NPASS Compound

Natural Product: NPC491289

Natural Product ID	NPC491289
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cyanidin 3-o-xyloside
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	52922414
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000256] Glycerophospholipids [CHEMONTID:0002213] Glycerophosphocholines [CHEMONTID:0001408] Phosphatidylcholines

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 139138 0 0 0 0 0 0 0 0999 V2000 23.3827 13.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 22.0836 12.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.7846 12.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.4856 11.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.1865 10.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.8875 9.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.5885 9.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2894 8.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9904 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6913 6.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3923 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0933 5.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7942 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4952 3.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8971 2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2990 0.7500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7671 0.4429 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2990 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0490 -0.9510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7990 0.3481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2990 0.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0490 -0.9510 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0490 1.6471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7990 2.9462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5490 4.2452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2990 5.5442 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0490 6.8433 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7990 8.1423 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5490 9.4413 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2990 10.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0490 12.0394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7990 13.3385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5490 14.6375 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2990 15.9365 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0490 17.2356 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7990 18.5346 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.5490 19.8336 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5490 -3.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2010 -4.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7010 -4.8481 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 1.7010 -3.3481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7010 -6.3481 0.0000 O 0 0 0 0 0 1 0 0 0 0 0 0 3.2010 -4.8481 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9510 -3.5490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7010 -2.2500 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4510 -0.9510 0.0000 N 0 0 0 0 0 4 0 0 0 0 0 0 6.2010 0.3481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7500 -1.7010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1519 -0.2010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 24.6817 14.2500 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.6327 14.7990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 24.1327 12.2010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.3336 14.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.8336 11.4510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.5346 10.7010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.0346 13.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.7356 12.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.2356 9.9510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.9365 9.2010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.4365 11.7990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.1375 11.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.6375 8.4510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.3385 7.7010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8385 10.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5394 9.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0394 6.9510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7404 6.2010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2404 8.7990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9413 8.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4413 5.4510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1423 4.7010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6423 7.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3433 6.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8433 3.9510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5442 3.2010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0442 5.7990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7452 5.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3979 2.5521 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9462 1.7010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4462 4.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1471 3.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3892 1.3977 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1841 0.1192 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8481 2.7990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0490 -0.5490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5490 2.0490 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3481 -1.7010 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4119 -0.3356 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3481 0.8971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 2.3971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 3.6962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0981 2.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8481 3.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 4.9952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 6.2942 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5981 4.7942 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3481 6.0933 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7500 7.5933 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 8.8923 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0981 7.3923 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8481 8.6913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2500 10.1913 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0000 11.4904 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5981 9.9904 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3481 11.2894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7500 12.7894 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5000 14.0885 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0981 12.5885 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8481 13.8875 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2500 15.3875 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0000 16.6865 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5981 15.1865 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.3481 16.4856 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7500 17.9856 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5000 19.2846 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.0981 17.7846 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.2990 21.1327 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.8481 19.0836 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2500 20.5836 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8481 -4.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -2.7990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6519 -2.7990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2500 -4.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7791 -3.0625 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3202 -1.6639 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1037 1.5460 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0163 0.0020 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3487 0.8402 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0490 -2.4510 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2831 -0.9936 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2225 -2.9437 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7712 0.3851 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2492 -1.3989 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9019 1.0981 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 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 19 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 1 0 28 29 1 0 29 30 1 0 30 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 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 22 42 1 0 42 43 1 0 43 44 1 0 44 45 2 0 44 46 1 0 44 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 50 52 1 0 50 53 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 0 2 58 1 0 3 59 1 0 3 60 1 0 4 61 1 0 4 62 1 0 5 63 1 0 5 64 1 0 6 65 1 0 6 66 1 0 7 67 1 0 7 68 1 0 8 69 1 0 8 70 1 0 9 71 1 0 9 72 1 0 10 73 1 0 10 74 1 0 11 75 1 0 11 76 1 0 12 77 1 0 12 78 1 0 13 79 1 0 13 80 1 0 14 81 1 0 14 82 1 0 15 83 1 0 15 84 1 0 16 85 1 0 16 86 1 0 17 87 1 0 17 88 1 0 18 89 1 0 18 90 1 0 22 91 1 6 23 92 1 0 23 93 1 0 27 94 1 0 27 95 1 0 28 96 1 0 28 97 1 0 29 98 1 0 29 99 1 0 30100 1 0 30101 1 0 31102 1 0 31103 1 0 32104 1 0 32105 1 0 33106 1 0 33107 1 0 34108 1 0 34109 1 0 35110 1 0 35111 1 0 36112 1 0 36113 1 0 37114 1 0 37115 1 0 38116 1 0 38117 1 0 39118 1 0 39119 1 0 40120 1 0 40121 1 0 41122 1 0 41123 1 0 41124 1 0 42125 1 0 42126 1 0 48127 1 0 48128 1 0 49129 1 0 49130 1 0 51131 1 0 51132 1 0 51133 1 0 52134 1 0 52135 1 0 52136 1 0 53137 1 0 53138 1 0 53139 1 0 M CHG 2 46 -1 50 1 M END

Standard InCHIKey	DRHYTKZTKWDSBJ-VQJSHJPSSA-N
Standard InCHI	InChI=1S/C43H86NO8P/c1-6-8-10-12-14-16-18-20-21-22-24-26-28-30-32-34-36-43(46)52-41(40-51-53(47,48)50-38-37-44(3,4)5)39-49-42(45)35-33-31-29-27-25-23-19-17-15-13-11-9-7-2/h41H,6-40H2,1-5H3/t41-/m1/s1
SMILES	CCCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCCCCCCC)COP(=O)([O-])OCC[N+](C)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	775.61	Volume:	848.157 ? Van der Waals volume.
Dense:	0.914	LogP:	2.003 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.783 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	2.92 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	43.0	Rigid Bonds:	3.0
TPSA:	111.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	0.0	Rings:	0.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.026	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.938	Fsp³:	0.953
MCE-18:	9.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.622	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.222	Promiscuous compounds:	0.433

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.611	MDCK Permeability:	-4.8
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.0 ? 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):	0.995
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:	0.999
Plasma Protein Binding (PPB):	101.819%	Volume Distribution (VD):	1.989
Fu:	0.312% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.41
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	1.0
CYP2C19-inhibitor:	0.023	CYP2C19-substrate:	1.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.031	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
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):

3.786

Half-life (T1/2):

4.718

ADMET: Toxicity

hERG Blockers:	0.658	hERG Blockers (10um):	0.815
Human Hepatotoxicity (H-HT):	0.948	Drug-induced Liver Injury (DILI):	0.134
AMES Toxicity:	0.059	Rat Oral Acute Toxicity:	0.347
Maximum Recommended Daily Dose:	0.991	Skin Sensitization:	1.0
Carcinogencity:	0.749	Eye Corrosion:	0.998
Eye Irritation:	0.998	Respiratory Toxicity:	0.998
Drug-induced Neurotoxicity:	0.055	Ototoxicity:	0.002
Hematotoxicity:	0.026	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.042
A549 Cytotoxicity:	0.012	Hek293 Cytotoxicity:	0.032
BCF:	-1.175 ? 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:	4.202 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	7.249 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	0.75 ? 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
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/(SICI)1097-0010(199909)79:12<1620::AID-JSFA410>3.0.CO;2-G]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1007/s00217-002-0656-1]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1007/s00217-015-2561-4]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.foodchem.2007.07.014]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.foodchem.2010.05.061]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.foodchem.2010.05.061]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.indcrop.2013.08.051]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.		DOI[10.1016/j.ssnmr.2006.05.001]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1016/j.yclnex.2017.01.002; 10.31989/ffhd.v6i3.245]DOI[10.1016/j.yclnex.2017.01.002; 10.31989/ffhd.v6i3.245]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1080/09064710.2011.598543]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1111/j.1365-2621.1989.tb04709.x]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.1111/j.1745-4530.2009.00507.x]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.15835/NBHA4017181]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.17221/540/2012-CJFS]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.2137/145960607781635822]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.2478/aoas-2014-0072]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.3136/NSKKK.48.606]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		DOI[10.3390/agriculture2030244]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[13160012]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[15563205]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21648406]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[25026919]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[25977015]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[26351516]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[27556441]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Oct	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Sep	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Schirgiswalde, Germany	2008-Aug	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	Cracow, Poland	2008-Sep	PMID[31206724]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[31619015]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38893452]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		PMID[9301422]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Flowers	n.a.		PMID[9301422]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO590	Malus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7269	Aronia melanocarpa	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO590	Malus domestica	Species	Rosaceae	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
NPO590	Malus domestica	n.a.	Fruits	0.05512	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO7269	Aronia melanocarpa	delivered frozen and stored at -20 Â°C; extracted by amberlite R XAD-7HP	Fruits	95.4 Â± 0.080	n.a.	n.a.	mg/100g of DW	PMID[31206724]
NPO7269	Aronia melanocarpa	delivered frozen and stored at -20 Â°C; extracted by amberlite R XAD-7HP	Fruits	89.7 Â± 0.37	n.a.	n.a.	mg/100g of DW	PMID[31206724]
NPO7269	Aronia melanocarpa	delivered frozen and stored at -20 Â°C; extracted by amberlite R XAD-7HP	Fruits	89.9 Â± 1.86	n.a.	n.a.	mg/100g of DW	PMID[31206724]
NPO7269	Aronia melanocarpa	stored in a fridge; extracted by amberlite R XAD-7HP	Fruits	33.2 Â± 1.48	n.a.	n.a.	mg/100g of DW	PMID[31206724]
NPO7269	Aronia melanocarpa	n.a.	Fruits	45.905	n.a.	n.a.	mg/100g of FW	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

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

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 NPC491289 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	28236
0.1-0.2	20805
0.2-0.3	679
0.3-0.4	92
0.4-0.5	30
0.5-0.6	9
0.6-0.7	6
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC224700
1.0	High Similarity	NPC320663
0.6429	Remote Similarity	NPC55678
0.6275	Remote Similarity	NPC170963
0.6275	Remote Similarity	NPC324165
0.6275	Remote Similarity	NPC114640
0.6275	Remote Similarity	NPC126366
0.6275	Remote Similarity	NPC608333
0.5902	Remote Similarity	NPC325936
0.5789	Remote Similarity	NPC474702
0.5614	Remote Similarity	NPC178758
0.5614	Remote Similarity	NPC192326
0.5614	Remote Similarity	NPC322769
0.5397	Remote Similarity	NPC54460
0.5306	Remote Similarity	NPC602940
0.5294	Remote Similarity	NPC54925
0.5208	Remote Similarity	NPC478931

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC491289 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7153
0.1-0.2	1851
0.2-0.3	115
0.3-0.4	15
0.4-0.5	10
0.5-0.6	3
0.6-0.7	2
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	Drug ID	Developmental Stage
1.0	High Similarity	NPD8278	Phase 4
0.6731	Remote Similarity	NPD8277	Approved
0.6429	Remote Similarity	NPD6125	Phase 4
0.5833	Remote Similarity	NPD8302	Clinical (unspecified phase)
0.5472	Remote Similarity	NPD6950	Phase 2
0.5208	Remote Similarity	NPD4840	Phase 4

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