NPASS Compound

Natural Product: NPC182814

Natural Product ID	NPC182814
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lonijaposide O
IUPAC Name	(2S)-2-[3-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,4-dihydro-2H-pyran-4-yl]ethenyl]pyridin-1-ium-1-yl]propanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3092662
PubChem CID	76335387
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

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 65 67 0 0 0 0 0 0 0 0999 V2000 -0.7125 -3.6562 -0.0922 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2889 -2.4248 0.0294 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9841 -1.2817 -0.6752 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5540 -0.3473 0.3419 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8304 0.8952 0.3752 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5426 1.5328 -0.8229 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0994 0.7727 -1.8081 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0578 -0.6733 -1.5768 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4457 -1.0029 -1.1049 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3330 -0.1144 -0.7613 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6774 -0.4057 -0.3032 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1529 -1.6925 -0.1827 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4456 -1.9178 0.2597 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2497 -0.8567 0.5770 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7924 0.3941 0.4618 N 0 0 0 0 0 4 0 0 0 0 0 0 4.5451 0.6057 0.0347 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6076 1.5523 0.7868 C 0 0 2 0 0 0 0 0 0 0 0 0 7.9245 1.1690 1.3330 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9704 1.4617 0.7090 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0233 0.4918 2.5225 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9011 2.4573 1.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2297 1.3418 -3.0979 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0861 2.5751 -3.2659 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6953 0.5820 -4.1508 O 0 0 0 0 0 1 0 0 0 0 0 0 -2.8736 0.0063 0.0786 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7479 -0.2564 1.1027 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6762 -1.1749 0.6975 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5952 -0.7429 -0.2184 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0382 -0.4024 -1.5719 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4294 -1.4948 -2.1425 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3985 0.3812 0.3561 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.5354 1.4888 0.8642 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3555 1.0074 1.6669 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7218 0.8792 2.9987 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0969 2.3510 -0.1395 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1828 -0.0990 1.4023 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1983 -4.4546 0.4215 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5691 -3.9134 -0.6949 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5668 -2.1298 0.6267 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7761 -1.7240 -1.3213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4414 -0.7856 1.3537 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6503 2.5870 -1.0123 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0111 -1.1824 -2.5807 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6948 -2.0496 -1.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0202 0.9316 -0.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5527 -2.5463 -0.4221 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8668 -2.9139 0.3718 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2628 -1.0351 0.9235 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1823 1.6346 -0.0556 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7451 2.1563 -0.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8717 0.0578 2.8708 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8234 3.4985 1.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8756 2.0587 1.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3903 2.4336 2.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1819 -0.7209 1.9629 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3132 -1.5989 -0.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9347 -0.1678 -2.2185 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4243 0.5037 -1.5932 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6622 -1.1403 -2.6960 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0802 0.8237 -0.4225 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1544 2.1103 1.5562 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5701 1.7911 1.6181 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6363 0.5537 3.1212 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8539 2.5345 -0.7612 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8692 -0.7142 1.0121 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 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 15 17 1 0 17 18 1 0 18 19 2 0 18 20 1 0 17 21 1 0 7 22 1 0 22 23 2 0 22 24 1 0 4 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 32 35 1 0 31 36 1 0 8 3 1 0 16 11 1 0 33 26 1 0 1 37 1 0 1 38 1 0 2 39 1 0 3 40 1 6 4 41 1 1 6 42 1 0 8 43 1 6 9 44 1 0 10 45 1 0 12 46 1 0 13 47 1 0 14 48 1 0 16 49 1 0 17 50 1 6 20 51 1 0 21 52 1 0 21 53 1 0 21 54 1 0 26 55 1 1 28 56 1 6 29 57 1 0 29 58 1 0 30 59 1 0 31 60 1 6 32 61 1 1 33 62 1 1 34 63 1 0 35 64 1 0 36 65 1 0 M CHG 2 15 1 24 -1 M END

Standard InCHIKey	NAPHCTLCUKYBIG-KMRSAXKXSA-N
Standard InCHI	InChI=1S/C24H29NO11/c1-3-14-15(7-6-13-5-4-8-25(9-13)12(2)21(30)31)16(22(32)33)11-34-23(14)36-24-20(29)19(28)18(27)17(10-26)35-24/h3-9,11-12,14-15,17-20,23-24,26-29H,1,10H2,2H3,(H-,30,31,32,33)/b7-6+/t12-,14+,15-,17+,18+,19-,20+,23-,24-/m0/s1
SMILES	C=C[C@H]1[C@@H](OC=C([C@H]1/C=C/c1ccc[n+](c1)[C@H](C(=O)O)C)C(=O)[O-])O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	507.17	Volume:	484.588 ? Van der Waals volume.
Dense:	1.047	LogP:	-0.918 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.308 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.705 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	22.0
TPSA:	189.92 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	5.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.181	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.441	Fsp³:	0.458
MCE-18:	79.514 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.597	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.008 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.352	Promiscuous compounds:	0.202

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.889	MDCK Permeability:	-5.465
Pgp-inhibitor:	0.0	Pgp-substrate:	0.209
PAMPA:	1.0 ? 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):	0.044
20% Bioavailability (F20%):	0.01	30% Bioavailability (F30%):	0.34
50% Bioavailability (F50%):	0.17

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.979
Plasma Protein Binding (PPB):	58.76%	Volume Distribution (VD):	-0.472
Fu:	40.475% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.945
OATP1B3 inhibitor:	0.98	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.257	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.001 ? 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):

1.332

Half-life (T1/2):

2.63

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.595	Drug-induced Liver Injury (DILI):	0.983
AMES Toxicity:	0.621	Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.143	Skin Sensitization:	1.0
Carcinogencity:	0.033	Eye Corrosion:	0.0
Eye Irritation:	0.403	Respiratory Toxicity:	0.015
Drug-induced Neurotoxicity:	0.017	Ototoxicity:	0.942
Hematotoxicity:	0.328	Drug-induced Nephrotoxicity:	0.976
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.063
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.03
BCF:	0.514 ? 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:	3.265 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.056 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.009 ? 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
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1002/elan.200403102]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[11077184]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11141124]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11735581]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15844965]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	PMID[17328234]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17602526]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower	n.a.	PMID[21804227]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	flower buds	Henan province, China	2005-MAY	PMID[21942812]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23265495]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[24279769]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3597	Rheedia acuminata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5155	Peritassa compta	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5155	Peritassa compta	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3699	Acacia aulacocarpa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3597	Rheedia acuminata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	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
Inhibition	1
IC50	1

Activity Type	# Activity
Organism	1
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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	63.2	%	PMID[24279769]
NPT339	Organism	Influenza A virus H3N2	Influenza A virus H3N2	IC50	=	11600.0	nM	PMID[24279769]

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 NPC182814 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	16375
0.1-0.2	30766
0.2-0.3	2536
0.3-0.4	147
0.4-0.5	18
0.5-0.6	2
0.6-0.7	7
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
0.8025	Intermediate Similarity	NPC318020
0.7647	Intermediate Similarity	NPC327373
0.7586	Intermediate Similarity	NPC160127
0.7586	Intermediate Similarity	NPC50997
0.7561	Intermediate Similarity	NPC325093
0.7386	Intermediate Similarity	NPC322043
0.6818	Remote Similarity	NPC329024
0.6559	Remote Similarity	NPC25442
0.6559	Remote Similarity	NPC12944
0.6556	Remote Similarity	NPC59033
0.6354	Remote Similarity	NPC111732
0.6237	Remote Similarity	NPC127647
0.602	Remote Similarity	NPC20593
0.5657	Remote Similarity	NPC317672
0.5146	Remote Similarity	NPC156044

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC182814 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3665
0.1-0.2	5382
0.2-0.3	103
0.3-0.4	0
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