NPASS Compound

Natural Product: NPC105025

Natural Product ID	NPC105025
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hispiduloside
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms	Hispidulin-7-Glucoside; Hispiduloside
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL480657
PubChem CID	5318083
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 55 58 0 0 0 0 0 0 0 0999 V2000 1.9533 -4.0819 1.9737 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2819 -2.9622 2.5221 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2919 -2.2688 1.8766 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6633 -1.1927 1.0778 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3504 -0.5165 0.4431 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7033 -0.8650 0.5705 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0457 -1.9287 1.3626 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3779 -2.2628 1.4810 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7154 -3.2447 2.2099 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3464 -1.5317 0.8082 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9392 -0.4740 0.0277 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8728 0.3548 -0.7174 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4167 1.4044 -1.4863 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2693 2.2130 -2.2071 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6186 1.9896 -2.1770 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1092 0.9422 -1.4135 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2161 0.1310 -0.6864 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5342 2.7816 -2.8915 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6338 -0.1981 -0.0481 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0373 -2.6152 2.0048 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4290 -3.6913 2.8012 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9978 -0.8395 0.9448 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5296 0.1951 0.1955 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3278 1.0930 1.1538 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7966 2.2663 0.3303 C 0 0 2 0 0 0 0 0 0 0 0 0 4.1523 1.9538 -1.0699 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0741 0.5427 -1.5014 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5078 0.0500 -1.7546 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1588 0.9213 -2.6199 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4945 -0.3478 -0.6526 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2975 2.7037 -1.9142 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8833 2.8494 1.0054 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5637 1.5540 2.1950 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9792 -4.0495 0.8604 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5130 -5.0431 2.2771 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9998 -4.0825 2.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1166 0.3248 -0.1873 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3837 -1.7946 0.9026 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3307 1.5644 -1.4951 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8764 3.0171 -2.7914 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1649 0.7758 -1.3964 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6323 -0.6605 -0.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8739 3.5964 -2.4270 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9836 -4.5926 2.6096 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8359 0.8218 -0.3613 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2445 0.5446 1.4737 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9656 3.0265 0.3917 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1708 2.3949 -1.2879 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5741 0.4355 -2.4966 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4403 -0.9506 -2.2030 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0775 0.0149 -0.8024 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0442 1.2109 -2.2663 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4357 2.4389 -2.8597 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6896 3.7508 1.3218 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0327 2.3311 2.5908 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 15 18 1 0 11 19 1 0 7 20 2 0 20 21 1 0 4 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 27 30 1 0 26 31 1 0 25 32 1 0 24 33 1 0 20 3 1 0 30 23 1 0 19 6 1 0 17 12 1 0 1 34 1 0 1 35 1 0 1 36 1 0 5 37 1 0 10 38 1 0 13 39 1 0 14 40 1 0 16 41 1 0 17 42 1 0 18 43 1 0 21 44 1 0 23 45 1 6 24 46 1 1 25 47 1 6 26 48 1 6 27 49 1 6 28 50 1 0 28 51 1 0 29 52 1 0 31 53 1 0 32 54 1 0 33 55 1 0 M END

Standard InCHIKey	GCLAFEGUXXHIFT-IWLDQSELSA-N
Standard InCHI	InChI=1S/C22H22O11/c1-30-21-14(32-22-20(29)19(28)17(26)15(8-23)33-22)7-13-16(18(21)27)11(25)6-12(31-13)9-2-4-10(24)5-3-9/h2-7,15,17,19-20,22-24,26-29H,8H2,1H3/t15-,17-,19+,20-,22-/m1/s1
SMILES	COc1c(cc2c(c(=O)cc(c3ccc(cc3)O)o2)c1O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

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
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	Flowers	Tantempango, Hidalgo, Mexico	2019-May	DOI[10.1007/s11130-020-00822-2]
NPO40994	Inula britannica	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[10650074]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	Entire plants	the surroundings of Uppsala, Sweden	1998-SEP	PMID[11421736]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	Whole Plant	the surroundings of Uppsala, Sweden	1998-SEP	PMID[11421736]
NPO6987	Tolypothrix byssoidea	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11429991]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11858748]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880314]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1294695]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1367520]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104516]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974609]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16297615]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	leaves and twigs	Taiwan	n.a.	PMID[1659612]
NPO23838	Kitasatospora kifunensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17191679]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18543151]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19093848]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	bulb	n.a.	PMID[19093848]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21381678]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21667925]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22118684]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24358188]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	PMID[24669201]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24840014]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2488968]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[24895551]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	aerial parts	Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China	2012-OCT	PMID[24955889]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	seed	n.a.	PMID[2610694]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26692349]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27933899]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28960981]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	Stems	n.a.	n.a.	PMID[31180680]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33089690]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8626236]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778246]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9784154]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8231	Jaspis digonoxea	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15621	Lethasterias fusca	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11437	Alluaudia ascendens	Species	Didiereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6987	Tolypothrix byssoidea	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO228	Physostigma venenosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5788	Millingtonia hortensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO228	Physostigma venenosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5788	Millingtonia hortensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO228	Physostigma venenosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5788	Millingtonia hortensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23838	Kitasatospora kifunensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22203	Tapinella panuoides	Species	Tapinellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13225	Spergula japonica	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO255	Solanum pseudopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16161	Stephania aculeata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15087	Alstonia pittieri	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28240	Notholaena lemmonii	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13010	Allium stipitatum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10031	Euphorbia antiquorum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14614	Kopsia longiflora	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14454	Plectranthus lanuginosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11584	Artemisia argentea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2667	Acacia lasiopetala	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27134	Euphrasia rubra	Species	Orobanchaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8556	Eucalyptus kitsoniana	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4214	Centaurea collina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5995	Spartium junceum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10527	Cyathula tomentosa	Species	Amaranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8231	Jaspis digonoxea	Species	Ancorinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26381	Bombus pascuorum	Species	Apidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15513	Pseudocyphellaria rubella	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15806	Rhododendron campylocarpum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3477	Plantago asiatica	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1777	Toddalia aculeata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9299.3	Hordeum vulgare var. distichon	Varieties	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15718	Lindera sericea	Species	Tineidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1124	Scapania aequiloba	Species	Scapaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5137	Myristica malabarica	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15108	Angiopteris evecta	Species	Marattiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13460	Asphodeline damascena	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11697	Cirsium setosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16076	Penicillium chrysogenum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9917	Plagiomnium cuspidatum	Species	Mniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27031	Methanosarcina barkeri	Species	Methanosarcinaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO15898	Streptomyces noursei	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5788	Millingtonia hortensis	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22101	Himantoglossum hircinum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15404	Streptomyces erythrochromogenes	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10196	Echinocereus blanckii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26951	Gymnopus androsaceus	Species	Omphalotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4489	Achillea serbica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13743	Populus yunnanensis	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11189	Anabaena sphaerica	Species	Nostocaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8719	Fusarium vasinfectum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10826	Rabdosia weisiensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO228	Physostigma venenosum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11243	Exochorda giraldii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14327	Scabiosa comosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12777	Laurencia pacifica	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6710	Sinapis nigra	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5445	Euonymus nanus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12480	Brodiaea californica	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21851	Chaetomella raphigera	Species	Chaetomellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14965	Lepidophorum repandum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29322	Rhodanthe maryonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6987	Tolypothrix byssoidea	Species	Tolypothrichaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11437	Alluaudia ascendens	Species	Didiereaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15621	Lethasterias fusca	Species	Asteriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21324	Plantago major	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11578	Aloe vera	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17346	Salvia plebeia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	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
EC50	1
IC50	2

Activity Type	# Activity
Individual protein	1
Cell line	1
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1618	Individual protein	Peroxisome proliferator-activated receptor gamma	Mus musculus	EC50	>	100000.0	nM	PMID[24955889]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	>	50.0	ug.mL-1	PMID[10650074]
NPT1	Others	Radical scavenging activity	n.a.	IC50	>	100.0	ug.mL-1	PMID[10650074]

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 NPC105025 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	21019
0.1-0.2	24537
0.2-0.3	2793
0.3-0.4	980
0.4-0.5	361
0.5-0.6	106
0.6-0.7	33
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9265	High Similarity	NPC93337
0.8732	High Similarity	NPC201292
0.8592	High Similarity	NPC186807
0.8378	Intermediate Similarity	NPC602805
0.831	Intermediate Similarity	NPC58053
0.8082	Intermediate Similarity	NPC45638
0.7867	Intermediate Similarity	NPC609451
0.7568	Intermediate Similarity	NPC39360
0.7568	Intermediate Similarity	NPC29763
0.7568	Intermediate Similarity	NPC210003
0.7532	Intermediate Similarity	NPC605067
0.7467	Intermediate Similarity	NPC146792
0.7368	Intermediate Similarity	NPC24043
0.7143	Intermediate Similarity	NPC610763
0.7051	Intermediate Similarity	NPC117260
0.7037	Intermediate Similarity	NPC172807
0.6962	Remote Similarity	NPC488071
0.6795	Remote Similarity	NPC95090
0.6795	Remote Similarity	NPC27408
0.6795	Remote Similarity	NPC259152
0.6716	Remote Similarity	NPC120163
0.6707	Remote Similarity	NPC488072
0.6667	Remote Similarity	NPC83283
0.6627	Remote Similarity	NPC211594
0.6625	Remote Similarity	NPC205076
0.6585	Remote Similarity	NPC311830
0.6585	Remote Similarity	NPC607707
0.6582	Remote Similarity	NPC189142
0.6582	Remote Similarity	NPC77660
0.65	Remote Similarity	NPC58716
0.65	Remote Similarity	NPC603655
0.6463	Remote Similarity	NPC243930
0.6463	Remote Similarity	NPC21666
0.6456	Remote Similarity	NPC261866
0.6456	Remote Similarity	NPC45618
0.6456	Remote Similarity	NPC143851
0.6386	Remote Similarity	NPC88023
0.6386	Remote Similarity	NPC309025
0.6329	Remote Similarity	NPC331652
0.6265	Remote Similarity	NPC22832
0.6265	Remote Similarity	NPC601144
0.625	Remote Similarity	NPC204693
0.622	Remote Similarity	NPC27942
0.6173	Remote Similarity	NPC168822
0.6163	Remote Similarity	NPC254540
0.6098	Remote Similarity	NPC488080
0.6098	Remote Similarity	NPC169977
0.6071	Remote Similarity	NPC601710
0.6044	Remote Similarity	NPC483707
0.5977	Remote Similarity	NPC473682
0.5977	Remote Similarity	NPC472607
0.5976	Remote Similarity	NPC297987
0.5976	Remote Similarity	NPC323593
0.5976	Remote Similarity	NPC203500
0.5904	Remote Similarity	NPC84265
0.5882	Remote Similarity	NPC284960
0.5854	Remote Similarity	NPC110349
0.5783	Remote Similarity	NPC105511
0.5778	Remote Similarity	NPC607513
0.5765	Remote Similarity	NPC191306
0.5765	Remote Similarity	NPC224462
0.5747	Remote Similarity	NPC48773
0.5714	Remote Similarity	NPC84362
0.5714	Remote Similarity	NPC10807
0.5714	Remote Similarity	NPC161881
0.5694	Remote Similarity	NPC25270
0.5663	Remote Similarity	NPC77672
0.5663	Remote Similarity	NPC133671
0.5663	Remote Similarity	NPC135391
0.5663	Remote Similarity	NPC78263
0.5663	Remote Similarity	NPC250069
0.5647	Remote Similarity	NPC222936
0.5647	Remote Similarity	NPC182045
0.5634	Remote Similarity	NPC239128
0.5632	Remote Similarity	NPC307518
0.5632	Remote Similarity	NPC116458
0.5632	Remote Similarity	NPC246943
0.5604	Remote Similarity	NPC65003
0.5581	Remote Similarity	NPC168584
0.5556	Remote Similarity	NPC145379
0.5556	Remote Similarity	NPC603300
0.5532	Remote Similarity	NPC150767
0.5529	Remote Similarity	NPC27640
0.5529	Remote Similarity	NPC181712
0.5495	Remote Similarity	NPC44931
0.5476	Remote Similarity	NPC19709
0.5467	Remote Similarity	NPC47781
0.5465	Remote Similarity	NPC198324
0.5465	Remote Similarity	NPC42773
0.5465	Remote Similarity	NPC45522
0.5435	Remote Similarity	NPC3583
0.5412	Remote Similarity	NPC8573
0.5412	Remote Similarity	NPC277205
0.5412	Remote Similarity	NPC37919
0.5412	Remote Similarity	NPC136042
0.5393	Remote Similarity	NPC469931
0.5393	Remote Similarity	NPC601586
0.5368	Remote Similarity	NPC124155
0.5349	Remote Similarity	NPC245014
0.5341	Remote Similarity	NPC101026
0.5341	Remote Similarity	NPC488077
0.5319	Remote Similarity	NPC64051
0.5294	Remote Similarity	NPC289667
0.5287	Remote Similarity	NPC599850
0.5278	Remote Similarity	NPC75279
0.5278	Remote Similarity	NPC607196
0.5275	Remote Similarity	NPC8856
0.5269	Remote Similarity	NPC473512
0.5269	Remote Similarity	NPC233994
0.5269	Remote Similarity	NPC129827
0.5233	Remote Similarity	NPC145038
0.5233	Remote Similarity	NPC56077
0.5233	Remote Similarity	NPC281131
0.5233	Remote Similarity	NPC253662
0.5233	Remote Similarity	NPC161749
0.5233	Remote Similarity	NPC179950
0.5233	Remote Similarity	NPC88789
0.5233	Remote Similarity	NPC491374
0.5227	Remote Similarity	NPC307938
0.5222	Remote Similarity	NPC203050
0.5222	Remote Similarity	NPC225434
0.5205	Remote Similarity	NPC241498
0.52	Remote Similarity	NPC69394
0.5176	Remote Similarity	NPC473043
0.5172	Remote Similarity	NPC46420
0.5169	Remote Similarity	NPC486578
0.5158	Remote Similarity	NPC64425
0.5155	Remote Similarity	NPC270675
0.5155	Remote Similarity	NPC195685
0.514	Remote Similarity	NPC488079
0.514	Remote Similarity	NPC488078
0.5135	Remote Similarity	NPC198826
0.5135	Remote Similarity	NPC234133
0.5135	Remote Similarity	NPC276409
0.5132	Remote Similarity	NPC160951
0.5114	Remote Similarity	NPC472459
0.5114	Remote Similarity	NPC100720
0.5111	Remote Similarity	NPC206123
0.5111	Remote Similarity	NPC605784
0.5104	Remote Similarity	NPC211532
0.5104	Remote Similarity	NPC483415
0.5104	Remote Similarity	NPC488364
0.5102	Remote Similarity	NPC475382
0.5098	Remote Similarity	NPC472993
0.5067	Remote Similarity	NPC78913
0.5057	Remote Similarity	NPC197896
0.5057	Remote Similarity	NPC64305
0.5057	Remote Similarity	NPC313163
0.5057	Remote Similarity	NPC609879
0.5056	Remote Similarity	NPC282169
0.5055	Remote Similarity	NPC190003
0.5053	Remote Similarity	NPC122809
0.5052	Remote Similarity	NPC483416
0.5051	Remote Similarity	NPC101636
0.5051	Remote Similarity	NPC298171

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC105025 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5381
0.1-0.2	3665
0.2-0.3	87
0.3-0.4	9
0.4-0.5	7
0.5-0.6	1
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
0.5233	Remote Similarity	NPD4381	Clinical (unspecified phase)

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