NPASS Compound

Natural Product: NPC492186

Natural Product ID	NPC492186
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-(1-piperidyl)tetradeca-2,4,8-trien-1-one
IUPAC Name	1-(1-piperidyl)tetradeca-2,4,8-trien-1-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 52 52 0 0 0 0 0 0 0 0999 V2000 8.5413 -0.7417 -0.1669 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7498 0.1618 0.7607 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7839 1.0195 0.0101 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7661 0.2628 -0.7816 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9077 -0.6418 0.1018 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2013 0.1731 1.0957 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9138 0.2889 1.2548 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9429 -0.4129 0.4224 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0196 0.5486 -0.3249 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1149 -0.2754 -1.1053 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1822 -0.2782 -0.9898 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9008 0.5472 -0.0603 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1966 0.5447 0.0564 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1612 -0.2435 -0.6793 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8931 -1.0618 -1.5600 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5422 -0.0679 -0.3683 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5339 -0.8347 -1.0792 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5178 -1.3561 -0.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1954 -0.2183 0.6312 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4216 1.0576 0.6451 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9280 0.8715 0.6501 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9308 -1.6621 -0.3008 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7678 -0.2378 -1.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4651 -1.0486 0.3556 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2591 -0.4650 1.5129 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5092 0.8218 1.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3920 1.6582 -0.6769 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2664 1.6891 0.7125 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0602 0.9718 -1.2559 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2160 -0.3709 -1.5674 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6447 -1.3047 0.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3125 -1.3041 -0.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8376 0.7556 1.7943 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5095 0.9424 2.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2621 -1.0294 1.0503 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4133 -1.0990 -0.2883 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4791 1.1341 0.4276 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6290 1.2518 -0.9519 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5619 -0.9542 -1.8570 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7714 -0.9465 -1.6355 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3759 1.2479 0.6225 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5809 1.2588 0.8388 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0225 -0.2168 -1.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0547 -1.6968 -1.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2764 -1.9927 -0.5457 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9079 -1.9658 0.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1692 -0.0292 0.1103 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4557 -0.5299 1.6663 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6843 1.6635 -0.2493 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6718 1.6827 1.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4838 1.8810 0.4471 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5300 0.5512 1.6173 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 2 3 7 8 1 0 8 9 1 0 9 10 1 0 10 11 2 3 11 12 1 0 12 13 2 3 13 14 1 0 14 15 2 0 14 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 16 1 0 1 22 1 0 1 23 1 0 1 24 1 0 2 25 1 0 2 26 1 0 3 27 1 0 3 28 1 0 4 29 1 0 4 30 1 0 5 31 1 0 5 32 1 0 6 33 1 0 7 34 1 0 8 35 1 0 8 36 1 0 9 37 1 0 9 38 1 0 10 39 1 0 11 40 1 0 12 41 1 0 13 42 1 0 17 43 1 0 17 44 1 0 18 45 1 0 18 46 1 0 19 47 1 0 19 48 1 0 20 49 1 0 20 50 1 0 21 51 1 0 21 52 1 0 M END

Standard InCHIKey	DHGGORSOUREXQR-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C19H31NO/c1-2-3-4-5-6-7-8-9-10-11-13-16-19(21)20-17-14-12-15-18-20/h6-7,10-11,13,16H,2-5,8-9,12,14-15,17-18H2,1H3
SMILES	CCCCCC=CCCC=CC=CC(=O)N1CCCCC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	289.24	Volume:	337.865 ? Van der Waals volume.
Dense:	0.856	LogP:	5.368 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.925 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.673 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	10.0
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:	0.252	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.579	Fsp³:	0.632
MCE-18:	6.613 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.251	Fluc inhibitor:	0.637 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.326 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.408	Promiscuous compounds:	0.007

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.616	MDCK Permeability:	-4.741
Pgp-inhibitor:	0.798	Pgp-substrate:	0.144
PAMPA:	0.001 ? 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):	0.096
20% Bioavailability (F20%):	0.103	30% Bioavailability (F30%):	0.428
50% Bioavailability (F50%):	0.24

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.668	MRP1:	0.765
Plasma Protein Binding (PPB):	98.267%	Volume Distribution (VD):	0.308
Fu:	1.671% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.552
OATP1B3 inhibitor:	0.883	BCRP inhibitor:	0.198
BSEP inhibitor:	0.945

ADMET: Metabolism

CYP1A2-inhibitor:	0.001	CYP1A2-substrate:	0.924
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.054
CYP2C9-inhibitor:	0.997	CYP2C9-substrate:	0.202
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	0.985
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	1.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.986 ? 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):

6.213

Half-life (T1/2):

0.236

ADMET: Toxicity

hERG Blockers:	0.57	hERG Blockers (10um):	0.743
Human Hepatotoxicity (H-HT):	0.404	Drug-induced Liver Injury (DILI):	0.022
AMES Toxicity:	0.289	Rat Oral Acute Toxicity:	0.17
Maximum Recommended Daily Dose:	0.471	Skin Sensitization:	0.991
Carcinogencity:	0.111	Eye Corrosion:	0.727
Eye Irritation:	0.945	Respiratory Toxicity:	0.77
Drug-induced Neurotoxicity:	0.17	Ototoxicity:	0.258
Hematotoxicity:	0.098	Drug-induced Nephrotoxicity:	0.403
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.086
A549 Cytotoxicity:	0.66	Hek293 Cytotoxicity:	0.554
BCF:	1.73 ? 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:	4.52 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.784 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.175 ? 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
NPO14864	Clerodendrum cyrtophyllum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473423]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11575948]
NPO12347.1	Pseudomonas syringae	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12502316]
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724859]
NPO13549	Otanthus maritimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39715713]
NPO3974	Ferula gummosa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20070	Crinum stuhlmannii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4699	Dracaena ombet	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11683	Crotalaria mitchellii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6367	Cortinarius viola	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14864	Clerodendrum cyrtophyllum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26712	Cladrastis kentukea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4503	Bryonopsis laciniosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14191	Berkheya rhapontica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11151	Arnebia decumbens	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19872	Achillea magnifica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14989	Acanthothamnus aphyllus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5469	Pseudoxandra sclerocarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22084	Stypandra imbricata	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12121	Streptomyces naraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1027	Scrophularia leucoclada	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4518.1	Saccharothrix mutabilis subsp. capreolus	Subspecies	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13320	Glycosmis puberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12347.1	Pseudomonas syringae	Under-species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7042	Myrica arborea	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15066	Iridaea membranacea	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8392	Iryanthera polyneura	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12539	Lissoclinum japonicum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9338	Polygala aureocauda	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11505	Nigella aristata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13549	Otanthus maritimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7042	Myrica arborea	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8392	Iryanthera polyneura	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11151	Arnebia decumbens	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4699	Dracaena ombet	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8392	Iryanthera polyneura	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19872	Achillea magnifica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14864	Clerodendrum cyrtophyllum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11683	Crotalaria mitchellii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22084	Stypandra imbricata	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12121	Streptomyces naraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14989	Acanthothamnus aphyllus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11505	Nigella aristata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15066	Iridaea membranacea	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1027	Scrophularia leucoclada	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4503	Bryonopsis laciniosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20070	Crinum stuhlmannii	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12539	Lissoclinum japonicum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5469	Pseudoxandra sclerocarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7042	Myrica arborea	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4518.1	Saccharothrix mutabilis subsp. capreolus	Subspecies	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6367	Cortinarius viola	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13549	Otanthus maritimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26712	Cladrastis kentukea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3974	Ferula gummosa	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13320	Glycosmis puberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14191	Berkheya rhapontica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9338	Polygala aureocauda	Species	Polygalaceae	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 NPC492186 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	27694
0.1-0.2	20627
0.2-0.3	1333
0.3-0.4	175
0.4-0.5	23
0.5-0.6	1
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC42477
0.9355	High Similarity	NPC252684
0.9355	High Similarity	NPC206660
0.9032	High Similarity	NPC385
0.875	High Similarity	NPC133923
0.6842	Remote Similarity	NPC34672
0.5217	Remote Similarity	NPC209232

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC492186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6980
0.1-0.2	2076
0.2-0.3	84
0.3-0.4	9
0.4-0.5	0
0.5-0.6	1
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
0.5312	Remote Similarity	NPD866	Clinical (unspecified phase)

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