NPASS Compound

Natural Product: NPC601290

Natural Product ID	NPC601290
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YTPBUIWNJRGZFW-WVOFOFDDSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL5285494
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 139146 0 0 0 0 0 0 0 0999 V2000 5.3251 -0.4535 -4.7707 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6657 0.0439 -3.3580 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4476 1.3492 -3.6212 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5926 -0.9104 -2.7369 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1649 -1.6156 -1.5069 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3380 -0.8168 -0.5795 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3581 -0.0431 0.2554 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3973 1.2305 0.1549 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2417 -0.6102 1.1128 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1754 0.0914 1.8723 C 0 0 2 0 0 0 0 0 0 0 0 0 9.4643 -0.3104 1.6762 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4153 0.5105 2.2128 C 0 0 2 0 0 0 0 0 0 0 0 0 11.4542 -0.2680 2.9929 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9181 -0.9803 4.0499 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8739 1.5946 3.0967 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6090 2.7772 2.3675 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7179 1.1916 3.9567 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1549 0.8657 5.2480 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8747 0.0826 3.3535 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5446 0.4079 3.6154 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7042 -1.7314 0.4384 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3855 -2.3362 0.1704 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4308 -1.4773 -0.6833 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5435 -2.1430 -2.0398 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0668 -0.1575 -0.5650 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5271 0.7395 0.2023 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2784 0.5141 0.9964 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3922 -0.2774 0.1161 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0424 -0.3274 0.5989 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2468 -0.9919 1.9040 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4751 1.1272 0.8162 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9319 1.3080 0.9047 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8444 0.5345 0.0454 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0888 0.2995 0.6419 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1510 0.9451 0.0740 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5849 1.8896 0.9545 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5489 1.6223 1.8486 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9354 1.4233 3.1901 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6119 1.1626 4.2154 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5693 1.5278 3.3172 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4237 0.4281 1.6254 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6265 0.8994 1.0921 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8796 -0.6182 0.7207 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9825 -1.4244 1.3960 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2483 0.0844 -0.4608 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2107 0.9255 -1.0231 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5041 0.6415 -2.3375 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0932 1.7885 -3.0718 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5378 2.9501 -2.4326 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0439 2.9047 -2.3898 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.5131 2.9256 -1.0768 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6105 1.7069 -3.1414 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.9772 1.6708 -2.9420 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0088 0.4844 -2.4704 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2853 -0.6771 -3.1556 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3259 -0.7756 -0.4483 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9314 -1.9160 0.3155 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8240 -0.9339 -1.9071 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8606 -0.7761 -0.5571 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.3394 -2.0497 -1.1889 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1206 -1.9375 -1.5410 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9906 -1.5608 -0.3111 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8272 -2.7383 0.6025 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3658 0.1637 -1.2027 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3796 0.3370 -2.6575 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4830 0.1919 -5.1322 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2121 -0.3848 -5.4305 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9270 -1.4891 -4.6878 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2544 1.0746 -4.3265 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7449 2.0726 -4.0376 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8536 1.6471 -2.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8930 -1.7235 -3.4684 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5969 -0.4326 -2.5207 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7291 -2.6223 -1.7613 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1154 -1.9134 -0.9509 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0530 1.1785 1.5750 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9881 1.0334 1.3895 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0716 -0.9282 2.3166 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2236 0.4282 3.4343 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7137 -1.9257 3.7838 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7106 1.8925 3.7949 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9037 3.2524 2.9097 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0914 2.1208 4.1010 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4859 1.1179 5.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1956 -0.8651 3.8172 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4135 1.3876 3.7909 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7666 -1.2708 1.4791 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4419 -2.5889 0.5584 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5123 -3.3543 -0.2449 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9511 -2.5118 1.2002 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5466 -2.2724 -2.4318 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8697 -1.8071 -2.8054 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2798 -3.2307 -1.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9754 1.7497 0.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8297 1.5003 1.2932 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5036 0.0268 1.9711 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2881 0.3386 -0.8421 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3076 -0.8162 2.5134 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0135 -0.4467 2.5453 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5849 -2.0239 1.9072 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0894 1.8015 0.0259 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0435 1.5122 1.7807 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2138 2.4043 0.8257 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2250 1.0767 1.9782 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0871 1.2225 -0.8247 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7253 1.5209 -0.8089 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1890 2.5598 2.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0389 1.2801 4.1373 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7147 -0.0671 2.5899 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2915 0.1785 0.9825 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7063 -1.2441 0.2999 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1033 -2.3502 1.0737 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8949 -0.6686 -1.1586 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9353 -0.2109 -2.7227 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0966 3.0169 -1.4047 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1993 3.7964 -3.0456 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4308 3.8229 -2.8713 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4073 3.8094 -0.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3970 1.7615 -4.2158 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3846 2.3133 -3.6045 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4444 0.4056 -1.4731 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5208 -1.2920 -3.0501 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8838 -2.2024 -0.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2427 -1.5988 1.3569 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3274 -2.8132 0.4013 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0151 -2.0038 -2.1034 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0728 -0.5437 -2.6269 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7346 -0.3218 -2.0379 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6380 0.0057 -1.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8479 -2.0836 -2.2078 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6546 -2.9707 -0.7187 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1525 -1.0515 -2.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3647 -2.8880 -1.9787 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1456 -3.2661 0.5198 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0151 -2.5889 1.6522 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5442 -3.5303 0.2224 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7265 1.1712 -0.8017 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1756 1.4382 -2.9093 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5154 -0.0989 -3.2237 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 1 7 8 2 0 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 6 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 29 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 2 0 38 40 1 0 37 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 43 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 50 52 1 0 52 53 1 0 52 54 1 0 54 55 1 0 33 56 1 0 56 57 1 0 56 58 1 0 56 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 1 25 64 1 0 64 65 1 0 65 2 1 0 64 6 1 0 19 10 1 0 62 23 1 0 62 28 1 0 59 29 1 0 45 35 1 0 54 47 1 0 1 66 1 0 1 67 1 0 1 68 1 0 3 69 1 0 3 70 1 0 3 71 1 0 4 72 1 0 4 73 1 0 5 74 1 0 5 75 1 0 10 76 1 6 12 77 1 6 13 78 1 0 13 79 1 0 14 80 1 0 15 81 1 1 16 82 1 0 17 83 1 1 18 84 1 0 19 85 1 1 20 86 1 0 21 87 1 0 21 88 1 0 22 89 1 0 22 90 1 0 24 91 1 0 24 92 1 0 24 93 1 0 26 94 1 0 27 95 1 0 27 96 1 0 28 97 1 6 30 98 1 0 30 99 1 0 30100 1 0 31101 1 0 31102 1 0 32103 1 0 32104 1 0 33105 1 6 35106 1 6 37107 1 1 40108 1 0 41109 1 1 42110 1 0 43111 1 6 44112 1 0 45113 1 6 47114 1 6 49115 1 0 49116 1 0 50117 1 6 51118 1 0 52119 1 6 53120 1 0 54121 1 1 55122 1 0 57123 1 0 57124 1 0 57125 1 0 58126 1 0 58127 1 0 58128 1 0 59129 1 6 60130 1 0 60131 1 0 61132 1 0 61133 1 0 63134 1 0 63135 1 0 63136 1 0 64137 1 1 65138 1 0 65139 1 0 M END

Standard InCHIKey	YTPBUIWNJRGZFW-WVOFOFDDSA-N
Standard InCHI	InChI=1S/C47H74O18/c1-42(2)14-16-47(41(59)65-39-34(56)30(52)29(51)24(19-48)61-39)17-15-45(6)21(22(47)18-42)8-9-26-44(5)12-11-27(43(3,4)25(44)10-13-46(26,45)7)62-40-36(32(54)31(53)35(63-40)37(57)58)64-38-33(55)28(50)23(49)20-60-38/h8,22-36,38-40,48-56H,9-20H2,1-7H3,(H,57,58)/t22-,23-,24+,25-,26+,27-,28-,29+,30-,31-,32-,33+,34+,35-,36+,38-,39-,40+,44-,45+,46+,47-/m0/s1
SMILES	CC1(C)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6OC[C@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	926.49	Volume:	903.331 ? Van der Waals volume.
Dense:	1.026	LogP:	1.896 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.531 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.145 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	46.0
TPSA:	291.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.092	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.248	Fsp³:	0.915
MCE-18:	175.0 ? 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:	0.868	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.178	Promiscuous compounds:	0.136

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.152	MDCK Permeability:	-5.073
Pgp-inhibitor:	0.0	Pgp-substrate:	0.036
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):	0.443
20% Bioavailability (F20%):	0.37	30% Bioavailability (F30%):	0.978
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.759
Plasma Protein Binding (PPB):	68.448%	Volume Distribution (VD):	-0.497
Fu:	22.985% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.995	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.014
HLM stability:	0.046 ? 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):

-0.043

Half-life (T1/2):

3.483

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.004
Human Hepatotoxicity (H-HT):	0.781	Drug-induced Liver Injury (DILI):	0.965
AMES Toxicity:	0.888	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.091	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.005
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.623	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.838	RPMI-8226 Immunitoxicity:	0.122
A549 Cytotoxicity:	0.6	Hek293 Cytotoxicity:	0.143
BCF:	0.816 ? 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:	3.6 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.253 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.359 ? 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
NPO23343	Cynara cardunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23343	Cynara cardunculus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO23343	Cynara cardunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23343	Cynara cardunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23343	Cynara cardunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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

Activity Type	# Activity
Cell line	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
NPT1135	Cell line	Hepatocyte	Rattus norvegicus	Activity	=	28.0	%	PMID[29353722]

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 NPC601290 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	21526
0.1-0.2	23877
0.2-0.3	3115
0.3-0.4	668
0.4-0.5	309
0.5-0.6	84
0.6-0.7	86
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC301449
0.9255	High Similarity	NPC251768
0.8431	Intermediate Similarity	NPC187290
0.8351	Intermediate Similarity	NPC469946
0.8265	Intermediate Similarity	NPC192791
0.8061	Intermediate Similarity	NPC157868
0.7941	Intermediate Similarity	NPC297263
0.7864	Intermediate Similarity	NPC64715
0.7857	Intermediate Similarity	NPC258617
0.7843	Intermediate Similarity	NPC475591
0.7843	Intermediate Similarity	NPC236870
0.757	Intermediate Similarity	NPC31838
0.757	Intermediate Similarity	NPC481078
0.7568	Intermediate Similarity	NPC470218
0.7549	Intermediate Similarity	NPC112352
0.75	Intermediate Similarity	NPC63159
0.7404	Intermediate Similarity	NPC159309
0.7404	Intermediate Similarity	NPC86222
0.7353	Intermediate Similarity	NPC473884
0.7273	Intermediate Similarity	NPC90856
0.7257	Intermediate Similarity	NPC283417
0.7257	Intermediate Similarity	NPC200049
0.7238	Intermediate Similarity	NPC40775
0.7222	Intermediate Similarity	NPC481079
0.7212	Intermediate Similarity	NPC242840
0.7168	Intermediate Similarity	NPC123199
0.713	Intermediate Similarity	NPC114484
0.7129	Intermediate Similarity	NPC48499
0.7019	Intermediate Similarity	NPC295371
0.6983	Remote Similarity	NPC4749
0.6972	Remote Similarity	NPC281148
0.6944	Remote Similarity	NPC222580
0.6875	Remote Similarity	NPC11242
0.6847	Remote Similarity	NPC480473
0.6847	Remote Similarity	NPC480474
0.6842	Remote Similarity	NPC79643
0.6827	Remote Similarity	NPC475516
0.6765	Remote Similarity	NPC214484
0.6759	Remote Similarity	NPC480475
0.6729	Remote Similarity	NPC75417
0.6724	Remote Similarity	NPC135904
0.6698	Remote Similarity	NPC472949
0.6667	Remote Similarity	NPC235405
0.6639	Remote Similarity	NPC57484
0.6634	Remote Similarity	NPC128925
0.6606	Remote Similarity	NPC46665
0.6604	Remote Similarity	NPC249848
0.6604	Remote Similarity	NPC107966
0.6602	Remote Similarity	NPC204458
0.6549	Remote Similarity	NPC295823
0.6549	Remote Similarity	NPC187618
0.6549	Remote Similarity	NPC174720
0.6549	Remote Similarity	NPC475467
0.6542	Remote Similarity	NPC39211
0.6514	Remote Similarity	NPC30735
0.6504	Remote Similarity	NPC302543
0.65	Remote Similarity	NPC21691
0.648	Remote Similarity	NPC250247
0.6466	Remote Similarity	NPC60557
0.6466	Remote Similarity	NPC67857
0.6455	Remote Similarity	NPC10607
0.6423	Remote Similarity	NPC481081
0.6422	Remote Similarity	NPC223301
0.6422	Remote Similarity	NPC171544
0.6417	Remote Similarity	NPC481080
0.6408	Remote Similarity	NPC209894
0.6396	Remote Similarity	NPC235438
0.6393	Remote Similarity	NPC41061
0.6393	Remote Similarity	NPC227551
0.6387	Remote Similarity	NPC191827
0.6381	Remote Similarity	NPC1046
0.6381	Remote Similarity	NPC78046
0.6372	Remote Similarity	NPC247315
0.6372	Remote Similarity	NPC482728
0.633	Remote Similarity	NPC263756
0.633	Remote Similarity	NPC213674
0.6306	Remote Similarity	NPC11551
0.629	Remote Similarity	NPC236638
0.629	Remote Similarity	NPC294453
0.629	Remote Similarity	NPC305981
0.6263	Remote Similarity	NPC167383
0.6261	Remote Similarity	NPC80986
0.625	Remote Similarity	NPC118440
0.624	Remote Similarity	NPC261506
0.624	Remote Similarity	NPC4328
0.6239	Remote Similarity	NPC488561
0.6228	Remote Similarity	NPC104372
0.6216	Remote Similarity	NPC160415
0.6195	Remote Similarity	NPC31193
0.6186	Remote Similarity	NPC475287
0.6186	Remote Similarity	NPC313110
0.6179	Remote Similarity	NPC265841
0.614	Remote Similarity	NPC302887
0.6139	Remote Similarity	NPC237503
0.6136	Remote Similarity	NPC475368
0.6121	Remote Similarity	NPC160452
0.6087	Remote Similarity	NPC114692
0.608	Remote Similarity	NPC43550
0.6075	Remote Similarity	NPC29069
0.6068	Remote Similarity	NPC104137
0.6068	Remote Similarity	NPC26626
0.6066	Remote Similarity	NPC488560
0.6063	Remote Similarity	NPC70809
0.6055	Remote Similarity	NPC139894
0.6055	Remote Similarity	NPC309780
0.6053	Remote Similarity	NPC475504
0.6053	Remote Similarity	NPC131469
0.605	Remote Similarity	NPC300419
0.6036	Remote Similarity	NPC475171
0.6034	Remote Similarity	NPC218954
0.6018	Remote Similarity	NPC44716
0.6018	Remote Similarity	NPC164389
0.6	Remote Similarity	NPC95437
0.6	Remote Similarity	NPC127056
0.6	Remote Similarity	NPC256798
0.5984	Remote Similarity	NPC475160
0.5984	Remote Similarity	NPC473714
0.5983	Remote Similarity	NPC120116
0.5983	Remote Similarity	NPC241909
0.5981	Remote Similarity	NPC189884
0.5981	Remote Similarity	NPC138334
0.5948	Remote Similarity	NPC236657
0.5929	Remote Similarity	NPC309714
0.592	Remote Similarity	NPC488308
0.5917	Remote Similarity	NPC76972
0.5917	Remote Similarity	NPC469782
0.5917	Remote Similarity	NPC204414
0.5887	Remote Similarity	NPC71391
0.5873	Remote Similarity	NPC271610
0.5873	Remote Similarity	NPC312650
0.5868	Remote Similarity	NPC123522
0.5794	Remote Similarity	NPC473645
0.5789	Remote Similarity	NPC471965
0.5789	Remote Similarity	NPC482749
0.5789	Remote Similarity	NPC117714
0.5789	Remote Similarity	NPC30289
0.5781	Remote Similarity	NPC202828
0.5781	Remote Similarity	NPC119592
0.5752	Remote Similarity	NPC80843
0.5736	Remote Similarity	NPC298034
0.5736	Remote Similarity	NPC71065
0.5726	Remote Similarity	NPC79718
0.5726	Remote Similarity	NPC602995
0.5714	Remote Similarity	NPC470518
0.5714	Remote Similarity	NPC476068
0.5714	Remote Similarity	NPC484061
0.5714	Remote Similarity	NPC473373
0.5714	Remote Similarity	NPC484062
0.5714	Remote Similarity	NPC150400
0.5703	Remote Similarity	NPC293330
0.5702	Remote Similarity	NPC469945
0.5702	Remote Similarity	NPC288205
0.5702	Remote Similarity	NPC51465
0.5691	Remote Similarity	NPC284449
0.5691	Remote Similarity	NPC475899
0.5669	Remote Similarity	NPC286457
0.5649	Remote Similarity	NPC488309
0.5648	Remote Similarity	NPC480937
0.5645	Remote Similarity	NPC166422
0.5645	Remote Similarity	NPC470476
0.5641	Remote Similarity	NPC609763
0.5636	Remote Similarity	NPC164194
0.5635	Remote Similarity	NPC85154
0.5635	Remote Similarity	NPC192765
0.563	Remote Similarity	NPC482737
0.563	Remote Similarity	NPC23275
0.563	Remote Similarity	NPC477075
0.5625	Remote Similarity	NPC470876
0.562	Remote Similarity	NPC75287
0.5614	Remote Similarity	NPC22956
0.5603	Remote Similarity	NPC488526
0.56	Remote Similarity	NPC100639
0.5596	Remote Similarity	NPC161434
0.5591	Remote Similarity	NPC178264
0.5581	Remote Similarity	NPC65105
0.5581	Remote Similarity	NPC476779
0.5575	Remote Similarity	NPC58448
0.5575	Remote Similarity	NPC482748
0.5574	Remote Similarity	NPC470475
0.5565	Remote Similarity	NPC165204
0.5538	Remote Similarity	NPC136768
0.5537	Remote Similarity	NPC469947
0.5537	Remote Similarity	NPC207738
0.5537	Remote Similarity	NPC480948
0.553	Remote Similarity	NPC224381
0.5528	Remote Similarity	NPC473824
0.5528	Remote Similarity	NPC610204
0.5522	Remote Similarity	NPC489209
0.552	Remote Similarity	NPC257211
0.5517	Remote Similarity	NPC485563
0.55	Remote Similarity	NPC324875
0.55	Remote Similarity	NPC292677
0.55	Remote Similarity	NPC291903
0.55	Remote Similarity	NPC477079
0.5492	Remote Similarity	NPC480939
0.5487	Remote Similarity	NPC59804
0.5481	Remote Similarity	NPC480422
0.5478	Remote Similarity	NPC161674
0.5476	Remote Similarity	NPC471550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC601290 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	2590
0.2-0.3	56
0.3-0.4	5
0.4-0.5	1
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
0.5085	Remote Similarity	NPD8328	Phase 2

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