NPASS Compound

Natural Product: NPC4749

Natural Product ID	NPC4749
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Gordonoside L
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]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxyoxane-2-carboxylic acid
Synonyms	gordonoside L
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1782845
PubChem CID	54581245
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 157165 0 0 0 0 0 0 0 0999 V2000 -9.2907 -2.2948 3.0480 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4436 -1.5900 2.7849 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0980 -0.1949 2.2823 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.3423 -0.2545 1.1170 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1215 1.0183 0.6596 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1025 1.1268 -0.2855 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9625 1.9221 -0.1805 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8610 2.6008 0.8710 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9323 1.9496 -1.2678 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6123 2.4156 -2.5271 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2837 1.3035 -3.2976 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3152 0.2887 -3.8611 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0695 0.3819 -3.0084 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4078 0.5711 -1.5504 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2275 0.1838 -0.7405 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1493 -1.1039 -0.4269 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0843 -1.7617 0.3716 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9618 -0.7896 0.5237 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4993 0.5256 0.9383 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1897 1.1516 -0.2921 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8924 2.4085 0.1493 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8730 2.9156 -0.8520 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2664 3.4701 -1.9928 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2127 1.5212 -1.3529 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6199 0.4104 1.9719 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5057 1.5050 1.4349 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3332 0.9592 2.1718 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2037 -0.2213 1.4352 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8307 -1.3136 1.3820 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2308 -1.8464 2.7016 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2489 -2.4722 0.5637 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0694 -2.9107 1.0514 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0517 -1.7471 0.9666 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5813 -0.6469 1.8389 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4726 0.5745 1.5161 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7809 -0.8813 3.3081 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3387 -2.2002 1.1783 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2013 -2.2508 0.1398 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3080 -3.6131 -0.2126 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2583 -4.3008 0.4294 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1315 -4.5433 1.8708 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1386 -4.1613 2.5074 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1442 -5.2132 2.5231 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6330 -3.8087 0.0850 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7066 -2.3027 -0.0343 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4998 -1.5992 0.4614 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5768 -0.2792 -0.0593 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8073 -1.9370 0.7810 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8654 -1.4847 0.0522 C 0 0 2 0 0 0 0 0 0 0 0 0 9.9034 -2.4480 0.0922 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7745 -2.2695 -0.9557 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3823 -0.8958 -0.8753 C 0 0 1 0 0 0 0 0 0 0 0 0 10.9228 -0.2176 0.3810 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3808 -0.1399 0.4164 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0465 0.8151 -0.5119 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5291 1.9919 0.0207 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2900 2.2224 -0.5688 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4194 1.9126 -1.9315 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3380 2.9001 -2.6241 C 0 0 1 0 0 0 0 0 0 0 0 0 8.9647 3.8504 -1.6300 C 0 0 1 0 0 0 0 0 0 0 0 0 9.4068 3.1839 -0.3608 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3122 4.1080 0.6827 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0659 4.4416 -2.2714 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3440 2.2798 -3.3481 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2740 -1.0061 1.4692 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7704 -1.0250 -0.9202 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0405 -4.4353 -1.0991 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9337 0.7454 -5.2515 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8529 -1.0990 -3.9534 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4474 1.5561 0.1497 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.2746 1.8560 1.4019 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.4027 0.5378 2.1345 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.8828 0.8036 3.4259 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.5686 2.1748 0.9364 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3011 2.7457 -0.5262 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.4363 -3.2363 2.7827 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9744 -2.0980 1.9447 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1531 -1.5575 3.6161 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5204 0.3297 3.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8641 1.6674 1.5260 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3990 3.1268 -2.2403 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8630 2.9111 -3.1654 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8318 1.8072 -4.1332 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0366 0.7653 -2.7122 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5315 1.2841 -3.3717 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5041 -0.5529 -3.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2801 -0.1230 -1.3574 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9616 -1.7745 -0.7914 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6751 -2.6268 -0.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5409 -2.1186 1.3180 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5161 -0.7117 -0.5152 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0954 3.1876 0.2416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4362 2.3074 1.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3355 3.8265 -0.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6810 4.3020 -2.2770 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1186 2.6213 -1.4700 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4257 1.0208 -2.3432 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1536 1.1932 -1.1455 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5817 1.3051 2.6519 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6211 0.3319 1.5041 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5171 -0.4628 2.6240 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1042 2.1719 0.6161 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0505 2.2422 2.0991 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5316 0.7621 3.2454 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4518 1.7571 2.1752 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3279 0.1146 0.3603 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1662 -2.4154 2.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3565 -1.0819 3.4942 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4835 -2.5649 3.1083 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1813 -2.1174 -0.4832 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9343 -3.3448 0.5814 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4571 -3.6675 0.3372 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0027 -3.3836 2.0194 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9841 -1.4289 -0.0870 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5073 0.2241 1.5467 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3628 1.2882 2.3872 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1490 1.0920 0.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6957 -1.9082 3.6469 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1668 -0.1653 3.8878 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8444 -0.5835 3.5819 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8019 -1.8014 -0.8086 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2364 -5.3845 -0.0023 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1855 -5.3624 3.5060 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3081 -4.2095 0.8786 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9194 -2.0806 -1.0902 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6242 -1.4278 1.5770 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4700 -0.2573 -1.0338 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5659 -1.4746 -1.0352 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5776 -3.0567 -0.9765 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1639 -2.3221 -1.8914 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0382 -0.2773 -1.7507 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3752 0.7842 0.5204 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1355 0.2263 1.4200 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4740 1.9561 1.1131 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8912 0.9166 -2.0095 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3932 1.9447 -2.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7278 3.4909 -3.3309 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2288 4.6676 -1.4381 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4786 2.8515 -0.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0890 3.9576 1.3092 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6045 4.9561 -1.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1702 2.2530 -2.7844 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2013 -1.3553 1.3519 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0394 -1.9597 -1.0706 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2326 -5.3806 -0.8657 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7443 -0.1194 -5.9256 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1039 1.4662 -5.2527 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8101 1.2948 -5.6898 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3014 -1.3503 -4.9395 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9777 -1.8075 -3.8431 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6347 -1.3283 -3.2013 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0202 0.7740 -0.3914 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8566 2.6590 2.0077 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1927 -0.0521 1.6167 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1734 0.6698 4.0938 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0244 2.8308 1.5256 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4828 3.5225 0.0637 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 2 0 9 7 1 1 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 2 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 20 24 1 6 19 25 1 1 19 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 33 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 2 0 41 43 1 0 40 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 45 48 1 0 48 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 56 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 59 64 1 0 53 65 1 0 52 66 1 0 44 67 1 0 12 68 1 0 12 69 1 0 5 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 71 74 1 0 70 75 1 0 72 3 1 0 22 9 1 0 34 28 1 0 46 38 1 0 54 49 1 0 61 56 1 0 14 9 1 0 20 15 1 0 29 18 1 0 1 76 1 0 2 77 1 0 2 78 1 0 3 79 1 1 5 80 1 1 10 81 1 0 10 82 1 0 11 83 1 0 11 84 1 0 13 85 1 0 13 86 1 0 14 87 1 1 16 88 1 0 17 89 1 0 17 90 1 0 18 91 1 6 21 92 1 0 21 93 1 0 22 94 1 1 23 95 1 0 24 96 1 0 24 97 1 0 24 98 1 0 25 99 1 0 25100 1 0 25101 1 0 26102 1 0 26103 1 0 27104 1 0 27105 1 0 28106 1 6 30107 1 0 30108 1 0 30109 1 0 31110 1 0 31111 1 0 32112 1 0 32113 1 0 33114 1 6 35115 1 0 35116 1 0 35117 1 0 36118 1 0 36119 1 0 36120 1 0 38121 1 6 40122 1 6 43123 1 0 44124 1 1 45125 1 6 46126 1 1 47127 1 0 49128 1 6 51129 1 0 51130 1 0 52131 1 6 53132 1 1 54133 1 1 56134 1 1 58135 1 0 58136 1 0 59137 1 6 60138 1 1 61139 1 6 62140 1 0 63141 1 0 64142 1 0 65143 1 0 66144 1 0 67145 1 0 68146 1 0 68147 1 0 68148 1 0 69149 1 0 69150 1 0 69151 1 0 70152 1 6 71153 1 1 72154 1 6 73155 1 0 74156 1 0 75157 1 0 M END

Standard InCHIKey	DIPDDQDKKVVWRH-ILKBLGRDSA-N
Standard InCHI	InChI=1S/C52H82O23/c1-47(2)14-15-52(46(67)75-43-35(62)33(60)32(59)25(18-53)70-43)22(16-47)21-8-9-27-49(5)12-11-29(48(3,4)26(49)10-13-50(27,6)51(21,7)17-28(52)56)71-44-37(64)38(36(63)39(73-44)41(65)66)72-45-40(31(58)24(55)20-69-45)74-42-34(61)30(57)23(54)19-68-42/h8,22-40,42-45,53-64H,9-20H2,1-7H3,(H,65,66)/t22-,23-,24-,25+,26-,27+,28+,29-,30-,31-,32+,33-,34+,35+,36-,37+,38-,39-,40+,42-,43-,44+,45-,49-,50+,51+,52+/m0/s1
SMILES	OC[C@H]1O[C@@H](OC(=O)[C@@]23CCC(C[C@H]3C3=CC[C@H]4[C@@]([C@@]3(C[C@H]2O)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H](C2(C)C)O[C@@H]2O[C@H](C(=O)O)[C@H]([C@@H]([C@H]2O)O[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)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1074.52	Volume:	1025.205 ? Van der Waals volume.
Dense:	1.048	LogP:	0.714 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.715 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.302 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	52.0
TPSA:	370.97 ? Topological Polar Surface Area.	H-Bond Acceptor:	23.0
H-Bond Donor:	13.0	Rings:	9.0
Heavy Atoms:	23.0

MedChem Properties

QED Drug-Likeness Score:	0.066	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.818	Fsp³:	0.923
MCE-18:	198.8 ? 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:	0.701	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.201	Promiscuous compounds:	0.134

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.386	MDCK Permeability:	-4.979
Pgp-inhibitor:	0.0	Pgp-substrate:	0.519
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):	0.718
20% Bioavailability (F20%):	0.629	30% Bioavailability (F30%):	0.995
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.611
Plasma Protein Binding (PPB):	62.839%	Volume Distribution (VD):	-0.456
Fu:	24.135% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.049
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.007
HLM stability:	0.143 ? 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):

-0.193

Half-life (T1/2):

3.743

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.851	Drug-induced Liver Injury (DILI):	0.995
AMES Toxicity:	0.98	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.064	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.866	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.886	RPMI-8226 Immunitoxicity:	0.189
A549 Cytotoxicity:	0.915	Hek293 Cytotoxicity:	0.254
BCF:	0.585 ? 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:	3.336 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.86 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.778 ? 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	=	14.0	%	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 NPC4749 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	22341
0.1-0.2	23335
0.2-0.3	2967
0.3-0.4	598
0.4-0.5	311
0.5-0.6	138
0.6-0.7	49
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9352	High Similarity	NPC21691
0.9048	High Similarity	NPC11242
0.8559	High Similarity	NPC283417
0.8559	High Similarity	NPC200049
0.7833	Intermediate Similarity	NPC302543
0.7727	Intermediate Similarity	NPC64715
0.7455	Intermediate Similarity	NPC164389
0.7304	Intermediate Similarity	NPC104137
0.7304	Intermediate Similarity	NPC26626
0.7264	Intermediate Similarity	NPC1046
0.719	Intermediate Similarity	NPC85154
0.7073	Intermediate Similarity	NPC286457
0.6991	Remote Similarity	NPC159309
0.6991	Remote Similarity	NPC86222
0.6983	Remote Similarity	NPC301449
0.6983	Remote Similarity	NPC601290
0.6917	Remote Similarity	NPC123522
0.6897	Remote Similarity	NPC114484
0.6875	Remote Similarity	NPC220160
0.6864	Remote Similarity	NPC481078
0.68	Remote Similarity	NPC265841
0.6723	Remote Similarity	NPC187290
0.6696	Remote Similarity	NPC488526
0.6591	Remote Similarity	NPC489209
0.6535	Remote Similarity	NPC473452
0.6535	Remote Similarity	NPC488308
0.6532	Remote Similarity	NPC123199
0.6493	Remote Similarity	NPC33012
0.6484	Remote Similarity	NPC271610
0.6484	Remote Similarity	NPC312650
0.6423	Remote Similarity	NPC489208
0.6418	Remote Similarity	NPC8524
0.641	Remote Similarity	NPC251768
0.6406	Remote Similarity	NPC13998
0.6389	Remote Similarity	NPC485563
0.6379	Remote Similarity	NPC112352
0.6364	Remote Similarity	NPC477193
0.6293	Remote Similarity	NPC469946
0.625	Remote Similarity	NPC302887
0.6241	Remote Similarity	NPC488309
0.624	Remote Similarity	NPC79643
0.6231	Remote Similarity	NPC470876
0.623	Remote Similarity	NPC160452
0.6218	Remote Similarity	NPC475591
0.6218	Remote Similarity	NPC63159
0.6218	Remote Similarity	NPC236870
0.6207	Remote Similarity	NPC157868
0.619	Remote Similarity	NPC284449
0.6183	Remote Similarity	NPC476779
0.6148	Remote Similarity	NPC102505
0.6148	Remote Similarity	NPC488514
0.6134	Remote Similarity	NPC44716
0.6129	Remote Similarity	NPC815
0.6102	Remote Similarity	NPC192791
0.6048	Remote Similarity	NPC207738
0.6033	Remote Similarity	NPC297263
0.6031	Remote Similarity	NPC476774
0.6031	Remote Similarity	NPC476780
0.6	Remote Similarity	NPC71391
0.6	Remote Similarity	NPC232237
0.6	Remote Similarity	NPC480936
0.5985	Remote Similarity	NPC475514
0.597	Remote Similarity	NPC309223
0.5969	Remote Similarity	NPC602995
0.5968	Remote Similarity	NPC69811
0.5932	Remote Similarity	NPC6377
0.5932	Remote Similarity	NPC208381
0.592	Remote Similarity	NPC475486
0.592	Remote Similarity	NPC31838
0.592	Remote Similarity	NPC477194
0.5917	Remote Similarity	NPC117714
0.5896	Remote Similarity	NPC110700
0.5896	Remote Similarity	NPC476777
0.5891	Remote Similarity	NPC257211
0.5887	Remote Similarity	NPC481079
0.5887	Remote Similarity	NPC477191
0.5882	Remote Similarity	NPC80843
0.5868	Remote Similarity	NPC305267
0.5867	Remote Similarity	NPC23020
0.5865	Remote Similarity	NPC41061
0.5865	Remote Similarity	NPC227551
0.5852	Remote Similarity	NPC33068
0.5852	Remote Similarity	NPC476991
0.5827	Remote Similarity	NPC477196
0.5821	Remote Similarity	NPC484059
0.5821	Remote Similarity	NPC484060
0.582	Remote Similarity	NPC105800
0.5809	Remote Similarity	NPC476775
0.5806	Remote Similarity	NPC281148
0.5802	Remote Similarity	NPC25663
0.5797	Remote Similarity	NPC476776
0.5786	Remote Similarity	NPC485562
0.5785	Remote Similarity	NPC30289
0.5781	Remote Similarity	NPC475287
0.5778	Remote Similarity	NPC236638
0.5778	Remote Similarity	NPC294453
0.5778	Remote Similarity	NPC305981
0.5769	Remote Similarity	NPC135904
0.5766	Remote Similarity	NPC482010
0.5763	Remote Similarity	NPC475516
0.576	Remote Similarity	NPC324875
0.576	Remote Similarity	NPC292677
0.5758	Remote Similarity	NPC192765
0.5748	Remote Similarity	NPC477195
0.5746	Remote Similarity	NPC258617
0.5738	Remote Similarity	NPC40775
0.5735	Remote Similarity	NPC261506
0.5735	Remote Similarity	NPC4328
0.5726	Remote Similarity	NPC475208
0.5725	Remote Similarity	NPC279915
0.5725	Remote Similarity	NPC470218
0.5725	Remote Similarity	NPC476778
0.5714	Remote Similarity	NPC178264
0.5714	Remote Similarity	NPC187618
0.5714	Remote Similarity	NPC480473
0.5714	Remote Similarity	NPC480420
0.5714	Remote Similarity	NPC127056
0.5714	Remote Similarity	NPC480474
0.5703	Remote Similarity	NPC288205
0.5703	Remote Similarity	NPC51465
0.569	Remote Similarity	NPC90856
0.5667	Remote Similarity	NPC473884
0.5662	Remote Similarity	NPC481081
0.5652	Remote Similarity	NPC484063
0.5652	Remote Similarity	NPC484064
0.5652	Remote Similarity	NPC142151
0.5652	Remote Similarity	NPC267694
0.5645	Remote Similarity	NPC481082
0.5645	Remote Similarity	NPC164419
0.5645	Remote Similarity	NPC475504
0.5639	Remote Similarity	NPC481080
0.5638	Remote Similarity	NPC475584
0.5638	Remote Similarity	NPC475152
0.5635	Remote Similarity	NPC218954
0.562	Remote Similarity	NPC263756
0.562	Remote Similarity	NPC144644
0.562	Remote Similarity	NPC37860
0.562	Remote Similarity	NPC170407
0.5612	Remote Similarity	NPC250247
0.561	Remote Similarity	NPC480475
0.56	Remote Similarity	NPC488515
0.5597	Remote Similarity	NPC484061
0.5597	Remote Similarity	NPC484062
0.5597	Remote Similarity	NPC57484
0.5593	Remote Similarity	NPC48499
0.5581	Remote Similarity	NPC475119
0.558	Remote Similarity	NPC70809
0.5574	Remote Similarity	NPC223301
0.5574	Remote Similarity	NPC242840
0.5574	Remote Similarity	NPC171544
0.5556	Remote Similarity	NPC104372
0.5538	Remote Similarity	NPC60557
0.5538	Remote Similarity	NPC473824
0.5538	Remote Similarity	NPC67857
0.5538	Remote Similarity	NPC610204
0.5537	Remote Similarity	NPC295371
0.5532	Remote Similarity	NPC51099
0.553	Remote Similarity	NPC166422
0.553	Remote Similarity	NPC219180
0.5528	Remote Similarity	NPC160415
0.5528	Remote Similarity	NPC605226
0.5512	Remote Similarity	NPC23275
0.5504	Remote Similarity	NPC210729
0.5504	Remote Similarity	NPC82931
0.5503	Remote Similarity	NPC475394
0.5492	Remote Similarity	NPC213674
0.5489	Remote Similarity	NPC475140
0.5489	Remote Similarity	NPC191827
0.5469	Remote Similarity	NPC477192
0.5462	Remote Similarity	NPC25998
0.5462	Remote Similarity	NPC213952
0.5462	Remote Similarity	NPC185466
0.5461	Remote Similarity	NPC68767
0.5461	Remote Similarity	NPC293031
0.5448	Remote Similarity	NPC475368
0.5447	Remote Similarity	NPC75417
0.5431	Remote Similarity	NPC128925
0.5429	Remote Similarity	NPC51564
0.5424	Remote Similarity	NPC204458
0.5424	Remote Similarity	NPC214484
0.5424	Remote Similarity	NPC238935
0.5423	Remote Similarity	NPC110385
0.5423	Remote Similarity	NPC153673
0.542	Remote Similarity	NPC313110
0.542	Remote Similarity	NPC609119
0.5417	Remote Similarity	NPC480421
0.5414	Remote Similarity	NPC475209
0.5414	Remote Similarity	NPC251263
0.541	Remote Similarity	NPC39211
0.541	Remote Similarity	NPC488561
0.54	Remote Similarity	NPC485564
0.5397	Remote Similarity	NPC222580
0.5373	Remote Similarity	NPC480423
0.5368	Remote Similarity	NPC470518
0.5368	Remote Similarity	NPC237191
0.536	Remote Similarity	NPC104400
0.536	Remote Similarity	NPC10320
0.536	Remote Similarity	NPC46665
0.535	Remote Similarity	NPC472270

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC4749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6817
0.1-0.2	2280
0.2-0.3	49
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
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
0.5122	Remote Similarity	NPD8295	Clinical (unspecified phase)

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