NPASS Compound

Structure

CID142540 OpenBabel06191715502D 25 27 0 0 0 0 0 0 0 0999 V2000 -1.7321 2.0000 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 -2.5981 -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 2.5981 1.5000 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 -1.7321 -1.0000 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 1.7321 2.0000 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 2.5981 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 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 -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 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 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 1.7321 3.0000 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 3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 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 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 4 2 0 0 0 0 3 7 1 0 0 0 0 4 8 1 0 0 0 0 5 9 2 0 0 0 0 5 11 1 0 0 0 0 6 10 1 0 0 0 0 6 12 2 0 0 0 0 7 14 2 0 0 0 0 7 18 1 0 0 0 0 8 15 2 0 0 0 0 8 19 1 0 0 0 0 9 13 1 0 0 0 0 9 20 1 0 0 0 0 10 13 1 0 0 0 0 10 21 2 0 0 0 0 11 16 2 0 0 0 0 11 22 1 0 0 0 0 12 14 1 0 0 0 0 12 25 1 0 0 0 0 13 17 2 0 0 0 0 14 15 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 24 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:	2.7
LogD:	2.25
LogS:	-3.954
# 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:	0.532
Synthetic Accessibility Score:	2.81
Fsp3:	0.118
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.163
MDCK Permeability:	1.0506605576665606e-05
Pgp-inhibitor:	0.018
Pgp-substrate:	0.018
Human Intestinal Absorption (HIA):	0.167
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002
Plasma Protein Binding (PPB):	91.92269897460938%
Volume Distribution (VD):	0.578
Pgp-substrate:	17.298133850097656%

ADMET: Metabolism

CYP1A2-inhibitor:	0.94
CYP1A2-substrate:	0.937
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.641
CYP2C9-substrate:	0.844
CYP2D6-inhibitor:	0.103
CYP2D6-substrate:	0.313
CYP3A4-inhibitor:	0.286
CYP3A4-substrate:	0.141

ADMET: Excretion

Clearance (CL):	5.197
Half-life (T1/2):	0.771

ADMET: Toxicity

hERG Blockers:	0.092
Human Hepatotoxicity (H-HT):	0.058
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.624
Rat Oral Acute Toxicity:	0.08
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.457
Carcinogencity:	0.035
Eye Corrosion:	0.003
Eye Irritation:	0.907
Respiratory Toxicity:	0.111

Download Data

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

Natural Product: NPC142540

Natural Product ID:	NPC142540
*Common Name:**	Viscidulin Iii
IUPAC Name:	2-(3,6-dihydroxy-2-methoxyphenyl)-5,7-dihydroxy-8-methoxychromen-4-one
Synonyms:
Standard InCHIKey:	CPFJPTACQDZPLS-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C17H14O8/c1-23-15-8(19)4-3-7(18)14(15)12-6-10(21)13-9(20)5-11(22)16(24-2)17(13)25-12/h3-6,18-20,22H,1-2H3
SMILES:	COc1c(O)ccc(c1c1cc(=O)c2c(o1)c(OC)c(cc2O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465771
PubChem CID:	5271991
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0002585] O-methylated flavonoids [CHEMONTID:0002593] 8-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
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713409]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[19555121]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19555121]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19829679]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[21087019]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22314230]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23521110]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26562741]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29517238]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31625751]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	Along the Valencian coast, Spain	2020-Jun&Jul	PMID[35161358]
NPO29667	Scutellariae radix	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9214730]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834167]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Herb	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21524	Scutellaria hypericifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25459	Scutellaria rehderiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21524	Scutellaria hypericifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25459	Scutellaria rehderiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31378	Scutellaria balcalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25459	Scutellaria rehderiana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21524	Scutellaria hypericifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4640	Portulaca oleracea	Species	Portulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9096	Scutellaria lateriflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21524	Scutellaria hypericifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19994	Scutellaria viscidula	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28877	Scutellaria baicalensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25459	Scutellaria rehderiana	Species	Lamiaceae	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	1
Others	2

Activity Type	# Activity
Cell Line	2
Protein Family	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT380	Cell Line	U-251	Homo sapiens	Activity	=	87.53	%	PMID[550638]
NPT76	Cell Line	C6	Rattus norvegicus	Activity	=	57.74	%	PMID[550638]
NPT1644	Protein Family	Trypsin	Homo sapiens	IC50	=	88000.0	nM	PMID[550637]

☑ 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 NPC142540 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	467
0.1-0.2	2120
0.2-0.3	5581
0.3-0.4	11648
0.4-0.5	5228
0.5-0.6	4216
0.6-0.7	5090
0.7-0.8	4817
0.8-0.85	1829
0.85-0.9	962
0.9-0.95	533
0.95-1	206

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC146165
0.9864	High Similarity	NPC163780
0.9864	High Similarity	NPC201136
0.9864	High Similarity	NPC167815
0.9864	High Similarity	NPC128863
0.9864	High Similarity	NPC227325
0.9864	High Similarity	NPC2476
0.9864	High Similarity	NPC280339
0.9864	High Similarity	NPC183597
0.9864	High Similarity	NPC4455
0.9864	High Similarity	NPC138360
0.9864	High Similarity	NPC92659
0.9864	High Similarity	NPC50715
0.9864	High Similarity	NPC196439
0.9863	High Similarity	NPC25270
0.9863	High Similarity	NPC71334
0.9863	High Similarity	NPC100887
0.9863	High Similarity	NPC275836
0.9863	High Similarity	NPC198826
0.9863	High Similarity	NPC212678
0.9863	High Similarity	NPC120163
0.9863	High Similarity	NPC57030
0.9863	High Similarity	NPC131624
0.9863	High Similarity	NPC301323
0.9863	High Similarity	NPC156222
0.9863	High Similarity	NPC241498
0.9863	High Similarity	NPC162313
0.9863	High Similarity	NPC275722
0.9863	High Similarity	NPC83508
0.9863	High Similarity	NPC188203
0.9863	High Similarity	NPC222830
0.9863	High Similarity	NPC239128
0.9863	High Similarity	NPC187498
0.9863	High Similarity	NPC293183
0.9863	High Similarity	NPC256283
0.9797	High Similarity	NPC98661
0.9797	High Similarity	NPC247017
0.9796	High Similarity	NPC231018
0.9796	High Similarity	NPC276409
0.9796	High Similarity	NPC47781
0.9796	High Similarity	NPC255350
0.9796	High Similarity	NPC250822
0.9796	High Similarity	NPC75279
0.9796	High Similarity	NPC22519
0.9796	High Similarity	NPC160951
0.9796	High Similarity	NPC69394
0.9796	High Similarity	NPC274327
0.9796	High Similarity	NPC183878
0.9796	High Similarity	NPC145379
0.9796	High Similarity	NPC176775
0.9732	High Similarity	NPC305663
0.9732	High Similarity	NPC287979
0.9732	High Similarity	NPC75215
0.9732	High Similarity	NPC227192
0.9732	High Similarity	NPC176665
0.9732	High Similarity	NPC224137
0.9732	High Similarity	NPC163524
0.9732	High Similarity	NPC189179
0.9732	High Similarity	NPC93376
0.973	High Similarity	NPC208197
0.973	High Similarity	NPC44079
0.973	High Similarity	NPC213622
0.973	High Similarity	NPC201451
0.973	High Similarity	NPC256612
0.973	High Similarity	NPC26227
0.973	High Similarity	NPC20830
0.9726	High Similarity	NPC184136
0.9726	High Similarity	NPC306821
0.9667	High Similarity	NPC143828
0.9667	High Similarity	NPC300943
0.9667	High Similarity	NPC191459
0.9667	High Similarity	NPC4481
0.9667	High Similarity	NPC152166
0.9667	High Similarity	NPC204854
0.9667	High Similarity	NPC22472
0.9667	High Similarity	NPC19687
0.9667	High Similarity	NPC7846
0.9667	High Similarity	NPC288669
0.9667	High Similarity	NPC105242
0.9667	High Similarity	NPC176300
0.9667	High Similarity	NPC253634
0.9667	High Similarity	NPC115798
0.9667	High Similarity	NPC193842
0.9667	High Similarity	NPC25495
0.9667	High Similarity	NPC9609
0.9667	High Similarity	NPC18607
0.9667	High Similarity	NPC261004
0.9667	High Similarity	NPC18772
0.9667	High Similarity	NPC130894
0.9664	High Similarity	NPC49824
0.9664	High Similarity	NPC268161
0.9664	High Similarity	NPC245546
0.9664	High Similarity	NPC43243
0.9664	High Similarity	NPC474520
0.9664	High Similarity	NPC266960
0.966	High Similarity	NPC226973
0.966	High Similarity	NPC208043
0.9658	High Similarity	NPC17286
0.9658	High Similarity	NPC216318
0.9658	High Similarity	NPC259713
0.9658	High Similarity	NPC223579
0.9658	High Similarity	NPC287101
0.9658	High Similarity	NPC296197
0.9658	High Similarity	NPC183950
0.9658	High Similarity	NPC137062
0.9658	High Similarity	NPC52005
0.96	High Similarity	NPC110070
0.96	High Similarity	NPC78302
0.96	High Similarity	NPC472438
0.96	High Similarity	NPC7973
0.96	High Similarity	NPC29841
0.96	High Similarity	NPC203891
0.96	High Similarity	NPC235215
0.96	High Similarity	NPC470402
0.96	High Similarity	NPC101830
0.9597	High Similarity	NPC2928
0.9597	High Similarity	NPC214138
0.9595	High Similarity	NPC39732
0.9595	High Similarity	NPC199100
0.9595	High Similarity	NPC120537
0.9595	High Similarity	NPC180234
0.9595	High Similarity	NPC39007
0.9595	High Similarity	NPC27208
0.9595	High Similarity	NPC301123
0.9595	High Similarity	NPC60972
0.9595	High Similarity	NPC161277
0.9592	High Similarity	NPC45873
0.9589	High Similarity	NPC120464
0.9533	High Similarity	NPC100916
0.9533	High Similarity	NPC255106
0.9533	High Similarity	NPC235165
0.9533	High Similarity	NPC55619
0.9533	High Similarity	NPC200388
0.9533	High Similarity	NPC292107
0.9533	High Similarity	NPC472916
0.9533	High Similarity	NPC178854
0.953	High Similarity	NPC271779
0.953	High Similarity	NPC167091
0.953	High Similarity	NPC88645
0.953	High Similarity	NPC86485
0.953	High Similarity	NPC206238
0.953	High Similarity	NPC292214
0.9527	High Similarity	NPC125062
0.9527	High Similarity	NPC133953
0.9527	High Similarity	NPC54394
0.9527	High Similarity	NPC252933
0.9527	High Similarity	NPC28274
0.9527	High Similarity	NPC225731
0.9527	High Similarity	NPC171010
0.9527	High Similarity	NPC117579
0.9527	High Similarity	NPC200740
0.9527	High Similarity	NPC50403
0.9527	High Similarity	NPC308451
0.9524	High Similarity	NPC48479
0.9524	High Similarity	NPC177298
0.9524	High Similarity	NPC328119
0.9521	High Similarity	NPC30647
0.9521	High Similarity	NPC61871
0.9521	High Similarity	NPC12200
0.9521	High Similarity	NPC108406
0.9521	High Similarity	NPC275772
0.9521	High Similarity	NPC55557
0.9521	High Similarity	NPC239312
0.9521	High Similarity	NPC130230
0.9474	High Similarity	NPC476980
0.947	High Similarity	NPC472910
0.947	High Similarity	NPC472911
0.947	High Similarity	NPC99597
0.947	High Similarity	NPC210084
0.947	High Similarity	NPC475267
0.947	High Similarity	NPC472913
0.947	High Similarity	NPC472914
0.947	High Similarity	NPC156057
0.947	High Similarity	NPC474208
0.947	High Similarity	NPC78225
0.947	High Similarity	NPC474836
0.947	High Similarity	NPC162869
0.947	High Similarity	NPC222814
0.947	High Similarity	NPC96167
0.947	High Similarity	NPC48208
0.947	High Similarity	NPC245758
0.9467	High Similarity	NPC32557
0.9467	High Similarity	NPC189960
0.9463	High Similarity	NPC245382
0.9463	High Similarity	NPC82325
0.9463	High Similarity	NPC100971
0.9463	High Similarity	NPC216769
0.9463	High Similarity	NPC134677
0.9463	High Similarity	NPC291802
0.9463	High Similarity	NPC121522
0.9463	High Similarity	NPC101996
0.9463	High Similarity	NPC209487
0.9463	High Similarity	NPC269451
0.9463	High Similarity	NPC279989
0.9463	High Similarity	NPC123886
0.9463	High Similarity	NPC100263
0.9463	High Similarity	NPC35763
0.9463	High Similarity	NPC55205
0.9463	High Similarity	NPC181209
0.9463	High Similarity	NPC131266

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 NPC142540 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	446
0.1-0.2	1022
0.2-0.3	2005
0.3-0.4	2669
0.4-0.5	1628
0.5-0.6	935
0.6-0.7	301
0.7-0.8	99
0.8-0.85	26
0.85-0.9	11
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9796	High Similarity	NPD2801	Approved
0.9333	High Similarity	NPD1934	Approved
0.9315	High Similarity	NPD1511	Approved
0.9189	High Similarity	NPD1512	Approved
0.9026	High Similarity	NPD3882	Suspended
0.902	High Similarity	NPD2393	Clinical (unspecified phase)
0.8961	High Similarity	NPD3817	Phase 2
0.8875	High Similarity	NPD3818	Discontinued
0.8868	High Similarity	NPD6168	Clinical (unspecified phase)
0.8868	High Similarity	NPD6167	Clinical (unspecified phase)
0.8868	High Similarity	NPD6166	Phase 2
0.8834	High Similarity	NPD4338	Clinical (unspecified phase)
0.882	High Similarity	NPD7054	Approved
0.8765	High Similarity	NPD7472	Approved
0.865	High Similarity	NPD7074	Phase 3
0.8618	High Similarity	NPD4378	Clinical (unspecified phase)
0.8598	High Similarity	NPD6797	Phase 2
0.8545	High Similarity	NPD7251	Discontinued
0.8544	High Similarity	NPD4868	Clinical (unspecified phase)
0.85	High Similarity	NPD5494	Approved
0.8494	Intermediate Similarity	NPD7808	Phase 3
0.8462	Intermediate Similarity	NPD4380	Phase 2
0.8418	Intermediate Similarity	NPD1465	Phase 2
0.84	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.84	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8395	Intermediate Similarity	NPD6232	Discontinued
0.8389	Intermediate Similarity	NPD1510	Phase 2
0.8375	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8365	Intermediate Similarity	NPD5402	Approved
0.8354	Intermediate Similarity	NPD7473	Discontinued
0.8344	Intermediate Similarity	NPD1549	Phase 2
0.8261	Intermediate Similarity	NPD7075	Discontinued
0.8258	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8243	Intermediate Similarity	NPD943	Approved
0.8243	Intermediate Similarity	NPD1240	Approved
0.8239	Intermediate Similarity	NPD6801	Discontinued
0.8221	Intermediate Similarity	NPD1247	Approved
0.8212	Intermediate Similarity	NPD2796	Approved
0.8194	Intermediate Similarity	NPD6799	Approved
0.8133	Intermediate Similarity	NPD1607	Approved
0.8105	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD7819	Suspended
0.8075	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.8036	Intermediate Similarity	NPD5844	Phase 1
0.8025	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD3926	Phase 2
0.8	Intermediate Similarity	NPD6959	Discontinued
0.7973	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.795	Intermediate Similarity	NPD7411	Suspended
0.7947	Intermediate Similarity	NPD230	Phase 1
0.7947	Intermediate Similarity	NPD447	Suspended
0.7935	Intermediate Similarity	NPD2800	Approved
0.7925	Intermediate Similarity	NPD5403	Approved
0.7911	Intermediate Similarity	NPD5401	Approved
0.7905	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD6599	Discontinued
0.7885	Intermediate Similarity	NPD3750	Approved
0.7881	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7881	Intermediate Similarity	NPD1613	Approved
0.7879	Intermediate Similarity	NPD919	Approved
0.7857	Intermediate Similarity	NPD2935	Discontinued
0.7812	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD6559	Discontinued
0.7764	Intermediate Similarity	NPD1653	Approved
0.7742	Intermediate Similarity	NPD1551	Phase 2
0.7711	Intermediate Similarity	NPD3749	Approved
0.7702	Intermediate Similarity	NPD920	Approved
0.7684	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD3027	Phase 3
0.7667	Intermediate Similarity	NPD9494	Approved
0.7658	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7632	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6190	Approved
0.7607	Intermediate Similarity	NPD3226	Approved
0.7597	Intermediate Similarity	NPD1933	Approved
0.758	Intermediate Similarity	NPD2344	Approved
0.7578	Intermediate Similarity	NPD2534	Approved
0.7578	Intermediate Similarity	NPD2532	Approved
0.7578	Intermediate Similarity	NPD2533	Approved
0.7574	Intermediate Similarity	NPD7199	Phase 2
0.7564	Intermediate Similarity	NPD3748	Approved
0.756	Intermediate Similarity	NPD6234	Discontinued
0.7558	Intermediate Similarity	NPD3751	Discontinued
0.7548	Intermediate Similarity	NPD6651	Approved
0.7545	Intermediate Similarity	NPD7768	Phase 2
0.7517	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7516	Intermediate Similarity	NPD2313	Discontinued
0.75	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD1243	Approved
0.7484	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7469	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4628	Phase 3
0.7429	Intermediate Similarity	NPD5953	Discontinued
0.7427	Intermediate Similarity	NPD3787	Discontinued
0.7417	Intermediate Similarity	NPD1203	Approved
0.7416	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7414	Intermediate Similarity	NPD7286	Phase 2
0.7405	Intermediate Similarity	NPD6099	Approved
0.7405	Intermediate Similarity	NPD6100	Approved
0.7403	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD2309	Approved
0.7386	Intermediate Similarity	NPD7685	Pre-registration
0.7365	Intermediate Similarity	NPD37	Approved
0.7358	Intermediate Similarity	NPD2346	Discontinued
0.7347	Intermediate Similarity	NPD1548	Phase 1
0.7346	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7345	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD2799	Discontinued
0.7337	Intermediate Similarity	NPD4965	Approved
0.7337	Intermediate Similarity	NPD4967	Phase 2
0.7337	Intermediate Similarity	NPD4966	Approved
0.7333	Intermediate Similarity	NPD9269	Phase 2
0.7301	Intermediate Similarity	NPD7390	Discontinued
0.7273	Intermediate Similarity	NPD6832	Phase 2
0.7267	Intermediate Similarity	NPD422	Phase 1
0.7262	Intermediate Similarity	NPD6844	Discontinued
0.7261	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7257	Intermediate Similarity	NPD7228	Approved
0.7219	Intermediate Similarity	NPD9717	Approved
0.7208	Intermediate Similarity	NPD3018	Phase 2
0.7184	Intermediate Similarity	NPD5242	Approved
0.7182	Intermediate Similarity	NPD8434	Phase 2
0.7179	Intermediate Similarity	NPD3268	Approved
0.7161	Intermediate Similarity	NPD4908	Phase 1
0.7152	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7152	Intermediate Similarity	NPD1610	Phase 2
0.7152	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2403	Approved
0.7143	Intermediate Similarity	NPD2798	Approved
0.7134	Intermediate Similarity	NPD6233	Phase 2
0.7128	Intermediate Similarity	NPD6778	Approved
0.7128	Intermediate Similarity	NPD6780	Approved
0.7128	Intermediate Similarity	NPD6776	Approved
0.7128	Intermediate Similarity	NPD6782	Approved
0.7128	Intermediate Similarity	NPD6781	Approved
0.7128	Intermediate Similarity	NPD6777	Approved
0.7128	Intermediate Similarity	NPD6779	Approved
0.7125	Intermediate Similarity	NPD7033	Discontinued
0.7125	Intermediate Similarity	NPD4308	Phase 3
0.7124	Intermediate Similarity	NPD3225	Approved
0.7117	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD8313	Approved
0.7111	Intermediate Similarity	NPD8312	Approved
0.7105	Intermediate Similarity	NPD1608	Approved
0.7101	Intermediate Similarity	NPD6386	Approved
0.7101	Intermediate Similarity	NPD6385	Approved
0.7091	Intermediate Similarity	NPD4357	Discontinued
0.7078	Intermediate Similarity	NPD2797	Approved
0.7076	Intermediate Similarity	NPD5353	Approved
0.707	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD411	Approved
0.7067	Intermediate Similarity	NPD9268	Approved
0.7059	Intermediate Similarity	NPD2982	Phase 2
0.7059	Intermediate Similarity	NPD2983	Phase 2
0.7055	Intermediate Similarity	NPD2654	Approved
0.7047	Intermediate Similarity	NPD5536	Phase 2
0.7043	Intermediate Similarity	NPD4360	Phase 2
0.7043	Intermediate Similarity	NPD4363	Phase 3
0.7035	Intermediate Similarity	NPD2899	Discontinued
0.7029	Intermediate Similarity	NPD5710	Approved
0.7029	Intermediate Similarity	NPD5711	Approved
0.7016	Intermediate Similarity	NPD7435	Discontinued
0.7006	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD8150	Discontinued
0.6995	Remote Similarity	NPD7584	Approved
0.6993	Remote Similarity	NPD1481	Phase 2
0.6993	Remote Similarity	NPD2981	Phase 2
0.6987	Remote Similarity	NPD2861	Phase 2
0.6986	Remote Similarity	NPD228	Approved
0.6977	Remote Similarity	NPD4288	Approved
0.6968	Remote Similarity	NPD3266	Approved
0.6968	Remote Similarity	NPD1470	Approved
0.6968	Remote Similarity	NPD3267	Approved
0.6962	Remote Similarity	NPD6798	Discontinued
0.6961	Remote Similarity	NPD7549	Discontinued
0.6951	Remote Similarity	NPD1652	Phase 2
0.6949	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD7783	Phase 2
0.6933	Remote Similarity	NPD7266	Discontinued
0.6932	Remote Similarity	NPD7229	Phase 3
0.6928	Remote Similarity	NPD1535	Discovery
0.6928	Remote Similarity	NPD1201	Approved
0.6927	Remote Similarity	NPD7697	Approved
0.6927	Remote Similarity	NPD7698	Approved
0.6927	Remote Similarity	NPD7696	Phase 3
0.6923	Remote Similarity	NPD8151	Discontinued
0.6915	Remote Similarity	NPD4361	Phase 2
0.6915	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD17	Approved
0.6901	Remote Similarity	NPD7615	Clinical (unspecified phase)

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