NPASS Compound

Natural Product: NPC473386

Natural Product ID	NPC473386
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2S,3R,4S,5S)-3,4,5-Trihydroxyoxan-2-Yl]Oxyoxan-2-Yl]Oxy-3,5-Dihydroxyoxan-2-Yl]Oxy-3,4-Dihydroxy-6-Methyloxan-2-Yl]Oxy-4,5-Dihydroxy-6-Methyloxan-2-Yl] (4Ar,5R,6As,6Br,8Ar,9S,10S,12Ar,14Bs)-9-Formyl-5,10-Dihydroxy-2,2,6A,6B,9,12A-Hexamethyl-1,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydropicene-4A-Carboxylate
IUPAC Name	[(2S,3R,4S,5R,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4S,5R)-4-[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-methyloxan-2-yl] (4aR,5R,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-5,10-dihydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL405491
PubChem CID	44451309
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 172181 0 0 0 0 0 0 0 0999 V2000 -13.8495 2.7145 0.8518 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.1495 1.7572 0.6816 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.3515 1.5173 -0.5805 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.6082 2.6439 -1.4997 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9100 0.2354 -1.1595 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.2650 0.3473 -1.4693 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1063 -0.2704 -2.3241 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.7157 -0.5725 -1.8313 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0641 0.6592 -1.1888 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9510 1.2808 -0.1636 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2603 2.4846 0.4009 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9131 2.2352 0.9604 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1035 1.1688 0.3091 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8688 0.1215 -0.4121 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9950 -0.7606 -1.2281 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7634 -1.0770 -0.4824 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4434 -0.5398 0.6933 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3008 0.4526 1.3957 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2680 -0.2046 2.3260 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4955 1.4549 2.1739 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0447 1.1974 2.2732 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5837 1.8483 3.4442 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6399 -0.2477 2.4150 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1295 -1.0280 1.2608 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1170 -2.5144 1.4043 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2715 -3.0699 2.7621 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5714 -2.1205 3.8494 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9576 -0.7903 3.7776 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4297 -4.0835 2.7230 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0500 -3.8921 3.1986 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1280 -0.2425 2.3146 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4108 -0.7678 3.1958 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4900 0.3412 1.2453 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0923 0.3924 1.0362 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6658 1.6774 1.1923 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7468 2.5520 0.1716 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.9788 3.4306 0.1613 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5921 1.9860 -1.2166 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2687 0.6446 -1.3628 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6772 -0.2220 -0.2530 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6951 -0.2485 -0.3594 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1808 -1.5082 -0.6971 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0370 -1.9498 0.2809 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1622 -1.1539 0.4515 C 0 0 1 0 0 0 0 0 0 0 0 0 3.9889 -1.6842 1.6011 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9415 -1.1604 -0.8209 C 0 0 1 0 0 0 0 0 0 0 0 0 3.0588 -0.4991 -1.8671 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8908 -1.4881 -2.0344 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4279 -2.7455 -2.2637 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6584 -0.3766 -3.1001 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2167 -0.6945 -0.7697 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1780 -1.5839 -1.2024 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9805 -1.9238 -0.1085 O 0 0 0 0 0 0 0 0 0 0 0 0 7.6930 -3.1037 -0.3661 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2695 -3.1004 -1.7659 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4735 -1.6815 -2.1924 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0974 -1.0044 -2.2385 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6014 -1.2552 -3.5257 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1882 -1.0441 -1.1532 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2873 -0.3710 -1.6352 C 0 0 2 0 0 0 0 0 0 0 0 0 11.4114 -1.0003 -1.0433 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5124 -0.4228 -1.6861 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7865 0.9475 -1.1139 C 0 0 1 0 0 0 0 0 0 0 0 0 11.5361 1.4248 -0.3992 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2895 1.0564 -1.1827 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2091 1.9155 -2.2977 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4753 0.7673 0.8221 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8237 0.9340 -0.1999 O 0 0 0 0 0 0 0 0 0 0 0 0 14.8466 1.8105 -0.5062 C 0 0 2 0 0 0 0 0 0 0 0 0 15.9541 0.9964 -0.8516 O 0 0 0 0 0 0 0 0 0 0 0 0 16.2530 0.1052 0.1642 C 0 0 0 0 0 0 0 0 0 0 0 0 16.8026 0.8521 1.3835 C 0 0 1 0 0 0 0 0 0 0 0 0 15.7296 1.7971 1.8284 C 0 0 1 0 0 0 0 0 0 0 0 0 15.2893 2.6403 0.6633 C 0 0 1 0 0 0 0 0 0 0 0 0 16.3379 3.4639 0.2614 O 0 0 0 0 0 0 0 0 0 0 0 0 14.6254 1.1060 2.3601 O 0 0 0 0 0 0 0 0 0 0 0 0 17.1021 -0.0129 2.4094 O 0 0 0 0 0 0 0 0 0 0 0 0 7.4048 -3.7816 -2.6294 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6337 0.6969 -1.2173 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1168 2.8408 -2.1697 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0707 1.7855 -0.6269 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6879 1.5665 -2.3072 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0511 0.9949 1.4455 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8052 3.3747 -1.6288 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9171 2.3064 -2.5341 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.5036 3.2485 -1.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8311 -0.5329 -0.3469 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7713 0.1909 -0.6473 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5448 -1.2444 -2.6293 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1164 0.3817 -3.1987 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7269 -1.4065 -1.1321 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0923 -0.7826 -2.7458 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0110 0.5353 0.6882 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9305 2.8788 1.2223 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2314 3.3386 -0.3341 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9835 2.1181 2.0819 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3302 3.2026 0.8629 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3372 -0.5453 0.3753 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5277 -1.7495 -1.3722 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7875 -0.4137 -2.2535 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1021 -1.8106 -0.9795 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1642 -1.3161 2.1839 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2976 0.1294 2.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9385 -0.0431 3.3951 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6225 2.4704 1.6987 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9177 1.5939 3.2059 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4131 1.6242 1.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5872 1.8315 3.4640 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4139 -0.8030 0.4015 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1535 -2.9309 0.9849 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8911 -2.9237 0.6897 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6926 -2.0155 3.9449 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2869 -2.6139 4.8270 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6574 -0.0411 4.2546 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0640 -0.7627 4.4636 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3625 -4.6888 3.6668 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3168 -4.7974 1.9003 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4079 -3.5614 2.7323 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4064 -4.7017 3.8418 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5225 -4.2786 2.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3579 -3.2654 3.8001 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5649 -0.1764 1.8639 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1182 3.2770 0.2893 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0269 4.0773 1.0635 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9104 2.8788 0.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8505 4.1532 -0.6973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4829 1.8471 -1.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9278 0.2050 -2.3216 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0335 -1.2557 -0.4211 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3629 -2.2547 -0.8001 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7540 -0.1305 0.6884 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4806 -2.6111 1.2657 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8100 -0.9356 1.8045 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4041 -1.8484 2.5081 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0105 -2.2327 -1.1771 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5956 0.4340 -1.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2556 -1.2130 -2.8730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1307 -3.4357 -1.6224 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6873 -1.2976 -3.5076 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7523 -2.5471 -1.5503 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0583 -4.0127 -0.1979 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5289 -3.1247 0.3457 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2663 -3.5926 -1.7903 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9265 -1.5308 -3.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2891 0.0705 -2.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4681 -0.3687 -3.9873 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3774 -0.4416 -2.7497 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2324 -0.3036 -2.7437 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3937 -1.0732 -1.6374 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9421 1.6508 -1.9505 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5163 2.5004 -0.2241 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3766 1.2340 -0.5741 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6894 2.7386 -2.0675 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5748 0.7928 1.2077 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6565 2.4012 -1.4281 H 0 0 0 0 0 0 0 0 0 0 0 0 16.9485 -0.6615 -0.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 15.3068 -0.3923 0.4664 H 0 0 0 0 0 0 0 0 0 0 0 0 17.6737 1.4810 1.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 16.1173 2.4969 2.6170 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4857 3.3093 1.0436 H 0 0 0 0 0 0 0 0 0 0 0 0 16.7345 3.1063 -0.5544 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8792 0.1456 2.3859 H 0 0 0 0 0 0 0 0 0 0 0 0 17.4026 -0.8699 1.9913 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7361 -3.6594 -3.5661 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1171 1.0106 -2.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3325 2.2946 -2.9708 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2637 2.8938 -0.6746 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1059 1.4028 -1.6426 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0451 1.6783 -0.2662 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2007 2.4975 -2.0326 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0260 1.0156 -3.0068 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6246 1.7344 -2.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 1 6 3 5 1 0 5 6 1 0 5 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 2 0 17 18 1 0 18 19 1 1 18 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 26 30 1 0 23 31 1 6 31 32 2 0 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 36 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 47 50 1 0 46 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 56 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 64 67 1 0 63 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 71 72 1 0 72 73 1 0 73 74 1 0 74 75 1 0 73 76 1 0 72 77 1 0 55 78 1 0 39 79 1 0 38 80 1 0 13 81 1 6 9 82 1 6 10 3 1 0 18 13 1 0 28 23 1 0 40 34 1 0 48 42 1 0 57 52 1 0 65 60 1 0 74 69 1 0 14 9 1 0 24 17 1 0 2 83 1 0 4 84 1 0 4 85 1 0 4 86 1 0 5 87 1 1 6 88 1 0 7 89 1 0 7 90 1 0 8 91 1 0 8 92 1 0 10 93 1 1 11 94 1 0 11 95 1 0 12 96 1 0 12 97 1 0 14 98 1 0 15 99 1 0 15100 1 0 16101 1 0 19102 1 0 19103 1 0 19104 1 0 20105 1 0 20106 1 0 21107 1 6 22108 1 0 24109 1 6 25110 1 0 25111 1 0 27112 1 0 27113 1 0 28114 1 0 28115 1 0 29116 1 0 29117 1 0 29118 1 0 30119 1 0 30120 1 0 30121 1 0 34122 1 1 36123 1 1 37124 1 0 37125 1 0 37126 1 0 38127 1 6 39128 1 6 40129 1 1 42130 1 6 44131 1 1 45132 1 0 45133 1 0 45134 1 0 46135 1 6 47136 1 1 48137 1 6 49138 1 0 50139 1 0 52140 1 6 54141 1 0 54142 1 0 55143 1 1 56144 1 6 57145 1 1 58146 1 0 60147 1 6 62148 1 0 62149 1 0 63150 1 6 64151 1 1 65152 1 1 66153 1 0 67154 1 0 69155 1 6 71156 1 0 71157 1 0 72158 1 6 73159 1 1 74160 1 1 75161 1 0 76162 1 0 77163 1 0 78164 1 0 79165 1 0 80166 1 0 81167 1 0 81168 1 0 81169 1 0 82170 1 0 82171 1 0 82172 1 0 M END

Standard InCHIKey	OFOINNASBFYBOI-DVYRPRCTSA-N
Standard InCHI	InChI=1S/C57H90O25/c1-23-34(63)37(66)45(81-49-41(70)38(67)43(24(2)77-49)79-48-42(71)44(28(60)20-74-48)80-47-40(69)36(65)29(21-75-47)78-46-39(68)35(64)27(59)19-73-46)50(76-23)82-51(72)57-16-15-52(3,4)17-26(57)25-9-10-31-53(5)13-12-32(61)54(6,22-58)30(53)11-14-55(31,7)56(25,8)18-33(57)62/h9,22-24,26-50,59-71H,10-21H2,1-8H3/t23-,24+,26+,27+,28-,29+,30-,31?,32+,33-,34+,35+,36+,37+,38+,39-,40-,41-,42-,43+,44+,45-,46+,47+,48+,49+,50+,53+,54+,55-,56-,57-/m1/s1
SMILES	O=C[C@]1(C)[C@@H](O)CC[C@]2([C@H]1CC[C@@]1(C2CC=C2[C@@]1(C)C[C@@H](O)[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O[C@@H]1O[C@H](C)[C@@H]([C@@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O)O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1174.58	Volume:	1120.709 ? Van der Waals volume.
Dense:	1.048	LogP:	0.967 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.607 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.174 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	58.0
TPSA:	389.43 ? Topological Polar Surface Area.	H-Bond Acceptor:	25.0
H-Bond Donor:	13.0	Rings:	10.0
Heavy Atoms:	25.0

MedChem Properties

QED Drug-Likeness Score:	0.06	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.301	Fsp³:	0.93
MCE-18:	217.0 ? 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:	0.682	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.249	Promiscuous compounds:	0.102

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.602	MDCK Permeability:	-5.105
Pgp-inhibitor:	0.0	Pgp-substrate:	0.999
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):	0.952
20% Bioavailability (F20%):	0.993	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.006	MRP1:	0.11
Plasma Protein Binding (PPB):	63.517%	Volume Distribution (VD):	-0.327
Fu:	22.732% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.999	BCRP inhibitor:	0.001
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:	0.851
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.044
HLM stability:	0.69 ? 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):

-0.366

Half-life (T1/2):

3.369

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.003
Human Hepatotoxicity (H-HT):	0.87	Drug-induced Liver Injury (DILI):	0.939
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.019
Maximum Recommended Daily Dose:	0.013	Skin Sensitization:	1.0
Carcinogencity:	0.203	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.999
Hematotoxicity:	0.746	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.997	RPMI-8226 Immunitoxicity:	0.62
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.933
BCF:	0.815 ? 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:	3.577 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.364 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.347 ? 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
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[16880670]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	root	n.a.	PMID[17409564]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	roots	n.a.	n.a.	PMID[18194870]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25660	Gypsophila oldhamiana	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25660	Gypsophila oldhamiana	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	1

Activity Type	# Activity
Others	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
NPT2	Others	Unspecified	n.a.	IC50	=	78500.0	nM	PMID[21982797]

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 NPC473386 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	25163
0.1-0.2	21266
0.2-0.3	2623
0.3-0.4	516
0.4-0.5	179
0.5-0.6	76
0.6-0.7	23
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
0.8571	High Similarity	NPC471577
0.812	Intermediate Similarity	NPC471580
0.7917	Intermediate Similarity	NPC309223
0.7661	Intermediate Similarity	NPC102505
0.7661	Intermediate Similarity	NPC488514
0.7583	Intermediate Similarity	NPC13998
0.6992	Remote Similarity	NPC85154
0.6617	Remote Similarity	NPC8524
0.6567	Remote Similarity	NPC33012
0.6565	Remote Similarity	NPC224381
0.6412	Remote Similarity	NPC144644
0.6412	Remote Similarity	NPC170407
0.6397	Remote Similarity	NPC480421
0.6345	Remote Similarity	NPC485563
0.6288	Remote Similarity	NPC37860
0.626	Remote Similarity	NPC104137
0.626	Remote Similarity	NPC26626
0.6242	Remote Similarity	NPC472270
0.6242	Remote Similarity	NPC112492
0.6241	Remote Similarity	NPC70809
0.6222	Remote Similarity	NPC68767
0.6183	Remote Similarity	NPC470876
0.6172	Remote Similarity	NPC480423
0.6154	Remote Similarity	NPC237191
0.6107	Remote Similarity	NPC473452
0.6107	Remote Similarity	NPC286457
0.6103	Remote Similarity	NPC293031
0.608	Remote Similarity	NPC815
0.6061	Remote Similarity	NPC475514
0.5956	Remote Similarity	NPC220160
0.5938	Remote Similarity	NPC123522
0.5926	Remote Similarity	NPC33068
0.5828	Remote Similarity	NPC23020
0.5798	Remote Similarity	NPC480420
0.5794	Remote Similarity	NPC69811
0.5793	Remote Similarity	NPC297950
0.5758	Remote Similarity	NPC488560
0.5753	Remote Similarity	NPC472268
0.5725	Remote Similarity	NPC142151
0.5714	Remote Similarity	NPC153673
0.5691	Remote Similarity	NPC488526
0.5691	Remote Similarity	NPC305267
0.5612	Remote Similarity	NPC267694
0.5603	Remote Similarity	NPC110385
0.5603	Remote Similarity	NPC51099
0.5594	Remote Similarity	NPC275225
0.5565	Remote Similarity	NPC473459
0.5563	Remote Similarity	NPC480422
0.552	Remote Similarity	NPC105800
0.5479	Remote Similarity	NPC489208
0.544	Remote Similarity	NPC164389
0.5366	Remote Similarity	NPC488513
0.5333	Remote Similarity	NPC475160
0.5333	Remote Similarity	NPC329893
0.5333	Remote Similarity	NPC473714
0.5287	Remote Similarity	NPC472269
0.5286	Remote Similarity	NPC202828
0.5286	Remote Similarity	NPC119592
0.5286	Remote Similarity	NPC236638
0.5286	Remote Similarity	NPC294453
0.5282	Remote Similarity	NPC482010
0.5267	Remote Similarity	NPC484831
0.5259	Remote Similarity	NPC257211
0.5259	Remote Similarity	NPC480419
0.5248	Remote Similarity	NPC302543
0.5248	Remote Similarity	NPC476991
0.5231	Remote Similarity	NPC481079
0.5207	Remote Similarity	NPC1046
0.5203	Remote Similarity	NPC475368
0.5195	Remote Similarity	NPC475584
0.5195	Remote Similarity	NPC475152
0.5192	Remote Similarity	NPC311178
0.5192	Remote Similarity	NPC478559
0.5192	Remote Similarity	NPC478560
0.5177	Remote Similarity	NPC481081
0.5172	Remote Similarity	NPC489209
0.5166	Remote Similarity	NPC484830
0.5163	Remote Similarity	NPC475394
0.5152	Remote Similarity	NPC207738
0.5149	Remote Similarity	NPC300419
0.5145	Remote Similarity	NPC4749
0.5145	Remote Similarity	NPC481080
0.5139	Remote Similarity	NPC250247
0.5118	Remote Similarity	NPC104071
0.5108	Remote Similarity	NPC476068
0.5103	Remote Similarity	NPC478825
0.5078	Remote Similarity	NPC102439
0.5078	Remote Similarity	NPC232237
0.5076	Remote Similarity	NPC295823
0.5076	Remote Similarity	NPC174720
0.5076	Remote Similarity	NPC241909
0.5076	Remote Similarity	NPC475467
0.5072	Remote Similarity	NPC25663
0.5069	Remote Similarity	NPC478823
0.5065	Remote Similarity	NPC484829
0.5063	Remote Similarity	NPC222951
0.504	Remote Similarity	NPC173583
0.5035	Remote Similarity	NPC261506
0.5035	Remote Similarity	NPC298034
0.5035	Remote Similarity	NPC71065
0.5035	Remote Similarity	NPC4328
0.5032	Remote Similarity	NPC233223
0.5032	Remote Similarity	NPC183816
0.5032	Remote Similarity	NPC43589
0.5031	Remote Similarity	NPC488619

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC473386 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7901
0.1-0.2	1219
0.2-0.3	28
0.3-0.4	2
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