NPASS Compound

Natural Product: NPC229036

Natural Product ID	NPC229036
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	6-O-Galloyl-D-Glucose
IUPAC Name	[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL518124
PubChem CID	5317463
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002279] Benzene and substituted derivatives [CHEMONTID:0000176] Benzoic acids and derivatives [CHEMONTID:0001248] Hydroxybenzoic acid derivatives [CHEMONTID:0001251] Gallic acid and derivatives [CHEMONTID:0003539] Galloyl 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 39 40 0 0 0 0 0 0 0 0999 V2000 -2.3690 -0.7389 2.6708 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6851 -0.6167 1.3117 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7908 0.2197 0.6438 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8631 -0.0519 -0.6877 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8539 0.5647 -1.5824 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4729 0.2749 -1.3798 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1552 0.5954 -0.2426 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5634 1.1923 0.6814 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5872 0.2598 -0.0574 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2283 -0.3936 -1.0729 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5531 -0.7285 -0.9548 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2110 -1.3885 -1.9743 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2252 -0.3909 0.2133 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5717 0.2680 1.2330 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2411 0.5954 1.0949 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2019 0.6253 2.4174 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5563 -0.7002 0.3914 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2351 0.4027 -1.1863 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0893 0.8854 -0.0338 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0742 -0.0671 1.1268 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.9716 -1.1079 0.8298 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6212 2.1568 0.3337 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8306 -0.6488 -1.8692 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2845 -1.6927 2.8754 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6594 -1.6173 0.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7731 -1.1680 -0.7923 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0817 1.6568 -1.6392 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1021 0.1904 -2.6270 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6707 -0.6475 -1.9850 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5137 -2.3685 -1.8902 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6840 1.1141 1.8702 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5961 1.5441 2.5523 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2468 -0.4672 -0.3209 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1525 1.2530 -1.8939 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1133 1.0440 -0.4533 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4298 0.4131 2.0391 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5554 -1.9963 1.0479 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1359 2.1038 1.1984 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6069 -0.5693 -2.8278 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 2 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 11 13 2 0 13 14 1 0 14 15 2 0 14 16 1 0 13 17 1 0 4 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 19 22 1 0 18 23 1 0 20 2 1 0 15 9 1 0 1 24 1 0 2 25 1 6 4 26 1 1 5 27 1 0 5 28 1 0 10 29 1 0 12 30 1 0 15 31 1 0 16 32 1 0 17 33 1 0 18 34 1 6 19 35 1 6 20 36 1 1 21 37 1 0 22 38 1 0 23 39 1 0 M END

Standard InCHIKey	VGVDLJNNDOFWKT-JEUROIALSA-N
Standard InCHI	InChI=1S/C13H16O10/c14-5-1-4(2-6(15)8(5)16)12(20)22-3-7-9(17)10(18)11(19)13(21)23-7/h1-2,7,9-11,13-19,21H,3H2/t7-,9-,10+,11-,13-/m1/s1
SMILES	O[C@@H]1O[C@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	332.07	Volume:	293.648 ? Van der Waals volume.
Dense:	1.131	LogP:	-1.103 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.107 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.207 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	13.0
TPSA:	177.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	7.0	Rings:	2.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.236	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.739	Fsp³:	0.462
MCE-18:	56.421 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	1
Colloidal aggregators:	0.399	Fluc inhibitor:	0.11 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.137 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.036 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.323	Promiscuous compounds:	0.697

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.452	MDCK Permeability:	-5.045
Pgp-inhibitor:	0.0	Pgp-substrate:	0.055
PAMPA:	0.996 ? 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):	0.068
20% Bioavailability (F20%):	0.884	30% Bioavailability (F30%):	0.988
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.012	MRP1:	0.987
Plasma Protein Binding (PPB):	48.744%	Volume Distribution (VD):	-0.45
Fu:	48.89% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.635
BSEP inhibitor:	0.01

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.004
CYP2C9-inhibitor:	0.007	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.021
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.338
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.997
HLM stability:	0.021 ? 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):

2.584

Half-life (T1/2):

2.467

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.656
Human Hepatotoxicity (H-HT):	0.103	Drug-induced Liver Injury (DILI):	0.777
AMES Toxicity:	0.685	Rat Oral Acute Toxicity:	0.027
Maximum Recommended Daily Dose:	0.122	Skin Sensitization:	0.999
Carcinogencity:	0.103	Eye Corrosion:	0.005
Eye Irritation:	0.973	Respiratory Toxicity:	0.021
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.944
Hematotoxicity:	0.005	Drug-induced Nephrotoxicity:	0.068
Genotoxicity:	0.601	RPMI-8226 Immunitoxicity:	0.013
A549 Cytotoxicity:	0.664	Hek293 Cytotoxicity:	0.059
BCF:	0.237 ? 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:	2.77 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.171 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.594 ? 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
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10978210]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19012276]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25593390]
NPO31224	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[7513748]
NPO18287	Penicillium bilaiae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10359	Chaiturus marrubiastrum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19818	Jacquemontia paniculata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14248	Mandragora autumnalis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20223	Rosa pomifera	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22675	Helichrysum chionosphaerum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19037	Senecio praecox	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20422	Albizia myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26393.1	Petunia integrifolia subsp. inflata	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20753	Grangea maderaspatana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13454	Amphorogyne spicata	Species	Amphorogynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18144	Metrodorea nigra	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16142	Verbascum thapsiforme	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15422	Carduus tenuiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31224	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13754	Tanacetum coccineum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31224	Sapium sebiferum	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19996	Caulerpa peltata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14932.1	Dalbergia lanceolaria subsp. paniculata	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21564	Senecio behnii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18144	Metrodorea nigra	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19037	Senecio praecox	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17856	Anaphalis lactea	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20881	Rheum officinale	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12108	Aizopsis selskiana	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13754	Tanacetum coccineum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19512	Gleichenia quadripartita	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16572	Rhododendron dahuricum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21691	Dillenia indica	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20144	Lespedeza tomentosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21244	Delphinium nuttallianum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13454	Amphorogyne spicata	Species	Amphorogynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11580	Onobrychis arenaria	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20560	Polyporus betulinus	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19818	Jacquemontia paniculata	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17018	Salvia greggii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20625	Delphinium virgatum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21376	Lupinus corymbosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18867	Stephanitis takeyai	Species	Tingidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14800	Oophaga granulifera	Species	Dendrobatidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26393.1	Petunia integrifolia subsp. inflata	Subspecies	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10216	Leptocereus quadricostatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19671	Dipsacus azureus	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22675	Helichrysum chionosphaerum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15422	Carduus tenuiflorus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19395	Nepeta granatensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20223	Rosa pomifera	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20753	Grangea maderaspatana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16142	Verbascum thapsiforme	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24407	Bipolaris heveae	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18287	Penicillium bilaiae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17336	Benincasa hispida	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21112	Chaetomium carinthiacum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17568	Balanophora laxiflora	Species	Balanophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2228	Photinia serratifolia	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20353	Degenia velebitica	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20947	Tagetes filifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10359	Chaiturus marrubiastrum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20422	Albizia myriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27737	Penicillium shearii	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19913	Rhynchophorus ferrugineus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26917	Quercus rubra	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20490	Erythrophleum ivorense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20844	Sphaerella rosigena	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19232	Anchusa azurea	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13246	Pinalia stricta	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14248	Mandragora autumnalis	Species	Solanaceae	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	2

Activity Type	# Activity
Organism	2

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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	29.6	mmHg	PMID[7513748]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	17.3	mmHg	PMID[7513748]

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 NPC229036 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	17035
0.1-0.2	30620
0.2-0.3	1975
0.3-0.4	144
0.4-0.5	57
0.5-0.6	17
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
0.6735	Remote Similarity	NPC225036
0.6667	Remote Similarity	NPC482667
0.6538	Remote Similarity	NPC120621
0.6226	Remote Similarity	NPC92117
0.62	Remote Similarity	NPC226738
0.6038	Remote Similarity	NPC75945
0.5636	Remote Similarity	NPC44260
0.5574	Remote Similarity	NPC484156
0.5556	Remote Similarity	NPC190587
0.5536	Remote Similarity	NPC61152
0.5536	Remote Similarity	NPC125546
0.5455	Remote Similarity	NPC239019
0.5455	Remote Similarity	NPC247629
0.5397	Remote Similarity	NPC166277
0.5312	Remote Similarity	NPC472859
0.5312	Remote Similarity	NPC117668
0.5231	Remote Similarity	NPC25389
0.5231	Remote Similarity	NPC1913
0.5179	Remote Similarity	NPC142528
0.5167	Remote Similarity	NPC476873
0.5111	Remote Similarity	NPC1321
0.5085	Remote Similarity	NPC172419
0.5075	Remote Similarity	NPC475058

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC229036 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4524
0.1-0.2	4547
0.2-0.3	70
0.3-0.4	6
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