NPASS Compound

Natural Product: NPC539423

Natural Product ID	NPC539423
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Glucogitaloxin
IUPAC Name	[(3~{S},5~{R},8~{R},9~{S},10~{S},13~{R},14~{S},16~{S},17~{R})-14-hydroxy-3-[(2~{R},4~{S},5~{S},6~{R})-4-hydroxy-5-[(2~{S},4~{S},5~{S},6~{R})-4-hydroxy-5-[(2~{S},4~{S},5~{S},6~{R})-4-hydroxy-6-methyl-5-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-6-methyl-tetrahydropyran-2-yl]oxy-10,13-dimethyl-17-(5-oxo-2~{H}-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-16-yl] formate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
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 142150 0 0 0 0 0 0 0 0999 V2000 -0.6438 -1.3529 1.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3900 -0.7710 0.2237 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0863 -0.9292 -1.1257 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9159 -0.0946 -1.5633 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0482 -0.1248 -0.8019 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2234 -0.2801 -1.4973 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8489 -1.6512 -1.2710 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3649 -1.5603 -1.2630 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8525 -0.6702 -0.1485 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7184 -1.4479 1.1453 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0866 0.6393 -0.0819 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0173 1.8324 -0.0258 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1679 1.6681 0.9243 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8614 0.3068 0.7873 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2878 -0.3068 -0.4486 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0837 -1.4451 -0.9892 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4561 -0.8673 -1.2830 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1360 -0.5346 0.0151 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.4261 -1.8243 0.7247 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3653 0.2807 -0.2962 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.6026 -0.4534 -0.5097 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.7910 -0.2695 0.0744 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7702 -1.2101 -0.4195 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.9916 -1.3005 -0.0663 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.1354 -2.0011 -1.3529 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8023 -1.6065 -1.4300 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4057 1.3737 0.7248 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.6209 0.9651 2.0484 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4756 1.5502 2.9536 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1326 2.5405 2.5910 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8992 1.7615 0.7040 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3227 0.3569 0.9073 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6974 0.0134 2.2301 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2011 0.8326 -1.2847 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3544 1.3392 -1.4793 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2146 1.6450 -0.0104 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2220 2.9235 0.2117 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7614 0.6379 0.5722 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0503 0.8535 0.1585 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9303 1.2830 1.1482 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8504 0.0368 1.3641 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2278 -0.3592 -0.0454 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9229 -1.5501 -0.0120 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1478 0.7516 -0.5615 C 0 0 2 0 0 0 0 0 0 0 0 0 6.2907 0.6999 0.2345 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4332 0.3513 -0.4539 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4542 1.4269 -0.6059 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2438 1.5682 0.6630 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3555 2.4095 0.4577 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7780 0.2109 1.0474 C 0 0 2 0 0 0 0 0 0 0 0 0 10.6811 -0.1826 0.0836 O 0 0 0 0 0 0 0 0 0 0 0 0 11.9724 -0.3828 0.5254 C 0 0 2 0 0 0 0 0 0 0 0 0 12.9205 0.3167 -0.1567 O 0 0 0 0 0 0 0 0 0 0 0 0 14.0928 -0.3168 -0.4477 C 0 0 2 0 0 0 0 0 0 0 0 0 14.8496 0.6062 -1.4232 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0836 0.7848 -2.5882 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9947 -1.6402 -1.1239 C 0 0 1 0 0 0 0 0 0 0 0 0 15.0746 -2.4219 -0.6470 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7459 -2.3819 -0.7762 C 0 0 2 0 0 0 0 0 0 0 0 0 11.8481 -2.2562 -1.8257 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2255 -1.8890 0.5328 C 0 0 1 0 0 0 0 0 0 0 0 0 13.0578 -2.2262 1.5951 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6086 -0.7468 1.1407 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6182 -0.3836 2.2115 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9470 -0.8710 -0.0686 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4036 2.0506 -0.4720 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3848 2.1361 -1.6167 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7436 2.2898 0.7057 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1735 -1.9086 2.0055 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3979 -0.6178 1.4751 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1850 -2.1416 0.5609 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3248 -1.3842 0.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0748 -0.2386 -2.6384 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9630 -0.2809 -2.5747 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6009 -2.3549 -2.1177 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4818 -2.1514 -0.3742 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6738 -1.1742 -2.2538 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7543 -2.5829 -1.0968 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5709 -2.1049 1.3626 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4844 -0.7189 1.9695 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8219 -2.1301 1.1438 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5094 0.6555 0.8634 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3905 2.6739 0.3999 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3039 2.2115 -1.0291 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8615 2.4928 0.7598 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7551 1.8036 1.9614 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4465 -0.3004 1.6458 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2304 0.4441 -1.2962 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6284 -1.7208 -1.9818 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0998 -2.3574 -0.3987 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0205 -1.6027 -1.8328 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2713 0.0813 -1.8503 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7475 -1.8708 1.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1323 -2.7100 0.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4584 -1.8906 1.1358 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1734 0.8409 -1.2789 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9966 0.4826 0.8135 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1034 -2.4460 -1.1928 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5748 -1.2286 -2.4624 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0118 2.2197 0.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5759 1.1622 3.9540 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6207 2.2065 -0.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7792 2.3974 1.6004 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3216 0.6862 2.8600 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8612 1.0358 -2.1582 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6215 1.7662 -1.1002 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6083 1.4019 -1.9951 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0956 2.0138 -1.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1945 1.4242 0.4653 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2648 3.5625 -0.3610 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7090 0.7892 1.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4790 1.4852 2.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2922 -0.7158 1.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7305 0.4400 1.8853 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3339 -0.4242 -0.7064 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7937 -2.0608 0.8377 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3807 0.5589 -1.6322 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0613 0.1647 -1.5213 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1886 1.1697 -1.4195 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0189 2.3938 -0.9439 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6058 1.9910 1.4798 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5326 2.5343 -0.4925 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2488 0.2793 2.0524 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0095 -0.1088 1.6211 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7459 -0.3554 0.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8447 0.2174 -1.6663 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9863 1.6192 -0.9840 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4511 0.2117 -3.3226 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1552 -1.5655 -2.2197 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8599 -1.8192 -0.6637 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9548 -3.4877 -0.6385 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1519 -1.5724 -1.7006 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2451 -2.3723 0.7315 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6952 -1.7947 2.4022 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9638 -1.7810 1.3893 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9272 -0.7606 3.2148 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6749 -0.9586 1.9947 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3536 0.6676 2.2851 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1095 2.9039 -0.6779 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4869 2.6975 -1.2921 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0453 1.1375 -1.9497 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7884 2.7367 -2.4790 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 1 9 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 1 18 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 23 25 1 0 25 26 1 0 20 27 1 0 27 28 1 0 28 29 1 0 29 30 2 0 27 31 1 0 31 32 1 0 32 33 1 1 11 34 1 0 4 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 42 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 57 58 1 0 57 59 1 0 59 60 1 0 59 61 1 0 61 62 1 0 50 63 1 0 63 64 1 0 63 65 1 0 44 66 1 0 66 67 1 0 66 68 1 0 38 2 1 0 68 40 1 0 34 6 1 0 65 46 1 0 15 9 1 0 32 18 1 0 61 52 1 0 32 14 1 0 26 21 1 0 1 69 1 0 1 70 1 0 1 71 1 0 2 72 1 6 4 73 1 6 6 74 1 6 7 75 1 0 7 76 1 0 8 77 1 0 8 78 1 0 10 79 1 0 10 80 1 0 10 81 1 0 11 82 1 1 12 83 1 0 12 84 1 0 13 85 1 0 13 86 1 0 14 87 1 1 15 88 1 6 16 89 1 0 16 90 1 0 17 91 1 0 17 92 1 0 19 93 1 0 19 94 1 0 19 95 1 0 20 96 1 6 22 97 1 0 26 98 1 0 26 99 1 0 27100 1 6 29101 1 0 31102 1 0 31103 1 0 33104 1 0 34105 1 0 34106 1 0 35107 1 0 35108 1 0 36109 1 1 37110 1 0 38111 1 1 40112 1 1 41113 1 0 41114 1 0 42115 1 6 43116 1 0 44117 1 6 46118 1 6 47119 1 0 47120 1 0 48121 1 1 49122 1 0 50123 1 1 52124 1 1 54125 1 1 55126 1 0 55127 1 0 56128 1 0 57129 1 6 58130 1 0 59131 1 1 60132 1 0 61133 1 1 62134 1 0 63135 1 1 64136 1 0 64137 1 0 64138 1 0 66139 1 6 67140 1 0 67141 1 0 67142 1 0 M END

Standard InCHIKey	DVZRMNUVMZDNJY-YFWSQMBUSA-N
Standard InCHI	InChI=1S/C48H74O20/c1-21-42(66-36-15-30(52)43(22(2)62-36)67-37-16-31(53)44(23(3)63-37)68-45-41(57)40(56)39(55)33(18-49)65-45)29(51)14-35(61-21)64-26-8-10-46(4)25(13-26)6-7-28-27(46)9-11-47(5)38(24-12-34(54)59-19-24)32(60-20-50)17-48(28,47)58/h12,20-23,25-33,35-45,49,51-53,55-58H,6-11,13-19H2,1-5H3/t21-,22-,23-,25-,26+,27+,28-,29+,30+,31+,32+,33-,35+,36+,37+,38+,39-,40+,41-,42-,43-,44-,45+,46+,47-,48+/m1/s1
SMILES	C[C@H]1O[C@@H](O[C@H]2CC[C@@]3(C)[C@H](CC[C@@H]4[C@@H]3CC[C@]3(C)[C@@H](C5=CC(=O)OC5)[C@@H](OC=O)C[C@]43O)C2)C[C@H](O)[C@@H]1O[C@H]1C[C@H](O)[C@H](O[C@H]2C[C@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](C)O2)[C@@H](C)O1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	970.48	Volume:	929.651 ? Van der Waals volume.
Dense:	1.044	LogP:	1.557 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.094 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.053 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	51.0
TPSA:	288.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	8.0	Rings:	9.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.074	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.691	Fsp³:	0.917
MCE-18:	172.391 ? 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:	0.713	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.318	Promiscuous compounds:	0.512

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.407	MDCK Permeability:	-5.054
Pgp-inhibitor:	0.125	Pgp-substrate:	0.983
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):	0.001
20% Bioavailability (F20%):	0.046	30% Bioavailability (F30%):	0.433
50% Bioavailability (F50%):	0.964

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.647
Plasma Protein Binding (PPB):	47.593%	Volume Distribution (VD):	-0.519
Fu:	41.581% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.987	BCRP inhibitor:	0.0
BSEP inhibitor:	0.884

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:	0.602	CYP3A4-substrate:	0.409
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.225
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):

-0.212

Half-life (T1/2):

4.583

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.081
Human Hepatotoxicity (H-HT):	0.472	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.927
Maximum Recommended Daily Dose:	0.961	Skin Sensitization:	1.0
Carcinogencity:	0.324	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.596
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.999
Hematotoxicity:	0.99	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.883
A549 Cytotoxicity:	0.988	Hek293 Cytotoxicity:	0.964
BCF:	0.535 ? 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:	3.273 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.774 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.849 ? 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
NPO59360	Digitalis purpurea L.	Genus	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC539423 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	17332
0.1-0.2	28055
0.2-0.3	3794
0.3-0.4	497
0.4-0.5	85
0.5-0.6	59
0.6-0.7	28
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8989	High Similarity	NPC475219
0.7273	Intermediate Similarity	NPC475590
0.7188	Intermediate Similarity	NPC208193
0.7172	Intermediate Similarity	NPC488943
0.7172	Intermediate Similarity	NPC488942
0.7129	Intermediate Similarity	NPC120390
0.7	Intermediate Similarity	NPC488938
0.7	Intermediate Similarity	NPC488937
0.6961	Remote Similarity	NPC74259
0.6837	Remote Similarity	NPC125077
0.6762	Remote Similarity	NPC488945
0.6762	Remote Similarity	NPC488946
0.6701	Remote Similarity	NPC236973
0.6559	Remote Similarity	NPC5311
0.6542	Remote Similarity	NPC488947
0.6458	Remote Similarity	NPC193893
0.6415	Remote Similarity	NPC117445
0.6415	Remote Similarity	NPC308262
0.6392	Remote Similarity	NPC72260
0.63	Remote Similarity	NPC475556
0.63	Remote Similarity	NPC311706
0.6238	Remote Similarity	NPC231518
0.6238	Remote Similarity	NPC488944
0.6176	Remote Similarity	NPC486143
0.6176	Remote Similarity	NPC486142
0.6176	Remote Similarity	NPC486149
0.61	Remote Similarity	NPC30483
0.61	Remote Similarity	NPC470897
0.604	Remote Similarity	NPC292467
0.604	Remote Similarity	NPC40749
0.6019	Remote Similarity	NPC55532
0.6019	Remote Similarity	NPC475419
0.6	Remote Similarity	NPC103534
0.6	Remote Similarity	NPC44899
0.6	Remote Similarity	NPC304260
0.6	Remote Similarity	NPC29639
0.5963	Remote Similarity	NPC474908
0.5946	Remote Similarity	NPC474423
0.5905	Remote Similarity	NPC486146
0.5888	Remote Similarity	NPC479360
0.5888	Remote Similarity	NPC479359
0.5882	Remote Similarity	NPC32177
0.5882	Remote Similarity	NPC469756
0.5882	Remote Similarity	NPC275901
0.5842	Remote Similarity	NPC173555
0.5842	Remote Similarity	NPC5883
0.5833	Remote Similarity	NPC486144
0.5833	Remote Similarity	NPC99620
0.5833	Remote Similarity	NPC486145
0.5833	Remote Similarity	NPC486147
0.5833	Remote Similarity	NPC486148
0.5825	Remote Similarity	NPC188234
0.5743	Remote Similarity	NPC480907
0.5714	Remote Similarity	NPC77299
0.5714	Remote Similarity	NPC480906
0.5686	Remote Similarity	NPC488935
0.5686	Remote Similarity	NPC488936
0.567	Remote Similarity	NPC471633
0.5657	Remote Similarity	NPC480914
0.5619	Remote Similarity	NPC488941
0.5619	Remote Similarity	NPC488940
0.5607	Remote Similarity	NPC329986
0.5607	Remote Similarity	NPC140092
0.5536	Remote Similarity	NPC329675
0.5536	Remote Similarity	NPC486134
0.5536	Remote Similarity	NPC486141
0.5463	Remote Similarity	NPC488939
0.5421	Remote Similarity	NPC486135
0.5421	Remote Similarity	NPC486137
0.5377	Remote Similarity	NPC479353
0.5377	Remote Similarity	NPC240070
0.5377	Remote Similarity	NPC479354
0.537	Remote Similarity	NPC232785
0.537	Remote Similarity	NPC486139
0.5347	Remote Similarity	NPC76572
0.5347	Remote Similarity	NPC193382
0.5234	Remote Similarity	NPC480910
0.5234	Remote Similarity	NPC32793
0.5234	Remote Similarity	NPC116075
0.5234	Remote Similarity	NPC480909
0.5149	Remote Similarity	NPC84987
0.5135	Remote Similarity	NPC486138
0.5135	Remote Similarity	NPC276838
0.5133	Remote Similarity	NPC486136
0.5098	Remote Similarity	NPC469750
0.5098	Remote Similarity	NPC99080
0.5096	Remote Similarity	NPC471353
0.5093	Remote Similarity	NPC608063
0.5089	Remote Similarity	NPC479357
0.5049	Remote Similarity	NPC84949
0.5049	Remote Similarity	NPC480562
0.5049	Remote Similarity	NPC74945
0.5049	Remote Similarity	NPC31354
0.5049	Remote Similarity	NPC69576
0.5045	Remote Similarity	NPC146857

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC539423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6707
0.1-0.2	2359
0.2-0.3	65
0.3-0.4	8
0.4-0.5	3
0.5-0.6	6
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	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6392	Remote Similarity	NPD8294	Phase 4
0.6238	Remote Similarity	NPD8033	Approved
0.5865	Remote Similarity	NPD8377	Phase 4
0.5842	Remote Similarity	NPD8296	Phase 4
0.5758	Remote Similarity	NPD8335	Phase 4
0.57	Remote Similarity	NPD8380	Approved
0.537	Remote Similarity	NPD8378	Pre-clinical
0.537	Remote Similarity	NPD8379	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