NPASS Compound

Natural Product: NPC52394

Natural Product ID	NPC52394
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	AYXPYQRXGNDJFU-IROTVPAZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	7308311
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids [CHEMONTID:0001781] Aromadendrane sesquiterpenoids [CHEMONTID:0003562] 5,10-cycloaromadendrane sesquiterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 42 44 0 0 0 0 0 0 0 0999 V2000 -0.4503 -2.9345 0.0997 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2641 -1.7139 -0.1401 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0158 -1.2096 1.0506 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1555 0.3022 0.8351 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4608 0.5601 -0.4965 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3991 -0.4867 -0.4884 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6190 -0.3706 0.5777 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6709 0.6199 0.4144 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3874 1.4885 -0.7860 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2617 2.4006 -0.3772 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0845 1.9402 -0.7549 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0910 2.8537 -0.0325 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2696 2.2403 -2.1266 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0497 -0.7853 0.3123 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8114 -1.3358 1.5272 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4472 -1.2943 -1.0385 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2321 -3.3969 -0.8984 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0825 -3.6699 0.6332 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4588 -2.7998 0.6823 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9788 -1.9081 -0.9570 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0041 -1.7112 1.0615 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5399 -1.4384 2.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2428 0.5099 0.7669 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6614 0.8320 1.6697 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2164 0.2361 -1.2748 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0050 -0.7133 -1.5004 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2450 -0.5387 1.6149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9796 1.2229 1.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3145 2.1003 -0.9546 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1926 0.9358 -1.7014 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4548 3.3835 -0.8991 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3077 2.6213 0.7093 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9233 3.8746 -0.4471 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7686 2.9273 1.0454 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1175 2.5041 -0.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0516 1.4287 -2.6411 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6529 -1.9862 1.1833 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1267 -1.9265 2.1705 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1803 -0.5019 2.1629 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3794 -1.9047 -0.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7026 -1.9024 -1.5458 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7625 -0.4534 -1.7237 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 11 13 1 6 8 14 1 0 14 15 1 0 14 16 1 0 6 2 1 0 14 7 1 0 11 5 1 0 1 17 1 0 1 18 1 0 1 19 1 0 2 20 1 6 3 21 1 0 3 22 1 0 4 23 1 0 4 24 1 0 5 25 1 6 6 26 1 6 7 27 1 1 8 28 1 1 9 29 1 0 9 30 1 0 10 31 1 0 10 32 1 0 12 33 1 0 12 34 1 0 12 35 1 0 13 36 1 0 15 37 1 0 15 38 1 0 15 39 1 0 16 40 1 0 16 41 1 0 16 42 1 0 M END

Standard InCHIKey	AYXPYQRXGNDJFU-IROTVPAZSA-N
Standard InCHI	InChI=1S/C15H26O/c1-9-5-6-10-12(9)13-11(14(13,2)3)7-8-15(10,4)16/h9-13,16H,5-8H2,1-4H3/t9-,10+,11-,12-,13-,15+/m0/s1
SMILES	C[C@H]1CC[C@@H]2[C@H]1[C@@H]1[C@H](CC[C@@]2(C)O)C1(C)C

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10869197]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1812212]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18409045]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19245261]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	flower buds	n.a.	n.a.	PMID[19926279]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20151678]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	root	n.a.	PMID[2092947]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	berry	n.a.	n.a.	PMID[21216145]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	rhizome	n.a.	PMID[21563811]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[22671987]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23373216]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	leaves	n.a.	n.a.	PMID[24290061]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24968750]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25152999]
NPO18155	Salvia argentea	Species	Lamiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[25880372]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	stems-leaves	n.a.	n.a.	PMID[26420067]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26521454]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[27914541]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	Flower Buds	n.a.	n.a.	PMID[28345906]
NPO43334	Salvia chamelaeagnea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31958659]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32129622]
NPO48247	Helichrysum araxinum Takht. ex Kirp.	Genus	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32619198]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33780581]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35481430]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35872238]
NPO55948	Salvia dentata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235019]
NPO60267	Salvia africana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235019]
NPO43334	Salvia chamelaeagnea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36235019]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36270431]
NPO51049	Piper cordoncillo var. apazoteanum	Genus	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37103127]
NPO56463	Grindelia squarrosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37175263]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38163555]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38257257]
NPO53768	Salvia ringens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38611827]
NPO18155	Salvia argentea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38611827]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893531]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39104562]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	leaves	n.a.	n.a.	PMID[9834145]
NPO18155	Salvia argentea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18951	Ligusticum sinense	Species	Apiaceae	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]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22033	Cnidium officinale	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18951	Ligusticum sinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29016	Valeriana jatamansi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29141	Panax ginseng	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1859	Lantana camara	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18155	Salvia argentea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25682	Acorus calamus	Species	Acoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18951	Ligusticum sinense	Species	Apiaceae	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	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference
NPO18155	Salvia argentea	Oil	n.a.	0.8	n.a.	n.a.	%	PMID[38611827]
NPO18155	Salvia argentea	Oil	n.a.	1.2	n.a.	n.a.	%	PMID[38611827]
NPO1859	Lantana camara	Oil	n.a.	1.9	n.a.	n.a.	%	PMID[36270431]
NPO43334	Salvia chamelaeagnea	Oil	n.a.	0.00	n.a.	n.a.	%	PMID[36235019]
NPO43334	Salvia chamelaeagnea	Oil	n.a.	0.48	n.a.	n.a.	%	PMID[36235019]
NPO48247	Helichrysum araxinum Takht. ex Kirp.	Oil	n.a.	0.2Â±0.04	n.a.	n.a.	%	PMID[32619198]
NPO51049	Piper cordoncillo var. apazoteanum	Oil	n.a.	1.02	n.a.	n.a.	%	PMID[37103127]
NPO53768	Salvia ringens	Oil	n.a.	0.1	n.a.	n.a.	%	PMID[38611827]
NPO55948	Salvia dentata	Oil	n.a.	0.00	n.a.	n.a.	%	PMID[36235019]
NPO56463	Grindelia squarrosa	Oil	n.a.	0.1	n.a.	n.a.	%	PMID[37175263]
NPO60267	Salvia africana	Oil	n.a.	0.00	n.a.	n.a.	%	PMID[36235019]
NPO60267	Salvia africana	Oil	n.a.	0.10	n.a.	n.a.	%	PMID[36235019]
NPO60267	Salvia africana	Oil	n.a.	0.33	n.a.	n.a.	%	PMID[36235019]

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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC52394 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	34359
0.1-0.2	15006
0.2-0.3	444
0.3-0.4	32
0.4-0.5	13
0.5-0.6	2
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC152964
1.0	High Similarity	NPC127997
1.0	High Similarity	NPC95969
0.5882	Remote Similarity	NPC45387
0.5882	Remote Similarity	NPC64316

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC52394 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8267
0.1-0.2	852
0.2-0.3	31
0.3-0.4	0
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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