NPASS Compound

Natural Product: NPC470715

Natural Product ID	NPC470715
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Allivictoside D
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] (Z)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms	Allivictoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2206200
PubChem CID	71461383
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 111117 0 0 0 0 0 0 0 0999 V2000 7.9248 -1.8491 -2.7618 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8748 -2.5833 -3.4711 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1556 -3.8943 -3.1161 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4721 -4.4349 -2.0534 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5409 -3.6947 -1.3681 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2314 -2.3674 -1.6990 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2272 -1.6419 -0.9419 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8669 -0.4209 -1.2056 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8351 0.2439 -0.3833 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4673 1.4159 -0.6141 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2515 -0.4223 0.6641 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2537 0.0812 1.5308 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7901 0.1546 2.9606 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9659 -1.2063 3.5305 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8421 -2.1515 3.2349 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3283 -2.0806 1.9695 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0424 -0.7509 1.5684 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4919 -0.9107 0.2486 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1284 -1.1247 0.0875 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7681 -0.1394 -0.1144 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0423 -0.4936 -0.2370 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4566 -1.7343 -0.1742 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8073 -2.0552 -0.3094 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2734 -3.3363 -0.2491 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3658 -4.3670 -0.0444 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0448 -4.0746 0.0893 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5799 -2.7659 0.0263 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2513 -2.4643 0.1619 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5663 -3.3837 0.3451 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1014 -5.0892 0.2962 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6075 -3.6498 -0.3829 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6787 -2.8019 -0.6056 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4205 -3.2244 -1.8595 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8733 -3.5071 -1.5623 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0708 -4.4334 -0.3833 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9278 -4.2155 0.5755 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5494 -2.8753 0.5125 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2840 -4.5505 1.9973 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6682 -5.9098 2.0640 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1612 -5.7598 -0.8061 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.6038 -2.3153 -1.3930 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3777 -2.2288 -2.8166 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4711 1.2959 -0.2101 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5315 2.2018 -0.1002 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3428 3.5522 -0.2148 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0890 4.0897 -0.4459 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9368 3.1937 -0.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7738 1.8138 -0.4405 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0474 5.4372 -0.5509 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1997 6.1990 -0.7809 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5202 7.1055 0.3845 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7951 8.4056 0.3796 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8303 9.0011 -0.9989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3380 7.9818 -1.9785 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1550 6.8872 -1.9875 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1283 7.6682 -1.8012 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6135 6.8645 -2.8001 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1151 10.1954 -1.0779 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5067 9.2820 1.2264 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1789 6.4205 1.5459 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1692 -3.5774 3.5508 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0571 -4.4097 3.4970 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1439 -1.1718 4.9219 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9189 0.9326 2.9790 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1119 -4.6129 -3.8419 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7288 -0.8178 -3.0687 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3809 -2.1029 -4.2972 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6892 -5.4728 -1.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9920 -4.1065 -0.5274 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7456 -2.1515 -0.1011 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3076 0.1164 -2.0150 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0225 1.1111 1.2229 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0116 0.6876 3.5521 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8974 -1.6442 3.1100 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0064 -1.8585 3.9385 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2561 -0.3454 2.2008 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4618 -1.2247 -0.4652 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7488 -5.3678 0.0002 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8584 -5.3482 1.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3445 -1.7616 -0.7421 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9771 -4.1460 -2.2806 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3022 -4.0151 -2.4661 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0253 -4.1995 0.1636 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0955 -4.8637 0.2224 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1554 -3.9658 2.3374 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4683 -4.3719 2.6999 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9960 -6.4678 1.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5154 -5.8575 -1.5613 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0253 -1.9961 -2.2234 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4714 -1.9458 -3.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5250 1.8281 0.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2102 4.2000 -0.1179 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9704 3.5095 -0.7340 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6187 1.1581 -0.5682 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0593 5.5044 -0.8708 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6325 7.2839 0.4032 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2275 8.3497 0.8047 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8846 9.2357 -1.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4300 8.4520 -2.9992 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6897 8.6374 -1.8711 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3803 7.2452 -0.8241 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4594 6.4420 -2.4517 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6080 10.9315 -0.6460 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4645 9.0446 1.2604 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1737 6.3474 1.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6464 -3.6997 4.5458 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8989 -4.0140 2.8110 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0156 -5.0314 4.2678 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0259 -0.2314 5.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7590 0.4445 2.9359 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7465 -5.2643 -3.3537 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 3 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 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 2 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 27 28 1 0 28 29 2 0 26 30 1 0 24 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 35 40 1 0 34 41 1 0 33 42 1 0 20 43 1 0 43 44 2 0 44 45 1 0 45 46 2 0 46 47 1 0 47 48 2 0 46 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 53 58 1 0 52 59 1 0 51 60 1 0 15 61 1 0 61 62 1 0 14 63 1 0 13 64 1 0 3 65 1 0 6 1 1 0 17 12 1 0 28 19 1 0 27 22 1 0 37 32 1 0 48 43 1 0 55 50 1 0 1 66 1 0 2 67 1 0 4 68 1 0 5 69 1 0 7 70 1 0 8 71 1 0 12 72 1 0 13 73 1 0 14 74 1 0 15 75 1 0 17 76 1 0 23 77 1 0 25 78 1 0 30 79 1 0 32 80 1 0 33 81 1 0 34 82 1 0 35 83 1 0 36 84 1 0 38 85 1 0 38 86 1 0 39 87 1 0 40 88 1 0 41 89 1 0 42 90 1 0 44 91 1 0 45 92 1 0 47 93 1 0 48 94 1 0 50 95 1 0 51 96 1 0 52 97 1 0 53 98 1 0 54 99 1 0 56100 1 0 56101 1 0 57102 1 0 58103 1 0 59104 1 0 60105 1 0 61106 1 0 61107 1 0 62108 1 0 63109 1 0 64110 1 0 65111 1 0 M END

Standard InCHIKey	CXRZYTKTWBIBOA-JYRPTVFISA-N
Standard InCHI	InChI=1S/C42H46O23/c43-13-23-28(49)32(53)35(56)40(61-23)58-19-8-4-17(5-9-19)37-38(31(52)27-21(47)11-20(12-22(27)60-37)59-41-36(57)33(54)29(50)24(14-44)62-41)65-42-39(34(55)30(51)25(15-45)63-42)64-26(48)10-3-16-1-6-18(46)7-2-16/h1-12,23-25,28-30,32-36,39-47,49-51,53-57H,13-15H2/b10-3-/t23-,24-,25-,28-,29-,30-,32+,33+,34+,35-,36-,39-,40-,41-,42+/m1/s1
SMILES	C1=CC(=CC=C1C=CC(=O)OC2C(C(C(OC2OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)CO)O)O)O)C6=CC=C(C=C6)OC7C(C(C(C(O7)CO)O)O)O)CO)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	918.24	Volume:	842.994 ? Van der Waals volume.
Dense:	1.089	LogP:	-0.588 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.405 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.392 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	44.0
TPSA:	374.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	13.0	Rings:	7.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.046	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.63	Fsp³:	0.429
MCE-18:	168.0 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.35	Fluc inhibitor:	0.354 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.718 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.667 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.599	Promiscuous compounds:	0.485

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.823	MDCK Permeability:	-4.827
Pgp-inhibitor:	0.0	Pgp-substrate:	0.926
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%):	0.985	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.824
Plasma Protein Binding (PPB):	75.648%	Volume Distribution (VD):	-0.15
Fu:	24.767% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.965	BCRP inhibitor:	0.137
BSEP inhibitor:	0.004

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.162	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:	0.692
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):

0.802

Half-life (T1/2):

4.512

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.223
Human Hepatotoxicity (H-HT):	0.61	Drug-induced Liver Injury (DILI):	0.923
AMES Toxicity:	0.842	Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.197	Skin Sensitization:	0.319
Carcinogencity:	0.05	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.034	Ototoxicity:	0.999
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.079
Genotoxicity:	0.326	RPMI-8226 Immunitoxicity:	0.095
A549 Cytotoxicity:	0.106	Hek293 Cytotoxicity:	0.968
BCF:	0.47 ? 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:	3.134 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.322 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.004 ? 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	=	100.4	%	PMID[25828928]
NPT34	Cell line	BV-2	Mus musculus	IC50	=	48480.0	nM	PMID[20627740]

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 NPC470715 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	17953
0.1-0.2	27560
0.2-0.3	3164
0.3-0.4	693
0.4-0.5	326
0.5-0.6	132
0.6-0.7	14
0.7-0.8	0
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.956	High Similarity	NPC164704
0.8763	High Similarity	NPC295625
0.8586	High Similarity	NPC470717
0.8542	High Similarity	NPC470712
0.8317	Intermediate Similarity	NPC470720
0.8182	Intermediate Similarity	NPC470716
0.8039	Intermediate Similarity	NPC470719
0.7766	Intermediate Similarity	NPC64425
0.7647	Intermediate Similarity	NPC470718
0.7596	Intermediate Similarity	NPC470713
0.7	Intermediate Similarity	NPC289667
0.6739	Remote Similarity	NPC297987
0.6733	Remote Similarity	NPC35119
0.6569	Remote Similarity	NPC32641
0.6569	Remote Similarity	NPC256188
0.6441	Remote Similarity	NPC223860
0.6392	Remote Similarity	NPC116458
0.6392	Remote Similarity	NPC246943
0.6311	Remote Similarity	NPC477628
0.6211	Remote Similarity	NPC136042
0.6182	Remote Similarity	NPC25523
0.6095	Remote Similarity	NPC139060
0.6058	Remote Similarity	NPC240306
0.604	Remote Similarity	NPC251417
0.6019	Remote Similarity	NPC218161
0.5981	Remote Similarity	NPC76831
0.5979	Remote Similarity	NPC84362
0.59	Remote Similarity	NPC605784
0.5876	Remote Similarity	NPC64305
0.5872	Remote Similarity	NPC483767
0.5872	Remote Similarity	NPC483769
0.5872	Remote Similarity	NPC483768
0.5872	Remote Similarity	NPC483766
0.5806	Remote Similarity	NPC249560
0.5794	Remote Similarity	NPC210961
0.5773	Remote Similarity	NPC249281
0.5755	Remote Similarity	NPC472992
0.5752	Remote Similarity	NPC480441
0.5741	Remote Similarity	NPC205824
0.5741	Remote Similarity	NPC221288
0.5741	Remote Similarity	NPC270675
0.5741	Remote Similarity	NPC194836
0.5741	Remote Similarity	NPC472991
0.5741	Remote Similarity	NPC195685
0.5741	Remote Similarity	NPC91493
0.5741	Remote Similarity	NPC605081
0.5726	Remote Similarity	NPC162394
0.5688	Remote Similarity	NPC80068
0.5688	Remote Similarity	NPC85751
0.5688	Remote Similarity	NPC19240
0.5676	Remote Similarity	NPC14187
0.5648	Remote Similarity	NPC104883
0.5648	Remote Similarity	NPC488679
0.5644	Remote Similarity	NPC224530
0.562	Remote Similarity	NPC25946
0.5612	Remote Similarity	NPC39360
0.5612	Remote Similarity	NPC29763
0.5612	Remote Similarity	NPC210003
0.56	Remote Similarity	NPC472459
0.5577	Remote Similarity	NPC473682
0.5565	Remote Similarity	NPC277532
0.5556	Remote Similarity	NPC95090
0.5556	Remote Similarity	NPC27408
0.5534	Remote Similarity	NPC170052
0.5534	Remote Similarity	NPC276377
0.5534	Remote Similarity	NPC135846
0.55	Remote Similarity	NPC46420
0.55	Remote Similarity	NPC24043
0.549	Remote Similarity	NPC22832
0.5455	Remote Similarity	NPC77672
0.5455	Remote Similarity	NPC133671
0.5455	Remote Similarity	NPC135391
0.5455	Remote Similarity	NPC78263
0.5455	Remote Similarity	NPC250069
0.5446	Remote Similarity	NPC223426
0.5446	Remote Similarity	NPC484301
0.5446	Remote Similarity	NPC472994
0.5421	Remote Similarity	NPC150164
0.5417	Remote Similarity	NPC488078
0.54	Remote Similarity	NPC323593
0.54	Remote Similarity	NPC203500
0.54	Remote Similarity	NPC189142
0.54	Remote Similarity	NPC77660
0.5398	Remote Similarity	NPC483765
0.5392	Remote Similarity	NPC285197
0.5392	Remote Similarity	NPC611303
0.5391	Remote Similarity	NPC477895
0.5357	Remote Similarity	NPC36138
0.534	Remote Similarity	NPC243930
0.534	Remote Similarity	NPC80188
0.5323	Remote Similarity	NPC21359
0.5323	Remote Similarity	NPC460984
0.5315	Remote Similarity	NPC101399
0.5315	Remote Similarity	NPC217822
0.5315	Remote Similarity	NPC11847
0.5315	Remote Similarity	NPC198938
0.53	Remote Similarity	NPC261866
0.5289	Remote Similarity	NPC488079
0.5283	Remote Similarity	NPC8856
0.5263	Remote Similarity	NPC214621
0.5263	Remote Similarity	NPC34267
0.5259	Remote Similarity	NPC219043
0.5259	Remote Similarity	NPC48984
0.5259	Remote Similarity	NPC472993
0.5248	Remote Similarity	NPC277205
0.5248	Remote Similarity	NPC37919
0.5243	Remote Similarity	NPC60735
0.5243	Remote Similarity	NPC26230
0.5242	Remote Similarity	NPC199172
0.5229	Remote Similarity	NPC186816
0.5225	Remote Similarity	NPC72016
0.5221	Remote Similarity	NPC260504
0.5221	Remote Similarity	NPC89809
0.5214	Remote Similarity	NPC217520
0.5196	Remote Similarity	NPC488080
0.5196	Remote Similarity	NPC169977
0.5192	Remote Similarity	NPC120099
0.5192	Remote Similarity	NPC21666
0.5192	Remote Similarity	NPC486578
0.5192	Remote Similarity	NPC601144
0.5189	Remote Similarity	NPC254855
0.5189	Remote Similarity	NPC94610
0.5185	Remote Similarity	NPC163242
0.5185	Remote Similarity	NPC272068
0.5179	Remote Similarity	NPC142142
0.5143	Remote Similarity	NPC311830
0.5138	Remote Similarity	NPC65003
0.5138	Remote Similarity	NPC304741
0.5133	Remote Similarity	NPC188815
0.5133	Remote Similarity	NPC477629
0.5133	Remote Similarity	NPC603951
0.5133	Remote Similarity	NPC606158
0.5128	Remote Similarity	NPC480796
0.5126	Remote Similarity	NPC255799
0.5122	Remote Similarity	NPC138990
0.5118	Remote Similarity	NPC231787
0.5098	Remote Similarity	NPC145038
0.5098	Remote Similarity	NPC8573
0.5098	Remote Similarity	NPC56077
0.5098	Remote Similarity	NPC197896
0.5098	Remote Similarity	NPC281131
0.5098	Remote Similarity	NPC313163
0.5098	Remote Similarity	NPC253662
0.5098	Remote Similarity	NPC179950
0.5098	Remote Similarity	NPC88789
0.5098	Remote Similarity	NPC491374
0.5096	Remote Similarity	NPC488071
0.5089	Remote Similarity	NPC606657
0.5086	Remote Similarity	NPC121703
0.5082	Remote Similarity	NPC156785
0.5079	Remote Similarity	NPC480470
0.5049	Remote Similarity	NPC271692
0.5048	Remote Similarity	NPC148710
0.5048	Remote Similarity	NPC609478
0.5045	Remote Similarity	NPC61904
0.5045	Remote Similarity	NPC470125
0.5044	Remote Similarity	NPC5319

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470715 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5051
0.1-0.2	4045
0.2-0.3	45
0.3-0.4	4
0.4-0.5	4
0.5-0.6	1
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
0.5044	Remote Similarity	NPD7804	Clinical (unspecified phase)

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