NPASS Compound

Natural Product: NPC85192

Natural Product ID	NPC85192
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Vanicoside A
IUPAC Name	[(2R,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-3-acetyloxy-4,5-dihydroxy-6-[[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxymethyl]oxan-2-yl]oxy-3-hydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy-5-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxymethyl]oxolan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL454490
PubChem CID	44575681
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0002995] Pentacarboxylic acids and derivatives

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 122127 0 0 0 0 0 0 0 0999 V2000 -1.8086 -0.1782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1386 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -0.6293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -0.1163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 -1.5935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 -2.1065 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -1.1424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -0.6293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7977 -0.1163 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9468 -1.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6863 -2.5577 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3563 -0.5674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5054 -1.5316 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9149 -1.0186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1754 0.4586 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5849 0.9716 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.7340 0.0075 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.4735 -1.4697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0640 -1.9828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.6226 -2.4339 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.3621 -3.9111 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.1435 0.5205 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 0.3349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4200 3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9237 3.3939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5727 3.4985 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2302 4.8467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3914 6.0903 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7266 4.9514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5654 3.7078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0617 3.8125 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9005 2.5689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3969 2.6735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0544 4.0217 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2156 5.2653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7193 5.1606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5508 4.1264 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3677 4.7884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7772 5.3014 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7007 4.1194 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8498 3.1552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9988 2.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4084 2.7040 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5574 1.7399 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6688 4.1813 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5198 5.1454 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7802 6.6227 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1898 7.1357 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4503 8.6129 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3012 9.5771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8916 9.0640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6312 7.5868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5617 11.0543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8619 2.8758 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0493 6.0963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0048 6.2438 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0838 7.2858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3265 6.7583 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7209 8.7412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7999 9.7832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4370 11.2387 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5160 12.2807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1532 13.7361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7113 14.1496 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6323 13.1076 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9951 11.6521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3484 15.6050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -3.0707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -3.0707 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3216 1.2314 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2956 -1.5877 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2181 -0.6912 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4095 1.1827 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9200 -1.5935 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0796 -3.4056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8814 -2.3403 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8751 0.7802 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0692 -1.9658 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6168 0.9098 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2449 -3.0088 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0263 1.4228 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8454 2.4489 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8035 -3.4600 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.8393 -4.1716 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8849 -3.6507 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.1016 -5.3884 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.2926 -0.4437 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4744 1.7918 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8190 1.8976 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8819 4.1900 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3841 6.2996 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9078 2.3596 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2430 1.2207 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2356 1.4300 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8732 6.6135 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8805 6.4042 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3895 2.8828 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5706 4.7745 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4654 6.7686 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9998 4.8693 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0328 1.8972 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6667 4.4132 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0784 4.6943 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0582 4.8081 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3388 6.1715 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8598 9.1259 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6336 9.8810 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2947 6.9058 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4126 12.0185 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5047 5.7335 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2790 9.1547 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1807 9.1971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9579 11.8672 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2322 14.7781 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1904 13.5210 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9161 10.6101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9065 16.0185 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4704 -2.9140 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.5837 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 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 2 0 11 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 19 21 1 0 21 22 1 0 18 23 1 0 8 24 1 0 24 25 1 0 25 26 1 0 27 26 1 1 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 2 0 33 34 1 0 34 35 2 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 2 0 37 40 1 0 27 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 2 0 46 48 1 0 48 49 2 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 53 56 1 0 43 57 1 0 42 58 1 0 41 59 1 0 59 60 1 0 60 61 2 0 60 62 1 0 62 63 2 0 63 64 1 0 64 65 2 0 65 66 1 0 66 67 2 0 67 68 1 0 68 69 2 0 67 70 1 0 7 71 1 0 6 72 1 0 25 5 1 0 57 27 1 0 69 64 1 0 20 15 1 0 39 34 1 0 55 50 1 0 1 73 1 0 1 74 1 0 1 75 1 0 5 76 1 6 6 77 1 1 7 78 1 6 8 79 1 1 9 80 1 0 9 81 1 0 13 82 1 0 14 83 1 0 16 84 1 0 17 85 1 0 20 86 1 0 22 87 1 0 22 88 1 0 22 89 1 0 23 90 1 0 25 91 1 1 28 92 1 0 28 93 1 0 32 94 1 0 33 95 1 0 35 96 1 0 36 97 1 0 38 98 1 0 39 99 1 0 40100 1 0 41101 1 6 42102 1 1 43103 1 6 44104 1 0 44105 1 0 48106 1 0 49107 1 0 51108 1 0 52109 1 0 54110 1 0 55111 1 0 56112 1 0 58113 1 0 62114 1 0 63115 1 0 65116 1 0 66117 1 0 68118 1 0 69119 1 0 70120 1 0 71121 1 0 72122 1 0 M END

Standard InCHIKey	RNXDQKHOEWIRNH-FSZFHJIYSA-N
Standard InCHI	InChI=1S/C51H50O21/c1-29(52)68-48-47(63)45(61)39(26-65-42(58)23-13-33-9-20-37(56)38(25-33)64-2)69-50(48)72-51(28-67-43(59)22-11-31-5-16-35(54)17-6-31)49(70-44(60)24-12-32-7-18-36(55)19-8-32)46(62)40(71-51)27-66-41(57)21-10-30-3-14-34(53)15-4-30/h3-25,39-40,45-50,53-56,61-63H,26-28H2,1-2H3/b21-10+,22-11+,23-13+,24-12+/t39-,40-,45-,46-,47+,48-,49+,50+,51+/m1/s1
SMILES	CC(=O)O[C@@H]1[C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(c(c2)OC)O)O[C@H]1O[C@@]1(COC(=O)/C=C/c2ccc(cc2)O)[C@H]([C@@H]([C@@H](COC(=O)/C=C/c2ccc(cc2)O)O1)O)OC(=O)/C=C/c1ccc(cc1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	998.28	Volume:	968.542 ? Van der Waals volume.
Dense:	1.031	LogP:	2.937 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.8 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.473 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	24.0	Rigid Bonds:	44.0
TPSA:	310.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	7.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.04	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.564	Fsp³:	0.275
MCE-18:	140.908 ? 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:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	1.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.161 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.664 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.327	Promiscuous compounds:	0.141

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.256	MDCK Permeability:	-5.407
Pgp-inhibitor:	0.927	Pgp-substrate:	0.0
PAMPA:	0.929 ? 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):	0.073
20% Bioavailability (F20%):	1.0	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):	95.078%	Volume Distribution (VD):	-0.252
Fu:	5.293% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.743
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.998
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.998
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.998
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.997 ? 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):

2.574

Half-life (T1/2):

3.62

ADMET: Toxicity

hERG Blockers:	0.149	hERG Blockers (10um):	0.551
Human Hepatotoxicity (H-HT):	0.594	Drug-induced Liver Injury (DILI):	0.924
AMES Toxicity:	0.926	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.895	Skin Sensitization:	1.0
Carcinogencity:	0.118	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.24	Ototoxicity:	0.709
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.926
Genotoxicity:	0.965	RPMI-8226 Immunitoxicity:	0.26
A549 Cytotoxicity:	0.708	Hek293 Cytotoxicity:	0.993
BCF:	0.316 ? 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:	3.86 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.973 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.733 ? 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
NPO40997	Polygonum pensylvanicum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8176400]
NPO40997	Polygonum pensylvanicum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6826	Persicaria perfoliata	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6826	Persicaria perfoliata	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO6826	Persicaria perfoliata	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
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
NPT2	Others	Unspecified	n.a.	IC50	=	44.0	ug.mL-1	PMID[8176400]

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 NPC85192 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	10560
0.1-0.2	34471
0.2-0.3	4068
0.3-0.4	598
0.4-0.5	124
0.5-0.6	15
0.6-0.7	9
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9873	High Similarity	NPC215095
0.7955	Intermediate Similarity	NPC201148
0.7816	Intermediate Similarity	NPC125823
0.7816	Intermediate Similarity	NPC7145
0.7816	Intermediate Similarity	NPC143480
0.7528	Intermediate Similarity	NPC3460
0.7262	Intermediate Similarity	NPC45224
0.7079	Intermediate Similarity	NPC216819
0.7065	Intermediate Similarity	NPC210611
0.663	Remote Similarity	NPC192763
0.663	Remote Similarity	NPC300262
0.6562	Remote Similarity	NPC261122
0.6477	Remote Similarity	NPC471883
0.6292	Remote Similarity	NPC28637
0.6146	Remote Similarity	NPC287615
0.6146	Remote Similarity	NPC199311
0.6	Remote Similarity	NPC28651
0.6	Remote Similarity	NPC80732
0.5957	Remote Similarity	NPC262182
0.5934	Remote Similarity	NPC484687
0.5729	Remote Similarity	NPC83743
0.5426	Remote Similarity	NPC35288
0.5312	Remote Similarity	NPC226005
0.5312	Remote Similarity	NPC471882
0.5213	Remote Similarity	NPC225307
0.5208	Remote Similarity	NPC472612
0.5158	Remote Similarity	NPC156692
0.5155	Remote Similarity	NPC476869
0.5135	Remote Similarity	NPC21956
0.5126	Remote Similarity	NPC246024
0.5102	Remote Similarity	NPC478887
0.5096	Remote Similarity	NPC472611
0.505	Remote Similarity	NPC172033

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC85192 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3894
0.1-0.2	5170
0.2-0.3	82
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

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

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data