NPASS Compound

Natural Product: NPC71391

Natural Product ID	NPC71391
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gordonoside J
IUPAC Name	(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9S,12aS,14aR,14bR)-7,8-dihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
Synonyms	gordonoside J
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1782821
PubChem CID	54586126
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 172180 0 0 0 0 0 0 0 0999 V2000 8.6469 -2.6528 -5.7731 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7623 -3.1934 -4.8134 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9972 -2.0856 -4.1117 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1574 -2.6605 -3.2030 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3265 -2.1173 -1.9182 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5673 -2.8706 -1.0488 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5756 -2.0641 -0.4303 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2872 -2.6012 -1.0828 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3392 -4.0147 -0.9250 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5245 -4.3853 0.3806 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4679 -3.2671 1.3938 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5564 -2.2810 1.0425 C 0 0 2 0 0 0 0 0 0 0 0 0 4.5371 -1.1301 1.8177 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6412 -1.0252 2.6336 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2988 -1.0858 3.9998 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4314 -1.3057 4.7787 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4672 -0.2071 4.6270 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7906 -0.0704 3.1553 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4424 0.2434 2.4696 C 0 0 1 0 0 0 0 0 0 0 0 0 6.7256 0.5890 1.1777 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3122 1.8505 0.7870 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3197 1.6423 -0.1775 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7357 2.8404 -0.5885 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7377 3.8077 -1.1347 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1264 3.2224 -1.1430 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4289 2.7236 0.2526 C 0 0 1 0 0 0 0 0 0 0 0 0 7.6768 3.7727 1.1272 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2212 2.1657 -2.0233 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7880 4.9746 -0.3703 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7449 0.8759 2.8912 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8848 0.9821 5.0855 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8536 -3.8334 2.6331 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5833 -5.4898 0.7547 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7778 -5.9019 -0.1072 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5616 -6.0777 2.0085 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1245 -2.2088 -0.6388 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2063 -1.5884 -1.4383 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1786 -2.4906 -2.0571 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2408 -1.9769 -1.9686 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5481 -1.4709 -0.5948 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6853 -0.2731 -0.3434 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7166 -0.3281 -0.8335 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6594 0.0930 0.3125 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9624 0.8256 -1.8512 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8710 0.0661 1.1116 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2286 -0.0062 1.6619 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3791 -0.4959 0.8417 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9505 -0.9588 -0.5280 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9937 -1.8314 -1.0986 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1513 -0.9112 -1.2854 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3729 0.1627 -0.4981 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4786 0.5418 0.6404 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8520 1.8991 0.5220 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4390 0.5889 1.8354 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7704 1.0278 2.9833 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5338 1.5889 1.6056 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3958 1.2102 0.4768 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6109 0.9270 -0.8048 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5174 2.0076 -1.7924 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1431 3.3295 -1.5482 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0797 4.4353 -1.5727 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0188 3.6964 -2.7691 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0435 3.4774 -0.3655 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5042 2.1140 0.0789 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.6689 2.0972 0.8403 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.8973 1.6931 0.4070 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8641 1.3185 -0.8159 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1544 1.6293 1.0835 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3721 1.9642 2.3453 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2471 2.4555 3.1720 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.3739 1.1433 0.3329 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0799 -0.1087 0.8818 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8275 0.0058 2.0241 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0563 2.8866 1.6343 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0886 -1.5869 1.6287 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3650 -2.5982 0.3457 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7735 -2.2227 -1.4919 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5946 -1.2830 -2.3356 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8845 -0.9987 -3.6122 C 0 0 1 0 0 0 0 0 0 0 0 0 8.8231 -0.7473 -4.6351 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8892 -1.7720 -2.5302 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9156 -1.9525 -0.1273 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4924 -3.0832 -6.6466 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0734 -3.8894 -5.3284 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4177 -3.7484 -4.1121 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3450 -1.6298 -4.9055 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9983 -1.0805 -1.9292 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6682 -1.0203 -0.7272 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4969 -2.4682 -2.1813 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5464 -4.8411 0.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4818 -2.8558 1.5529 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5123 -2.8488 1.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2703 -1.9295 2.4395 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0346 -1.3076 5.8435 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8787 -2.2711 4.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3458 -0.4859 5.2237 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0626 -1.0704 2.7614 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9017 1.0437 3.0330 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8117 2.4055 1.6036 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0583 2.5549 -1.4385 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0556 3.2795 0.1765 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5075 4.1062 -2.1862 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8819 3.9904 -1.3792 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3600 2.1313 0.1656 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6426 3.8112 1.3078 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0216 2.4755 -2.9423 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4956 5.5715 -0.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6108 0.4589 2.6006 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4907 1.5188 5.6511 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1822 -3.6831 3.3374 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6874 -6.4626 2.4001 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8573 -1.3367 -2.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2703 -3.5600 -1.7674 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3160 -2.5741 -3.1835 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5061 -1.2833 -2.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8716 -2.9029 -2.1368 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1617 0.5860 -0.8804 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6727 0.1591 -0.1922 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4601 1.1190 0.6454 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7697 -0.6599 1.0798 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9761 1.8032 -1.3301 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0808 0.8020 -2.5200 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8541 0.6064 -2.4412 H 0 0 0 0 0 0 0 0 0 0 0 0 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H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9302 3.0435 -2.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3215 4.7457 -2.6087 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5621 4.0945 0.3840 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0125 4.0208 -0.6036 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8383 1.6720 -0.9292 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3479 1.8931 2.7967 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5990 2.6905 4.2153 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5290 1.6358 3.2983 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7989 3.3999 2.8111 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2907 1.2333 0.9263 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2057 0.1151 -0.0785 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5414 1.7709 -0.5903 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3726 -0.9644 0.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7776 -0.3559 0.0076 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1387 -0.8936 2.3030 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8165 3.1040 2.5705 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1856 -1.1692 2.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5113 -2.5087 1.7701 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0317 -1.8883 1.1757 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1973 -2.3407 1.3838 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1027 -3.3832 0.1273 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3807 -3.0960 0.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0657 -3.2794 -1.6202 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6411 -0.3059 -1.7697 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2688 -0.0650 -3.5701 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7313 -0.7843 -4.2865 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9620 -2.6033 -2.0066 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8459 -1.6662 0.0189 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 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 25 28 1 0 24 29 1 0 18 30 1 0 17 31 1 0 11 32 1 0 10 33 1 0 33 34 2 0 33 35 1 0 8 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 42 44 1 0 41 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 2 0 51 52 1 0 52 53 1 6 52 54 1 0 54 55 1 0 54 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 60 62 1 0 60 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 2 0 66 68 1 0 68 69 2 0 69 70 1 0 68 71 1 0 57 72 1 1 72 73 1 0 56 74 1 0 47 75 1 1 40 76 1 1 5 77 1 0 77 78 1 0 78 79 1 0 79 80 1 0 78 81 1 0 77 82 1 0 79 3 1 0 12 7 1 0 19 14 1 0 26 21 1 0 42 37 1 0 52 47 1 0 64 57 1 0 48 40 1 0 58 51 1 0 1 83 1 0 2 84 1 0 2 85 1 0 3 86 1 6 5 87 1 6 7 88 1 1 8 89 1 6 10 90 1 6 11 91 1 1 12 92 1 1 14 93 1 6 16 94 1 0 16 95 1 0 17 96 1 1 18 97 1 6 19 98 1 1 21 99 1 1 23100 1 0 23101 1 0 24102 1 6 25103 1 6 26104 1 6 27105 1 0 28106 1 0 29107 1 0 30108 1 0 31109 1 0 32110 1 0 35111 1 0 37112 1 6 38113 1 0 38114 1 0 39115 1 0 39116 1 0 41117 1 6 43118 1 0 43119 1 0 43120 1 0 44121 1 0 44122 1 0 44123 1 0 45124 1 0 45125 1 0 46126 1 0 46127 1 0 48128 1 6 49129 1 0 49130 1 0 50131 1 0 53132 1 0 53133 1 0 53134 1 0 54135 1 1 55136 1 0 56137 1 1 58138 1 6 59139 1 0 59140 1 0 61141 1 0 61142 1 0 61143 1 0 62144 1 0 62145 1 0 62146 1 0 63147 1 0 63148 1 0 64149 1 6 69150 1 0 70151 1 0 70152 1 0 70153 1 0 71154 1 0 71155 1 0 71156 1 0 72157 1 0 72158 1 0 73159 1 0 74160 1 0 75161 1 0 75162 1 0 75163 1 0 76164 1 0 76165 1 0 76166 1 0 77167 1 1 78168 1 1 79169 1 1 80170 1 0 81171 1 0 82172 1 0 M END

Standard InCHIKey	GMMMRIWOKNYPOM-BFYDJWHYSA-N
Standard InCHI	InChI=1S/C57H90O25/c1-10-23(2)47(73)77-32-18-52(3,4)17-25-24-11-12-30-54(7)15-14-31(53(5,6)29(54)13-16-55(30,8)56(24,9)44(69)45(70)57(25,32)22-59)78-51-43(82-49-38(67)36(65)35(64)28(19-58)76-49)40(39(68)41(80-51)46(71)72)79-50-42(34(63)27(61)21-75-50)81-48-37(66)33(62)26(60)20-74-48/h10-11,25-45,48-51,58-70H,12-22H2,1-9H3,(H,71,72)/b23-10-/t25-,26+,27-,28+,29-,30+,31-,32-,33-,34-,35-,36-,37+,38+,39-,40-,41-,42+,43+,44-,45+,48-,49-,50-,51+,54-,55+,56-,57+/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[C@@H]2OC[C@H]([C@@H]([C@H]2O)O)O)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@@H](O)[C@H]([C@@]2([C@H]3CC(C)(C)C[C@@H]2OC(=O)/C(=CC)/C)CO)O)C)C)[C@@H]([C@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1174.58	Volume:	1126.629 ? Van der Waals volume.
Dense:	1.043	LogP:	1.121 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.004 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.164 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	53.0
TPSA:	400.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	14.0	Rings:	9.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.042	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.227	Fsp³:	0.895
MCE-18:	202.815 ? 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:	0.702	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.23	Promiscuous compounds:	0.263

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.172	MDCK Permeability:	-5.18
Pgp-inhibitor:	0.0	Pgp-substrate:	0.983
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):	0.976
20% Bioavailability (F20%):	0.968	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.762
Plasma Protein Binding (PPB):	61.154%	Volume Distribution (VD):	-0.42
Fu:	22.546% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.779	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.164
HLM stability:	0.028 ? 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):

-0.308

Half-life (T1/2):

3.406

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.461	Drug-induced Liver Injury (DILI):	0.819
AMES Toxicity:	0.921	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.029	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.71	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.24	RPMI-8226 Immunitoxicity:	0.241
A549 Cytotoxicity:	0.373	Hek293 Cytotoxicity:	0.124
BCF:	0.363 ? 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:	3.38 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.213 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.887 ? 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	=	9.1	%	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 NPC71391 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	22478
0.1-0.2	23137
0.2-0.3	3125
0.3-0.4	567
0.4-0.5	375
0.5-0.6	107
0.6-0.7	34
0.7-0.8	0
0.8-0.85	3
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8829	High Similarity	NPC178264
0.8739	High Similarity	NPC192765
0.8584	High Similarity	NPC265841
0.8482	Intermediate Similarity	NPC277212
0.8482	Intermediate Similarity	NPC30279
0.8	Intermediate Similarity	NPC473918
0.7815	Intermediate Similarity	NPC476779
0.7731	Intermediate Similarity	NPC271610
0.7456	Intermediate Similarity	NPC329976
0.7395	Intermediate Similarity	NPC46823
0.7295	Intermediate Similarity	NPC225791
0.7236	Intermediate Similarity	NPC484059
0.7236	Intermediate Similarity	NPC484060
0.7213	Intermediate Similarity	NPC476780
0.7167	Intermediate Similarity	NPC602995
0.7154	Intermediate Similarity	NPC312650
0.7131	Intermediate Similarity	NPC484061
0.7131	Intermediate Similarity	NPC484062
0.7094	Intermediate Similarity	NPC605294
0.7073	Intermediate Similarity	NPC488308
0.704	Intermediate Similarity	NPC476777
0.7025	Intermediate Similarity	NPC283417
0.7025	Intermediate Similarity	NPC200049
0.7009	Intermediate Similarity	NPC609281
0.6935	Remote Similarity	NPC476774
0.6825	Remote Similarity	NPC484833
0.6797	Remote Similarity	NPC476775
0.6744	Remote Similarity	NPC488309
0.6695	Remote Similarity	NPC477075
0.6695	Remote Similarity	NPC477076
0.6639	Remote Similarity	NPC477077
0.6565	Remote Similarity	NPC476778
0.656	Remote Similarity	NPC47995
0.6515	Remote Similarity	NPC476776
0.6512	Remote Similarity	NPC110700
0.6491	Remote Similarity	NPC603026
0.6475	Remote Similarity	NPC25998
0.6446	Remote Similarity	NPC187290
0.6393	Remote Similarity	NPC606553
0.6349	Remote Similarity	NPC264566
0.6341	Remote Similarity	NPC470475
0.632	Remote Similarity	NPC284449
0.629	Remote Similarity	NPC609119
0.6241	Remote Similarity	NPC484063
0.6241	Remote Similarity	NPC484064
0.621	Remote Similarity	NPC478152
0.621	Remote Similarity	NPC478151
0.6198	Remote Similarity	NPC470914
0.6124	Remote Similarity	NPC329828
0.6116	Remote Similarity	NPC302887
0.6098	Remote Similarity	NPC477078
0.6033	Remote Similarity	NPC470913
0.6032	Remote Similarity	NPC610461
0.6016	Remote Similarity	NPC477079
0.6016	Remote Similarity	NPC478150
0.6	Remote Similarity	NPC329923
0.6	Remote Similarity	NPC475281
0.6	Remote Similarity	NPC4749
0.597	Remote Similarity	NPC302543
0.5968	Remote Similarity	NPC160452
0.5956	Remote Similarity	NPC279915
0.595	Remote Similarity	NPC475591
0.595	Remote Similarity	NPC236870
0.5891	Remote Similarity	NPC470476
0.5887	Remote Similarity	NPC301449
0.5887	Remote Similarity	NPC601290
0.5887	Remote Similarity	NPC606145
0.5873	Remote Similarity	NPC480939
0.5868	Remote Similarity	NPC44716
0.584	Remote Similarity	NPC187618
0.5833	Remote Similarity	NPC470518
0.5781	Remote Similarity	NPC607904
0.5781	Remote Similarity	NPC610204
0.5778	Remote Similarity	NPC329657
0.575	Remote Similarity	NPC22956
0.5748	Remote Similarity	NPC477197
0.5714	Remote Similarity	NPC21691
0.5714	Remote Similarity	NPC127056
0.5669	Remote Similarity	NPC469947
0.5669	Remote Similarity	NPC480948
0.5656	Remote Similarity	NPC605226
0.5649	Remote Similarity	NPC609305
0.5639	Remote Similarity	NPC181066
0.5639	Remote Similarity	NPC301639
0.5639	Remote Similarity	NPC478065
0.5635	Remote Similarity	NPC23275
0.563	Remote Similarity	NPC262796
0.563	Remote Similarity	NPC45346
0.562	Remote Similarity	NPC263756
0.56	Remote Similarity	NPC64715
0.5547	Remote Similarity	NPC475377
0.5547	Remote Similarity	NPC476074
0.5538	Remote Similarity	NPC313110
0.5492	Remote Similarity	NPC80843
0.5492	Remote Similarity	NPC213674
0.5484	Remote Similarity	NPC251768
0.5476	Remote Similarity	NPC79718
0.5474	Remote Similarity	NPC478153
0.5469	Remote Similarity	NPC477193
0.5426	Remote Similarity	NPC104137
0.5426	Remote Similarity	NPC26626
0.5426	Remote Similarity	NPC477194
0.5407	Remote Similarity	NPC82380
0.5407	Remote Similarity	NPC244296
0.5403	Remote Similarity	NPC117714
0.5385	Remote Similarity	NPC11242
0.5379	Remote Similarity	NPC478600
0.5379	Remote Similarity	NPC478599
0.5379	Remote Similarity	NPC478155
0.5379	Remote Similarity	NPC478154
0.5347	Remote Similarity	NPC150893
0.5344	Remote Similarity	NPC288205
0.5344	Remote Similarity	NPC51465
0.5323	Remote Similarity	NPC112352
0.5319	Remote Similarity	NPC329960
0.5317	Remote Similarity	NPC63159
0.5308	Remote Similarity	NPC481078
0.5285	Remote Similarity	NPC472949
0.5285	Remote Similarity	NPC488561
0.528	Remote Similarity	NPC30289
0.5271	Remote Similarity	NPC324875
0.5271	Remote Similarity	NPC292677
0.5246	Remote Similarity	NPC59804
0.5242	Remote Similarity	NPC469946
0.5238	Remote Similarity	NPC164389
0.5227	Remote Similarity	NPC107536
0.5227	Remote Similarity	NPC475119
0.5227	Remote Similarity	NPC280029
0.5227	Remote Similarity	NPC9470
0.5221	Remote Similarity	NPC470912
0.5208	Remote Similarity	NPC489209
0.52	Remote Similarity	NPC192791
0.5191	Remote Similarity	NPC207738
0.5182	Remote Similarity	NPC273668
0.5177	Remote Similarity	NPC11577
0.5177	Remote Similarity	NPC141600
0.5154	Remote Similarity	NPC218954
0.5145	Remote Similarity	NPC478598
0.5122	Remote Similarity	NPC56713
0.5118	Remote Similarity	NPC104400
0.5118	Remote Similarity	NPC10320
0.5115	Remote Similarity	NPC480474
0.5108	Remote Similarity	NPC286457
0.5108	Remote Similarity	NPC485123
0.5101	Remote Similarity	NPC489208
0.5079	Remote Similarity	NPC478066
0.5076	Remote Similarity	NPC475486
0.5075	Remote Similarity	NPC473824
0.5074	Remote Similarity	NPC166422
0.5074	Remote Similarity	NPC219180
0.5074	Remote Similarity	NPC251263
0.5074	Remote Similarity	NPC123199
0.5072	Remote Similarity	NPC85154
0.5065	Remote Similarity	NPC477474
0.5039	Remote Similarity	NPC481082
0.5039	Remote Similarity	NPC164419
0.5039	Remote Similarity	NPC297263
0.5038	Remote Similarity	NPC470915
0.5038	Remote Similarity	NPC477191
0.5036	Remote Similarity	NPC269484
0.5036	Remote Similarity	NPC470517
0.5036	Remote Similarity	NPC57484
0.5036	Remote Similarity	NPC475140
0.5036	Remote Similarity	NPC97918
0.5034	Remote Similarity	NPC475368

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC71391 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6892
0.1-0.2	2203
0.2-0.3	51
0.3-0.4	4
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