NPASS Compound

Natural Product: NPC35448

Natural Product ID	NPC35448
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(Z)-Hex-3-Enyl] Benzoate
IUPAC Name	[(Z)-hex-3-enyl] benzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3182851
PubChem CID	5367706
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001350] Benzoic 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 31 31 0 0 0 0 0 0 0 0999 V2000 -4.7953 -0.1780 -0.9113 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2255 0.0553 0.5032 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0665 -0.7949 0.7461 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8444 -0.3647 1.0269 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5452 1.0509 1.1199 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5692 1.6238 0.1507 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7035 1.1336 0.0798 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2111 -0.0416 -0.3638 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4372 -0.8934 -0.8301 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6707 -0.2824 -0.2828 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5048 0.6790 0.2384 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8814 0.4870 0.3299 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4362 -0.6964 -0.1113 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5960 -1.6490 -0.6295 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2157 -1.4681 -0.7262 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1062 -1.2434 -0.9182 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6808 0.4422 -1.0311 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0035 -0.0122 -1.6715 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1839 1.0965 0.7554 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0611 -0.3677 1.1591 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1670 -1.9061 0.7037 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0395 -1.1175 1.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1446 1.1898 2.1976 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4217 1.7344 1.1285 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0803 1.6436 -0.8757 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4615 2.7489 0.3357 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0685 1.6203 0.5900 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5536 1.2274 0.7352 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5060 -0.8924 -0.0604 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0394 -2.5767 -0.9743 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5722 -2.2485 -1.1451 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 1 0 7 8 1 0 8 9 2 0 8 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 10 1 0 1 16 1 0 1 17 1 0 1 18 1 0 2 19 1 0 2 20 1 0 3 21 1 0 4 22 1 0 5 23 1 0 5 24 1 0 6 25 1 0 6 26 1 0 11 27 1 0 12 28 1 0 13 29 1 0 14 30 1 0 15 31 1 0 M END

Standard InCHIKey	BCOXBEHFBZOJJZ-ARJAWSKDSA-N
Standard InCHI	InChI=1S/C13H16O2/c1-2-3-4-8-11-15-13(14)12-9-6-5-7-10-12/h3-7,9-10H,2,8,11H2,1H3/b4-3-
SMILES	CC/C=CCCOC(=O)c1ccccc1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	204.12	Volume:	229.246 ? Van der Waals volume.
Dense:	0.89	LogP:	3.879 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.239 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.979 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	8.0
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:	0.418	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.879	Fsp³:	0.308
MCE-18:	5.0 ? 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:	0.011	Fluc inhibitor:	0.594 ? 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:	0.085 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.999	Promiscuous compounds:	0.155

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.701	MDCK Permeability:	-4.474
Pgp-inhibitor:	0.994	Pgp-substrate:	0.001
PAMPA:	0.004 ? 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):	0.002
20% Bioavailability (F20%):	0.11	30% Bioavailability (F30%):	0.426
50% Bioavailability (F50%):	0.48

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.49	MRP1:	0.85
Plasma Protein Binding (PPB):	97.541%	Volume Distribution (VD):	-0.312
Fu:	2.25% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.044
OATP1B3 inhibitor:	0.856	BCRP inhibitor:	0.524
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	0.304	CYP1A2-substrate:	0.978
CYP2C19-inhibitor:	0.176	CYP2C19-substrate:	0.937
CYP2C9-inhibitor:	0.103	CYP2C9-substrate:	0.468
CYP2D6-inhibitor:	0.043	CYP2D6-substrate:	0.986
CYP3A4-inhibitor:	0.192	CYP3A4-substrate:	0.973
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	1.0
HLM stability:	0.996 ? 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):

7.205

Half-life (T1/2):

0.206

ADMET: Toxicity

hERG Blockers:	0.3	hERG Blockers (10um):	0.822
Human Hepatotoxicity (H-HT):	0.03	Drug-induced Liver Injury (DILI):	0.066
AMES Toxicity:	0.123	Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.035	Skin Sensitization:	0.987
Carcinogencity:	0.186	Eye Corrosion:	0.919
Eye Irritation:	0.998	Respiratory Toxicity:	0.388
Drug-induced Neurotoxicity:	0.48	Ototoxicity:	0.057
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.047
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.038
A549 Cytotoxicity:	0.057	Hek293 Cytotoxicity:	0.144
BCF:	1.24 ? 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:	4.06 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.09 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.809 ? 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
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11240-015-0798-z]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.fitote.2006.01.011]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.plaphy.2005.07.013]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1039/C39730000707]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1078/0176-1617-00195]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1155/2014/609649]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757735]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11473412]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14735439]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	callus	n.a.	PMID[15715262]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[15730255]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15730255]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	fruit	n.a.	PMID[16417304]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724861]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17315967]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18220354]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18491868]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	leaf	n.a.	n.a.	PMID[20035557]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20121251]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	atlantic-forest-soil	n.a.	PMID[20450206]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21302965]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22612410]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26566007]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	PMID[27684202]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28445039]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30024167]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32560389]
NPO9809	Scutellaria altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32772473]
NPO55789	Prunus ulmifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36302154]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36336219]
NPO43596	Cladanthus scariosus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36520049]
NPO62555	Salvia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36615289]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36675004]
NPO17197	Inula graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36808818]
NPO9773	Sideritis raeseri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37509192]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37570937]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37759401]
NPO55150	Grewia bulot	Genus	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37910669]
NPO47051	Ononis aurasiaca	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37971903]
NPO62555	Salvia fruticosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38001843]
NPO16116	Aniba canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38005295]
NPO58210	Anthemis palestina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38005810]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38217369]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792265]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[7092570]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7288445]
NPO16116	Aniba canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16019.1	Isodon japonica var. glaucocalyx	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17197	Inula graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26287	Spodoptera eridania	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7255	Pterocarpus indicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9773	Sideritis raeseri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9809	Scutellaria altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16019.1	Isodon japonica var. glaucocalyx	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7255	Pterocarpus indicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9809	Scutellaria altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16019.1	Isodon japonica var. glaucocalyx	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7255	Pterocarpus indicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9809	Scutellaria altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26834	Eutypella scoparia	Species	Diatrypaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25972	Eupolyphaga sinensis	Species	Corydiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12088	Conyza canadensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25769	Heterotheca inuloides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26134	Epimedium davidii	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2898	Quercus sessiliflora	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25870	Vaccinium vitis-idaea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26266	Isodon japonicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26607	Colobocentrotus atratus	Species	Echinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26287	Spodoptera eridania	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26699	Leonurus glaucescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26561	Micromeria pineolens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26349	Frullania tamarisci	Species	Frullaniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26900	Vallota purpurea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26654	Penicillium citreonigrum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26184	Diphasia angolensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26584	Gnidia lamprantha	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25896	Bragantia wallichii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO26161	Globba malaccensis	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26451	Ophiocoma scolopendrina	Species	Ophiocomidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26927	Salacia madagascariensis	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25923	Vismia jefensis	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26211	Knightia excelsa	Species	Proteaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14992	Prunus persica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5510	Lepidium draba	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22505	Bombax ceiba	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26406	Saussurea carthamoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26624	Ilex amara	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26023	Angelica tarokoensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26950	Maba buxifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4391	Hypericum perforatum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26319	Solanum acaule	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26806	Nidula candida	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7447	Nemalion vermiculare	Species	Liagoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25949	Streptomyces griseovariabilis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO26052	Swertia delavayi	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25739	Erysimum odoratum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25792	Delphinium andersoni	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26374	Alangium premnifolium	Species	Cornaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25995	Laurencia distichophylla	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26507	Galenia africana	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18952	Sambucus nigra	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9809	Scutellaria altissima	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16116	Aniba canelilla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7255	Pterocarpus indicus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9773	Sideritis raeseri	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17197	Inula graveolens	Species	Asteraceae	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
NPO12088	Conyza canadensis	Oil	Leaves	0.10	n.a.	n.a.	%	PMID[38792265]
NPO16116	Aniba canelilla	Oil	n.a.	0.1	n.a.	n.a.	%	PMID[38005295]
NPO17197	Inula graveolens	Oil	Aerial parts	0.2	n.a.	n.a.	%	PMID[36808818]
NPO18952	Sambucus nigra	Oil	Flowers	0.5	n.a.	n.a.	%	PMID[37759401]
NPO43596	Cladanthus scariosus	Oil	Aerial parts	0.3	n.a.	n.a.	%	PMID[36520049]
NPO43596	Cladanthus scariosus	Oil	Aerial parts	0.1	n.a.	n.a.	%	PMID[36520049]
NPO47051	Ononis aurasiaca	Oil	n.a.	0.3	n.a.	n.a.	%	PMID[37971903]
NPO55150	Grewia bulot	Oil	Leaves	0.6	n.a.	n.a.	%	PMID[37910669]
NPO55789	Prunus ulmifolia	Oil	Leaves	0.59	n.a.	n.a.	%	PMID[36302154]
NPO58210	Anthemis palestina	Oil	n.a.	0.55	n.a.	n.a.	%	PMID[38005810]
NPO58210	Anthemis palestina	Oven-dried	n.a.	0.38	n.a.	n.a.	%	PMID[38005810]
NPO62555	Salvia fruticosa	Oil	n.a.	0.12 Â± 0.00	n.a.	n.a.	%	PMID[38001843]
NPO9773	Sideritis raeseri	Oil	n.a.	0.58	n.a.	n.a.	%	PMID[37509192]
NPO9809	Scutellaria altissima	Oil	n.a.	0.38	n.a.	n.a.	%	PMID[32772473]

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
Potency	3

Activity Type	# Activity
Individual protein	1
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT163	Individual protein	Nuclear factor NF-kappa-B p105 subunit	Homo sapiens	Potency	n.a.	24544.2	nM	PubChem BioAssay data set

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Potency	n.a.	43.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	68589.6	nM	PubChem BioAssay data set

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
-	Rattus norvegicus	LD50	>	5000.0	mg/kg	ToxVal

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 NPC35448 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	17036
0.1-0.2	30272
0.2-0.3	2360
0.3-0.4	146
0.4-0.5	36
0.5-0.6	1
0.6-0.7	6
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
0.697	Remote Similarity	NPC92754
0.6571	Remote Similarity	NPC146351
0.6571	Remote Similarity	NPC608938
0.619	Remote Similarity	NPC328459
0.6061	Remote Similarity	NPC249912
0.6053	Remote Similarity	NPC78701
0.5556	Remote Similarity	NPC225060

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC35448 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	2784
0.1-0.2	5824
0.2-0.3	516
0.3-0.4	23
0.4-0.5	3
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