NPASS Compound

Natural Product: NPC161674

Natural Product ID	NPC161674
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Latifoloside C
IUPAC Name	[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1S,4aR,6aR,6aS,6bR,8aR,10S,12aR,14bS)-1-hydroxy-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	Latifoloside C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL506924
PubChem CID	44566326
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 161169 0 0 0 0 0 0 0 0999 V2000 -9.1246 4.3329 4.2039 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8509 3.5484 3.2965 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2762 3.7740 1.8805 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9749 3.3906 1.9344 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4355 2.8565 0.7541 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4240 1.4647 0.9131 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0963 1.0856 1.1025 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9286 0.6746 2.5883 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0378 1.1997 3.2939 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9756 -0.8009 2.7727 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9651 -1.4724 2.0806 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4225 -0.6360 1.0881 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6131 -0.0749 0.3164 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2243 0.1290 -0.9808 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9103 -0.7615 -1.8036 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0009 -1.7871 -2.2275 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8015 -2.8654 -2.5921 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5267 -3.4549 -1.3997 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7127 -2.5673 -3.7384 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4209 -1.2437 -3.6338 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5250 -0.1789 -3.0166 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3113 0.9090 -2.6957 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5897 -1.3191 -2.9007 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9840 -2.6811 -4.9332 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4692 -1.2539 0.3407 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2325 -0.7047 0.5863 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3372 -1.7016 1.3186 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4526 -2.4806 0.4041 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5362 -1.5787 -0.3342 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0572 -0.1972 -0.3113 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5263 -0.1153 -0.6070 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8196 1.3955 -0.6679 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9551 -0.7065 -1.8879 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8082 0.7672 -1.0522 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0960 0.8923 -0.2479 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7391 -0.4118 0.0558 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7783 -1.4753 0.5383 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4407 -2.7494 0.8647 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9057 -2.6208 1.0974 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5218 -1.4625 1.2618 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7317 -0.2156 1.2155 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9671 -0.0754 2.5218 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5705 1.0067 1.0623 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7304 0.9625 1.9791 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6499 -0.2142 1.7286 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0019 -1.5067 1.4899 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2095 -2.6171 2.4622 C 0 0 2 0 0 0 0 0 0 0 0 0 5.0407 -2.7966 3.2420 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3360 -2.4917 3.4187 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1568 -3.5398 4.5039 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6932 -2.6814 2.7909 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1913 -1.0898 4.0366 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5998 -0.1901 2.9177 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5220 0.2139 0.5739 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7967 0.2427 0.6739 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0283 0.5942 -0.6332 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7588 1.0051 -1.7533 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5240 2.3471 -2.0776 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6549 2.7896 -2.7597 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6328 4.2858 -2.9706 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7773 4.6857 -3.6526 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8142 2.0932 -4.0698 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6592 0.6028 -3.9741 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5453 0.2113 -2.9915 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6289 -1.1568 -2.8377 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4586 0.0472 -5.2185 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1287 2.3616 -4.5148 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5359 -0.8393 -1.1352 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7563 -2.1572 -1.6722 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1837 3.3515 -0.4193 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5620 2.7100 -0.3908 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1714 3.0222 0.9578 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.3054 3.8292 0.7089 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3776 1.3320 -0.4917 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3065 4.7586 -0.2808 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4138 5.2875 4.0447 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9088 3.8264 3.3340 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6822 2.4935 3.6170 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4264 4.8814 1.7290 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3944 3.2698 0.7387 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3860 1.9347 1.0037 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0329 1.1046 3.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8176 0.5994 3.1763 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7906 -1.0050 3.8474 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9800 -1.2319 2.5562 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9615 0.1935 1.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4258 -0.8758 0.3666 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6571 -1.3377 -1.2230 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0912 -3.6648 -2.9401 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0346 -3.1227 -0.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4669 -4.5629 -1.3956 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5936 -3.1986 -1.3785 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5205 -3.3509 -3.7456 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6688 -0.9038 -4.6685 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7383 0.1301 -3.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2145 1.6449 -3.3748 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9767 -2.2302 -3.0854 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6270 -2.5100 -5.6728 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3341 0.1382 1.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7384 -1.2172 2.1149 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0170 -2.4089 1.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0305 -3.1188 -0.2647 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1399 -3.1727 1.0541 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0115 0.1334 0.7754 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2769 1.9132 0.1509 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5837 1.7495 -1.6703 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9107 1.4939 -0.5071 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8217 -0.1265 -2.2730 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3278 -1.7385 -1.7274 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2046 -0.6514 -2.7024 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3585 1.7812 -1.0475 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9987 0.5157 -2.1016 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7936 1.4778 -0.9078 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8740 1.5326 0.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3519 -1.0620 1.5035 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2730 -3.5820 0.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0359 -3.1783 1.8313 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4595 -3.5767 1.1236 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7239 -1.0495 2.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0672 0.5945 2.4038 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5798 0.4577 3.2764 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9359 1.8970 1.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9031 1.2241 0.0430 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4986 0.9564 3.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3833 1.8860 1.8596 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3955 -1.8935 0.4966 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3297 -3.6029 1.9355 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2111 -2.7741 4.1961 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4889 -4.3731 4.1581 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1252 -4.0164 4.7410 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7963 -3.0895 5.4517 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9172 -3.7880 2.8338 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6891 -2.4337 1.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5004 -2.1923 3.3676 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8673 -0.9349 4.8740 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1290 -0.9537 4.2600 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7926 0.8574 3.2004 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5917 -0.5685 2.5332 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8346 0.9569 -1.4811 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5791 2.5591 -2.1572 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5833 4.8399 -2.0266 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7648 4.5116 -3.6492 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1437 5.5451 -3.3376 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1507 2.5504 -4.8397 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6058 0.2049 -3.5098 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6017 0.5222 -3.5060 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3853 -1.3502 -2.2290 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2179 -0.5527 -5.4264 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7767 2.2580 -3.7653 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0971 -0.3588 -2.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6555 -1.9293 -1.2488 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5642 -0.4313 -1.0897 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1669 -2.7203 -2.0046 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0274 -1.4831 -2.4816 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5357 -2.9551 -1.6508 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7102 3.2142 -1.3920 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1728 3.0523 -1.2251 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5072 2.0779 1.4409 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0614 3.1987 0.6038 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9740 0.8239 0.1309 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1364 4.9889 -0.7719 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 47 49 1 0 49 50 1 0 49 51 1 0 49 52 1 0 52 53 1 0 45 54 1 6 54 55 2 0 54 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 59 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 63 66 1 0 62 67 1 0 36 68 1 6 29 69 1 6 5 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 71 74 1 0 70 75 1 0 72 3 1 0 13 7 1 0 21 15 1 0 31 26 1 0 41 36 1 0 53 45 1 0 64 57 1 0 37 29 1 0 46 40 1 0 1 76 1 0 2 77 1 0 2 78 1 0 3 79 1 6 5 80 1 6 7 81 1 1 8 82 1 1 9 83 1 0 10 84 1 0 10 85 1 0 12 86 1 1 13 87 1 6 15 88 1 1 17 89 1 6 18 90 1 0 18 91 1 0 18 92 1 0 19 93 1 6 20 94 1 6 21 95 1 6 22 96 1 0 23 97 1 0 24 98 1 0 26 99 1 1 27100 1 0 27101 1 0 28102 1 0 28103 1 0 30104 1 1 32105 1 0 32106 1 0 32107 1 0 33108 1 0 33109 1 0 33110 1 0 34111 1 0 34112 1 0 35113 1 0 35114 1 0 37115 1 1 38116 1 0 38117 1 0 39118 1 0 42119 1 0 42120 1 0 42121 1 0 43122 1 0 43123 1 0 44124 1 0 44125 1 0 46126 1 6 47127 1 6 48128 1 0 50129 1 0 50130 1 0 50131 1 0 51132 1 0 51133 1 0 51134 1 0 52135 1 0 52136 1 0 53137 1 0 53138 1 0 57139 1 1 59140 1 1 60141 1 0 60142 1 0 61143 1 0 62144 1 6 63145 1 1 64146 1 6 65147 1 0 66148 1 0 67149 1 0 68150 1 0 68151 1 0 68152 1 0 69153 1 0 69154 1 0 69155 1 0 70156 1 6 71157 1 6 72158 1 1 73159 1 0 74160 1 0 75161 1 0 M END

Standard InCHIKey	OWJMPCBRZTYZJR-MZRTYAAGSA-N
Standard InCHI	InChI=1S/C53H86O22/c1-22-31(57)34(60)37(63)43(69-22)74-41-40(73-44-38(64)35(61)32(58)25(19-54)70-44)24(56)21-68-46(41)72-29-12-13-50(6)27(49(29,4)5)11-14-52(8)28(50)10-9-23-30-42(66)48(2,3)15-17-53(30,18-16-51(23,52)7)47(67)75-45-39(65)36(62)33(59)26(20-55)71-45/h9,22,24-46,54-66H,10-21H2,1-8H3/t22-,24-,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]3[C@H](O)C(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

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
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]

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	1

Activity Type	# Activity
Individual protein	1

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	=	20.0	%	PMID[12762807]

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 NPC161674 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	22976
0.1-0.2	22433
0.2-0.3	3009
0.3-0.4	911
0.4-0.5	348
0.5-0.6	133
0.6-0.7	34
0.7-0.8	0
0.8-0.85	2
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	NPC46665
0.8316	Intermediate Similarity	NPC68175
0.7476	Intermediate Similarity	NPC36831
0.74	Intermediate Similarity	NPC148417
0.7391	Intermediate Similarity	NPC128925
0.7103	Intermediate Similarity	NPC268184
0.6931	Remote Similarity	NPC112352
0.6863	Remote Similarity	NPC160415
0.6847	Remote Similarity	NPC100639
0.6724	Remote Similarity	NPC481081
0.6667	Remote Similarity	NPC263756
0.6667	Remote Similarity	NPC256798
0.6609	Remote Similarity	NPC110633
0.6593	Remote Similarity	NPC191763
0.6476	Remote Similarity	NPC10607
0.646	Remote Similarity	NPC135904
0.6441	Remote Similarity	NPC136768
0.6415	Remote Similarity	NPC475591
0.6415	Remote Similarity	NPC236870
0.6383	Remote Similarity	NPC605954
0.6316	Remote Similarity	NPC116794
0.6273	Remote Similarity	NPC80986
0.6262	Remote Similarity	NPC63159
0.6216	Remote Similarity	NPC187290
0.6214	Remote Similarity	NPC475516
0.6195	Remote Similarity	NPC60557
0.6195	Remote Similarity	NPC67857
0.6176	Remote Similarity	NPC48499
0.6168	Remote Similarity	NPC480475
0.6154	Remote Similarity	NPC58448
0.6121	Remote Similarity	NPC475160
0.6121	Remote Similarity	NPC473714
0.6087	Remote Similarity	NPC165204
0.6075	Remote Similarity	NPC117714
0.6058	Remote Similarity	NPC235405
0.6034	Remote Similarity	NPC155410
0.6033	Remote Similarity	NPC305981
0.6	Remote Similarity	NPC249848
0.6	Remote Similarity	NPC79643
0.6	Remote Similarity	NPC107966
0.5984	Remote Similarity	NPC261506
0.5984	Remote Similarity	NPC4328
0.598	Remote Similarity	NPC204458
0.598	Remote Similarity	NPC90856
0.598	Remote Similarity	NPC214484
0.5966	Remote Similarity	NPC476068
0.5929	Remote Similarity	NPC481078
0.5926	Remote Similarity	NPC30735
0.5922	Remote Similarity	NPC78046
0.5893	Remote Similarity	NPC481079
0.5888	Remote Similarity	NPC469946
0.5868	Remote Similarity	NPC41061
0.5868	Remote Similarity	NPC227551
0.5868	Remote Similarity	NPC258617
0.5841	Remote Similarity	NPC295823
0.5841	Remote Similarity	NPC174720
0.5841	Remote Similarity	NPC475467
0.5833	Remote Similarity	NPC192791
0.5833	Remote Similarity	NPC57484
0.582	Remote Similarity	NPC43550
0.5818	Remote Similarity	NPC235438
0.5804	Remote Similarity	NPC114484
0.5794	Remote Similarity	NPC39211
0.5766	Remote Similarity	NPC222580
0.5763	Remote Similarity	NPC123199
0.5741	Remote Similarity	NPC213674
0.5727	Remote Similarity	NPC251768
0.5702	Remote Similarity	NPC480473
0.5702	Remote Similarity	NPC480474
0.5667	Remote Similarity	NPC488560
0.5645	Remote Similarity	NPC236638
0.5645	Remote Similarity	NPC294453
0.5641	Remote Similarity	NPC475287
0.5641	Remote Similarity	NPC76972
0.5641	Remote Similarity	NPC469782
0.5641	Remote Similarity	NPC204414
0.5625	Remote Similarity	NPC297263
0.5607	Remote Similarity	NPC108748
0.5591	Remote Similarity	NPC250247
0.5586	Remote Similarity	NPC164389
0.5586	Remote Similarity	NPC173859
0.5586	Remote Similarity	NPC148603
0.5583	Remote Similarity	NPC471550
0.5565	Remote Similarity	NPC293330
0.5545	Remote Similarity	NPC223301
0.5545	Remote Similarity	NPC171544
0.5526	Remote Similarity	NPC281148
0.5505	Remote Similarity	NPC157868
0.5492	Remote Similarity	NPC481080
0.5478	Remote Similarity	NPC301449
0.5478	Remote Similarity	NPC601290
0.5476	Remote Similarity	NPC298034
0.5476	Remote Similarity	NPC71065
0.547	Remote Similarity	NPC470915
0.5446	Remote Similarity	NPC40775
0.5446	Remote Similarity	NPC159309
0.5446	Remote Similarity	NPC86222
0.5429	Remote Similarity	NPC47063
0.5413	Remote Similarity	NPC473373
0.5405	Remote Similarity	NPC75417
0.5391	Remote Similarity	NPC104372
0.5385	Remote Similarity	NPC31838
0.5377	Remote Similarity	NPC189884
0.5377	Remote Similarity	NPC269095
0.5377	Remote Similarity	NPC138334
0.5357	Remote Similarity	NPC309714
0.5354	Remote Similarity	NPC302543
0.5351	Remote Similarity	NPC470478
0.5328	Remote Similarity	NPC470218
0.5317	Remote Similarity	NPC65105
0.531	Remote Similarity	NPC101744
0.53	Remote Similarity	NPC167383
0.5299	Remote Similarity	NPC96641
0.5299	Remote Similarity	NPC163183
0.5299	Remote Similarity	NPC241909
0.5285	Remote Similarity	NPC47995
0.5283	Remote Similarity	NPC161434
0.5273	Remote Similarity	NPC109079
0.5271	Remote Similarity	NPC220160
0.5248	Remote Similarity	NPC46388
0.5243	Remote Similarity	NPC187056
0.5243	Remote Similarity	NPC606216
0.5243	Remote Similarity	NPC607023
0.5238	Remote Similarity	NPC475514
0.5234	Remote Similarity	NPC473481
0.5225	Remote Similarity	NPC295371
0.5225	Remote Similarity	NPC470512
0.5221	Remote Similarity	NPC104071
0.5221	Remote Similarity	NPC30289
0.5217	Remote Similarity	NPC475504
0.5203	Remote Similarity	NPC283417
0.5203	Remote Similarity	NPC200049
0.5196	Remote Similarity	NPC237503
0.5194	Remote Similarity	NPC70809
0.5192	Remote Similarity	NPC110139
0.5192	Remote Similarity	NPC108709
0.5185	Remote Similarity	NPC1046
0.5185	Remote Similarity	NPC475368
0.5179	Remote Similarity	NPC76497
0.5179	Remote Similarity	NPC22956
0.5175	Remote Similarity	NPC102439
0.5175	Remote Similarity	NPC2370
0.5172	Remote Similarity	NPC134835
0.5172	Remote Similarity	NPC79718
0.5164	Remote Similarity	NPC470911
0.5156	Remote Similarity	NPC202828
0.5156	Remote Similarity	NPC119592
0.5154	Remote Similarity	NPC224381
0.5146	Remote Similarity	NPC37739
0.5135	Remote Similarity	NPC127056
0.5113	Remote Similarity	NPC480422
0.5096	Remote Similarity	NPC7870
0.5096	Remote Similarity	NPC137917
0.5096	Remote Similarity	NPC310014
0.5096	Remote Similarity	NPC68419
0.5096	Remote Similarity	NPC269315
0.5096	Remote Similarity	NPC75747
0.5088	Remote Similarity	NPC605226
0.5086	Remote Similarity	NPC257468
0.5083	Remote Similarity	NPC62725
0.5082	Remote Similarity	NPC192600
0.5079	Remote Similarity	NPC484061
0.5079	Remote Similarity	NPC21691
0.5079	Remote Similarity	NPC484062
0.5076	Remote Similarity	NPC480417
0.5048	Remote Similarity	NPC271138
0.5048	Remote Similarity	NPC102914
0.5047	Remote Similarity	NPC209894
0.5046	Remote Similarity	NPC29069
0.5045	Remote Similarity	NPC25605
0.5045	Remote Similarity	NPC56713
0.5043	Remote Similarity	NPC44716
0.5039	Remote Similarity	NPC286457

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC161674 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7489
0.1-0.2	1600
0.2-0.3	50
0.3-0.4	11
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