NPASS Compound

Natural Product: NPC296518

Natural Product ID	NPC296518
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LZEKELFEQPQVCM-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5321275
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001586] Biflavonoids and polyflavonoids

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 60 65 0 0 0 0 0 0 0 0999 V2000 8.6844 3.0124 -0.7120 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5863 2.2927 -1.1831 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5284 1.8849 -0.3648 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5944 2.2197 0.9630 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5602 1.8244 1.7782 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4853 1.1044 1.2472 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 0.7087 2.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4824 0.9962 3.2641 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3983 -0.0107 1.4780 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3756 -0.3236 0.1398 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2828 -1.0707 -0.4673 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3306 -1.3491 -1.8279 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3186 -2.0569 -2.4608 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7570 -2.4860 -1.6915 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8379 -2.2288 -0.3427 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1961 -1.5180 0.2484 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9659 -2.6756 0.4790 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8947 -3.9105 1.0802 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9332 -4.3923 1.8731 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0374 -3.5826 2.0326 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1032 -2.3308 1.4199 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2132 -1.5448 1.5947 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1843 -1.9157 2.2949 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2222 -0.3028 0.9573 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1539 0.0955 0.1920 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1668 1.3940 -0.4726 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0607 1.7694 -1.2458 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9941 2.9750 -1.9040 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0378 3.8693 -1.8199 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1276 3.5270 -1.0724 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1851 2.2972 -0.4065 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9419 5.0902 -2.5013 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0902 -0.7000 0.0463 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0746 -1.8613 0.6385 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0969 -4.0070 2.8068 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7445 -4.6649 0.8680 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7775 -3.1940 -2.3039 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4063 0.0922 -0.5750 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4164 0.7670 -0.0848 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4662 1.1728 -0.8916 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4827 2.9524 -1.5071 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1199 2.5025 0.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4518 4.0737 -0.4697 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4468 2.7755 1.3165 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6094 2.0873 2.8271 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5959 -0.3095 2.1453 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1916 -0.9892 -2.3707 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3920 -2.2534 -3.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1001 -1.3347 1.3057 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8393 -5.3689 2.3288 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1126 0.3311 1.0957 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2444 1.0703 -1.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1268 3.2541 -2.5023 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9564 4.1948 -0.9837 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0672 2.0481 0.1841 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7705 5.6025 -2.7435 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2449 -4.9930 2.9086 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2865 -4.7451 -0.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1391 -2.7854 -3.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4325 0.9198 -1.9355 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 2 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 29 32 1 0 25 33 1 0 33 34 1 0 20 35 1 0 18 36 1 0 14 37 1 0 10 38 1 0 38 39 1 0 39 40 2 0 40 3 1 0 39 6 1 0 16 11 1 0 34 17 1 0 34 21 2 0 31 26 1 0 1 41 1 0 1 42 1 0 1 43 1 0 4 44 1 0 5 45 1 0 9 46 1 0 12 47 1 0 13 48 1 0 16 49 1 0 19 50 1 0 24 51 1 0 27 52 1 0 28 53 1 0 30 54 1 0 31 55 1 0 32 56 1 0 35 57 1 0 36 58 1 0 37 59 1 0 40 60 1 0 M END

Standard InCHIKey	LZEKELFEQPQVCM-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C31H20O9/c1-38-18-7-8-19-22(34)13-27(39-28(19)11-18)16-4-9-21(33)20(10-16)29-23(35)12-24(36)30-25(37)14-26(40-31(29)30)15-2-5-17(32)6-3-15/h2-14,32-33,35-36H,1H3
SMILES	COc1ccc2c(=O)cc(c3ccc(c(c3)c3c(cc(c4c(=O)cc(c5ccc(cc5)O)oc34)O)O)O)oc2c1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	536.11	Volume:	530.322 ? Van der Waals volume.
Dense:	1.011	LogP:	4.214 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.089 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.901 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	36.0
TPSA:	150.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	4.0	Rings:	6.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.221	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.872	Fsp³:	0.032
MCE-18:	35.0 ? 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:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.997	Fluc inhibitor:	0.547 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.993 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.997 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.423	Promiscuous compounds:	0.892

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.968	MDCK Permeability:	-4.769
Pgp-inhibitor:	0.033	Pgp-substrate:	0.1
PAMPA:	0.614 ? 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):	0.002
20% Bioavailability (F20%):	0.645	30% Bioavailability (F30%):	0.882
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.983
Plasma Protein Binding (PPB):	97.616%	Volume Distribution (VD):	-0.256
Fu:	1.714% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.984
BSEP inhibitor:	0.998

ADMET: Metabolism

CYP1A2-inhibitor:	0.354	CYP1A2-substrate:	0.893
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.04
CYP2C9-inhibitor:	0.972	CYP2C9-substrate:	0.794
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.085
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.943 ? 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):

2.518

Half-life (T1/2):

1.906

ADMET: Toxicity

hERG Blockers:	0.068	hERG Blockers (10um):	0.371
Human Hepatotoxicity (H-HT):	0.45	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.801	Rat Oral Acute Toxicity:	0.553
Maximum Recommended Daily Dose:	0.975	Skin Sensitization:	0.249
Carcinogencity:	0.884	Eye Corrosion:	0.001
Eye Irritation:	0.974	Respiratory Toxicity:	0.871
Drug-induced Neurotoxicity:	0.02	Ototoxicity:	0.06
Hematotoxicity:	0.084	Drug-induced Nephrotoxicity:	0.071
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.18
A549 Cytotoxicity:	0.567	Hek293 Cytotoxicity:	0.957
BCF:	1.163 ? 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:	4.633 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.003 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.849 ? 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
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	1996-Sep	PMID[10352947]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12542368]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19778086]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800857]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23872723]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28139925]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31184894]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32996318]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34885954]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35268681]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38308284]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38719900]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39410132]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12930	Apium leptophyllum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18137	Seseli indicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Pt	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Leaf Wax	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	Roots	n.a.		Database[FooDB]
NPO12930	Apium leptophyllum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18137	Seseli indicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO12930	Apium leptophyllum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18137	Seseli indicum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12930	Apium leptophyllum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12930	Apium leptophyllum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26721	Apium graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18950	Cephalotaxus fortunei	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21771	Citrus trifoliata	Species	Rutaceae	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

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC296518 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	30441
0.1-0.2	16541
0.2-0.3	2136
0.3-0.4	583
0.4-0.5	115
0.5-0.6	29
0.6-0.7	7
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
0.7917	Intermediate Similarity	NPC194593
0.7333	Intermediate Similarity	NPC121649
0.7297	Intermediate Similarity	NPC303485
0.697	Remote Similarity	NPC250266
0.6901	Remote Similarity	NPC138299
0.6709	Remote Similarity	NPC265624
0.641	Remote Similarity	NPC71061
0.6341	Remote Similarity	NPC55443
0.6282	Remote Similarity	NPC603508
0.6203	Remote Similarity	NPC290830
0.5976	Remote Similarity	NPC601565
0.597	Remote Similarity	NPC222713
0.5926	Remote Similarity	NPC14606
0.5875	Remote Similarity	NPC150908
0.5875	Remote Similarity	NPC600972
0.5823	Remote Similarity	NPC259757
0.5802	Remote Similarity	NPC158027
0.56	Remote Similarity	NPC67322
0.5595	Remote Similarity	NPC18699
0.5556	Remote Similarity	NPC234133
0.5542	Remote Similarity	NPC159707
0.5507	Remote Similarity	NPC604293
0.5476	Remote Similarity	NPC215203
0.5432	Remote Similarity	NPC606549
0.5429	Remote Similarity	NPC284424
0.5375	Remote Similarity	NPC254351
0.5309	Remote Similarity	NPC610480
0.527	Remote Similarity	NPC269652
0.5263	Remote Similarity	NPC610914
0.5238	Remote Similarity	NPC72425
0.5233	Remote Similarity	NPC205026
0.5205	Remote Similarity	NPC113089
0.519	Remote Similarity	NPC111112
0.5135	Remote Similarity	NPC231772
0.5135	Remote Similarity	NPC120163
0.5135	Remote Similarity	NPC266597
0.5132	Remote Similarity	NPC308451
0.5125	Remote Similarity	NPC288840
0.5119	Remote Similarity	NPC601984

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC296518 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5930
0.1-0.2	3155
0.2-0.3	58
0.3-0.4	5
0.4-0.5	2
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