NPASS Compound

Structure

CID28274 OpenBabel06191715352D 25 27 0 0 0 0 0 0 0 0999 V2000 1.7321 -3.0000 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 1.7321 -1.0000 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 -0.0000 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 -2.5981 0.5000 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 -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 3.4641 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 3.4641 -1.0000 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 0.8660 0.5000 0.0000 C 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 -1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 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 2.5981 -2.5000 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 0.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 23 1 0 0 0 0 2 24 1 0 0 0 0 3 7 2 0 0 0 0 3 11 1 0 0 0 0 4 7 1 0 0 0 0 4 12 2 0 0 0 0 5 8 2 0 0 0 0 5 9 1 0 0 0 0 6 8 1 0 0 0 0 6 10 2 0 0 0 0 7 17 1 0 0 0 0 8 18 1 0 0 0 0 9 13 2 0 0 0 0 9 19 1 0 0 0 0 10 13 1 0 0 0 0 10 25 1 0 0 0 0 11 14 2 0 0 0 0 11 23 1 0 0 0 0 12 14 1 0 0 0 0 12 24 1 0 0 0 0 13 15 1 0 0 0 0 14 20 1 0 0 0 0 15 16 1 0 0 0 0 15 21 2 0 0 0 0 16 17 2 0 0 0 0 16 22 1 0 0 0 0 17 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.07
Volume:	326.149
LogP:	2.463
LogD:	2.095
LogS:	-3.817
# Rotatable Bonds:	3
TPSA:	129.59
# H-Bond Aceptor:	8
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.568
Synthetic Accessibility Score:	2.541
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.149
MDCK Permeability:	1.1232984434172977e-05
Pgp-inhibitor:	0.224
Pgp-substrate:	0.067
Human Intestinal Absorption (HIA):	0.109
20% Bioavailability (F20%):	0.012
30% Bioavailability (F30%):	0.756

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004
Plasma Protein Binding (PPB):	92.02046966552734%
Volume Distribution (VD):	0.799
Pgp-substrate:	14.298698425292969%

ADMET: Metabolism

CYP1A2-inhibitor:	0.901
CYP1A2-substrate:	0.94
CYP2C19-inhibitor:	0.052
CYP2C19-substrate:	0.055
CYP2C9-inhibitor:	0.611
CYP2C9-substrate:	0.757
CYP2D6-inhibitor:	0.361
CYP2D6-substrate:	0.304
CYP3A4-inhibitor:	0.456
CYP3A4-substrate:	0.106

ADMET: Excretion

Clearance (CL):	6.437
Half-life (T1/2):	0.925

ADMET: Toxicity

hERG Blockers:	0.143
Human Hepatotoxicity (H-HT):	0.053
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.429
Rat Oral Acute Toxicity:	0.063
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.82
Carcinogencity:	0.02
Eye Corrosion:	0.005
Eye Irritation:	0.894
Respiratory Toxicity:	0.13

Download Data

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

Natural Product: NPC28274

Natural Product ID:	NPC28274
*Common Name:**	Syringetin
IUPAC Name:	3,5,7-trihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)chromen-4-one
Synonyms:	Syringetin
Standard InCHIKey:	UZMAPBJVXOGOFT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O8/c1-23-11-3-7(4-12(24-2)14(11)20)17-16(22)15(21)13-9(19)5-8(18)6-10(13)25-17/h3-6,18-20,22H,1-2H3
SMILES:	COc1cc(cc(c1O)OC)c1oc2cc(O)cc(c2c(=O)c1O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL489142
PubChem CID:	5281953
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones [CHEMONTID:0001136] Flavonols

*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
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(01)00320-X]
NPO21179	Streptomyces griseoaurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10048567]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11738417]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919095]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21462031]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	flower buds and leaves	Khon Kaen province, Thailand	2010	PMID[23270663]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[23642481]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[26462418]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Rhizome	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14307	Rhizopus oryzae	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23157	Wigandia kunthii	Species	Namaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18881	Loropetalum chinense	Species	Hamamelidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22147	Goniothalamus macrophyllus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14307	Rhizopus oryzae	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21894	Psychotria granadensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13308	Polycitor adriaticus	Species	Polycitoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22968	Elaeocarpus serratus	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21179	Streptomyces griseoaurantiacus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15469	Myodocarpus gracilis	Species	Myodocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22530	Vigna luteola	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6953.1	Aconitum sachalinense subsp. yezoense	Subspecies	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20425	Epimedium macranthum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3478	Nelumbo nucifera	Species	Nelumbonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23194	Berberis beaniana	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26293	Ginkgo biloba	Species	Ginkgoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21704	Papaver suaveolens	Species	Papaveraceae	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	3
Others	4

Activity Type	# Activity
Individual Protein	4
Organism	1
Others	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT13	Individual Protein	Tyrosine-protein kinase LCK	Homo sapiens	IC50	=	20.0	ug.mL-1	PMID[522389]
NPT1443	Individual Protein	Pyruvate dehydrogenase kinase isoform 1	Homo sapiens	Inhibition	=	14.98	%	PMID[522393]
NPT2	Others	Unspecified		IC50	=	24.0	ug.mL-1	PMID[522388]
NPT2	Others	Unspecified		IC50	=	2100.0	nM	PMID[522390]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	FC	=	1.9	n.a.	PMID[522391]
NPT99	Individual Protein	Peroxisome proliferator-activated receptor gamma	Homo sapiens	FC	=	1.2	n.a.	PMID[522391]
NPT191	Organism	Hepatitis C virus	Hepatitis C virus	EC50	=	15500.0	nM	PMID[522392]
NPT27	Others	Unspecified		CC50	>	50000.0	nM	PMID[522392]

☑ 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 NPC28274 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	455
0.1-0.2	2054
0.2-0.3	5050
0.3-0.4	11264
0.4-0.5	6005
0.5-0.6	3945
0.6-0.7	5032
0.7-0.8	4686
0.8-0.85	2103
0.85-0.9	1253
0.9-0.95	573
0.95-1	277

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133953
1.0	High Similarity	NPC50403
0.9931	High Similarity	NPC123886
0.9863	High Similarity	NPC162351
0.9863	High Similarity	NPC58382
0.9862	High Similarity	NPC200740
0.9862	High Similarity	NPC125062
0.9862	High Similarity	NPC252933
0.9862	High Similarity	NPC54394
0.9795	High Similarity	NPC82325
0.9795	High Similarity	NPC279989
0.9795	High Similarity	NPC55205
0.9793	High Similarity	NPC219330
0.9792	High Similarity	NPC120464
0.973	High Similarity	NPC55619
0.973	High Similarity	NPC100916
0.973	High Similarity	NPC200388
0.973	High Similarity	NPC247017
0.973	High Similarity	NPC98661
0.973	High Similarity	NPC474520
0.9728	High Similarity	NPC236223
0.9728	High Similarity	NPC270620
0.9728	High Similarity	NPC179126
0.9728	High Similarity	NPC78326
0.9726	High Similarity	NPC76376
0.9724	High Similarity	NPC223579
0.9724	High Similarity	NPC48479
0.9724	High Similarity	NPC183950
0.9724	High Similarity	NPC159103
0.9724	High Similarity	NPC177298
0.9724	High Similarity	NPC87125
0.9724	High Similarity	NPC270465
0.9724	High Similarity	NPC287101
0.9724	High Similarity	NPC52005
0.9724	High Similarity	NPC137062
0.9664	High Similarity	NPC93376
0.9664	High Similarity	NPC29841
0.9664	High Similarity	NPC174908
0.9664	High Similarity	NPC189179
0.9664	High Similarity	NPC472438
0.9664	High Similarity	NPC224137
0.9664	High Similarity	NPC163524
0.9664	High Similarity	NPC227192
0.9664	High Similarity	NPC78302
0.9664	High Similarity	NPC235215
0.9664	High Similarity	NPC287979
0.9664	High Similarity	NPC176665
0.9664	High Similarity	NPC305663
0.9664	High Similarity	NPC7973
0.9664	High Similarity	NPC75215
0.9662	High Similarity	NPC26227
0.9662	High Similarity	NPC201451
0.9662	High Similarity	NPC44079
0.9658	High Similarity	NPC188871
0.9658	High Similarity	NPC149127
0.9658	High Similarity	NPC50728
0.9658	High Similarity	NPC286342
0.9658	High Similarity	NPC166753
0.9653	High Similarity	NPC169749
0.96	High Similarity	NPC261004
0.96	High Similarity	NPC22472
0.96	High Similarity	NPC176300
0.96	High Similarity	NPC19687
0.96	High Similarity	NPC105242
0.96	High Similarity	NPC4481
0.96	High Similarity	NPC288669
0.96	High Similarity	NPC7846
0.96	High Similarity	NPC18607
0.96	High Similarity	NPC25495
0.96	High Similarity	NPC115798
0.96	High Similarity	NPC9609
0.96	High Similarity	NPC18772
0.96	High Similarity	NPC143828
0.96	High Similarity	NPC191459
0.96	High Similarity	NPC300943
0.96	High Similarity	NPC152166
0.96	High Similarity	NPC253634
0.96	High Similarity	NPC204854
0.96	High Similarity	NPC130894
0.9597	High Similarity	NPC250922
0.9597	High Similarity	NPC43243
0.9597	High Similarity	NPC265511
0.9597	High Similarity	NPC49824
0.9597	High Similarity	NPC245546
0.9597	High Similarity	NPC268161
0.9597	High Similarity	NPC266960
0.9595	High Similarity	NPC75279
0.9595	High Similarity	NPC246204
0.9595	High Similarity	NPC250822
0.9595	High Similarity	NPC276409
0.9592	High Similarity	NPC260895
0.9592	High Similarity	NPC236769
0.9586	High Similarity	NPC33265
0.9586	High Similarity	NPC62536
0.9586	High Similarity	NPC12200
0.9586	High Similarity	NPC108406
0.9533	High Similarity	NPC101830
0.9533	High Similarity	NPC203891
0.9533	High Similarity	NPC110070
0.953	High Similarity	NPC163780
0.953	High Similarity	NPC208197
0.953	High Similarity	NPC50715
0.953	High Similarity	NPC92659
0.953	High Similarity	NPC201136
0.953	High Similarity	NPC128863
0.953	High Similarity	NPC214138
0.953	High Similarity	NPC138360
0.953	High Similarity	NPC183597
0.953	High Similarity	NPC196439
0.953	High Similarity	NPC167815
0.953	High Similarity	NPC146165
0.953	High Similarity	NPC2476
0.953	High Similarity	NPC4455
0.953	High Similarity	NPC227325
0.953	High Similarity	NPC280339
0.9527	High Similarity	NPC256283
0.9527	High Similarity	NPC239128
0.9527	High Similarity	NPC71334
0.9527	High Similarity	NPC198826
0.9527	High Similarity	NPC301123
0.9527	High Similarity	NPC120163
0.9527	High Similarity	NPC222830
0.9527	High Similarity	NPC188203
0.9527	High Similarity	NPC275836
0.9527	High Similarity	NPC275722
0.9527	High Similarity	NPC471982
0.9527	High Similarity	NPC142540
0.9527	High Similarity	NPC60972
0.9527	High Similarity	NPC241498
0.9527	High Similarity	NPC100887
0.9527	High Similarity	NPC131624
0.9527	High Similarity	NPC25270
0.9527	High Similarity	NPC27208
0.9527	High Similarity	NPC293183
0.9527	High Similarity	NPC187498
0.9527	High Similarity	NPC39732
0.9527	High Similarity	NPC83508
0.9527	High Similarity	NPC212678
0.9527	High Similarity	NPC57030
0.9527	High Similarity	NPC301323
0.9527	High Similarity	NPC162313
0.9527	High Similarity	NPC156222
0.9521	High Similarity	NPC261548
0.9521	High Similarity	NPC195202
0.9517	High Similarity	NPC179271
0.9517	High Similarity	NPC20791
0.947	High Similarity	NPC193842
0.9467	High Similarity	NPC13858
0.9467	High Similarity	NPC178854
0.9467	High Similarity	NPC292107
0.9467	High Similarity	NPC326037
0.9467	High Similarity	NPC320825
0.9463	High Similarity	NPC47781
0.9463	High Similarity	NPC22519
0.9463	High Similarity	NPC176775
0.9463	High Similarity	NPC160951
0.9463	High Similarity	NPC274327
0.9463	High Similarity	NPC231018
0.9463	High Similarity	NPC255350
0.9463	High Similarity	NPC145379
0.9463	High Similarity	NPC69394
0.9463	High Similarity	NPC183878
0.9463	High Similarity	NPC86485
0.9459	High Similarity	NPC225731
0.9459	High Similarity	NPC304295
0.9459	High Similarity	NPC59162
0.9459	High Similarity	NPC205046
0.9456	High Similarity	NPC328119
0.9452	High Similarity	NPC51443
0.9452	High Similarity	NPC74881
0.9444	High Similarity	NPC175013
0.9408	High Similarity	NPC470326
0.9408	High Similarity	NPC246478
0.9404	High Similarity	NPC471479
0.9404	High Similarity	NPC52530
0.9404	High Similarity	NPC471515
0.9404	High Similarity	NPC67876
0.94	High Similarity	NPC133392
0.94	High Similarity	NPC189960
0.94	High Similarity	NPC80534
0.94	High Similarity	NPC213622
0.94	High Similarity	NPC56786
0.94	High Similarity	NPC20830
0.94	High Similarity	NPC32557
0.94	High Similarity	NPC256612
0.9396	High Similarity	NPC19721
0.9396	High Similarity	NPC37684
0.9396	High Similarity	NPC304954
0.9396	High Similarity	NPC63187
0.9396	High Similarity	NPC302950
0.9396	High Similarity	NPC236637
0.9396	High Similarity	NPC219582
0.9396	High Similarity	NPC134677
0.9396	High Similarity	NPC157784
0.9392	High Similarity	NPC184136
0.9392	High Similarity	NPC77858
0.9392	High Similarity	NPC306821
0.9388	High Similarity	NPC119059
0.9379	High Similarity	NPC279121
0.9351	High Similarity	NPC470459

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 NPC28274 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	438
0.1-0.2	1007
0.2-0.3	1917
0.3-0.4	2657
0.4-0.5	1678
0.5-0.6	957
0.6-0.7	332
0.7-0.8	106
0.8-0.85	37
0.85-0.9	9
0.9-0.95	8
0.95-1	4

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9517	High Similarity	NPD1512	Approved
0.9463	High Similarity	NPD2801	Approved
0.9396	High Similarity	NPD1934	Approved
0.9379	High Similarity	NPD1511	Approved
0.9272	High Similarity	NPD3817	Phase 2
0.9211	High Similarity	NPD3882	Suspended
0.9167	High Similarity	NPD6166	Phase 2
0.9167	High Similarity	NPD6167	Clinical (unspecified phase)
0.9167	High Similarity	NPD6168	Clinical (unspecified phase)
0.9079	High Similarity	NPD2393	Clinical (unspecified phase)
0.8926	High Similarity	NPD4378	Clinical (unspecified phase)
0.8882	High Similarity	NPD6797	Phase 2
0.8875	High Similarity	NPD7054	Approved
0.8827	High Similarity	NPD7251	Discontinued
0.882	High Similarity	NPD7472	Approved
0.8812	High Similarity	NPD3818	Discontinued
0.8773	High Similarity	NPD4338	Clinical (unspecified phase)
0.8773	High Similarity	NPD7808	Phase 3
0.8704	High Similarity	NPD7074	Phase 3
0.8599	High Similarity	NPD4868	Clinical (unspecified phase)
0.8544	High Similarity	NPD7075	Discontinued
0.8516	High Similarity	NPD4380	Phase 2
0.8487	Intermediate Similarity	NPD6799	Approved
0.8456	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8456	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8446	Intermediate Similarity	NPD1510	Phase 2
0.8428	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8408	Intermediate Similarity	NPD6801	Discontinued
0.84	Intermediate Similarity	NPD1549	Phase 2
0.8354	Intermediate Similarity	NPD1465	Phase 2
0.8354	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6232	Discontinued
0.8313	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8303	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8302	Intermediate Similarity	NPD5402	Approved
0.8299	Intermediate Similarity	NPD1240	Approved
0.8293	Intermediate Similarity	NPD7473	Discontinued
0.8278	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8267	Intermediate Similarity	NPD2796	Approved
0.821	Intermediate Similarity	NPD5494	Approved
0.8205	Intermediate Similarity	NPD5403	Approved
0.8194	Intermediate Similarity	NPD5401	Approved
0.8188	Intermediate Similarity	NPD1607	Approved
0.8176	Intermediate Similarity	NPD943	Approved
0.8171	Intermediate Similarity	NPD3926	Phase 2
0.8165	Intermediate Similarity	NPD6599	Discontinued
0.816	Intermediate Similarity	NPD1247	Approved
0.8148	Intermediate Similarity	NPD919	Approved
0.8125	Intermediate Similarity	NPD7819	Suspended
0.8082	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8049	Intermediate Similarity	NPD6959	Discontinued
0.8027	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD7411	Suspended
0.8	Intermediate Similarity	NPD230	Phase 1
0.7961	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD3750	Approved
0.7933	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1613	Approved
0.7881	Intermediate Similarity	NPD447	Suspended
0.7871	Intermediate Similarity	NPD2800	Approved
0.787	Intermediate Similarity	NPD5844	Phase 1
0.7862	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7836	Intermediate Similarity	NPD6559	Discontinued
0.7792	Intermediate Similarity	NPD1551	Phase 2
0.7738	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD3027	Phase 3
0.7692	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2935	Discontinued
0.7658	Intermediate Similarity	NPD6190	Approved
0.7651	Intermediate Similarity	NPD3749	Approved
0.7647	Intermediate Similarity	NPD1933	Approved
0.7643	Intermediate Similarity	NPD1243	Approved
0.7625	Intermediate Similarity	NPD2533	Approved
0.7625	Intermediate Similarity	NPD2532	Approved
0.7625	Intermediate Similarity	NPD2534	Approved
0.7619	Intermediate Similarity	NPD7199	Phase 2
0.7613	Intermediate Similarity	NPD3748	Approved
0.7605	Intermediate Similarity	NPD6234	Discontinued
0.7602	Intermediate Similarity	NPD3751	Discontinued
0.76	Intermediate Similarity	NPD9494	Approved
0.7597	Intermediate Similarity	NPD6651	Approved
0.7595	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1653	Approved
0.759	Intermediate Similarity	NPD7768	Phase 2
0.7568	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD6099	Approved
0.7564	Intermediate Similarity	NPD6100	Approved
0.7562	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD3226	Approved
0.7532	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD920	Approved
0.7516	Intermediate Similarity	NPD2344	Approved
0.75	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD4628	Phase 3
0.7471	Intermediate Similarity	NPD3787	Discontinued
0.7467	Intermediate Similarity	NPD1203	Approved
0.7458	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD7390	Discontinued
0.7451	Intermediate Similarity	NPD2313	Discontinued
0.7446	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.743	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD37	Approved
0.7407	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1548	Phase 1
0.7391	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD9269	Phase 2
0.7381	Intermediate Similarity	NPD4966	Approved
0.7381	Intermediate Similarity	NPD4967	Phase 2
0.7381	Intermediate Similarity	NPD4965	Approved
0.7377	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7371	Intermediate Similarity	NPD5953	Discontinued
0.7348	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD7685	Pre-registration
0.7329	Intermediate Similarity	NPD2309	Approved
0.732	Intermediate Similarity	NPD6832	Phase 2
0.7315	Intermediate Similarity	NPD422	Phase 1
0.7308	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7228	Approved
0.7296	Intermediate Similarity	NPD2346	Discontinued
0.7283	Intermediate Similarity	NPD2403	Approved
0.7278	Intermediate Similarity	NPD2799	Discontinued
0.7267	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD9717	Approved
0.7257	Intermediate Similarity	NPD7286	Phase 2
0.7255	Intermediate Similarity	NPD3018	Phase 2
0.7226	Intermediate Similarity	NPD3268	Approved
0.7226	Intermediate Similarity	NPD6798	Discontinued
0.7222	Intermediate Similarity	NPD8434	Phase 2
0.7208	Intermediate Similarity	NPD4908	Phase 1
0.7205	Intermediate Similarity	NPD2654	Approved
0.72	Intermediate Similarity	NPD1610	Phase 2
0.72	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2798	Approved
0.7184	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD6233	Phase 2
0.7171	Intermediate Similarity	NPD3225	Approved
0.717	Intermediate Similarity	NPD4308	Phase 3
0.717	Intermediate Similarity	NPD7033	Discontinued
0.7152	Intermediate Similarity	NPD1608	Approved
0.7126	Intermediate Similarity	NPD5242	Approved
0.7124	Intermediate Similarity	NPD2797	Approved
0.7118	Intermediate Similarity	NPD5353	Approved
0.7117	Intermediate Similarity	NPD2354	Approved
0.7115	Intermediate Similarity	NPD411	Approved
0.7115	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD9268	Approved
0.7105	Intermediate Similarity	NPD2983	Phase 2
0.7105	Intermediate Similarity	NPD2982	Phase 2
0.7095	Intermediate Similarity	NPD5536	Phase 2
0.7089	Intermediate Similarity	NPD6355	Discontinued
0.7081	Intermediate Similarity	NPD4363	Phase 3
0.7081	Intermediate Similarity	NPD4360	Phase 2
0.7074	Intermediate Similarity	NPD6782	Approved
0.7074	Intermediate Similarity	NPD6781	Approved
0.7074	Intermediate Similarity	NPD6779	Approved
0.7074	Intermediate Similarity	NPD6778	Approved
0.7074	Intermediate Similarity	NPD6777	Approved
0.7074	Intermediate Similarity	NPD6776	Approved
0.7074	Intermediate Similarity	NPD6780	Approved
0.7069	Intermediate Similarity	NPD5710	Approved
0.7069	Intermediate Similarity	NPD5711	Approved
0.7056	Intermediate Similarity	NPD8313	Approved
0.7056	Intermediate Similarity	NPD8312	Approved
0.7041	Intermediate Similarity	NPD6386	Approved
0.7041	Intermediate Similarity	NPD6385	Approved
0.7039	Intermediate Similarity	NPD2981	Phase 2
0.7034	Intermediate Similarity	NPD228	Approved
0.7033	Intermediate Similarity	NPD8150	Discontinued
0.7031	Intermediate Similarity	NPD7584	Approved
0.703	Intermediate Similarity	NPD4357	Discontinued
0.7025	Intermediate Similarity	NPD4060	Phase 1
0.7018	Intermediate Similarity	NPD4288	Approved
0.7013	Intermediate Similarity	NPD3266	Approved
0.7013	Intermediate Similarity	NPD3267	Approved
0.7006	Intermediate Similarity	NPD2163	Approved
0.7	Intermediate Similarity	NPD6844	Discontinued
0.6994	Remote Similarity	NPD1652	Phase 2
0.6993	Remote Similarity	NPD4749	Approved
0.6988	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7266	Discontinued
0.6975	Remote Similarity	NPD1471	Phase 3
0.6974	Remote Similarity	NPD1201	Approved
0.6963	Remote Similarity	NPD7435	Discontinued
0.6959	Remote Similarity	NPD8151	Discontinued
0.6954	Remote Similarity	NPD17	Approved
0.6952	Remote Similarity	NPD4361	Phase 2
0.6952	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6943	Remote Similarity	NPD4625	Phase 3
0.6943	Remote Similarity	NPD7095	Approved
0.6933	Remote Similarity	NPD9545	Approved
0.6918	Remote Similarity	NPD4307	Phase 2
0.6918	Remote Similarity	NPD1558	Phase 1
0.6913	Remote Similarity	NPD9493	Approved
0.6903	Remote Similarity	NPD1470	Approved
0.6899	Remote Similarity	NPD1296	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data