NPASS Compound

Natural Product: NPC473459

Natural Product ID	NPC473459
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gypsogenin 28-O-Alpha-D-Galactopyranosyl-(1->6)-Beta-D-Glucopyranosyl-(1->6)-[Beta-D-Glucopyranosyl-(1->3)]-Beta-D-Glucopyranosyl Ester
IUPAC Name	[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-[[(2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-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	CHEMBL438206
PubChem CID	44451423
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 164172 0 0 0 0 0 0 0 0999 V2000 3.5523 7.5278 -2.7961 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9247 8.1100 -1.6903 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2411 7.2791 -0.4645 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7481 6.0011 -0.7046 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3532 5.3579 0.4553 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0563 4.0406 0.1111 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8209 3.1314 0.8318 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9310 2.1757 1.5790 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7323 1.4053 2.4108 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2197 1.2385 0.6254 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7086 1.4106 -0.6707 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1170 1.1511 -0.5656 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7371 2.4208 -0.1521 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9781 2.2742 0.4852 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5804 0.4614 -1.7912 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8253 0.0768 -1.9997 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8826 0.9098 -2.1729 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8924 0.7787 -1.2396 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6517 -0.3527 -1.3099 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1662 -1.4623 -0.3991 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0025 -2.5272 -0.5663 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7109 -3.6371 0.1988 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7110 -3.9041 1.0884 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7925 -4.5917 0.5260 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9878 -4.6313 1.4471 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4432 -3.3715 1.7624 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3565 -5.9750 0.0800 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8198 -6.0649 0.1688 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3275 -4.8422 -0.5723 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0248 -4.8382 -1.8051 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5433 -5.9748 1.5426 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9734 -6.9202 0.8644 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8597 -0.9083 -2.6713 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8553 0.2990 -3.6224 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4363 0.8050 -3.5999 C 0 0 2 0 0 0 0 0 0 0 0 0 6.3706 1.9857 -4.2952 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1852 -0.1707 -4.8821 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1557 -1.4365 -2.7700 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1606 1.5042 0.7515 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0963 0.5817 1.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7230 -0.5798 1.3704 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5850 0.8780 1.2698 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9683 1.3648 -0.1076 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9958 0.6624 -0.8972 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1165 0.1022 -0.0379 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2927 -0.8562 0.7361 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3629 -2.1311 0.5142 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2464 -2.7958 -0.5188 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0989 -1.8688 -1.2806 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2746 -0.4889 -0.7683 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4680 0.4921 -1.9610 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5268 -0.2889 0.0615 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6155 -1.2956 -0.0288 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1349 -2.6967 -0.3380 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3835 -2.6084 -1.6128 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1095 -1.9428 -2.7578 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0881 -3.9841 -2.1586 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3055 -4.8081 -2.3385 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4059 -4.6277 -1.3635 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1327 -3.7586 -0.1883 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.4879 -3.1656 0.2375 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7834 -4.6633 0.9762 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7862 -4.4537 1.6399 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6321 -4.2634 -1.9856 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2708 -0.3485 1.7392 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7690 -0.4314 3.1361 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6782 0.7142 4.0294 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4553 2.0296 3.3811 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5470 2.0402 2.2338 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5061 0.4968 5.0049 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9068 0.7640 4.9377 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6897 1.2422 0.7673 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0763 6.0018 0.9414 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3577 7.4450 1.1993 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7357 7.8733 0.8069 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6560 7.7035 1.8668 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3689 8.2549 0.6065 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6012 5.4089 2.1048 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7046 8.1911 -3.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8342 8.1096 -1.9117 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3140 9.1357 -1.5980 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3503 7.1997 -0.4001 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1386 5.4301 1.2330 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4663 3.7232 1.5071 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2217 2.7320 2.2103 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9329 1.9426 3.2149 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4190 0.1875 0.8939 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1681 0.3628 0.2595 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8586 3.1069 -1.0035 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5851 3.0003 0.1781 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1270 1.0496 -2.6578 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9328 -0.4926 -1.8498 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5396 1.9583 -2.1164 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6725 -0.0742 -0.9056 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2082 -1.1371 0.6716 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1144 -1.6566 -0.6862 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8013 -3.3466 0.8072 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0887 -4.0302 -0.3767 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8062 -5.2118 2.3711 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7984 -5.1438 0.9007 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3964 -3.2150 1.6018 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6030 -6.0848 -0.9887 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5172 -7.0128 -0.2769 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2334 -4.9336 -0.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3485 -4.6517 -2.4997 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5808 -6.0363 1.7302 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3427 -7.6204 0.2440 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1073 -1.6528 -2.9724 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5621 1.0280 -3.2242 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8247 0.0352 -4.1115 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9360 2.7022 -3.9145 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9893 0.3055 -5.1908 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8225 -0.7529 -3.0045 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1714 2.4831 -0.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0708 1.4229 -0.8115 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4752 -0.2096 -1.3999 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2886 1.3030 -1.7154 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7144 -2.7774 1.1422 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5708 -3.4001 -1.2219 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7221 -3.6234 0.0366 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6067 -1.7425 -2.3025 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2515 1.5479 -1.6085 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7661 0.3166 -2.7633 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5375 0.5938 -2.2336 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2834 -0.1324 1.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0825 0.6630 -0.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0838 -1.3988 1.0040 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5086 -0.9922 -0.6235 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4046 -2.8067 0.5273 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2859 -1.4689 -3.3759 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9255 -1.2901 -2.5087 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5441 -2.6706 -3.4823 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3339 -4.5486 -1.6372 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6555 -3.8109 -3.1921 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7602 -4.6738 -3.3676 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9578 -5.8887 -2.4077 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6714 -5.6671 -0.9854 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1789 -4.0627 0.2168 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8943 -2.4685 -0.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4881 -2.8417 1.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3964 -5.5099 1.2520 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5930 -3.3357 -2.3025 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4407 -1.1567 1.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3659 -1.3319 3.7121 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8690 -0.7226 3.0541 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4365 2.4606 3.0937 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0647 2.7515 4.1486 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5190 2.2928 2.6152 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7988 2.9650 1.6284 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6682 1.1080 5.8950 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6083 0.8391 4.4168 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3580 -0.5730 5.1849 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7862 1.1335 4.3525 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0803 -0.2507 5.3460 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6378 1.4739 5.7535 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9891 2.1284 0.7768 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6058 1.6893 0.3898 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8390 1.0233 1.8381 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2791 5.8453 0.1710 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2680 7.6605 2.3029 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6998 8.9943 0.6659 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1163 7.4915 2.6696 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0932 7.8623 -0.2813 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3798 5.4252 2.1701 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 12 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 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 27 32 1 0 19 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 33 38 1 0 10 39 1 0 39 40 1 0 40 41 2 0 42 40 1 6 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 6 50 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 6 55 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 1 60 62 1 0 62 63 2 0 59 64 1 0 46 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 67 70 1 0 67 71 1 0 45 72 1 1 5 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 74 77 1 0 73 78 1 0 75 3 1 0 13 7 1 0 35 17 1 0 69 42 1 0 29 22 1 0 65 42 1 0 50 45 1 0 60 54 1 0 55 49 1 0 1 79 1 0 2 80 1 0 2 81 1 0 3 82 1 1 5 83 1 1 7 84 1 1 8 85 1 1 9 86 1 0 10 87 1 1 12 88 1 1 13 89 1 6 14 90 1 0 15 91 1 0 15 92 1 0 17 93 1 6 19 94 1 1 20 95 1 0 20 96 1 0 22 97 1 1 24 98 1 6 25 99 1 0 25100 1 0 26101 1 0 27102 1 6 28103 1 6 29104 1 6 30105 1 0 31106 1 0 32107 1 0 33108 1 6 34109 1 1 35110 1 6 36111 1 0 37112 1 0 38113 1 0 43114 1 0 43115 1 0 44116 1 0 44117 1 0 47118 1 0 48119 1 0 48120 1 0 49121 1 0 51122 1 0 51123 1 0 51124 1 0 52125 1 0 52126 1 0 53127 1 0 53128 1 0 54129 1 1 56130 1 0 56131 1 0 56132 1 0 57133 1 0 57134 1 0 58135 1 0 58136 1 0 59137 1 1 61138 1 0 61139 1 0 61140 1 0 62141 1 0 64142 1 0 65143 1 1 66144 1 0 66145 1 0 68146 1 0 68147 1 0 69148 1 0 69149 1 0 70150 1 0 70151 1 0 70152 1 0 71153 1 0 71154 1 0 71155 1 0 72156 1 0 72157 1 0 72158 1 0 73159 1 6 74160 1 1 75161 1 6 76162 1 0 77163 1 0 78164 1 0 M END

Standard InCHIKey	JLSIUEOHGXDDEP-AXSBMVNJSA-N
Standard InCHI	InChI=1S/C54H86O24/c1-49(2)13-15-54(16-14-52(5)23(24(54)17-49)7-8-30-50(3)11-10-31(58)51(4,22-57)29(50)9-12-53(30,52)6)48(70)78-47-42(69)43(77-46-41(68)37(64)33(60)26(19-56)74-46)35(62)28(76-47)21-72-45-40(67)38(65)34(61)27(75-45)20-71-44-39(66)36(63)32(59)25(18-55)73-44/h7,22,24-47,55-56,58-69H,8-21H2,1-6H3/t24-,25-,26-,27-,28-,29+,30?,31-,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,42-,43+,44+,45-,46+,47+,50-,51-,52+,53+,54-/m0/s1
SMILES	OC[C@@H]1O[C@H](O[C@H]2[C@H](O)[C@H](O[C@H]([C@@H]2O)CO[C@H]2O[C@@H](CO[C@@H]3O[C@@H](CO)[C@H]([C@H]([C@@H]3O)O)O)[C@@H]([C@H]([C@@H]2O)O)O)OC(=O)[C@]23CC[C@@]4(C(=CCC5[C@@]4(C)CC[C@@H]4[C@]5(C)CC[C@@H]([C@@]4(C)C=O)O)[C@@H]3CC(CC2)(C)C)C)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[16880670]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[17409564]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	roots	n.a.	n.a.	PMID[18194870]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	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
IC50	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	15200.0	nM	PMID[23316950]

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 NPC473459 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	22672
0.1-0.2	22525
0.2-0.3	3412
0.3-0.4	861
0.4-0.5	238
0.5-0.6	97
0.6-0.7	46
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
0.7766	Intermediate Similarity	NPC29069
0.7451	Intermediate Similarity	NPC609763
0.732	Intermediate Similarity	NPC48499
0.7	Intermediate Similarity	NPC79643
0.6957	Remote Similarity	NPC167383
0.6863	Remote Similarity	NPC295371
0.6827	Remote Similarity	NPC104071
0.6809	Remote Similarity	NPC237503
0.6765	Remote Similarity	NPC150400
0.6762	Remote Similarity	NPC102439
0.6727	Remote Similarity	NPC75287
0.6726	Remote Similarity	NPC123199
0.6698	Remote Similarity	NPC63159
0.6696	Remote Similarity	NPC481080
0.661	Remote Similarity	NPC65105
0.661	Remote Similarity	NPC43550
0.6571	Remote Similarity	NPC223301
0.6571	Remote Similarity	NPC171544
0.6525	Remote Similarity	NPC41061
0.6525	Remote Similarity	NPC227551
0.6522	Remote Similarity	NPC475160
0.6522	Remote Similarity	NPC473714
0.6514	Remote Similarity	NPC104372
0.6505	Remote Similarity	NPC475516
0.6496	Remote Similarity	NPC476068
0.6417	Remote Similarity	NPC305981
0.6417	Remote Similarity	NPC481081
0.6396	Remote Similarity	NPC69811
0.6379	Remote Similarity	NPC191827
0.6364	Remote Similarity	NPC261506
0.6364	Remote Similarity	NPC298034
0.6364	Remote Similarity	NPC71065
0.6364	Remote Similarity	NPC4328
0.6341	Remote Similarity	NPC250247
0.6286	Remote Similarity	NPC473373
0.6198	Remote Similarity	NPC293330
0.6195	Remote Similarity	NPC481078
0.6148	Remote Similarity	NPC135849
0.6102	Remote Similarity	NPC470218
0.605	Remote Similarity	NPC488560
0.6036	Remote Similarity	NPC475504
0.6019	Remote Similarity	NPC473343
0.6018	Remote Similarity	NPC481079
0.6017	Remote Similarity	NPC135904
0.6016	Remote Similarity	NPC202828
0.6016	Remote Similarity	NPC119592
0.6016	Remote Similarity	NPC236638
0.6016	Remote Similarity	NPC294453
0.6	Remote Similarity	NPC159309
0.6	Remote Similarity	NPC86222
0.5983	Remote Similarity	NPC192600
0.5966	Remote Similarity	NPC100639
0.5965	Remote Similarity	NPC295823
0.5965	Remote Similarity	NPC174720
0.5965	Remote Similarity	NPC241909
0.5965	Remote Similarity	NPC475467
0.5962	Remote Similarity	NPC214484
0.5926	Remote Similarity	NPC39211
0.5909	Remote Similarity	NPC109588
0.5909	Remote Similarity	NPC309714
0.59	Remote Similarity	NPC306746
0.5872	Remote Similarity	NPC469946
0.5856	Remote Similarity	NPC305267
0.5818	Remote Similarity	NPC112352
0.5812	Remote Similarity	NPC476992
0.5789	Remote Similarity	NPC114484
0.5769	Remote Similarity	NPC209894
0.5766	Remote Similarity	NPC30735
0.5763	Remote Similarity	NPC60557
0.5763	Remote Similarity	NPC76972
0.5763	Remote Similarity	NPC469782
0.5763	Remote Similarity	NPC67857
0.5763	Remote Similarity	NPC204414
0.5752	Remote Similarity	NPC222580
0.575	Remote Similarity	NPC155410
0.5741	Remote Similarity	NPC235405
0.5726	Remote Similarity	NPC258617
0.5714	Remote Similarity	NPC191763
0.5714	Remote Similarity	NPC251768
0.5714	Remote Similarity	NPC476991
0.5688	Remote Similarity	NPC249848
0.5688	Remote Similarity	NPC107966
0.5676	Remote Similarity	NPC242840
0.5669	Remote Similarity	NPC70809
0.5664	Remote Similarity	NPC235438
0.566	Remote Similarity	NPC90856
0.563	Remote Similarity	NPC475287
0.5614	Remote Similarity	NPC297263
0.56	Remote Similarity	NPC475514
0.5575	Remote Similarity	NPC10607
0.5575	Remote Similarity	NPC46665
0.5565	Remote Similarity	NPC473386
0.5556	Remote Similarity	NPC96641
0.5556	Remote Similarity	NPC163183
0.5556	Remote Similarity	NPC80986
0.5545	Remote Similarity	NPC173583
0.5545	Remote Similarity	NPC46388
0.5536	Remote Similarity	NPC192791
0.5534	Remote Similarity	NPC68419
0.5526	Remote Similarity	NPC470515
0.5508	Remote Similarity	NPC31838
0.5504	Remote Similarity	NPC220160
0.5495	Remote Similarity	NPC473884
0.5495	Remote Similarity	NPC157868
0.547	Remote Similarity	NPC301449
0.547	Remote Similarity	NPC601290
0.5439	Remote Similarity	NPC40775
0.5439	Remote Similarity	NPC101744
0.5439	Remote Similarity	NPC480475
0.5437	Remote Similarity	NPC37739
0.5437	Remote Similarity	NPC199457
0.5391	Remote Similarity	NPC148417
0.5391	Remote Similarity	NPC136768
0.5391	Remote Similarity	NPC475591
0.5391	Remote Similarity	NPC236870
0.5385	Remote Similarity	NPC281148
0.5385	Remote Similarity	NPC137917
0.5385	Remote Similarity	NPC51564
0.5378	Remote Similarity	NPC187290
0.5315	Remote Similarity	NPC139894
0.5268	Remote Similarity	NPC58448
0.5267	Remote Similarity	NPC224381
0.5238	Remote Similarity	NPC604133
0.5182	Remote Similarity	NPC1046
0.5182	Remote Similarity	NPC475368
0.5175	Remote Similarity	NPC471547
0.5167	Remote Similarity	NPC481030
0.5161	Remote Similarity	NPC246708
0.5159	Remote Similarity	NPC25663
0.5156	Remote Similarity	NPC110633
0.5156	Remote Similarity	NPC480418
0.5133	Remote Similarity	NPC480420
0.5111	Remote Similarity	NPC480422
0.5093	Remote Similarity	NPC128925
0.5093	Remote Similarity	NPC256798
0.5088	Remote Similarity	NPC470512
0.5086	Remote Similarity	NPC471548
0.5078	Remote Similarity	NPC57484
0.5043	Remote Similarity	NPC473401
0.5043	Remote Similarity	NPC76497
0.5041	Remote Similarity	NPC480473
0.5041	Remote Similarity	NPC470516
0.504	Remote Similarity	NPC475899
0.504	Remote Similarity	NPC470911
0.504	Remote Similarity	NPC481031
0.5033	Remote Similarity	NPC481323
0.5033	Remote Similarity	NPC469778

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473459 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7563
0.1-0.2	1526
0.2-0.3	56
0.3-0.4	5
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