NPASS Compound

Natural Product: NPC44716

Natural Product ID	NPC44716
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gummososide A
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8S,8aR,12aS,14aR,14bR)-8a-formyl-8-hydroxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-4,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid
Synonyms	gummososide A
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2047210
PubChem CID	70692511
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 143150 0 0 0 0 0 0 0 0999 V2000 -5.9388 -6.3253 -0.6822 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1320 -6.0650 0.4180 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3996 -4.6117 0.8279 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0696 -3.8434 -0.2644 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4132 -2.4847 -0.0787 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0267 -1.8394 -1.2333 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0779 -0.8269 -1.0043 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8534 -1.2193 -1.8364 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3283 -1.3992 -3.1258 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7740 -0.2629 -3.7554 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0302 0.8775 -2.8319 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6753 0.4533 -1.5559 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5651 1.4326 -0.5608 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7838 1.9287 -0.1362 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7611 3.3206 -0.3348 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9454 3.9158 0.0175 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.7828 5.4161 -0.1499 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4725 5.7110 -1.4717 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4192 3.6161 1.3997 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2628 2.1765 1.7833 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8634 1.7553 1.3761 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5684 0.4724 1.7638 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3518 2.0164 3.1654 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7976 3.9032 1.4622 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9528 1.7412 -3.4690 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8728 0.1643 -4.8607 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8382 -0.4797 -5.1547 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1705 1.2991 -5.5932 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8637 -0.2892 -1.8500 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5996 -0.7454 -1.4752 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3978 -0.6956 -2.5805 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8179 -0.5009 -2.1888 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0254 0.6355 -1.1777 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2095 0.2682 -0.0007 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2142 -0.1062 -0.1966 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0625 1.1512 -0.0142 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6634 -1.0283 0.9616 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3786 1.3094 1.1138 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8071 1.0658 1.6269 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8110 1.2463 0.5307 C 0 0 2 0 0 0 0 0 0 0 0 0 3.4771 0.5506 -0.7412 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4548 0.8936 -1.8082 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8295 0.6606 -1.2818 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1543 0.5618 -0.0099 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1259 0.6808 1.0500 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9105 -0.6499 1.7621 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7078 1.6170 2.1094 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8651 0.8675 2.7312 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9752 0.6235 1.7326 C 0 0 2 0 0 0 0 0 0 0 0 0 7.5773 0.3188 0.3551 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0794 -1.0060 -0.1303 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4158 -1.4498 0.2851 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3957 -1.2943 -0.8651 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4905 -2.9073 0.6942 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0244 -0.6244 1.4261 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8697 -0.4213 2.3804 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8117 1.8803 1.7425 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9326 2.4869 0.7134 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3404 1.7268 3.7530 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9744 2.7491 0.3782 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6635 1.9058 -1.8625 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9222 -2.4543 0.0040 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3043 -3.0728 1.3310 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8257 -4.5228 1.2651 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9208 -5.0270 2.5643 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6602 -3.0745 1.5570 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3853 -1.1693 -0.1382 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3680 -6.3127 -1.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0650 -6.2150 0.1937 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4223 -6.6602 1.3145 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7179 -4.3987 1.6788 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9223 -2.0958 0.8365 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8424 -0.7671 0.0582 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5223 -2.2287 -1.5038 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7298 -0.5707 -4.2829 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1325 1.4955 -2.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7687 0.2913 -1.7944 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6386 1.4750 -0.6497 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7248 3.5274 -0.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9763 5.7987 0.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7162 5.9199 0.1829 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1590 6.2704 -1.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8634 4.2317 2.1472 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0088 1.5642 1.2461 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1531 2.4612 1.8398 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3526 0.0552 2.1892 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2020 1.5748 3.3528 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2184 3.3281 0.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5443 1.2301 -4.0674 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8094 1.4782 -6.5209 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7843 -1.8469 -1.2656 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3717 -1.6476 -3.1750 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1451 0.0922 -3.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1963 -1.4167 -1.6922 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4093 -0.3224 -3.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6923 -0.6637 0.4294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0621 0.8044 0.3326 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6941 1.8247 0.7586 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2602 1.6435 -0.9885 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4205 -2.0831 0.6776 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7347 -0.9607 1.1539 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0561 -0.8407 1.8744 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7335 1.0556 1.9674 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2604 2.3352 0.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8244 0.0552 2.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9676 1.7939 2.4401 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6380 -0.5526 -0.5380 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3232 0.2591 -2.7296 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4357 1.9415 -2.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6367 0.5616 -2.0009 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8425 -1.2515 1.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6322 -0.4905 2.8234 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1460 -1.2737 1.3017 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9921 1.8814 2.8938 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1557 2.5181 1.6397 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5725 -0.0502 3.2475 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1261 1.0661 -0.3155 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1000 -0.9384 -1.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3540 -1.8367 0.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4485 -1.3636 -0.5184 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1876 -1.9698 -1.7092 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2718 -0.2453 -1.2645 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4906 -3.4928 -0.2490 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6097 -3.2324 1.2865 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4511 -3.0636 1.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3791 0.3478 1.0802 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8233 -1.2528 1.8733 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3035 -1.3579 2.4595 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1534 -0.0528 3.3641 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2791 2.2131 2.6421 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1993 1.3754 4.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2444 3.1315 1.3962 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7376 3.0195 -0.3736 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9835 3.2315 0.1758 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9529 2.5350 -1.2496 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2201 1.7475 -2.8936 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5152 2.5875 -2.0761 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3018 -3.0916 -0.8443 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7233 -2.5667 2.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5213 -5.0529 0.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8709 -5.2550 2.7272 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1069 -3.0643 0.6604 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3856 -1.2401 -0.2499 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 9 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 16 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 20 23 1 0 19 24 1 0 11 25 1 0 10 26 1 0 26 27 2 0 26 28 1 0 8 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 35 37 1 0 34 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 2 0 44 45 1 0 45 46 1 1 45 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 52 54 1 0 52 55 1 0 55 56 1 0 49 57 1 6 57 58 2 0 48 59 1 0 40 60 1 6 33 61 1 6 5 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 63 66 1 0 62 67 1 0 64 3 1 0 12 7 1 0 21 14 1 0 35 30 1 0 45 40 1 0 56 49 1 0 41 33 1 0 50 44 1 0 1 68 1 0 2 69 1 0 2 70 1 0 3 71 1 1 5 72 1 1 7 73 1 1 8 74 1 1 10 75 1 6 11 76 1 1 12 77 1 6 14 78 1 6 16 79 1 6 17 80 1 0 17 81 1 0 18 82 1 0 19 83 1 1 20 84 1 6 21 85 1 1 22 86 1 0 23 87 1 0 24 88 1 0 25 89 1 0 28 90 1 0 30 91 1 1 31 92 1 0 31 93 1 0 32 94 1 0 32 95 1 0 34 96 1 1 36 97 1 0 36 98 1 0 36 99 1 0 37100 1 0 37101 1 0 37102 1 0 38103 1 0 38104 1 0 39105 1 0 39106 1 0 41107 1 1 42108 1 0 42109 1 0 43110 1 0 46111 1 0 46112 1 0 46113 1 0 47114 1 0 47115 1 0 48116 1 1 50117 1 6 51118 1 0 51119 1 0 53120 1 0 53121 1 0 53122 1 0 54123 1 0 54124 1 0 54125 1 0 55126 1 0 55127 1 0 56128 1 0 56129 1 0 57130 1 0 59131 1 0 60132 1 0 60133 1 0 60134 1 0 61135 1 0 61136 1 0 61137 1 0 62138 1 6 63139 1 1 64140 1 6 65141 1 0 66142 1 0 67143 1 0 M END

Standard InCHIKey	ULOUJZGSVBBOTQ-IUVLWTKSSA-N
Standard InCHI	InChI=1S/C48H76O19/c1-43(2)14-15-48(20-51)22(16-43)21-8-9-26-45(5)12-11-28(44(3,4)25(45)10-13-46(26,6)47(21,7)17-27(48)52)64-42-38(67-41-34(58)32(56)30(54)24(19-50)63-41)36(35(59)37(66-42)39(60)61)65-40-33(57)31(55)29(53)23(18-49)62-40/h8,20,22-38,40-42,49-50,52-59H,9-19H2,1-7H3,(H,60,61)/t22-,23+,24+,25-,26+,27-,28-,29+,30+,31-,32-,33+,34+,35-,36-,37-,38+,40-,41-,42+,45-,46+,47+,48+/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)C(=O)O)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)C[C@@H]([C@@]2([C@H]3CC(C)(C)CC2)C=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	956.5	Volume:	929.417 ? Van der Waals volume.
Dense:	1.029	LogP:	0.809 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.832 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.404 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	46.0
TPSA:	312.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.077	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.479	Fsp³:	0.917
MCE-18:	176.696 ? 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:	0.768	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.257	Promiscuous compounds:	0.054

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.288	MDCK Permeability:	-5.142
Pgp-inhibitor:	0.0	Pgp-substrate:	0.018
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):	0.375
20% Bioavailability (F20%):	0.096	30% Bioavailability (F30%):	0.938
50% Bioavailability (F50%):	0.994

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.251
Plasma Protein Binding (PPB):	66.978%	Volume Distribution (VD):	-0.506
Fu:	23.433% ? 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:	0.001
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:	0.029
HLM stability:	0.019 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

-0.104

Half-life (T1/2):

3.659

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.749	Drug-induced Liver Injury (DILI):	0.942
AMES Toxicity:	0.877	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.232	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.555	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.871	RPMI-8226 Immunitoxicity:	0.108
A549 Cytotoxicity:	0.302	Hek293 Cytotoxicity:	0.152
BCF:	0.521 ? 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:	3.298 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.795 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.775 ? 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
NPO32656	Stenocereus alamosensis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22704889]
NPO32619	isolatocereus dumortieri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22704889]
NPO32656	Stenocereus alamosensis	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO32619	isolatocereus dumortieri	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
Cell line	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
NPT521	Cell line	RBL-2H3	Rattus norvegicus	IC50	>	200000.0	nM	PMID[19318257]

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 NPC44716 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	21601
0.1-0.2	23733
0.2-0.3	3207
0.3-0.4	751
0.4-0.5	373
0.5-0.6	126
0.6-0.7	45
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9158	High Similarity	NPC160452
0.8081	Intermediate Similarity	NPC302887
0.77	Intermediate Similarity	NPC475591
0.77	Intermediate Similarity	NPC236870
0.7677	Intermediate Similarity	NPC605226
0.76	Intermediate Similarity	NPC2370
0.73	Intermediate Similarity	NPC22956
0.7273	Intermediate Similarity	NPC283417
0.7273	Intermediate Similarity	NPC200049
0.7264	Intermediate Similarity	NPC187290
0.713	Intermediate Similarity	NPC25998
0.7064	Intermediate Similarity	NPC609119
0.6923	Remote Similarity	NPC302543
0.6814	Remote Similarity	NPC602995
0.6759	Remote Similarity	NPC23275
0.6729	Remote Similarity	NPC64715
0.6724	Remote Similarity	NPC265841
0.6699	Remote Similarity	NPC603026
0.6696	Remote Similarity	NPC329828
0.661	Remote Similarity	NPC484059
0.661	Remote Similarity	NPC484060
0.6581	Remote Similarity	NPC488308
0.6577	Remote Similarity	NPC480939
0.6529	Remote Similarity	NPC484063
0.6529	Remote Similarity	NPC484064
0.6525	Remote Similarity	NPC312650
0.6509	Remote Similarity	NPC117714
0.6509	Remote Similarity	NPC30289
0.6491	Remote Similarity	NPC284449
0.6486	Remote Similarity	NPC469947
0.6486	Remote Similarity	NPC480948
0.6466	Remote Similarity	NPC47995
0.6387	Remote Similarity	NPC271610
0.6356	Remote Similarity	NPC484061
0.6356	Remote Similarity	NPC484062
0.6333	Remote Similarity	NPC476779
0.6296	Remote Similarity	NPC251768
0.6283	Remote Similarity	NPC11242
0.6262	Remote Similarity	NPC192791
0.626	Remote Similarity	NPC488309
0.6218	Remote Similarity	NPC21691
0.6195	Remote Similarity	NPC329976
0.6148	Remote Similarity	NPC110700
0.6147	Remote Similarity	NPC159309
0.6147	Remote Similarity	NPC86222
0.614	Remote Similarity	NPC605294
0.6134	Remote Similarity	NPC4749
0.6132	Remote Similarity	NPC109079
0.6075	Remote Similarity	NPC157868
0.6058	Remote Similarity	NPC1046
0.605	Remote Similarity	NPC473918
0.6019	Remote Similarity	NPC263756
0.6019	Remote Similarity	NPC213674
0.6018	Remote Similarity	NPC301449
0.6018	Remote Similarity	NPC601290
0.6016	Remote Similarity	NPC476777
0.6	Remote Similarity	NPC181066
0.5952	Remote Similarity	NPC279915
0.5948	Remote Similarity	NPC470475
0.5941	Remote Similarity	NPC31839
0.5929	Remote Similarity	NPC281148
0.5929	Remote Similarity	NPC114484
0.5926	Remote Similarity	NPC472949
0.5917	Remote Similarity	NPC277212
0.5917	Remote Similarity	NPC30279
0.5902	Remote Similarity	NPC476774
0.5902	Remote Similarity	NPC476780
0.5872	Remote Similarity	NPC76497
0.5872	Remote Similarity	NPC80843
0.5868	Remote Similarity	NPC71391
0.5856	Remote Similarity	NPC40775
0.5856	Remote Similarity	NPC10607
0.5856	Remote Similarity	NPC164389
0.5856	Remote Similarity	NPC46665
0.5854	Remote Similarity	NPC225791
0.5847	Remote Similarity	NPC478155
0.5847	Remote Similarity	NPC478154
0.5841	Remote Similarity	NPC79718
0.5827	Remote Similarity	NPC476778
0.5776	Remote Similarity	NPC104137
0.5776	Remote Similarity	NPC26626
0.5769	Remote Similarity	NPC480937
0.575	Remote Similarity	NPC470476
0.5743	Remote Similarity	NPC606107
0.5726	Remote Similarity	NPC62725
0.569	Remote Similarity	NPC80986
0.5688	Remote Similarity	NPC127056
0.5676	Remote Similarity	NPC242840
0.5669	Remote Similarity	NPC476775
0.5656	Remote Similarity	NPC46823
0.5639	Remote Similarity	NPC475368
0.561	Remote Similarity	NPC192765
0.5607	Remote Similarity	NPC164194
0.56	Remote Similarity	NPC258617
0.5596	Remote Similarity	NPC235405
0.5565	Remote Similarity	NPC470518
0.5565	Remote Similarity	NPC178264
0.5545	Remote Similarity	NPC249848
0.5545	Remote Similarity	NPC107966
0.5538	Remote Similarity	NPC476776
0.5536	Remote Similarity	NPC112352
0.5526	Remote Similarity	NPC118440
0.5495	Remote Similarity	NPC473884
0.5455	Remote Similarity	NPC123522
0.5447	Remote Similarity	NPC470218
0.5397	Remote Similarity	NPC286457
0.5391	Remote Similarity	NPC63159
0.5391	Remote Similarity	NPC235438
0.5378	Remote Similarity	NPC475486
0.537	Remote Similarity	NPC214484
0.536	Remote Similarity	NPC85154
0.5351	Remote Similarity	NPC30735
0.5345	Remote Similarity	NPC470478
0.5333	Remote Similarity	NPC480936
0.5315	Remote Similarity	NPC25605
0.531	Remote Similarity	NPC469946
0.5294	Remote Similarity	NPC187618
0.5294	Remote Similarity	NPC480473
0.5289	Remote Similarity	NPC288205
0.5289	Remote Similarity	NPC51465
0.5273	Remote Similarity	NPC48499
0.5263	Remote Similarity	NPC75417
0.5263	Remote Similarity	NPC489209
0.5254	Remote Similarity	NPC236657
0.5246	Remote Similarity	NPC475287
0.5246	Remote Similarity	NPC252657
0.5246	Remote Similarity	NPC88311
0.5234	Remote Similarity	NPC470876
0.5225	Remote Similarity	NPC603870
0.5221	Remote Similarity	NPC39211
0.5217	Remote Similarity	NPC480947
0.5217	Remote Similarity	NPC114304
0.5214	Remote Similarity	NPC222580
0.521	Remote Similarity	NPC324875
0.521	Remote Similarity	NPC292677
0.521	Remote Similarity	NPC291903
0.5203	Remote Similarity	NPC151543
0.52	Remote Similarity	NPC264566
0.52	Remote Similarity	NPC475140
0.5192	Remote Similarity	NPC204407
0.5179	Remote Similarity	NPC475516
0.5179	Remote Similarity	NPC59804
0.5172	Remote Similarity	NPC488526
0.5172	Remote Similarity	NPC485563
0.5172	Remote Similarity	NPC480475
0.5167	Remote Similarity	NPC488564
0.5164	Remote Similarity	NPC472267
0.5164	Remote Similarity	NPC107536
0.5164	Remote Similarity	NPC475119
0.5164	Remote Similarity	NPC115656
0.5164	Remote Similarity	NPC280029
0.5164	Remote Similarity	NPC9470
0.5152	Remote Similarity	NPC220160
0.5145	Remote Similarity	NPC489208
0.5141	Remote Similarity	NPC485564
0.5133	Remote Similarity	NPC114441
0.5126	Remote Similarity	NPC114692
0.512	Remote Similarity	NPC251263
0.512	Remote Similarity	NPC135904
0.5118	Remote Similarity	NPC82380
0.5118	Remote Similarity	NPC244296
0.5088	Remote Similarity	NPC488561
0.5085	Remote Similarity	NPC257468
0.5085	Remote Similarity	NPC123796
0.5085	Remote Similarity	NPC131469
0.5085	Remote Similarity	NPC297263
0.5083	Remote Similarity	NPC218954
0.507	Remote Similarity	NPC124828
0.5047	Remote Similarity	NPC286347
0.5047	Remote Similarity	NPC224121
0.5046	Remote Similarity	NPC209894
0.5044	Remote Similarity	NPC281939
0.5044	Remote Similarity	NPC56713
0.5043	Remote Similarity	NPC180550
0.5043	Remote Similarity	NPC161674
0.5043	Remote Similarity	NPC35405
0.5042	Remote Similarity	NPC95437
0.5041	Remote Similarity	NPC120116
0.5041	Remote Similarity	NPC480474
0.5041	Remote Similarity	NPC477193
0.5041	Remote Similarity	NPC478152
0.5041	Remote Similarity	NPC478151
0.5038	Remote Similarity	NPC481081

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC44716 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6705
0.1-0.2	2365
0.2-0.3	74
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