NPASS Compound

Natural Product: NPC470515

Natural Product ID	NPC470515
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Sorbifoliaside D
IUPAC Name	[(2R,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8aR,9R,10R,12aS,14aR,14bR)-9,10-dihydroxy-4,4,6a,6b,11,11,14b-heptamethyl-8a-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-4-yl] (Z)-2-methylbut-2-enoate
Synonyms	sorbifoliaside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2058430
PubChem CID	66552777
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 180188 0 0 0 0 0 0 0 0999 V2000 10.6885 2.9962 0.4321 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8007 2.1922 0.4567 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8477 1.1835 -0.6897 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8238 0.2985 -0.7112 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6232 0.6781 -1.2344 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8233 1.3786 -0.3513 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6707 0.6606 0.0411 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9111 1.5029 1.0257 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7802 0.9167 1.5340 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9835 -0.3252 2.1335 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0656 -1.3229 1.3087 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5846 -2.4456 0.9824 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0900 -2.6415 0.6258 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2156 -2.3411 1.7822 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3944 -1.1095 1.7256 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5596 -1.0645 0.4890 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4337 -1.2632 -0.6977 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8570 -0.9523 -1.8546 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4664 -0.4420 -2.0348 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0899 0.0958 -0.7959 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9445 0.3332 0.2407 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0072 1.3110 -0.1637 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4328 0.8073 1.5630 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5948 1.9155 1.4253 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6581 1.3560 0.4724 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1271 1.2102 -0.9111 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5538 2.4799 -1.5146 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1798 0.7711 -1.8731 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5565 1.3183 -1.6497 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9536 1.1624 -0.1697 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0066 1.9582 0.6700 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0679 3.4411 0.3940 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3411 1.8621 2.1414 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2615 1.1716 0.0827 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9129 -0.0463 0.1770 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8644 -0.0166 -0.8435 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7207 -1.0510 -0.9158 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1494 -0.6640 -0.7725 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6607 0.2334 -1.6678 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1185 1.5008 -1.6853 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.0642 2.4498 -1.2564 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5241 3.2711 -2.2520 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.7708 3.9777 -1.7193 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3658 4.7211 -0.5871 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9612 2.4386 -3.4554 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.7803 1.6966 -4.0357 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6194 1.7700 -3.0851 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.9010 2.9553 -3.1792 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1592 0.3495 -4.1421 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5178 3.2441 -4.4154 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3620 -2.1803 0.0375 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.1549 -1.7227 1.4341 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6714 -0.2860 1.4462 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9199 -0.0418 2.6026 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2409 -1.9264 2.2797 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0908 -2.7226 3.3997 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9557 -3.2657 3.6403 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1458 -2.9858 4.3373 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3417 -2.4740 4.1713 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7083 -1.5991 3.0289 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8930 -3.8423 5.5155 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3254 -2.9679 -0.4620 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8216 -1.6979 -0.5188 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6288 -1.9921 -1.7273 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7097 -3.4100 -2.1637 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6321 -4.4325 -1.0866 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8918 -4.0505 0.1295 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5660 -4.3159 -0.0414 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8644 -4.9716 -0.7245 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9781 -3.6863 -2.9617 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5943 -3.6739 -3.1659 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4569 -2.0603 0.6504 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1296 -0.2037 3.1266 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3949 1.2426 3.4257 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8184 1.9775 2.1538 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8214 3.3479 2.2921 O 0 0 0 0 0 0 0 0 0 0 0 0 8.3502 1.3585 4.4398 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7776 -0.9207 4.2689 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7691 1.2812 -2.5876 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8701 2.2778 -2.7129 C 0 0 2 0 0 0 0 0 0 0 0 0 12.1359 1.8594 -2.0008 C 0 0 2 0 0 0 0 0 0 0 0 0 12.8211 0.9393 -2.8087 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4916 3.5755 -2.3798 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1051 0.2143 -3.4617 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9071 3.8407 0.9024 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9115 1.6447 1.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6956 2.8480 0.3928 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7814 0.5794 -0.4619 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0598 -0.3023 -1.3998 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0861 0.5673 -0.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9570 -0.3293 0.3766 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5814 2.4167 0.4887 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0830 -0.4401 2.8339 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7433 -3.3069 1.7210 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1840 -2.8707 0.0876 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5958 -3.2690 1.9846 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8414 -2.3029 2.7163 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6555 -1.1951 2.5845 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9754 -0.2314 1.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4959 -1.0900 -2.7273 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0897 -1.3379 -2.4518 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5152 0.2547 -2.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7548 -0.7473 -0.4028 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6246 2.3477 0.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8671 1.2342 0.5641 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3253 1.3006 -1.1952 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0430 0.0320 2.1857 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2626 1.2105 2.1688 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0444 2.0242 2.4120 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1909 2.8732 1.1245 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7945 0.2890 0.8506 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3702 2.3001 -2.0912 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2512 2.9228 -2.2942 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3790 3.2906 -0.8217 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8968 0.9434 -2.9378 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2990 -0.3489 -1.8136 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5428 2.3831 -1.8793 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2514 0.8222 -2.3346 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6408 0.0679 -0.0423 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1204 3.7513 0.6024 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4671 3.9261 1.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8136 3.7545 -0.6054 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8634 2.6835 2.7260 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4440 2.1387 2.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2434 0.8738 2.5764 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2521 -0.9043 -0.0340 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6233 -1.4956 -1.9524 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3967 -0.2481 0.2533 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7666 -1.6077 -0.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2806 1.6376 -0.9359 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8350 4.0629 -2.5771 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1541 4.7174 -2.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5154 3.2311 -1.3853 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7014 5.4135 -0.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7459 1.7305 -3.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5060 2.0692 -5.0468 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8939 0.9454 -3.3035 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9754 2.7761 -2.8722 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1273 0.2672 -4.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.4634 3.4292 -4.1160 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2717 -2.8518 0.0559 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2752 -2.3062 1.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5688 0.3585 1.5627 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2063 -0.7000 2.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1238 -2.6980 4.9173 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8048 -2.1935 2.0925 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7496 -1.1915 3.1971 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0743 -0.7116 2.9291 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1926 -4.6487 5.1984 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7984 -4.3523 5.8798 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3537 -3.2951 6.3191 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6972 -3.6418 -1.0541 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3059 -0.7323 -0.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3877 -1.2794 -2.5256 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7143 -1.7057 -1.4977 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0888 -5.3360 -1.5109 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2355 -4.6992 0.9932 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1324 -4.7855 0.7122 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7884 -5.6741 -0.0598 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0692 -2.8260 -3.6873 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8830 -3.6753 -2.3307 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8526 -4.6298 -3.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5529 -2.9210 -3.9569 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6260 -3.7028 -2.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6998 -4.6911 -3.5745 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4276 -1.6658 1.2191 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1737 -2.5895 -0.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7821 -2.8961 1.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0984 -0.5995 2.7015 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4547 1.7014 3.7907 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8342 1.6366 1.9215 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8608 3.7853 1.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2150 0.9829 4.1028 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2211 -1.7793 4.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8469 1.7408 -2.9823 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1590 2.3099 -3.8063 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7830 2.7214 -1.8480 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7225 0.7430 -2.4435 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1142 4.0041 -3.1737 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4481 0.6540 -4.2673 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 13 12 1 1 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 30 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 42 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 45 50 1 0 37 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 52 55 1 0 55 56 1 0 56 57 2 0 56 58 1 0 58 59 2 0 59 60 1 0 58 61 1 0 51 62 1 0 17 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 66 69 1 0 65 70 1 0 65 71 1 0 16 72 1 1 10 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 74 77 1 0 73 78 1 0 5 79 1 0 79 80 1 0 80 81 1 0 81 82 1 0 80 83 1 0 79 84 1 0 81 3 1 0 75 8 1 0 67 13 1 0 63 13 1 0 21 16 1 0 31 25 1 0 53 35 1 0 26 20 1 0 47 40 1 0 1 85 1 0 2 86 1 0 2 87 1 0 3 88 1 1 5 89 1 6 7 90 1 0 7 91 1 0 8 92 1 6 10 93 1 1 12 94 1 0 12 95 1 0 14 96 1 0 14 97 1 0 15 98 1 0 15 99 1 0 18100 1 0 19101 1 0 19102 1 0 20103 1 1 22104 1 0 22105 1 0 22106 1 0 23107 1 0 23108 1 0 24109 1 0 24110 1 0 25111 1 1 27112 1 0 27113 1 0 27114 1 0 28115 1 0 28116 1 0 29117 1 0 29118 1 0 30119 1 1 32120 1 0 32121 1 0 32122 1 0 33123 1 0 33124 1 0 33125 1 0 35126 1 6 37127 1 6 38128 1 0 38129 1 0 40130 1 1 42131 1 6 43132 1 0 43133 1 0 44134 1 0 45135 1 1 46136 1 6 47137 1 6 48138 1 0 49139 1 0 50140 1 0 51141 1 1 52142 1 1 53143 1 6 54144 1 0 59145 1 0 60146 1 0 60147 1 0 60148 1 0 61149 1 0 61150 1 0 61151 1 0 62152 1 0 63153 1 1 64154 1 0 64155 1 0 66156 1 6 67157 1 1 68158 1 0 69159 1 0 70160 1 0 70161 1 0 70162 1 0 71163 1 0 71164 1 0 71165 1 0 72166 1 0 72167 1 0 72168 1 0 73169 1 6 74170 1 1 75171 1 6 76172 1 0 77173 1 0 78174 1 0 79175 1 6 80176 1 6 81177 1 1 82178 1 0 83179 1 0 84180 1 0 M END

Standard InCHIKey	XSQQDTHJAQSLQB-QJPROXSFSA-N
Standard InCHI	InChI=1S/C59H96O25/c1-10-25(2)49(75)84-46-38(65)31(23-77-51-43(70)40(67)36(63)29(21-61)80-51)82-53(45(46)72)83-34-14-15-56(7)32(55(34,5)6)13-16-58(9)33(56)12-11-26-27-19-54(3,4)47(73)48(74)59(27,18-17-57(26,58)8)24-78-52-44(71)41(68)37(64)30(81-52)22-76-50-42(69)39(66)35(62)28(20-60)79-50/h10-11,27-48,50-53,60-74H,12-24H2,1-9H3/b25-10-/t27-,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-,56-,57+,58+,59-/m0/s1
SMILES	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC[C@]34CC[C@@]5(C(=CC[C@H]6[C@@]5(C)CC[C@@H]5[C@]6(C)CC[C@@H](C5(C)C)O[C@@H]5O[C@H](CO[C@@H]6O[C@H](CO)[C@H]([C@@H]([C@H]6O)O)O)[C@H]([C@@H]([C@H]5O)OC(=O)/C(=CC)/C)O)[C@@H]4CC([C@H]([C@@H]3O)O)(C)C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1204.62	Volume:	1163.858 ? Van der Waals volume.
Dense:	1.035	LogP:	0.382 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.495 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.818 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	52.0
TPSA:	403.59 ? 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:	0.036	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.247	Fsp³:	0.915
MCE-18:	200.389 ? 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:	0.717	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? 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:	0.212	Promiscuous compounds:	0.157

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.413	MDCK Permeability:	-5.29
Pgp-inhibitor:	0.0	Pgp-substrate:	0.267
PAMPA:	0.999 ? 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):	0.88
20% Bioavailability (F20%):	0.898	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.07	MRP1:	0.004
Plasma Protein Binding (PPB):	61.899%	Volume Distribution (VD):	-0.295
Fu:	20.744% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.005
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:	0.999	CYP3A4-substrate:	0.765
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.048 ? 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):

-0.348

Half-life (T1/2):

4.64

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.381	Drug-induced Liver Injury (DILI):	0.665
AMES Toxicity:	0.97	Rat Oral Acute Toxicity:	0.0
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:	0.395	Drug-induced Nephrotoxicity:	0.958
Genotoxicity:	0.05	RPMI-8226 Immunitoxicity:	0.282
A549 Cytotoxicity:	0.947	Hek293 Cytotoxicity:	0.757
BCF:	1.254 ? 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:	3.68 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.382 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.391 ? 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
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	wood	n.a.	n.a.	PMID[10691716]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	husks	Inner Mongolia, China	2004-SEP	PMID[18549275]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22801644]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	Eukaryota	leaves	n.a.	n.a.	PMID[23313635]
NPO30992	Xanthoceras sorbifolia	Species	Sapindaceae	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	10

Activity Type	# Activity
Cell line	8
Non-molecular	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
NPT165	Cell line	HeLa	Homo sapiens	IC50	>	100000.0	nM	PMID[22342628]
NPT547	Cell line	BGC-823	Homo sapiens	IC50	>	100000.0	nM	PMID[22206869]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	100000.0	nM	DrugMatrix in vivo data: Biochemistry
NPT306	Cell line	PC-3	Homo sapiens	IC50	>	100000.0	nM	PMID[23317013]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	100000.0	nM	PMID[16872131]
NPT81	Cell line	A549	Homo sapiens	IC50	>	100000.0	nM	PMID[24904961]
NPT453	Cell line	HT-1080	Homo sapiens	IC50	>	100000.0	nM	PMID[22119124]
NPT1171	Cell line	HEp-2	Homo sapiens	IC50	>	100000.0	nM	PMID[18288804]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[22801644]

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 NPC470515 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	21032
0.1-0.2	23797
0.2-0.3	3726
0.3-0.4	770
0.4-0.5	447
0.5-0.6	65
0.6-0.7	3
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8529	High Similarity	NPC470911
0.83	Intermediate Similarity	NPC470516
0.7653	Intermediate Similarity	NPC470512
0.7523	Intermediate Similarity	NPC470517
0.7453	Intermediate Similarity	NPC470915
0.7353	Intermediate Similarity	NPC173859
0.7353	Intermediate Similarity	NPC148603
0.6422	Remote Similarity	NPC470514
0.6422	Remote Similarity	NPC470513
0.6408	Remote Similarity	NPC48499
0.5798	Remote Similarity	NPC79643
0.5789	Remote Similarity	NPC471435
0.5789	Remote Similarity	NPC471434
0.5752	Remote Similarity	NPC63159
0.5702	Remote Similarity	NPC123199
0.5691	Remote Similarity	NPC481080
0.5656	Remote Similarity	NPC475160
0.5656	Remote Similarity	NPC473714
0.5636	Remote Similarity	NPC173583
0.5614	Remote Similarity	NPC148417
0.5603	Remote Similarity	NPC470914
0.5586	Remote Similarity	NPC295371
0.5556	Remote Similarity	NPC481079
0.5545	Remote Similarity	NPC475516
0.5526	Remote Similarity	NPC473459
0.552	Remote Similarity	NPC476068
0.5512	Remote Similarity	NPC43550
0.55	Remote Similarity	NPC185466
0.5495	Remote Similarity	NPC473373
0.5487	Remote Similarity	NPC223301
0.5487	Remote Similarity	NPC171544
0.5472	Remote Similarity	NPC128925
0.547	Remote Similarity	NPC104372
0.5469	Remote Similarity	NPC481081
0.5463	Remote Similarity	NPC90856
0.5433	Remote Similarity	NPC41061
0.5433	Remote Similarity	NPC227551
0.5349	Remote Similarity	NPC305981
0.5312	Remote Similarity	NPC475514
0.5308	Remote Similarity	NPC261506
0.5308	Remote Similarity	NPC4328
0.5303	Remote Similarity	NPC250247
0.528	Remote Similarity	NPC470218
0.5273	Remote Similarity	NPC78046
0.5273	Remote Similarity	NPC29069
0.5267	Remote Similarity	NPC70809
0.525	Remote Similarity	NPC295823
0.525	Remote Similarity	NPC174720
0.525	Remote Similarity	NPC475467
0.5238	Remote Similarity	NPC488560
0.5231	Remote Similarity	NPC136768
0.5207	Remote Similarity	NPC481078
0.52	Remote Similarity	NPC135904
0.5182	Remote Similarity	NPC214484
0.5175	Remote Similarity	NPC39211
0.5135	Remote Similarity	NPC1046
0.513	Remote Similarity	NPC76497
0.513	Remote Similarity	NPC213674
0.513	Remote Similarity	NPC469946
0.5128	Remote Similarity	NPC159309
0.5128	Remote Similarity	NPC86222
0.512	Remote Similarity	NPC471384
0.5113	Remote Similarity	NPC220160
0.5088	Remote Similarity	NPC58448
0.5081	Remote Similarity	NPC610204
0.5079	Remote Similarity	NPC219180
0.5079	Remote Similarity	NPC603137
0.5045	Remote Similarity	NPC204458
0.5044	Remote Similarity	NPC136877
0.5043	Remote Similarity	NPC30735
0.5043	Remote Similarity	NPC309714
0.5042	Remote Similarity	NPC470913
0.5042	Remote Similarity	NPC609763
0.5038	Remote Similarity	NPC65105
0.5036	Remote Similarity	NPC33012

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC470515 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7194
0.1-0.2	1896
0.2-0.3	52
0.3-0.4	8
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