NPASS Compound

Natural Product: NPC302543

Natural Product ID	NPC302543
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gordonoside P
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8-hydroxy-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]-5-[(2S,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms	gordonoside P
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1782849
PubChem CID	54585161
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 181190 0 0 0 0 0 0 0 0999 V2000 -9.4157 -0.3432 3.1808 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1177 -0.5646 2.6649 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6681 0.7651 2.1004 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4194 0.7460 1.5452 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3199 0.2783 0.2562 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1491 -1.0927 0.2827 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9670 -1.5011 -0.3224 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0784 -2.3653 0.5238 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0970 -3.7133 0.0572 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4164 -4.1625 0.1585 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2855 -3.4594 -0.8619 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4114 -2.3719 -1.5047 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3017 -3.0113 -2.0032 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0835 -2.8314 -3.3602 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1290 -4.0531 -4.0538 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1067 -4.9012 -3.6220 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7583 -4.4523 -4.1623 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9598 -3.0160 -4.6702 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.6951 -2.2867 -3.5662 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7012 -0.9281 -3.8818 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7139 -2.3867 -4.8064 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3972 -5.2935 -5.2267 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3727 -2.8175 -0.2755 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4946 -5.6374 0.0115 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4295 -6.2703 -0.1766 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6772 -6.3490 0.0713 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7875 -1.8525 0.3909 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1177 -1.6242 1.5565 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9020 -2.5242 1.6082 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0507 -2.2594 0.4666 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4749 -0.7795 0.3901 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1602 -0.1230 1.5637 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6089 -0.2125 1.7510 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8446 0.0669 3.2592 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4902 0.7507 1.0431 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4027 1.2755 1.6486 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8988 1.1953 1.9717 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6728 0.4846 0.8528 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9416 -0.7470 0.5437 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5562 -1.3576 -0.6974 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9320 -1.6988 -0.2526 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6439 -1.0655 0.6478 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0665 0.1187 1.3259 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0530 -0.0183 2.8337 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1064 1.1876 1.0508 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3096 0.7226 0.3251 C 0 0 2 0 0 0 0 0 0 0 0 0 7.0387 -0.4788 0.9013 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0195 -1.5849 0.9064 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0909 -2.5934 1.9967 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3472 -2.5496 2.8175 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4917 -3.2838 2.1127 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0517 -3.3450 4.0915 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8177 -1.2098 3.2123 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7514 -0.1859 2.1543 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1192 -0.6919 -0.1219 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2490 -1.7473 -0.7727 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0023 0.3434 -0.3376 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0551 0.2611 -1.2744 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2970 0.2875 -0.6757 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6962 1.5077 -0.1939 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9470 1.4854 1.3039 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9496 0.5467 1.5390 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8032 2.6417 -0.6110 C 0 0 2 0 0 0 0 0 0 0 0 0 10.6771 2.5319 -2.1378 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8655 1.2644 -2.3653 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3382 0.7173 -3.5689 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0747 3.6687 -2.6217 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4229 3.8606 -0.3571 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2372 1.7619 0.3179 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7867 1.4915 -0.2358 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0310 -0.2902 -0.9426 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4724 0.7206 -0.6452 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0287 1.9614 0.0121 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.7397 1.4263 1.2645 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.4422 2.3985 1.9227 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8199 2.7446 -0.7732 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4190 4.0677 -0.8668 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3475 4.9376 -0.3009 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8503 5.8630 -1.1838 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0101 6.6109 -0.6038 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7713 6.8392 -1.6459 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.6703 6.0017 -2.2266 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.9954 4.5068 -2.2285 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7643 3.8902 -2.5597 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5175 6.2195 -1.4554 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2725 7.7338 -2.5762 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0557 0.8969 -1.9369 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4193 0.4025 3.8219 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1410 -1.3505 1.9141 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4214 -0.8340 3.4642 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5748 1.4337 3.0143 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4251 0.7923 -0.2121 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4245 -0.5967 -0.7105 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3297 -2.4446 1.5767 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7354 -3.9515 1.2117 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6881 -4.1426 -1.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9852 -1.7921 -2.2400 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8756 -2.1907 -3.7936 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0575 -4.9521 -2.5135 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3494 -5.9180 -3.9844 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9603 -4.5060 -3.4111 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4753 -2.9983 -5.6407 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1045 -2.4622 -2.6458 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7870 -0.6950 -4.1628 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0610 -2.7276 -4.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7021 -5.9664 -4.9353 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1457 -2.7302 -0.8731 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7983 -7.3162 -0.2003 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7894 -1.9421 2.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4088 -2.5378 2.6008 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2890 -3.5625 1.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4386 -2.6083 -0.4494 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9191 -2.9295 0.6329 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3136 -0.6398 2.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8163 -0.4077 3.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0090 -0.3152 3.8534 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9591 1.1490 3.4429 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5582 0.5237 1.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4900 0.6010 -0.0515 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3487 1.8045 1.3324 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0567 1.7368 2.5487 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1699 1.9175 0.8088 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1801 2.2584 2.0744 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9039 0.6089 2.9101 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1810 -1.4783 1.3789 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6973 -0.6277 -1.5247 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0007 -2.2006 -1.1013 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3511 -2.5867 -0.7669 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3535 -0.7864 3.2139 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0587 -0.3216 3.2237 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8318 0.8906 3.3760 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4917 1.6584 2.0074 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7305 2.0547 0.4758 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0745 0.4821 -0.7292 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3477 -2.1968 -0.0056 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0857 -3.6742 1.6267 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1632 -2.6240 2.6479 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9010 -4.1076 2.7336 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2767 -2.5490 1.7996 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1494 -3.7479 1.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8356 -3.2043 4.8486 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0417 -3.1019 4.4391 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0563 -4.4158 3.7804 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2114 -0.8974 4.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8462 -1.3396 3.6402 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2770 0.7469 2.5924 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8181 0.1676 1.9911 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9808 -0.7642 -1.7491 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7053 1.7194 -0.6555 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0078 1.2492 1.8590 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3534 2.4761 1.6232 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3748 0.2754 0.7106 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8042 2.6065 -0.1723 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7208 2.4008 -2.5354 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8210 1.5480 -2.5225 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2548 1.4180 -4.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4445 4.4529 -2.1085 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4455 4.0591 0.6155 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0844 2.3772 -0.4291 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8106 2.5090 0.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5805 1.2938 -0.9794 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8609 1.5585 -0.8865 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7364 -0.5363 -1.7041 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9240 -0.8812 -1.3113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3396 0.7471 -0.9858 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2517 -0.0719 -0.6407 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1460 2.5208 0.4420 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4468 0.6165 0.9243 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4030 2.1663 1.9179 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4925 4.1385 -0.2207 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2298 5.3636 -2.1159 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8632 6.7020 -1.3355 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7374 7.6441 -0.3099 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4547 6.1339 0.2976 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4295 7.4062 -0.7303 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5119 6.3301 -3.2818 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7453 4.3268 -3.0149 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5028 4.3228 -3.4339 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7493 6.4586 -0.5094 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2475 8.6770 -2.2697 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1071 1.1563 -1.9874 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 18 19 1 0 19 20 1 0 18 21 1 0 17 22 1 0 11 23 1 0 10 24 1 0 24 25 2 0 24 26 1 0 8 27 1 0 27 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 33 35 1 0 32 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 2 0 42 43 1 0 43 44 1 1 43 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 50 52 1 0 50 53 1 0 53 54 1 0 47 55 1 6 55 56 2 0 55 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 60 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 64 67 1 0 63 68 1 0 46 69 1 0 38 70 1 6 31 71 1 6 5 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 73 76 1 0 76 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 79 81 1 0 81 82 1 0 82 83 1 0 83 84 1 0 82 85 1 0 81 86 1 0 72 87 1 0 74 3 1 0 83 77 1 0 12 7 1 0 19 14 1 0 33 28 1 0 43 38 1 0 54 47 1 0 65 58 1 0 39 31 1 0 48 42 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 6 14 98 1 6 16 99 1 0 16100 1 0 17101 1 1 18102 1 6 19103 1 1 20104 1 0 21105 1 0 22106 1 0 23107 1 0 26108 1 0 28109 1 1 29110 1 0 29111 1 0 30112 1 0 30113 1 0 32114 1 1 34115 1 0 34116 1 0 34117 1 0 35118 1 0 35119 1 0 35120 1 0 36121 1 0 36122 1 0 37123 1 0 37124 1 0 39125 1 1 40126 1 0 40127 1 0 41128 1 0 44129 1 0 44130 1 0 44131 1 0 45132 1 0 45133 1 0 46134 1 6 48135 1 6 49136 1 0 49137 1 0 51138 1 0 51139 1 0 51140 1 0 52141 1 0 52142 1 0 52143 1 0 53144 1 0 53145 1 0 54146 1 0 54147 1 0 58148 1 6 60149 1 6 61150 1 0 61151 1 0 62152 1 0 63153 1 1 64154 1 6 65155 1 6 66156 1 0 67157 1 0 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 6 73167 1 1 74168 1 6 75169 1 0 77170 1 1 79171 1 6 80172 1 0 80173 1 0 80174 1 0 81175 1 1 82176 1 6 83177 1 6 84178 1 0 85179 1 0 86180 1 0 87181 1 0 M END

Standard InCHIKey	LPBOZSLWWLQGRY-DLZLHNPUSA-N
Standard InCHI	InChI=1S/C59H94O28/c1-22-32(64)36(68)39(71)49(79-22)83-43-35(67)27(20-61)81-51(42(43)74)86-46-44(84-48-38(70)33(65)25(62)21-78-48)41(73)45(47(75)76)85-52(46)82-31-12-13-56(6)28(55(31,4)5)11-14-57(7)29(56)10-9-23-24-17-54(2,3)15-16-59(24,30(63)18-58(23,57)8)53(77)87-50-40(72)37(69)34(66)26(19-60)80-50/h9,22,24-46,48-52,60-74H,10-21H2,1-8H3,(H,75,76)/t22-,24-,25+,26+,27+,28-,29+,30+,31-,32-,33-,34+,35+,36+,37-,38+,39+,40+,41-,42+,43-,44-,45-,46+,48-,49-,50-,51-,52+,56-,57+,58+,59+/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]2OC[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@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)C)C)[C@@H]([C@H]([C@@H]1O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1250.59	Volume:	1181.672 ? Van der Waals volume.
Dense:	1.058	LogP:	-0.481 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.077 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.608 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	58.0
TPSA:	450.12 ? Topological Polar Surface Area.	H-Bond Acceptor:	28.0
H-Bond Donor:	16.0	Rings:	10.0
Heavy Atoms:	28.0

MedChem Properties

QED Drug-Likeness Score:	0.048	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.341	Fsp³:	0.932
MCE-18:	223.158 ? 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:	0.696	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:	0.298	Promiscuous compounds:	0.132

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.691	MDCK Permeability:	-5.064
Pgp-inhibitor:	0.0	Pgp-substrate:	0.11
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):	0.936
20% Bioavailability (F20%):	0.169	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009	MRP1:	0.006
Plasma Protein Binding (PPB):	47.531%	Volume Distribution (VD):	-0.42
Fu:	35.352% ? 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:	0.483	CYP3A4-substrate:	0.97
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.839
HLM stability:	0.021 ? 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):

-1.082

Half-life (T1/2):

6.361

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.723	Drug-induced Liver Injury (DILI):	0.99
AMES Toxicity:	0.87	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.004	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.532	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	0.212	RPMI-8226 Immunitoxicity:	0.208
A549 Cytotoxicity:	0.357	Hek293 Cytotoxicity:	0.109
BCF:	0.634 ? 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:	3.433 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.11 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.934 ? 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
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	Roots	Yunnan Province, China	2005-MAY	PMID[20560647]
NPO31118	Gordonia chrysandra	Species	Theaceae	Eukaryota	n.a.	stem	n.a.	PMID[21473609]
NPO31118	Gordonia chrysandra	Species	Theaceae	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
Inhibition	1

Activity Type	# Activity
Non-molecular	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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	5.9	%	PMID[21473609]

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 NPC302543 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	23562
0.1-0.2	22296
0.2-0.3	2722
0.3-0.4	646
0.4-0.5	322
0.5-0.6	120
0.6-0.7	69
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8435	Intermediate Similarity	NPC283417
0.8435	Intermediate Similarity	NPC200049
0.7917	Intermediate Similarity	NPC21691
0.7913	Intermediate Similarity	NPC11242
0.7833	Intermediate Similarity	NPC4749
0.7521	Intermediate Similarity	NPC187290
0.7328	Intermediate Similarity	NPC64715
0.7209	Intermediate Similarity	NPC220160
0.7009	Intermediate Similarity	NPC475591
0.7009	Intermediate Similarity	NPC236870
0.6992	Remote Similarity	NPC123522
0.6953	Remote Similarity	NPC475514
0.6923	Remote Similarity	NPC44716
0.6923	Remote Similarity	NPC164389
0.6875	Remote Similarity	NPC1046
0.6875	Remote Similarity	NPC286457
0.6744	Remote Similarity	NPC265841
0.6719	Remote Similarity	NPC85154
0.6693	Remote Similarity	NPC602995
0.6692	Remote Similarity	NPC470876
0.6667	Remote Similarity	NPC104137
0.6667	Remote Similarity	NPC26626
0.6612	Remote Similarity	NPC302887
0.6585	Remote Similarity	NPC160452
0.6557	Remote Similarity	NPC114484
0.6555	Remote Similarity	NPC30289
0.6547	Remote Similarity	NPC475368
0.6532	Remote Similarity	NPC481078
0.6515	Remote Similarity	NPC484059
0.6515	Remote Similarity	NPC484060
0.6504	Remote Similarity	NPC301449
0.6504	Remote Similarity	NPC601290
0.6489	Remote Similarity	NPC488308
0.6466	Remote Similarity	NPC481081
0.6439	Remote Similarity	NPC271610
0.6439	Remote Similarity	NPC312650
0.6364	Remote Similarity	NPC473452
0.6324	Remote Similarity	NPC484063
0.6324	Remote Similarity	NPC484064
0.6304	Remote Similarity	NPC489209
0.6288	Remote Similarity	NPC484061
0.6288	Remote Similarity	NPC484062
0.6281	Remote Similarity	NPC117714
0.6281	Remote Similarity	NPC605226
0.625	Remote Similarity	NPC213674
0.6231	Remote Similarity	NPC123199
0.623	Remote Similarity	NPC159309
0.623	Remote Similarity	NPC86222
0.6214	Remote Similarity	NPC33012
0.6204	Remote Similarity	NPC488309
0.6176	Remote Similarity	NPC309223
0.6172	Remote Similarity	NPC25998
0.6159	Remote Similarity	NPC250247
0.6154	Remote Similarity	NPC284449
0.6154	Remote Similarity	NPC489208
0.6149	Remote Similarity	NPC475584
0.6149	Remote Similarity	NPC475152
0.6148	Remote Similarity	NPC476779
0.6143	Remote Similarity	NPC8524
0.6136	Remote Similarity	NPC47995
0.6133	Remote Similarity	NPC485563
0.6124	Remote Similarity	NPC609119
0.6122	Remote Similarity	NPC475394
0.6115	Remote Similarity	NPC102505
0.6115	Remote Similarity	NPC488514
0.6103	Remote Similarity	NPC236638
0.6103	Remote Similarity	NPC294453
0.6103	Remote Similarity	NPC305981
0.6098	Remote Similarity	NPC251768
0.6098	Remote Similarity	NPC46665
0.609	Remote Similarity	NPC481080
0.6077	Remote Similarity	NPC79643
0.6074	Remote Similarity	NPC258617
0.6066	Remote Similarity	NPC112352
0.6058	Remote Similarity	NPC261506
0.6058	Remote Similarity	NPC4328
0.6	Remote Similarity	NPC13998
0.6	Remote Similarity	NPC476774
0.6	Remote Similarity	NPC476780
0.5984	Remote Similarity	NPC263756
0.597	Remote Similarity	NPC71391
0.5956	Remote Similarity	NPC41061
0.5956	Remote Similarity	NPC227551
0.5926	Remote Similarity	NPC476068
0.5923	Remote Similarity	NPC470475
0.5878	Remote Similarity	NPC475287
0.587	Remote Similarity	NPC110700
0.587	Remote Similarity	NPC476777
0.5859	Remote Similarity	NPC23275
0.5854	Remote Similarity	NPC22956
0.5854	Remote Similarity	NPC469946
0.5852	Remote Similarity	NPC329828
0.584	Remote Similarity	NPC488526
0.5833	Remote Similarity	NPC475208
0.5827	Remote Similarity	NPC79718
0.5814	Remote Similarity	NPC69811
0.5809	Remote Similarity	NPC57484
0.5806	Remote Similarity	NPC192791
0.5797	Remote Similarity	NPC43550
0.5786	Remote Similarity	NPC476775
0.5781	Remote Similarity	NPC281148
0.5778	Remote Similarity	NPC277212
0.5778	Remote Similarity	NPC30279
0.5778	Remote Similarity	NPC473918
0.5778	Remote Similarity	NPC488560
0.5775	Remote Similarity	NPC476776
0.5769	Remote Similarity	NPC207738
0.5769	Remote Similarity	NPC475486
0.5746	Remote Similarity	NPC135904
0.5745	Remote Similarity	NPC482010
0.5736	Remote Similarity	NPC481079
0.5735	Remote Similarity	NPC192765
0.5725	Remote Similarity	NPC815
0.5714	Remote Similarity	NPC476991
0.5704	Remote Similarity	NPC475160
0.5704	Remote Similarity	NPC279915
0.5704	Remote Similarity	NPC473714
0.5704	Remote Similarity	NPC476778
0.5693	Remote Similarity	NPC178264
0.5692	Remote Similarity	NPC295823
0.5692	Remote Similarity	NPC174720
0.5692	Remote Similarity	NPC475467
0.568	Remote Similarity	NPC223301
0.568	Remote Similarity	NPC171544
0.5664	Remote Similarity	NPC68767
0.5664	Remote Similarity	NPC293031
0.5659	Remote Similarity	NPC104372
0.5645	Remote Similarity	NPC157868
0.5643	Remote Similarity	NPC202828
0.5643	Remote Similarity	NPC119592
0.5641	Remote Similarity	NPC23020
0.563	Remote Similarity	NPC166422
0.563	Remote Similarity	NPC470476
0.5629	Remote Similarity	NPC124828
0.5625	Remote Similarity	NPC470478
0.5625	Remote Similarity	NPC297263
0.5625	Remote Similarity	NPC51099
0.5615	Remote Similarity	NPC324875
0.5615	Remote Similarity	NPC292677
0.5612	Remote Similarity	NPC225791
0.561	Remote Similarity	NPC475516
0.5603	Remote Similarity	NPC298034
0.5603	Remote Similarity	NPC71065
0.56	Remote Similarity	NPC76497
0.5592	Remote Similarity	NPC485564
0.5591	Remote Similarity	NPC40775
0.5591	Remote Similarity	NPC10607
0.5591	Remote Similarity	NPC2370
0.5588	Remote Similarity	NPC470218
0.5573	Remote Similarity	NPC80986
0.5573	Remote Similarity	NPC477193
0.5571	Remote Similarity	NPC293330
0.5547	Remote Similarity	NPC63159
0.5547	Remote Similarity	NPC46823
0.554	Remote Similarity	NPC110633
0.5537	Remote Similarity	NPC238935
0.5532	Remote Similarity	NPC136768
0.553	Remote Similarity	NPC469947
0.553	Remote Similarity	NPC31838
0.553	Remote Similarity	NPC480948
0.5522	Remote Similarity	NPC60557
0.5522	Remote Similarity	NPC67857
0.552	Remote Similarity	NPC603026
0.5515	Remote Similarity	NPC251263
0.551	Remote Similarity	NPC275225
0.551	Remote Similarity	NPC480421
0.5507	Remote Similarity	NPC181066
0.5504	Remote Similarity	NPC475504
0.5493	Remote Similarity	NPC33068
0.5489	Remote Similarity	NPC480939
0.5468	Remote Similarity	NPC237191
0.5455	Remote Similarity	NPC187618
0.5455	Remote Similarity	NPC475892
0.5455	Remote Similarity	NPC475527
0.5449	Remote Similarity	NPC476113
0.5442	Remote Similarity	NPC485562
0.5441	Remote Similarity	NPC471384
0.544	Remote Similarity	NPC480420
0.5417	Remote Similarity	NPC142151
0.5417	Remote Similarity	NPC267694
0.5414	Remote Similarity	NPC329976
0.5414	Remote Similarity	NPC478559
0.5414	Remote Similarity	NPC478560
0.5401	Remote Similarity	NPC475209
0.5401	Remote Similarity	NPC219180
0.5401	Remote Similarity	NPC257211
0.5385	Remote Similarity	NPC481082
0.5385	Remote Similarity	NPC164419
0.5385	Remote Similarity	NPC144644
0.5385	Remote Similarity	NPC37860
0.5385	Remote Similarity	NPC170407
0.5373	Remote Similarity	NPC605294
0.5362	Remote Similarity	NPC191827
0.5354	Remote Similarity	NPC161674
0.5352	Remote Similarity	NPC65105
0.5349	Remote Similarity	NPC305267
0.5333	Remote Similarity	NPC213952
0.5324	Remote Similarity	NPC25663
0.5323	Remote Similarity	NPC48499

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC302543 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7033
0.1-0.2	2056
0.2-0.3	57
0.3-0.4	3
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