NPASS Compound

Natural Product: NPC195713

Natural Product ID	NPC195713
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Alpha-Terthienyl
IUPAC Name	2,5-dithiophen-2-ylthiophene
Synonyms	Alpha-Terthienyl
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL90017
PubChem CID	65067
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0002021] Bi- and oligothiophenes

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 23 25 0 0 0 0 0 0 0 0999 V2000 4.8158 0.0670 -1.0628 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3572 0.8902 -0.1147 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8995 1.3764 0.8605 S 0 0 0 0 0 0 0 0 0 0 0 0 2.7438 0.4226 -0.1145 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5005 -0.1646 -1.0579 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3032 0.3525 0.1304 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5737 0.9745 1.1129 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7468 0.7577 1.1383 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3064 -0.0533 0.2103 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1129 -0.5445 -0.7625 S 0 0 0 0 0 0 0 0 0 0 0 0 -2.6638 -0.4721 -0.0193 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8288 -0.2156 0.5878 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9594 -0.7722 0.1253 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8796 -1.6058 -0.9816 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1024 -1.6066 -1.3978 S 0 0 0 0 0 0 0 0 0 0 0 0 5.5048 -0.3878 -1.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3787 1.2290 0.0890 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9931 -0.8334 -1.8124 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1374 1.6274 1.8335 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3968 1.2317 1.9090 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8187 0.4769 1.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9717 -0.5849 0.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6462 -2.1650 -1.5325 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 2 0 4 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 5 1 1 0 10 6 1 0 15 11 1 0 1 16 1 0 2 17 1 0 5 18 1 0 7 19 1 0 8 20 1 0 12 21 1 0 13 22 1 0 14 23 1 0 M END

Standard InCHIKey	KXSFECAJUBPPFE-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C12H8S3/c1-3-9(13-7-1)11-5-6-12(15-11)10-4-2-8-14-10/h1-8H
SMILES	c1csc(c1)c1ccc(s1)c1cccs1

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
NPO12666	Trachycarpus fortunei	Species	Arecaceae	Eukaryota	n.a.	Serdang, Selangor, Malaysia	n.a.	DOI[10.1002/ejlt.201000369]
NPO12666	Trachycarpus fortunei	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO12666	Trachycarpus fortunei	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/jf950732o]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[11141122]
NPO21382	Eutypa lata	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12608846]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO2842	Garcinia lucida	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17880175]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO12666	Trachycarpus fortunei	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21081239]
NPO23021	Solanum congestiflorum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21905650]
NPO1672	Apostichopus japonicus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	PMID[22700234]
NPO16507	Carpesium lipskyi	Species	Asteraceae	Eukaryota	Whole Plants	n.a.	n.a.	PMID[30869892]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39181940]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39716808]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20606	Piper tuberculatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3608	Eleutherococcus giraldii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19272	Alcyonium fauri	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18882	Chondrococcus hornemannii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21011	Ormosia amazonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21183	Peziza mollissima	Species	Pezizaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23021	Solanum congestiflorum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10392	Strychnos soubrensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20431	Centaurea canariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9110	Artemisia deserti	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16507	Carpesium lipskyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16579	Dracocephalum rupestre	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16619	Paraphyton cookei	Species	Arthrodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14371	Rhinanthus angustifolius	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6537	Termes princeps	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12666	Trachycarpus fortunei	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18678	Actinomadura pelletieri	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1672	Apostichopus japonicus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18266	Microsphaeropsis olivacea	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19410	Clutia abyssinica	Species	Peraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17639	Stevia achalensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18931	Buellia canescens	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17904	Cassia renigera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19837	Euonymus latifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21251	Tabernaemontana odoratissima	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26309	Ahnfeltiopsis flabelliformis	Species	Phyllophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18770	Euphausia pacifica	Species	Euphausiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21382	Eutypa lata	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15546	Herba ecliptae prostratae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20606	Piper tuberculatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16579	Dracocephalum rupestre	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12666	Trachycarpus fortunei	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15546	Herba ecliptae prostratae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3608	Eleutherococcus giraldii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16579	Dracocephalum rupestre	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12666	Trachycarpus fortunei	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1672	Apostichopus japonicus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20606	Piper tuberculatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22699	Echinops setifer	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4163	Echinopsis latifolius	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12666	Trachycarpus fortunei	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9110	Artemisia deserti	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19837	Euonymus latifolius	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20101	Eria acutifolia	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17908	Rhododendron reticulatum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17639	Stevia achalensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26309	Ahnfeltiopsis flabelliformis	Species	Phyllophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19559	Cetraria pseudocomplicata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20295	Eclipta prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3608	Eleutherococcus giraldii	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14172	Rhopaloeides odorabile	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18749	Corydalis vernyi	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11034	Mnium pseudopunctatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21183	Peziza mollissima	Species	Pezizaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20606	Piper tuberculatum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22210	Allium ampeloprasum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21251	Tabernaemontana odoratissima	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19272	Alcyonium fauri	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20648	Streptomyces cellulosae	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14371	Rhinanthus angustifolius	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20718	Hypericum elegans	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20431	Centaurea canariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1672	Apostichopus japonicus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17115	Kielmeyera petiolaris	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2842	Garcinia lucida	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17357	Bactrocera kraussi	Species	Tephritidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18266	Microsphaeropsis olivacea	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18931	Buellia canescens	Species	Caliciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16507	Carpesium lipskyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16619	Paraphyton cookei	Species	Arthrodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20233	Marchantia paleacea	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20982	Morus lactea	Species	Sulidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17904	Cassia renigera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21382	Eutypa lata	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3468	Astragalus floccosifolius	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6537	Termes princeps	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18882	Chondrococcus hornemannii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12666	Trachycarpus fortunei	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23021	Solanum congestiflorum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4597	Campanula lactiflora	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10392	Strychnos soubrensis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21011	Ormosia amazonica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21507	Ephedra intermedia	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18770	Euphausia pacifica	Species	Euphausiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17962	Tagetes erecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19410	Clutia abyssinica	Species	Peraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18678	Actinomadura pelletieri	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO16579	Dracocephalum rupestre	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28696	Rhaponticum uniflorum	Species	Asteraceae	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

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
Potency	40
IC50	15
GI	3
mortality	8

Activity Type	# Activity
Individual protein	10
Organism	25
Others	31

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	17228.9	nM	PubChem BioAssay data set
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	2730.6	nM	PubChem BioAssay data set
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	43641.2	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	6916.7	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT162	Individual protein	Heat shock protein beta-1	Homo sapiens	Potency	n.a.	27535.7	nM	PubChem BioAssay data set
NPT106	Individual protein	Peroxisome proliferator-activated receptor delta	Homo sapiens	Potency	n.a.	61644.8	nM	PubChem BioAssay data set
NPT163	Individual protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT74	Individual protein	Proto-oncogene c-JUN	Homo sapiens	Potency	n.a.	61644.8	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT635	Organism	Botryotinia fuckeliana	Botryotinia fuckeliana	IC50	>	50000.0	nM	PMID[16506815]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	25.0	%	PMID[16506815]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	GI	=	98.0	%	PMID[16506815]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	IC50	>	50000.0	nM	PMID[16506815]
NPT852	Organism	Phomopsis obscurans	Phomopsis obscurans	IC50	=	9600.0	nM	PMID[16506815]
NPT851	Organism	Colletotrichum fragariae	Colletotrichum fragariae	IC50	=	9000.0	nM	PMID[16506815]
NPT1096	Organism	Colletotrichum acutatum	Colletotrichum acutatum	IC50	=	5300.0	nM	PMID[16506815]
NPT637	Organism	Fusarium oxysporum	Fusarium oxysporum	IC50	=	5000.0	nM	PMID[16506815]
NPT852	Organism	Phomopsis obscurans	Phomopsis obscurans	IC50	=	7200.0	nM	PMID[16506815]
NPT851	Organism	Colletotrichum fragariae	Colletotrichum fragariae	IC50	=	4900.0	nM	PMID[16506815]
NPT1096	Organism	Colletotrichum acutatum	Colletotrichum acutatum	IC50	=	3000.0	nM	PMID[16506815]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	27306	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	34673.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	34376.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	27535.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43277.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	61130.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	21872.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24336.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	24541.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	19331.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	68589.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54941	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3857.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	48557.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	30637.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	54482.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1722.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	48966.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	863.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3437.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	10000.0	nM	PMID[9873605]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	GI	=	98.0	%	PMID[16506815]
NPT1095	Organism	Plasmopara viticola	Plasmopara viticola	IC50	<	6300.0	nM	PMID[16506815]
NPT562	Organism	Colletotrichum gloeosporioides	Colletotrichum gloeosporioides	IC50	<	1600.0	nM	PMID[16506815]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT22576	Organism	Heterodera zeae	Heterodera zeae	mortality	=	100.0	%	PMID[21780738]

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 NPC195713 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	48684
0.1-0.2	1079
0.2-0.3	77
0.3-0.4	11
0.4-0.5	4
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	0

Similarity Score	Similarity Level	Natural Product ID
0.5667	Remote Similarity	NPC24122
0.5667	Remote Similarity	NPC173019

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC195713 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8530
0.1-0.2	604
0.2-0.3	15
0.3-0.4	1
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