NPASS Compound

Natural Product: NPC473581

Natural Product ID	NPC473581
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	1-O-Beta-D-Glucopyranosyl-(2S,3R,4E,8E)-2-[(2-Hydroxyoctadecanoyl)Amido]-4,8-Octadecadiene-1,3-Diol
IUPAC Name	2-hydroxy-N-[(2S,3R,4E,8E)-3-hydroxy-1-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadeca-4,8-dien-2-yl]octadecanamide
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL446472
PubChem CID	10169278
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000257] Sphingolipids [CHEMONTID:0003258] Glycosphingolipids [CHEMONTID:0001419] Neutral glycosphingolipids [CHEMONTID:0001428] Simple glycosylceramides [CHEMONTID:0004305] Glycosyl-N-acylsphingosines

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 131131 0 0 0 0 0 0 0 0999 V2000 -5.2436 -25.6941 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7306 -24.2845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2176 -22.8750 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7045 -21.4654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1915 -20.0559 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6785 -18.6464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1654 -17.2368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6524 -15.8273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1394 -14.4177 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6263 -13.0082 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1133 -11.5987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3997 -10.1891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9128 -8.7796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4258 -7.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9388 -5.9605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4518 -4.5510 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9649 -3.1414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4779 -1.7319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9086 -1.0534 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9551 -1.4714 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.4681 -0.0619 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3886 2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 3.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 4.8828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0905 4.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 2.8925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9791 1.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5796 3.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9891 3.9186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1700 5.8470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 5.8470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0586 3.4056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8777 -0.5749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2872 -1.0879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4363 -0.1238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8458 -0.6368 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2554 -1.1498 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6649 -1.6628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.8140 -0.6987 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.2235 -1.2117 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 17.6331 -1.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.0426 -2.2378 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.4521 -2.7508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 21.8617 -3.2638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 23.2712 -3.7768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 24.6807 -4.2899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 26.0903 -4.8029 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 27.4998 -5.3159 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3907 0.8346 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5553 -2.6284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7566 -27.1036 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8341 -26.2071 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6531 -25.1810 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3210 -24.7975 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1401 -23.7715 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6271 -22.3619 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8080 -23.3880 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2950 -21.9785 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1141 -20.9524 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6010 -19.5429 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7820 -20.5689 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2689 -19.1594 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0880 -18.1333 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5750 -16.7238 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7559 -17.7498 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2429 -16.3403 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0619 -15.3142 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5489 -13.9047 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2702 -14.9308 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7832 -13.5212 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0359 -12.4952 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5228 -11.0856 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2962 -12.1117 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8093 -10.7022 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0098 -9.6761 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4968 -8.2666 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3223 -9.2926 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8353 -7.8831 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0162 -6.8570 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5293 -5.4475 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3484 -6.4735 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9903 -4.2136 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8614 -5.0640 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3744 -3.6545 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7720 -2.7294 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9812 1.3477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7396 1.7876 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5633 -0.2831 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5945 2.5895 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3991 5.2176 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 6.1818 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7008 4.4669 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 -2.0926 1.9960 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4002 4.1823 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1382 2.9544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5796 6.3600 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3886 7.3242 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2077 4.3698 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5403 -2.0365 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5477 -2.5652 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3578 1.3742 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3589 0.7728 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3328 -2.0463 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7684 0.2597 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7423 -2.5594 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9254 -3.1401 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5535 0.7785 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.7365 0.1978 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7105 -2.6212 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.1200 -3.1343 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.1461 -0.3152 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 19.5556 -0.8282 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.5296 -3.6473 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 19.9391 -4.1603 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.9652 -1.3412 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.3747 -1.8543 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.3486 -4.6734 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.7582 -5.1864 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 23.7842 -2.3673 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 25.1938 -2.8803 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 24.1677 -5.6994 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 25.5773 -6.2124 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 26.6033 -3.3934 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 28.9094 -5.8290 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 28.0129 -3.9064 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 26.9868 -6.7255 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8252 1.2732 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2973 -3.4453 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 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 27 32 1 0 26 33 1 0 25 34 1 0 21 35 1 0 35 36 1 0 36 37 2 3 37 38 1 0 38 39 1 0 39 40 1 0 40 41 2 3 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 48 49 1 0 49 50 1 0 35 51 1 0 17 52 1 0 29 24 1 0 1 53 1 0 1 54 1 0 1 55 1 0 2 56 1 0 2 57 1 0 3 58 1 0 3 59 1 0 4 60 1 0 4 61 1 0 5 62 1 0 5 63 1 0 6 64 1 0 6 65 1 0 7 66 1 0 7 67 1 0 8 68 1 0 8 69 1 0 9 70 1 0 9 71 1 0 10 72 1 0 10 73 1 0 11 74 1 0 11 75 1 0 12 76 1 0 12 77 1 0 13 78 1 0 13 79 1 0 14 80 1 0 14 81 1 0 15 82 1 0 15 83 1 0 16 84 1 0 16 85 1 0 17 86 1 0 20 87 1 0 21 88 1 0 22 89 1 0 22 90 1 0 24 91 1 0 25 92 1 0 26 93 1 0 27 94 1 0 28 95 1 0 30 96 1 0 30 97 1 0 31 98 1 0 32 99 1 0 33100 1 0 34101 1 0 35102 1 0 36103 1 0 37104 1 0 38105 1 0 38106 1 0 39107 1 0 39108 1 0 40109 1 0 41110 1 0 42111 1 0 42112 1 0 43113 1 0 43114 1 0 44115 1 0 44116 1 0 45117 1 0 45118 1 0 46119 1 0 46120 1 0 47121 1 0 47122 1 0 48123 1 0 48124 1 0 49125 1 0 49126 1 0 50127 1 0 50128 1 0 50129 1 0 51130 1 0 52131 1 0 M END

Standard InCHIKey	BLFKVICPDXPVLY-DVYLDPIQSA-N
Standard InCHI	InChI=1S/C42H79NO9/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-36(46)41(50)43-34(33-51-42-40(49)39(48)38(47)37(32-44)52-42)35(45)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h20,22,28,30,34-40,42,44-49H,3-19,21,23-27,29,31-33H2,1-2H3,(H,43,50)/b22-20+,30-28+/t34-,35+,36?,37+,38+,39-,40+,42+/m0/s1
SMILES	CCCCCCCCCCCCCCCCC(C(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCC=CCCCCCCCCC)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	741.58	Volume:	808.631 ? Van der Waals volume.
Dense:	0.917	LogP:	7.244 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.892 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.389 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	35.0	Rigid Bonds:	9.0
TPSA:	168.94 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	7.0	Rings:	1.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.027	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.741	Fsp³:	0.881
MCE-18:	25.519 ? 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:	0.659	Fluc inhibitor:	0.015 ? 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:	0.053 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.007	Promiscuous compounds:	0.0

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.402	MDCK Permeability:	-4.773
Pgp-inhibitor:	0.0	Pgp-substrate:	0.759
PAMPA:	0.001 ? 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%):	0.999	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.986
Plasma Protein Binding (PPB):	97.633%	Volume Distribution (VD):	0.524
Fu:	2.208% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.001
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.908
BSEP inhibitor:	0.04

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.889	CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.996
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):

2.608

Half-life (T1/2):

2.962

ADMET: Toxicity

hERG Blockers:	0.67	hERG Blockers (10um):	0.911
Human Hepatotoxicity (H-HT):	0.422	Drug-induced Liver Injury (DILI):	0.019
AMES Toxicity:	0.026	Rat Oral Acute Toxicity:	0.045
Maximum Recommended Daily Dose:	0.18	Skin Sensitization:	0.988
Carcinogencity:	0.008	Eye Corrosion:	0.0
Eye Irritation:	0.063	Respiratory Toxicity:	0.426
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.974
Hematotoxicity:	0.009	Drug-induced Nephrotoxicity:	0.102
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.064
A549 Cytotoxicity:	0.957	Hek293 Cytotoxicity:	0.615
BCF:	0.997 ? 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:	5.563 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.863 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.078 ? 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
NPO28204	Arisaema amurense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8882436]
NPO28204	Arisaema amurense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28204	Arisaema amurense	Species	Araceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28204	Arisaema amurense	Species	Araceae	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
Activity	2

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
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	51.6	%	PMID[7650675]
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	46.1	%	PMID[21737286]

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 NPC473581 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	20388
0.1-0.2	24749
0.2-0.3	4362
0.3-0.4	281
0.4-0.5	34
0.5-0.6	33
0.6-0.7	2
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9831	High Similarity	NPC602861
0.8235	Intermediate Similarity	NPC604736
0.8	Intermediate Similarity	NPC475603
0.8	Intermediate Similarity	NPC600808
0.6933	Remote Similarity	NPC477198
0.6571	Remote Similarity	NPC476523
0.589	Remote Similarity	NPC263545
0.589	Remote Similarity	NPC473950
0.589	Remote Similarity	NPC111567
0.589	Remote Similarity	NPC186840
0.589	Remote Similarity	NPC144916
0.589	Remote Similarity	NPC486421
0.589	Remote Similarity	NPC309898
0.589	Remote Similarity	NPC273493
0.589	Remote Similarity	NPC475125
0.589	Remote Similarity	NPC486419
0.589	Remote Similarity	NPC15851
0.589	Remote Similarity	NPC115448
0.589	Remote Similarity	NPC20819
0.589	Remote Similarity	NPC486418
0.589	Remote Similarity	NPC473604
0.589	Remote Similarity	NPC486420
0.589	Remote Similarity	NPC479188
0.589	Remote Similarity	NPC81468
0.5658	Remote Similarity	NPC158445
0.5658	Remote Similarity	NPC157353
0.5658	Remote Similarity	NPC282088
0.5634	Remote Similarity	NPC611721
0.5526	Remote Similarity	NPC156782
0.5526	Remote Similarity	NPC54961
0.5507	Remote Similarity	NPC469469
0.5405	Remote Similarity	NPC61894
0.5405	Remote Similarity	NPC297079
0.5263	Remote Similarity	NPC282705
0.5263	Remote Similarity	NPC242503
0.5263	Remote Similarity	NPC182632
0.5244	Remote Similarity	NPC8098
0.5244	Remote Similarity	NPC183449
0.5244	Remote Similarity	NPC197294

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473581 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6459
0.1-0.2	2547
0.2-0.3	137
0.3-0.4	6
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