NPASS Compound

Natural Product: NPC295625

Natural Product ID	NPC295625
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-Beta-D-(2-O-Feruloyl)Glycosyl-7,4'-Di-O-Beta-D-Glucosyl Kaempferol
IUPAC Name	[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[5-hydroxy-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-3-yl]oxyoxan-3-yl] (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2206207
PubChem CID	21626414
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 115121 0 0 0 0 0 0 0 0999 V2000 9.4905 5.5644 0.7886 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4513 5.1254 -0.5433 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7174 4.0669 -1.0164 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9353 3.3308 -0.1803 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1741 2.2540 -0.5907 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2344 1.9393 -1.9277 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0254 2.6720 -2.8186 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7665 3.7336 -2.3688 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5794 4.5186 -3.1757 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3545 1.4863 0.3593 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6371 0.4428 0.0285 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8198 -0.3095 1.0111 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7567 0.0261 2.2154 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0976 -1.4267 0.6114 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2983 -2.2145 1.4775 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0402 -3.5325 1.7507 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8499 -4.5624 0.6788 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8957 -3.9744 -0.3389 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4741 -5.0231 -1.3534 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5773 -5.3702 -2.0974 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7409 -3.6673 0.3848 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9309 -2.3946 1.0225 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8960 -2.3217 2.0064 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4039 -2.3830 1.5208 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9455 -3.6681 1.4142 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2612 -4.6714 1.7585 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2211 -3.7702 0.9300 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8004 -5.0278 0.8034 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1037 -5.0860 0.3024 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7854 -3.9451 -0.0512 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1675 -2.7240 0.0935 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8600 -2.6094 0.5921 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3041 -1.4363 0.7159 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0545 -1.2613 1.1844 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5919 0.1051 1.2562 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5317 0.5654 1.8718 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9029 1.9221 1.8344 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1587 2.8719 1.1774 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9780 2.4164 0.5552 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3402 1.0931 0.5902 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5188 4.2085 1.1380 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1052 5.2584 0.5227 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6032 6.2329 1.6003 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5304 7.2580 1.0010 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9633 7.8113 -0.2686 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2347 6.7839 -1.0718 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3281 7.4088 -2.3060 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3725 8.2742 -1.9987 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6870 6.0288 -0.3399 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0833 8.1841 -1.0582 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6249 8.3208 1.9238 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2052 5.4622 2.5847 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0662 -4.0655 -0.5405 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9298 -3.0698 -0.9606 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3131 -3.3552 -2.3996 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0583 -4.6474 -2.4267 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.3743 -5.2513 -1.1023 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7196 -4.2447 -0.0338 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5201 -4.9151 1.3214 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9552 -4.1395 2.3780 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0498 -3.0572 -0.1274 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.5055 -6.0763 -1.2946 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3249 -5.6210 -3.1468 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9723 -2.2982 -3.0111 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0933 -6.1661 1.1668 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0587 -4.9352 0.0814 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8244 -4.0150 3.0243 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5735 4.7137 1.4898 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6245 6.2432 1.0305 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3963 6.2356 0.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9205 3.6329 0.8809 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6754 1.1107 -2.3551 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0732 2.4211 -3.8782 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0670 4.1384 -3.9886 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3202 1.7745 1.4079 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6331 0.1117 -0.9961 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3412 -1.6945 2.4600 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1376 -3.2409 1.7156 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4135 -5.5102 1.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3235 -3.0862 -0.8044 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9638 -5.8618 -0.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7476 -4.5663 -2.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3265 -6.2129 -2.5872 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6362 -1.7125 0.2099 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5904 -6.0347 0.1909 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6316 -1.7725 -0.1552 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1368 -0.1333 2.4180 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7943 2.2136 2.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6202 3.1368 0.0139 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2591 0.7943 0.0760 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0248 4.9677 -0.0416 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2953 6.7629 1.9728 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5639 6.8683 0.8799 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3509 8.7027 -0.0295 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0294 6.0444 -1.4060 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7995 6.5864 -2.9187 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4699 7.8635 -2.9172 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5819 8.7806 -2.8298 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5953 8.7867 -0.4682 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3055 8.0336 2.6118 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8432 6.0263 3.1102 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4401 -2.0738 -0.8613 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3409 -3.5014 -2.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0205 -4.5056 -2.9800 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5597 -5.9659 -0.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8055 -4.0387 -0.1035 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4622 -5.1821 1.4888 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1124 -5.8518 1.3071 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9305 -4.2728 2.5122 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4883 -6.7496 -0.5691 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4434 -5.2283 -3.3659 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8145 -2.6932 -3.3956 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1936 -6.4734 2.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7560 -4.2976 0.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2820 -3.4187 3.6687 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 30 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 38 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 45 50 1 0 44 51 1 0 43 52 1 0 30 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 58 61 1 0 57 62 1 0 56 63 1 0 55 64 1 0 28 65 1 0 17 66 1 0 16 67 1 0 8 3 1 0 22 15 1 0 34 24 2 0 40 35 1 0 49 42 1 0 61 54 1 0 32 27 1 0 1 68 1 0 1 69 1 0 1 70 1 0 4 71 1 0 6 72 1 0 7 73 1 0 9 74 1 0 10 75 1 0 11 76 1 0 15 77 1 1 16 78 1 1 17 79 1 1 18 80 1 6 19 81 1 0 19 82 1 0 20 83 1 0 22 84 1 6 29 85 1 0 31 86 1 0 36 87 1 0 37 88 1 0 39 89 1 0 40 90 1 0 42 91 1 6 43 92 1 1 44 93 1 6 45 94 1 1 46 95 1 6 47 96 1 0 47 97 1 0 48 98 1 0 50 99 1 0 51100 1 0 52101 1 0 54102 1 6 55103 1 6 56104 1 6 57105 1 1 58106 1 6 59107 1 0 59108 1 0 60109 1 0 62110 1 0 63111 1 0 64112 1 0 65113 1 0 66114 1 0 67115 1 0 M END

Standard InCHIKey	XDQCEAKLWIPMLQ-NGCLWCRHSA-N
Standard InCHI	InChI=1S/C43H48O24/c1-59-22-10-16(2-8-20(22)47)3-9-27(49)66-40-35(56)31(52)26(15-46)65-43(40)67-39-32(53)28-21(48)11-19(61-42-37(58)34(55)30(51)25(14-45)64-42)12-23(28)62-38(39)17-4-6-18(7-5-17)60-41-36(57)33(54)29(50)24(13-44)63-41/h2-12,24-26,29-31,33-37,40-48,50-52,54-58H,13-15H2,1H3/b9-3+/t24-,25-,26-,29-,30-,31-,33+,34+,35+,36-,37-,40-,41-,42-,43+/m1/s1
SMILES	COc1cc(ccc1O)/C=C/C(=O)O[C@@H]1[C@H]([C@@H]([C@@H](CO)O[C@H]1Oc1c(=O)c2c(cc(cc2oc1c1ccc(cc1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	948.25	Volume:	869.08 ? Van der Waals volume.
Dense:	1.091	LogP:	0.857 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.272 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.292 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	44.0
TPSA:	384.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.043	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.697	Fsp³:	0.442
MCE-18:	170.71 ? 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:	0.699	Fluc inhibitor:	0.537 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.769 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.663 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.301	Promiscuous compounds:	0.484

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.878	MDCK Permeability:	-4.953
Pgp-inhibitor:	0.0	Pgp-substrate:	0.157
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):	0.999
20% Bioavailability (F20%):	0.208	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.0
Plasma Protein Binding (PPB):	75.787%	Volume Distribution (VD):	-0.175
Fu:	21.852% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.092
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:	0.001
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.862
HLM stability:	0.0 ? 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):

0.689

Half-life (T1/2):

6.378

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.005
Human Hepatotoxicity (H-HT):	0.938	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.038	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.29	Drug-induced Nephrotoxicity:	0.992
Genotoxicity:	0.964	RPMI-8226 Immunitoxicity:	0.319
A549 Cytotoxicity:	0.858	Hek293 Cytotoxicity:	0.527
BCF:	0.479 ? 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:	3.257 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.13 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.115 ? 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
NPO3860.1	Allium victorialis	Under-species	n.a.	n.a.	Leaves	Taeback, GangWon province, Korea	2011-Jan	PMID[23149227]

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	1
IC50	1

Activity Type	# Activity
Cell line	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
NPT34	Cell line	BV-2	Mus musculus	Activity	=	100.7	%	PubChem BioAssay data set
NPT34	Cell line	BV-2	Mus musculus	IC50	=	43350.0	nM	PMID[16448174]

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 NPC295625 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	19471
0.1-0.2	26086
0.2-0.3	3097
0.3-0.4	793
0.4-0.5	301
0.5-0.6	71
0.6-0.7	13
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9381	High Similarity	NPC470717
0.9184	High Similarity	NPC470719
0.9091	High Similarity	NPC470720
0.8763	High Similarity	NPC470715
0.8515	High Similarity	NPC470713
0.8384	Intermediate Similarity	NPC164704
0.75	Intermediate Similarity	NPC470712
0.7196	Intermediate Similarity	NPC470716
0.71	Intermediate Similarity	NPC64425
0.6881	Remote Similarity	NPC470718
0.6702	Remote Similarity	NPC289667
0.6293	Remote Similarity	NPC488078
0.623	Remote Similarity	NPC223860
0.6218	Remote Similarity	NPC25946
0.6168	Remote Similarity	NPC35119
0.6154	Remote Similarity	NPC488079
0.6122	Remote Similarity	NPC297987
0.6061	Remote Similarity	NPC84362
0.6033	Remote Similarity	NPC21359
0.6033	Remote Similarity	NPC460984
0.6019	Remote Similarity	NPC32641
0.6019	Remote Similarity	NPC256188
0.5962	Remote Similarity	NPC251417
0.596	Remote Similarity	NPC136042
0.5902	Remote Similarity	NPC480470
0.5833	Remote Similarity	NPC240306
0.5825	Remote Similarity	NPC116458
0.5825	Remote Similarity	NPC246943
0.5739	Remote Similarity	NPC480796
0.5739	Remote Similarity	NPC472993
0.5738	Remote Similarity	NPC480472
0.5691	Remote Similarity	NPC199172
0.569	Remote Similarity	NPC25523
0.5673	Remote Similarity	NPC605784
0.5645	Remote Similarity	NPC35924
0.5641	Remote Similarity	NPC277532
0.5631	Remote Similarity	NPC611303
0.5625	Remote Similarity	NPC76831
0.5577	Remote Similarity	NPC22832
0.5556	Remote Similarity	NPC480441
0.5534	Remote Similarity	NPC472459
0.5517	Remote Similarity	NPC470416
0.5495	Remote Similarity	NPC477628
0.549	Remote Similarity	NPC64305
0.549	Remote Similarity	NPC95090
0.549	Remote Similarity	NPC27408
0.5478	Remote Similarity	NPC14187
0.5429	Remote Similarity	NPC21666
0.5429	Remote Similarity	NPC486578
0.5391	Remote Similarity	NPC483767
0.5391	Remote Similarity	NPC483769
0.5391	Remote Similarity	NPC483768
0.5391	Remote Similarity	NPC483766
0.5377	Remote Similarity	NPC311830
0.537	Remote Similarity	NPC473682
0.5333	Remote Similarity	NPC285197
0.5327	Remote Similarity	NPC488072
0.531	Remote Similarity	NPC139060
0.531	Remote Similarity	NPC606657
0.5288	Remote Similarity	NPC46420
0.5288	Remote Similarity	NPC24043
0.5283	Remote Similarity	NPC243930
0.5283	Remote Similarity	NPC120099
0.5283	Remote Similarity	NPC80188
0.5259	Remote Similarity	NPC218161
0.5243	Remote Similarity	NPC249281
0.521	Remote Similarity	NPC219043
0.521	Remote Similarity	NPC48984
0.5189	Remote Similarity	NPC488071
0.5185	Remote Similarity	NPC203050
0.5185	Remote Similarity	NPC225434
0.5185	Remote Similarity	NPC601586
0.5152	Remote Similarity	NPC249560
0.5143	Remote Similarity	NPC271692
0.514	Remote Similarity	NPC148710
0.514	Remote Similarity	NPC224530
0.514	Remote Similarity	NPC601144
0.514	Remote Similarity	NPC609478
0.5128	Remote Similarity	NPC484301
0.5085	Remote Similarity	NPC483765
0.5079	Remote Similarity	NPC138990
0.5048	Remote Similarity	NPC277205
0.5048	Remote Similarity	NPC37919
0.5048	Remote Similarity	NPC189142
0.5048	Remote Similarity	NPC77660
0.5047	Remote Similarity	NPC60735
0.5047	Remote Similarity	NPC26230
0.5046	Remote Similarity	NPC170052
0.5046	Remote Similarity	NPC276377
0.5046	Remote Similarity	NPC135846
0.5043	Remote Similarity	NPC210961
0.5041	Remote Similarity	NPC217520
0.504	Remote Similarity	NPC162394

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC295625 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4994
0.1-0.2	4104
0.2-0.3	43
0.3-0.4	5
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