NPASS Compound

Natural Product: NPC153758

Natural Product ID	NPC153758
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3,7,4'-Tri-O-Acetyl Kaempferol
IUPAC Name	[4-(3,7-diacetyloxy-5-hydroxy-4-oxochromen-2-yl)phenyl] acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL516683
PubChem CID	44584293
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001615] Flavones

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 46 48 0 0 0 0 0 0 0 0999 V2000 6.9568 0.8274 -3.6081 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5930 0.4763 -3.1205 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6680 0.2770 -3.9457 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3122 0.3625 -1.7762 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0664 0.0405 -1.2788 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2031 1.0916 -1.0070 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9466 0.8852 -0.5115 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4701 -0.4116 -0.2534 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3302 -1.4193 -0.5275 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6249 -1.2353 -1.0359 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1056 -0.5734 0.2417 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6650 0.5322 0.2201 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8920 0.5874 0.6144 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6368 1.7612 0.5669 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9455 1.7852 0.9961 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6719 2.9679 0.9405 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4114 3.3351 -0.1575 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4252 2.5611 -1.1496 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1976 4.6143 -0.2187 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5577 0.6322 1.4897 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7905 -0.5133 1.5226 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4717 -0.5663 1.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7361 -1.7309 1.1464 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2198 -2.7938 1.5746 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3995 -1.7482 0.7071 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3309 -2.9125 0.7632 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8562 -3.3321 2.0071 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6119 -2.5970 2.9841 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6541 -4.5937 2.0976 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.7081 2.0025 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6879 0.2957 -2.9732 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1568 1.9120 -3.4952 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1190 0.5466 -4.6560 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5147 2.1096 -1.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2801 1.7034 -0.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0456 -2.4457 -0.3846 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2877 -2.0543 -1.2438 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1783 2.6711 0.1857 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5673 4.7824 0.8163 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0365 4.4597 -0.9059 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5445 5.4255 -0.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5874 0.6624 1.8246 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2051 -4.7163 1.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9222 -5.4295 2.1255 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3414 -4.5708 2.9521 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0256 -1.9537 2.9566 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 8 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 15 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 27 29 1 0 21 30 1 0 10 5 1 0 25 11 2 0 22 13 1 0 1 31 1 0 1 32 1 0 1 33 1 0 6 34 1 0 7 35 1 0 9 36 1 0 10 37 1 0 14 38 1 0 19 39 1 0 19 40 1 0 19 41 1 0 20 42 1 0 29 43 1 0 29 44 1 0 29 45 1 0 30 46 1 0 M END

Standard InCHIKey	DJKUFDVJACBQPB-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C21H16O9/c1-10(22)27-14-6-4-13(5-7-14)20-21(29-12(3)24)19(26)18-16(25)8-15(28-11(2)23)9-17(18)30-20/h4-9,25H,1-3H3
SMILES	CC(=O)Oc1ccc(cc1)c1oc2cc(OC(=O)C)cc(c2c(=O)c1OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	412.08	Volume:	396.214 ? Van der Waals volume.
Dense:	1.04	LogP:	2.178 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.074 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.692 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	21.0
TPSA:	129.34 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	3.0
Heavy Atoms:	9.0

MedChem Properties

QED Drug-Likeness Score:	0.508	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.528	Fsp³:	0.143
MCE-18:	21.0 ? 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:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.113	Fluc inhibitor:	0.621 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.985 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.633 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.333	Promiscuous compounds:	0.306

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.943	MDCK Permeability:	-4.519
Pgp-inhibitor:	0.903	Pgp-substrate:	0.029
PAMPA:	0.364 ? 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):	0.28
20% Bioavailability (F20%):	0.163	30% Bioavailability (F30%):	0.911
50% Bioavailability (F50%):	0.95

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.516
Plasma Protein Binding (PPB):	86.796%	Volume Distribution (VD):	-0.36
Fu:	16.613% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.996
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.027
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.634	CYP1A2-substrate:	0.337
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.066
CYP2C9-inhibitor:	0.002	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.379
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.997 ? 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):

2.662

Half-life (T1/2):

0.557

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.105
Human Hepatotoxicity (H-HT):	0.311	Drug-induced Liver Injury (DILI):	0.989
AMES Toxicity:	0.485	Rat Oral Acute Toxicity:	0.663
Maximum Recommended Daily Dose:	0.343	Skin Sensitization:	0.939
Carcinogencity:	0.183	Eye Corrosion:	0.545
Eye Irritation:	0.95	Respiratory Toxicity:	0.221
Drug-induced Neurotoxicity:	0.04	Ototoxicity:	0.04
Hematotoxicity:	0.358	Drug-induced Nephrotoxicity:	0.012
Genotoxicity:	0.976	RPMI-8226 Immunitoxicity:	0.021
A549 Cytotoxicity:	0.699	Hek293 Cytotoxicity:	0.192
BCF:	0.919 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.819 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.782 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.502 ? 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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12027740]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	antarctic	n.a.	PMID[15270575]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO26453	Prunus lusitanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37240175]
NPO25793	Gremmeniella abietina	Species	Helotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3346	Piper sanctum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25926	Tephrosia pumila	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26903	Plectranthus purpuratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26213	Tephrosia vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26625	Stichopus chloronotus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18292	Guarea trichilioides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26135	Walsura tubulata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26078	Mussaenda parviflora	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26163	Anisodus tanguticus	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25821	Delphinium cashmerianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26952	Cineraria geifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26289	Lecidella chodati	Species	Lecanoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26109	Pilocarpus spicatus	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11845	Petrorhagia dubia	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26678	Calea pilosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25873	Thaminophyllum multiflorum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25717	Maytenus hookeri	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13781	Eremostachys moluccelloides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26026	Vitis silvestris	Species	Vitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26563	Alectoria japonica	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26453	Prunus lusitanica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29051	Ranunculus acris	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18292	Guarea trichilioides	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26535	Balanus glandula	Species	Balanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26352	Heuchera cylindrica	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26625	Stichopus chloronotus	Species	Stichopodidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26754	Stevia connata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25952	Lastrea thelypteris	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14466	Penicillium olsonii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26213	Tephrosia vogelii	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2344	Carlina acanthifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27252	Iochroma australe	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26430	Aplysina laevis	Species	Aplysinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25741	Aster ageratoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26884	Helichrysum davenportii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27377	Diaporthe helianthi	Species	Diaporthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25793	Gremmeniella abietina	Species	Helotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26053	Pluchea suaveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26980	Halocarpus biformis	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26903	Plectranthus purpuratus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2039	Callerya cinerea	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26782	Dendrilla membranosa	Species	Darwinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7214	Bufotes viridis	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26186	Stereocaulon leprocauloides	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26377	Amelanchier vulgaris	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24378	Osmanthus heterophyllus	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25849	Streptomyces lomondensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO3346	Piper sanctum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26408	Melanophryniscus moreirae	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26727	Eremocarpus setiger	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25926	Tephrosia pumila	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19823	Vicia benghalensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25997	Senecio rupestris	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO137	Nepeta multifida	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26244	Panax papyrifer	Species	Araliaceae	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
Activity	3
IC50	2
GI	3

Activity Type	# Activity
Cell line	3
Organism	4
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
NPT839	Cell line	L6	Rattus norvegicus	Activity	=	94.8	%	PMID[25659770]
NPT839	Cell line	L6	Rattus norvegicus	Activity	=	90.2	%	PMID[25659770]
NPT319	Cell line	B16	Mus musculus	IC50	=	39800.0	nM	PMID[25659770]
NPT1225	Organism	Plasmodium falciparum (isolate FcB1 / Columbia)	Plasmodium falciparum FcB1/Columbia	GI	=	7.6	%	PMID[25659770]
NPT2229	Organism	Trypanosoma brucei gambiense	Trypanosoma brucei gambiense	GI	=	5.6	%	PMID[25659770]
NPT2229	Organism	Trypanosoma brucei gambiense	Trypanosoma brucei gambiense	GI	=	0.0	%	PMID[25659770]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	>	100.0	uM	PMID[25659770]
NPT634	Organism	Leishmania amazonensis	Leishmania amazonensis	IC50	=	12270.0	nM	PMID[25659770]

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
-	Artemia	LC50	=	2210000.0	nM	PMID[16378372]

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 NPC153758 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	26820
0.1-0.2	19953
0.2-0.3	2195
0.3-0.4	679
0.4-0.5	174
0.5-0.6	26
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
0.7547	Intermediate Similarity	NPC262094
0.6786	Remote Similarity	NPC146679
0.6607	Remote Similarity	NPC103904
0.6552	Remote Similarity	NPC270620
0.6441	Remote Similarity	NPC236769
0.6316	Remote Similarity	NPC474037
0.6207	Remote Similarity	NPC188871
0.5938	Remote Similarity	NPC99671
0.5932	Remote Similarity	NPC76376
0.5806	Remote Similarity	NPC78326
0.5667	Remote Similarity	NPC59951
0.5667	Remote Similarity	NPC110070
0.5645	Remote Similarity	NPC58382
0.5645	Remote Similarity	NPC206604
0.5588	Remote Similarity	NPC473241
0.5574	Remote Similarity	NPC605569
0.5556	Remote Similarity	NPC289667
0.55	Remote Similarity	NPC29353
0.541	Remote Similarity	NPC32557
0.5342	Remote Similarity	NPC249281
0.5323	Remote Similarity	NPC100916
0.5246	Remote Similarity	NPC203891
0.5238	Remote Similarity	NPC200740
0.5238	Remote Similarity	NPC470216
0.5238	Remote Similarity	NPC246204
0.5238	Remote Similarity	NPC200388
0.52	Remote Similarity	NPC46420
0.5156	Remote Similarity	NPC55619
0.5156	Remote Similarity	NPC223579
0.5077	Remote Similarity	NPC177839
0.5067	Remote Similarity	NPC297987
0.5065	Remote Similarity	NPC611303
0.5063	Remote Similarity	NPC276377

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC153758 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4904
0.1-0.2	4154
0.2-0.3	82
0.3-0.4	8
0.4-0.5	2
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