NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	228.12
Volume:	252.645
LogP:	4.012
LogD:	2.988
LogS:	-3.526
# Rotatable Bonds:	0
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	3.346
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:	-4.983
MDCK Permeability:	8.053477358771488e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.008
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.91
30% Bioavailability (F30%):	0.807

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.147
Plasma Protein Binding (PPB):	96.50171661376953%
Volume Distribution (VD):	0.687
Pgp-substrate:	4.674798011779785%

ADMET: Metabolism

CYP1A2-inhibitor:	0.976
CYP1A2-substrate:	0.853
CYP2C19-inhibitor:	0.171
CYP2C19-substrate:	0.28
CYP2C9-inhibitor:	0.36
CYP2C9-substrate:	0.722
CYP2D6-inhibitor:	0.62
CYP2D6-substrate:	0.616
CYP3A4-inhibitor:	0.09
CYP3A4-substrate:	0.228

ADMET: Excretion

Clearance (CL):	9.097
Half-life (T1/2):	0.629

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.039
Drug-inuced Liver Injury (DILI):	0.88
AMES Toxicity:	0.693
Rat Oral Acute Toxicity:	0.784
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.952
Carcinogencity:	0.797
Eye Corrosion:	0.125
Eye Irritation:	0.96
Respiratory Toxicity:	0.828

Download Data

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

Natural Product: NPC133461

Natural Product ID:	NPC133461
*Common Name:**	Mansonone C
IUPAC Name:	3,8-dimethyl-5-propan-2-ylnaphthalene-1,2-dione
Synonyms:
Standard InCHIKey:	GREWJSSEUGRGIT-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C15H16O2/c1-8(2)11-6-5-9(3)13-12(11)7-10(4)14(16)15(13)17/h5-8H,1-4H3
SMILES:	CC1=Cc2c(ccc(c2C(=O)C1=O)C)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508283
PubChem CID:	21742
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]
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]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	Australian rainforest	n.a.	PMID[18039010]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18553924]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20218657]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23734721]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7928	Agave east-one	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8976.1	Agave americana var. marginata	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7830	Agave angustifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7928	Agave east-one	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7830	Agave angustifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8976.1	Agave americana var. marginata	Varieties	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7830	Agave angustifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20840	Ulmus parvifolia	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO960	Phlomis aurea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4348	Watasenia scintillans	Species	Enoploteuthidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17202	Lasallia asiae-orientalis	Species	Umbilicariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9565	Linum maritimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3546	Shorea balangeran	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11301	Ulmus glabra	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25866	Kaunia lasiophthalma	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11354	Streptomyces galbus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2124	Bulgaria inquinans	Species	Bulgariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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]
NPO6427	Wardomyces anomalus	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13058	Psychotria brachyceras	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11158	Diplopterygium rufopilosum	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19460	Karenia brevis	Species	Kareniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6423	Vitex cauliflora	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7535	Mansonia altissima	Species	Culicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8976	Agave americana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6878	Vesperus xatarti	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7830	Agave angustifolia	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24924	Saara hardwickii	Species	Agamidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9794	Dysoxylum fraseranum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11510	Astragalus flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5167	Peripentadenia mearsii	Species	Elaeocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12123	Geodia gigas	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15986	Alangium chinense	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19367	Thespesia populnea	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10455	Vaccinium uliginosum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10273	Dictyota flabellata	Species	Dictyotaceae	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	4
MIC	5
Others	7

Activity Type	# Activity
Cell Line	1
NON-MOLECULAR	10
Organism	4
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	IC50	=	1450.0	nM	PMID[509174]
NPT35	Others	n.a.		Activity	=	434.0	microM/min	PMID[509170]
NPT1266	Organism	Leptomonas seymouri	Leptomonas seymouri	IC50	=	4000.0	nM	PMID[509170]
NPT1267	Organism	Crithidia fasciculata	Crithidia fasciculata	IC50	=	6000.0	nM	PMID[509170]
NPT3494	Organism	Coxsackievirus	Coxsackievirus	IC50	>	20000.0	nM	PMID[509171]
NPT176	Organism	Artemia salina	Artemia salina	LC50	=	2.08	ug.mL-1	PMID[509172]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	13.7	mm	PMID[509173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	12.7	mm	PMID[509173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	9.3	mm	PMID[509173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	13.3	mm	PMID[509173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IZ	=	11.3	mm	PMID[509173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	62500.0	nM	PMID[509173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	15600.0	nM	PMID[509173]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	MIC	=	31250.0	nM	PMID[509173]

☑ 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 NPC133461 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	303
0.1-0.2	1594
0.2-0.3	4556
0.3-0.4	14538
0.4-0.5	14079
0.5-0.6	6335
0.6-0.7	1004
0.7-0.8	193
0.8-0.85	44
0.85-0.9	21
0.9-0.95	18
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC153885
0.977	High Similarity	NPC238219
0.9659	High Similarity	NPC260233
0.9655	High Similarity	NPC155232
0.9651	High Similarity	NPC173413
0.9444	High Similarity	NPC239185
0.9432	High Similarity	NPC188844
0.9432	High Similarity	NPC1682
0.9419	High Similarity	NPC157778
0.9412	High Similarity	NPC307
0.9412	High Similarity	NPC160339
0.9341	High Similarity	NPC75724
0.9341	High Similarity	NPC134882
0.9341	High Similarity	NPC49994
0.9318	High Similarity	NPC284475
0.9302	High Similarity	NPC43945
0.9231	High Similarity	NPC265220
0.9213	High Similarity	NPC323420
0.9205	High Similarity	NPC277277
0.914	High Similarity	NPC109514
0.914	High Similarity	NPC476993
0.9121	High Similarity	NPC185208
0.9121	High Similarity	NPC219573
0.9111	High Similarity	NPC289883
0.9	High Similarity	NPC59677
0.8947	High Similarity	NPC247976
0.8876	High Similarity	NPC418308
0.8864	High Similarity	NPC69057
0.8837	High Similarity	NPC215008
0.8824	High Similarity	NPC145053
0.8778	High Similarity	NPC19256
0.8764	High Similarity	NPC267262
0.8764	High Similarity	NPC153308
0.8706	High Similarity	NPC17408
0.8706	High Similarity	NPC190567
0.8706	High Similarity	NPC285716
0.8673	High Similarity	NPC100767
0.8602	High Similarity	NPC472880
0.8588	High Similarity	NPC300205
0.8539	High Similarity	NPC164526
0.85	High Similarity	NPC470252
0.8488	Intermediate Similarity	NPC164086
0.8478	Intermediate Similarity	NPC103346
0.8471	Intermediate Similarity	NPC103488
0.8471	Intermediate Similarity	NPC36342
0.8471	Intermediate Similarity	NPC285470
0.8471	Intermediate Similarity	NPC2785
0.8469	Intermediate Similarity	NPC329282
0.8462	Intermediate Similarity	NPC298115
0.8427	Intermediate Similarity	NPC252067
0.8409	Intermediate Similarity	NPC273758
0.8391	Intermediate Similarity	NPC273033
0.8391	Intermediate Similarity	NPC12936
0.8384	Intermediate Similarity	NPC474910
0.8384	Intermediate Similarity	NPC172483
0.8353	Intermediate Similarity	NPC245966
0.8351	Intermediate Similarity	NPC472879
0.8333	Intermediate Similarity	NPC474057
0.8276	Intermediate Similarity	NPC71664
0.8261	Intermediate Similarity	NPC113307
0.8261	Intermediate Similarity	NPC325709
0.8252	Intermediate Similarity	NPC292834
0.8202	Intermediate Similarity	NPC39600
0.8202	Intermediate Similarity	NPC197581
0.8182	Intermediate Similarity	NPC472691
0.8182	Intermediate Similarity	NPC471829
0.8182	Intermediate Similarity	NPC274443
0.8182	Intermediate Similarity	NPC475939
0.8182	Intermediate Similarity	NPC474866
0.8173	Intermediate Similarity	NPC470253
0.8155	Intermediate Similarity	NPC265513
0.8095	Intermediate Similarity	NPC326664
0.8081	Intermediate Similarity	NPC222390
0.8081	Intermediate Similarity	NPC244427
0.8077	Intermediate Similarity	NPC280789
0.8	Intermediate Similarity	NPC143768
0.8	Intermediate Similarity	NPC93287
0.7979	Intermediate Similarity	NPC110420
0.7979	Intermediate Similarity	NPC58872
0.7979	Intermediate Similarity	NPC303967
0.7979	Intermediate Similarity	NPC67585
0.7978	Intermediate Similarity	NPC73978
0.7978	Intermediate Similarity	NPC100039
0.7955	Intermediate Similarity	NPC139901
0.7955	Intermediate Similarity	NPC151405
0.7941	Intermediate Similarity	NPC185763
0.7941	Intermediate Similarity	NPC472699
0.7941	Intermediate Similarity	NPC472700
0.7941	Intermediate Similarity	NPC37914
0.7941	Intermediate Similarity	NPC83409
0.7925	Intermediate Similarity	NPC471721
0.7895	Intermediate Similarity	NPC125226
0.7882	Intermediate Similarity	NPC285679
0.7865	Intermediate Similarity	NPC157055
0.7865	Intermediate Similarity	NPC95868
0.7865	Intermediate Similarity	NPC477703
0.7864	Intermediate Similarity	NPC203732
0.7864	Intermediate Similarity	NPC472683
0.7864	Intermediate Similarity	NPC472696
0.7864	Intermediate Similarity	NPC472701
0.7864	Intermediate Similarity	NPC472695
0.785	Intermediate Similarity	NPC215419
0.785	Intermediate Similarity	NPC474095
0.785	Intermediate Similarity	NPC217111
0.7843	Intermediate Similarity	NPC134120
0.7822	Intermediate Similarity	NPC329556
0.78	Intermediate Similarity	NPC112552
0.7789	Intermediate Similarity	NPC26224
0.7788	Intermediate Similarity	NPC192577
0.7765	Intermediate Similarity	NPC74458
0.7757	Intermediate Similarity	NPC67377
0.7753	Intermediate Similarity	NPC272260
0.7736	Intermediate Similarity	NPC218855
0.7736	Intermediate Similarity	NPC186128
0.7736	Intermediate Similarity	NPC66208
0.7727	Intermediate Similarity	NPC318173
0.7727	Intermediate Similarity	NPC9796
0.7706	Intermediate Similarity	NPC469843
0.7692	Intermediate Similarity	NPC230068
0.7692	Intermediate Similarity	NPC112903
0.7685	Intermediate Similarity	NPC93181
0.7685	Intermediate Similarity	NPC186933
0.7685	Intermediate Similarity	NPC228936
0.7677	Intermediate Similarity	NPC156021
0.7677	Intermediate Similarity	NPC240042
0.7677	Intermediate Similarity	NPC226041
0.7664	Intermediate Similarity	NPC13784
0.7664	Intermediate Similarity	NPC471481
0.7647	Intermediate Similarity	NPC95289
0.7642	Intermediate Similarity	NPC137315
0.764	Intermediate Similarity	NPC137847
0.764	Intermediate Similarity	NPC76455
0.7636	Intermediate Similarity	NPC323440
0.7636	Intermediate Similarity	NPC80605
0.7636	Intermediate Similarity	NPC222968
0.7624	Intermediate Similarity	NPC225079
0.7615	Intermediate Similarity	NPC135730
0.7609	Intermediate Similarity	NPC149263
0.7609	Intermediate Similarity	NPC324624
0.76	Intermediate Similarity	NPC145052
0.7593	Intermediate Similarity	NPC130591
0.7593	Intermediate Similarity	NPC234637
0.7589	Intermediate Similarity	NPC232958
0.7529	Intermediate Similarity	NPC98880
0.7528	Intermediate Similarity	NPC179726
0.7528	Intermediate Similarity	NPC329318
0.7528	Intermediate Similarity	NPC298023
0.7527	Intermediate Similarity	NPC267704
0.7526	Intermediate Similarity	NPC475023
0.7526	Intermediate Similarity	NPC475059
0.7525	Intermediate Similarity	NPC221825
0.7523	Intermediate Similarity	NPC274839
0.75	Intermediate Similarity	NPC202015
0.75	Intermediate Similarity	NPC471186
0.7477	Intermediate Similarity	NPC291799
0.7477	Intermediate Similarity	NPC210089
0.7471	Intermediate Similarity	NPC54269
0.7455	Intermediate Similarity	NPC260886
0.7453	Intermediate Similarity	NPC318327
0.7451	Intermediate Similarity	NPC133809
0.7451	Intermediate Similarity	NPC136810
0.7451	Intermediate Similarity	NPC128248
0.7449	Intermediate Similarity	NPC475057
0.7447	Intermediate Similarity	NPC123476
0.7431	Intermediate Similarity	NPC241851
0.7431	Intermediate Similarity	NPC196673
0.7426	Intermediate Similarity	NPC329387
0.7426	Intermediate Similarity	NPC317280
0.7423	Intermediate Similarity	NPC274455
0.7423	Intermediate Similarity	NPC86670
0.7423	Intermediate Similarity	NPC70940
0.7416	Intermediate Similarity	NPC78500
0.7412	Intermediate Similarity	NPC311343
0.7407	Intermediate Similarity	NPC212415
0.7396	Intermediate Similarity	NPC477693
0.7396	Intermediate Similarity	NPC477704
0.7396	Intermediate Similarity	NPC473345
0.7391	Intermediate Similarity	NPC242628
0.7379	Intermediate Similarity	NPC304873
0.7379	Intermediate Similarity	NPC25458
0.7368	Intermediate Similarity	NPC144547
0.7368	Intermediate Similarity	NPC472981
0.7364	Intermediate Similarity	NPC476357
0.7364	Intermediate Similarity	NPC470764
0.7358	Intermediate Similarity	NPC470391
0.7347	Intermediate Similarity	NPC476484
0.7345	Intermediate Similarity	NPC476645
0.7328	Intermediate Similarity	NPC318067
0.7328	Intermediate Similarity	NPC328107
0.7321	Intermediate Similarity	NPC61651
0.7321	Intermediate Similarity	NPC268930
0.7304	Intermediate Similarity	NPC269923
0.7304	Intermediate Similarity	NPC167323
0.7294	Intermediate Similarity	NPC6107
0.7292	Intermediate Similarity	NPC194326
0.7282	Intermediate Similarity	NPC473325
0.7281	Intermediate Similarity	NPC289432
0.7281	Intermediate Similarity	NPC238861
0.7281	Intermediate Similarity	NPC988
0.7281	Intermediate Similarity	NPC77000

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 NPC133461 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	277
0.1-0.2	1048
0.2-0.3	1496
0.3-0.4	3281
0.4-0.5	2098
0.5-0.6	773
0.6-0.7	130
0.7-0.8	39
0.8-0.85	4
0.85-0.9	0
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9444	High Similarity	NPD3495	Discontinued
0.9432	High Similarity	NPD7631	Approved
0.9318	High Similarity	NPD7609	Phase 3
0.9302	High Similarity	NPD650	Approved
0.8391	Intermediate Similarity	NPD942	Approved
0.8387	Intermediate Similarity	NPD1508	Approved
0.8333	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD1843	Approved
0.7879	Intermediate Similarity	NPD2066	Phase 3
0.7865	Intermediate Similarity	NPD1507	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD1930	Approved
0.7822	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.7822	Intermediate Similarity	NPD1929	Approved
0.7732	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.7723	Intermediate Similarity	NPD2193	Phase 2
0.7723	Intermediate Similarity	NPD2648	Phase 3
0.766	Intermediate Similarity	NPD1087	Approved
0.766	Intermediate Similarity	NPD506	Clinical (unspecified phase)
0.7549	Intermediate Similarity	NPD2196	Discontinued
0.7549	Intermediate Similarity	NPD1932	Approved
0.7475	Intermediate Similarity	NPD1693	Approved
0.7453	Intermediate Similarity	NPD2329	Discontinued
0.7423	Intermediate Similarity	NPD1089	Approved
0.7423	Intermediate Similarity	NPD1086	Approved
0.7423	Intermediate Similarity	NPD1090	Approved
0.7411	Intermediate Similarity	NPD7009	Phase 2
0.7407	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD5951	Approved
0.7333	Intermediate Similarity	NPD1677	Discontinued
0.7321	Intermediate Similarity	NPD7610	Discontinued
0.732	Intermediate Similarity	NPD800	Approved
0.73	Intermediate Similarity	NPD6049	Phase 2
0.73	Intermediate Similarity	NPD6048	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7281	Intermediate Similarity	NPD5836	Discontinued
0.7273	Intermediate Similarity	NPD1088	Approved
0.7222	Intermediate Similarity	NPD1317	Discontinued
0.7217	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD2171	Approved
0.72	Intermediate Similarity	NPD1563	Approved
0.717	Intermediate Similarity	NPD2192	Approved
0.717	Intermediate Similarity	NPD2197	Approved
0.7157	Intermediate Similarity	NPD1099	Approved
0.7157	Intermediate Similarity	NPD1100	Approved
0.713	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD2577	Clinical (unspecified phase)
0.7069	Intermediate Similarity	NPD4879	Approved
0.7064	Intermediate Similarity	NPD664	Approved
0.7059	Intermediate Similarity	NPD1989	Approved
0.7053	Intermediate Similarity	NPD3971	Phase 1
0.7027	Intermediate Similarity	NPD6858	Approved
0.7027	Intermediate Similarity	NPD7094	Approved
0.7	Intermediate Similarity	NPD1239	Approved
0.7	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.699	Remote Similarity	NPD1564	Approved
0.699	Remote Similarity	NPD1565	Approved
0.699	Remote Similarity	NPD1566	Phase 3
0.6981	Remote Similarity	NPD3357	Discontinued
0.6961	Remote Similarity	NPD4094	Approved
0.6916	Remote Similarity	NPD1237	Approved
0.6916	Remote Similarity	NPD164	Approved
0.6907	Remote Similarity	NPD5734	Clinical (unspecified phase)
0.69	Remote Similarity	NPD3672	Approved
0.69	Remote Similarity	NPD3673	Approved
0.6887	Remote Similarity	NPD813	Approved
0.6882	Remote Similarity	NPD225	Approved
0.6882	Remote Similarity	NPD227	Approved
0.6863	Remote Similarity	NPD1202	Approved
0.6842	Remote Similarity	NPD3317	Approved
0.6837	Remote Similarity	NPD9259	Approved
0.6837	Remote Similarity	NPD9257	Approved
0.6827	Remote Similarity	NPD4655	Approved
0.6827	Remote Similarity	NPD4657	Approved
0.6818	Remote Similarity	NPD2182	Approved
0.6809	Remote Similarity	NPD9490	Approved
0.6807	Remote Similarity	NPD4878	Approved
0.68	Remote Similarity	NPD5347	Phase 2
0.68	Remote Similarity	NPD5346	Phase 2
0.6759	Remote Similarity	NPD5909	Discontinued
0.6701	Remote Similarity	NPD9491	Approved
0.6695	Remote Similarity	NPD2345	Approved
0.6694	Remote Similarity	NPD2754	Discontinued
0.6694	Remote Similarity	NPD6330	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7076	Approved
0.6667	Remote Similarity	NPD226	Approved
0.6667	Remote Similarity	NPD7077	Approved
0.6639	Remote Similarity	NPD3836	Clinical (unspecified phase)
0.661	Remote Similarity	NPD1245	Approved
0.66	Remote Similarity	NPD4793	Discontinued
0.6581	Remote Similarity	NPD997	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD6027	Approved
0.6574	Remote Similarity	NPD6024	Approved
0.6569	Remote Similarity	NPD9256	Approved
0.6569	Remote Similarity	NPD9258	Approved
0.656	Remote Similarity	NPD7008	Discontinued
0.656	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD9716	Approved
0.6542	Remote Similarity	NPD1238	Approved
0.6529	Remote Similarity	NPD3972	Approved
0.6514	Remote Similarity	NPD6647	Phase 2
0.6496	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD3135	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD1651	Approved
0.6466	Remote Similarity	NPD1246	Approved
0.6466	Remote Similarity	NPD2508	Discontinued
0.6457	Remote Similarity	NPD7961	Discontinued
0.6452	Remote Similarity	NPD4058	Approved
0.6449	Remote Similarity	NPD466	Approved
0.6446	Remote Similarity	NPD6287	Discontinued
0.6446	Remote Similarity	NPD1201	Approved
0.6423	Remote Similarity	NPD1876	Approved
0.6417	Remote Similarity	NPD2932	Approved
0.6374	Remote Similarity	NPD9497	Clinical (unspecified phase)
0.6371	Remote Similarity	NPD1470	Approved
0.6371	Remote Similarity	NPD3244	Pre-registration
0.6371	Remote Similarity	NPD3245	Phase 3
0.6364	Remote Similarity	NPD675	Discontinued
0.6346	Remote Similarity	NPD1007	Discontinued
0.6341	Remote Similarity	NPD3547	Approved
0.6341	Remote Similarity	NPD3549	Approved
0.6341	Remote Similarity	NPD3550	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD3099	Discontinued
0.6333	Remote Similarity	NPD3025	Approved
0.6333	Remote Similarity	NPD3024	Approved
0.6325	Remote Similarity	NPD2319	Discontinued
0.6321	Remote Similarity	NPD9260	Approved
0.6311	Remote Similarity	NPD1281	Approved
0.6303	Remote Similarity	NPD6065	Approved
0.629	Remote Similarity	NPD2056	Discontinued
0.6281	Remote Similarity	NPD3019	Approved
0.6277	Remote Similarity	NPD4687	Approved
0.6273	Remote Similarity	NPD4803	Discontinued
0.627	Remote Similarity	NPD7084	Phase 3
0.626	Remote Similarity	NPD3356	Approved
0.626	Remote Similarity	NPD3355	Approved
0.6239	Remote Similarity	NPD742	Approved
0.6239	Remote Similarity	NPD1241	Discontinued
0.6239	Remote Similarity	NPD6010	Discontinued
0.623	Remote Similarity	NPD3023	Approved
0.623	Remote Similarity	NPD3026	Approved
0.6216	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD1101	Approved
0.6202	Remote Similarity	NPD1874	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD1217	Clinical (unspecified phase)
0.619	Remote Similarity	NPD2798	Approved
0.619	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.619	Remote Similarity	NPD4980	Approved
0.6186	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6186	Remote Similarity	NPD1073	Approved
0.6186	Remote Similarity	NPD1075	Approved
0.6186	Remote Similarity	NPD1074	Approved
0.616	Remote Similarity	NPD1283	Approved
0.616	Remote Similarity	NPD1482	Clinical (unspecified phase)
0.6148	Remote Similarity	NPD4199	Phase 3
0.6148	Remote Similarity	NPD1727	Approved
0.6147	Remote Similarity	NPD5926	Approved
0.6147	Remote Similarity	NPD253	Approved
0.6139	Remote Similarity	NPD4544	Approved
0.6129	Remote Similarity	NPD6637	Approved
0.6129	Remote Similarity	NPD4691	Approved
0.6124	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6121	Remote Similarity	NPD3644	Approved
0.6121	Remote Similarity	NPD3642	Approved
0.6121	Remote Similarity	NPD3643	Approved
0.6119	Remote Similarity	NPD2346	Discontinued
0.6117	Remote Similarity	NPD1282	Approved
0.6111	Remote Similarity	NPD3093	Approved
0.6111	Remote Similarity	NPD5653	Discontinued
0.6111	Remote Similarity	NPD5206	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD1766	Approved
0.6106	Remote Similarity	NPD1765	Approved
0.6106	Remote Similarity	NPD1767	Approved
0.6106	Remote Similarity	NPD1761	Approved
0.6106	Remote Similarity	NPD1018	Approved
0.6106	Remote Similarity	NPD1763	Approved
0.6105	Remote Similarity	NPD5733	Approved
0.6103	Remote Similarity	NPD7003	Approved
0.6094	Remote Similarity	NPD7055	Discontinued
0.6091	Remote Similarity	NPD7798	Approved
0.609	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.608	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.608	Remote Similarity	NPD5157	Phase 1
0.608	Remote Similarity	NPD5159	Phase 2
0.6077	Remote Similarity	NPD7713	Phase 3
0.6071	Remote Similarity	NPD9261	Approved
0.6068	Remote Similarity	NPD9508	Approved
0.6064	Remote Similarity	NPD5276	Approved
0.6061	Remote Similarity	NPD3979	Approved
0.6061	Remote Similarity	NPD3904	Approved
0.6061	Remote Similarity	NPD3981	Approved
0.6061	Remote Similarity	NPD3903	Approved
0.6058	Remote Similarity	NPD8239	Clinical (unspecified phase)
0.605	Remote Similarity	NPD851	Approved
0.605	Remote Similarity	NPD853	Approved
0.605	Remote Similarity	NPD2629	Approved
0.605	Remote Similarity	NPD4766	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