NPASS Compound

Natural Product: NPC227894

Natural Product ID	NPC227894
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(E)-3-(3,4-Dimethoxyphenyl)Prop-2-En-1-Ol
IUPAC Name	(E)-3-(3,4-dimethoxyphenyl)prop-2-en-1-ol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1995346
PubChem CID	5387770
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0004113] Methoxybenzenes [CHEMONTID:0004111] Dimethoxybenzenes

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 28 28 0 0 0 0 0 0 0 0999 V2000 -3.0230 0.2225 3.2143 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9556 0.0310 1.8171 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7289 -0.0191 1.1448 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5273 0.1158 1.8120 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6931 0.0634 1.1241 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6404 -0.1268 -0.2332 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8695 -0.1902 -1.0020 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0815 -0.0813 -0.5253 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2935 -0.1624 -1.4167 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0008 1.0217 -1.3163 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5855 -0.2604 -0.8846 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7883 -0.2103 -0.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9817 -0.3434 -0.8747 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1571 -0.5385 -2.2378 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9773 1.3159 3.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0347 -0.1001 3.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2662 -0.3490 3.7650 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5084 0.2663 2.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6174 0.1748 1.6924 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7965 -0.3431 -2.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2274 0.0694 0.5238 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9190 -1.0422 -1.1679 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9235 -0.2487 -2.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6657 1.0202 -0.5671 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5858 -0.4119 -1.9752 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1368 -0.1399 -2.6164 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0812 -1.5820 -2.5795 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3906 0.0959 -2.7744 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 1 0 6 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 12 3 1 0 1 15 1 0 1 16 1 0 1 17 1 0 4 18 1 0 5 19 1 0 7 20 1 0 8 21 1 0 9 22 1 0 9 23 1 0 10 24 1 0 11 25 1 0 14 26 1 0 14 27 1 0 14 28 1 0 M END

Standard InCHIKey	OYICGYUCCHVYRR-ONEGZZNKSA-N
Standard InCHI	InChI=1S/C11H14O3/c1-13-10-6-5-9(4-3-7-12)8-11(10)14-2/h3-6,8,12H,7H2,1-2H3/b4-3+
SMILES	COc1ccc(/C=C/CO)cc1OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	194.09	Volume:	206.081 ? Van der Waals volume.
Dense:	0.942	LogP:	1.525 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.762 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.994 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	7.0
TPSA:	38.69 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.793	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	1.88	Fsp³:	0.273
MCE-18:	6.0 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.065	Fluc inhibitor:	0.644 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.024 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.357 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.975	Promiscuous compounds:	0.379

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.553	MDCK Permeability:	-4.634
Pgp-inhibitor:	0.83	Pgp-substrate:	0.046
PAMPA:	0.05 ? 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):	0.405
20% Bioavailability (F20%):	0.833	30% Bioavailability (F30%):	0.879
50% Bioavailability (F50%):	0.907

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.01	MRP1:	0.018
Plasma Protein Binding (PPB):	60.849%	Volume Distribution (VD):	-0.017
Fu:	34.558% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.969
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.968
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.157	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.228	CYP2C19-substrate:	0.018
CYP2C9-inhibitor:	0.334	CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.991	CYP2D6-substrate:	0.031
CYP3A4-inhibitor:	0.679	CYP3A4-substrate:	0.073
CYP2B6-substrate:	0.014	CYP2C8-inhibitor:	0.694
HLM stability:	0.46 ? 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):

8.773

Half-life (T1/2):

1.598

ADMET: Toxicity

hERG Blockers:	0.146	hERG Blockers (10um):	0.366
Human Hepatotoxicity (H-HT):	0.719	Drug-induced Liver Injury (DILI):	0.327
AMES Toxicity:	0.552	Rat Oral Acute Toxicity:	0.083
Maximum Recommended Daily Dose:	0.265	Skin Sensitization:	0.818
Carcinogencity:	0.544	Eye Corrosion:	0.678
Eye Irritation:	0.992	Respiratory Toxicity:	0.631
Drug-induced Neurotoxicity:	0.566	Ototoxicity:	0.216
Hematotoxicity:	0.224	Drug-induced Nephrotoxicity:	0.212
Genotoxicity:	0.106	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.058	Hek293 Cytotoxicity:	0.125
BCF:	0.392 ? 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:	2.724 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.206 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.356 ? 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
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94598-9]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	root	n.a.	DOI[10.2225/vol5-issue3-fulltext-4]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11325242]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12088440]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12713420]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15009205]
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[15387676]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038560]
NPO16877	Aconitum episcopale	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[21417277]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	stem	n.a.	PMID[21500777]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22365754]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25323720]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	rhizomes	Liaoning province, China	2011-SEP	PMID[25927664]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26731565]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27329938]
NPO40050	Bupleurum fruticosum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29039946]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31419126]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32078653]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33296199]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35889256]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37241721]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37800169]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38370080]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39684509]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16877	Aconitum episcopale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16552	Aromia moschata	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15193	Cacia concinna	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16119	Eucalyptus hybrid	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15902	Iris spuria	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3741	Pagrus major	Species	Sparidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7909	Parmelia vittata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9962	Pocillopora damicornis	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13926	Protaetia cuprea	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO745	Rubus trifidus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12801	Aglaia meridionalis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18061	Anacystis cyanea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17718	Artemisia schmidtiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19189	Brickellia pendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO40050	Bupleurum fruticosum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18377	Chaetomium retardatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17275	Chamaemelum scariosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3050	Cladonia pseudodidyma	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21938	Coleus carnosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18847	Copaifera paupera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9535	Cortinarius basirubescens	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18792	Crotalaria lechnaultii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16829	Dunaliella acidophila	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12072	Escallonia philippiana	Species	Escalloniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17596	Ficus maxima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18242	Gleichenia glauca	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18520	Helipterum strictum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3746	Hesperocyparis nevadensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13594	Hippocratea indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11677	Lactobacillus acidophilus	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11603	Lathyrus macrorrhizus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19057	Lentinellus omphalodes	Species	Auriscalpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18575	Ochtodes crockeri	Species	Rhizophyllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12282	Parmelia conspersa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7807	Polyporus sulphureus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18173	Pyrocystis lunula	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17190	Senecio erraticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10712	Tabebuia rosea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17068	Talaromyces wortmanni	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15608	Tanacetum santolina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17709	Timonius kaniensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15902	Iris spuria	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11677	Lactobacillus acidophilus	Species	Lactobacillaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17839	Machaerium mucronulatum	Species	Dolichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15902	Iris spuria	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18173	Pyrocystis lunula	Species	Pyrocystaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3050	Cladonia pseudodidyma	Species	Cladoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9535	Cortinarius basirubescens	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21302	Cladosporium herbarum	Species	Cladosporiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7807	Polyporus sulphureus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17709	Timonius kaniensis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17802	Simmondsia chinensis	Species	Simmondsiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3746	Hesperocyparis nevadensis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18847	Copaifera paupera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9962	Pocillopora damicornis	Species	Pocilloporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19127	Citrus tankan	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13594	Hippocratea indica	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5764	Ophioglossum vulgatum	Species	Ophioglossaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13926	Protaetia cuprea	Species	Scarabaeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7090	Ammi majus	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3741	Pagrus major	Species	Sparidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21938	Coleus carnosus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17718	Artemisia schmidtiana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18575	Ochtodes crockeri	Species	Rhizophyllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1338	Arcangelisia gusanlung	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18983	Cleidion brevipetiolatum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18306	Juniperus thurifera	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17385	Magnolia acuminata	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13963	Laurencia elata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16966	Leptospermum scoparium	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16653	Matteuccia struthiopteris	Species	Onocleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12282	Parmelia conspersa	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18707	Allium ursinum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12072	Escallonia philippiana	Species	Escalloniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17068	Talaromyces wortmanni	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11603	Lathyrus macrorrhizus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10712	Tabebuia rosea	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15358	Entandrophragma cylindricum	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16293	Babylonia japonica	Species	Buccinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19189	Brickellia pendula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17831	Millettia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25454	Plumbago europaea	Species	Plumbaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15608	Tanacetum santolina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18520	Helipterum strictum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17275	Chamaemelum scariosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7174	Callyspongia truncata	Species	Callyspongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18061	Anacystis cyanea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO9604	Amycolatopsis lurida	Species	Pseudonocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17190	Senecio erraticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18242	Gleichenia glauca	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14126	Garcinia oligantha	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17596	Ficus maxima	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18377	Chaetomium retardatum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16552	Aromia moschata	Species	Cerambycidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7909	Parmelia vittata	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16829	Dunaliella acidophila	Species	Dunaliellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19057	Lentinellus omphalodes	Species	Auriscalpiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15193	Cacia concinna	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16877	Aconitum episcopale	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12801	Aglaia meridionalis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18792	Crotalaria lechnaultii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3939	Ardisia arborescens	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16119	Eucalyptus hybrid	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO745	Rubus trifidus	Species	Rosaceae	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
GI50	45
CC50	1

Activity Type	# Activity
Cell line	46

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
NPT368	Cell line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	56754.46	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT385	Cell line	SR	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT573	Cell line	M19-MEL	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT731	Cell line	LXFL 529	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT398	Cell line	UACC-62	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT458	Cell line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT403	Cell line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	49888.45	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT165	Cell line	HeLa	Homo sapiens	CC50	=	160000.0	nM	PMID[29039946]

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 NPC227894 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	21135
0.1-0.2	23907
0.2-0.3	4230
0.3-0.4	456
0.4-0.5	90
0.5-0.6	29
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
0.7273	Intermediate Similarity	NPC4718
0.7073	Intermediate Similarity	NPC55300
0.697	Remote Similarity	NPC310905
0.6571	Remote Similarity	NPC179309
0.6216	Remote Similarity	NPC185738
0.5918	Remote Similarity	NPC114901
0.5918	Remote Similarity	NPC48990
0.58	Remote Similarity	NPC165646
0.58	Remote Similarity	NPC248355
0.5789	Remote Similarity	NPC245552
0.575	Remote Similarity	NPC78918
0.575	Remote Similarity	NPC139617
0.5682	Remote Similarity	NPC280001
0.5676	Remote Similarity	NPC229401
0.5577	Remote Similarity	NPC147821
0.5577	Remote Similarity	NPC319625
0.5577	Remote Similarity	NPC183181
0.5577	Remote Similarity	NPC41706
0.549	Remote Similarity	NPC26394
0.5455	Remote Similarity	NPC483671
0.5435	Remote Similarity	NPC94276
0.5435	Remote Similarity	NPC109822
0.5435	Remote Similarity	NPC605984
0.5385	Remote Similarity	NPC270326
0.5349	Remote Similarity	NPC483673
0.5319	Remote Similarity	NPC5423
0.5217	Remote Similarity	NPC607239
0.52	Remote Similarity	NPC72529
0.5128	Remote Similarity	NPC123948
0.5128	Remote Similarity	NPC96122
0.5122	Remote Similarity	NPC294941
0.5116	Remote Similarity	NPC258171
0.5106	Remote Similarity	NPC93034
0.5106	Remote Similarity	NPC294972

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC227894 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3809
0.1-0.2	5030
0.2-0.3	290
0.3-0.4	14
0.4-0.5	6
0.5-0.6	0
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6216	Remote Similarity	NPD5536	Phase 2

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