NPASS Compound

Natural Product: NPC181823

Natural Product ID	NPC181823
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TYHJMEIBGDDCPA-VIFPVBQESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	820378
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000195] Piperidines

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 28 28 0 0 0 0 0 0 0 0999 V2000 3.8317 0.1119 -0.3478 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4774 -0.5164 -0.2660 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4699 -1.6744 0.1057 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2354 0.1757 -0.5916 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1070 0.0289 0.3892 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3913 -1.3381 0.6371 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3878 -1.7195 -0.4648 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5514 -0.7954 -0.2649 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1238 0.6098 -0.4107 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8849 0.9982 0.0797 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.9047 2.1728 0.8991 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7737 1.2213 -0.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4526 -0.2728 0.4988 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3250 -0.2267 -1.2781 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4452 1.2707 -0.6734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8441 -0.1741 -1.5864 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5534 0.3769 1.3796 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9782 -1.3707 1.5818 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3298 -2.1276 0.6843 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8766 -1.5748 -1.4279 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6297 -2.7676 -0.2945 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3451 -1.0493 -0.9779 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9044 -0.9569 0.7889 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9214 1.2528 0.0719 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1918 0.8810 -1.5046 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9612 2.5691 0.9818 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2788 2.9596 0.4315 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5141 1.9358 1.8947 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 10 5 1 0 1 12 1 0 1 13 1 0 1 14 1 0 4 15 1 0 4 16 1 0 5 17 1 1 6 18 1 0 6 19 1 0 7 20 1 0 7 21 1 0 8 22 1 0 8 23 1 0 9 24 1 0 9 25 1 0 11 26 1 0 11 27 1 0 11 28 1 0 M END

Standard InCHIKey	TYHJMEIBGDDCPA-VIFPVBQESA-N
Standard InCHI	InChI=1S/C9H17NO/c1-8(11)7-9-5-3-4-6-10(9)2/h9H,3-7H2,1-2H3/t9-/m0/s1
SMILES	CC(=O)C[C@@H]1CCCCN1C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	155.13	Volume:	172.814 ? Van der Waals volume.
Dense:	0.898	LogP:	0.785 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.55 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.093 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	7.0
TPSA:	20.31 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	0.0	Rings:	1.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.601	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.706	Fsp³:	0.889
MCE-18:	15.529 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.095	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.022 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.364	Promiscuous compounds:	0.227

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.611	MDCK Permeability:	-4.802
Pgp-inhibitor:	0.352	Pgp-substrate:	0.699
PAMPA:	0.08 ? 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%):	0.033	30% Bioavailability (F30%):	0.135
50% Bioavailability (F50%):	0.163

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.983	MRP1:	0.895
Plasma Protein Binding (PPB):	37.771%	Volume Distribution (VD):	0.359
Fu:	63.262% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.018
OATP1B3 inhibitor:	0.005	BCRP inhibitor:	0.288
BSEP inhibitor:	0.028

ADMET: Metabolism

CYP1A2-inhibitor:	0.381	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.083
CYP2D6-inhibitor:	0.057	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.025	CYP3A4-substrate:	0.104
CYP2B6-substrate:	0.062	CYP2C8-inhibitor:	0.0
HLM stability:	0.445 ? 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):

11.213

Half-life (T1/2):

2.468

ADMET: Toxicity

hERG Blockers:	0.227	hERG Blockers (10um):	0.499
Human Hepatotoxicity (H-HT):	0.664	Drug-induced Liver Injury (DILI):	0.118
AMES Toxicity:	0.302	Rat Oral Acute Toxicity:	0.544
Maximum Recommended Daily Dose:	0.555	Skin Sensitization:	0.908
Carcinogencity:	0.265	Eye Corrosion:	0.956
Eye Irritation:	0.941	Respiratory Toxicity:	0.933
Drug-induced Neurotoxicity:	0.869	Ototoxicity:	0.244
Hematotoxicity:	0.261	Drug-induced Nephrotoxicity:	0.45
Genotoxicity:	0.196	RPMI-8226 Immunitoxicity:	0.037
A549 Cytotoxicity:	0.02	Hek293 Cytotoxicity:	0.066
BCF:	0.434 ? 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:	2.344 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.464 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.847 ? 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]
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]
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]
NPO20842	Beauveria felina	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26295595]
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]
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]
NPO19899	Crepis foetida	Species	Asteraceae	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]
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]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21349	Punica granatum	Species	Lythraceae	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]
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]
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]
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]
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]
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]
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]
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]
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]
NPO22121	Piper arboreum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21349	Punica granatum	Species	Lythraceae	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]
NPO22763	Cuphea carthagenensis	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19899	Crepis foetida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22381	Euphorbia segetalis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29466	Triglochin maritima	Species	Juncaginaceae	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]
NPO2780	Brenneria rubrifaciens	Species	Pectobacteriaceae	Bacteria	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 NPC181823 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	40723
0.1-0.2	8928
0.2-0.3	192
0.3-0.4	13
0.4-0.5	3
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	Natural Product ID
		NPC

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC181823 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6706
0.1-0.2	2330
0.2-0.3	101
0.3-0.4	13
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