NPASS Compound

Natural Product: NPC476992

Natural Product ID	NPC476992
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	vaccaroid C
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-[(2S,3R,4S,5R,6R)-6-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxycarbonyl-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-carboxylic acid
Synonyms	Vaccaroid C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	45268017
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 165173 0 0 0 0 0 0 0 0999 V2000 -4.0790 0.1513 2.8389 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5611 -0.4290 1.5857 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7065 -1.6450 2.0010 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2889 -1.3146 2.2221 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9614 0.1131 2.4450 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5012 1.0220 1.3281 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6800 0.4004 0.7071 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4368 1.3100 -0.2289 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5058 0.5577 -1.0164 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4942 -0.0839 -0.0221 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6528 -1.0511 0.7189 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3595 -2.0662 1.5260 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7884 -2.2147 1.2353 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3666 -1.6477 0.2212 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6002 -0.8004 -0.7174 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4959 0.0880 -1.5287 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7908 0.4491 -0.8887 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5490 -0.6711 -0.2474 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8097 -1.9130 0.0279 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0663 -2.9993 -0.9915 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4810 -3.5140 -0.6756 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4110 -2.3213 -0.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7344 -1.0585 -1.1568 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5307 -4.0918 0.7373 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9126 -4.5958 -1.6220 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1684 -0.1919 1.0243 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.4160 -0.1812 1.1185 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4586 0.2466 2.1228 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9338 -1.7912 -1.6890 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0601 1.0667 0.7378 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 2.3731 1.9344 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3862 1.1132 0.3405 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5802 0.7532 -0.8325 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8583 1.5831 0.6861 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9784 1.6959 -0.2164 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3914 3.1290 -0.1580 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7691 3.4279 -0.6637 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7247 2.4616 0.0299 C 0 0 1 0 0 0 0 0 0 0 0 0 4.2276 1.0381 -0.1015 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9390 0.8871 0.3257 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0862 0.2049 0.8420 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7351 -1.1428 0.7894 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9425 -1.7015 -0.4500 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6993 -3.0091 -0.4158 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8430 -3.4357 -1.8601 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4762 -3.6072 -2.4974 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7311 -2.3045 -2.3154 C 0 0 2 0 0 0 0 0 0 0 0 0 3.6546 -2.0501 -0.9455 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3210 -2.5176 -2.8103 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5395 -1.3912 -2.5824 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6670 -3.8580 -3.8532 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6494 -4.5292 -2.0484 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9344 -2.9527 0.1416 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1484 -3.7885 1.2152 C 0 0 1 0 0 0 0 0 0 0 0 0 8.1599 -4.8596 1.0447 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5787 -4.4010 1.3633 C 0 0 2 0 0 0 0 0 0 0 0 0 9.5162 -3.9063 2.7899 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4870 -2.8320 2.8984 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2718 -3.0666 2.3599 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1017 -1.4918 2.5182 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1913 -0.5213 2.9835 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1869 -4.9626 3.6363 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0154 -3.4281 0.4964 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8734 -5.8359 2.0351 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0182 2.5494 -0.4165 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1444 4.6930 -0.1476 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6244 5.5529 -1.0987 C 0 0 1 0 0 0 0 0 0 0 0 0 3.8932 6.8657 -1.1805 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5200 7.6485 -2.3441 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9385 7.9511 -1.9524 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6100 6.6220 -1.6749 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9463 5.8733 -0.7399 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9709 6.9696 -1.0571 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7216 7.7325 -1.9286 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6563 8.5881 -2.9420 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8049 8.8148 -2.5867 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5549 6.7689 -1.4611 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5131 3.9577 -0.8700 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2550 0.6083 3.7088 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7703 -0.4203 3.7738 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8526 1.1901 3.0632 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2082 0.0629 2.9465 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7758 -2.4724 1.2739 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1357 -2.0665 2.9602 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6789 -1.6574 1.3343 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8954 -1.8964 3.0702 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1751 0.1585 2.4168 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2468 -0.3735 -0.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7000 1.5933 -1.0445 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7539 2.2631 0.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9332 -0.2148 -1.5732 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9939 1.2936 -1.6499 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0541 -1.6090 -0.0664 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9077 -3.0923 1.3589 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2570 -1.9383 2.6266 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3633 -2.8477 1.9366 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7410 -0.4392 -2.4840 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0158 1.0361 -1.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7444 1.2804 -0.1561 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4537 0.8659 -1.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2385 -2.3404 0.9918 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1382 -2.6197 -2.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4039 -3.8545 -0.8600 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9949 -2.2145 0.2131 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1776 -2.5417 -1.5087 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4435 -1.1005 -2.2035 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5237 -0.2531 -1.0769 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2070 -4.9873 0.7902 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4888 -4.3649 1.0091 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9397 -3.3587 1.4622 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7750 -4.2771 -2.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2786 -5.4989 -1.0776 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1140 -4.9177 -2.3171 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8027 1.0338 2.6656 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3789 -1.2816 -2.4926 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4203 -2.6039 -1.1854 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8006 -2.2722 -2.2304 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4395 1.7915 -0.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9359 0.8208 1.3610 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3258 1.7076 1.2667 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4135 2.4005 3.0122 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6726 2.8358 1.7882 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9710 3.1194 1.4737 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6661 1.3733 -1.2334 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3716 3.4257 0.9307 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8900 3.3730 -1.7469 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6880 2.7149 1.1098 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3849 0.7451 -1.1548 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9455 0.5414 1.8863 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1600 0.2762 0.6090 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3875 -1.0054 -1.1754 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0091 -3.7399 0.0570 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3185 -2.5870 -2.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9009 -4.4438 -2.0720 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2258 -1.5014 -2.8735 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2955 -2.7304 -3.9051 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8278 -3.3753 -2.3202 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9064 -0.6485 -3.1398 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4151 -3.3876 -4.2538 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5934 -4.2331 -2.0838 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1554 -4.3416 1.3433 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1002 -5.3921 0.0974 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2207 -5.2991 1.3063 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4837 -3.4886 3.0815 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3091 -2.7175 4.0188 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3390 -1.3909 1.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9989 -1.3701 3.1866 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5725 0.3686 2.9006 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6070 -4.5792 4.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9608 -3.2448 0.6850 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8910 -5.9785 2.0911 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5727 3.1126 0.1979 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5932 5.0719 -2.0961 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0726 7.4910 -0.2641 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5527 6.9706 -3.2120 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8835 8.5710 -1.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7893 6.1227 -2.6310 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7381 7.5682 -0.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4788 6.0346 -0.7204 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7947 7.2509 -2.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0454 9.1974 -3.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0687 8.9554 -1.9574 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9727 6.9376 -0.6756 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6075 3.7455 -0.5504 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5103 0.5752 4.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 1 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 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 1 0 22 23 1 0 21 24 1 0 21 25 1 0 18 26 1 1 26 27 2 0 26 28 1 0 15 29 1 6 10 30 1 1 6 31 1 1 6 32 1 0 32 33 2 0 32 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 1 0 39 41 1 0 41 42 1 0 42 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 46 51 1 0 45 52 1 0 44 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 58 60 1 0 60 61 1 0 57 62 1 0 56 63 1 0 55 64 1 0 38 65 1 0 37 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 71 73 1 0 73 74 1 0 70 75 1 0 69 76 1 0 68 77 1 0 36 78 1 0 5 79 1 0 7 2 1 0 11 2 1 0 15 10 1 0 19 14 1 0 23 18 1 0 40 35 1 0 48 43 1 0 59 54 1 0 72 67 1 0 1 80 1 0 1 81 1 0 1 82 1 0 3 83 1 0 3 84 1 0 4 85 1 0 4 86 1 0 5 87 1 6 7 88 1 6 8 89 1 0 8 90 1 0 9 91 1 0 9 92 1 0 11 93 1 6 12 94 1 0 12 95 1 0 13 96 1 0 16 97 1 0 16 98 1 0 17 99 1 0 17100 1 0 19101 1 1 20102 1 0 20103 1 0 22104 1 0 22105 1 0 23106 1 0 23107 1 0 24108 1 0 24109 1 0 24110 1 0 25111 1 0 25112 1 0 25113 1 0 28114 1 0 29115 1 0 29116 1 0 29117 1 0 30118 1 0 30119 1 0 30120 1 0 31121 1 0 31122 1 0 31123 1 0 35124 1 6 36125 1 1 37126 1 6 38127 1 1 39128 1 6 41129 1 0 41130 1 0 43131 1 6 44132 1 1 45133 1 6 46134 1 1 47135 1 6 49136 1 0 49137 1 0 50138 1 0 51139 1 0 52140 1 0 54141 1 1 55142 1 6 56143 1 1 57144 1 1 58145 1 1 60146 1 0 60147 1 0 61148 1 0 62149 1 0 63150 1 0 64151 1 0 65152 1 0 67153 1 6 68154 1 1 69155 1 6 70156 1 1 71157 1 6 73158 1 0 73159 1 0 74160 1 0 75161 1 0 76162 1 0 77163 1 0 78164 1 0 79165 1 0 M END

Standard InCHIKey	ZUSHLPYWFHLHCL-FHEJOWGISA-N
Standard InCHI	InChI=1S/C54H86O25/c1-49(2)13-15-54(47(69)70)16-14-51(4)22(23(54)17-49)7-8-28-50(3)11-10-30(58)53(6,29(50)9-12-52(28,51)5)48(71)79-45-40(68)41(77-43-38(66)35(63)31(59)24(18-55)73-43)34(62)27(76-45)21-72-46-42(37(65)33(61)26(20-57)75-46)78-44-39(67)36(64)32(60)25(19-56)74-44/h7,23-46,55-68H,8-21H2,1-6H3,(H,69,70)/t23-,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-,54-/m0/s1
SMILES	C[C@]12CC[C@@H]([C@@]([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1134.55	Volume:	1077.378 ? Van der Waals volume.
Dense:	1.053	LogP:	-1.04 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.915 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.533 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	52.0
TPSA:	411.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	15.0	Rings:	9.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.065	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.903	Fsp³:	0.926
MCE-18:	199.385 ? 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:	0.692	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.01 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.236	Promiscuous compounds:	0.208

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.882	MDCK Permeability:	-5.026
Pgp-inhibitor:	0.0	Pgp-substrate:	0.028
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):	0.935
20% Bioavailability (F20%):	0.05	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.034
Plasma Protein Binding (PPB):	69.845%	Volume Distribution (VD):	-0.438
Fu:	19.896% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
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:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.028 ? 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):

-0.748

Half-life (T1/2):

4.561

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.828	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.982	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.205	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.828	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.697	RPMI-8226 Immunitoxicity:	0.128
A549 Cytotoxicity:	0.748	Hek293 Cytotoxicity:	0.104
BCF:	0.493 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.289 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.857 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.739 ? 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
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19290648]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	aerial parts	Changqing, Shangdong Province, China	2004-JUN	PMID[19290648]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27907	Dianthus versicolor	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	5

Activity Type	# Activity
Cell line	3
Others	2

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
NPT1855	Cell line	HFL1	Homo sapiens	IC50	=	3800	nM	PMID[19290648]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000	nM	PMID[19290648]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000	nM	PMID[19290648]
NPT27	Others	Unspecified	n.a.	IC50	=	8700	nM	PMID[19290648]
NPT2	Others	Unspecified	n.a.	IC50	=	9400	nM	PMID[19290648]

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 NPC476992 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	22386
0.1-0.2	22983
0.2-0.3	3151
0.3-0.4	889
0.4-0.5	353
0.5-0.6	59
0.6-0.7	34
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
0.7207	Intermediate Similarity	NPC69811
0.6983	Remote Similarity	NPC323341
0.6923	Remote Similarity	NPC166422
0.6909	Remote Similarity	NPC139044
0.6881	Remote Similarity	NPC114304
0.6847	Remote Similarity	NPC257468
0.6829	Remote Similarity	NPC476991
0.6814	Remote Similarity	NPC323359
0.6807	Remote Similarity	NPC54636
0.6783	Remote Similarity	NPC75287
0.6726	Remote Similarity	NPC276093
0.6667	Remote Similarity	NPC324875
0.6667	Remote Similarity	NPC292677
0.6639	Remote Similarity	NPC219180
0.6609	Remote Similarity	NPC488564
0.6604	Remote Similarity	NPC270667
0.6604	Remote Similarity	NPC164194
0.6532	Remote Similarity	NPC471385
0.6518	Remote Similarity	NPC180550
0.6518	Remote Similarity	NPC35405
0.6422	Remote Similarity	NPC59804
0.6372	Remote Similarity	NPC305267
0.6364	Remote Similarity	NPC127056
0.633	Remote Similarity	NPC136877
0.633	Remote Similarity	NPC12288
0.6316	Remote Similarity	NPC471383
0.6311	Remote Similarity	NPC191827
0.6281	Remote Similarity	NPC133818
0.6273	Remote Similarity	NPC25605
0.623	Remote Similarity	NPC251263
0.6161	Remote Similarity	NPC488561
0.6129	Remote Similarity	NPC25663
0.6094	Remote Similarity	NPC135849
0.6058	Remote Similarity	NPC204407
0.6	Remote Similarity	NPC606107
0.5983	Remote Similarity	NPC609763
0.5954	Remote Similarity	NPC51564
0.5891	Remote Similarity	NPC161717
0.5887	Remote Similarity	NPC471384
0.5877	Remote Similarity	NPC472949
0.5847	Remote Similarity	NPC481082
0.5847	Remote Similarity	NPC164419
0.5841	Remote Similarity	NPC174679
0.5841	Remote Similarity	NPC279554
0.5812	Remote Similarity	NPC104400
0.5812	Remote Similarity	NPC10320
0.5812	Remote Similarity	NPC473459
0.5789	Remote Similarity	NPC109079
0.5738	Remote Similarity	NPC475486
0.5702	Remote Similarity	NPC56713
0.5678	Remote Similarity	NPC473383
0.5667	Remote Similarity	NPC79718
0.5667	Remote Similarity	NPC119794
0.5446	Remote Similarity	NPC284807
0.544	Remote Similarity	NPC62725
0.5424	Remote Similarity	NPC80843
0.5424	Remote Similarity	NPC22956
0.5378	Remote Similarity	NPC469945
0.5373	Remote Similarity	NPC111466
0.5312	Remote Similarity	NPC151543
0.5276	Remote Similarity	NPC288205
0.5276	Remote Similarity	NPC51465
0.5273	Remote Similarity	NPC28198
0.5273	Remote Similarity	NPC476123
0.5254	Remote Similarity	NPC114441
0.5207	Remote Similarity	NPC309714
0.52	Remote Similarity	NPC480946
0.52	Remote Similarity	NPC130577
0.52	Remote Similarity	NPC142415
0.52	Remote Similarity	NPC102683
0.5194	Remote Similarity	NPC79643
0.5185	Remote Similarity	NPC293330
0.5185	Remote Similarity	NPC65105
0.5172	Remote Similarity	NPC29069
0.5159	Remote Similarity	NPC488209
0.5149	Remote Similarity	NPC270768
0.5149	Remote Similarity	NPC59263
0.5149	Remote Similarity	NPC210106
0.5135	Remote Similarity	NPC283849
0.5133	Remote Similarity	NPC100383
0.513	Remote Similarity	NPC191410
0.5126	Remote Similarity	NPC150400
0.5122	Remote Similarity	NPC258885
0.5083	Remote Similarity	NPC6377
0.5083	Remote Similarity	NPC208381
0.5081	Remote Similarity	NPC475504
0.5078	Remote Similarity	NPC480939
0.5078	Remote Similarity	NPC280941
0.5078	Remote Similarity	NPC235772
0.5074	Remote Similarity	NPC43550
0.5049	Remote Similarity	NPC298554
0.5044	Remote Similarity	NPC31839
0.5043	Remote Similarity	NPC475633
0.504	Remote Similarity	NPC488515

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476992 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6819
0.1-0.2	2276
0.2-0.3	49
0.3-0.4	6
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