NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	244.11
Volume:	261.435
LogP:	4.314
LogD:	3.013
LogS:	-3.342
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.671
Synthetic Accessibility Score:	2.856
Fsp3:	0.2
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.996
MDCK Permeability:	1.1480299690447282e-05
Pgp-inhibitor:	0.007
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.955
30% Bioavailability (F30%):	0.968

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.017
Plasma Protein Binding (PPB):	97.54660034179688%
Volume Distribution (VD):	0.56
Pgp-substrate:	4.405355930328369%

ADMET: Metabolism

CYP1A2-inhibitor:	0.96
CYP1A2-substrate:	0.88
CYP2C19-inhibitor:	0.122
CYP2C19-substrate:	0.1
CYP2C9-inhibitor:	0.535
CYP2C9-substrate:	0.538
CYP2D6-inhibitor:	0.622
CYP2D6-substrate:	0.394
CYP3A4-inhibitor:	0.184
CYP3A4-substrate:	0.163

ADMET: Excretion

Clearance (CL):	13.189
Half-life (T1/2):	0.651

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.033
Drug-inuced Liver Injury (DILI):	0.903
AMES Toxicity:	0.586
Rat Oral Acute Toxicity:	0.655
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.952
Carcinogencity:	0.348
Eye Corrosion:	0.052
Eye Irritation:	0.953
Respiratory Toxicity:	0.785

Download Data

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

Natural Product: NPC282577

Natural Product ID:	NPC282577
*Common Name:**	Mansonone G
IUPAC Name:	6-hydroxy-3,8-dimethyl-5-propan-2-ylnaphthalene-1,2-dione
Synonyms:	Mansonone G
Standard InCHIKey:	KAIIHLMDZDKJOC-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O3/c1-7(2)12-10-5-9(4)14(17)15(18)13(10)8(3)6-11(12)16/h5-7,16H,1-4H3
SMILES:	O=C1C(=Cc2c(C1=O)c(C)cc(c2C(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2206793
PubChem CID:	608583
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/np020518b]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	root bark	Kuantaochi, Nantou Hsien, Taiwan	n.a.	PMID[10924160]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	stem bark;fruit	n.a.	n.a.	PMID[10924160]
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762814]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679307]
NPO3895	Gynerium sagittatum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17442349]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	Australian rainforest	n.a.	PMID[18039010]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20218657]
NPO32770	sterculia tavia	Species	Malvaceae	Eukaryota	n.a.	Madagascar Rain Forest	n.a.	PMID[23149304]
NPO7073	Prorocentrum maculosum	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8946740]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25170	Dictyota coriacea	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8878	Polygala arenaria	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11354	Streptomyces galbus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6423	Vitex cauliflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13058	Psychotria brachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4583	Agathosma gnidioides	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11158	Diplopterygium rufopilosum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25170	Dictyota coriacea	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9794	Dysoxylum fraseranum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2181	Erodium chium	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7535	Mansonia altissima	Species	Culicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24924	Saara hardwickii	Species	Agamidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5758	Licania crassifolia	Species	Chrysobalanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6878	Vesperus xatarti	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7073	Prorocentrum maculosum	Species	Prorocentraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3895	Gynerium sagittatum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11510	Astragalus flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7216	Helicteres angustifolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10273	Dictyota flabellata	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12123	Geodia gigas	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4348	Watasenia scintillans	Species	Enoploteuthidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8699	Azanza garckeana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO329	Arum cucullatum	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9565	Linum maritimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3118	Murraya euchrestifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1732	Ligularia franchetiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17202	Lasallia asiae-orientalis	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4060	Carduus assoi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3546	Shorea balangeran	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2124	Bulgaria inquinans	Species	Bulgariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25866	Kaunia lasiophthalma	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2066	Streptomyces ipomoeae	Species	Streptomycetaceae	Bacteria	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
MIC	5
Others	6

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	10
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	=	10200.0	nM	PMID[459549]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	64.36	ug.mL-1	PMID[459550]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	14.7	mm	PMID[459551]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	13.7	mm	PMID[459551]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	10.0	mm	PMID[459551]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	15.6	mm	PMID[459551]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	11.9	mm	PMID[459551]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	62500.0	nM	PMID[459551]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	31250.0	nM	PMID[459551]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	15600.0	nM	PMID[459551]

☑ 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 NPC282577 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	295
0.1-0.2	1565
0.2-0.3	3450
0.3-0.4	10032
0.4-0.5	9188
0.5-0.6	6474
0.6-0.7	8220
0.7-0.8	2942
0.8-0.85	383
0.85-0.9	117
0.9-0.95	26
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9746	High Similarity	NPC123506
0.9661	High Similarity	NPC199273
0.9583	High Similarity	NPC72667
0.9504	High Similarity	NPC96024
0.95	High Similarity	NPC254492
0.9426	High Similarity	NPC171460
0.9421	High Similarity	NPC69424
0.9421	High Similarity	NPC78364
0.9421	High Similarity	NPC84672
0.9421	High Similarity	NPC176130
0.9412	High Similarity	NPC273683
0.9194	High Similarity	NPC108129
0.9187	High Similarity	NPC3009
0.912	High Similarity	NPC471851
0.9113	High Similarity	NPC276238
0.9113	High Similarity	NPC303910
0.9083	High Similarity	NPC154696
0.9024	High Similarity	NPC15837
0.9008	High Similarity	NPC307174
0.9	High Similarity	NPC190971
0.8976	High Similarity	NPC477139
0.8976	High Similarity	NPC138472
0.8976	High Similarity	NPC78307
0.8966	High Similarity	NPC242136
0.8934	High Similarity	NPC275145
0.8906	High Similarity	NPC202225
0.8889	High Similarity	NPC253488
0.8879	High Similarity	NPC231717
0.8843	High Similarity	NPC259703
0.8843	High Similarity	NPC32322
0.8828	High Similarity	NPC59459
0.8828	High Similarity	NPC111845
0.8819	High Similarity	NPC41847
0.877	High Similarity	NPC120545
0.876	High Similarity	NPC206778
0.876	High Similarity	NPC285829
0.876	High Similarity	NPC50924
0.872	High Similarity	NPC160499
0.872	High Similarity	NPC474737
0.8702	High Similarity	NPC36868
0.8702	High Similarity	NPC475957
0.8699	High Similarity	NPC91478
0.8692	High Similarity	NPC290803
0.8682	High Similarity	NPC263817
0.8678	High Similarity	NPC473767
0.8672	High Similarity	NPC93015
0.8661	High Similarity	NPC117899
0.8655	High Similarity	NPC322197
0.864	High Similarity	NPC137750
0.8636	High Similarity	NPC230811
0.8626	High Similarity	NPC86524
0.8626	High Similarity	NPC471670
0.8621	High Similarity	NPC95172
0.8607	High Similarity	NPC478121
0.8605	High Similarity	NPC312560
0.8594	High Similarity	NPC198305
0.8594	High Similarity	NPC117609
0.8594	High Similarity	NPC27659
0.8583	High Similarity	NPC48248
0.8583	High Similarity	NPC193203
0.8583	High Similarity	NPC477453
0.8571	High Similarity	NPC3224
0.8571	High Similarity	NPC71610
0.8571	High Similarity	NPC231774
0.8571	High Similarity	NPC306765
0.8561	High Similarity	NPC53001
0.8561	High Similarity	NPC471452
0.856	High Similarity	NPC173978
0.856	High Similarity	NPC68756
0.856	High Similarity	NPC142956
0.856	High Similarity	NPC310540
0.856	High Similarity	NPC152525
0.855	High Similarity	NPC22644
0.855	High Similarity	NPC283088
0.855	High Similarity	NPC153088
0.8548	High Similarity	NPC176208
0.8538	High Similarity	NPC53896
0.8538	High Similarity	NPC52407
0.8538	High Similarity	NPC267205
0.8537	High Similarity	NPC241001
0.8527	High Similarity	NPC18798
0.8527	High Similarity	NPC239134
0.8527	High Similarity	NPC244699
0.8522	High Similarity	NPC21594
0.8516	High Similarity	NPC99731
0.8516	High Similarity	NPC34414
0.8516	High Similarity	NPC278928
0.8516	High Similarity	NPC146647
0.8512	High Similarity	NPC160199
0.8512	High Similarity	NPC174087
0.8507	High Similarity	NPC181560
0.8507	High Similarity	NPC169452
0.8504	High Similarity	NPC19432
0.85	High Similarity	NPC161304
0.8496	Intermediate Similarity	NPC87723
0.8492	Intermediate Similarity	NPC477454
0.8485	Intermediate Similarity	NPC191976
0.8485	Intermediate Similarity	NPC315275
0.8485	Intermediate Similarity	NPC254847
0.848	Intermediate Similarity	NPC471187
0.848	Intermediate Similarity	NPC174991
0.8473	Intermediate Similarity	NPC166480
0.8473	Intermediate Similarity	NPC12070
0.8473	Intermediate Similarity	NPC282780
0.8468	Intermediate Similarity	NPC162935
0.8468	Intermediate Similarity	NPC249340
0.8462	Intermediate Similarity	NPC58685
0.8462	Intermediate Similarity	NPC183103
0.8462	Intermediate Similarity	NPC309430
0.845	Intermediate Similarity	NPC62219
0.8448	Intermediate Similarity	NPC228737
0.8448	Intermediate Similarity	NPC226699
0.8443	Intermediate Similarity	NPC474890
0.8443	Intermediate Similarity	NPC161943
0.8443	Intermediate Similarity	NPC328694
0.8443	Intermediate Similarity	NPC273282
0.8438	Intermediate Similarity	NPC229894
0.8438	Intermediate Similarity	NPC282923
0.8433	Intermediate Similarity	NPC138099
0.8433	Intermediate Similarity	NPC162939
0.8433	Intermediate Similarity	NPC242994
0.843	Intermediate Similarity	NPC108288
0.843	Intermediate Similarity	NPC83718
0.8425	Intermediate Similarity	NPC473691
0.8421	Intermediate Similarity	NPC53206
0.8421	Intermediate Similarity	NPC277559
0.8421	Intermediate Similarity	NPC471905
0.8421	Intermediate Similarity	NPC53414
0.8413	Intermediate Similarity	NPC164014
0.8413	Intermediate Similarity	NPC234890
0.8413	Intermediate Similarity	NPC74507
0.8413	Intermediate Similarity	NPC181334
0.8409	Intermediate Similarity	NPC258502
0.8409	Intermediate Similarity	NPC80035
0.8409	Intermediate Similarity	NPC249272
0.84	Intermediate Similarity	NPC164947
0.84	Intermediate Similarity	NPC300274
0.84	Intermediate Similarity	NPC121168
0.84	Intermediate Similarity	NPC11250
0.8397	Intermediate Similarity	NPC225051
0.8397	Intermediate Similarity	NPC180261
0.8397	Intermediate Similarity	NPC48036
0.8397	Intermediate Similarity	NPC37299
0.8397	Intermediate Similarity	NPC115458
0.8397	Intermediate Similarity	NPC114183
0.839	Intermediate Similarity	NPC474057
0.8387	Intermediate Similarity	NPC216216
0.8385	Intermediate Similarity	NPC72669
0.8385	Intermediate Similarity	NPC164295
0.8385	Intermediate Similarity	NPC279596
0.8385	Intermediate Similarity	NPC85342
0.8385	Intermediate Similarity	NPC474517
0.8385	Intermediate Similarity	NPC17083
0.8382	Intermediate Similarity	NPC193555
0.8372	Intermediate Similarity	NPC92624
0.837	Intermediate Similarity	NPC471853
0.8362	Intermediate Similarity	NPC6984
0.8359	Intermediate Similarity	NPC324209
0.8358	Intermediate Similarity	NPC13715
0.8358	Intermediate Similarity	NPC61398
0.8358	Intermediate Similarity	NPC4214
0.8358	Intermediate Similarity	NPC416
0.8346	Intermediate Similarity	NPC131799
0.8346	Intermediate Similarity	NPC118919
0.8346	Intermediate Similarity	NPC474311
0.8333	Intermediate Similarity	NPC474519
0.8333	Intermediate Similarity	NPC135062
0.8333	Intermediate Similarity	NPC375356
0.8333	Intermediate Similarity	NPC270899
0.8321	Intermediate Similarity	NPC165612
0.8321	Intermediate Similarity	NPC100242
0.8321	Intermediate Similarity	NPC175738
0.832	Intermediate Similarity	NPC295034
0.832	Intermediate Similarity	NPC25168
0.8308	Intermediate Similarity	NPC136588
0.8308	Intermediate Similarity	NPC199253
0.8308	Intermediate Similarity	NPC259942
0.8308	Intermediate Similarity	NPC55949
0.8308	Intermediate Similarity	NPC470725
0.8296	Intermediate Similarity	NPC143438
0.8295	Intermediate Similarity	NPC234175
0.8295	Intermediate Similarity	NPC237225
0.8295	Intermediate Similarity	NPC95537
0.8295	Intermediate Similarity	NPC24869
0.8293	Intermediate Similarity	NPC41567
0.8291	Intermediate Similarity	NPC34715
0.8291	Intermediate Similarity	NPC151477
0.8284	Intermediate Similarity	NPC119542
0.8284	Intermediate Similarity	NPC49911
0.8284	Intermediate Similarity	NPC264022
0.8281	Intermediate Similarity	NPC295202
0.8281	Intermediate Similarity	NPC227741
0.8281	Intermediate Similarity	NPC136342
0.8281	Intermediate Similarity	NPC49647
0.8271	Intermediate Similarity	NPC477596
0.8268	Intermediate Similarity	NPC12818
0.8268	Intermediate Similarity	NPC236189
0.8268	Intermediate Similarity	NPC474766
0.8264	Intermediate Similarity	NPC186933
0.8258	Intermediate Similarity	NPC314048

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 NPC282577 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	320
0.1-0.2	973
0.2-0.3	1379
0.3-0.4	2621
0.4-0.5	2135
0.5-0.6	1173
0.6-0.7	450
0.7-0.8	92
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8525	High Similarity	NPD4196	Clinical (unspecified phase)
0.8485	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.843	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.832	Intermediate Similarity	NPD1201	Approved
0.8306	Intermediate Similarity	NPD2932	Approved
0.8203	Intermediate Similarity	NPD1470	Approved
0.816	Intermediate Similarity	NPD3019	Approved
0.8	Intermediate Similarity	NPD7390	Discontinued
0.7883	Intermediate Similarity	NPD5405	Approved
0.7883	Intermediate Similarity	NPD5404	Approved
0.7883	Intermediate Similarity	NPD5408	Approved
0.7883	Intermediate Similarity	NPD5406	Approved
0.7786	Intermediate Similarity	NPD1164	Approved
0.771	Intermediate Similarity	NPD1283	Approved
0.7686	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD288	Approved
0.7661	Intermediate Similarity	NPD7635	Approved
0.766	Intermediate Similarity	NPD7003	Approved
0.7656	Intermediate Similarity	NPD1651	Approved
0.7647	Intermediate Similarity	NPD943	Approved
0.7597	Intermediate Similarity	NPD4626	Approved
0.7586	Intermediate Similarity	NPD844	Approved
0.7569	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD4750	Phase 3
0.7557	Intermediate Similarity	NPD3972	Approved
0.7554	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7554	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3300	Phase 2
0.754	Intermediate Similarity	NPD5951	Approved
0.7538	Intermediate Similarity	NPD3026	Approved
0.7538	Intermediate Similarity	NPD3023	Approved
0.7536	Intermediate Similarity	NPD1607	Approved
0.7519	Intermediate Similarity	NPD3025	Approved
0.7519	Intermediate Similarity	NPD3024	Approved
0.7518	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7481	Intermediate Similarity	NPD1281	Approved
0.7447	Intermediate Similarity	NPD2346	Discontinued
0.7442	Intermediate Similarity	NPD9545	Approved
0.7436	Intermediate Similarity	NPD1809	Phase 2
0.7429	Intermediate Similarity	NPD2799	Discontinued
0.7414	Intermediate Similarity	NPD845	Approved
0.7398	Intermediate Similarity	NPD2342	Discontinued
0.7395	Intermediate Similarity	NPD3020	Approved
0.7391	Intermediate Similarity	NPD1240	Approved
0.7368	Intermediate Similarity	NPD1755	Approved
0.7365	Intermediate Similarity	NPD7458	Discontinued
0.736	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD74	Approved
0.7339	Intermediate Similarity	NPD9266	Approved
0.7339	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD2798	Approved
0.7329	Intermediate Similarity	NPD2533	Approved
0.7329	Intermediate Similarity	NPD2532	Approved
0.7329	Intermediate Similarity	NPD2534	Approved
0.7328	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2344	Approved
0.7319	Intermediate Similarity	NPD6663	Approved
0.7313	Intermediate Similarity	NPD1876	Approved
0.7302	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD8166	Discontinued
0.7287	Intermediate Similarity	NPD9493	Approved
0.7279	Intermediate Similarity	NPD5736	Approved
0.7258	Intermediate Similarity	NPD9263	Approved
0.7258	Intermediate Similarity	NPD9264	Approved
0.7258	Intermediate Similarity	NPD9267	Approved
0.7254	Intermediate Similarity	NPD6099	Approved
0.7254	Intermediate Similarity	NPD6100	Approved
0.7252	Intermediate Similarity	NPD5691	Approved
0.7248	Intermediate Similarity	NPD3226	Approved
0.7246	Intermediate Similarity	NPD3764	Approved
0.7222	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7213	Intermediate Similarity	NPD1930	Approved
0.7213	Intermediate Similarity	NPD1929	Approved
0.7213	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD1510	Phase 2
0.7176	Intermediate Similarity	NPD3091	Approved
0.7172	Intermediate Similarity	NPD3750	Approved
0.7172	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD7819	Suspended
0.7164	Intermediate Similarity	NPD4878	Approved
0.7164	Intermediate Similarity	NPD9269	Phase 2
0.7153	Intermediate Similarity	NPD9494	Approved
0.7152	Intermediate Similarity	NPD7473	Discontinued
0.7143	Intermediate Similarity	NPD3022	Approved
0.7143	Intermediate Similarity	NPD2860	Approved
0.7143	Intermediate Similarity	NPD3021	Approved
0.7143	Intermediate Similarity	NPD2859	Approved
0.7133	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD2309	Approved
0.7121	Intermediate Similarity	NPD9268	Approved
0.7115	Intermediate Similarity	NPD6959	Discontinued
0.7111	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD2066	Phase 3
0.7095	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.707	Intermediate Similarity	NPD6232	Discontinued
0.7068	Intermediate Similarity	NPD4059	Approved
0.7059	Intermediate Similarity	NPD2933	Approved
0.7059	Intermediate Similarity	NPD2934	Approved
0.7055	Intermediate Similarity	NPD4628	Phase 3
0.7054	Intermediate Similarity	NPD1241	Discontinued
0.7047	Intermediate Similarity	NPD6273	Approved
0.7042	Intermediate Similarity	NPD6651	Approved
0.7037	Intermediate Similarity	NPD1608	Approved
0.7021	Intermediate Similarity	NPD2979	Phase 3
0.7016	Intermediate Similarity	NPD1237	Approved
0.6992	Remote Similarity	NPD940	Approved
0.6992	Remote Similarity	NPD846	Approved
0.6986	Remote Similarity	NPD2800	Approved
0.698	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD230	Phase 1
0.6966	Remote Similarity	NPD1471	Phase 3
0.6963	Remote Similarity	NPD3092	Approved
0.6948	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD3495	Discontinued
0.694	Remote Similarity	NPD2286	Discontinued
0.694	Remote Similarity	NPD1751	Approved
0.6935	Remote Similarity	NPD9261	Approved
0.6918	Remote Similarity	NPD1549	Phase 2
0.6906	Remote Similarity	NPD4208	Discontinued
0.6903	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD4060	Phase 1
0.6894	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6891	Remote Similarity	NPD7631	Approved
0.6884	Remote Similarity	NPD2797	Approved
0.6879	Remote Similarity	NPD411	Approved
0.6879	Remote Similarity	NPD2313	Discontinued
0.6879	Remote Similarity	NPD3268	Approved
0.6875	Remote Similarity	NPD1792	Phase 2
0.687	Remote Similarity	NPD9281	Approved
0.687	Remote Similarity	NPD497	Approved
0.6866	Remote Similarity	NPD4093	Discontinued
0.6863	Remote Similarity	NPD4380	Phase 2
0.6852	Remote Similarity	NPD5844	Phase 1
0.6852	Remote Similarity	NPD6020	Phase 2
0.6849	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7610	Discontinued
0.6831	Remote Similarity	NPD8032	Phase 2
0.6828	Remote Similarity	NPD4308	Phase 3
0.6828	Remote Similarity	NPD3748	Approved
0.6818	Remote Similarity	NPD256	Approved
0.6818	Remote Similarity	NPD255	Approved
0.6815	Remote Similarity	NPD17	Approved
0.6815	Remote Similarity	NPD3095	Discontinued
0.6809	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD7008	Discontinued
0.6807	Remote Similarity	NPD7609	Phase 3
0.68	Remote Similarity	NPD1511	Approved
0.6794	Remote Similarity	NPD496	Approved
0.6794	Remote Similarity	NPD498	Approved
0.6794	Remote Similarity	NPD495	Approved
0.6794	Remote Similarity	NPD1398	Phase 1
0.6788	Remote Similarity	NPD9717	Approved
0.6781	Remote Similarity	NPD2438	Suspended
0.6781	Remote Similarity	NPD4477	Approved
0.6781	Remote Similarity	NPD2531	Phase 2
0.6781	Remote Similarity	NPD2796	Approved
0.6781	Remote Similarity	NPD4476	Approved
0.6779	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD1693	Approved
0.6772	Remote Similarity	NPD1444	Approved
0.6772	Remote Similarity	NPD1445	Approved
0.6769	Remote Similarity	NPD6124	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7340	Approved
0.6765	Remote Similarity	NPD4879	Approved
0.6763	Remote Similarity	NPD1203	Approved
0.6763	Remote Similarity	NPD3094	Phase 2
0.6757	Remote Similarity	NPD1243	Approved
0.6752	Remote Similarity	NPD650	Approved
0.675	Remote Similarity	NPD5710	Approved
0.675	Remote Similarity	NPD5711	Approved
0.6739	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4749	Approved
0.6738	Remote Similarity	NPD4207	Discontinued
0.6733	Remote Similarity	NPD6884	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD8150	Discontinued
0.6724	Remote Similarity	NPD111	Approved
0.6723	Remote Similarity	NPD1089	Approved
0.6723	Remote Similarity	NPD1086	Approved
0.6723	Remote Similarity	NPD9258	Approved
0.6723	Remote Similarity	NPD1090	Approved
0.6723	Remote Similarity	NPD9256	Approved
0.672	Remote Similarity	NPD1932	Approved
0.6715	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD1512	Approved
0.671	Remote Similarity	NPD7411	Suspended
0.6709	Remote Similarity	NPD7075	Discontinued
0.6694	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD6696	Suspended
0.6691	Remote Similarity	NPD1778	Approved
0.669	Remote Similarity	NPD4625	Phase 3
0.669	Remote Similarity	NPD4097	Suspended
0.6688	Remote Similarity	NPD8438	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