NPASS Compound

Natural Product: NPC275780

Natural Product ID	NPC275780
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Mangostanin
IUPAC Name	5,9-dihydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
Synonyms	9-Hydroxycalabaxanthone; Mangostanin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL561643
PubChem CID	5495929
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes [CHEMONTID:0000204] Xanthones [CHEMONTID:0003519] 8-prenylated xanthones

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 54 57 0 0 0 0 0 0 0 0999 V2000 -5.4284 -2.9090 -0.0642 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3854 -2.8359 -0.9579 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0455 -2.7035 -0.7818 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2699 -3.8319 -0.6168 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8661 -5.1137 -0.6238 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9226 -3.6908 -0.4476 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3336 -2.4443 -0.4398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1166 -1.2805 -0.6071 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4680 -1.4232 -0.7760 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3465 -0.2382 -0.9198 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9856 0.1994 0.3167 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1314 1.4376 0.6875 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8100 1.7814 2.0036 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6975 2.5793 -0.1571 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4850 -0.0647 -0.5926 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1275 0.9924 -0.7364 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9030 -0.0271 -0.4131 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6130 -1.1993 -0.2544 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9656 -2.3308 -0.2760 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9862 -1.1613 -0.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6511 0.0484 -0.0564 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9253 1.2198 -0.2168 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5454 1.1782 -0.3959 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7914 2.3312 -0.5595 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6280 2.4877 -0.1865 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9295 2.5185 -0.0084 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7372 1.2964 0.1686 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0231 0.1048 0.1201 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8155 1.2466 -0.9135 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4704 1.3500 1.5119 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0596 -1.9831 -0.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1069 -3.7721 -0.1988 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0143 -2.8812 0.9777 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8339 -5.6946 0.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2904 -4.5709 -0.3151 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2439 -0.6822 -1.5168 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0202 0.5226 -1.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3626 -0.5698 0.9938 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3994 2.6843 1.8498 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0408 1.9705 2.7751 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4929 0.9677 2.3101 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4599 3.3835 -0.0153 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7174 2.3603 -1.2426 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7270 3.0098 0.1808 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5754 -2.0520 0.0504 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8892 3.0569 0.1345 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0753 3.4205 -0.3123 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4533 3.4766 0.0129 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8932 0.2347 -1.3542 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8135 1.4936 -0.4821 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 1.9869 -1.7034 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7556 1.1272 2.3300 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3008 0.6173 1.4844 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8610 2.3755 1.6089 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 4 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 11 12 2 3 12 13 1 0 12 14 1 0 8 15 1 0 15 16 2 0 15 17 1 0 17 18 2 0 18 19 1 0 18 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 22 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 27 29 1 0 27 30 1 0 9 3 1 0 23 17 1 0 19 7 1 0 28 21 1 0 1 31 1 0 1 32 1 0 1 33 1 0 5 34 1 0 6 35 1 0 10 36 1 0 10 37 1 0 11 38 1 0 13 39 1 0 13 40 1 0 13 41 1 0 14 42 1 0 14 43 1 0 14 44 1 0 20 45 1 0 24 46 1 0 25 47 1 0 26 48 1 0 29 49 1 0 29 50 1 0 29 51 1 0 30 52 1 0 30 53 1 0 30 54 1 0 M END

Standard InCHIKey	HQWHKELJHUFLGD-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C24H24O6/c1-12(2)6-7-14-19-17(10-15(25)23(14)28-5)29-18-11-16-13(8-9-24(3,4)30-16)21(26)20(18)22(19)27/h6,8-11,25-26H,7H2,1-5H3
SMILES	COc1c(O)cc2c(c1CC=C(C)C)c(=O)c1c(o2)cc2c(c1O)C=CC(O2)(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
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4039(00)90246-6]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1071/CH03175]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075773]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933891]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18464091]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558747]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19296616]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	stem bark	Pangradin village, Jasinga, West Java, Indonesia	2005-AUG	PMID[19839614]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	twigs	n.a.	n.a.	PMID[20058933]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20817450]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	pericarp	n.a.	PMID[24555285]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24717154]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	young fruits	Khokkhon, Tha Bo District, Nong Khai Province, Thailand	2011-Aug	PMID[25651042]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	flowers	Pakook, Muang District, Chiang Rai Province, Thailand	2013-Feb	PMID[25651042]
NPO40853	Garcinia tetrandra	Species	Clusiaceae	Eukaryota	Stem Bark	n.a.	n.a.	PMID[30978023]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31860303]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	fruit hulls	Madras, Tamil Nadu, India	1993-MAR	PMID[9213587]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40853	Garcinia tetrandra	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8560	Aplidium tabascum	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27924	Serpocaulon triseriale	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3806	Garcinia morella	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3449	Lonicera hypoleuca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12600	Trametes cinnabarina	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8354	Aster bellidiastrum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10376	Arcyria denudata	Species	Trichiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4064	Halimodendron halodendron	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10391	Dolomiaea souliei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10056	Nicotiana sylvestris	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6249	Garcinia mangostana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3707	Chromatium okenii	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9741	Actinopyga agassizi	Species	Holothuriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10221	Streptomyces alboniger	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO7920	Pentadesma butyracea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7534	Leptogorgia sarmentosa	Species	Gorgoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24931	Myelochroa aurulenta	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25472	Garcinia cowa	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10849	Eucalyptus camaldulensis	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8927	Poria selecta	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7811	Scleronephthya pallida	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25216	Senecio vellereus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9717	Wibelia divaricata	Species	Davalliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8560	Aplidium tabascum	Species	Polyclinidae	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
IC50	22
FC	1
Ki	1
Activity	3
Ratio IC50	1
ED50	1
Inhibition	1
MIC	6

Activity Type	# Activity
Individual protein	11
Cell line	12
Organism	8
Protein family	1
Others	3
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	IC50	>	20000.0	nM	PMID[19839614]
NPT344	Individual protein	Sialidase	Clostridium perfringens	IC50	=	20100.0	nM	PMID[20696581]
NPT344	Individual protein	Sialidase	Clostridium perfringens	Ki	=	5900.0	nM	PMID[20696581]
NPT1464	Individual protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	420.0	nM	PMID[32115956]
NPT1464	Individual protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	420.0	nM	PMID[34520193]
NPT1464	Individual protein	Phosphodiesterase 4D	Homo sapiens	IC50	=	420.0	nM	PMID[35985255]
NPT3892	Individual protein	Tumor necrosis factor receptor superfamily member 10B	Homo sapiens	FC	=	4.0	n.a.	PMID[19788289]
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	98.7	%	PMID[26508549]
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Activity	=	108.7	%	PMID[26508549]
NPT721	Individual protein	Nuclear factor NF-kappa-B p65 subunit	Homo sapiens	IC50	>	20000.0	nM	PMID[19839614]
NPT865	Individual protein	Fatty acid synthase	Homo sapiens	IC50	=	40640.0	nM	PMID[20817450]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	3.9	ug.mL-1	PMID[19296616]
NPT139	Cell line	HT-29	Homo sapiens	ED50	=	9.1	uM	PMID[19839614]
NPT397	Cell line	NCI-H460	Homo sapiens	IC50	=	19690.0	nM	PMID[24717154]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	=	21060.0	nM	PMID[24717154]
NPT2297	Cell line	ASPC1	Homo sapiens	IC50	=	25490.0	nM	PMID[24717154]
NPT323	Cell line	SW-620	Homo sapiens	IC50	=	26140.0	nM	PMID[24717154]
NPT139	Cell line	HT-29	Homo sapiens	IC50	=	1600.0	nM	PMID[30978023]
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	3400.0	nM	PMID[30978023]
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	1900.0	nM	PMID[30978023]
NPT91	Cell line	KB	Homo sapiens	IC50	=	1700.0	nM	PMID[30978023]
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	18600.0	nM	PMID[31860303]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	IC50	>	1.9	ug.mL-1	PMID[19296616]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	MIC	=	128.0	ug.mL-1	PMID[25651042]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	26170.0	nM	PMID[24717154]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	8.0	ug.mL-1	PMID[25651042]
NPT20987	Cell line	HeLa S3	Homo sapiens	IC50	=	1900.0	nM	PMID[30978023]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	64.0	ug.mL-1	PMID[25651042]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[25651042]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	=	128.0	ug.mL-1	PMID[25651042]
NPT20648	Protein family	Alpha glucosidase	Homo sapiens	IC50	=	11400.0	nM	PMID[31860303]
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	2.05	n.a.	PMID[19296616]
NPT2	Others	Unspecified	n.a.	Inhibition	=	70.1	%	PMID[25651042]
NPT2	Others	Unspecified	n.a.	IC50	=	34600.0	nM	PMID[25651042]
NPT314	Organism	Bacillus cereus	Bacillus cereus	MIC	=	4.0	ug.mL-1	PMID[25651042]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	n.a.	n.a.	n.a.	PMID[36634312]

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference
Rattus norvegicus	Liver	T1/2	=	0.135	hr	PMID[35985255]

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 NPC275780 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	23340
0.1-0.2	22098
0.2-0.3	3791
0.3-0.4	477
0.4-0.5	84
0.5-0.6	40
0.6-0.7	15
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8472	Intermediate Similarity	NPC39091
0.7826	Intermediate Similarity	NPC229632
0.7313	Intermediate Similarity	NPC14353
0.726	Intermediate Similarity	NPC239752
0.7222	Intermediate Similarity	NPC472450
0.7143	Intermediate Similarity	NPC472449
0.6986	Remote Similarity	NPC236521
0.6892	Remote Similarity	NPC83922
0.6892	Remote Similarity	NPC117854
0.6849	Remote Similarity	NPC178964
0.6757	Remote Similarity	NPC207690
0.6571	Remote Similarity	NPC228785
0.6533	Remote Similarity	NPC471973
0.6447	Remote Similarity	NPC170245
0.6341	Remote Similarity	NPC479156
0.6316	Remote Similarity	NPC152659
0.625	Remote Similarity	NPC166054
0.6197	Remote Similarity	NPC241904
0.6184	Remote Similarity	NPC189473
0.6027	Remote Similarity	NPC479166
0.6	Remote Similarity	NPC70272
0.5976	Remote Similarity	NPC479157
0.5974	Remote Similarity	NPC310349
0.5867	Remote Similarity	NPC479165
0.5811	Remote Similarity	NPC101957
0.5789	Remote Similarity	NPC16492
0.575	Remote Similarity	NPC40491
0.575	Remote Similarity	NPC278052
0.5733	Remote Similarity	NPC479160
0.5698	Remote Similarity	NPC150977
0.5679	Remote Similarity	NPC472448
0.56	Remote Similarity	NPC604618
0.5584	Remote Similarity	NPC220313
0.557	Remote Similarity	NPC248638
0.557	Remote Similarity	NPC61010
0.5541	Remote Similarity	NPC165977
0.5526	Remote Similarity	NPC6633
0.5526	Remote Similarity	NPC200246
0.55	Remote Similarity	NPC210446
0.5443	Remote Similarity	NPC25152
0.5432	Remote Similarity	NPC6588
0.5417	Remote Similarity	NPC473076
0.5375	Remote Similarity	NPC23298
0.5325	Remote Similarity	NPC146134
0.5309	Remote Similarity	NPC300727
0.5256	Remote Similarity	NPC474186
0.5256	Remote Similarity	NPC475886
0.5238	Remote Similarity	NPC78803
0.5233	Remote Similarity	NPC7483
0.5233	Remote Similarity	NPC74766
0.52	Remote Similarity	NPC255133
0.5176	Remote Similarity	NPC479155
0.5128	Remote Similarity	NPC65491
0.5125	Remote Similarity	NPC474350
0.5122	Remote Similarity	NPC184755
0.5065	Remote Similarity	NPC139036
0.5065	Remote Similarity	NPC56085
0.5065	Remote Similarity	NPC602307
0.506	Remote Similarity	NPC37870
0.5059	Remote Similarity	NPC206153
0.5059	Remote Similarity	NPC271629

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC275780 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3607
0.1-0.2	5473
0.2-0.3	69
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