NPASS Compound

Natural Product: NPC30735

Natural Product ID	NPC30735
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Stipuleanoside R2 Methyl Ester
IUPAC Name	methyl (2S,3S,4R,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-4,4,6a,6b,11,11,14b-heptamethyl-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-[(2R,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylate
Synonyms	stipuleanoside R2 methyl ester
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1288835
PubChem CID	52945762
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 163171 0 0 0 0 0 0 0 0999 V2000 -7.2762 -4.5774 0.8754 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6220 -3.0828 0.7768 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0241 -2.9578 1.3299 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5430 -2.7361 -0.6869 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8601 -1.3003 -0.8895 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2327 -0.3560 0.0883 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6569 0.8037 -0.6625 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3636 0.5974 -1.3367 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3710 -0.3003 -0.6979 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0557 -1.4405 -1.6431 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8365 -0.8695 0.5894 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9116 -1.3586 1.4260 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4700 -1.3910 1.1961 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0747 -0.5679 0.0380 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6415 -0.0423 0.1197 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4354 0.9111 1.2357 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2637 -1.2455 0.3664 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1239 -1.5793 -0.7977 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0159 -0.4092 -1.2225 C 0 0 1 0 0 0 0 0 0 0 0 0 1.1492 0.7772 -1.4813 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6077 2.0402 -0.8472 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2224 1.0080 -3.0063 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3195 0.4564 -1.2372 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2329 1.5087 -1.7718 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6563 1.3860 -1.4402 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0732 0.4614 -0.3473 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4620 1.3316 0.8489 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9539 -0.2719 -0.2264 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2418 -0.6859 -0.5725 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1778 0.4576 -0.2989 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6289 0.1106 -0.5704 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8962 -1.0511 0.3544 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9157 -2.1333 -0.1462 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2872 -3.4831 0.2648 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5881 -4.2498 0.9783 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5102 -3.9898 -0.1549 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9836 -5.2722 0.1693 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6246 -1.7539 0.2921 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1555 -1.5288 0.4199 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5748 -1.4865 1.7694 C 0 0 2 0 0 0 0 0 0 0 0 0 9.7604 -0.5889 1.9827 C 0 0 1 0 0 0 0 0 0 0 0 0 10.4423 -1.2943 3.1429 C 0 0 2 0 0 0 0 0 0 0 0 0 10.0041 -2.7205 3.0015 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0332 -3.5411 2.2198 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2523 -3.5953 2.8900 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8532 -2.7245 2.2711 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9452 -0.8159 4.3749 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5705 -0.4750 0.8841 O 0 0 0 0 0 0 0 0 0 0 0 0 7.3694 1.2221 -0.3966 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0734 1.6905 -1.4955 C 0 0 1 0 0 0 0 0 0 0 0 0 7.8010 3.0942 -1.8956 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9946 3.6175 -2.7130 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2176 3.7204 -1.8541 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1833 2.5662 -0.8922 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9891 3.0460 0.5234 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8183 4.1653 0.7770 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4001 1.5238 -1.1758 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3877 3.8150 -2.5843 O 0 0 0 0 0 0 0 0 0 0 0 0 8.6432 4.8299 -3.2975 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7271 3.2577 -2.7776 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8645 1.5606 -1.0897 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2606 -0.9512 1.0256 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5837 -2.3325 1.5128 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3634 0.2361 0.9010 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3893 0.1115 2.1540 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4064 0.9303 0.3228 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4713 1.4916 1.0886 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.5059 2.9802 0.9724 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.5274 3.4452 -0.0127 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.7047 2.3664 -1.0570 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.2471 1.1425 -0.3723 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.2355 -0.0879 -1.2667 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8165 0.1929 -2.5035 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.6770 0.8626 0.8374 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.6366 2.8765 -1.9848 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0409 4.5810 -0.6516 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6601 3.6153 2.2207 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2034 -4.6464 0.5728 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4377 -4.9543 1.8992 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8467 -5.1210 0.0993 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5518 -3.9452 1.3940 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6525 -2.3471 0.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0324 -2.5552 2.3618 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5718 -3.0716 -1.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3184 -3.3616 -1.1989 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9756 -1.2011 -0.9225 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5466 -1.0394 -1.9435 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6943 1.6974 0.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4277 1.0574 -1.4538 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9185 1.6257 -1.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5573 0.2757 -2.4046 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3071 -1.2103 -2.3963 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7343 -2.3446 -1.0903 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9753 -1.7283 -2.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2744 -1.7762 2.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2276 -2.4959 1.0488 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9746 -1.1599 2.1616 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0175 -1.2892 -0.8396 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7400 0.4163 2.1819 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8763 1.9005 1.0969 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6544 1.0702 1.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9564 -1.0583 1.2340 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2919 -2.1580 0.6436 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6279 -2.0748 -1.6485 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8580 -2.3556 -0.4243 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5499 -0.8049 -2.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3780 1.8608 -0.0393 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8577 2.6736 -0.3826 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1630 2.7115 -1.5700 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3057 0.9677 -3.2529 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7407 0.1671 -3.5473 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8536 1.9968 -3.2903 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4966 -0.4361 -1.9200 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0965 1.5771 -2.8960 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8579 2.4940 -1.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2021 1.0293 -2.3671 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0936 2.4194 -1.2778 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1766 2.4110 0.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5557 1.3711 1.0192 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0089 1.0276 1.7870 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3319 -1.0281 -1.6121 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0562 0.8146 0.7561 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6376 -0.2870 -1.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5048 -0.7303 1.3640 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8973 -2.0309 -1.2497 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1399 -5.4414 1.2343 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9275 -5.4418 -0.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2515 -6.0131 -0.2283 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7536 -1.0631 2.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4590 0.4064 2.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5214 -1.1490 3.1715 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8835 -3.2056 4.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5804 -4.5451 2.0849 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1298 -3.0087 1.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7966 -4.2717 2.4162 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0783 -1.5113 5.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5065 -0.3240 1.2049 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9053 0.9916 -2.3847 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5989 3.7241 -1.0331 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2203 2.9103 -3.5447 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1305 4.6538 -1.2610 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2609 2.1730 -0.8981 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9626 3.1880 0.8375 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4067 2.2328 1.1894 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3195 4.7148 1.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8850 2.9643 -2.4592 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7924 4.7602 -3.7900 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6336 2.4782 -3.3600 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9598 2.4123 -0.5937 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2800 -0.2998 1.9588 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6341 -2.9409 1.4637 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8513 -2.3689 2.6097 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2440 1.2487 2.1694 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4943 3.3213 0.6133 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4682 3.6411 0.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7427 2.1503 -1.5186 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3418 1.3534 -0.1911 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2373 -0.5202 -1.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8903 -0.8534 -0.7919 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6921 0.6234 -2.3139 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.4187 3.2578 -1.5345 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7875 5.2969 0.0101 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3588 4.5584 2.1529 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 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 6 9 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 1 15 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 20 22 1 0 20 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 1 19 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 1 0 34 35 2 0 34 36 1 0 36 37 1 0 33 38 1 0 32 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 31 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 54 57 1 0 53 58 1 0 52 59 1 0 51 60 1 0 30 61 1 0 11 62 1 0 62 63 1 0 6 64 1 1 64 65 2 0 64 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 72 73 1 0 71 74 1 0 70 75 1 0 69 76 1 0 68 77 1 0 63 2 1 0 74 67 1 0 62 6 1 0 26 9 1 0 38 29 1 0 46 40 1 0 57 50 1 0 26 14 1 0 23 15 1 0 1 78 1 0 1 79 1 0 1 80 1 0 3 81 1 0 3 82 1 0 3 83 1 0 4 84 1 0 4 85 1 0 5 86 1 0 5 87 1 0 7 88 1 0 7 89 1 0 8 90 1 0 8 91 1 0 10 92 1 0 10 93 1 0 10 94 1 0 12 95 1 0 13 96 1 0 13 97 1 0 14 98 1 6 16 99 1 0 16100 1 0 16101 1 0 17102 1 0 17103 1 0 18104 1 0 18105 1 0 19106 1 6 21107 1 0 21108 1 0 21109 1 0 22110 1 0 22111 1 0 22112 1 0 23113 1 6 24114 1 0 24115 1 0 25116 1 0 25117 1 0 27118 1 0 27119 1 0 27120 1 0 29121 1 6 30122 1 1 31123 1 6 32124 1 1 33125 1 6 37126 1 0 37127 1 0 37128 1 0 40129 1 1 41130 1 1 42131 1 1 43132 1 1 44133 1 0 44134 1 0 45135 1 0 47136 1 0 48137 1 0 50138 1 6 51139 1 1 52140 1 6 53141 1 1 54142 1 1 55143 1 0 55144 1 0 56145 1 0 58146 1 0 59147 1 0 60148 1 0 61149 1 0 62150 1 1 63151 1 0 63152 1 0 67153 1 1 68154 1 6 69155 1 1 70156 1 6 71157 1 1 72158 1 0 72159 1 0 73160 1 0 75161 1 0 76162 1 0 77163 1 0 M END

Standard InCHIKey	IEWLKNYJNWFEKE-KPUFRCRSSA-N
Standard InCHI	InChI=1S/C54H86O23/c1-49(2)15-17-54(48(68)77-46-38(65)35(62)32(59)26(21-56)72-46)18-16-52(6)23(24(54)19-49)9-10-29-51(5)13-12-30(50(3,4)28(51)11-14-53(29,52)7)73-47-39(66)40(74-45-37(64)34(61)31(58)25(20-55)70-45)41(42(76-47)43(67)69-8)75-44-36(63)33(60)27(22-57)71-44/h9,24-42,44-47,55-66H,10-22H2,1-8H3/t24-,25+,26+,27-,28-,29+,30-,31+,32+,33-,34-,35-,36+,37+,38+,39+,40+,41-,42-,44+,45-,46-,47+,51-,52+,53+,54-/m0/s1
SMILES	CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](C(=O)OC)O3)O[C@@H]3[C@@H]([C@H]([C@H](CO)O3)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O)[C@@H]2C1)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)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
NPO1994	Panax stipuleanatus	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20951582]
NPO1994	Panax stipuleanatus	Species	Araliaceae	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	2

Activity Type	# Activity
Cell line	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
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	67080.0	nM	PMID[17254669]
NPT393	Cell line	HCT-116	Homo sapiens	IC50	>	100000.0	nM	PMID[25927586]

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 NPC30735 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	20714
0.1-0.2	24558
0.2-0.3	3308
0.3-0.4	728
0.4-0.5	349
0.5-0.6	115
0.6-0.7	59
0.7-0.8	0
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8889	High Similarity	NPC249848
0.8889	High Similarity	NPC107966
0.837	Intermediate Similarity	NPC235405
0.8132	Intermediate Similarity	NPC214484
0.7835	Intermediate Similarity	NPC223301
0.7835	Intermediate Similarity	NPC171544
0.7778	Intermediate Similarity	NPC235438
0.7723	Intermediate Similarity	NPC281148
0.7579	Intermediate Similarity	NPC48499
0.75	Intermediate Similarity	NPC10607
0.7423	Intermediate Similarity	NPC475516
0.7327	Intermediate Similarity	NPC40775
0.7273	Intermediate Similarity	NPC39211
0.7157	Intermediate Similarity	NPC159309
0.7157	Intermediate Similarity	NPC86222
0.71	Intermediate Similarity	NPC157868
0.7087	Intermediate Similarity	NPC475591
0.7087	Intermediate Similarity	NPC236870
0.7048	Intermediate Similarity	NPC104372
0.7019	Intermediate Similarity	NPC297263
0.699	Remote Similarity	NPC251768
0.699	Remote Similarity	NPC46665
0.6961	Remote Similarity	NPC192791
0.6961	Remote Similarity	NPC112352
0.6887	Remote Similarity	NPC114484
0.6863	Remote Similarity	NPC469946
0.6857	Remote Similarity	NPC222580
0.6762	Remote Similarity	NPC63159
0.6759	Remote Similarity	NPC80986
0.6726	Remote Similarity	NPC475160
0.6726	Remote Similarity	NPC473714
0.6702	Remote Similarity	NPC237503
0.6697	Remote Similarity	NPC187290
0.6667	Remote Similarity	NPC90856
0.6667	Remote Similarity	NPC167383
0.6667	Remote Similarity	NPC473373
0.6609	Remote Similarity	NPC481080
0.6606	Remote Similarity	NPC295823
0.6606	Remote Similarity	NPC174720
0.6606	Remote Similarity	NPC475467
0.6552	Remote Similarity	NPC476068
0.6518	Remote Similarity	NPC475287
0.6514	Remote Similarity	NPC301449
0.6514	Remote Similarity	NPC601290
0.6491	Remote Similarity	NPC135904
0.6442	Remote Similarity	NPC295371
0.6442	Remote Similarity	NPC473884
0.6435	Remote Similarity	NPC470218
0.6396	Remote Similarity	NPC31838
0.6396	Remote Similarity	NPC481078
0.6364	Remote Similarity	NPC481079
0.6364	Remote Similarity	NPC128925
0.6321	Remote Similarity	NPC242840
0.6316	Remote Similarity	NPC79643
0.6303	Remote Similarity	NPC41061
0.6303	Remote Similarity	NPC227551
0.6303	Remote Similarity	NPC258617
0.63	Remote Similarity	NPC209894
0.6275	Remote Similarity	NPC29069
0.625	Remote Similarity	NPC43550
0.6239	Remote Similarity	NPC488560
0.6228	Remote Similarity	NPC60557
0.6228	Remote Similarity	NPC67857
0.6204	Remote Similarity	NPC480475
0.6198	Remote Similarity	NPC305981
0.6198	Remote Similarity	NPC481081
0.619	Remote Similarity	NPC150400
0.6148	Remote Similarity	NPC261506
0.6148	Remote Similarity	NPC4328
0.6147	Remote Similarity	NPC148417
0.6117	Remote Similarity	NPC1046
0.6111	Remote Similarity	NPC309714
0.6068	Remote Similarity	NPC123199
0.6038	Remote Similarity	NPC58448
0.6034	Remote Similarity	NPC192600
0.6019	Remote Similarity	NPC204458
0.6018	Remote Similarity	NPC241909
0.6	Remote Similarity	NPC250247
0.6	Remote Similarity	NPC57484
0.5962	Remote Similarity	NPC78046
0.5946	Remote Similarity	NPC475504
0.5926	Remote Similarity	NPC473343
0.5926	Remote Similarity	NPC161674
0.5882	Remote Similarity	NPC100639
0.5872	Remote Similarity	NPC75417
0.584	Remote Similarity	NPC70809
0.5818	Remote Similarity	NPC104071
0.5806	Remote Similarity	NPC236638
0.5806	Remote Similarity	NPC294453
0.58	Remote Similarity	NPC306746
0.58	Remote Similarity	NPC199457
0.578	Remote Similarity	NPC263756
0.578	Remote Similarity	NPC213674
0.5766	Remote Similarity	NPC102439
0.5766	Remote Similarity	NPC473459
0.5766	Remote Similarity	NPC2370
0.5763	Remote Similarity	NPC123522
0.5752	Remote Similarity	NPC64715
0.5743	Remote Similarity	NPC68419
0.5739	Remote Similarity	NPC480473
0.5739	Remote Similarity	NPC480474
0.5728	Remote Similarity	NPC256798
0.5726	Remote Similarity	NPC65105
0.5714	Remote Similarity	NPC68175
0.5691	Remote Similarity	NPC286457
0.569	Remote Similarity	NPC104137
0.569	Remote Similarity	NPC26626
0.5678	Remote Similarity	NPC76972
0.5678	Remote Similarity	NPC469782
0.5678	Remote Similarity	NPC204414
0.5676	Remote Similarity	NPC109588
0.5676	Remote Similarity	NPC160415
0.5648	Remote Similarity	NPC139894
0.5636	Remote Similarity	NPC76497
0.5635	Remote Similarity	NPC298034
0.5635	Remote Similarity	NPC71065
0.5625	Remote Similarity	NPC164389
0.562	Remote Similarity	NPC471550
0.5612	Remote Similarity	NPC191763
0.56	Remote Similarity	NPC293330
0.5537	Remote Similarity	NPC155410
0.552	Remote Similarity	NPC475514
0.5508	Remote Similarity	NPC11242
0.5496	Remote Similarity	NPC480422
0.5495	Remote Similarity	NPC162107
0.5495	Remote Similarity	NPC46912
0.5487	Remote Similarity	NPC11551
0.5487	Remote Similarity	NPC180550
0.5487	Remote Similarity	NPC35405
0.5455	Remote Similarity	NPC173583
0.5446	Remote Similarity	NPC478066
0.5437	Remote Similarity	NPC604133
0.5421	Remote Similarity	NPC189884
0.5421	Remote Similarity	NPC138334
0.5403	Remote Similarity	NPC85154
0.5392	Remote Similarity	NPC116794
0.5391	Remote Similarity	NPC31193
0.5391	Remote Similarity	NPC609763
0.5366	Remote Similarity	NPC283417
0.5366	Remote Similarity	NPC200049
0.536	Remote Similarity	NPC21691
0.5351	Remote Similarity	NPC44716
0.534	Remote Similarity	NPC37739
0.534	Remote Similarity	NPC606107
0.5333	Remote Similarity	NPC475368
0.5328	Remote Similarity	NPC165204
0.5327	Remote Similarity	NPC47063
0.5312	Remote Similarity	NPC202828
0.5312	Remote Similarity	NPC119592
0.5308	Remote Similarity	NPC224381
0.5303	Remote Similarity	NPC489209
0.5294	Remote Similarity	NPC46388
0.5294	Remote Similarity	NPC36831
0.5294	Remote Similarity	NPC605954
0.5288	Remote Similarity	NPC137917
0.528	Remote Similarity	NPC4749
0.5278	Remote Similarity	NPC473481
0.5278	Remote Similarity	NPC269095
0.5271	Remote Similarity	NPC302543
0.5263	Remote Similarity	NPC117714
0.5263	Remote Similarity	NPC30289
0.5221	Remote Similarity	NPC475171
0.521	Remote Similarity	NPC96641
0.521	Remote Similarity	NPC481030
0.521	Remote Similarity	NPC163183
0.5197	Remote Similarity	NPC473452
0.5197	Remote Similarity	NPC480418
0.5194	Remote Similarity	NPC136768
0.5191	Remote Similarity	NPC220160
0.5185	Remote Similarity	NPC161434
0.5177	Remote Similarity	NPC45606
0.5133	Remote Similarity	NPC470512
0.5124	Remote Similarity	NPC75287
0.512	Remote Similarity	NPC191827
0.5098	Remote Similarity	NPC473844
0.5094	Remote Similarity	NPC271138
0.5094	Remote Similarity	NPC31839
0.5094	Remote Similarity	NPC110139
0.5094	Remote Similarity	NPC108709
0.5089	Remote Similarity	NPC108748
0.5088	Remote Similarity	NPC471547
0.5086	Remote Similarity	NPC488526
0.5085	Remote Similarity	NPC302887
0.5083	Remote Similarity	NPC160452
0.5078	Remote Similarity	NPC110633
0.5067	Remote Similarity	NPC469778
0.5054	Remote Similarity	NPC246708
0.5047	Remote Similarity	NPC220984
0.5045	Remote Similarity	NPC475208
0.5043	Remote Similarity	NPC258885
0.5043	Remote Similarity	NPC470515
0.5041	Remote Similarity	NPC268184
0.5039	Remote Similarity	NPC470876
0.5035	Remote Similarity	NPC220838

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC30735 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7442
0.1-0.2	1644
0.2-0.3	59
0.3-0.4	4
0.4-0.5	1
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