NPASS Compound

Natural Product: NPC190955

Natural Product ID	NPC190955
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2Z)-5-{[(2E,4E,6E)-7-(2-Thienyl)-2,4,6-Heptatrienoyl]Amino}-2-Pentenyl 3-Methylbutanoate
IUPAC Name	[(Z)-5-[[(2E,4E,6E)-7-thiophen-2-ylhepta-2,4,6-trienoyl]amino]pent-2-enyl] 3-methylbutanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2442639
PubChem CID	72696081
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000324] Fatty acid esters

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 53 53 0 0 0 0 0 0 0 0999 V2000 -7.3506 -0.4541 0.0060 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7446 -1.5197 0.8951 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7733 -2.5139 1.3514 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6707 -2.2273 0.0838 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6748 -1.1857 -0.2971 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8818 -0.7854 0.5796 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6224 -0.6757 -1.5664 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7147 0.3068 -2.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8161 1.5823 -1.2457 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8553 2.1470 -0.5537 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4999 1.6093 -0.4057 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1024 1.3411 1.0427 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2319 0.8339 1.0580 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6217 -0.1316 1.7754 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0317 -0.5749 1.7117 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8337 0.0609 0.9098 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2475 -0.2477 0.7285 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0441 0.3932 -0.0703 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4594 0.0835 -0.2486 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2224 0.7710 -1.0766 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6393 0.4696 -1.2624 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4083 -0.4978 -0.6901 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6987 -0.5611 -1.0284 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2008 0.3480 -1.9372 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7431 1.3540 -2.3334 S 0 0 0 0 0 0 0 0 0 0 0 0 -0.2310 -0.7927 2.6246 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6163 -0.8357 -0.9925 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5367 0.3034 -0.1577 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1741 0.0928 0.5020 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2347 -0.9921 1.7235 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9074 -2.3895 2.4492 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4599 -3.5473 1.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7409 -2.2779 0.8511 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1211 -2.6602 -0.8260 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2171 -3.0161 0.7320 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9581 0.5866 -3.0748 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6913 -0.0998 -2.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7800 2.1441 -1.2432 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0428 3.1044 -0.0258 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8013 2.4245 -0.7869 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2749 0.7428 -1.0475 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8621 0.7292 1.5137 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0783 2.3116 1.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4196 -1.3846 2.2883 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4257 0.8988 0.3146 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6582 -1.0652 1.2997 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6330 1.2133 -0.6442 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9037 -0.7280 0.3083 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7554 1.5771 -1.6228 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9063 -1.1927 0.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3727 -1.3455 -0.5798 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2090 0.4917 -2.3612 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2318 -0.8187 2.5655 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 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 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 14 26 1 0 25 21 1 0 1 27 1 0 1 28 1 0 1 29 1 0 2 30 1 0 3 31 1 0 3 32 1 0 3 33 1 0 4 34 1 0 4 35 1 0 8 36 1 0 8 37 1 0 9 38 1 0 10 39 1 0 11 40 1 0 11 41 1 0 12 42 1 0 12 43 1 0 15 44 1 0 16 45 1 0 17 46 1 0 18 47 1 0 19 48 1 0 20 49 1 0 22 50 1 0 23 51 1 0 24 52 1 0 26 53 1 0 M END

Standard InCHIKey	UXKHBPOYZOPFIH-MKAYIHSVSA-N
Standard InCHI	InChI=1S/C21H27NO3S/c1-18(2)17-21(24)25-15-9-5-8-14-22-20(23)13-7-4-3-6-11-19-12-10-16-26-19/h3-7,9-13,16,18H,8,14-15,17H2,1-2H3,(H,22,23)/b4-3+,9-5-,11-6+,13-7+
SMILES	CC(C)CC(=O)OC/C=CCCN=C(/C=C/C=C/C=C/c1cccs1)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	373.17	Volume:	398.0 ? Van der Waals volume.
Dense:	0.938	LogP:	4.766 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.562 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.422 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	11.0
TPSA:	58.89 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.142	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.497	Fsp³:	0.333
MCE-18:	7.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.952	Fluc inhibitor:	0.838 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.11 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.786 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.335	Promiscuous compounds:	0.063

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.583	MDCK Permeability:	-4.592
Pgp-inhibitor:	0.015	Pgp-substrate:	0.161
PAMPA:	0.553 ? 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):	0.072
20% Bioavailability (F20%):	0.884	30% Bioavailability (F30%):	0.912
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.004
Plasma Protein Binding (PPB):	96.268%	Volume Distribution (VD):	-0.193
Fu:	3.442% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.99
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.009
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.398	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.975
CYP2C9-inhibitor:	0.008	CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.028	CYP2D6-substrate:	0.255
CYP3A4-inhibitor:	0.687	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.286 ? 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):

8.401

Half-life (T1/2):

0.346

ADMET: Toxicity

hERG Blockers:	0.128	hERG Blockers (10um):	0.261
Human Hepatotoxicity (H-HT):	0.865	Drug-induced Liver Injury (DILI):	0.913
AMES Toxicity:	0.807	Rat Oral Acute Toxicity:	0.381
Maximum Recommended Daily Dose:	0.133	Skin Sensitization:	0.999
Carcinogencity:	0.775	Eye Corrosion:	0.013
Eye Irritation:	0.621	Respiratory Toxicity:	0.94
Drug-induced Neurotoxicity:	0.185	Ototoxicity:	0.436
Hematotoxicity:	0.25	Drug-induced Nephrotoxicity:	0.757
Genotoxicity:	0.388	RPMI-8226 Immunitoxicity:	0.018
A549 Cytotoxicity:	0.007	Hek293 Cytotoxicity:	0.046
BCF:	1.096 ? 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:	3.802 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.124 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.744 ? 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	Pseudomonas syringae	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14714872]
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]
NPO4518.1	Saccharothrix mutabilis subsp. capreolus	Subspecies	Pseudonocardiaceae	Bacteria	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]
NPO13320	Glycosmis puberula	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5469	Pseudoxandra sclerocarpa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15066	Iridaea membranacea	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13549	Otanthus maritimus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11505	Nigella aristata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7042	Myrica arborea	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12539	Lissoclinum japonicum	Species	Didemnidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8392	Iryanthera polyneura	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9338	Polygala aureocauda	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7042	Myrica arborea	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10210	Artabotrys uncinatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8392	Iryanthera polyneura	Species	Myristicaceae	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]
NPO22084	Stypandra imbricata	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1027	Scrophularia leucoclada	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15066	Iridaea membranacea	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11505	Nigella aristata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14989	Acanthothamnus aphyllus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12121	Streptomyces naraensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15166	Cephalotaxus hainanensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12993	Polypodium vulgare	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12347	Pseudomonas syringae	Species	Pseudomonadaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11683	Crotalaria mitchellii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14864	Clerodendrum cyrtophyllum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9734	Vincetoxicum hirundinaria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19872	Achillea magnifica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8392	Iryanthera polyneura	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4699	Dracaena ombet	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11151	Arnebia decumbens	Species	Boraginaceae	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

Activity Type	# Activity
Ki	4
Ratio Ki	2

Activity Type	# Activity
Individual protein	4
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1167	Individual protein	Delta opioid receptor	Mus musculus	Ki	=	11000.0	nM	PMID[24095014]
NPT1168	Individual protein	Mu opioid receptor	Mus musculus	Ki	=	41500.0	nM	PMID[24095014]
NPT1169	Individual protein	Cannabinoid CB2 receptor	Mus musculus	Ki	=	10200.0	nM	PMID[24095014]
NPT1170	Individual protein	Cannabinoid CB1 receptor	Mus musculus	Ki	=	5600.0	nM	PMID[24095014]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	0.27	n.a.	PMID[24095014]
NPT2	Others	Unspecified	n.a.	Ratio Ki	=	0.55	n.a.	PMID[24095014]

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 NPC190955 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	14884
0.1-0.2	34477
0.2-0.3	489
0.3-0.4	5
0.4-0.5	1
0.5-0.6	0
0.6-0.7	2
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
0.6885	Remote Similarity	NPC300455
0.6129	Remote Similarity	NPC166487

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC190955 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2737
0.1-0.2	6274
0.2-0.3	137
0.3-0.4	2
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