NPASS Compound

Natural Product: NPC46665

Natural Product ID	NPC46665
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ilekudinoside A
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL444740
PubChem CID	21635821
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 160168 0 0 0 0 0 0 0 0999 V2000 -13.1553 -2.1725 -2.2671 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.8395 -2.6366 -2.4237 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9098 -1.6257 -1.7905 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5823 -2.0293 -1.9131 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7662 -0.9317 -1.5544 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.5128 -1.3572 -1.1773 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2499 -1.0339 0.1600 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1042 -2.3755 0.9107 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.3237 -3.0280 0.7857 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0608 -3.2143 0.1829 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1016 -2.3675 -0.3968 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8626 -1.3146 0.5742 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9177 -0.3223 0.3352 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0090 0.7431 1.1983 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9415 1.9933 0.6764 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.8181 2.7291 1.0147 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0275 3.3603 2.2231 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7024 3.9669 2.6896 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0078 4.5247 2.0626 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8772 4.2436 0.8576 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2191 2.7527 0.9361 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1647 2.4382 -0.0088 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2252 4.5378 -0.3277 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8130 4.5657 3.1792 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5438 -0.9237 0.3750 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6511 -1.4703 1.2956 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8420 -2.5453 0.5989 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4343 -2.2366 0.3234 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0817 -0.7395 0.3207 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4771 -0.2409 1.6702 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8664 -0.5570 2.1248 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6027 0.7499 2.3145 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8092 -1.1353 3.5656 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0703 1.1883 1.8146 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4563 1.2031 1.8945 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0855 0.5405 0.7213 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4280 -0.7069 0.2496 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9819 -1.1145 -1.0607 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4772 -0.9648 -1.0752 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1996 -0.4285 -0.1203 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5111 0.1024 1.1278 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4504 -0.8951 2.2252 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3332 1.3272 1.4596 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7108 0.9113 1.8974 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4218 -0.0010 0.9568 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6594 -0.3348 -0.2843 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3092 -1.4125 -1.0664 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7950 -2.6075 -0.3002 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6915 -3.5866 -0.0386 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7852 -3.3203 -1.2465 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5888 -2.2182 0.8965 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9167 -1.1962 1.7398 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6761 0.7068 0.5473 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9519 1.8816 0.9786 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6360 0.1909 -0.3037 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8079 0.8757 -0.6619 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9233 1.1696 -2.0109 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0409 2.0290 -2.0997 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0194 2.8672 -3.3452 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0266 2.0056 -4.4484 O 0 0 0 0 0 0 0 0 0 0 0 0 12.3249 1.2639 -1.9230 C 0 0 2 0 0 0 0 0 0 0 0 0 12.0216 -0.0533 -1.2287 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9939 0.1036 -0.1296 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5702 0.7356 0.9699 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5871 -1.0321 -2.0964 O 0 0 0 0 0 0 0 0 0 0 0 0 13.2241 1.9415 -1.0889 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1812 1.6266 -0.3449 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7973 -0.1467 -0.8267 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7165 -0.0630 -2.7810 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1220 0.3940 -3.0854 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.1734 -0.2234 -2.2255 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.5218 0.6199 -1.1443 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4426 0.2349 -4.4449 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7966 0.9486 -2.6679 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.7100 -2.6620 -2.9489 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5864 -2.8870 -3.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7928 -3.5699 -1.7951 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1353 -1.6674 -0.6854 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2678 -0.3777 -0.7314 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1067 -0.5231 0.5684 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8965 -2.2369 1.9760 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6442 -3.4085 1.6524 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5869 -3.8403 -0.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5649 -3.8404 0.9136 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9391 -1.8978 1.5146 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7514 0.1455 -0.6864 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8626 1.8672 -0.4459 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4225 2.6876 2.9977 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8053 5.0510 2.9007 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9114 3.7924 1.9022 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3351 3.4760 3.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4582 5.4827 1.9690 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8187 4.8399 0.9207 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5886 2.6069 1.9745 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9821 2.9895 -0.8234 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4070 5.4452 -0.6581 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7982 3.7041 3.6680 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3317 -2.0770 1.9784 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3661 -2.8028 -0.3636 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8619 -3.5248 1.1649 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1406 -2.6965 -0.6629 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2702 -2.7025 1.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1984 -0.8135 2.3796 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2578 1.2133 3.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6817 0.6005 2.4763 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4595 1.4517 1.4974 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8176 -1.3321 3.9414 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1847 -0.5057 4.2072 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2910 -2.1229 3.4805 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3415 1.8290 0.9700 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4019 1.6883 2.7411 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7292 0.8453 2.8846 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7097 2.3070 1.9097 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7470 -1.5473 0.9487 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5293 -0.6675 -1.9601 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8052 -2.2247 -1.1898 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8766 -1.3654 -2.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1606 -0.6538 3.0739 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6636 -1.9478 1.8638 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4844 -1.0144 2.7483 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5098 1.9028 0.5002 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8802 1.9569 2.2296 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7489 0.5281 2.9556 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2651 1.9042 2.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7895 0.6043 -0.9376 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6810 -1.8135 -1.8848 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2071 -1.0030 -1.6293 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2378 -3.4867 0.9589 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1073 -4.6302 -0.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9304 -3.4581 -0.8366 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4061 -4.0360 -0.7081 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4229 -2.4785 -1.6448 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2209 -3.7087 -2.0955 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6215 -1.9614 0.6083 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6960 -3.1467 1.5340 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7090 -0.7803 2.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1957 -1.6810 2.3804 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8199 1.8754 -0.1313 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9622 2.7079 -1.2016 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8335 3.5944 -3.3524 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0254 3.3901 -3.3948 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6893 2.3378 -5.1043 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8077 1.0627 -2.8784 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9912 -0.4029 -0.7808 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7340 -0.9256 0.1979 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4086 0.2998 1.2161 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6072 -1.0523 -2.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7385 1.2886 -0.5171 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1261 1.9608 -0.5383 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7493 1.3673 -1.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6131 2.5266 0.1919 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5286 0.6731 -0.5573 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1857 0.3063 -1.6238 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4483 -0.8848 -1.3876 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4107 -0.6776 -3.6750 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1404 1.5065 -2.8927 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1178 -0.2565 -2.8470 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9208 0.0111 -0.4514 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3878 -0.0402 -4.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9079 0.5955 -2.9533 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 8 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 17 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 0 19 24 1 0 12 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 30 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 1 1 41 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 48 50 1 0 48 51 1 0 51 52 1 0 45 53 1 6 53 54 2 0 53 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 58 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 62 65 1 0 61 66 1 0 36 67 1 6 29 68 1 6 5 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 70 73 1 0 69 74 1 0 71 3 1 0 13 7 1 0 21 15 1 0 31 26 1 0 41 36 1 0 52 45 1 0 63 56 1 0 37 29 1 0 46 40 1 0 1 75 1 0 2 76 1 0 2 77 1 0 3 78 1 1 5 79 1 1 7 80 1 1 8 81 1 1 9 82 1 0 10 83 1 0 10 84 1 0 12 85 1 1 13 86 1 6 15 87 1 6 17 88 1 1 18 89 1 0 18 90 1 0 18 91 1 0 19 92 1 6 20 93 1 1 21 94 1 1 22 95 1 0 23 96 1 0 24 97 1 0 26 98 1 1 27 99 1 0 27100 1 0 28101 1 0 28102 1 0 30103 1 1 32104 1 0 32105 1 0 32106 1 0 33107 1 0 33108 1 0 33109 1 0 34110 1 0 34111 1 0 35112 1 0 35113 1 0 37114 1 1 38115 1 0 38116 1 0 39117 1 0 42118 1 0 42119 1 0 42120 1 0 43121 1 0 43122 1 0 44123 1 0 44124 1 0 46125 1 6 47126 1 0 47127 1 0 49128 1 0 49129 1 0 49130 1 0 50131 1 0 50132 1 0 50133 1 0 51134 1 0 51135 1 0 52136 1 0 52137 1 0 56138 1 1 58139 1 1 59140 1 0 59141 1 0 60142 1 0 61143 1 6 62144 1 1 63145 1 1 64146 1 0 65147 1 0 66148 1 0 67149 1 0 67150 1 0 67151 1 0 68152 1 0 68153 1 0 68154 1 0 69155 1 6 70156 1 1 71157 1 6 72158 1 0 73159 1 0 74160 1 0 M END

Standard InCHIKey	ULSOTXJNUTYKRK-DFRCHCFDSA-N
Standard InCHI	InChI=1S/C53H86O21/c1-23-32(57)35(60)38(63)43(68-23)73-42-41(72-44-39(64)36(61)33(58)27(20-54)69-44)26(56)22-67-46(42)71-31-12-13-50(6)29(49(31,4)5)11-14-52(8)30(50)10-9-24-25-19-48(2,3)15-17-53(25,18-16-51(24,52)7)47(66)74-45-40(65)37(62)34(59)28(21-55)70-45/h9,23,25-46,54-65H,10-22H2,1-8H3/t23-,25-,26-,27+,28+,29-,30+,31-,32-,33+,34+,35+,36-,37-,38+,39+,40+,41-,42+,43-,44-,45-,46-,50-,51+,52+,53-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O)CO[C@H]([C@@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)CC2)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1058.57	Volume:	1027.557 ? Van der Waals volume.
Dense:	1.03	LogP:	1.271 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.074 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.096 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	51.0
TPSA:	333.67 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	12.0	Rings:	9.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.075	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.69	Fsp³:	0.943
MCE-18:	194.369 ? 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:	0.906	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.218	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.518	MDCK Permeability:	-5.104
Pgp-inhibitor:	0.0	Pgp-substrate:	0.02
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):	0.861
20% Bioavailability (F20%):	0.307	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.522	MRP1:	0.001
Plasma Protein Binding (PPB):	66.959%	Volume Distribution (VD):	-0.297
Fu:	21.037% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.009
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:	0.013
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.999
HLM stability:	0.242 ? 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):

-0.512

Half-life (T1/2):

4.545

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.009
Human Hepatotoxicity (H-HT):	0.756	Drug-induced Liver Injury (DILI):	0.964
AMES Toxicity:	0.961	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.036	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.622	Drug-induced Nephrotoxicity:	0.993
Genotoxicity:	0.221	RPMI-8226 Immunitoxicity:	0.288
A549 Cytotoxicity:	0.884	Hek293 Cytotoxicity:	0.591
BCF:	1.983 ? 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:	4.004 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.477 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.728 ? 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
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10425145]
NPO33035	ilex kudincha	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10479318]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12506	Hedyotis nudicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12506	Hedyotis nudicaulis	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12506	Hedyotis nudicaulis	Species	Rubiaceae	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
Inhibition	2

Activity Type	# Activity
Individual protein	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1214	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	25.4	%	PMID[10479318]
NPT1214	Individual protein	Acyl coenzyme A:cholesterol acyltransferase 1	Homo sapiens	Inhibition	=	31.7	%	PMID[10479318]

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 NPC46665 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	22647
0.1-0.2	22844
0.2-0.3	2960
0.3-0.4	784
0.4-0.5	372
0.5-0.6	88
0.6-0.7	79
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8404	Intermediate Similarity	NPC161674
0.8316	Intermediate Similarity	NPC112352
0.8247	Intermediate Similarity	NPC68175
0.7925	Intermediate Similarity	NPC100639
0.7778	Intermediate Similarity	NPC10607
0.7748	Intermediate Similarity	NPC481081
0.77	Intermediate Similarity	NPC475591
0.77	Intermediate Similarity	NPC236870
0.7653	Intermediate Similarity	NPC263756
0.7526	Intermediate Similarity	NPC475516
0.75	Intermediate Similarity	NPC80986
0.75	Intermediate Similarity	NPC135904
0.7429	Intermediate Similarity	NPC36831
0.7429	Intermediate Similarity	NPC187290
0.7353	Intermediate Similarity	NPC63159
0.7347	Intermediate Similarity	NPC235405
0.732	Intermediate Similarity	NPC48499
0.7292	Intermediate Similarity	NPC214484
0.7273	Intermediate Similarity	NPC249848
0.7273	Intermediate Similarity	NPC107966
0.7222	Intermediate Similarity	NPC60557
0.7222	Intermediate Similarity	NPC67857
0.7129	Intermediate Similarity	NPC469946
0.7117	Intermediate Similarity	NPC475160
0.7117	Intermediate Similarity	NPC473714
0.7103	Intermediate Similarity	NPC481078
0.7064	Intermediate Similarity	NPC268184
0.7059	Intermediate Similarity	NPC192791
0.703	Intermediate Similarity	NPC39211
0.7027	Intermediate Similarity	NPC155410
0.7019	Intermediate Similarity	NPC235438
0.7	Intermediate Similarity	NPC79643
0.699	Remote Similarity	NPC30735
0.699	Remote Similarity	NPC117714
0.6983	Remote Similarity	NPC305981
0.6981	Remote Similarity	NPC114484
0.6952	Remote Similarity	NPC222580
0.693	Remote Similarity	NPC476068
0.693	Remote Similarity	NPC57484
0.6923	Remote Similarity	NPC261506
0.6923	Remote Similarity	NPC251768
0.6923	Remote Similarity	NPC4328
0.6916	Remote Similarity	NPC481079
0.6852	Remote Similarity	NPC295823
0.6852	Remote Similarity	NPC174720
0.6852	Remote Similarity	NPC475467
0.6827	Remote Similarity	NPC160415
0.681	Remote Similarity	NPC41061
0.681	Remote Similarity	NPC227551
0.681	Remote Similarity	NPC258617
0.6792	Remote Similarity	NPC297263
0.6762	Remote Similarity	NPC480475
0.6757	Remote Similarity	NPC475287
0.6752	Remote Similarity	NPC43550
0.6731	Remote Similarity	NPC223301
0.6731	Remote Similarity	NPC171544
0.6726	Remote Similarity	NPC123199
0.6699	Remote Similarity	NPC157868
0.6667	Remote Similarity	NPC281148
0.6635	Remote Similarity	NPC213674
0.6609	Remote Similarity	NPC488560
0.6607	Remote Similarity	NPC76972
0.6607	Remote Similarity	NPC469782
0.6607	Remote Similarity	NPC204414
0.6606	Remote Similarity	NPC301449
0.6606	Remote Similarity	NPC601290
0.6604	Remote Similarity	NPC40775
0.6604	Remote Similarity	NPC159309
0.6604	Remote Similarity	NPC86222
0.66	Remote Similarity	NPC90856
0.6596	Remote Similarity	NPC167383
0.6555	Remote Similarity	NPC236638
0.6555	Remote Similarity	NPC294453
0.6514	Remote Similarity	NPC104372
0.6486	Remote Similarity	NPC31838
0.6475	Remote Similarity	NPC250247
0.6471	Remote Similarity	NPC293330
0.6458	Remote Similarity	NPC237503
0.6449	Remote Similarity	NPC164389
0.641	Remote Similarity	NPC481080
0.6396	Remote Similarity	NPC96641
0.6396	Remote Similarity	NPC163183
0.6364	Remote Similarity	NPC298034
0.6364	Remote Similarity	NPC71065
0.633	Remote Similarity	NPC475504
0.625	Remote Similarity	NPC480473
0.625	Remote Similarity	NPC241909
0.625	Remote Similarity	NPC480474
0.6239	Remote Similarity	NPC148417
0.6239	Remote Similarity	NPC470218
0.6238	Remote Similarity	NPC209894
0.6226	Remote Similarity	NPC295371
0.6207	Remote Similarity	NPC165204
0.6204	Remote Similarity	NPC104071
0.6198	Remote Similarity	NPC65105
0.6147	Remote Similarity	NPC102439
0.6139	Remote Similarity	NPC128925
0.6132	Remote Similarity	NPC58448
0.6124	Remote Similarity	NPC475368
0.6102	Remote Similarity	NPC471550
0.6098	Remote Similarity	NPC302543
0.6075	Remote Similarity	NPC473884
0.6058	Remote Similarity	NPC1046
0.6058	Remote Similarity	NPC29069
0.6055	Remote Similarity	NPC30289
0.6048	Remote Similarity	NPC70809
0.6019	Remote Similarity	NPC76497
0.6016	Remote Similarity	NPC202828
0.6016	Remote Similarity	NPC119592
0.6	Remote Similarity	NPC224381
0.6	Remote Similarity	NPC2370
0.5983	Remote Similarity	NPC192600
0.5966	Remote Similarity	NPC283417
0.5966	Remote Similarity	NPC200049
0.5963	Remote Similarity	NPC242840
0.5962	Remote Similarity	NPC204458
0.5938	Remote Similarity	NPC480422
0.5909	Remote Similarity	NPC309714
0.5906	Remote Similarity	NPC480417
0.5873	Remote Similarity	NPC220160
0.5856	Remote Similarity	NPC44716
0.5854	Remote Similarity	NPC475514
0.5833	Remote Similarity	NPC473373
0.5833	Remote Similarity	NPC150400
0.582	Remote Similarity	NPC21691
0.5798	Remote Similarity	NPC475899
0.5785	Remote Similarity	NPC47995
0.5776	Remote Similarity	NPC104137
0.5776	Remote Similarity	NPC26626
0.5772	Remote Similarity	NPC286457
0.576	Remote Similarity	NPC477463
0.5755	Remote Similarity	NPC78046
0.5743	Remote Similarity	NPC199457
0.5714	Remote Similarity	NPC123522
0.5702	Remote Similarity	NPC64715
0.5691	Remote Similarity	NPC484061
0.5691	Remote Similarity	NPC484062
0.5686	Remote Similarity	NPC68419
0.5645	Remote Similarity	NPC110633
0.561	Remote Similarity	NPC85154
0.56	Remote Similarity	NPC470876
0.5588	Remote Similarity	NPC306746
0.5575	Remote Similarity	NPC173859
0.5575	Remote Similarity	NPC473459
0.5575	Remote Similarity	NPC148603
0.5556	Remote Similarity	NPC475208
0.5545	Remote Similarity	NPC173583
0.5545	Remote Similarity	NPC109079
0.5536	Remote Similarity	NPC75417
0.5534	Remote Similarity	NPC604133
0.5524	Remote Similarity	NPC256798
0.5512	Remote Similarity	NPC136768
0.5484	Remote Similarity	NPC487505
0.5462	Remote Similarity	NPC470915
0.5455	Remote Similarity	NPC108748
0.5446	Remote Similarity	NPC22956
0.5442	Remote Similarity	NPC469778
0.5431	Remote Similarity	NPC79718
0.5431	Remote Similarity	NPC302887
0.5424	Remote Similarity	NPC160452
0.5421	Remote Similarity	NPC47063
0.5405	Remote Similarity	NPC127056
0.54	Remote Similarity	NPC191763
0.5398	Remote Similarity	NPC256133
0.5379	Remote Similarity	NPC469776
0.5374	Remote Similarity	NPC32723
0.537	Remote Similarity	NPC189884
0.537	Remote Similarity	NPC138334
0.536	Remote Similarity	NPC4749
0.5345	Remote Similarity	NPC470478
0.5345	Remote Similarity	NPC257468
0.5338	Remote Similarity	NPC481323
0.5333	Remote Similarity	NPC62725
0.5315	Remote Similarity	NPC25605
0.5315	Remote Similarity	NPC139894
0.5315	Remote Similarity	NPC56713
0.5312	Remote Similarity	NPC484059
0.5312	Remote Similarity	NPC484060
0.531	Remote Similarity	NPC473343
0.5294	Remote Similarity	NPC187618
0.5294	Remote Similarity	NPC481030
0.5294	Remote Similarity	NPC295941
0.5276	Remote Similarity	NPC473452
0.5267	Remote Similarity	NPC135334
0.5243	Remote Similarity	NPC46388
0.5243	Remote Similarity	NPC605954
0.5232	Remote Similarity	NPC481324
0.5229	Remote Similarity	NPC238935
0.5229	Remote Similarity	NPC269095
0.5221	Remote Similarity	NPC470512
0.5217	Remote Similarity	NPC480947
0.5217	Remote Similarity	NPC605226
0.5214	Remote Similarity	NPC123796
0.5214	Remote Similarity	NPC609763
0.521	Remote Similarity	NPC324875
0.521	Remote Similarity	NPC292677
0.5207	Remote Similarity	NPC11242
0.5192	Remote Similarity	NPC116794
0.5175	Remote Similarity	NPC80843

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC46665 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7427
0.1-0.2	1662
0.2-0.3	53
0.3-0.4	8
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data