NPASS Compound

Structure

CID170675 OpenBabel06191715542D 30 33 0 0 1 0 0 0 0 0999 V2000 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 4.5000 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 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 4.0000 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 3.4641 4.0000 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 4.3301 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 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 2 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 1.0000 0.0000 C 0 0 2 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 6.0622 4.5000 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 2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -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 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 0.8660 1.5000 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 2 2 0 0 0 0 1 7 1 0 0 0 0 2 9 1 0 0 0 0 3 6 2 0 0 0 0 3 8 1 0 0 0 0 4 6 1 0 0 0 0 4 10 2 0 0 0 0 5 20 1 0 0 0 0 6 21 1 0 0 0 0 7 18 2 0 0 0 0 7 22 1 0 0 0 0 8 12 2 0 0 0 0 8 23 1 0 0 0 0 9 13 2 0 0 0 0 9 29 1 0 0 0 0 10 12 1 0 0 0 0 10 28 1 0 0 0 0 11 5 1 6 0 0 0 11 14 1 0 0 0 0 11 30 1 0 0 0 0 12 15 1 0 0 0 0 13 15 1 0 0 0 0 13 18 1 0 0 0 0 14 16 1 0 0 0 0 14 24 1 1 0 0 0 15 25 2 0 0 0 0 16 17 1 0 0 0 0 16 26 1 6 0 0 0 17 19 1 0 0 0 0 17 27 1 1 0 0 0 18 28 1 0 0 0 0 19 29 1 6 0 0 0 19 30 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	422.08
Volume:	381.192
LogP:	0.075
LogD:	-0.032
LogS:	-3.705
# Rotatable Bonds:	3
TPSA:	190.28
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.263
Synthetic Accessibility Score:	4.032
Fsp3:	0.316
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.308
MDCK Permeability:	1.19350743261748e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.785
Human Intestinal Absorption (HIA):	0.628
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.027
Plasma Protein Binding (PPB):	84.64137268066406%
Volume Distribution (VD):	0.94
Pgp-substrate:	17.033201217651367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.262
CYP1A2-substrate:	0.076
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.056
CYP2C9-inhibitor:	0.029
CYP2C9-substrate:	0.498
CYP2D6-inhibitor:	0.105
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.039
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	2.995
Half-life (T1/2):	0.893

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.12
Drug-inuced Liver Injury (DILI):	0.977
AMES Toxicity:	0.829
Rat Oral Acute Toxicity:	0.021
Maximum Recommended Daily Dose:	0.004
Skin Sensitization:	0.718
Carcinogencity:	0.087
Eye Corrosion:	0.004
Eye Irritation:	0.344
Respiratory Toxicity:	0.034

Download Data

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

Natural Product: NPC170675

Natural Product ID:	NPC170675
*Common Name:**	Norswertianolin
IUPAC Name:	1,3,5-trihydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyxanthen-9-one
Synonyms:	Norswertianolin
Standard InCHIKey:	MYWLBRTZOYHDOU-FJMCMGCSSA-N
Standard InCHI:	InChI=1S/C19H18O11/c20-5-11-14(24)16(26)17(27)19(30-11)29-9-2-1-7(22)18-13(9)15(25)12-8(23)3-6(21)4-10(12)28-18/h1-4,11,14,16-17,19-24,26-27H,5H2/t11-,14-,16+,17-,19-/m1/s1
SMILES:	OC[C@H]1O[C@@H](Oc2ccc(c3c2c(=O)c2c(o3)cc(cc2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL512072
PubChem CID:	5281659
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones

*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
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858759]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16499318]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16562838]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[17524651]
NPO32688	gentianella amarella ssp. acuta	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18336006]
NPO28094	Consolida oliveriana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19489596]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20627740]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20718449]
NPO28996	Caloglossa leprieurii	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28586	Pyrus calleryana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28457	Siler trilobum	Species	Salticidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28996	Caloglossa leprieurii	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19861	Drypetes molunduana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28852	Euphorbia makinoi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28457	Siler trilobum	Species	Salticidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28149	Polygala fallax	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28586	Pyrus calleryana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28586	Pyrus calleryana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28532	Streptomyces gougerotii	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28149	Polygala fallax	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27923	Calophyllum apetalum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29129	Rhodiola heterodonta	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28020	Hypaphorus subumbrans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO28417	Monnina emarginata	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28502	Rhabdastrella globostellata	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28366	Cladonia furcata	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28252	Lophozia barbata	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19861	Drypetes molunduana	Species	Putranjivaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28852	Euphorbia makinoi	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28094	Consolida oliveriana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28586	Pyrus calleryana	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28996	Caloglossa leprieurii	Species	Delesseriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28457	Siler trilobum	Species	Salticidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28793	Wettsteinia inversa	Species	Adelanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20937	Heterocapsa niei	Species	Heterocapsaceae	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	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT204	Individual Protein	Acetylcholinesterase	Homo sapiens	Inhibition	=	4.4	%	PMID[492405]
NPT261	Individual Protein	Monoamine oxidase A	Homo sapiens	Inhibition	=	12.2	%	PMID[492405]
NPT582	Individual Protein	Monoamine oxidase B	Homo sapiens	Inhibition	=	28.9	%	PMID[492405]

☑ 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 NPC170675 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	471
0.1-0.2	1932
0.2-0.3	4467
0.3-0.4	10198
0.4-0.5	7767
0.5-0.6	4205
0.6-0.7	5280
0.7-0.8	5130
0.8-0.85	1431
0.85-0.9	1207
0.9-0.95	437
0.95-1	172

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC112755
1.0	High Similarity	NPC471457
0.9937	High Similarity	NPC22195
0.9937	High Similarity	NPC34287
0.9937	High Similarity	NPC471416
0.9937	High Similarity	NPC21190
0.9937	High Similarity	NPC183357
0.9874	High Similarity	NPC95855
0.9874	High Similarity	NPC472381
0.9874	High Similarity	NPC210042
0.9874	High Similarity	NPC472383
0.9814	High Similarity	NPC51774
0.9814	High Similarity	NPC239549
0.9814	High Similarity	NPC236191
0.9812	High Similarity	NPC474434
0.9812	High Similarity	NPC44558
0.9811	High Similarity	NPC58716
0.9811	High Similarity	NPC146792
0.9811	High Similarity	NPC45400
0.9811	High Similarity	NPC45618
0.9811	High Similarity	NPC93099
0.9752	High Similarity	NPC3583
0.9752	High Similarity	NPC205076
0.9752	High Similarity	NPC267254
0.9752	High Similarity	NPC259152
0.9752	High Similarity	NPC307518
0.9752	High Similarity	NPC301683
0.9752	High Similarity	NPC48773
0.9752	High Similarity	NPC472386
0.975	High Similarity	NPC105025
0.975	High Similarity	NPC93337
0.975	High Similarity	NPC183036
0.975	High Similarity	NPC45638
0.975	High Similarity	NPC469931
0.975	High Similarity	NPC475942
0.975	High Similarity	NPC201292
0.975	High Similarity	NPC58053
0.975	High Similarity	NPC229687
0.975	High Similarity	NPC226294
0.975	High Similarity	NPC186807
0.9748	High Similarity	NPC5778
0.9748	High Similarity	NPC236934
0.9747	High Similarity	NPC29830
0.9693	High Similarity	NPC268533
0.9691	High Similarity	NPC204693
0.9689	High Similarity	NPC224462
0.9689	High Similarity	NPC105511
0.9689	High Similarity	NPC84265
0.9689	High Similarity	NPC245014
0.9689	High Similarity	NPC282987
0.9686	High Similarity	NPC165720
0.9634	High Similarity	NPC476620
0.9634	High Similarity	NPC476623
0.9634	High Similarity	NPC476621
0.9634	High Similarity	NPC476622
0.9634	High Similarity	NPC476618
0.9634	High Similarity	NPC476619
0.9632	High Similarity	NPC142996
0.9632	High Similarity	NPC472607
0.9632	High Similarity	NPC102028
0.963	High Similarity	NPC172807
0.963	High Similarity	NPC117260
0.963	High Similarity	NPC476405
0.963	High Similarity	NPC254540
0.963	High Similarity	NPC211594
0.963	High Similarity	NPC156977
0.9625	High Similarity	NPC99957
0.9625	High Similarity	NPC181616
0.9623	High Similarity	NPC127415
0.9623	High Similarity	NPC270335
0.9623	High Similarity	NPC191306
0.9623	High Similarity	NPC88043
0.9573	High Similarity	NPC169733
0.9573	High Similarity	NPC472382
0.9573	High Similarity	NPC8573
0.9573	High Similarity	NPC472380
0.9573	High Similarity	NPC472384
0.9571	High Similarity	NPC45522
0.9571	High Similarity	NPC42773
0.9571	High Similarity	NPC101026
0.9571	High Similarity	NPC21666
0.9571	High Similarity	NPC24043
0.9571	High Similarity	NPC169977
0.9568	High Similarity	NPC51326
0.9568	High Similarity	NPC177731
0.9568	High Similarity	NPC231194
0.9568	High Similarity	NPC79056
0.9568	High Similarity	NPC293004
0.9568	High Similarity	NPC105095
0.9568	High Similarity	NPC44328
0.9565	High Similarity	NPC92565
0.9565	High Similarity	NPC135345
0.9565	High Similarity	NPC160156
0.9565	High Similarity	NPC477502
0.9565	High Similarity	NPC229729
0.9563	High Similarity	NPC311830
0.9563	High Similarity	NPC22832
0.956	High Similarity	NPC77660
0.956	High Similarity	NPC127782
0.956	High Similarity	NPC300537
0.956	High Similarity	NPC189142
0.9515	High Similarity	NPC472387
0.9515	High Similarity	NPC168584
0.9512	High Similarity	NPC477848
0.9512	High Similarity	NPC115760
0.9512	High Similarity	NPC237435
0.9512	High Similarity	NPC43211
0.9512	High Similarity	NPC49344
0.9512	High Similarity	NPC210094
0.9512	High Similarity	NPC135277
0.9512	High Similarity	NPC101191
0.9509	High Similarity	NPC475155
0.9509	High Similarity	NPC256760
0.9509	High Similarity	NPC261254
0.9506	High Similarity	NPC86008
0.9506	High Similarity	NPC293629
0.9506	High Similarity	NPC209296
0.9506	High Similarity	NPC43587
0.9506	High Similarity	NPC270578
0.9506	High Similarity	NPC52382
0.9506	High Similarity	NPC105283
0.9506	High Similarity	NPC195257
0.9503	High Similarity	NPC115674
0.9503	High Similarity	NPC21100
0.9503	High Similarity	NPC8856
0.9503	High Similarity	NPC197285
0.9503	High Similarity	NPC210073
0.95	High Similarity	NPC470178
0.95	High Similarity	NPC284960
0.95	High Similarity	NPC94777
0.95	High Similarity	NPC19709
0.95	High Similarity	NPC222936
0.95	High Similarity	NPC168822
0.95	High Similarity	NPC309025
0.95	High Similarity	NPC243930
0.95	High Similarity	NPC88023
0.9458	High Similarity	NPC470443
0.9458	High Similarity	NPC470444
0.9458	High Similarity	NPC110941
0.9458	High Similarity	NPC241423
0.9458	High Similarity	NPC473571
0.9458	High Similarity	NPC473682
0.9458	High Similarity	NPC126784
0.9455	High Similarity	NPC472991
0.9455	High Similarity	NPC233994
0.9455	High Similarity	NPC211532
0.9455	High Similarity	NPC472992
0.9455	High Similarity	NPC65563
0.9455	High Similarity	NPC472385
0.9455	High Similarity	NPC198324
0.9455	High Similarity	NPC470949
0.9451	High Similarity	NPC208668
0.9448	High Similarity	NPC150767
0.9448	High Similarity	NPC212748
0.9448	High Similarity	NPC204937
0.9448	High Similarity	NPC52353
0.9448	High Similarity	NPC194483
0.9448	High Similarity	NPC78734
0.9448	High Similarity	NPC149011
0.9448	High Similarity	NPC218488
0.9448	High Similarity	NPC285197
0.9444	High Similarity	NPC42892
0.9444	High Similarity	NPC116745
0.9441	High Similarity	NPC277205
0.9437	High Similarity	NPC473043
0.9405	High Similarity	NPC148710
0.9401	High Similarity	NPC473071
0.9401	High Similarity	NPC473073
0.9394	High Similarity	NPC264735
0.9394	High Similarity	NPC108202
0.939	High Similarity	NPC47140
0.939	High Similarity	NPC180918
0.939	High Similarity	NPC235575
0.939	High Similarity	NPC67134
0.939	High Similarity	NPC60735
0.939	High Similarity	NPC26230
0.9387	High Similarity	NPC203050
0.9387	High Similarity	NPC219904
0.9387	High Similarity	NPC61791
0.9387	High Similarity	NPC471287
0.9387	High Similarity	NPC225434
0.9387	High Similarity	NPC223747
0.9387	High Similarity	NPC120099
0.9383	High Similarity	NPC56077
0.9383	High Similarity	NPC118284
0.9383	High Similarity	NPC308404
0.9383	High Similarity	NPC88789
0.9383	High Similarity	NPC145038
0.9383	High Similarity	NPC281131
0.9383	High Similarity	NPC253662
0.9383	High Similarity	NPC274618
0.9383	High Similarity	NPC179950
0.9383	High Similarity	NPC70441
0.9383	High Similarity	NPC276222
0.9375	High Similarity	NPC182045
0.9345	High Similarity	NPC470446
0.9345	High Similarity	NPC470447
0.9345	High Similarity	NPC473072
0.9345	High Similarity	NPC470445
0.9345	High Similarity	NPC470449

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 NPC170675 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	430
0.1-0.2	953
0.2-0.3	2040
0.3-0.4	2701
0.4-0.5	1713
0.5-0.6	870
0.6-0.7	286
0.7-0.8	118
0.8-0.85	14
0.85-0.9	15
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9568	High Similarity	NPD7074	Phase 3
0.9512	High Similarity	NPD4338	Clinical (unspecified phase)
0.9506	High Similarity	NPD7054	Approved
0.9448	High Similarity	NPD7472	Approved
0.9444	High Similarity	NPD3818	Discontinued
0.9273	High Similarity	NPD6797	Phase 2
0.9217	High Similarity	NPD7251	Discontinued
0.9187	High Similarity	NPD4381	Clinical (unspecified phase)
0.9162	High Similarity	NPD7808	Phase 3
0.9085	High Similarity	NPD6167	Clinical (unspecified phase)
0.9085	High Similarity	NPD6166	Phase 2
0.9085	High Similarity	NPD6168	Clinical (unspecified phase)
0.9057	High Similarity	NPD1934	Approved
0.9	High Similarity	NPD2801	Approved
0.8882	High Similarity	NPD2393	Clinical (unspecified phase)
0.881	High Similarity	NPD7804	Clinical (unspecified phase)
0.8773	High Similarity	NPD4868	Clinical (unspecified phase)
0.8614	High Similarity	NPD5494	Approved
0.858	High Similarity	NPD4380	Phase 2
0.8553	High Similarity	NPD1511	Approved
0.8545	High Similarity	NPD3882	Suspended
0.8488	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD3817	Phase 2
0.8447	Intermediate Similarity	NPD1512	Approved
0.8439	Intermediate Similarity	NPD6559	Discontinued
0.8373	Intermediate Similarity	NPD5402	Approved
0.8344	Intermediate Similarity	NPD1653	Approved
0.8313	Intermediate Similarity	NPD1465	Phase 2
0.8291	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8274	Intermediate Similarity	NPD7075	Discontinued
0.8266	Intermediate Similarity	NPD5844	Phase 1
0.8239	Intermediate Similarity	NPD1549	Phase 2
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD7228	Approved
0.8095	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8081	Intermediate Similarity	NPD6232	Discontinued
0.8049	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8047	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD7473	Discontinued
0.8036	Intermediate Similarity	NPD6801	Discontinued
0.8034	Intermediate Similarity	NPD8313	Approved
0.8034	Intermediate Similarity	NPD8312	Approved
0.8023	Intermediate Similarity	NPD6959	Discontinued
0.8011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3751	Discontinued
0.7988	Intermediate Similarity	NPD7819	Suspended
0.7977	Intermediate Similarity	NPD3787	Discontinued
0.7976	Intermediate Similarity	NPD7411	Suspended
0.7952	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD5403	Approved
0.7937	Intermediate Similarity	NPD1510	Phase 2
0.7921	Intermediate Similarity	NPD7685	Pre-registration
0.7919	Intermediate Similarity	NPD7199	Phase 2
0.7911	Intermediate Similarity	NPD1613	Approved
0.7911	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD6234	Discontinued
0.7888	Intermediate Similarity	NPD2796	Approved
0.7879	Intermediate Similarity	NPD6799	Approved
0.7845	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7831	Intermediate Similarity	NPD5401	Approved
0.7824	Intermediate Similarity	NPD37	Approved
0.7819	Intermediate Similarity	NPD6780	Approved
0.7819	Intermediate Similarity	NPD6779	Approved
0.7819	Intermediate Similarity	NPD6781	Approved
0.7819	Intermediate Similarity	NPD6777	Approved
0.7819	Intermediate Similarity	NPD6778	Approved
0.7819	Intermediate Similarity	NPD6776	Approved
0.7819	Intermediate Similarity	NPD6782	Approved
0.7799	Intermediate Similarity	NPD943	Approved
0.7791	Intermediate Similarity	NPD4966	Approved
0.7791	Intermediate Similarity	NPD4965	Approved
0.7791	Intermediate Similarity	NPD4967	Phase 2
0.773	Intermediate Similarity	NPD7266	Discontinued
0.7727	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD1247	Approved
0.7706	Intermediate Similarity	NPD6599	Discontinued
0.7696	Intermediate Similarity	NPD7698	Approved
0.7696	Intermediate Similarity	NPD7696	Phase 3
0.7696	Intermediate Similarity	NPD7435	Discontinued
0.7696	Intermediate Similarity	NPD7697	Approved
0.7692	Intermediate Similarity	NPD7783	Phase 2
0.7692	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD1240	Approved
0.7684	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD8151	Discontinued
0.7674	Intermediate Similarity	NPD8455	Phase 2
0.7665	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7658	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6190	Approved
0.7644	Intermediate Similarity	NPD3749	Approved
0.7629	Intermediate Similarity	NPD7701	Phase 2
0.7627	Intermediate Similarity	NPD3926	Phase 2
0.7624	Intermediate Similarity	NPD7240	Approved
0.761	Intermediate Similarity	NPD3027	Phase 3
0.7595	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD1607	Approved
0.759	Intermediate Similarity	NPD3750	Approved
0.759	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7577	Intermediate Similarity	NPD7584	Approved
0.7565	Intermediate Similarity	NPD7870	Phase 2
0.7565	Intermediate Similarity	NPD7871	Phase 2
0.7561	Intermediate Similarity	NPD2935	Discontinued
0.7553	Intermediate Similarity	NPD6535	Approved
0.7553	Intermediate Similarity	NPD6534	Approved
0.7552	Intermediate Similarity	NPD6823	Phase 2
0.7531	Intermediate Similarity	NPD230	Phase 1
0.7531	Intermediate Similarity	NPD1933	Approved
0.7526	Intermediate Similarity	NPD7699	Phase 2
0.7526	Intermediate Similarity	NPD7700	Phase 2
0.75	Intermediate Similarity	NPD919	Approved
0.7486	Intermediate Similarity	NPD7768	Phase 2
0.7485	Intermediate Similarity	NPD4628	Phase 3
0.747	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD1551	Phase 2
0.7424	Intermediate Similarity	NPD7801	Approved
0.7423	Intermediate Similarity	NPD447	Suspended
0.7412	Intermediate Similarity	NPD2532	Approved
0.7412	Intermediate Similarity	NPD2534	Approved
0.7412	Intermediate Similarity	NPD2533	Approved
0.7358	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7321	Intermediate Similarity	NPD2800	Approved
0.7316	Intermediate Similarity	NPD6212	Phase 3
0.7316	Intermediate Similarity	NPD6213	Phase 3
0.7316	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD3748	Approved
0.7283	Intermediate Similarity	NPD5953	Discontinued
0.7245	Intermediate Similarity	NPD7680	Approved
0.7241	Intermediate Similarity	NPD3226	Approved
0.7234	Intermediate Similarity	NPD8150	Discontinued
0.7234	Intermediate Similarity	NPD8434	Phase 2
0.7225	Intermediate Similarity	NPD920	Approved
0.7219	Intermediate Similarity	NPD6674	Discontinued
0.7216	Intermediate Similarity	NPD6844	Discontinued
0.7215	Intermediate Similarity	NPD1091	Approved
0.7209	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7208	Intermediate Similarity	NPD8320	Phase 1
0.7208	Intermediate Similarity	NPD8319	Approved
0.7202	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7585	Approved
0.7174	Intermediate Similarity	NPD7286	Phase 2
0.716	Intermediate Similarity	NPD9494	Approved
0.7143	Intermediate Similarity	NPD6099	Approved
0.7143	Intermediate Similarity	NPD7458	Discontinued
0.7143	Intermediate Similarity	NPD6100	Approved
0.7136	Intermediate Similarity	NPD7583	Approved
0.7134	Intermediate Similarity	NPD2313	Discontinued
0.7117	Intermediate Similarity	NPD4908	Phase 1
0.7112	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2346	Discontinued
0.7101	Intermediate Similarity	NPD2344	Approved
0.7098	Intermediate Similarity	NPD4363	Phase 3
0.7098	Intermediate Similarity	NPD4360	Phase 2
0.7093	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2799	Discontinued
0.7083	Intermediate Similarity	NPD7033	Discontinued
0.7066	Intermediate Similarity	NPD6651	Approved
0.7055	Intermediate Similarity	NPD2861	Phase 2
0.7052	Intermediate Similarity	NPD7390	Discontinued
0.7049	Intermediate Similarity	NPD5242	Approved
0.7045	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5353	Approved
0.7037	Intermediate Similarity	NPD1203	Approved
0.7033	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD5006	Approved
0.702	Intermediate Similarity	NPD5005	Approved
0.7019	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7018	Intermediate Similarity	NPD1243	Approved
0.7012	Intermediate Similarity	NPD6832	Phase 2
0.7011	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD7211	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD1610	Phase 2
0.6995	Remote Similarity	NPD5710	Approved
0.6995	Remote Similarity	NPD5711	Approved
0.6994	Remote Similarity	NPD2798	Approved
0.6988	Remote Similarity	NPD6233	Phase 2
0.6982	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD9269	Phase 2
0.6947	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.694	Remote Similarity	NPD8127	Discontinued
0.6936	Remote Similarity	NPD2309	Approved
0.6934	Remote Similarity	NPD8059	Phase 3
0.6934	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7549	Discontinued
0.6928	Remote Similarity	NPD6798	Discontinued
0.6927	Remote Similarity	NPD6841	Approved
0.6927	Remote Similarity	NPD6843	Phase 3

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