NPASS Compound

Natural Product: NPC305186

Natural Product ID	NPC305186
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ZCXIIYVTUGFEIP-ZKKFGLNVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101692684
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides 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 3D 124131 0 0 0 0 0 0 0 0999 V2000 2.3923 2.4834 0.5365 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2353 1.0069 0.2758 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5495 0.1451 1.4518 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3427 -0.6083 1.9842 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2164 0.4052 2.0508 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0410 1.0152 0.6874 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9680 0.6801 -0.2130 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2253 0.4478 0.2297 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2156 1.4066 0.0382 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3228 1.0278 1.0418 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5520 -0.4375 0.8945 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4392 -0.9604 1.9836 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8984 -0.6592 1.7634 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3050 -1.1212 0.3530 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4672 -0.3414 -0.5962 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9996 -0.4027 -2.0052 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3572 0.2727 -1.9293 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3360 -0.4132 -1.0318 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1363 -1.3759 -1.9257 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3425 0.5791 -0.5039 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.8529 -0.1746 0.7341 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4860 -0.5085 1.3479 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7498 -1.1186 0.1355 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2111 -2.4497 0.0942 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4899 0.8431 -1.3986 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.7481 0.4557 -1.1506 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.5961 0.8844 -2.2304 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8531 0.6736 -2.3044 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8075 1.5416 -3.1310 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4721 1.5670 -2.6761 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0427 -0.8185 -0.4914 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9329 -2.3269 -0.6036 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1221 -0.2314 -1.5232 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8273 1.2335 -1.3285 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8960 -0.9227 -1.3808 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6218 1.4262 2.9029 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5895 -1.2001 3.1992 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4723 -0.8293 1.0674 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6269 -0.7924 1.8170 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8339 -2.1124 2.5074 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9358 -2.8687 1.7961 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2463 -2.0684 1.9204 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8733 -0.6119 1.8927 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9697 0.2947 1.4056 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3128 0.0499 0.0958 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3187 0.9062 -0.3445 C 0 0 1 0 0 0 0 0 0 0 0 0 10.5951 0.1302 -0.5805 C 0 0 1 0 0 0 0 0 0 0 0 0 11.7458 0.9968 -0.9498 C 0 0 2 0 0 0 0 0 0 0 0 0 11.3151 2.1835 -1.7339 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9053 2.2029 -2.2041 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7852 1.7294 -3.6576 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8812 0.3751 -3.8063 O 0 0 0 0 0 0 0 0 0 0 0 0 8.9533 1.6939 -1.3875 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6138 3.3367 -0.9651 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5812 0.2143 -1.7881 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9721 -0.5661 0.5917 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7498 -0.3922 1.0823 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8042 -2.4420 3.1394 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6242 -2.9172 0.4426 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1456 -1.8755 3.8391 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2374 2.8905 -0.0877 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5087 3.0670 0.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6441 2.7264 1.5777 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9359 0.7265 -0.5594 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9979 0.7590 2.2822 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0753 -1.3772 1.2382 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6997 -0.0357 2.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1881 2.0871 0.7929 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8655 2.4375 0.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8733 1.2084 2.0414 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1974 1.6681 0.9584 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5566 -0.9345 1.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1389 -0.3913 2.9147 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2670 -2.0286 2.2218 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0472 0.4072 1.9157 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4644 -1.3062 2.4739 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8988 -2.1782 0.3235 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4886 0.7254 -0.2952 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3606 0.3083 -2.6036 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0298 -1.4043 -2.4256 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1698 1.2987 -1.5060 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7357 0.4068 -2.9563 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5360 -1.6861 -2.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0701 -0.9468 -2.2838 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4123 -2.3063 -1.3773 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8428 1.5069 -0.1624 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4209 0.4733 1.4116 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3651 -1.0757 0.3949 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5639 -1.2272 2.1735 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0565 0.4560 1.6346 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7139 -2.7170 0.8782 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0273 -0.0926 -0.2573 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8746 1.1017 -3.4721 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1387 2.6168 -2.4628 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8332 -2.8287 0.3805 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9837 -2.6077 -1.1504 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7346 -2.7556 -1.2321 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4845 -0.4839 -2.5339 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7625 1.8187 -1.4281 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0953 1.5170 -2.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3382 -0.8533 -2.1779 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2656 2.3126 2.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8155 -1.0229 3.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4838 0.0287 2.5811 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9227 -2.7489 2.4465 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0450 -3.8594 2.2585 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8874 -2.3847 1.0818 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6363 -0.3054 2.9472 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8713 0.2142 2.0789 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6590 1.3641 1.4929 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5544 1.5776 0.5290 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4382 -0.6547 -1.3385 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3432 1.3100 -0.0615 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9636 2.3268 -2.6543 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6482 3.3144 -2.3015 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6562 2.1967 -4.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8819 2.1847 -4.1142 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7598 0.0266 -4.0907 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5821 3.4042 -0.8012 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0495 -0.4395 -1.2061 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7720 -0.1732 1.0110 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9862 -3.4048 3.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7108 -2.6248 0.2324 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4518 -2.2746 4.4253 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 6 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 6 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 20 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 27 29 1 0 29 30 1 0 15 31 1 0 31 32 1 1 31 33 1 0 33 34 1 0 33 35 1 0 5 36 1 0 4 37 1 0 3 38 1 0 38 39 1 0 39 40 1 0 40 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 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 48 55 1 0 47 56 1 0 43 57 1 0 42 58 1 0 41 59 1 0 40 60 1 0 7 2 1 0 34 9 1 0 57 39 1 0 31 11 1 0 53 46 1 0 23 14 1 0 30 25 1 0 23 18 1 0 1 61 1 0 1 62 1 0 1 63 1 0 2 64 1 6 3 65 1 1 4 66 1 6 5 67 1 1 6 68 1 1 9 69 1 1 10 70 1 0 10 71 1 0 11 72 1 1 12 73 1 0 12 74 1 0 13 75 1 0 13 76 1 0 14 77 1 1 15 78 1 1 16 79 1 0 16 80 1 0 17 81 1 0 17 82 1 0 19 83 1 0 19 84 1 0 19 85 1 0 20 86 1 1 21 87 1 0 21 88 1 0 22 89 1 0 22 90 1 0 24 91 1 0 26 92 1 0 30 93 1 0 30 94 1 0 32 95 1 0 32 96 1 0 32 97 1 0 33 98 1 6 34 99 1 0 34100 1 0 35101 1 0 36102 1 0 37103 1 0 39104 1 1 40105 1 1 41106 1 1 42107 1 6 43108 1 1 44109 1 0 44110 1 0 46111 1 1 47112 1 6 48113 1 1 49114 1 6 50115 1 6 51116 1 0 51117 1 0 52118 1 0 54119 1 0 55120 1 0 56121 1 0 58122 1 0 59123 1 0 60124 1 0 M END

Standard InCHIKey	ZCXIIYVTUGFEIP-ZKKFGLNVSA-N
Standard InCHI	InChI=1S/C41H64O19/c1-16-35(60-38-33(51)30(48)28(46)24(59-38)15-55-36-32(50)29(47)27(45)23(13-42)58-36)31(49)34(52)37(56-16)57-19-11-18-4-5-22-21(40(18,3)25(43)12-19)6-8-39(2)20(7-9-41(22,39)53)17-10-26(44)54-14-17/h10,16,18-25,27-38,42-43,45-53H,4-9,11-15H2,1-3H3/t16-,18+,19+,20+,21-,22+,23+,24+,25+,27+,28+,29-,30-,31-,32+,33+,34+,35-,36+,37-,38-,39+,40-,41-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1C[C@H]2CC[C@@H]3[C@H](CC[C@]4(C)[C@H](CC[C@]34O)C3=CC(=O)OC3)[C@@]2(C)[C@@H](C1)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	860.4	Volume:	810.982 ? Van der Waals volume.
Dense:	1.061	LogP:	-1.417 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.188 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.349 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	44.0
TPSA:	304.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.082	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.191	Fsp³:	0.927
MCE-18:	158.785 ? 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:	0.615	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.165	Promiscuous compounds:	0.34

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.615	MDCK Permeability:	-5.079
Pgp-inhibitor:	0.0	Pgp-substrate:	0.99
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):	0.986
20% Bioavailability (F20%):	0.894	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.521
Plasma Protein Binding (PPB):	52.598%	Volume Distribution (VD):	-0.446
Fu:	36.628% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.001
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.011	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:	0.647	CYP3A4-substrate:	0.005
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.462
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):

0.31

Half-life (T1/2):

4.165

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.075
Human Hepatotoxicity (H-HT):	0.768	Drug-induced Liver Injury (DILI):	0.893
AMES Toxicity:	0.982	Rat Oral Acute Toxicity:	0.439
Maximum Recommended Daily Dose:	0.983	Skin Sensitization:	1.0
Carcinogencity:	0.352	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.452
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.707	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.999	RPMI-8226 Immunitoxicity:	0.915
A549 Cytotoxicity:	0.977	Hek293 Cytotoxicity:	0.973
BCF:	0.689 ? 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:	3.177 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.336 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.585 ? 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
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	leaves and twigs	n.a.	n.a.	PMID[21435874]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29118	Euonymus alatus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29118	Euonymus alatus	Species	Celastraceae	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

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 NPC305186 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	16228
0.1-0.2	28537
0.2-0.3	4049
0.3-0.4	835
0.4-0.5	93
0.5-0.6	60
0.6-0.7	36
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	Natural Product ID
0.7582	Intermediate Similarity	NPC236973
0.7582	Intermediate Similarity	NPC32177
0.7582	Intermediate Similarity	NPC469756
0.7582	Intermediate Similarity	NPC275901
0.75	Intermediate Similarity	NPC188234
0.7473	Intermediate Similarity	NPC30483
0.7473	Intermediate Similarity	NPC470897
0.7356	Intermediate Similarity	NPC196429
0.7245	Intermediate Similarity	NPC486144
0.7245	Intermediate Similarity	NPC486145
0.7245	Intermediate Similarity	NPC486147
0.7245	Intermediate Similarity	NPC475590
0.7245	Intermediate Similarity	NPC486136
0.7245	Intermediate Similarity	NPC486148
0.6703	Remote Similarity	NPC5311
0.6703	Remote Similarity	NPC77299
0.6703	Remote Similarity	NPC480906
0.6702	Remote Similarity	NPC480907
0.6667	Remote Similarity	NPC474423
0.6633	Remote Similarity	NPC486143
0.6633	Remote Similarity	NPC486135
0.6633	Remote Similarity	NPC486142
0.6633	Remote Similarity	NPC486137
0.6633	Remote Similarity	NPC486149
0.663	Remote Similarity	NPC480914
0.6602	Remote Similarity	NPC475419
0.6598	Remote Similarity	NPC32793
0.6598	Remote Similarity	NPC116075
0.6566	Remote Similarity	NPC232785
0.6566	Remote Similarity	NPC486139
0.6538	Remote Similarity	NPC474908
0.6538	Remote Similarity	NPC486134
0.6538	Remote Similarity	NPC486141
0.6535	Remote Similarity	NPC486131
0.6476	Remote Similarity	NPC486150
0.6471	Remote Similarity	NPC486128
0.6465	Remote Similarity	NPC125077
0.6304	Remote Similarity	NPC473852
0.6286	Remote Similarity	NPC120390
0.6263	Remote Similarity	NPC480910
0.6263	Remote Similarity	NPC480909
0.62	Remote Similarity	NPC610296
0.6168	Remote Similarity	NPC486133
0.6162	Remote Similarity	NPC292467
0.6154	Remote Similarity	NPC479360
0.6154	Remote Similarity	NPC479359
0.6105	Remote Similarity	NPC76572
0.6105	Remote Similarity	NPC193382
0.61	Remote Similarity	NPC240070
0.604	Remote Similarity	NPC264336
0.5957	Remote Similarity	NPC99620
0.5941	Remote Similarity	NPC486130
0.5895	Remote Similarity	NPC84987
0.5893	Remote Similarity	NPC486152
0.5882	Remote Similarity	NPC475629
0.5882	Remote Similarity	NPC486127
0.5865	Remote Similarity	NPC329986
0.5865	Remote Similarity	NPC140092
0.5865	Remote Similarity	NPC486146
0.5842	Remote Similarity	NPC40749
0.5833	Remote Similarity	NPC74259
0.5833	Remote Similarity	NPC469750
0.5825	Remote Similarity	NPC59288
0.5825	Remote Similarity	NPC208193
0.5818	Remote Similarity	NPC488945
0.5818	Remote Similarity	NPC488946
0.581	Remote Similarity	NPC486138
0.581	Remote Similarity	NPC276838
0.5784	Remote Similarity	NPC475556
0.5784	Remote Similarity	NPC311706
0.578	Remote Similarity	NPC194716
0.5612	Remote Similarity	NPC243196
0.5607	Remote Similarity	NPC479357
0.5607	Remote Similarity	NPC486132
0.5577	Remote Similarity	NPC231518
0.5577	Remote Similarity	NPC488944
0.5463	Remote Similarity	NPC476221
0.5463	Remote Similarity	NPC477709
0.5357	Remote Similarity	NPC486140
0.5354	Remote Similarity	NPC480915
0.5351	Remote Similarity	NPC488947
0.5347	Remote Similarity	NPC471353
0.5327	Remote Similarity	NPC469749
0.5273	Remote Similarity	NPC488943
0.5273	Remote Similarity	NPC488942
0.5248	Remote Similarity	NPC146456
0.5243	Remote Similarity	NPC72260
0.5221	Remote Similarity	NPC117445
0.5221	Remote Similarity	NPC308262
0.52	Remote Similarity	NPC157376
0.52	Remote Similarity	NPC142066
0.52	Remote Similarity	NPC603972
0.5196	Remote Similarity	NPC305574
0.5182	Remote Similarity	NPC475219
0.5152	Remote Similarity	NPC99728
0.5152	Remote Similarity	NPC87250
0.5152	Remote Similarity	NPC244402
0.5152	Remote Similarity	NPC50305
0.5138	Remote Similarity	NPC146857
0.5128	Remote Similarity	NPC286809
0.5088	Remote Similarity	NPC329675
0.505	Remote Similarity	NPC17896
0.505	Remote Similarity	NPC469755
0.505	Remote Similarity	NPC284406
0.505	Remote Similarity	NPC197707
0.505	Remote Similarity	NPC251866
0.5049	Remote Similarity	NPC179412
0.5049	Remote Similarity	NPC471356
0.5047	Remote Similarity	NPC479353
0.5047	Remote Similarity	NPC479354

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC305186 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6497
0.1-0.2	2568
0.2-0.3	64
0.3-0.4	8
0.4-0.5	10
0.5-0.6	3
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
0.5577	Remote Similarity	NPD8033	Approved
0.5243	Remote Similarity	NPD8294	Phase 4
0.505	Remote Similarity	NPD7319	Approved

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