NPASS Compound

Natural Product: NPC131469

Natural Product ID	NPC131469
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-{[Alpha-L-Rhamnopyranosyl-(1->2)-Beta-D-Galactopyranosyl-(1->2)-Beta-D-Glucuronopyranosyl}-22-O-[Alpha-Lrhamnopyranosyl-(1->2)-Beta-D-Glucopyranosyl]-3Beta,22Beta,24-Trihydroxyolean-12-Ene
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,6aR,6bS,8aR,9R,12aS,14aR,14bR)-9-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL452475
PubChem CID	44566981
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 185194 0 0 0 0 0 0 0 0999 V2000 -9.7301 1.0010 4.2682 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8946 1.1080 3.1450 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6925 1.6220 1.9604 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9596 1.7930 0.8173 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8052 0.6721 0.0125 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1579 -0.2743 0.7504 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9061 -0.6315 0.1930 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7924 -0.0569 1.0021 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9038 -0.3618 2.3593 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1350 -1.7126 2.5790 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9960 -2.5704 1.3580 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8261 -2.1122 0.1808 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2828 -2.5378 -1.0295 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4988 -3.8458 1.7252 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1490 -2.1830 3.5801 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3147 -1.3836 4.0647 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1026 -3.5164 4.0262 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5566 -0.5174 0.6104 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6648 0.4812 0.2152 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7568 0.8802 1.3690 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2998 0.6863 1.1280 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9911 -0.6013 0.3915 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5988 -0.3567 -0.9774 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9709 0.1781 -1.0274 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8262 -0.6890 -1.9588 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9562 1.5136 -1.8431 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2316 1.9396 -2.0936 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2875 -1.5108 -1.9034 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2271 -1.4645 -2.1120 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9808 -1.7145 -0.7926 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4945 -0.6667 0.1359 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3465 -0.5753 1.3403 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6731 -0.1021 0.8065 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1767 -0.5921 -0.2902 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4475 -1.6232 -1.0370 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6709 -1.6954 -2.5216 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2445 -2.8795 -0.5599 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6979 -2.7101 -0.9700 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3822 -1.4651 -0.5730 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5499 -0.2034 -0.6961 C 0 0 1 0 0 0 0 0 0 0 0 0 4.6444 0.5413 -1.9499 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7699 0.2426 -2.8978 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7677 1.4243 -2.9410 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1767 0.2300 -4.3023 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4907 -1.0386 -2.7065 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7086 -1.3203 -1.2684 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3622 -0.2185 -0.7263 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4982 -0.4449 -0.0523 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3554 -0.0994 1.2772 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4627 1.2018 1.6195 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2282 1.7361 2.3616 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4397 3.0759 2.6709 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8026 2.1786 0.5499 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7761 1.6773 -0.4595 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7753 0.1787 -0.5574 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7554 -0.2464 0.3732 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7194 -1.0570 -0.1604 C 0 0 2 0 0 0 0 0 0 0 0 0 11.8669 -2.1784 0.6859 O 0 0 0 0 0 0 0 0 0 0 0 0 11.7861 -1.6859 1.9764 C 0 0 1 0 0 0 0 0 0 0 0 0 11.6842 -2.7388 3.0466 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8587 -0.7143 2.3480 C 0 0 1 0 0 0 0 0 0 0 0 0 13.1267 0.3228 1.2885 C 0 0 2 0 0 0 0 0 0 0 0 0 13.0713 -0.3325 -0.0512 C 0 0 1 0 0 0 0 0 0 0 0 0 14.0429 -1.3296 -0.1813 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4355 0.8137 1.4761 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4051 -0.0172 3.4929 O 0 0 0 0 0 0 0 0 0 0 0 0 9.5935 2.2597 -1.7129 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3627 3.3030 1.1978 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7221 -1.6207 0.9150 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6728 -3.1384 -0.4416 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5535 -1.6988 1.1932 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2005 0.3044 -0.4660 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9565 -0.1857 0.7278 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.9673 0.8610 1.8228 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.2525 0.1829 3.0222 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5642 -1.4290 1.1570 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8244 1.5239 -0.8407 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2675 1.5180 -2.1437 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.4927 2.4586 -2.8484 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5580 3.6330 -2.0814 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5286 4.6495 -2.4936 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9352 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0 0 0 0 0 0 7.8265 3.2203 3.5512 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8494 2.5766 0.1147 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7959 2.0600 -0.1337 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0923 -0.2333 -1.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6170 -1.3078 -1.2150 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8121 -1.1087 2.0388 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6229 -2.9985 3.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3244 -3.5933 2.7991 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1077 -2.2846 3.9844 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7644 -1.3081 2.6091 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3819 1.1158 1.3487 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1491 0.3297 -0.9167 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7570 -2.1554 0.2820 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0250 0.0061 1.4698 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9539 0.8327 3.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2500 1.8103 -2.3349 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7717 3.9229 0.5565 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6411 -2.2035 1.0726 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9047 -2.2313 1.3541 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6800 -0.6535 1.4360 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2108 -3.5010 0.4467 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3864 -3.3948 -0.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9648 -3.7239 -1.3772 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2371 -2.3895 0.7144 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6986 -2.2575 1.6853 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1065 -1.3547 2.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1894 -0.4216 -1.2746 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0306 -0.2910 0.3869 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8191 1.5630 1.6382 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5637 -0.7480 2.8663 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2155 -1.9762 0.4257 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0618 0.5376 -2.6065 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4343 3.3693 -0.9996 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7006 4.1470 -3.0643 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0483 5.0680 -1.5659 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9291 5.4987 -3.0779 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0411 4.6196 -3.2938 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3671 3.3610 -0.8664 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2840 1.1687 -1.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0852 1.8946 -3.7277 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.4074 4.6144 -2.4349 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1537 5.8325 -1.4897 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 11 14 1 0 10 15 1 0 15 16 2 0 15 17 1 0 8 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 6 24 26 1 0 26 27 1 0 23 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 6 35 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 42 44 1 0 42 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 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 59 60 1 0 59 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 62 65 1 0 61 66 1 0 54 67 1 0 53 68 1 0 39 69 1 1 30 70 1 1 22 71 1 1 5 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 73 76 1 0 72 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 80 81 1 0 80 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 83 86 1 0 82 87 1 0 74 3 1 0 84 78 1 0 12 7 1 0 24 19 1 0 35 30 1 0 46 39 1 0 55 48 1 0 63 57 1 0 31 22 1 0 40 34 1 0 1 88 1 0 2 89 1 0 2 90 1 0 3 91 1 1 5 92 1 6 7 93 1 6 8 94 1 1 10 95 1 1 11 96 1 6 12 97 1 1 13 98 1 0 14 99 1 0 17100 1 0 19101 1 6 20102 1 0 20103 1 0 21104 1 0 21105 1 0 23106 1 6 25107 1 0 25108 1 0 25109 1 0 26110 1 0 26111 1 0 27112 1 0 28113 1 0 28114 1 0 29115 1 0 29116 1 0 31117 1 6 32118 1 0 32119 1 0 33120 1 0 36121 1 0 36122 1 0 36123 1 0 37124 1 0 37125 1 0 38126 1 0 38127 1 0 40128 1 1 41129 1 0 41130 1 0 43131 1 0 43132 1 0 43133 1 0 44134 1 0 44135 1 0 44136 1 0 45137 1 0 45138 1 0 46139 1 6 48140 1 1 50141 1 1 51142 1 0 51143 1 0 52144 1 0 53145 1 6 54146 1 1 55147 1 6 57148 1 6 59149 1 6 60150 1 0 60151 1 0 60152 1 0 61153 1 1 62154 1 6 63155 1 6 64156 1 0 65157 1 0 66158 1 0 67159 1 0 68160 1 0 69161 1 0 69162 1 0 69163 1 0 70164 1 0 70165 1 0 70166 1 0 71167 1 0 71168 1 0 71169 1 0 72170 1 6 73171 1 6 74172 1 6 75173 1 0 76174 1 0 78175 1 6 80176 1 1 81177 1 0 81178 1 0 81179 1 0 82180 1 6 83181 1 1 84182 1 1 85183 1 0 86184 1 0 87185 1 0 M END

Standard InCHIKey	GMIGRWUYBKCOSQ-XSNMUVEOSA-N
Standard InCHI	InChI=1S/C60H98O27/c1-23-33(64)37(68)43(74)50(78-23)85-46-39(70)35(66)27(20-61)80-52(46)83-32-19-55(3,4)18-26-25-10-11-30-57(6)14-13-31(58(7,22-63)29(57)12-15-60(30,9)59(25,8)17-16-56(26,32)5)82-54-48(42(73)41(72)45(84-54)49(76)77)87-53-47(40(71)36(67)28(21-62)81-53)86-51-44(75)38(69)34(65)24(2)79-51/h10,23-24,26-48,50-54,61-75H,11-22H2,1-9H3,(H,76,77)/t23-,24-,26-,27+,28+,29+,30+,31-,32+,33-,34-,35+,36-,37+,38+,39-,40-,41-,42-,43+,44+,45-,46+,47+,48+,50-,51-,52-,53-,54+,56+,57-,58-,59+,60+/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@@H](O[C@@H]([C@H]([C@@H]2O)O)C(=O)O)O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]2([C@@H]3CC=C3[C@@]2(C)CC[C@@]2([C@H]3CC(C)(C)C[C@H]2O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O[C@@H]2O[C@@H](C)[C@@H]([C@H]([C@H]2O)O)O)O)O)C)C)C)[C@@H]([C@H]([C@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1250.63	Volume:	1192.814 ? Van der Waals volume.
Dense:	1.048	LogP:	-0.307 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.982 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.169 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	57.0
TPSA:	433.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	27.0
H-Bond Donor:	16.0	Rings:	10.0
Heavy Atoms:	27.0

MedChem Properties

QED Drug-Likeness Score:	0.063	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.344	Fsp³:	0.95
MCE-18:	221.538 ? 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:	0.688	Fluc inhibitor:	0.043 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? 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:	0.438	Promiscuous compounds:	0.155

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.573	MDCK Permeability:	-5.036
Pgp-inhibitor:	0.0	Pgp-substrate:	0.193
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):	0.997
20% Bioavailability (F20%):	0.958	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.228
Plasma Protein Binding (PPB):	62.52%	Volume Distribution (VD):	-0.324
Fu:	21.223% ? 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:	0.001
HLM stability:	0.0 ? 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):

-0.984

Half-life (T1/2):

4.805

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.47	Drug-induced Liver Injury (DILI):	0.986
AMES Toxicity:	0.908	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.007	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.651	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.409	RPMI-8226 Immunitoxicity:	0.381
A549 Cytotoxicity:	0.937	Hek293 Cytotoxicity:	0.551
BCF:	1.067 ? 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:	3.381 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.73 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.706 ? 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
NPO32725	soybeans	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[12088420]

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
ED50	6

Activity Type	# Activity
Cell line	1
Non-molecular	5

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
NPT90	Cell line	DU-145	Homo sapiens	ED50	=	3.25	ug ml-1	PMID[16562830]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	4.1	ug ml-1	PMID[12088420]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	3.94	ug ml-1	PMID[12088420]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	2.12	ug ml-1	PMID[12088420]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	14.63	ug ml-1	PMID[12088420]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	ED50	=	24.1	ug ml-1	PMID[12088420]

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 NPC131469 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	23998
0.1-0.2	21863
0.2-0.3	2678
0.3-0.4	819
0.4-0.5	361
0.5-0.6	100
0.6-0.7	20
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.989	High Similarity	NPC95437
0.9783	High Similarity	NPC114692
0.9184	High Similarity	NPC313110
0.8586	High Similarity	NPC187618
0.8384	Intermediate Similarity	NPC236657
0.8218	Intermediate Similarity	NPC120116
0.79	Intermediate Similarity	NPC118440
0.7103	Intermediate Similarity	NPC218954
0.6765	Remote Similarity	NPC12288
0.6481	Remote Similarity	NPC251768
0.6422	Remote Similarity	NPC162574
0.6321	Remote Similarity	NPC482748
0.6273	Remote Similarity	NPC482722
0.6273	Remote Similarity	NPC471963
0.6262	Remote Similarity	NPC472949
0.625	Remote Similarity	NPC484061
0.625	Remote Similarity	NPC484062
0.6226	Remote Similarity	NPC25605
0.6098	Remote Similarity	NPC484059
0.6098	Remote Similarity	NPC484060
0.6053	Remote Similarity	NPC301449
0.6053	Remote Similarity	NPC477075
0.6053	Remote Similarity	NPC601290
0.605	Remote Similarity	NPC482736
0.605	Remote Similarity	NPC482738
0.6018	Remote Similarity	NPC64715
0.6018	Remote Similarity	NPC302887
0.6016	Remote Similarity	NPC258617
0.5963	Remote Similarity	NPC473884
0.5913	Remote Similarity	NPC486564
0.5906	Remote Similarity	NPC484063
0.5906	Remote Similarity	NPC484064
0.5847	Remote Similarity	NPC471962
0.5825	Remote Similarity	NPC224121
0.582	Remote Similarity	NPC277212
0.582	Remote Similarity	NPC30279
0.5794	Remote Similarity	NPC164194
0.5726	Remote Similarity	NPC160452
0.5714	Remote Similarity	NPC192791
0.5702	Remote Similarity	NPC139044
0.5645	Remote Similarity	NPC82380
0.5645	Remote Similarity	NPC244296
0.5641	Remote Similarity	NPC477076
0.5641	Remote Similarity	NPC477079
0.5636	Remote Similarity	NPC174679
0.5636	Remote Similarity	NPC279554
0.5636	Remote Similarity	NPC309780
0.5635	Remote Similarity	NPC225791
0.5603	Remote Similarity	NPC486563
0.5565	Remote Similarity	NPC47995
0.5526	Remote Similarity	NPC114304
0.5508	Remote Similarity	NPC23275
0.5504	Remote Similarity	NPC11577
0.5504	Remote Similarity	NPC141600
0.5495	Remote Similarity	NPC59804
0.5487	Remote Similarity	NPC475171
0.5478	Remote Similarity	NPC11551
0.5462	Remote Similarity	NPC477077
0.5462	Remote Similarity	NPC477078
0.5424	Remote Similarity	NPC114484
0.5398	Remote Similarity	NPC488561
0.5398	Remote Similarity	NPC157868
0.5385	Remote Similarity	NPC204407
0.5385	Remote Similarity	NPC475504
0.5378	Remote Similarity	NPC482735
0.5372	Remote Similarity	NPC480939
0.5366	Remote Similarity	NPC151543
0.536	Remote Similarity	NPC471550
0.5351	Remote Similarity	NPC469946
0.5345	Remote Similarity	NPC148603
0.5333	Remote Similarity	NPC57362
0.5328	Remote Similarity	NPC472267
0.5328	Remote Similarity	NPC115656
0.5317	Remote Similarity	NPC46823
0.5304	Remote Similarity	NPC242840
0.5304	Remote Similarity	NPC112352
0.5299	Remote Similarity	NPC475591
0.5299	Remote Similarity	NPC236870
0.5299	Remote Similarity	NPC471383
0.5294	Remote Similarity	NPC276093
0.5289	Remote Similarity	NPC469947
0.5289	Remote Similarity	NPC480948
0.5254	Remote Similarity	NPC257468
0.5254	Remote Similarity	NPC123796
0.525	Remote Similarity	NPC482737
0.5246	Remote Similarity	NPC480936
0.5238	Remote Similarity	NPC269484
0.5238	Remote Similarity	NPC470218
0.5238	Remote Similarity	NPC97918
0.5234	Remote Similarity	NPC470518
0.521	Remote Similarity	NPC482755
0.5207	Remote Similarity	NPC470477
0.5203	Remote Similarity	NPC107536
0.5203	Remote Similarity	NPC280029
0.5203	Remote Similarity	NPC9470
0.5194	Remote Similarity	NPC265841
0.5194	Remote Similarity	NPC476774
0.5164	Remote Similarity	NPC187290
0.5161	Remote Similarity	NPC76972
0.5161	Remote Similarity	NPC252657
0.5161	Remote Similarity	NPC88311
0.5161	Remote Similarity	NPC469782
0.5161	Remote Similarity	NPC204414
0.5133	Remote Similarity	NPC136877
0.513	Remote Similarity	NPC482751
0.5124	Remote Similarity	NPC323359
0.5124	Remote Similarity	NPC481079
0.5116	Remote Similarity	NPC21691
0.5115	Remote Similarity	NPC476779
0.5089	Remote Similarity	NPC270667
0.5088	Remote Similarity	NPC56713
0.5086	Remote Similarity	NPC22956
0.5085	Remote Similarity	NPC44716
0.5085	Remote Similarity	NPC159309
0.5085	Remote Similarity	NPC173859
0.5085	Remote Similarity	NPC480475
0.5085	Remote Similarity	NPC86222
0.5079	Remote Similarity	NPC482739
0.5079	Remote Similarity	NPC323341
0.5078	Remote Similarity	NPC252289
0.5078	Remote Similarity	NPC305793
0.5077	Remote Similarity	NPC476780
0.5043	Remote Similarity	NPC127056
0.5043	Remote Similarity	NPC482741
0.5043	Remote Similarity	NPC482745
0.5043	Remote Similarity	NPC482743
0.5043	Remote Similarity	NPC146753
0.5041	Remote Similarity	NPC482740

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC131469 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7042
0.1-0.2	2051
0.2-0.3	50
0.3-0.4	5
0.4-0.5	2
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