973	Remote Similarity	NPD5006	Approved
0.6973	Remote Similarity	NPD5005	Approved
0.6971	Remote Similarity	NPD7549	Discontinued
0.6966	Remote Similarity	NPD5585	Approved
0.6962	Remote Similarity	NPD1652	Phase 2
0.6959	Remote Similarity	NPD4749	Approved
0.6957	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD1008	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD6585	Discontinued
0.6943	Remote Similarity	NPD3540	Phase 1
0.6943	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD1610	Phase 2
0.6939	Remote Similarity	NPD1201	Approved
0.6913	Remote Similarity	NPD1876	Approved
0.691	Remote Similarity	NPD8434	Phase 2
0.6909	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD6971	Discontinued
0.6894	Remote Similarity	NPD7390	Discontinued
0.689	Remote Similarity	NPD2649	Approved
0.689	Remote Similarity	NPD2651	Approved
0.689	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD2861	Phase 2
0.6879	Remote Similarity	NPD2163	Approved
0.6879	Remote Similarity	NPD7228	Approved
0.6875	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD9493	Approved
0.6854	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD3146	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