NPASS Compound

Natural Product: NPC14234

Natural Product ID	NPC14234
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hydroxy-Gamma-Sanshool
IUPAC Name	(2E,4E,8Z,10E,12E)-N-(2-hydroxy-2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3086846
PubChem CID	14135317
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000331] Fatty amides [CHEMONTID:0001096] N-acyl amines

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 48 47 0 0 0 0 0 0 0 0999 V2000 6.8201 1.2687 -3.1784 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6934 1.2724 -1.6811 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7279 0.6237 -1.0674 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6544 0.6621 0.3804 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6820 0.0129 1.0638 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6684 0.0937 2.5083 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7339 -0.5303 3.1721 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6976 -1.3084 2.5436 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3522 -0.6901 2.9232 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2233 -1.4521 2.3016 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6058 -0.8472 1.4717 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7215 -1.5278 0.8342 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5096 -0.8580 0.0147 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6185 -1.5326 -0.6194 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4167 -0.9424 -1.4218 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.3868 0.4195 -1.8368 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4317 1.1758 -1.0381 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4763 2.5239 -1.3759 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1441 1.0826 0.4423 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7654 0.5109 -1.3361 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8281 -2.8799 -0.3470 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2420 2.1066 -3.5953 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4593 0.2903 -3.5428 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8972 1.3205 -3.4045 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4033 1.8159 -1.0691 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9846 0.0608 -1.6080 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3887 1.2197 0.9380 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0113 -0.5027 0.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4497 0.6807 2.9936 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7222 -0.4695 4.2718 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6972 -2.3245 3.0610 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7362 -1.5330 1.4951 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2934 0.3658 2.5944 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1955 -0.6973 4.0220 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0708 -2.4997 2.5206 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4161 0.1988 1.2817 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9196 -2.5671 1.0157 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3608 0.1937 -0.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4192 0.9313 -1.7650 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6430 0.4297 -2.9312 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2412 3.1143 -0.6123 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1569 1.5204 0.6664 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1458 0.0434 0.8126 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9164 1.6991 0.9658 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0586 0.6996 -2.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5765 -0.5917 -1.2464 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5217 0.8129 -0.6019 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5247 -3.3955 -0.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 2 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 17 19 1 0 17 20 1 0 14 21 1 0 1 22 1 0 1 23 1 0 1 24 1 0 2 25 1 0 3 26 1 0 4 27 1 0 5 28 1 0 6 29 1 0 7 30 1 0 8 31 1 0 8 32 1 0 9 33 1 0 9 34 1 0 10 35 1 0 11 36 1 0 12 37 1 0 13 38 1 0 16 39 1 0 16 40 1 0 18 41 1 0 19 42 1 0 19 43 1 0 19 44 1 0 20 45 1 0 20 46 1 0 20 47 1 0 21 48 1 0 M END

Standard InCHIKey	CRPPMKFSMRODIQ-JDXPBYPHSA-N
Standard InCHI	InChI=1S/C18H27NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(2,3)21/h4-9,12-15,21H,10-11,16H2,1-3H3,(H,19,20)/b5-4+,7-6+,9-8-,13-12+,15-14+
SMILES	C/C=C/C=C/C=CCC/C=C/C=C/C(=NCC(O)(C)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	289.2	Volume:	332.643 ? Van der Waals volume.
Dense:	0.869	LogP:	3.258 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.702 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.061 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	6.0
TPSA:	52.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	2.0	Rings:	0.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.288	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.855	Fsp³:	0.389
MCE-18:	0.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.132	Fluc inhibitor:	0.389 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.02 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.487	Promiscuous compounds:	0.152

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.831	MDCK Permeability:	-4.73
Pgp-inhibitor:	0.054	Pgp-substrate:	0.37
PAMPA:	0.32 ? 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):	0.001
20% Bioavailability (F20%):	0.01	30% Bioavailability (F30%):	0.218
50% Bioavailability (F50%):	0.74

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.027
Plasma Protein Binding (PPB):	68.297%	Volume Distribution (VD):	-0.198
Fu:	29.259% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.625
OATP1B3 inhibitor:	0.764	BCRP inhibitor:	0.186
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.571	CYP1A2-substrate:	0.3
CYP2C19-inhibitor:	0.131	CYP2C19-substrate:	0.131
CYP2C9-inhibitor:	0.012	CYP2C9-substrate:	0.387
CYP2D6-inhibitor:	0.337	CYP2D6-substrate:	0.168
CYP3A4-inhibitor:	0.056	CYP3A4-substrate:	0.71
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.012 ? 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):

3.679

Half-life (T1/2):

1.084

ADMET: Toxicity

hERG Blockers:	0.141	hERG Blockers (10um):	0.228
Human Hepatotoxicity (H-HT):	0.905	Drug-induced Liver Injury (DILI):	0.709
AMES Toxicity:	0.904	Rat Oral Acute Toxicity:	0.351
Maximum Recommended Daily Dose:	0.656	Skin Sensitization:	0.998
Carcinogencity:	0.76	Eye Corrosion:	0.002
Eye Irritation:	0.723	Respiratory Toxicity:	0.871
Drug-induced Neurotoxicity:	0.166	Ototoxicity:	0.648
Hematotoxicity:	0.258	Drug-induced Nephrotoxicity:	0.754
Genotoxicity:	0.447	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.036	Hek293 Cytotoxicity:	0.336
BCF:	1.091 ? 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:	3.844 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.168 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.538 ? 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
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/S0031-9422(00)88469-1]
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)88469-1]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24175626]
NPO12970	Aspergillus fischeri	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31920082]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36786362]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37029634]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37049761]
NPO10128	Aplysia punctata	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9213585]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8253	Alexandrium hiranoi	Species	Gonyaulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10128	Aplysia punctata	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12970	Aspergillus fischeri	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6801	Bellium bellidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13438	Centaurea calcitrapa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5604	Chelonia japonica	Species	Cheloniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4895	Coleus esquirolii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8022	Consolida hohenackeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2999	Coprinellus flocculosus	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9995	Cynara humilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16266	Didymium bahiense	Species	Didymiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6320	Echinosophora koreensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6894	Elegia deusta	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14793	Erica glauca	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6556	Garcinia intermedia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26898	Jacobaea vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO777	Kielmeyera coriacea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20059.1	Lactobacillus delbrueckii subsp. bulgaricus	Subspecies	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3341	Leishmania major	Species	Trypanosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15558	Leucas neufliseana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8642	Lithospermum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1070	Matricaria suffruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24083.1	Melanelixia fuliginosa subsp. glabratula	Subspecies	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9476	Metapenaeus bennettae	Species	Penaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10264	Platonia insignis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4523	Reaumuria hirtella	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1682	Rhytidoponera metallica	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7650	Salvia munzii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9087	Sarcococca vagans	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7847	Senecio densiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7028	Sida veronicaefolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7841	Solanum transcaucasicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9733	Spongia bilamellata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2199	Tecoma pentaphylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9221	Trachelospermum lucidum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2015	Udotea petiolata	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4120	Ulmus americana	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1467	Wedelia prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2892	Wikstroemia chamaedaphne	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6378	Wilcoxia viperina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9590	Xanthoria aureola	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6320	Echinosophora koreensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1070	Matricaria suffruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2892	Wikstroemia chamaedaphne	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8642	Lithospermum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4120	Ulmus americana	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9087	Sarcococca vagans	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9087	Sarcococca vagans	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6320	Echinosophora koreensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2892	Wikstroemia chamaedaphne	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26898	Jacobaea vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4120	Ulmus americana	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1070	Matricaria suffruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8642	Lithospermum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9087	Sarcococca vagans	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8642	Lithospermum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7841	Solanum transcaucasicum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8471	Angelica taiwaniana	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6556	Garcinia intermedia	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1467	Wedelia prostrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9087	Sarcococca vagans	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4895	Coleus esquirolii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16266	Didymium bahiense	Species	Didymiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20059.1	Lactobacillus delbrueckii subsp. bulgaricus	Subspecies	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10264	Platonia insignis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1682	Rhytidoponera metallica	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7650	Salvia munzii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8642	Lithospermum officinale	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4523	Reaumuria hirtella	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8022	Consolida hohenackeri	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26898	Jacobaea vulgaris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5852	Litsea glutinosa	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4120	Ulmus americana	Species	Ulmaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5315	Zanthoxylum bungeanum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9221	Trachelospermum lucidum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1070	Matricaria suffruticosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9476	Metapenaeus bennettae	Species	Penaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO777	Kielmeyera coriacea	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10128	Aplysia punctata	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9995	Cynara humilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6320	Echinosophora koreensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2015	Udotea petiolata	Species	Udoteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9733	Spongia bilamellata	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6894	Elegia deusta	Species	Restionaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7847	Senecio densiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2892	Wikstroemia chamaedaphne	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14793	Erica glauca	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2199	Tecoma pentaphylla	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7028	Sida veronicaefolia	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5604	Chelonia japonica	Species	Cheloniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6801	Bellium bellidioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12970	Aspergillus fischeri	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2999	Coprinellus flocculosus	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24083.1	Melanelixia fuliginosa subsp. glabratula	Subspecies	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6378	Wilcoxia viperina	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO8253	Alexandrium hiranoi	Species	Gonyaulacaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9590	Xanthoria aureola	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3341	Leishmania major	Species	Trypanosomatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13438	Centaurea calcitrapa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15558	Leucas neufliseana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Inhibition	2
IC50	2
Ratio IC50	1

Activity Type	# Activity
Individual protein	4
Others	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1287	Individual protein	Cannabinoid CB2 receptor	Homo sapiens	Inhibition	=	65.0	%	PMID[24175626]
NPT1287	Individual protein	Cannabinoid CB2 receptor	Homo sapiens	IC50	=	197.0	nM	PMID[24175626]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	Inhibition	=	31.0	%	PMID[24175626]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	IC50	=	184.0	nM	PMID[24175626]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Ratio IC50	=	0.9	n.a.	PMID[24175626]

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 NPC14234 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	32328
0.1-0.2	17106
0.2-0.3	360
0.3-0.4	24
0.4-0.5	17
0.5-0.6	7
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC269800
0.8824	High Similarity	NPC132669
0.8824	High Similarity	NPC184014
0.7632	Intermediate Similarity	NPC44193
0.7632	Intermediate Similarity	NPC246519
0.7368	Intermediate Similarity	NPC312826
0.7368	Intermediate Similarity	NPC486662
0.6757	Remote Similarity	NPC267340
0.675	Remote Similarity	NPC235311
0.675	Remote Similarity	NPC253468
0.6486	Remote Similarity	NPC145032
0.6486	Remote Similarity	NPC304223
0.6486	Remote Similarity	NPC54542
0.6053	Remote Similarity	NPC307435
0.5778	Remote Similarity	NPC77891
0.5641	Remote Similarity	NPC267692
0.55	Remote Similarity	NPC243539
0.5217	Remote Similarity	NPC150505
0.5217	Remote Similarity	NPC74617
0.5208	Remote Similarity	NPC471022
0.5116	Remote Similarity	NPC303672

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC14234 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6663
0.1-0.2	2449
0.2-0.3	38
0.3-0.4	0
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