NPASS Compound

Natural Product: NPC120952

Natural Product ID	NPC120952
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Diosmetin-7-O-Beta-D-Glucopyranosyl-(1->2)-6-O-Acetyl-Beta-D-Glucopyranosyl-(1->2)-[Alpha-Lrhamnopyranosyl-(1->6)]-Beta-D-Glucopyranoside
IUPAC Name	[(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-3-yl]oxy-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2336743
PubChem CID	71717056
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 2D 122128 0 0 0 0 0 0 0 0999 V2000 -0.8886 1.5391 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 0.2401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 -1.0590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -2.5362 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 -3.0492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3086 -4.3483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0586 -5.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -6.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1491 -6.1603 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -7.4594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -5.1962 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -7.7942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 -6.4952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -7.0082 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 -8.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2709 -9.4496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1386 -8.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6386 -8.9366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5209 -10.7487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1700 -9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9200 -11.0835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4200 -11.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1595 -12.5607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3086 -13.5249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 -14.8239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7181 -13.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9786 -11.5347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8296 -10.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0796 -9.2714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7286 -10.2356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2181 -13.0119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 -7.6375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5377 -8.6017 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9472 -8.0887 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2077 -6.6115 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9577 -5.3124 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4472 -8.0887 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2877 -9.9008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0377 -11.1998 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2877 -12.4988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7877 -12.4988 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0377 -13.7979 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2077 -2.0850 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9472 -0.6078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5377 -0.0948 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2877 1.2042 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4472 -0.6078 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9577 -3.3841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6114 1.5391 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8365 1.1428 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3396 -0.5099 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9791 -1.5720 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0776 -3.7109 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0776 -4.9856 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3886 -4.6831 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3056 -8.0709 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -5.5310 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4039 -7.3105 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4888 -7.6114 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7500 -3.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5000 -2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 4.0981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0000 1.0981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2831 -8.2862 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0167 -10.2494 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -10.4138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0520 -10.3785 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2709 -12.0477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3679 -8.8817 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2967 -10.4426 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3415 -9.5856 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1595 -14.4891 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 -16.1230 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7596 -15.5739 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4394 -14.2379 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1567 -14.4463 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3882 -12.0477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9786 -9.6063 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2453 -8.3276 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2286 -10.2356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9681 -14.3109 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5147 -9.6988 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3858 -9.5231 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6172 -7.1245 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4577 -5.3124 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1972 -9.3877 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6684 -9.3147 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0897 -10.8035 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7877 -15.0969 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7386 -14.5479 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3367 -13.0479 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6172 -1.5720 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2077 0.8694 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5147 1.0023 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5377 2.5033 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1972 0.6912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4577 -3.3841 0.0000 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 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 1 0 15 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 21 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 28 32 1 0 32 33 1 0 11 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 36 39 1 0 35 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 46 51 1 0 8 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 58 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 5 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 64 67 1 0 63 68 1 0 65 3 1 0 55 7 1 0 37 10 1 0 48 42 1 0 19 13 1 0 30 25 1 0 23 17 1 0 1 69 1 0 2 70 1 0 2 71 1 0 3 72 1 6 5 73 1 6 7 74 1 6 8 75 1 1 10 76 1 6 11 77 1 1 14 78 1 0 16 79 1 0 19 80 1 0 22 81 1 0 26 82 1 0 27 83 1 0 30 84 1 0 31 85 1 0 33 86 1 0 33 87 1 0 33 88 1 0 35 89 1 1 36 90 1 6 37 91 1 1 38 92 1 0 39 93 1 0 40 94 1 0 40 95 1 0 42 96 1 6 44 97 1 1 45 98 1 0 45 99 1 0 45100 1 0 46101 1 6 47102 1 1 48103 1 1 49104 1 0 50105 1 0 51106 1 0 53107 1 1 54108 1 6 55109 1 1 56110 1 0 57111 1 0 58112 1 0 58113 1 0 62114 1 0 62115 1 0 62116 1 0 63117 1 1 64118 1 6 65119 1 1 66120 1 0 67121 1 0 68122 1 0 M END

Standard InCHIKey	BHUVDLGITGTMAI-KOZHEFPZSA-N
Standard InCHI	InChI=1S/C42H54O26/c1-13-27(48)31(52)35(56)39(61-13)60-12-25-30(51)33(54)37(41(65-25)62-16-7-18(46)26-19(47)9-21(63-22(26)8-16)15-4-5-20(58-3)17(45)6-15)68-42-38(34(55)29(50)24(66-42)11-59-14(2)44)67-40-36(57)32(53)28(49)23(10-43)64-40/h4-9,13,23-25,27-43,45-46,48-57H,10-12H2,1-3H3/t13-,23+,24+,25+,27-,28+,29+,30+,31+,32-,33-,34-,35+,36+,37+,38+,39+,40-,41+,42-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@H](O[C@H]3[C@H](Oc4cc(O)c5c(c4)oc(cc5=O)c4ccc(c(c4)O)OC)O[C@@H]([C@H]([C@@H]3O)O)CO[C@@H]3O[C@@H](C)[C@@H]([C@H]([C@H]3O)O)O)O[C@@H]([C@H]([C@@H]2O)O)COC(=O)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	974.29	Volume:	879.91 ? Van der Waals volume.
Dense:	1.107	LogP:	-1.801 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.397 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.921 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	43.0
TPSA:	402.57 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.067	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.014	Fsp³:	0.619
MCE-18:	183.0 ? 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:	1
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.616	Fluc inhibitor:	0.442 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.827 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.5 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.246	Promiscuous compounds:	0.419

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.611	MDCK Permeability:	-5.059
Pgp-inhibitor:	0.0	Pgp-substrate:	0.89
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):	1.0
20% Bioavailability (F20%):	0.783	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.015
Plasma Protein Binding (PPB):	71.695%	Volume Distribution (VD):	-0.241
Fu:	26.66% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.047
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):

0.179

Half-life (T1/2):

5.916

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.445	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.992	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.025	Eye Corrosion:	0.0
Eye Irritation:	0.002	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.239	Drug-induced Nephrotoxicity:	0.874
Genotoxicity:	0.65	RPMI-8226 Immunitoxicity:	0.348
A549 Cytotoxicity:	0.686	Hek293 Cytotoxicity:	0.361
BCF:	0.308 ? 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:	2.79 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.603 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.736 ? 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
NPO32535	dracocephalum ruyschiana	Species	Lamiaceae	Eukaryota	aerial parts	Mongolian	n.a.	PMID[23356964]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	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
NPT1	Others	Radical scavenging activity	n.a.	IC50	>	200.0	ug.mL-1	PMID[2853205]

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 NPC120952 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	18716
0.1-0.2	26153
0.2-0.3	4132
0.3-0.4	549
0.4-0.5	224
0.5-0.6	54
0.6-0.7	16
0.7-0.8	1
0.8-0.85	1
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9293	High Similarity	NPC198199
0.9	High Similarity	NPC68592
0.8544	High Similarity	NPC298666
0.8333	Intermediate Similarity	NPC311850
0.7941	Intermediate Similarity	NPC11468
0.75	Intermediate Similarity	NPC262222
0.7353	Intermediate Similarity	NPC209296
0.7248	Intermediate Similarity	NPC488083
0.7064	Intermediate Similarity	NPC473644
0.6964	Remote Similarity	NPC488086
0.6937	Remote Similarity	NPC488087
0.6731	Remote Similarity	NPC115674
0.6729	Remote Similarity	NPC195257
0.6476	Remote Similarity	NPC22062
0.6476	Remote Similarity	NPC65003
0.6476	Remote Similarity	NPC473634
0.6476	Remote Similarity	NPC138811
0.6436	Remote Similarity	NPC22832
0.6346	Remote Similarity	NPC8856
0.6316	Remote Similarity	NPC480441
0.6316	Remote Similarity	NPC25523
0.6293	Remote Similarity	NPC488088
0.6273	Remote Similarity	NPC475382
0.6182	Remote Similarity	NPC142142
0.6168	Remote Similarity	NPC210073
0.5926	Remote Similarity	NPC44931
0.581	Remote Similarity	NPC80188
0.5752	Remote Similarity	NPC479766
0.5739	Remote Similarity	NPC135358
0.5625	Remote Similarity	NPC240306
0.5614	Remote Similarity	NPC488089
0.5603	Remote Similarity	NPC602448
0.5577	Remote Similarity	NPC95090
0.5577	Remote Similarity	NPC27408
0.5526	Remote Similarity	NPC473623
0.552	Remote Similarity	NPC209550
0.547	Remote Similarity	NPC253685
0.5398	Remote Similarity	NPC204693
0.5378	Remote Similarity	NPC89052
0.537	Remote Similarity	NPC243930
0.537	Remote Similarity	NPC486578
0.5321	Remote Similarity	NPC311830
0.5321	Remote Similarity	NPC607707
0.5315	Remote Similarity	NPC251417
0.5283	Remote Similarity	NPC189142
0.5283	Remote Similarity	NPC77660
0.5278	Remote Similarity	NPC285197
0.5263	Remote Similarity	NPC122809
0.5259	Remote Similarity	NPC32641
0.5259	Remote Similarity	NPC256188
0.5259	Remote Similarity	NPC35119
0.5254	Remote Similarity	NPC101636
0.5229	Remote Similarity	NPC605067
0.5221	Remote Similarity	NPC67105
0.5217	Remote Similarity	NPC46202
0.5189	Remote Similarity	NPC19709
0.5179	Remote Similarity	NPC239549
0.5172	Remote Similarity	NPC12013
0.5172	Remote Similarity	NPC65711
0.5172	Remote Similarity	NPC11432
0.5172	Remote Similarity	NPC477613
0.5167	Remote Similarity	NPC14187
0.5164	Remote Similarity	NPC173837
0.5138	Remote Similarity	NPC191306
0.5138	Remote Similarity	NPC611303
0.5128	Remote Similarity	NPC122467
0.5128	Remote Similarity	NPC473327
0.5116	Remote Similarity	NPC192539
0.5091	Remote Similarity	NPC601144
0.5088	Remote Similarity	NPC275454
0.5088	Remote Similarity	NPC227508
0.5052	Remote Similarity	NPC223579
0.5047	Remote Similarity	NPC261866
0.5047	Remote Similarity	NPC39360
0.5047	Remote Similarity	NPC29763
0.5047	Remote Similarity	NPC210003
0.5041	Remote Similarity	NPC244875
0.5038	Remote Similarity	NPC199172
0.5038	Remote Similarity	NPC473554

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC120952 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5282
0.1-0.2	3800
0.2-0.3	58
0.3-0.4	5
0.4-0.5	3
0.5-0.6	1
0.6-0.7	0
0.7-0.8	1
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
0.7353	Intermediate Similarity	NPD7054	Phase 4
0.5913	Remote Similarity	NPD7472	Pre-clinical

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