NPASS Compound

Natural Product: NPC289196

Natural Product ID	NPC289196
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LPXGCZRQLILWOH-UKZWKHHHSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	16720461
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

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 51 55 0 0 0 0 0 0 0 0999 V2000 -5.4628 0.5990 2.4639 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7131 -0.1136 1.3406 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4186 0.2568 0.0626 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5143 0.1534 -1.1431 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4124 -0.8330 -0.7243 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6075 -0.0559 0.3293 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4108 0.2757 1.4070 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4370 -0.7077 0.6757 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1392 -0.3478 0.4922 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2667 0.8157 -0.1158 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5967 1.1483 -0.2848 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5554 0.2826 0.1726 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8670 0.6476 -0.0135 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8388 -0.2173 0.4436 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1642 0.0812 0.2925 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5520 1.2745 -0.3311 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5909 2.1478 -0.7926 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2583 1.8309 -0.6318 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2990 2.6198 -1.0491 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0364 2.3034 -0.8883 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1403 3.1067 -1.3128 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9697 3.3267 -1.4087 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8997 1.5482 -0.4690 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4334 -1.3886 1.0557 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3289 -2.1609 1.4638 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1466 -1.6936 1.2104 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1887 -0.9015 0.7915 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8366 -1.2098 0.9477 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5398 -2.4089 1.5748 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4078 -3.5482 0.7418 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6180 -1.0151 -1.8490 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8670 1.3941 -1.2588 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4694 -0.6495 -0.1468 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7340 1.5989 2.0622 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8076 0.7055 3.3568 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3958 0.0481 2.6917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7845 -1.2011 1.5758 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8814 1.2617 0.1351 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0171 -0.1577 -2.0569 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8215 -1.7557 -0.3102 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3575 0.9005 -0.1720 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4704 1.5132 -0.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9429 -0.5644 0.6339 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9203 3.5694 -1.5650 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5873 0.7904 -0.4588 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2639 -4.2473 0.8431 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5003 -4.1246 1.0436 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2455 -3.2693 -0.3204 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5874 -1.9866 -2.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1158 1.8503 -2.0844 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3335 -1.4921 0.3521 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 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 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 2 0 17 22 1 0 16 23 1 0 14 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 5 31 1 0 4 32 1 0 3 33 1 0 7 2 1 0 28 9 1 0 20 11 1 0 27 12 1 0 18 13 1 0 1 34 1 0 1 35 1 0 1 36 1 0 2 37 1 1 3 38 1 1 4 39 1 6 5 40 1 1 6 41 1 6 10 42 1 0 15 43 1 0 22 44 1 0 23 45 1 0 30 46 1 0 30 47 1 0 30 48 1 0 31 49 1 0 32 50 1 0 33 51 1 0 M END

Standard InCHIKey	LPXGCZRQLILWOH-UKZWKHHHSA-N
Standard InCHI	InChI=1S/C21H18O12/c1-5-12(23)14(25)15(26)21(30-5)31-9-4-7-11-10-6(19(27)33-18(11)16(9)29-2)3-8(22)13(24)17(10)32-20(7)28/h3-5,12,14-15,21-26H,1-2H3/t5-,12-,14+,15+,21-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)Oc1cc2c3c4c(cc(c(c4oc2=O)O)O)c(=O)oc3c1OC)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	462.08	Volume:	413.381 ? Van der Waals volume.
Dense:	1.118	LogP:	-0.164 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.303 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.116 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	189.26 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	5.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.157	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.287	Fsp³:	0.333
MCE-18:	107.429 ? 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:	Rejected	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.778	Fluc inhibitor:	0.032 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.781 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.836 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.09	Promiscuous compounds:	0.513

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.097	MDCK Permeability:	-5.197
Pgp-inhibitor:	0.0	Pgp-substrate:	0.531
PAMPA:	0.999 ? 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):	0.37
20% Bioavailability (F20%):	0.848	30% Bioavailability (F30%):	0.938
50% Bioavailability (F50%):	0.959

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.647
Plasma Protein Binding (PPB):	68.885%	Volume Distribution (VD):	-0.352
Fu:	30.56% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.785
OATP1B3 inhibitor:	0.88	BCRP inhibitor:	0.001
BSEP inhibitor:	0.034

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.254	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.079
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.625
HLM stability:	0.104 ? 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):

3.26

Half-life (T1/2):

3.878

ADMET: Toxicity

hERG Blockers:	0.017	hERG Blockers (10um):	0.155
Human Hepatotoxicity (H-HT):	0.649	Drug-induced Liver Injury (DILI):	0.987
AMES Toxicity:	0.749	Rat Oral Acute Toxicity:	0.124
Maximum Recommended Daily Dose:	0.243	Skin Sensitization:	0.878
Carcinogencity:	0.264	Eye Corrosion:	0.0
Eye Irritation:	0.291	Respiratory Toxicity:	0.03
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.811
Hematotoxicity:	0.217	Drug-induced Nephrotoxicity:	0.212
Genotoxicity:	0.891	RPMI-8226 Immunitoxicity:	0.113
A549 Cytotoxicity:	0.126	Hek293 Cytotoxicity:	0.155
BCF:	0.846 ? 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:	3.418 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.117 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.346 ? 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
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1007/s00217-007-0799-1]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2011.01.077]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11520216]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11524125]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11524125]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932140]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seeds	n.a.	n.a.	PMID[15620261]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16124765]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121251]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21438588]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21861494]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	whole plant	n.a.	PMID[21899269]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22080044]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22612410]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23822585]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25050371]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2607351]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33170684]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35508595]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36560643]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36985451]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792265]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38794396]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39138188]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39527985]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39769283]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[5391291]
NPO20972	Oscillatoria princeps	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25535	Cosmos pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19899	Crepis foetida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22568	Aristolochia elegans	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21227	Aglaia elaeagnoidea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21282	Aplidium orthium	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22893	Apterostigma dentigerum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2780	Brenneria rubrifaciens	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21859	Centaurea nigrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12362	Coreopsis fasciculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23010	Crinum defixum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22763	Cuphea carthagenensis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20332	Dioscoreophyllum cumminsii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20209	Dorstenia lindeniana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21603	Eskemukerjea megacarpum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22381	Euphorbia segetalis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21991	Modiolus demissus	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22829	Ozoroa insignis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22250	Parastrephia lepidophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22635	Penstemon secundiflorus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22315	Phlogacanthus thyrsiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21420	Phormia regina	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21730	Pouzolzia occidentalis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13355	Selinum carvifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22447	Sidastrum acuminatum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22509	Syncolostemon parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21473	Urtica triangularis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23953	Zanthoxylum monophyllum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25263	Aulacomnium androgynum	Species	Aulacomniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4074	Lonchocarpus orotinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25705	Cordia curassavica	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24446	Diotis maritima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25372	Valeriana fedtschenkoi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25887	Turbinaria ornata	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21196	Dichotomaria marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5771	Sinularia molesta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Stem Bark	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Twig	n.a.	n.a.	Database[FooDB]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22447	Sidastrum acuminatum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23953	Zanthoxylum monophyllum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21859	Centaurea nigrescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21730	Pouzolzia occidentalis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23010	Crinum defixum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22568	Aristolochia elegans	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20652	Phytolacca acinosa	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21227	Aglaia elaeagnoidea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20209	Dorstenia lindeniana	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21473	Urtica triangularis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16414	Thuja plicata	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22250	Parastrephia lepidophylla	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25197	Magnolia sprengeri	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20779	Garcinia hombroniana	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6395	Phedimus kamtschaticus	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24446	Diotis maritima	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22635	Penstemon secundiflorus	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21603	Eskemukerjea megacarpum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20096	Cirsium japonicum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22829	Ozoroa insignis	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21096	Cardiospermum halicacabum	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20332	Dioscoreophyllum cumminsii	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20972	Oscillatoria princeps	Species	Oscillatoriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22976	Ruta microcarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13355	Selinum carvifolium	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25263	Aulacomnium androgynum	Species	Aulacomniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22052	Aspergillus candidus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21282	Aplidium orthium	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22509	Syncolostemon parviflorus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5064	Derris uliginosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25535	Cosmos pringlei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23698	Gardneria insularis	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25372	Valeriana fedtschenkoi	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22315	Phlogacanthus thyrsiflorus	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22893	Apterostigma dentigerum	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25647	Taraxacum bicorne	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22763	Cuphea carthagenensis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24416	Artemisia tournefortiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19899	Crepis foetida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24230	Petriella sordida	Species	Microascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22381	Euphorbia segetalis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5771	Sinularia molesta	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29466	Triglochin maritima	Species	Juncaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6157	Dahlstedtia araripensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25705	Cordia curassavica	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21991	Modiolus demissus	Species	Mytilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28912	Astragalus gummifer	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21420	Phormia regina	Species	Calliphoridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12362	Coreopsis fasciculata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23313	Dioscorea althaeoides	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23975	Osteophloeum platyspermum	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21196	Dichotomaria marginata	Species	Galaxauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2780	Brenneria rubrifaciens	Species	Pectobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29226.1	Ficus cordata subsp. salicifolia	Subspecies	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4074	Lonchocarpus orotinus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22144	Daphne lancifolia	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21967	Astragalus asper	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25678	Albertisia papuana	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25862	Lafoensia glyptocarpa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24304	Glycyrrhiza lepidota	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20150	Erythrina sacleuxii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23854	Scilla maritima	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14279.1	Ficus sarmentosa var. thunbergii	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24605	Monochaetia compta	Species	Sporocadaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25887	Turbinaria ornata	Species	Sargassaceae	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 NPC289196 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	21156
0.1-0.2	25990
0.2-0.3	2206
0.3-0.4	465
0.4-0.5	30
0.5-0.6	6
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
0.7571	Intermediate Similarity	NPC46640
0.7286	Intermediate Similarity	NPC219600
0.6622	Remote Similarity	NPC611276
0.6579	Remote Similarity	NPC34436
0.6522	Remote Similarity	NPC604162
0.5921	Remote Similarity	NPC38438
0.5789	Remote Similarity	NPC263119
0.5488	Remote Similarity	NPC166674
0.5395	Remote Similarity	NPC181778
0.5217	Remote Similarity	NPC247713
0.5072	Remote Similarity	NPC603302

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC289196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5288
0.1-0.2	3804
0.2-0.3	49
0.3-0.4	8
0.4-0.5	1
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