NPASS Compound

Natural Product: NPC194754

Natural Product ID	NPC194754
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MHVVYWCDJGNGIX-WUXMJOGZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10977290
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002319] Phenol 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 35 35 0 0 0 0 0 0 0 0999 V2000 4.5427 -1.5916 1.7047 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1042 -1.1691 1.7140 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5264 -0.6257 0.6616 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3617 -0.4449 -0.5482 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1362 -0.2422 0.7409 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4639 -0.4132 1.7866 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4396 0.3433 -0.3312 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8835 0.6948 -0.2175 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2211 1.7763 0.6146 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5264 2.1761 0.7723 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8536 3.3395 1.6720 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5123 1.5000 0.1001 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1989 0.4421 -0.7169 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8685 0.0254 -0.8858 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5687 -1.0559 -1.7743 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4953 -1.7428 -2.3652 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1690 -1.4262 -2.0782 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5885 -2.5420 2.2790 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1764 -0.8581 2.2499 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8896 -1.7591 0.6575 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5117 -1.3100 2.6079 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5414 -1.4467 -0.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3220 0.0536 -0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7591 0.1174 -1.2891 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4346 2.3188 1.1534 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0384 3.5095 2.4002 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0749 4.2220 1.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7852 3.1154 2.2620 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5498 1.8252 0.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9991 -0.0610 -1.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2447 -2.5702 -3.0451 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5299 -1.5656 -2.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2756 -2.0071 -1.2578 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1440 -2.0678 -3.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4588 -0.5599 -2.3699 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 3 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 1 0 10 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 15 17 1 0 14 8 1 0 1 18 1 0 1 19 1 0 1 20 1 0 2 21 1 0 4 22 1 0 4 23 1 0 4 24 1 0 9 25 1 0 11 26 1 0 11 27 1 0 11 28 1 0 12 29 1 0 13 30 1 0 16 31 1 0 16 32 1 0 17 33 1 0 17 34 1 0 17 35 1 0 M END

Standard InCHIKey	MHVVYWCDJGNGIX-WUXMJOGZSA-N
Standard InCHI	InChI=1S/C15H18O2/c1-6-12(5)15(16)17-14-9-11(4)7-8-13(14)10(2)3/h6-9H,2H2,1,3-5H3/b12-6+
SMILES	C/C=C(C)/C(=O)Oc1cc(C)ccc1C(=C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	230.13	Volume:	261.201 ? Van der Waals volume.
Dense:	0.881	LogP:	3.618 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.317 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.205 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	9.0
TPSA:	26.3 ? 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:	0.447	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.557	Fsp³:	0.267
MCE-18:	9.0 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.086	Fluc inhibitor:	0.157 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.332 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.234 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.988	Promiscuous compounds:	0.215

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.796	MDCK Permeability:	-4.672
Pgp-inhibitor:	0.746	Pgp-substrate:	0.007
PAMPA:	0.038 ? 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):	0.004
20% Bioavailability (F20%):	0.12	30% Bioavailability (F30%):	0.168
50% Bioavailability (F50%):	0.413

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.731	MRP1:	0.913
Plasma Protein Binding (PPB):	97.491%	Volume Distribution (VD):	0.423
Fu:	3.132% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.979	BCRP inhibitor:	0.019
BSEP inhibitor:	0.984

ADMET: Metabolism

CYP1A2-inhibitor:	0.929	CYP1A2-substrate:	0.999
CYP2C19-inhibitor:	0.52	CYP2C19-substrate:	0.999
CYP2C9-inhibitor:	0.056	CYP2C9-substrate:	0.698
CYP2D6-inhibitor:	0.37	CYP2D6-substrate:	0.921
CYP3A4-inhibitor:	0.276	CYP3A4-substrate:	0.79
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	1.0
HLM stability:	0.989 ? 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):

7.992

Half-life (T1/2):

0.437

ADMET: Toxicity

hERG Blockers:	0.042	hERG Blockers (10um):	0.447
Human Hepatotoxicity (H-HT):	0.456	Drug-induced Liver Injury (DILI):	0.408
AMES Toxicity:	0.371	Rat Oral Acute Toxicity:	0.434
Maximum Recommended Daily Dose:	0.306	Skin Sensitization:	0.979
Carcinogencity:	0.456	Eye Corrosion:	0.878
Eye Irritation:	0.963	Respiratory Toxicity:	0.628
Drug-induced Neurotoxicity:	0.482	Ototoxicity:	0.249
Hematotoxicity:	0.332	Drug-induced Nephrotoxicity:	0.178
Genotoxicity:	0.25	RPMI-8226 Immunitoxicity:	0.069
A549 Cytotoxicity:	0.282	Hek293 Cytotoxicity:	0.178
BCF:	1.912 ? 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:	4.034 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.039 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.794 ? 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
NPO20835	Medicago truncatula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/BF00270213]
NPO19965	Helenium alternifolium	Species	Asteraceae	Eukaryota	n.a.	aerial part	n.a.	DOI[10.1021/jo01271a036]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	root	n.a.	PMID[10945272]
NPO23006	Moringa stenopetala	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12709911]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15332846]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	Amami Oshima, Kagoshima Prefecture, Japan	n.a.	PMID[16933862]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19331379]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21563811]
NPO20835	Medicago truncatula	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[21615146]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21928797]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	seed	n.a.	PMID[23497864]
NPO22372	Callicarpa bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29578342]
NPO14240	Justicia ghiesbreghtiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9748395]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22698	Achillea pannonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27489	Alloascoidea hylecoeti	Species	Alloascoideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26325	Annulusmagnus triseptatus	Species	Annulatascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22113	Anthocercis genistoides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27929	Aphanamixis polystachya	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21413	Armillaria tabescens	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22438	Asclepias speciosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22372	Callicarpa bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22499	Corydalis flabellata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13409	Crocus asturicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21654	Cyerce cristallina	Species	Caliphyllidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18123	Dichapetalum madagascariense	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19891	Diospyros crassiflora	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20967	Doriopsilla albopunctata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20381	Echites hirsuta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22756	Epimedium versicolor	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28103	Erica carnea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22953	Eupatorium pauciflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19965	Helenium alternifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15763	Huperzia lucidula	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14240	Justicia ghiesbreghtiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21032	Manilkara hexandra	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20835	Medicago truncatula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20896	Mimosa tenuiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23006	Moringa stenopetala	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21089	Mourera fluviatilis	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4478	Parmelia pseudoreticulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20583	Phaulopsis imbricata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20021	Physcia aegialita	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20088	Piper sintenense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8115	Polyopes affinis	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22048	Pteris palmiformis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20522	Pyura sacciformis	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21599	Ricciocarpos natans	Species	Ricciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22887	Scutellaria violacea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20457	Spirastrella inconstans	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22308	Stevia satureiaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20707	Stillingia sanguinolenta	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20203	Syringa komarowi	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20261	Teucrium trifidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20771	Thalictrum fortunei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21725	Uncaria glabrata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21158	Viburnum fur	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21413	Armillaria tabescens	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15763	Huperzia lucidula	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22438	Asclepias speciosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20021	Physcia aegialita	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22820	Sarcophyton glaucum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18123	Dichapetalum madagascariense	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20771	Thalictrum fortunei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21221	Trapa bispinosa	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22438	Asclepias speciosa	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21850	Paeonia delavayi	Species	Paeoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13409	Crocus asturicus	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21654	Cyerce cristallina	Species	Caliphyllidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15478	Senna sophera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21725	Uncaria glabrata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21343	Eupatorium fortunei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26325	Annulusmagnus triseptatus	Species	Annulatascaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22499	Corydalis flabellata	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28103	Erica carnea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22048	Pteris palmiformis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23006	Moringa stenopetala	Species	Moringaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19965	Helenium alternifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14240	Justicia ghiesbreghtiana	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22756	Epimedium versicolor	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21032	Manilkara hexandra	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8115	Polyopes affinis	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22372	Callicarpa bodinieri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20203	Syringa komarowi	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27489	Alloascoidea hylecoeti	Species	Alloascoideaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22887	Scutellaria violacea	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20583	Phaulopsis imbricata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20088	Piper sintenense	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21089	Mourera fluviatilis	Species	Podostemaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20381	Echites hirsuta	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21599	Ricciocarpos natans	Species	Ricciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20835	Medicago truncatula	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22113	Anthocercis genistoides	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22953	Eupatorium pauciflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21158	Viburnum fur	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27929	Aphanamixis polystachya	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20896	Mimosa tenuiflora	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20522	Pyura sacciformis	Species	Pyuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20261	Teucrium trifidum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4478	Parmelia pseudoreticulata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20457	Spirastrella inconstans	Species	Spirastrellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19891	Diospyros crassiflora	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21413	Armillaria tabescens	Species	Physalacriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20967	Doriopsilla albopunctata	Species	Dendrodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22698	Achillea pannonica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22308	Stevia satureiaefolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15763	Huperzia lucidula	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20707	Stillingia sanguinolenta	Species	Euphorbiaceae	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 NPC194754 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	21465
0.1-0.2	27241
0.2-0.3	1121
0.3-0.4	26
0.4-0.5	3
0.5-0.6	2
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
0.7273	Intermediate Similarity	NPC98748
0.5625	Remote Similarity	NPC322569
0.551	Remote Similarity	NPC329272

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC194754 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4219
0.1-0.2	4827
0.2-0.3	104
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