NPASS Compound

Natural Product: NPC271985

Natural Product ID	NPC271985
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-(4-Hydroxy-3,5-Dimethoxyphenyl)Acrylaldehyde
IUPAC Name	(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enal
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL225067
PubChem CID	5280802
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000134] Phenols [CHEMONTID:0000190] Methoxyphenols

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 27 27 0 0 0 0 0 0 0 0999 V2000 -1.4062 -3.3487 0.9404 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1024 -2.1364 0.7349 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3727 -1.0093 0.3929 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 -1.0660 0.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6975 0.0834 -0.0880 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1372 0.1329 -0.2571 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9503 -0.9015 -0.1058 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4067 -0.7655 -0.2969 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9606 0.3102 -0.6075 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0423 1.2404 -0.2758 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3927 1.3250 -0.1475 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0751 0.1640 0.1971 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4415 0.1878 0.3413 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0897 2.5092 -0.3464 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3505 3.6652 -0.6962 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1656 -4.1147 1.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7098 -3.1724 1.8102 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8305 -3.5781 0.0381 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5263 -1.9962 0.4142 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5839 1.0836 -0.5270 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5082 -1.8464 0.1622 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0114 -1.6416 -0.1595 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4753 2.1689 -0.5484 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8474 0.9045 0.9197 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6210 3.8261 0.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7782 3.4685 -1.6375 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0315 4.5073 -0.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 5 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 11 14 1 0 14 15 1 0 12 3 1 0 1 16 1 0 1 17 1 0 1 18 1 0 4 19 1 0 6 20 1 0 7 21 1 0 8 22 1 0 10 23 1 0 13 24 1 0 15 25 1 0 15 26 1 0 15 27 1 0 M END

Standard InCHIKey	CDICDSOGTRCHMG-ONEGZZNKSA-N
Standard InCHI	InChI=1S/C11H12O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-7,13H,1-2H3/b4-3+
SMILES	COc1cc(/C=C/C=O)cc(c1O)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	208.07	Volume:	212.234 ? Van der Waals volume.
Dense:	0.98	LogP:	1.642 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.613 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.622 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	8.0
TPSA:	55.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.603	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.264	Fsp³:	0.182
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:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.299	Fluc inhibitor:	0.928 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.122 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.396 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.974	Promiscuous compounds:	0.445

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.161	MDCK Permeability:	-4.837
Pgp-inhibitor:	0.84	Pgp-substrate:	0.151
PAMPA:	0.024 ? 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):	0.05
20% Bioavailability (F20%):	0.239	30% Bioavailability (F30%):	0.212
50% Bioavailability (F50%):	0.869

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.153	MRP1:	0.9
Plasma Protein Binding (PPB):	93.083%	Volume Distribution (VD):	-0.59
Fu:	5.529% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.981
OATP1B3 inhibitor:	0.984	BCRP inhibitor:	0.92
BSEP inhibitor:	0.956

ADMET: Metabolism

CYP1A2-inhibitor:	0.012	CYP1A2-substrate:	0.792
CYP2C19-inhibitor:	0.488	CYP2C19-substrate:	0.517
CYP2C9-inhibitor:	0.745	CYP2C9-substrate:	0.792
CYP2D6-inhibitor:	0.705	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.01	CYP3A4-substrate:	0.921
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.518 ? 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):

8.75

Half-life (T1/2):

1.429

ADMET: Toxicity

hERG Blockers:	0.117	hERG Blockers (10um):	0.458
Human Hepatotoxicity (H-HT):	0.449	Drug-induced Liver Injury (DILI):	0.436
AMES Toxicity:	0.672	Rat Oral Acute Toxicity:	0.476
Maximum Recommended Daily Dose:	0.397	Skin Sensitization:	0.644
Carcinogencity:	0.699	Eye Corrosion:	0.553
Eye Irritation:	0.974	Respiratory Toxicity:	0.679
Drug-induced Neurotoxicity:	0.671	Ototoxicity:	0.205
Hematotoxicity:	0.295	Drug-induced Nephrotoxicity:	0.404
Genotoxicity:	0.52	RPMI-8226 Immunitoxicity:	0.116
A549 Cytotoxicity:	0.116	Hek293 Cytotoxicity:	0.223
BCF:	1.023 ? 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:	3.581 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.853 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.417 ? 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
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1016/0031-9422(90)85209-X]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[10021943]
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10075742]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	Taiwan	n.a.	PMID[11277748]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	root	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	leaf	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	bark	n.a.	PMID[14727919]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	xylem	n.a.	PMID[14727919]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921424]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1659613]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[17918910]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	stem bark	Kunming, Yunnan Province, China	n.a.	PMID[18986199]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	Stems; Barks	n.a.	n.a.	PMID[19086868]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	Hainan, China	n.a.	PMID[19091557]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23806071]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	bark	n.a.	PMID[23823874]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	China	n.a.	PMID[25115700]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26666037]
NPO25406	Celastrus monospermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28006915]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[32786878]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798955]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25406	Celastrus monospermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26160	Thielavia terricola	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15398	Rhizopus stolonifer	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8794	Aconitum fauriei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2622	Cheilanthes mysurensis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9094	Citrus reshni	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO790	Cybister confusus	Species	Dytiscidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO182	Cylas formicarius	Species	Brentidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9234	Cynoctonum wilfordii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13443	Doris montereyensis	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6559	Duddingtonia flagrans	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1477	Egregia menziesii	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO378	Myristica argentea	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1267	Acronychia laurifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25802	Agave deserti	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25201	Aglaia pyramidata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25833	Asclepias subulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22890	Eutrochium purpureum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3963	Hortonia floribunda	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22264	Inula salsoloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24918	Jacobaea cannabifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26690	Lactarius subpiperatus	Species	Lactariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9324	Notechis scutatus	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26849	Parmelia zollingeri	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3005	Passiflora morifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25259	Schrebera swietenoides	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25358	Senecio gilliesi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25714	Solanum spirale	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13313	Talipariti tiliaceum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26789	Tephrosia bidwilli	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28636	Vernonia lilacina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24547	Xanthoria parietina	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26162	Botrydium granulatum	Species	Botrydiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25871	Cryptolestes ferrugineus	Species	Laemophloeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21329	Ilyonectria destructans	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10211	Pajanelia multijuga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26534	Streptomyces clavifer	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO42042	Boletus ornatipes	Species	Boletaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO42042	Boletus ornatipes	Species	Boletaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13313	Talipariti tiliaceum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22890	Eutrochium purpureum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21329	Ilyonectria destructans	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25201	Aglaia pyramidata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24478	Morinda coreia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3963	Hortonia floribunda	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15398	Rhizopus stolonifer	Species	Rhizopodaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26298	Zanthoxylum simulans	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19672	Hosta sieboldiana	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29276	Juglans nigra	Species	Juglandaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23754	Solanum aculeatissimum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9324	Notechis scutatus	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26160	Thielavia terricola	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26849	Parmelia zollingeri	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25833	Asclepias subulata	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9234	Cynoctonum wilfordii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9740	Dacrycarpus imbricatus	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6017	Artemisia arbuscula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10211	Pajanelia multijuga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25406	Celastrus monospermus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26409	Plakortis simplex	Species	Plakinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24918	Jacobaea cannabifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21943	Acer saccharinum	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13443	Doris montereyensis	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26690	Lactarius subpiperatus	Species	Lactariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26203	Dysidea villosa	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25802	Agave deserti	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25122	Conium maculatum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9094	Citrus reshni	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12339	Daphne feddei	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO378	Myristica argentea	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO790	Cybister confusus	Species	Dytiscidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3005	Passiflora morifolia	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26992	Sophora leachiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28636	Vernonia lilacina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25358	Senecio gilliesi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22264	Inula salsoloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2622	Cheilanthes mysurensis	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25259	Schrebera swietenoides	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1477	Egregia menziesii	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4368	Magnolia officinalis	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24547	Xanthoria parietina	Species	Teloschistaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4562	Lonchocarpus urucu	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26789	Tephrosia bidwilli	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1267	Acronychia laurifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13313	Talipariti tiliaceum	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8794	Aconitum fauriei	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO182	Cylas formicarius	Species	Brentidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26162	Botrydium granulatum	Species	Botrydiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26534	Streptomyces clavifer	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO25871	Cryptolestes ferrugineus	Species	Laemophloeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25714	Solanum spirale	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6559	Duddingtonia flagrans	Species	n.a.	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
NPO42042	Boletus ornatipes	n.a.	n.a.	0.00524	n.a.	n.a.	mg/100mL	Database [Phenol-Explorer]

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
log(1/ID50)	2
IC50	6
GI	1
Activity	3

Activity Type	# Activity
Cell line	6
Unchecked	2
Non-molecular	4

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
NPT137	Cell line	L1210	Mus musculus	log(1/ID50)	=	2.6	n.a.	PMID[16279782]
NPT137	Cell line	L1210	Mus musculus	log(1/ID50)	=	4.25	n.a.	PMID[16279782]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[21696954]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	63000.0	nM	PMID[21696954]
NPT170	Cell line	SK-MEL-28	Homo sapiens	IC50	=	66000.0	nM	PMID[21696954]
NPT114	Cell line	LoVo	Homo sapiens	IC50	=	33000.0	nM	PMID[21696954]
NPT28438	Unchecked	Unchecked	n.a.	Activity	n.a.	n.a.	n.a.	PMID[37638616]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	56000.0	nM	PMID[21696954]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	39000.0	nM	PMID[21696954]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	GI	=	50.0	%	PMID[21696954]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	2.0	%	PMID[21696954]

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 NPC271985 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	24425
0.1-0.2	19760
0.2-0.3	5129
0.3-0.4	455
0.4-0.5	71
0.5-0.6	14
0.6-0.7	3
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
0.6765	Remote Similarity	NPC229401
0.6757	Remote Similarity	NPC39793
0.6486	Remote Similarity	NPC58279
0.5854	Remote Similarity	NPC200014
0.5854	Remote Similarity	NPC109275
0.5641	Remote Similarity	NPC300326
0.549	Remote Similarity	NPC193722
0.5455	Remote Similarity	NPC48315
0.5429	Remote Similarity	NPC13755
0.5405	Remote Similarity	NPC179309
0.5294	Remote Similarity	NPC274613
0.5192	Remote Similarity	NPC83375
0.5152	Remote Similarity	NPC193067
0.5143	Remote Similarity	NPC208760
0.5116	Remote Similarity	NPC483674
0.5106	Remote Similarity	NPC111635
0.5094	Remote Similarity	NPC473408

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC271985 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4146
0.1-0.2	4816
0.2-0.3	178
0.3-0.4	9
0.4-0.5	1
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