NPASS Compound

Natural Product: NPC190457

Natural Product ID	NPC190457
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Omega-Hydroxyemodin
IUPAC Name	1,3,8-trihydroxy-6-(hydroxymethyl)anthracene-9,10-dione
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL290932
PubChem CID	361512
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000018] Anthracenes [CHEMONTID:0000151] Anthraquinones [CHEMONTID:0001598] Hydroxyanthraquinones

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 31 33 0 0 0 0 0 0 0 0999 V2000 5.0100 1.3214 0.8607 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6863 0.1408 0.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2433 0.2111 -0.2095 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9071 0.7555 -1.4386 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5651 0.8109 -1.7862 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1974 1.3508 -3.0110 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5942 0.3341 -0.9250 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9269 -0.2082 0.2990 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2663 -0.2593 0.6371 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0767 -0.7180 1.2258 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2315 -1.2134 2.3448 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4994 -0.6719 0.8845 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8303 -0.1294 -0.3397 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8210 0.3835 -1.2721 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1654 0.8775 -2.3941 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1729 -0.0869 -0.6595 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4905 0.4670 -1.9060 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1383 -0.5637 0.2028 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8077 -1.1067 1.4280 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4679 -1.1524 1.7544 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7678 -1.5912 2.3078 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5714 1.2752 1.7444 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3000 0.1424 -0.7422 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8731 -0.7603 0.8047 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6521 1.1360 -2.1310 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6408 2.1779 -3.1209 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5035 -0.6941 1.6135 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4035 0.8385 -2.0221 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1872 -0.5185 -0.0729 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1795 -1.5710 2.7044 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1610 -0.9775 3.0316 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 1 0 5 7 2 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 10 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 13 16 1 0 16 17 1 0 16 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 9 3 1 0 20 12 1 0 14 7 1 0 1 22 1 0 2 23 1 0 2 24 1 0 4 25 1 0 6 26 1 0 9 27 1 0 17 28 1 0 18 29 1 0 20 30 1 0 21 31 1 0 M END

Standard InCHIKey	YQHZABGPIPECSQ-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C15H10O6/c16-5-6-1-8-12(10(18)2-6)15(21)13-9(14(8)20)3-7(17)4-11(13)19/h1-4,16-19H,5H2
SMILES	OCc1cc(O)c2c(c1)C(=O)c1c(C2=O)c(O)cc(c1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	286.05	Volume:	273.977 ? Van der Waals volume.
Dense:	1.044	LogP:	2.71 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.475 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.179 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	18.0
TPSA:	115.06 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	3.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.532	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.517	Fsp³:	0.067
MCE-18:	38.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	1
Colloidal aggregators:	0.343	Fluc inhibitor:	0.435 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.154 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.356 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.483	Promiscuous compounds:	0.728

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.41	MDCK Permeability:	-4.771
Pgp-inhibitor:	0.007	Pgp-substrate:	0.023
PAMPA:	0.96 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.107
20% Bioavailability (F20%):	0.146	30% Bioavailability (F30%):	0.954
50% Bioavailability (F50%):	0.961

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.722
Plasma Protein Binding (PPB):	91.582%	Volume Distribution (VD):	0.911
Fu:	10.279% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.703
OATP1B3 inhibitor:	0.986	BCRP inhibitor:	0.173
BSEP inhibitor:	0.04

ADMET: Metabolism

CYP1A2-inhibitor:	0.724	CYP1A2-substrate:	0.282
CYP2C19-inhibitor:	0.994	CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.011
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.021
CYP3A4-inhibitor:	0.006	CYP3A4-substrate:	0.021
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.907 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

3.102

Half-life (T1/2):

1.674

ADMET: Toxicity

hERG Blockers:	0.028	hERG Blockers (10um):	0.392
Human Hepatotoxicity (H-HT):	0.693	Drug-induced Liver Injury (DILI):	0.874
AMES Toxicity:	0.924	Rat Oral Acute Toxicity:	0.368
Maximum Recommended Daily Dose:	0.504	Skin Sensitization:	0.883
Carcinogencity:	0.825	Eye Corrosion:	0.0
Eye Irritation:	0.982	Respiratory Toxicity:	0.87
Drug-induced Neurotoxicity:	0.208	Ototoxicity:	0.454
Hematotoxicity:	0.606	Drug-induced Nephrotoxicity:	0.601
Genotoxicity:	0.996	RPMI-8226 Immunitoxicity:	0.342
A549 Cytotoxicity:	0.883	Hek293 Cytotoxicity:	0.623
BCF:	1.261 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.589 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.671 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.896 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1021/jo00051a050]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11076555]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[11454355]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[11459643]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1517743]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	root	n.a.	PMID[16564530]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19658431]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19719093]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22512738]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23157012]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	roots	n.a.	n.a.	PMID[24499304]
NPO472	Penicillium restrictum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24911880]
NPO26465	Coreopsis tinctoria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25516207]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	Aerial Parts	n.a.	n.a.	PMID[28581290]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[29359942]
NPO40155	Helotiales sp.	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	PMID[30730742]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots	n.a.	n.a.	PMID[31944695]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	Roots; Tubers	n.a.	n.a.	PMID[7714535]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8277318]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7317.1	Citrus aurantium var. amara	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26401	Andrographis neesiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26465	Coreopsis tinctoria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13716	Aconitum tasiromontanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14217	Adansonia grandidieri	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14412	Aphyllocladus denticulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2631	Aster sedifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4345	Caulocystis cephalornithos	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16590	Cytophaga hutchinsoni	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14104	Dendriopoterium menendezii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9448	Dictyopteris australis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8386	Enceliopsis argophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11749	Eria mollis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10688	Flacourtia jangomas	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13403	Gadus morhua callarias	Species	Gadidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO624	Isaria fumosorosea	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22526	Justicia secunda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3214	Lavandula vera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9752	Miliusa velutina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13523	Neobalanocarpus heimii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12252	Psychotria stachyoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO986	Rattus rattus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2198	Rivularia firma	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1501	Senecio subdentatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13421	Sphaerella laricina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26777	Pneumatopteris pennigera	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO472	Penicillium restrictum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24699	Phlogacanthus curviflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317.1	Citrus aurantium var. amara	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317.1	Citrus aurantium var. amara	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24699	Phlogacanthus curviflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26401	Andrographis neesiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31520	Polygonum multiflorum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29417	Fallopia multiflora	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16590	Cytophaga hutchinsoni	Species	Cytophagaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO2631	Aster sedifolius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12252	Psychotria stachyoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12477	Dodonaea viscosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14014	Eriocheir sinensis	Species	Varunidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO624	Isaria fumosorosea	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14412	Aphyllocladus denticulatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28478	Magnolia ovata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8386	Enceliopsis argophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9243	Senecio bonariensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9448	Dictyopteris australis	Species	Dictyotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13237	Teucrium yemense	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14520	Bassia muricata	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24989	Solanum cleistogamum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16050	Rhodiola viridula	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14304	Physalis alkekengi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4345	Caulocystis cephalornithos	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2198	Rivularia firma	Species	Rivulariaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO13523	Neobalanocarpus heimii	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3214	Lavandula vera	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26465	Coreopsis tinctoria	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14217	Adansonia grandidieri	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26777	Pneumatopteris pennigera	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7819.1	Epichloe festucae var. lolii	Varieties	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12079	Dysoxylum cumingianum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10688	Flacourtia jangomas	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15297	Aconitum seravschanicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13716	Aconitum tasiromontanum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1501	Senecio subdentatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22526	Justicia secunda	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14104	Dendriopoterium menendezii	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13403	Gadus morhua callarias	Species	Gadidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26401	Andrographis neesiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13421	Sphaerella laricina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9752	Miliusa velutina	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11749	Eria mollis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1312	Pseudococcus albizziae	Species	Pseudococcidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO986	Rattus rattus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11391	Polygonum cuspidatum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23412	Uvaria afzelii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26202	Loranthus pentandrus	Species	Loranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15746	Athelia rolfsii	Species	Atheliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24699	Phlogacanthus curviflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7064	Endoconidiophora coerulescens	Species	Ceratocystidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5880	Helichrysum plicatum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25352	Pluchea odora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10152	Artemisia parviflora	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO472	Penicillium restrictum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29338	Actinidia chinensis	Species	Actinidiaceae	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
Inhibition	3
IC50	1
Activity	1

Activity Type	# Activity
Individual protein	4
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT279	Individual protein	Leukocyte elastase	Homo sapiens	Inhibition	=	26.0	%	PMID[1578486]
NPT278	Individual protein	Cathepsin G	Homo sapiens	Inhibition	=	22.0	%	PMID[1578486]
NPT3769	Individual protein	Elastase 2A	Sus scrofa	Inhibition	=	4.0	%	PMID[1578486]
NPT4782	Individual protein	Accessory gene regulator protein A	Staphylococcus aureus	IC50	=	8100.0	nM	PMID[24911880]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1397	Cell line	INS1	Rattus norvegicus	Activity	n.a.	n.a.	n.a.	PMID[36781148]

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 NPC190457 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	26401
0.1-0.2	21337
0.2-0.3	1902
0.3-0.4	153
0.4-0.5	41
0.5-0.6	11
0.6-0.7	10
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
0.7059	Intermediate Similarity	NPC93232
0.6923	Remote Similarity	NPC254847
0.6667	Remote Similarity	NPC52407
0.6667	Remote Similarity	NPC305845
0.6512	Remote Similarity	NPC244691
0.6512	Remote Similarity	NPC471906
0.65	Remote Similarity	NPC136588
0.6429	Remote Similarity	NPC70622
0.6279	Remote Similarity	NPC471905
0.6222	Remote Similarity	NPC263660
0.617	Remote Similarity	NPC147735
0.5952	Remote Similarity	NPC143438
0.5952	Remote Similarity	NPC204045
0.5814	Remote Similarity	NPC199253
0.575	Remote Similarity	NPC44437
0.5333	Remote Similarity	NPC19896
0.5306	Remote Similarity	NPC166885
0.5227	Remote Similarity	NPC253775
0.5217	Remote Similarity	NPC290550
0.5217	Remote Similarity	NPC48762
0.5102	Remote Similarity	NPC328812
0.5102	Remote Similarity	NPC607202

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC190457 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5693
0.1-0.2	3382
0.2-0.3	73
0.3-0.4	1
0.4-0.5	0
0.5-0.6	0
0.6-0.7	1
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
0.6923	Remote Similarity	NPD1509	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