NPASS Compound

Natural Product: NPC293201

Natural Product ID	NPC293201
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-(3,4-Dimethoxybenzylidene)-7-Methoxychroman-4-One
IUPAC Name	(3E)-3-[(3,4-dimethoxyphenyl)methylidene]-7-methoxychromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL597065
PubChem CID	5783568
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002507] Homoisoflavonoids

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 42 44 0 0 0 0 0 0 0 0999 V2000 7.3990 -0.3615 -1.7657 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0344 -0.3730 -2.0501 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0262 -0.1176 -1.1541 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2689 0.2041 0.1555 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2179 0.4591 1.0485 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9364 0.3854 0.6078 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7045 0.0586 -0.7183 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7039 -0.1977 -1.6253 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3899 -0.0043 -1.1131 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3280 -0.3472 -0.2038 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4695 0.5546 0.9665 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5282 1.2321 1.5187 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8793 1.1256 0.9948 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6372 2.2398 0.6926 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9137 2.0635 0.2387 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5041 0.7906 0.0615 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6815 -0.3117 0.3874 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4132 -0.1279 0.8378 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2489 -1.5640 0.2193 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5250 -2.7441 0.5161 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6998 0.6380 -0.3644 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8992 0.5299 -0.7927 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8368 0.6524 1.5283 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9808 0.9495 2.7258 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9336 0.4896 -2.2858 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6504 -0.2779 -0.6968 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8976 -1.2850 -2.1976 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2659 0.2808 0.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4322 0.7114 2.0762 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5635 -0.4547 -2.6614 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6167 -0.2012 -0.7707 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4041 -1.4172 0.0875 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3084 1.8735 2.3837 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1921 3.2279 0.8248 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5447 2.9254 -0.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7938 -1.0153 1.0930 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7969 -2.9304 -0.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2265 -3.6169 0.5818 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0562 -2.6941 1.5339 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2575 -0.5656 -0.8231 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0015 0.8683 -1.8823 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7188 1.0915 -0.2303 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 7 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 17 19 1 0 19 20 1 0 16 21 1 0 21 22 1 0 11 23 1 0 23 24 2 0 8 3 1 0 18 13 1 0 23 6 1 0 1 25 1 0 1 26 1 0 1 27 1 0 4 28 1 0 5 29 1 0 8 30 1 0 10 31 1 0 10 32 1 0 12 33 1 0 14 34 1 0 15 35 1 0 18 36 1 0 20 37 1 0 20 38 1 0 20 39 1 0 22 40 1 0 22 41 1 0 22 42 1 0 M END

Standard InCHIKey	YKRAQIAZPKGEIC-MDWZMJQESA-N
Standard InCHI	InChI=1S/C19H18O5/c1-21-14-5-6-15-17(10-14)24-11-13(19(15)20)8-12-4-7-16(22-2)18(9-12)23-3/h4-10H,11H2,1-3H3/b13-8+
SMILES	COc1ccc2c(c1)OC/C(=Cc1ccc(c(c1)OC)OC)/C2=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	326.12	Volume:	334.37 ? Van der Waals volume.
Dense:	0.975	LogP:	3.0 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.206 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.85 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	19.0
TPSA:	53.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	3.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.806	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.153	Fsp³:	0.211
MCE-18:	35.478 ? 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:	0.578	Fluc inhibitor:	0.998 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.73 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.656 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.353	Promiscuous compounds:	0.029

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.683	MDCK Permeability:	-4.654
Pgp-inhibitor:	0.918	Pgp-substrate:	0.002
PAMPA:	0.01 ? 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):	0.128
20% Bioavailability (F20%):	0.166	30% Bioavailability (F30%):	0.206
50% Bioavailability (F50%):	0.854

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.118
Plasma Protein Binding (PPB):	88.719%	Volume Distribution (VD):	-0.093
Fu:	9.064% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.953
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.42
CYP2C19-inhibitor:	0.884	CYP2C19-substrate:	0.336
CYP2C9-inhibitor:	0.195	CYP2C9-substrate:	0.057
CYP2D6-inhibitor:	0.846	CYP2D6-substrate:	0.864
CYP3A4-inhibitor:	0.79	CYP3A4-substrate:	0.107
CYP2B6-substrate:	0.722	CYP2C8-inhibitor:	0.934
HLM stability:	0.675 ? 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):

6.864

Half-life (T1/2):

0.833

ADMET: Toxicity

hERG Blockers:	0.552	hERG Blockers (10um):	0.434
Human Hepatotoxicity (H-HT):	0.773	Drug-induced Liver Injury (DILI):	0.919
AMES Toxicity:	0.763	Rat Oral Acute Toxicity:	0.779
Maximum Recommended Daily Dose:	0.916	Skin Sensitization:	0.642
Carcinogencity:	0.936	Eye Corrosion:	0.0
Eye Irritation:	0.105	Respiratory Toxicity:	0.549
Drug-induced Neurotoxicity:	0.803	Ototoxicity:	0.604
Hematotoxicity:	0.608	Drug-induced Nephrotoxicity:	0.919
Genotoxicity:	0.933	RPMI-8226 Immunitoxicity:	0.53
A549 Cytotoxicity:	0.532	Hek293 Cytotoxicity:	0.841
BCF:	1.547 ? 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:	4.208 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.884 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.242 ? 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
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/0031-9422(90)85349-K]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	DOI[10.1186/1471-2202-6-1]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579865]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[10716597]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10757718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11374948]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11561442]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	roots	n.a.	n.a.	PMID[12398547]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12579877]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1375626]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1602302]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[16864458]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	roots	n.a.	n.a.	PMID[16989518]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[17250858]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17265278]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[18164718]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	leaf	n.a.	PMID[1823717]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18554602]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[18996177]
NPO17186	Sibiraea angustata	Species	Rosaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[19252323]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20853876]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	root	n.a.	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[21486005]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21514608]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	dried roots	purchased from Sichuan Neautus Traditional Chinese Medicine Co. Ltd. (Chengdu, P.R. China)	n.a.	PMID[22148431]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	leaves	n.a.	n.a.	PMID[23268606]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	stem	n.a.	PMID[2380715]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2380715]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23852638]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24549173]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24963543]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25237706]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	bark	n.a.	PMID[2534610]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	PMID[2816380]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28485933]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[29355322]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30106289]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	Leaves	n.a.	n.a.	PMID[31556299]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38202695]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	root	n.a.	PMID[547813]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7102323]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7304185]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176403]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8699928]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8722541]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO11763	Cyperus capitatus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6570	Cinnamomum philippinense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9142	Aeschynanthus parvifolius	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13245	Agelas longissima	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18824	Alpinia pulcherrima	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18986	Betula papyrifera	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19495	Bignonia unguiscati	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1560	Boronia alata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18747	Bufo bankorensis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19285	Chromodoris cavae	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10957	Cladosiphon okamuranus	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19554	Coronilla hyrcana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18653	Cyathus intermedius	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2351	Echinocardium cordatum	Species	Loveniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19350	Ephedra altissima	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18326	Eria siamensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17050	Haemanthus albiflos	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16256	Helleborus viridis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17565	Hordeum bulbosum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16727	Iris sibirica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4171	Isolona pilosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18899	Keyserlingia koreensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14595	Lactarius torminosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16034	Lecanora sulphurata	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12464	Litsea nitida	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15709	Lobelia langeana	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17876	Magnolia henryi	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6642	Mocis latipes	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19222	Mycale tenuis	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17987	Mycosphaerella nawae	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17433	Peltophorum dubium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20618	Penicilliopsis clavariiformis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1457	Phoma asparagi	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19683	Pycnothymus rigidus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25549	Rhizophagus intraradices	Species	Glomeraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7328	Salvia miniata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17186	Sibiraea angustata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19416	Streptomyces sakaiensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15370	Tamarix dioica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19069	Thelepus setosus	Species	Terebellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18576	Vernonia aurea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14595	Lactarius torminosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18653	Cyathus intermedius	Species	Nidulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9142	Aeschynanthus parvifolius	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13661	Tripterygium wilfordii	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14941	Delphinium tricorne	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19069	Thelepus setosus	Species	Terebellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18747	Bufo bankorensis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18131	Micromelum falcatum	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16481	Xanthium canadense	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17050	Haemanthus albiflos	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16034	Lecanora sulphurata	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17433	Peltophorum dubium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16256	Helleborus viridis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4171	Isolona pilosa	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19554	Coronilla hyrcana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6642	Mocis latipes	Species	Noctuidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1457	Phoma asparagi	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19747	Maytenus emarginata	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19222	Mycale tenuis	Species	Mycalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19614	Erica cinerea	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15370	Tamarix dioica	Species	Tamaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7328	Salvia miniata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2351	Echinocardium cordatum	Species	Loveniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19416	Streptomyces sakaiensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO15709	Lobelia langeana	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19683	Pycnothymus rigidus	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20618	Penicilliopsis clavariiformis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18899	Keyserlingia koreensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17186	Sibiraea angustata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18824	Alpinia pulcherrima	Species	Staphylinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17565	Hordeum bulbosum	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25549	Rhizophagus intraradices	Species	Glomeraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18326	Eria siamensis	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18492	Prunus pseudocerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18986	Betula papyrifera	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17333	Valeriana officinalis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1560	Boronia alata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17876	Magnolia henryi	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19350	Ephedra altissima	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19285	Chromodoris cavae	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13245	Agelas longissima	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16727	Iris sibirica	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12464	Litsea nitida	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14595	Lactarius torminosus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6570	Cinnamomum philippinense	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17987	Mycosphaerella nawae	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11763	Cyperus capitatus	Species	Cyperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1534	Jatropha gossypiifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10957	Cladosiphon okamuranus	Species	Chordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19495	Bignonia unguiscati	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18576	Vernonia aurea	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

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
IC50	4

Activity Type	# Activity
Cell line	3
Non-molecular	1

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
NPT81	Cell line	A549	Homo sapiens	IC50	>	20000.0	nM	PMID[20036537]
NPT91	Cell line	KB	Homo sapiens	IC50	>	20000.0	nM	PMID[20036537]
NPT90	Cell line	DU-145	Homo sapiens	IC50	>	20000.0	nM	PMID[20036537]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	18300.0	nM	PMID[20036537]

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 NPC293201 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	31361
0.1-0.2	16620
0.2-0.3	1717
0.3-0.4	121
0.4-0.5	26
0.5-0.6	7
0.6-0.7	3
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8444	Intermediate Similarity	NPC125269
0.6792	Remote Similarity	NPC280284
0.6667	Remote Similarity	NPC482970
0.6275	Remote Similarity	NPC482969
0.5893	Remote Similarity	NPC188947
0.5439	Remote Similarity	NPC477231
0.5439	Remote Similarity	NPC482957
0.5231	Remote Similarity	NPC482963
0.5085	Remote Similarity	NPC31363
0.5085	Remote Similarity	NPC257648
0.5077	Remote Similarity	NPC485204

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC293201 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5299
0.1-0.2	3638
0.2-0.3	203
0.3-0.4	10
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data