NPASS Compound

Natural Product: NPC305267

Natural Product ID	NPC305267
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dianversicoside F
IUPAC Name	8a-O-[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] 4-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (3S,4S,4aR,6aR,6bS,8R,8aR,12aS,14aR,14bR)-3,8-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylate
Synonyms	Dianversicoside F
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL553463
PubChem CID	42640291
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 166174 0 0 0 0 0 0 0 0999 V2000 -9.5108 -2.0162 -4.7086 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4252 -1.8604 -3.8643 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8793 -1.2004 -2.5550 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7484 -1.0758 -1.7694 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0097 -0.6633 -0.4878 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8995 -0.0619 0.0675 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4968 -0.6761 1.2488 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2843 -0.0029 1.8668 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1677 -0.0181 1.0766 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5108 1.1808 1.0363 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3230 1.1539 0.3098 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1073 1.5745 0.7398 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0423 2.0412 1.9150 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1820 1.5452 -0.0470 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0278 2.1741 -1.3869 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1520 1.5473 -2.1684 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1318 0.0650 -2.2009 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5227 -0.6156 -1.0346 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5221 0.1038 -0.2723 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9127 -0.0897 -0.6291 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3294 -1.0476 -1.4516 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7465 -1.2855 -1.8416 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7151 -0.6976 -0.8709 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0786 -0.1858 0.3833 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9836 0.7729 -0.0634 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4902 1.6788 1.0160 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2009 2.3337 0.7233 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3269 3.5843 0.1094 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5244 1.6612 -1.1605 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4789 -1.2412 1.2652 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0924 0.5506 1.2159 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3024 -0.3052 1.5206 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8961 -0.6970 0.1630 C 0 0 2 0 0 0 0 0 0 0 0 0 5.9668 -1.5339 -0.6516 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7326 -2.9228 -0.2256 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6203 -1.5822 -2.0447 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9756 -2.1668 -2.0353 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8414 -1.9293 -0.8606 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3045 -1.1494 0.2748 C 0 0 2 0 0 0 0 0 0 0 0 0 8.5546 -1.9815 1.5466 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1565 0.0817 0.5101 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6513 1.2236 0.5225 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5210 -0.0013 0.7214 O 0 0 0 0 0 0 0 0 0 0 0 0 11.3527 1.1358 0.9447 C 0 0 2 0 0 0 0 0 0 0 0 0 12.2941 1.3108 -0.0307 O 0 0 0 0 0 0 0 0 0 0 0 0 13.4749 0.6297 0.1388 C 0 0 2 0 0 0 0 0 0 0 0 0 13.3773 -0.8592 -0.0329 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9324 -1.1982 -1.3132 O 0 0 0 0 0 0 0 0 0 0 0 0 14.1735 0.9618 1.4296 C 0 0 2 0 0 0 0 0 0 0 0 0 13.2287 0.6349 2.5657 C 0 0 1 0 0 0 0 0 0 0 0 0 11.8435 1.1401 2.3511 C 0 0 1 0 0 0 0 0 0 0 0 0 11.7215 2.4226 2.8891 O 0 0 0 0 0 0 0 0 0 0 0 0 13.2786 -0.7083 2.9070 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4742 2.3169 1.4020 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4660 -3.1320 -0.4323 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3457 -0.3315 -3.4646 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5431 -0.4214 -2.4817 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4626 2.1507 0.3029 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5703 2.4411 1.2947 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7082 1.3774 2.3311 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1066 1.7049 3.5380 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7192 2.7077 0.5753 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7440 3.2695 -0.0335 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1667 0.3203 -0.4199 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.4090 1.0340 -1.7137 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3954 0.1530 -2.9205 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6665 0.0217 -3.4919 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5390 2.1265 -1.8642 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3439 -0.2914 0.0124 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7863 0.2275 1.2121 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.8262 -0.6773 2.2440 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7748 -1.6648 2.1385 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.0446 -2.9916 1.9493 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2063 -3.2421 3.0516 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.7515 -1.4831 1.0120 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.2350 -0.0614 0.8993 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.1248 0.9282 1.1048 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.3229 1.5996 2.3272 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.7584 0.0943 -0.3893 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.8558 -2.3142 1.2982 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3175 -2.3480 -4.2523 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6780 -1.1821 -4.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9831 -2.8394 -3.6400 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6505 -1.8682 -2.1171 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3363 -1.5484 0.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3613 -0.6520 1.9419 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2677 -1.7577 1.0319 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0524 -0.5753 2.8000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3134 1.5674 2.0586 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8542 2.1112 -2.0147 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2708 3.2636 -1.2910 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0469 1.9663 -3.2183 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0919 1.9945 -1.8097 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1960 -1.6468 -1.2524 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3872 -0.8102 -0.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4564 -0.3280 0.8040 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6078 -1.7013 -1.8696 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8663 -0.9299 -2.8830 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8620 -2.4032 -1.9346 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1316 0.2125 -1.4041 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2649 2.4999 1.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4732 1.2069 2.0199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7453 2.5994 1.7301 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6137 4.2034 0.3735 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9527 2.6423 -1.1767 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3823 1.2669 -2.1785 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5636 2.0122 -0.9452 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1509 -0.6943 2.2023 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5969 -1.7447 0.8757 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2528 -1.9323 1.6592 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4552 1.4890 0.7995 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6087 0.7792 2.1905 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0486 0.3697 1.9925 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0795 -1.1744 2.1385 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9337 0.2975 -0.3864 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2668 -3.6679 -0.8935 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6702 -3.2712 -0.2756 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0853 -3.1885 0.7896 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9119 -2.2134 -2.6586 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5388 -0.5615 -2.4767 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8507 -3.2866 -2.1449 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4526 -1.8756 -3.0205 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7460 -1.3712 -1.2654 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6592 -1.8935 1.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0478 -1.5889 2.4233 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4086 -3.0633 1.3516 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6352 2.0105 0.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1650 0.9859 -0.6821 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4031 -1.2685 0.0701 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7646 -1.3524 0.7299 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1776 -2.1649 -1.4331 H 0 0 0 0 0 0 0 0 0 0 0 0 15.0838 0.3716 1.5138 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6479 1.2009 3.4513 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1652 0.4733 2.9480 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6123 2.8639 2.7468 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9701 -0.8491 3.5844 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4074 2.4331 1.7559 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0239 -3.4762 -1.2005 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9023 0.0245 -4.3623 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6159 0.2100 -3.4205 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1338 -1.4057 -3.4880 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5810 -1.2280 -3.2365 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2082 0.3928 -2.8399 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9628 -0.8845 -1.5451 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8128 1.6116 -0.5849 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2497 3.3814 1.8233 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8125 1.3187 2.5694 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0050 2.6889 3.5481 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9699 3.6844 0.5934 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9822 3.5089 -0.9671 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9026 1.0839 0.3364 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4308 1.4794 -1.6446 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7170 0.5939 -3.6828 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3079 0.6759 -3.0827 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8938 2.8544 -1.2866 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0563 1.0209 1.5220 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3152 -1.7335 3.1199 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8250 -3.7905 1.9357 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4291 -2.9763 1.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9889 -4.2098 3.0855 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2884 -1.8559 0.0834 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.0698 0.0716 1.6437 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1072 1.7058 0.3277 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4647 1.6771 2.8414 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.4809 0.7866 -0.3162 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.4374 -1.8839 1.9739 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 2 0 14 12 1 1 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 2 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 27 28 1 0 25 29 1 6 24 30 1 1 24 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 1 34 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 1 39 41 1 0 41 42 2 0 41 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 50 53 1 0 49 54 1 0 38 55 1 0 17 56 1 0 17 57 1 0 10 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 59 62 1 0 58 63 1 0 5 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 65 68 1 0 64 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 72 75 1 0 75 76 1 0 76 77 1 0 77 78 1 0 76 79 1 0 75 80 1 0 66 3 1 0 77 70 1 0 60 8 1 0 27 14 1 0 39 33 1 0 51 44 1 0 19 14 1 0 25 20 1 0 34 23 1 0 1 81 1 0 2 82 1 0 2 83 1 0 3 84 1 1 5 85 1 1 7 86 1 0 7 87 1 0 8 88 1 1 10 89 1 1 15 90 1 0 15 91 1 0 16 92 1 0 16 93 1 0 18 94 1 0 18 95 1 0 19 96 1 1 21 97 1 0 22 98 1 0 22 99 1 0 23100 1 6 26101 1 0 26102 1 0 27103 1 1 28104 1 0 29105 1 0 29106 1 0 29107 1 0 30108 1 0 30109 1 0 30110 1 0 31111 1 0 31112 1 0 32113 1 0 32114 1 0 33115 1 6 35116 1 0 35117 1 0 35118 1 0 36119 1 0 36120 1 0 37121 1 0 37122 1 0 38123 1 6 40124 1 0 40125 1 0 40126 1 0 44127 1 1 46128 1 6 47129 1 0 47130 1 0 48131 1 0 49132 1 1 50133 1 1 51134 1 1 52135 1 0 53136 1 0 54137 1 0 55138 1 0 56139 1 0 56140 1 0 56141 1 0 57142 1 0 57143 1 0 57144 1 0 58145 1 6 59146 1 1 60147 1 1 61148 1 0 62149 1 0 63150 1 0 64151 1 1 65152 1 1 66153 1 6 67154 1 0 68155 1 0 70156 1 1 72157 1 1 73158 1 0 73159 1 0 74160 1 0 75161 1 6 76162 1 1 77163 1 6 78164 1 0 79165 1 0 80166 1 0 M END

Standard InCHIKey	VBBKYJHEVPBGBQ-MSXWTUGRSA-N
Standard InCHI	InChI=1S/C54H86O26/c1-49(2)13-14-54(48(72)80-45-41(70)37(66)34(63)26(77-45)20-73-46-42(38(67)33(62)25(19-57)76-46)78-43-39(68)35(64)31(60)23(17-55)74-43)22(15-49)21-7-8-27-50(3)11-10-29(58)53(6,28(50)9-12-51(27,4)52(21,5)16-30(54)59)47(71)79-44-40(69)36(65)32(61)24(18-56)75-44/h7,22-46,55-70H,8-20H2,1-6H3/t22-,23+,24+,25+,26+,27+,28+,29-,30+,31+,32+,33+,34+,35-,36-,37-,38-,39+,40+,41+,42+,43-,44-,45-,46+,50+,51+,52+,53-,54+/m0/s1
SMILES	OC[C@H]1O[C@@H](OC[C@H]2O[C@@H](OC(=O)[C@@]34CCC(C[C@H]4C4=CC[C@H]5[C@@]([C@@]4(C[C@H]3O)C)(C)CC[C@@H]3[C@]5(C)CC[C@@H]([C@@]3(C)C(=O)O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)O)(C)C)[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1150.54	Volume:	1086.168 ? Van der Waals volume.
Dense:	1.059	LogP:	-0.819 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.381 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.506 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	52.0
TPSA:	431.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	16.0	Rings:	9.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.065	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.006	Fsp³:	0.926
MCE-18:	202.154 ? 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:	0.67	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.015 ? 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:	0.224	Promiscuous compounds:	0.162

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.853	MDCK Permeability:	-5.023
Pgp-inhibitor:	0.0	Pgp-substrate:	0.179
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):	0.999
20% Bioavailability (F20%):	0.873	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.797	MRP1:	0.003
Plasma Protein Binding (PPB):	64.037%	Volume Distribution (VD):	-0.256
Fu:	19.556% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.003
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:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.034
HLM stability:	0.0 ? 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):

-0.731

Half-life (T1/2):

5.065

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.801	Drug-induced Liver Injury (DILI):	0.984
AMES Toxicity:	0.994	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.125	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.785	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.85	RPMI-8226 Immunitoxicity:	0.271
A549 Cytotoxicity:	0.945	Hek293 Cytotoxicity:	0.196
BCF:	0.554 ? 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:	3.287 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.947 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.849 ? 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
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19290648]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	aerial parts	Changqing, Shangdong Province, China	2004-JUN	PMID[19290648]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	4

Activity Type	# Activity
Cell line	3
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
NPT1855	Cell line	HFL1	Homo sapiens	IC50	=	4400.0	nM	PMID[19290648]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[19290648]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[19290648]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	9700.0	nM	PMID[19290648]

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 NPC305267 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	22415
0.1-0.2	22324
0.2-0.3	3772
0.3-0.4	835
0.4-0.5	357
0.5-0.6	127
0.6-0.7	20
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
0.8958	High Similarity	NPC69811
0.819	Intermediate Similarity	NPC25663
0.7522	Intermediate Similarity	NPC476991
0.6634	Remote Similarity	NPC475208
0.6535	Remote Similarity	NPC1046
0.6449	Remote Similarity	NPC164389
0.6442	Remote Similarity	NPC480420
0.6422	Remote Similarity	NPC64715
0.6373	Remote Similarity	NPC29069
0.6372	Remote Similarity	NPC476992
0.6296	Remote Similarity	NPC488526
0.626	Remote Similarity	NPC220160
0.6162	Remote Similarity	NPC48249
0.6142	Remote Similarity	NPC33012
0.6129	Remote Similarity	NPC51564
0.6121	Remote Similarity	NPC123522
0.6102	Remote Similarity	NPC283417
0.6102	Remote Similarity	NPC200049
0.6091	Remote Similarity	NPC63159
0.6063	Remote Similarity	NPC8524
0.6053	Remote Similarity	NPC104137
0.6053	Remote Similarity	NPC26626
0.6	Remote Similarity	NPC48499
0.5984	Remote Similarity	NPC475514
0.5962	Remote Similarity	NPC238935
0.595	Remote Similarity	NPC21691
0.5918	Remote Similarity	NPC167383
0.5913	Remote Similarity	NPC207738
0.5872	Remote Similarity	NPC469946
0.5868	Remote Similarity	NPC4749
0.5862	Remote Similarity	NPC815
0.5856	Remote Similarity	NPC473459
0.5854	Remote Similarity	NPC470876
0.5804	Remote Similarity	NPC105800
0.58	Remote Similarity	NPC237503
0.578	Remote Similarity	NPC295371
0.5726	Remote Similarity	NPC75287
0.5691	Remote Similarity	NPC473386
0.5625	Remote Similarity	NPC104071
0.561	Remote Similarity	NPC85154
0.5593	Remote Similarity	NPC11242
0.5583	Remote Similarity	NPC79643
0.5575	Remote Similarity	NPC102439
0.5575	Remote Similarity	NPC232237
0.5574	Remote Similarity	NPC480423
0.5536	Remote Similarity	NPC112352
0.552	Remote Similarity	NPC473452
0.552	Remote Similarity	NPC13998
0.552	Remote Similarity	NPC286457
0.5504	Remote Similarity	NPC482010
0.55	Remote Similarity	NPC610204
0.5492	Remote Similarity	NPC135904
0.5492	Remote Similarity	NPC123199
0.5487	Remote Similarity	NPC309714
0.5481	Remote Similarity	NPC489208
0.5478	Remote Similarity	NPC222580
0.5478	Remote Similarity	NPC123796
0.5478	Remote Similarity	NPC488517
0.547	Remote Similarity	NPC481079
0.5469	Remote Similarity	NPC309223
0.5447	Remote Similarity	NPC191827
0.5431	Remote Similarity	NPC471435
0.5431	Remote Similarity	NPC471434
0.542	Remote Similarity	NPC102505
0.542	Remote Similarity	NPC488514
0.5417	Remote Similarity	NPC185466
0.5403	Remote Similarity	NPC471577
0.5366	Remote Similarity	NPC603137
0.5349	Remote Similarity	NPC302543
0.5349	Remote Similarity	NPC144644
0.5349	Remote Similarity	NPC170407
0.5345	Remote Similarity	NPC297263
0.5323	Remote Similarity	NPC470218
0.5319	Remote Similarity	NPC488519
0.5312	Remote Similarity	NPC293330
0.5312	Remote Similarity	NPC65105
0.5312	Remote Similarity	NPC43550
0.5304	Remote Similarity	NPC148603
0.5304	Remote Similarity	NPC480475
0.5268	Remote Similarity	NPC150400
0.5267	Remote Similarity	NPC142151
0.5263	Remote Similarity	NPC489209
0.5252	Remote Similarity	NPC484831
0.5252	Remote Similarity	NPC484830
0.525	Remote Similarity	NPC31838
0.5246	Remote Similarity	NPC60557
0.5246	Remote Similarity	NPC76972
0.5246	Remote Similarity	NPC469782
0.5246	Remote Similarity	NPC67857
0.5246	Remote Similarity	NPC204414
0.5238	Remote Similarity	NPC604133
0.5234	Remote Similarity	NPC41061
0.5234	Remote Similarity	NPC227551
0.5231	Remote Similarity	NPC37860
0.5229	Remote Similarity	NPC214484
0.5227	Remote Similarity	NPC250247
0.5221	Remote Similarity	NPC470512
0.5221	Remote Similarity	NPC39211
0.5205	Remote Similarity	NPC23020
0.5191	Remote Similarity	NPC70809
0.5188	Remote Similarity	NPC68767
0.5179	Remote Similarity	NPC475516
0.5175	Remote Similarity	NPC473343
0.5172	Remote Similarity	NPC251768
0.5172	Remote Similarity	NPC485563
0.5169	Remote Similarity	NPC302887
0.5167	Remote Similarity	NPC160452
0.5154	Remote Similarity	NPC135849
0.5154	Remote Similarity	NPC305981
0.5152	Remote Similarity	NPC267694
0.5149	Remote Similarity	NPC153673
0.5149	Remote Similarity	NPC51099
0.5143	Remote Similarity	NPC306746
0.5133	Remote Similarity	NPC473373
0.513	Remote Similarity	NPC192791
0.513	Remote Similarity	NPC223301
0.513	Remote Similarity	NPC171544
0.5126	Remote Similarity	NPC104372
0.5124	Remote Similarity	NPC481078
0.5122	Remote Similarity	NPC610461
0.5116	Remote Similarity	NPC471580
0.5116	Remote Similarity	NPC258617
0.5115	Remote Similarity	NPC261506
0.5115	Remote Similarity	NPC298034
0.5115	Remote Similarity	NPC71065
0.5115	Remote Similarity	NPC4328
0.5105	Remote Similarity	NPC233223
0.5105	Remote Similarity	NPC183816
0.5105	Remote Similarity	NPC43589
0.5098	Remote Similarity	NPC191763
0.5086	Remote Similarity	NPC30289
0.5085	Remote Similarity	NPC470513
0.5083	Remote Similarity	NPC301449
0.5083	Remote Similarity	NPC601290
0.5083	Remote Similarity	NPC606145
0.5081	Remote Similarity	NPC151543
0.5079	Remote Similarity	NPC475160
0.5079	Remote Similarity	NPC100639
0.5079	Remote Similarity	NPC473714
0.5075	Remote Similarity	NPC293031
0.5043	Remote Similarity	NPC173859
0.5041	Remote Similarity	NPC295823
0.5041	Remote Similarity	NPC174720
0.5041	Remote Similarity	NPC241909
0.5041	Remote Similarity	NPC213952
0.5041	Remote Similarity	NPC475467
0.5037	Remote Similarity	NPC110385
0.5036	Remote Similarity	NPC275225
0.5036	Remote Similarity	NPC480421
0.5035	Remote Similarity	NPC484829

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC305267 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7472
0.1-0.2	1617
0.2-0.3	57
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