NPASS Compound

Natural Product: NPC470748

Natural Product ID	NPC470748
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Acanthifolioside J
IUPAC Name	[(3S,8R,9S,10R,13R,14S,15S,16R,17R)-3-[(2S,3S,4R,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-17-[(2R,4S,5R)-5-ethyl-4-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-15-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl] acetate
Synonyms	Acanthifolioside J
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2208393
PubChem CID	71463285
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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 149155 0 0 0 0 0 0 0 0999 V2000 -7.0469 5.0406 -0.9135 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0139 4.5146 0.4798 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8379 3.3413 0.8123 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3130 3.5312 0.4807 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0634 2.2897 0.8693 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8368 4.6859 1.2940 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3294 1.9728 0.8370 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7476 1.1390 -0.1423 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5279 1.1760 -0.9381 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3587 2.3100 -1.8537 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2730 0.7056 -0.2343 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3411 -0.6953 0.2743 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9780 -1.3686 -0.0313 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1405 -0.1727 -0.1350 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0192 0.7221 -1.0301 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3270 2.0561 -1.0755 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0156 2.1105 -0.3097 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1302 1.0616 -0.8492 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7381 -0.2848 -0.4412 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2064 -1.2380 -1.4438 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2910 -1.2927 -1.1835 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9238 -0.2450 -0.7252 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2886 1.0850 -0.4081 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0634 2.1794 -1.1101 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0825 1.6164 -2.0714 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1026 0.7340 -1.3473 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4012 -0.3045 -0.5159 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9933 1.4998 -0.6313 O 0 0 0 0 0 0 0 0 0 0 0 0 6.2952 1.4914 -1.1472 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3484 1.0923 -0.1819 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6858 2.3532 0.6294 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4748 3.2252 -0.3285 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7374 3.2788 -1.6349 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4696 2.7949 -1.6313 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5840 2.8111 -2.8167 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9382 3.2504 -3.9965 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6966 4.4984 0.2303 O 0 0 0 0 0 0 0 0 0 0 0 0 6.5276 3.0456 0.9562 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0844 0.0310 0.6433 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0700 -0.9495 0.5994 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4989 -2.3069 0.4343 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3133 -3.4087 1.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4380 -3.0682 1.8961 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8737 -1.6563 1.8012 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7767 -0.8160 1.8086 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8460 -1.3750 0.6753 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5068 -3.9467 1.6304 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4658 -4.2873 1.7405 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3752 -2.5270 -0.9604 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4248 1.2804 1.0696 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1123 0.1537 -2.4139 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7009 -2.2728 0.9817 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6968 -3.5949 0.6054 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4603 -4.3724 0.9491 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9163 -5.7733 1.3623 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9344 -6.2901 0.3425 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1526 -5.4058 0.4439 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8286 -4.2647 1.1341 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6757 -5.0057 -0.9339 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2915 -7.5922 0.5927 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5812 -5.6628 2.5787 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6389 -4.5753 -0.1500 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6419 -0.8386 1.6296 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5939 -1.6483 2.1418 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2694 -2.3431 1.3647 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9087 -1.7819 3.5905 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5471 1.9351 2.0759 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0335 5.3909 -1.1853 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3801 4.3507 -1.6940 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6544 6.0104 -0.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9412 4.2167 0.7171 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1504 5.4187 1.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9772 3.5612 2.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4642 3.8061 -0.5796 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9593 2.0550 1.9464 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1879 2.4611 0.7640 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8973 1.4252 0.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1792 4.9068 2.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8342 4.4425 1.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0347 5.5883 0.6817 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2280 1.3539 1.2675 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5855 1.0238 -0.9830 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8310 0.0365 0.2274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6727 0.2932 -1.6678 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0423 3.2499 -1.4399 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6220 2.1000 -2.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2868 2.4462 -2.4556 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0782 1.3466 0.6759 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0660 -1.2855 -0.2978 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0699 -1.9373 -0.9644 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2265 0.3649 0.8657 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0919 2.4017 -2.1025 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9750 2.7908 -0.5110 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5636 3.1089 -0.5963 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2067 2.0967 0.7704 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1774 1.1051 -1.9605 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2080 -0.5435 0.5329 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6173 -2.2366 -1.4570 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1741 -0.7834 -2.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7842 -2.2177 -1.3932 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3666 2.8177 -1.6822 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5756 2.8270 -0.3697 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6304 1.0631 -2.8892 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6505 2.4686 -2.4907 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6491 0.2251 -2.1614 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6749 -0.1184 0.5434 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7269 -1.3378 -0.7405 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2823 0.7712 -2.0046 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3266 0.8514 -0.6892 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2179 2.1065 1.5459 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4923 2.7607 -0.4292 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6245 4.4000 -1.8454 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5658 3.3553 -2.8198 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7997 1.7459 -2.8185 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0992 2.7453 -4.1520 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8469 5.0205 0.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5461 3.4211 1.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8073 -0.6347 -0.1777 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4563 -2.3873 0.8086 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6747 -4.0930 0.1672 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1720 -3.2557 2.9705 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4363 -1.4206 2.7576 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8817 -1.6169 1.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6938 -1.9851 -0.2156 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7972 -0.3104 0.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3031 -3.5662 2.0750 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0601 -4.8235 2.3598 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6277 -3.1152 -1.1868 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0258 0.4720 1.5687 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4354 1.2390 1.6039 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8542 2.2699 1.3425 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6425 0.8392 -3.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1101 -0.2030 -2.7196 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4983 -0.7901 -2.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8600 -3.6476 -0.4879 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8892 -3.9860 1.8033 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0657 -6.4596 1.4929 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4610 -6.1605 -0.6586 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9820 -5.9760 0.9214 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9222 -5.1149 -1.7181 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9668 -3.9144 -0.9206 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6223 -5.5347 -1.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6673 -8.0613 1.2137 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2637 -6.3878 2.5984 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2244 -4.0828 -0.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8921 -2.1959 3.7890 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1298 -2.4712 4.0098 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6993 -0.8063 4.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6032 1.0618 2.4832 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 4 6 1 0 3 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 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 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 32 37 1 0 31 38 1 0 30 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 44 46 1 0 43 47 1 0 42 48 1 0 41 49 1 0 23 50 1 0 15 51 1 0 13 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 57 59 1 0 56 60 1 0 55 61 1 0 54 62 1 0 12 63 1 0 63 64 1 0 64 65 2 0 64 66 1 0 7 67 1 0 15 11 1 0 19 14 1 0 23 18 1 0 27 22 1 0 34 29 1 0 45 40 1 0 58 53 1 0 1 68 1 0 1 69 1 0 1 70 1 0 2 71 1 0 2 72 1 0 3 73 1 0 4 74 1 0 5 75 1 0 5 76 1 0 5 77 1 0 6 78 1 0 6 79 1 0 6 80 1 0 7 81 1 0 8 82 1 0 8 83 1 0 9 84 1 0 10 85 1 0 10 86 1 0 10 87 1 0 11 88 1 0 12 89 1 0 13 90 1 0 14 91 1 0 16 92 1 0 16 93 1 0 17 94 1 0 17 95 1 0 18 96 1 0 19 97 1 0 20 98 1 0 20 99 1 0 21100 1 0 24101 1 0 24102 1 0 25103 1 0 25104 1 0 26105 1 0 27106 1 0 27107 1 0 29108 1 0 30109 1 0 31110 1 0 32111 1 0 33112 1 0 35113 1 0 35114 1 0 36115 1 0 37116 1 0 38117 1 0 40118 1 0 41119 1 0 42120 1 0 43121 1 0 44122 1 0 46123 1 0 46124 1 0 46125 1 0 47126 1 0 48127 1 0 49128 1 0 50129 1 0 50130 1 0 50131 1 0 51132 1 0 51133 1 0 51134 1 0 53135 1 0 54136 1 0 55137 1 0 56138 1 0 57139 1 0 59140 1 0 59141 1 0 59142 1 0 60143 1 0 61144 1 0 62145 1 0 66146 1 0 66147 1 0 66148 1 0 67149 1 0 M END

Standard InCHIKey	ACNZKOPPFHPPKV-BXARVIKJSA-N
Standard InCHI	InChI=1S/C49H82O18/c1-10-27(20(2)3)30(52)17-21(4)32-42(63-24(7)51)43(66-45-40(59)37(56)34(53)22(5)61-45)33-28-12-11-25-18-26(13-15-48(25,8)29(28)14-16-49(32,33)9)64-47-44(39(58)36(55)31(19-50)65-47)67-46-41(60)38(57)35(54)23(6)62-46/h11,20-23,26-47,50,52-60H,10,12-19H2,1-9H3/t21-,22+,23+,26+,27-,28-,29+,30+,31+,32+,33-,34+,35+,36+,37-,38-,39-,40-,41-,42-,43+,44+,45+,46+,47+,48+,49-/m1/s1
SMILES	CCC(C(C)C)C(CC(C)C1C(C(C2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)C)O)O)O)C)C)OC7C(C(C(C(O7)C)O)O)O)OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	958.55	Volume:	949.116 ? Van der Waals volume.
Dense:	1.01	LogP:	1.953 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.188 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.277 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	15.0	Rigid Bonds:	39.0
TPSA:	283.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	7.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.086	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.561	Fsp³:	0.939
MCE-18:	144.737 ? 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:	0.105	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.093 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.285	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.863	MDCK Permeability:	-5.176
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
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):	0.993
20% Bioavailability (F20%):	0.348	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	1.0
Plasma Protein Binding (PPB):	46.588%	Volume Distribution (VD):	-0.482
Fu:	36.283% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.021	BCRP inhibitor:	0.003
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.974	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.353	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.996	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.616
HLM stability:	0.002 ? 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):

0.104

Half-life (T1/2):

3.924

ADMET: Toxicity

hERG Blockers:	0.062	hERG Blockers (10um):	0.636
Human Hepatotoxicity (H-HT):	0.638	Drug-induced Liver Injury (DILI):	0.342
AMES Toxicity:	0.085	Rat Oral Acute Toxicity:	0.119
Maximum Recommended Daily Dose:	0.404	Skin Sensitization:	0.0
Carcinogencity:	0.005	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.433	Ototoxicity:	1.0
Hematotoxicity:	0.01	Drug-induced Nephrotoxicity:	0.033
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.115
A549 Cytotoxicity:	0.066	Hek293 Cytotoxicity:	0.856
BCF:	1.09 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	4.007 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.133 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.52 ? 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
NPO20847	Pandaros acanthifolium	Species	Clathriidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20614907]
NPO20847	Pandaros acanthifolium	Species	Clathriidae	Eukaryota	n.a.	Caribbean	n.a.	PMID[23245401]
NPO20847	Pandaros acanthifolium	Species	Clathriidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20847	Pandaros acanthifolium	Species	Clathriidae	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
FC	1

Activity Type	# Activity
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	FC	=	1.52	n.a.	PMID[23245401]

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 NPC470748 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	20609
0.1-0.2	23840
0.2-0.3	4070
0.3-0.4	1168
0.4-0.5	116
0.5-0.6	44
0.6-0.7	8
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
0.6346	Remote Similarity	NPC98696
0.6346	Remote Similarity	NPC486388
0.6327	Remote Similarity	NPC210157
0.6275	Remote Similarity	NPC306991
0.6154	Remote Similarity	NPC113044
0.6154	Remote Similarity	NPC283829
0.6154	Remote Similarity	NPC161676
0.6	Remote Similarity	NPC305423
0.5849	Remote Similarity	NPC600116
0.5818	Remote Similarity	NPC475182
0.5644	Remote Similarity	NPC272015
0.5596	Remote Similarity	NPC40440
0.5532	Remote Similarity	NPC22140
0.5532	Remote Similarity	NPC243728
0.5514	Remote Similarity	NPC94272
0.5487	Remote Similarity	NPC73243
0.5487	Remote Similarity	NPC244086
0.5487	Remote Similarity	NPC84956
0.5478	Remote Similarity	NPC13193
0.547	Remote Similarity	NPC23808
0.547	Remote Similarity	NPC87998
0.5455	Remote Similarity	NPC197231
0.5446	Remote Similarity	NPC165439
0.5391	Remote Similarity	NPC247037
0.5368	Remote Similarity	NPC158088
0.5364	Remote Similarity	NPC19888
0.5351	Remote Similarity	NPC102016
0.5351	Remote Similarity	NPC95051
0.5347	Remote Similarity	NPC486114
0.5327	Remote Similarity	NPC600456
0.5299	Remote Similarity	NPC194207
0.5299	Remote Similarity	NPC22779
0.5278	Remote Similarity	NPC295980
0.5263	Remote Similarity	NPC480555
0.5263	Remote Similarity	NPC150372
0.5258	Remote Similarity	NPC282669
0.5254	Remote Similarity	NPC249265
0.525	Remote Similarity	NPC308140
0.5221	Remote Similarity	NPC477809
0.5133	Remote Similarity	NPC470433
0.5133	Remote Similarity	NPC46190
0.5133	Remote Similarity	NPC171073
0.5128	Remote Similarity	NPC269297
0.5128	Remote Similarity	NPC222202
0.5126	Remote Similarity	NPC218571
0.5126	Remote Similarity	NPC487615
0.5085	Remote Similarity	NPC309278
0.5083	Remote Similarity	NPC486383
0.5082	Remote Similarity	NPC232054
0.5045	Remote Similarity	NPC141433
0.5043	Remote Similarity	NPC300557
0.5041	Remote Similarity	NPC480553

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470748 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7125
0.1-0.2	1910
0.2-0.3	99
0.3-0.4	14
0.4-0.5	2
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