NPASS Compound

Natural Product: NPC115674

Natural Product ID	NPC115674
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Lonicerin
IUPAC Name	7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5-hydroxychromen-4-one
Synonyms	7-Neohesperidosylluteolin; Lonicerin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL452979
PubChem CID	5282152
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-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 72 76 0 0 0 0 0 0 0 0999 V2000 -3.8262 1.5955 2.0311 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8398 0.1481 2.4776 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1628 -0.4666 2.0738 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0239 -1.9523 1.8071 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9287 -2.2400 0.7824 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1520 -0.9719 0.6062 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7669 -0.5271 1.8700 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0782 -1.0687 -0.2642 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1721 -0.2146 -1.3404 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9988 -0.8881 -2.6836 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2057 0.1491 -3.7549 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5659 1.4594 -3.4827 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3727 2.5269 -4.2351 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7798 3.7654 -4.1344 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5195 1.8476 -2.1746 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0674 0.8617 -1.2997 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9418 1.4274 -0.0534 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2012 1.3812 0.6986 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1792 2.0001 1.9549 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2850 1.9955 2.7652 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4654 1.3830 2.3809 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5722 1.3836 3.2028 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5548 1.9337 4.3212 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7122 0.7329 2.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7198 0.1307 1.4771 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9183 -0.5382 0.9898 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8806 -1.1349 -0.2784 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9788 -1.7851 -0.8007 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1644 -1.8791 -0.1016 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2110 -1.2960 1.1449 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0967 -0.6347 1.6783 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4007 -1.3875 1.8527 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2654 -2.5364 -0.6367 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6201 0.1832 0.7698 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5206 0.7662 1.1534 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3849 0.7833 0.3468 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 2.6013 4.0214 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6613 -0.3719 -4.9448 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8275 -1.9600 -2.8935 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4505 -2.7560 -0.3843 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2489 -2.3872 1.2874 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0377 -0.3343 3.1508 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1118 2.1426 2.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8456 2.0602 2.1150 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4741 1.6975 0.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7612 0.1275 3.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6232 0.0699 1.2159 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8567 -2.4533 2.7607 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2736 -3.0224 1.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8342 -0.1956 0.1821 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1233 0.3775 -1.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9089 -1.1805 -2.7328 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3091 0.2510 -3.9612 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5462 1.5011 -3.9453 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6120 2.2084 -5.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3494 2.5764 -3.6775 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0996 3.7993 -3.4203 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1762 0.3421 -1.6775 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7241 2.4869 2.2862 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5699 0.7344 3.3493 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9641 -1.0710 -0.8373 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9533 -2.2525 -1.7917 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1825 -0.1956 2.6559 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9893 -2.2106 1.8696 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1821 -2.0894 -0.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4673 0.2879 -0.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2567 2.0064 4.8626 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8494 -1.3510 -5.0338 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3480 -2.7793 -2.5521 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0198 -3.5154 -0.1551 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8890 -2.5180 2.0334 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6317 0.4406 3.0176 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 22 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 29 33 1 0 25 34 1 0 34 35 1 0 35 36 2 0 20 37 1 0 11 38 1 0 10 39 1 0 5 40 1 0 4 41 1 0 3 42 1 0 7 2 1 0 16 9 1 0 36 18 1 0 35 21 1 0 31 26 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 1 3 47 1 6 4 48 1 1 5 49 1 1 6 50 1 6 9 51 1 6 10 52 1 1 11 53 1 6 12 54 1 6 13 55 1 0 13 56 1 0 14 57 1 0 16 58 1 6 19 59 1 0 24 60 1 0 27 61 1 0 28 62 1 0 31 63 1 0 32 64 1 0 33 65 1 0 36 66 1 0 37 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	SHPPXMGVUDNKLV-KMFFXDMSSA-N
Standard InCHI	InChI=1S/C27H30O15/c1-9-20(33)22(35)24(37)26(38-9)42-25-23(36)21(34)18(8-28)41-27(25)39-11-5-14(31)19-15(32)7-16(40-17(19)6-11)10-2-3-12(29)13(30)4-10/h2-7,9,18,20-31,33-37H,8H2,1H3/t9-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1cc(c2c(=O)cc(c3ccc(c(c3)O)O)oc2c1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	0.844 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.222 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.62 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	249.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.149	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.705	Fsp³:	0.444
MCE-18:	119.436 ? 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:	1	PAINS Alert:	1
Colloidal aggregators:	0.639	Fluc inhibitor:	0.294 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.984 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.593 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.315	Promiscuous compounds:	0.509

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.533	MDCK Permeability:	-5.075
Pgp-inhibitor:	0.0	Pgp-substrate:	0.481
PAMPA:	0.999 ? 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):	0.998
20% Bioavailability (F20%):	0.979	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.206
Plasma Protein Binding (PPB):	78.872%	Volume Distribution (VD):	-0.132
Fu:	18.19% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.305
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.082
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.298
HLM stability:	0.025 ? 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):

1.927

Half-life (T1/2):

4.818

ADMET: Toxicity

hERG Blockers:	0.009	hERG Blockers (10um):	0.121
Human Hepatotoxicity (H-HT):	0.609	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.921	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.02	Skin Sensitization:	1.0
Carcinogencity:	0.128	Eye Corrosion:	0.0
Eye Irritation:	0.447	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.976
Hematotoxicity:	0.091	Drug-induced Nephrotoxicity:	0.572
Genotoxicity:	0.977	RPMI-8226 Immunitoxicity:	0.101
A549 Cytotoxicity:	0.764	Hek293 Cytotoxicity:	0.362
BCF:	0.413 ? 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:	2.985 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.513 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.672 ? 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]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2009.03.042]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.foodchem.2012.02.124]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jep.2005.01.054]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.3136/fstr.15.499]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB10.140]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.5897/AJB2010.000-3252]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
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]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17996677]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	Flower buds	n.a.	n.a.	PMID[18321056]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21377852]
NPO32732	Pterospermum acerifolium	Species	Malvaceae	Eukaryota	flowers	n.a.	n.a.	PMID[21719287]
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]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	flower bud	n.a.	PMID[22822669]
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]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	Tongxiang, China	n.a.	PMID[24621197]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26214875]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	Flowers	n.a.	n.a.	PMID[28248102]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31181920]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31418264]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35143705]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36378844]
NPO16926	Thymbra capitata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36557924]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37049761]
NPO16926	Thymbra capitata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37111149]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38139796]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38498554]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38754641]
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]
NPO471	Ardisia neriifolia	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6237	Cryptocarya aschersoniana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5196	Eupatorium argentinum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19948	Neolentinus lepideus	Species	Gloeophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5155	Peritassa compta	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4823	Psiadia dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3597	Rheedia acuminata	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6092	Symphyocladia latiuscula	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1899	Aria rostellata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5641	Dendroctonus frontalis	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2832	Hazunta membranacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6604	Melanothamnus afaqhusainii	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO978	Panzerina lanata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4728	Streptomyces tsukubensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4706	Streptomyces vinaceusdrappus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16926	Thymbra capitata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7569	Guatteria boliviana	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8418	Anemone flaccida	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30003	Lonicera confuse	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[TCM_Taiwan]
NPO29846	Lonicera dasystyla	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1515	Lonicera japonica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4596	Lonicera confusa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3853	Aspidosperma subincanum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6729	Juniperus brevifolia	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO978	Panzerina lanata	Species	Lamiaceae	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]
NPO21345	Lonicera hypoglauca	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2476	Lonicera fulvotomentosa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17752	Mentha X piperita	Strain	Lamiaceae	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]
NPO20440	Chrysanthemum x morifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6604	Melanothamnus afaqhusainii	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5641	Dendroctonus frontalis	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25094	Artemisia princeps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2832	Hazunta membranacea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10492	Artemisia montana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18671	Saussurea involucrata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4728	Streptomyces tsukubensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO28276	Artemisia argyi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16926	Thymbra capitata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1899	Aria rostellata	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4706	Streptomyces vinaceusdrappus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17072	Lonicera macranthoides	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24093	Drynaria fortunei	Species	Polypodiaceae	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
NPO16926	Thymbra capitata	Post-distilled extract	n.a.	7.10 Â± 1.61	n.a.	n.a.	mg/g	PMID[36557924]
NPO16926	Thymbra capitata	Post-distilled extract	n.a.	7.25 Â± 1.24	n.a.	n.a.	mg/g	PMID[36557924]
NPO17752	Mentha X piperita	Other	Leaf	12	12	12	mg/100g	Database [DUKE]
NPO17752	Mentha X piperita	Dried Or Powder	n.a.	1170.351852	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO319	Citrus limon	Beverage (juice)	n.a.	1.850000024	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]

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	2

Activity Type	# Activity
Individual protein	2
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1310	Individual protein	Xanthine dehydrogenase	Bos taurus	Inhibition	=	20.1	%	PMID[3379415]
NPT967	Individual protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	11900.0	nM	PMID[9461655]

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.	IC50	=	2370.0	nM	PMID[9461655]

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 NPC115674 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	22479
0.1-0.2	22941
0.2-0.3	3520
0.3-0.4	501
0.4-0.5	284
0.5-0.6	77
0.6-0.7	36
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9231	High Similarity	NPC8856
0.8889	High Similarity	NPC65003
0.8276	Intermediate Similarity	NPC195257
0.7692	Intermediate Similarity	NPC253685
0.7407	Intermediate Similarity	NPC19709
0.7317	Intermediate Similarity	NPC189142
0.7317	Intermediate Similarity	NPC77660
0.71	Intermediate Similarity	NPC198199
0.7065	Intermediate Similarity	NPC32641
0.7065	Intermediate Similarity	NPC256188
0.7041	Intermediate Similarity	NPC311850
0.7033	Intermediate Similarity	NPC240306
0.7	Intermediate Similarity	NPC210073
0.6931	Remote Similarity	NPC298666
0.6915	Remote Similarity	NPC475382
0.6882	Remote Similarity	NPC35119
0.6854	Remote Similarity	NPC606546
0.6739	Remote Similarity	NPC122809
0.6731	Remote Similarity	NPC120952
0.6667	Remote Similarity	NPC68592
0.663	Remote Similarity	NPC155877
0.66	Remote Similarity	NPC480441
0.6591	Remote Similarity	NPC80188
0.6531	Remote Similarity	NPC14187
0.6471	Remote Similarity	NPC473043
0.6471	Remote Similarity	NPC331652
0.6465	Remote Similarity	NPC11468
0.6395	Remote Similarity	NPC39360
0.6395	Remote Similarity	NPC29763
0.6395	Remote Similarity	NPC210003
0.6275	Remote Similarity	NPC473644
0.6264	Remote Similarity	NPC190003
0.6224	Remote Similarity	NPC473071
0.6222	Remote Similarity	NPC22832
0.617	Remote Similarity	NPC44931
0.617	Remote Similarity	NPC163242
0.617	Remote Similarity	NPC272068
0.6154	Remote Similarity	NPC488083
0.6154	Remote Similarity	NPC605784
0.6147	Remote Similarity	NPC262222
0.6136	Remote Similarity	NPC95090
0.6136	Remote Similarity	NPC27408
0.6117	Remote Similarity	NPC25523
0.6044	Remote Similarity	NPC601144
0.6023	Remote Similarity	NPC261866
0.6023	Remote Similarity	NPC238376
0.6022	Remote Similarity	NPC254855
0.6022	Remote Similarity	NPC94610
0.602	Remote Similarity	NPC209296
0.598	Remote Similarity	NPC25724
0.5978	Remote Similarity	NPC311830
0.5955	Remote Similarity	NPC277205
0.5955	Remote Similarity	NPC37919
0.5938	Remote Similarity	NPC22062
0.5938	Remote Similarity	NPC473634
0.5938	Remote Similarity	NPC138811
0.5918	Remote Similarity	NPC65711
0.587	Remote Similarity	NPC243930
0.5851	Remote Similarity	NPC95866
0.5833	Remote Similarity	NPC78734
0.5833	Remote Similarity	NPC67105
0.58	Remote Similarity	NPC142142
0.5789	Remote Similarity	NPC239549
0.5778	Remote Similarity	NPC136042
0.5743	Remote Similarity	NPC220173
0.5741	Remote Similarity	NPC488086
0.5714	Remote Similarity	NPC58716
0.5714	Remote Similarity	NPC84362
0.5714	Remote Similarity	NPC470444
0.5714	Remote Similarity	NPC45638
0.5657	Remote Similarity	NPC64425
0.5652	Remote Similarity	NPC201292
0.5638	Remote Similarity	NPC116458
0.5638	Remote Similarity	NPC246943
0.5638	Remote Similarity	NPC607707
0.5612	Remote Similarity	NPC3583
0.5604	Remote Similarity	NPC168822
0.5591	Remote Similarity	NPC20505
0.5579	Remote Similarity	NPC170052
0.5579	Remote Similarity	NPC135846
0.5556	Remote Similarity	NPC488087
0.5545	Remote Similarity	NPC229409
0.5543	Remote Similarity	NPC271692
0.55	Remote Similarity	NPC108406
0.5484	Remote Similarity	NPC27942
0.5417	Remote Similarity	NPC476215
0.5413	Remote Similarity	NPC255799
0.54	Remote Similarity	NPC257566
0.54	Remote Similarity	NPC255157
0.54	Remote Similarity	NPC259896
0.5392	Remote Similarity	NPC122467
0.5392	Remote Similarity	NPC150767
0.5391	Remote Similarity	NPC199172
0.5376	Remote Similarity	NPC181712
0.5361	Remote Similarity	NPC294629
0.5361	Remote Similarity	NPC131407
0.5345	Remote Similarity	NPC35924
0.534	Remote Similarity	NPC472991
0.5333	Remote Similarity	NPC484301
0.5333	Remote Similarity	NPC602448
0.5327	Remote Similarity	NPC473072
0.5326	Remote Similarity	NPC249281
0.5326	Remote Similarity	NPC108831
0.5326	Remote Similarity	NPC182634
0.5312	Remote Similarity	NPC136761
0.5306	Remote Similarity	NPC473682
0.5306	Remote Similarity	NPC251417
0.53	Remote Similarity	NPC607513
0.5269	Remote Similarity	NPC297987
0.5269	Remote Similarity	NPC323593
0.5269	Remote Similarity	NPC203500
0.5238	Remote Similarity	NPC101636
0.52	Remote Similarity	NPC227508
0.5196	Remote Similarity	NPC606547
0.5189	Remote Similarity	NPC135358
0.5161	Remote Similarity	NPC289667
0.5161	Remote Similarity	NPC143851
0.5155	Remote Similarity	NPC220169
0.513	Remote Similarity	NPC209550
0.5104	Remote Similarity	NPC191306
0.5104	Remote Similarity	NPC285197
0.51	Remote Similarity	NPC605855
0.5098	Remote Similarity	NPC186816
0.5091	Remote Similarity	NPC164704
0.5053	Remote Similarity	NPC46420
0.505	Remote Similarity	NPC275454

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC115674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5674
0.1-0.2	3391
0.2-0.3	74
0.3-0.4	5
0.4-0.5	4
0.5-0.6	1
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.602	Remote Similarity	NPD7054	Phase 4
0.5288	Remote Similarity	NPD7251	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data