NPASS Compound

Structure

CID250557 OpenBabel06191716052D 26 28 0 0 0 0 0 0 0 0999 V2000 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 -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 -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 -4.3301 0.5000 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 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 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 -6.0622 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 -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 -6.0622 1.5000 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 -5.1962 3.0000 0.0000 O 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 -2.5981 1.5000 0.0000 O 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 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 23 1 0 0 0 0 2 24 1 0 0 0 0 3 25 1 0 0 0 0 4 8 2 0 0 0 0 4 10 1 0 0 0 0 5 8 1 0 0 0 0 5 13 2 0 0 0 0 6 11 2 0 0 0 0 6 12 1 0 0 0 0 7 9 2 0 0 0 0 7 26 1 0 0 0 0 8 9 1 0 0 0 0 9 15 1 0 0 0 0 10 17 2 0 0 0 0 10 19 1 0 0 0 0 11 18 1 0 0 0 0 11 20 1 0 0 0 0 12 14 2 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 21 2 0 0 0 0 16 18 2 0 0 0 0 16 22 1 0 0 0 0 17 24 1 0 0 0 0 18 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	360.08
Volume:	343.445
LogP:	2.306
LogD:	2.37
LogS:	-3.602
# Rotatable Bonds:	4
TPSA:	118.59
# H-Bond Aceptor:	8
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	8

MedChem Properties

QED Drug-Likeness Score:	0.65
Synthetic Accessibility Score:	2.673
Fsp3:	0.167
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.041
MDCK Permeability:	1.2919512300868519e-05
Pgp-inhibitor:	0.399
Pgp-substrate:	0.112
Human Intestinal Absorption (HIA):	0.042
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.005
Plasma Protein Binding (PPB):	90.61128997802734%
Volume Distribution (VD):	0.64
Pgp-substrate:	16.74368667602539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.782
CYP1A2-substrate:	0.96
CYP2C19-inhibitor:	0.125
CYP2C19-substrate:	0.064
CYP2C9-inhibitor:	0.689
CYP2C9-substrate:	0.778
CYP2D6-inhibitor:	0.536
CYP2D6-substrate:	0.407
CYP3A4-inhibitor:	0.447
CYP3A4-substrate:	0.168

ADMET: Excretion

Clearance (CL):	4.316
Half-life (T1/2):	0.843

ADMET: Toxicity

hERG Blockers:	0.18
Human Hepatotoxicity (H-HT):	0.084
Drug-inuced Liver Injury (DILI):	0.437
AMES Toxicity:	0.092
Rat Oral Acute Toxicity:	0.259
Maximum Recommended Daily Dose:	0.145
Skin Sensitization:	0.921
Carcinogencity:	0.033
Eye Corrosion:	0.006
Eye Irritation:	0.888
Respiratory Toxicity:	0.197

Download Data

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

Natural Product: NPC250557

Natural Product ID:	NPC250557
*Common Name:**	Irigenin
IUPAC Name:	5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxychromen-4-one
Synonyms:	Irigenin
Standard InCHIKey:	TUGWPJJTQNLKCL-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3
SMILES:	COc1cc(cc(c1OC)O)c1coc2c(c1=O)c(O)c(c(c2)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487013
PubChem CID:	5464170
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0003651] 3'-hydroxy,4'-methoxyisoflavonoids

*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
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075762]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	rhizomes	Thai	n.a.	PMID[15787436]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21465599]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[22388969]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24433009]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25036154]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[25204177]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28032759]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31246464]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917289]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13012	Iris dichotoma	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13012	Iris dichotoma	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2781	Iris kumaonensis	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7478	Iris germanica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13012	Iris dichotoma	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30734	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1278	Eriocaulon sieboldianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21346	Eriocaulon buergerianum	Species	Eriocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7528	Belamcanda chinensis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2566	0cardiopsaceae	Species	0cardiopsaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2781	Iris kumaonensis	Species	Tarachodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6516	Aspidosperma megalocarpon	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14417	Iris tectorum	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO942	Perophora namei	Species	Perophoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5561	Thenea muricata	Species	Theneidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3733	Senecio triangularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13012	Iris dichotoma	Species	Iridaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual Protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	0.0	%	PMID[489295]

☑ 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 NPC250557 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	465
0.1-0.2	1997
0.2-0.3	4877
0.3-0.4	11382
0.4-0.5	6156
0.5-0.6	3883
0.6-0.7	5108
0.7-0.8	4969
0.8-0.85	1976
0.85-0.9	1132
0.9-0.95	639
0.95-1	113

Similarity Score	Similarity Level	Natural Product ID
0.9864	High Similarity	NPC124714
0.9863	High Similarity	NPC45291
0.9863	High Similarity	NPC19980
0.9799	High Similarity	NPC78103
0.9797	High Similarity	NPC130589
0.9797	High Similarity	NPC134287
0.9796	High Similarity	NPC291802
0.9796	High Similarity	NPC209487
0.9796	High Similarity	NPC216769
0.9796	High Similarity	NPC245382
0.9796	High Similarity	NPC269451
0.9796	High Similarity	NPC100971
0.9796	High Similarity	NPC100263
0.9796	High Similarity	NPC131266
0.9796	High Similarity	NPC35763
0.9796	High Similarity	NPC121522
0.9796	High Similarity	NPC181209
0.9795	High Similarity	NPC239363
0.9728	High Similarity	NPC262623
0.9664	High Similarity	NPC208197
0.9664	High Similarity	NPC39184
0.966	High Similarity	NPC10467
0.966	High Similarity	NPC156953
0.9597	High Similarity	NPC250822
0.9597	High Similarity	NPC75279
0.9597	High Similarity	NPC280937
0.9597	High Similarity	NPC276409
0.9592	High Similarity	NPC333691
0.9592	High Similarity	NPC142876
0.9592	High Similarity	NPC69430
0.9592	High Similarity	NPC200060
0.9592	High Similarity	NPC92722
0.9592	High Similarity	NPC139293
0.9592	High Similarity	NPC102003
0.9592	High Similarity	NPC264550
0.9592	High Similarity	NPC264289
0.9592	High Similarity	NPC40290
0.9592	High Similarity	NPC195763
0.9533	High Similarity	NPC20830
0.9533	High Similarity	NPC183597
0.9533	High Similarity	NPC128863
0.9533	High Similarity	NPC227325
0.9533	High Similarity	NPC201136
0.9533	High Similarity	NPC256612
0.9533	High Similarity	NPC213622
0.9533	High Similarity	NPC196439
0.9533	High Similarity	NPC167815
0.9533	High Similarity	NPC146165
0.9533	High Similarity	NPC2476
0.9533	High Similarity	NPC92659
0.9533	High Similarity	NPC138360
0.9533	High Similarity	NPC280339
0.9533	High Similarity	NPC4455
0.9533	High Similarity	NPC163780
0.9533	High Similarity	NPC50715
0.9524	High Similarity	NPC80710
0.9524	High Similarity	NPC131451
0.9524	High Similarity	NPC194653
0.9524	High Similarity	NPC287395
0.9524	High Similarity	NPC183655
0.9524	High Similarity	NPC15329
0.9524	High Similarity	NPC203747
0.9524	High Similarity	NPC139364
0.9524	High Similarity	NPC254702
0.9524	High Similarity	NPC218490
0.947	High Similarity	NPC472916
0.947	High Similarity	NPC474520
0.9467	High Similarity	NPC47781
0.9467	High Similarity	NPC22519
0.9467	High Similarity	NPC176775
0.9467	High Similarity	NPC160951
0.9467	High Similarity	NPC274327
0.9467	High Similarity	NPC255350
0.9467	High Similarity	NPC145379
0.9467	High Similarity	NPC69394
0.9467	High Similarity	NPC183878
0.9467	High Similarity	NPC231018
0.9463	High Similarity	NPC256406
0.9456	High Similarity	NPC93034
0.9456	High Similarity	NPC188074
0.9456	High Similarity	NPC125449
0.9456	High Similarity	NPC119660
0.9416	High Similarity	NPC81679
0.9412	High Similarity	NPC476980
0.9408	High Similarity	NPC156057
0.9408	High Similarity	NPC93376
0.9408	High Similarity	NPC78302
0.9408	High Similarity	NPC162869
0.9408	High Similarity	NPC189179
0.9408	High Similarity	NPC245758
0.9408	High Similarity	NPC75215
0.9408	High Similarity	NPC235215
0.9408	High Similarity	NPC472911
0.9408	High Similarity	NPC472438
0.9408	High Similarity	NPC474208
0.9408	High Similarity	NPC36852
0.9408	High Similarity	NPC475267
0.9408	High Similarity	NPC210084
0.9408	High Similarity	NPC7973
0.9408	High Similarity	NPC474836
0.9408	High Similarity	NPC29841
0.9408	High Similarity	NPC99597
0.9408	High Similarity	NPC472910
0.9408	High Similarity	NPC469584
0.9408	High Similarity	NPC222814
0.9408	High Similarity	NPC262286
0.9408	High Similarity	NPC472913
0.9408	High Similarity	NPC48208
0.9408	High Similarity	NPC472914
0.9408	High Similarity	NPC470402
0.9408	High Similarity	NPC224137
0.9408	High Similarity	NPC227192
0.9408	High Similarity	NPC96167
0.9404	High Similarity	NPC2928
0.94	High Similarity	NPC156222
0.94	High Similarity	NPC275836
0.94	High Similarity	NPC162313
0.94	High Similarity	NPC241498
0.94	High Similarity	NPC100887
0.94	High Similarity	NPC198826
0.94	High Similarity	NPC120163
0.94	High Similarity	NPC239128
0.94	High Similarity	NPC187498
0.94	High Similarity	NPC293183
0.94	High Similarity	NPC60972
0.94	High Similarity	NPC71334
0.94	High Similarity	NPC131624
0.94	High Similarity	NPC301323
0.94	High Similarity	NPC101996
0.94	High Similarity	NPC188203
0.94	High Similarity	NPC83508
0.94	High Similarity	NPC39732
0.94	High Similarity	NPC222830
0.94	High Similarity	NPC25270
0.94	High Similarity	NPC212678
0.94	High Similarity	NPC57030
0.94	High Similarity	NPC142540
0.94	High Similarity	NPC275722
0.94	High Similarity	NPC256283
0.9392	High Similarity	NPC166036
0.9392	High Similarity	NPC203077
0.9392	High Similarity	NPC238279
0.9388	High Similarity	NPC12377
0.9388	High Similarity	NPC216314
0.9388	High Similarity	NPC226987
0.9388	High Similarity	NPC165389
0.9388	High Similarity	NPC120924
0.9388	High Similarity	NPC195919
0.9388	High Similarity	NPC143903
0.9384	High Similarity	NPC182842
0.9355	High Similarity	NPC470459
0.9351	High Similarity	NPC266314
0.9351	High Similarity	NPC258331
0.9351	High Similarity	NPC260640
0.9351	High Similarity	NPC295009
0.9346	High Similarity	NPC143828
0.9346	High Similarity	NPC130894
0.9346	High Similarity	NPC18772
0.9346	High Similarity	NPC176300
0.9346	High Similarity	NPC253634
0.9346	High Similarity	NPC7846
0.9346	High Similarity	NPC300943
0.9346	High Similarity	NPC288669
0.9346	High Similarity	NPC193842
0.9346	High Similarity	NPC9609
0.9346	High Similarity	NPC115798
0.9346	High Similarity	NPC25495
0.9346	High Similarity	NPC261004
0.9346	High Similarity	NPC19687
0.9346	High Similarity	NPC204854
0.9346	High Similarity	NPC18607
0.9346	High Similarity	NPC191459
0.9346	High Similarity	NPC105242
0.9346	High Similarity	NPC4481
0.9346	High Similarity	NPC152166
0.9346	High Similarity	NPC22472
0.9342	High Similarity	NPC138243
0.9342	High Similarity	NPC235165
0.9342	High Similarity	NPC247017
0.9342	High Similarity	NPC100916
0.9342	High Similarity	NPC255106
0.9342	High Similarity	NPC200388
0.9342	High Similarity	NPC98661
0.9342	High Similarity	NPC55619
0.9342	High Similarity	NPC268161
0.9342	High Similarity	NPC49824
0.9338	High Similarity	NPC88645
0.9338	High Similarity	NPC167091
0.9338	High Similarity	NPC206238
0.9338	High Similarity	NPC271779
0.9338	High Similarity	NPC472915
0.9338	High Similarity	NPC292214
0.9333	High Similarity	NPC171010
0.9333	High Similarity	NPC308451
0.9333	High Similarity	NPC208043
0.9333	High Similarity	NPC226973
0.9329	High Similarity	NPC48479
0.9329	High Similarity	NPC38545
0.9329	High Similarity	NPC171916
0.9329	High Similarity	NPC328119

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 NPC250557 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	1007
0.2-0.3	1977
0.3-0.4	2627
0.4-0.5	1706
0.5-0.6	912
0.6-0.7	325
0.7-0.8	115
0.8-0.85	23
0.85-0.9	17
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9467	High Similarity	NPD2801	Approved
0.9145	High Similarity	NPD1934	Approved
0.8968	High Similarity	NPD3882	Suspended
0.8961	High Similarity	NPD2393	Clinical (unspecified phase)
0.8938	High Similarity	NPD3818	Discontinued
0.8867	High Similarity	NPD1511	Approved
0.8812	High Similarity	NPD6167	Clinical (unspecified phase)
0.8812	High Similarity	NPD6166	Phase 2
0.8812	High Similarity	NPD6168	Clinical (unspecified phase)
0.8782	High Similarity	NPD3817	Phase 2
0.8766	High Similarity	NPD4380	Phase 2
0.875	High Similarity	NPD1512	Approved
0.8726	High Similarity	NPD4868	Clinical (unspecified phase)
0.8707	High Similarity	NPD1510	Phase 2
0.8667	High Similarity	NPD4338	Clinical (unspecified phase)
0.865	High Similarity	NPD7054	Approved
0.8598	High Similarity	NPD7472	Approved
0.8598	High Similarity	NPD7074	Phase 3
0.8571	High Similarity	NPD6232	Discontinued
0.8562	High Similarity	NPD5494	Approved
0.8528	High Similarity	NPD7473	Discontinued
0.8442	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8435	Intermediate Similarity	NPD943	Approved
0.8435	Intermediate Similarity	NPD1240	Approved
0.8434	Intermediate Similarity	NPD6797	Phase 2
0.8383	Intermediate Similarity	NPD7251	Discontinued
0.8333	Intermediate Similarity	NPD7808	Phase 3
0.8323	Intermediate Similarity	NPD7075	Discontinued
0.8322	Intermediate Similarity	NPD1607	Approved
0.8313	Intermediate Similarity	NPD5402	Approved
0.8289	Intermediate Similarity	NPD1549	Phase 2
0.8278	Intermediate Similarity	NPD2796	Approved
0.825	Intermediate Similarity	NPD1465	Phase 2
0.8224	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8205	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD6801	Discontinued
0.8171	Intermediate Similarity	NPD1247	Approved
0.8158	Intermediate Similarity	NPD2935	Discontinued
0.8141	Intermediate Similarity	NPD6799	Approved
0.8137	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8137	Intermediate Similarity	NPD7819	Suspended
0.8133	Intermediate Similarity	NPD230	Phase 1
0.8101	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.8095	Intermediate Similarity	NPD5844	Phase 1
0.8052	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD7411	Suspended
0.7988	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD3027	Phase 3
0.7975	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7964	Intermediate Similarity	NPD3926	Phase 2
0.7952	Intermediate Similarity	NPD6959	Discontinued
0.795	Intermediate Similarity	NPD6599	Discontinued
0.7943	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD5403	Approved
0.7862	Intermediate Similarity	NPD2532	Approved
0.7862	Intermediate Similarity	NPD2534	Approved
0.7862	Intermediate Similarity	NPD2533	Approved
0.7857	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD9494	Approved
0.7849	Intermediate Similarity	NPD6559	Discontinued
0.7834	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD6234	Discontinued
0.7831	Intermediate Similarity	NPD919	Approved
0.7785	Intermediate Similarity	NPD6190	Approved
0.775	Intermediate Similarity	NPD5401	Approved
0.7744	Intermediate Similarity	NPD37	Approved
0.7742	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7733	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD6651	Approved
0.7722	Intermediate Similarity	NPD3750	Approved
0.7716	Intermediate Similarity	NPD1653	Approved
0.7712	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD1613	Approved
0.7706	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7682	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.767	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD447	Suspended
0.7658	Intermediate Similarity	NPD2800	Approved
0.7654	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD4967	Phase 2
0.7605	Intermediate Similarity	NPD4965	Approved
0.7605	Intermediate Similarity	NPD7768	Phase 2
0.7605	Intermediate Similarity	NPD4966	Approved
0.758	Intermediate Similarity	NPD1551	Phase 2
0.7578	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7578	Intermediate Similarity	NPD7390	Discontinued
0.756	Intermediate Similarity	NPD3749	Approved
0.7554	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7546	Intermediate Similarity	NPD920	Approved
0.7543	Intermediate Similarity	NPD7685	Pre-registration
0.7531	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD7199	Phase 2
0.7517	Intermediate Similarity	NPD9269	Phase 2
0.7514	Intermediate Similarity	NPD7228	Approved
0.75	Intermediate Similarity	NPD4628	Phase 3
0.7486	Intermediate Similarity	NPD5953	Discontinued
0.7468	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD3226	Approved
0.7442	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5242	Approved
0.7438	Intermediate Similarity	NPD1243	Approved
0.7434	Intermediate Similarity	NPD2798	Approved
0.7423	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7421	Intermediate Similarity	NPD2344	Approved
0.7414	Intermediate Similarity	NPD3751	Discontinued
0.7405	Intermediate Similarity	NPD3748	Approved
0.7371	Intermediate Similarity	NPD7286	Phase 2
0.7366	Intermediate Similarity	NPD6777	Approved
0.7366	Intermediate Similarity	NPD6780	Approved
0.7366	Intermediate Similarity	NPD6778	Approved
0.7366	Intermediate Similarity	NPD6776	Approved
0.7366	Intermediate Similarity	NPD6781	Approved
0.7366	Intermediate Similarity	NPD6782	Approved
0.7366	Intermediate Similarity	NPD6779	Approved
0.7358	Intermediate Similarity	NPD6100	Approved
0.7358	Intermediate Similarity	NPD6099	Approved
0.7355	Intermediate Similarity	NPD2313	Discontinued
0.7337	Intermediate Similarity	NPD5353	Approved
0.7325	Intermediate Similarity	NPD1933	Approved
0.7303	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD2799	Discontinued
0.7283	Intermediate Similarity	NPD3787	Discontinued
0.7283	Intermediate Similarity	NPD5710	Approved
0.7283	Intermediate Similarity	NPD5711	Approved
0.7273	Intermediate Similarity	NPD3018	Phase 2
0.7262	Intermediate Similarity	NPD6385	Approved
0.7262	Intermediate Similarity	NPD6386	Approved
0.7256	Intermediate Similarity	NPD4357	Discontinued
0.7249	Intermediate Similarity	NPD7435	Discontinued
0.7248	Intermediate Similarity	NPD9268	Approved
0.724	Intermediate Similarity	NPD8151	Discontinued
0.7239	Intermediate Similarity	NPD2309	Approved
0.7238	Intermediate Similarity	NPD8150	Discontinued
0.7238	Intermediate Similarity	NPD8434	Phase 2
0.723	Intermediate Similarity	NPD5536	Phase 2
0.7226	Intermediate Similarity	NPD6832	Phase 2
0.7222	Intermediate Similarity	NPD2654	Approved
0.7219	Intermediate Similarity	NPD6844	Discontinued
0.7205	Intermediate Similarity	NPD2346	Discontinued
0.7204	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD2899	Discontinued
0.7167	Intermediate Similarity	NPD8313	Approved
0.7167	Intermediate Similarity	NPD8312	Approved
0.7158	Intermediate Similarity	NPD7698	Approved
0.7158	Intermediate Similarity	NPD7697	Approved
0.7158	Intermediate Similarity	NPD7696	Phase 3
0.7143	Intermediate Similarity	NPD1470	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD1203	Approved
0.7124	Intermediate Similarity	NPD2983	Phase 2
0.7124	Intermediate Similarity	NPD2982	Phase 2
0.712	Intermediate Similarity	NPD7870	Phase 2
0.712	Intermediate Similarity	NPD7871	Phase 2
0.7115	Intermediate Similarity	NPD4908	Phase 1
0.7107	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD6823	Phase 2
0.7099	Intermediate Similarity	NPD7266	Discontinued
0.7098	Intermediate Similarity	NPD7701	Phase 2
0.7097	Intermediate Similarity	NPD6534	Approved
0.7097	Intermediate Similarity	NPD6535	Approved
0.7081	Intermediate Similarity	NPD7033	Discontinued
0.7067	Intermediate Similarity	NPD1548	Phase 1
0.7059	Intermediate Similarity	NPD3972	Approved
0.7059	Intermediate Similarity	NPD2981	Phase 2
0.7056	Intermediate Similarity	NPD7240	Approved
0.7047	Intermediate Similarity	NPD7584	Approved
0.7026	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7874	Approved
0.7025	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD3268	Approved
0.7017	Intermediate Similarity	NPD7549	Discontinued
0.7006	Intermediate Similarity	NPD2403	Approved
0.7005	Intermediate Similarity	NPD4363	Phase 3
0.7005	Intermediate Similarity	NPD4360	Phase 2
0.6993	Remote Similarity	NPD1610	Phase 2
0.6993	Remote Similarity	NPD1201	Approved
0.699	Remote Similarity	NPD7801	Approved
0.6984	Remote Similarity	NPD7699	Phase 2
0.6984	Remote Similarity	NPD7700	Phase 2
0.6981	Remote Similarity	NPD6233	Phase 2
0.6975	Remote Similarity	NPD4308	Phase 3
0.6954	Remote Similarity	NPD9545	Approved
0.6948	Remote Similarity	NPD9717	Approved
0.6943	Remote Similarity	NPD2861	Phase 2
0.694	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD228	Approved
0.6933	Remote Similarity	NPD5408	Approved
0.6933	Remote Similarity	NPD5405	Approved
0.6933	Remote Similarity	NPD5406	Approved
0.6933	Remote Similarity	NPD9493	Approved
0.6933	Remote Similarity	NPD5404	Approved
0.6923	Remote Similarity	NPD2797	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