NPASS Compound

Natural Product: NPC221992

Natural Product ID	NPC221992
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Przewaquinone A
IUPAC Name	1-(hydroxymethyl)-6,6-dimethyl-8,9-dihydro-7H-naphtho[1,2-g][1]benzofuran-10,11-dione
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL578036
PubChem CID	619402
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0002548] Tanshinones, isotanshinones, and derivatives

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 41 44 0 0 0 0 0 0 0 0999 V2000 -3.7472 1.5946 -0.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2044 0.4878 0.0913 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7814 0.7048 1.4700 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7155 -0.8067 -0.5164 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9584 -1.9583 0.0326 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4752 -1.9688 -0.3492 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9261 -0.6183 -0.1025 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7226 0.4983 0.1391 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1398 1.7157 0.4103 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2225 1.8819 0.4518 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0408 0.7766 0.2094 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4912 0.9369 0.2355 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2838 -0.1536 -0.0173 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5865 0.2873 0.0737 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8539 -0.4936 -0.1104 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0406 -0.6999 -1.4955 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4917 1.6307 0.3791 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2342 1.9947 0.4703 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7541 -1.4612 -0.3109 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4788 -2.4544 -0.5421 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2860 -1.6291 -0.3383 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8167 -2.7821 -0.6006 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4664 -0.4657 -0.0667 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1918 2.5176 -0.7107 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8047 1.8113 -0.5032 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7166 1.2696 -1.8611 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1385 1.4824 1.9548 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7230 -0.2120 2.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8173 1.1251 1.4340 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7643 -0.9108 -0.1697 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7521 -0.7700 -1.6242 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4217 -2.9307 -0.2323 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9825 -1.8675 1.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3175 -2.3441 -1.3559 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0604 -2.7072 0.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7288 2.6208 0.6166 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7110 2.8218 0.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8161 -1.4441 0.4327 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6915 0.1171 0.2459 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5187 0.0582 -1.9030 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3052 2.3450 0.5354 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 14 17 2 0 17 18 1 0 13 19 1 0 19 20 2 0 19 21 1 0 21 22 2 0 21 23 1 0 8 2 1 0 23 11 2 0 23 7 1 0 18 12 1 0 1 24 1 0 1 25 1 0 1 26 1 0 3 27 1 0 3 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 5 33 1 0 6 34 1 0 6 35 1 0 9 36 1 0 10 37 1 0 15 38 1 0 15 39 1 0 16 40 1 0 17 41 1 0 M END

Standard InCHIKey	CEHVTERMWMYLCP-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C19H18O4/c1-19(2)7-3-4-11-13(19)6-5-12-15(11)17(22)16(21)14-10(8-20)9-23-18(12)14/h5-6,9,20H,3-4,7-8H2,1-2H3
SMILES	CC1(C)CCCc2c1ccc1-c3c(c(CO)co3)C(=O)C(=O)c21

Calculated Properties

Physi-Chem Properties

Molecular Weight:	310.12	Volume:	319.66 ? Van der Waals volume.
Dense:	0.97	LogP:	2.869 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.655 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.598 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	22.0
TPSA:	67.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.819	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.062	Fsp³:	0.368
MCE-18:	55.385 ? 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:	0.186	Fluc inhibitor:	0.38 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.711 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.59 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.037	Promiscuous compounds:	0.135

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.677	MDCK Permeability:	-4.648
Pgp-inhibitor:	0.991	Pgp-substrate:	0.0
PAMPA:	0.314 ? 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):	0.947
20% Bioavailability (F20%):	0.02	30% Bioavailability (F30%):	0.91
50% Bioavailability (F50%):	0.875

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.516
Plasma Protein Binding (PPB):	98.972%	Volume Distribution (VD):	0.306
Fu:	0.865% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.932
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.016
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.682	CYP1A2-substrate:	0.966
CYP2C19-inhibitor:	0.883	CYP2C19-substrate:	0.724
CYP2C9-inhibitor:	0.165	CYP2C9-substrate:	0.997
CYP2D6-inhibitor:	0.003	CYP2D6-substrate:	0.791
CYP3A4-inhibitor:	0.053	CYP3A4-substrate:	0.954
CYP2B6-substrate:	0.001	CYP2C8-inhibitor:	1.0
HLM stability:	0.994 ? 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):

5.148

Half-life (T1/2):

0.585

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.314
Human Hepatotoxicity (H-HT):	0.713	Drug-induced Liver Injury (DILI):	0.897
AMES Toxicity:	0.883	Rat Oral Acute Toxicity:	0.619
Maximum Recommended Daily Dose:	0.881	Skin Sensitization:	0.866
Carcinogencity:	0.955	Eye Corrosion:	0.0
Eye Irritation:	0.542	Respiratory Toxicity:	0.55
Drug-induced Neurotoxicity:	0.311	Ototoxicity:	0.623
Hematotoxicity:	0.838	Drug-induced Nephrotoxicity:	0.636
Genotoxicity:	0.991	RPMI-8226 Immunitoxicity:	0.169
A549 Cytotoxicity:	0.154	Hek293 Cytotoxicity:	0.659
BCF:	1.845 ? 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:	4.683 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.412 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.9 ? 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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 17014425]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1002/bab.1236]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s11306-014-0728-9]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2010.09.006]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	retail stores, supermarkets and market stalls in Forssa and in the Helsinki area	2003Ã¢â‚¬â€œ2005	DOI[10.1016/j.jfca.2006.05.007]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jplph.2011.12.019]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1038/sdata.2014.29]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1093/jxb/erx356]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11171227]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[12576668]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880325]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	Himeji City, Japan	n.a.	PMID[15053555]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1567426]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15877880]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17217287]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17764147]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	Northeastern Regional Plant Introduction Station at Geneva	1966, 1967, and 1968 crop seasons	PMID[18460139]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	seed	n.a.	PMID[25891114]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2831703]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570961]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37980871]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[7092570]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO415	Deguelia hatschbachii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25212	Ritterella rubra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22016	Notholaena dealbata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4009	Allochromatium minutissimum	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23960	Artemisia siversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27437	Camptothecium lutescens	Species	Brachytheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26223	Cladonia bellidiflora	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25868	Decachaeta ovatifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12476	Delphinium cyphoplectrum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26087	Euphorbia retusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10497	Hydrolithon reinboldii	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26054	Palmaria palmata	Species	Palmariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6346	Phallusia fumigata	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26316	Pleurophycus gardneri	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23417	Rhabdia lycioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10155	Stauntonia obovatifoliola	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25974	Streptomyces lateritius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24988	Viburnum sieboldi	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5313	Miscanthus sinensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25813.1	Salvia przewalskii var. mandarinorum	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5313	Miscanthus sinensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	Database[MetaboLights]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25813.1	Salvia przewalskii var. mandarinorum	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5313	Miscanthus sinensis	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31303	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26223	Cladonia bellidiflora	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23417	Rhabdia lycioides	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6346	Phallusia fumigata	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25974	Streptomyces lateritius	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO415	Deguelia hatschbachii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24988	Viburnum sieboldi	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4009	Allochromatium minutissimum	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22016	Notholaena dealbata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26054	Palmaria palmata	Species	Palmariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24740	Uvaria klaineana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25868	Decachaeta ovatifolia	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26087	Euphorbia retusa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21080	Solanum lycopersicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28257	Dioscorea communis	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25701	Amentotaxus yunnanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12476	Delphinium cyphoplectrum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25813	Salvia przewalskii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10497	Hydrolithon reinboldii	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23960	Artemisia siversiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27437	Camptothecium lutescens	Species	Brachytheciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25212	Ritterella rubra	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10155	Stauntonia obovatifoliola	Species	Lardizabalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26316	Pleurophycus gardneri	Species	Alariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25779	Vicia sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5313	Miscanthus sinensis	Species	Poaceae	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	5
ED50	1
Emax	1

Activity Type	# Activity
Individual protein	5
Tissue	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1078	Individual protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	=	1070.0	nM	PMID[35358772]
NPT2961	Individual protein	Tryptophan 2,3-dioxygenase	Homo sapiens	IC50	=	450.0	nM	PMID[35358772]
NPT2961	Individual protein	Tryptophan 2,3-dioxygenase	Homo sapiens	IC50	=	7180.0	nM	PMID[35358772]
NPT1078	Individual protein	Indoleamine 2,3-dioxygenase	Homo sapiens	IC50	>	10000.0	nM	PMID[35358772]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT3912	Tissue	Artery	Sus scrofa	ED50	=	-7.4	ug ml-1	PMID[18855446]
NPT3912	Tissue	Artery	Sus scrofa	Emax	=	29.2	%	PMID[18855446]

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 NPC221992 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	18129
0.1-0.2	31413
0.2-0.3	291
0.3-0.4	14
0.4-0.5	4
0.5-0.6	3
0.6-0.7	3
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
0.7857	Intermediate Similarity	NPC281398
0.6885	Remote Similarity	NPC145830
0.6212	Remote Similarity	NPC23559
0.6154	Remote Similarity	NPC144010
0.597	Remote Similarity	NPC608807
0.5846	Remote Similarity	NPC179170
0.5231	Remote Similarity	NPC605467

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC221992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2994
0.1-0.2	6118
0.2-0.3	37
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