NPASS Compound

Natural Product: NPC471580

Natural Product ID	NPC471580
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-Keto,16A-Hydroxy,24-Noroleanolic Acid 28-O-Alpha-L-Arabinopyranosyl-(1->4)-Alpha-L-Arabinopyranosyl-(1->3)-Beta-D-Xylopyranosyl-(1->4)-A-L-Rhamnopyranosyl-(1->2)-Beta-D-Fucopyranosyl Ester
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,8aS,9S,12aS,14bS)-5-hydroxy-2,2,6a,6b,9,12a-hexamethyl-10-oxo-1,3,4,5,6,6a,7,8,8a,9,11,12,13,14b-tetradecahydropicene-4a-carboxylate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL261873
PubChem CID	44451458
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 168177 0 0 0 0 0 0 0 0999 V2000 3.0316 -3.4210 0.1471 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0355 -2.9663 -0.6816 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9456 -2.1781 0.0502 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4399 -1.3045 -0.9219 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2623 -0.1790 -1.0442 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7400 -0.6383 -1.0503 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7330 -1.9963 -1.6599 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0257 -2.4501 -1.8853 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5224 0.2815 -1.6977 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3292 1.0150 -0.8554 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8993 2.3440 -0.7542 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6726 3.1488 0.0190 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8639 2.6021 0.6861 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4662 1.3405 0.1830 C 0 0 1 0 0 0 0 0 0 0 0 0 5.8053 0.9518 -1.1205 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1921 -0.3482 -1.3938 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8437 1.4307 -0.0044 O 0 0 0 0 0 0 0 0 0 0 0 0 8.5646 0.4974 0.7332 C 0 0 2 0 0 0 0 0 0 0 0 0 9.2874 1.2724 1.6783 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3502 1.9198 1.0566 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4752 0.8837 0.9185 C 0 0 1 0 0 0 0 0 0 0 0 0 10.8113 -0.4570 0.7519 C 0 0 1 0 0 0 0 0 0 0 0 0 9.5579 -0.2667 -0.0697 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1077 -1.5340 -0.4334 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6603 -1.4084 0.1897 O 0 0 0 0 0 0 0 0 0 0 0 0 12.2570 1.2818 -0.1349 O 0 0 0 0 0 0 0 0 0 0 0 0 13.5486 1.6411 0.2458 C 0 0 2 0 0 0 0 0 0 0 0 0 13.8024 2.9798 0.0704 O 0 0 0 0 0 0 0 0 0 0 0 0 14.3122 3.3398 -1.1534 C 0 0 0 0 0 0 0 0 0 0 0 0 15.6785 2.7141 -1.4065 C 0 0 1 0 0 0 0 0 0 0 0 0 15.9077 1.5972 -0.3847 C 0 0 1 0 0 0 0 0 0 0 0 0 14.6193 0.8033 -0.3612 C 0 0 1 0 0 0 0 0 0 0 0 0 14.8547 -0.3074 0.4455 O 0 0 0 0 0 0 0 0 0 0 0 0 16.9437 0.7824 -0.7711 O 0 0 0 0 0 0 0 0 0 0 0 0 15.6509 2.1937 -2.6951 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6654 2.5635 2.0820 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0232 0.6782 0.1952 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0715 -2.9687 0.4907 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4824 -2.8080 1.7676 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9528 -2.6698 1.9037 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3311 -2.4422 3.2451 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9598 -3.5210 4.0466 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.4490 -3.5691 4.0724 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0160 -3.9545 2.6814 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3898 -3.9017 2.7018 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0140 -2.3040 4.4303 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4858 -3.1854 5.4489 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4574 -1.5689 1.1814 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4514 -1.7024 0.2447 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8754 -2.8731 0.0517 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9815 -0.5100 -0.4831 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8019 0.1141 -1.1604 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9939 1.5657 -1.4884 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2395 2.3371 -0.2533 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4001 1.8189 0.4917 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7543 0.3888 0.4065 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2536 0.2242 0.2849 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9623 -0.0022 1.3701 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.4229 -0.1942 1.4840 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0550 0.3043 0.2126 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3022 -0.3339 -0.9329 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9411 0.3107 -1.0325 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0209 -0.3292 -2.0330 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8880 -1.1120 -1.5251 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0641 -1.3968 -2.6615 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1260 1.7346 -1.5055 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1474 -1.8469 -0.6797 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0336 -0.1968 -2.2315 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3345 -1.0191 -2.0426 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1580 -0.1650 -1.1166 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.5368 0.1244 0.1992 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0301 -0.8892 1.2054 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1654 1.4522 0.6737 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.4442 1.7466 -0.0311 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.2875 0.5539 -0.3123 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.4644 0.4677 -0.0753 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.5770 -0.6213 -0.9452 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.2358 -0.8381 -2.2934 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0043 2.5134 0.6160 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5778 3.7767 -0.7098 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0970 -4.3969 0.1632 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5447 -3.7420 -1.2693 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3628 -1.4972 0.8224 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1041 0.3525 -1.9807 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0170 -0.5964 0.0237 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1547 -1.9488 -2.6084 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0819 -3.4329 -1.7420 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1636 0.6109 0.1866 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9140 4.1367 -0.4970 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9709 3.5211 0.8460 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6866 3.3877 0.5809 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2038 0.5293 0.9003 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1090 1.6556 -1.9395 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0374 -0.4287 -1.8872 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8622 -0.1324 1.2867 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0101 2.2729 0.0705 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6578 2.7920 1.6381 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0002 0.9130 1.8962 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4831 -0.7814 1.7747 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8161 0.2675 -1.0168 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8842 -2.0135 0.4024 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4136 -1.5144 0.8394 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5774 1.4766 1.3669 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4509 4.4386 -1.1373 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6088 3.1481 -1.9994 H 0 0 0 0 0 0 0 0 0 0 0 0 16.4457 3.4866 -1.3391 H 0 0 0 0 0 0 0 0 0 0 0 0 16.0616 2.0720 0.6059 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4208 0.5150 -1.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 15.5714 -0.1299 1.0856 H 0 0 0 0 0 0 0 0 0 0 0 0 17.7960 1.1283 -0.4034 H 0 0 0 0 0 0 0 0 0 0 0 0 16.4016 1.5746 -2.8438 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2613 1.8457 2.4650 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9822 1.7337 -0.0873 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0953 0.4108 0.7270 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8429 0.4720 0.9376 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0266 -1.9307 2.2119 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5103 -3.5676 1.5326 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4204 -4.4652 3.7500 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1451 -4.3486 4.7977 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4363 -4.9101 2.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7061 -4.5337 3.3800 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0097 -2.2873 4.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7790 -2.5355 6.0022 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4524 -2.6394 5.3590 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7167 -4.1306 5.9873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8908 0.0627 -0.5268 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5451 -0.4059 -2.1040 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0562 1.8952 -2.0238 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8228 1.6973 -2.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3082 2.4623 0.2650 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2100 2.1509 1.5787 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4974 -0.0106 1.4515 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4345 -0.0637 2.3556 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8099 0.3303 2.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5813 -1.2786 1.6525 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8364 1.3894 0.1724 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6941 0.3845 -2.8453 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6498 -1.0689 -2.6245 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2040 -2.1409 -1.2068 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5996 -2.2639 -2.5506 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4476 2.4507 -0.7643 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7352 1.6948 -2.4330 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1415 2.1462 -1.9036 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0763 -2.4127 -1.6293 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2384 -2.0113 -0.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9714 -2.2683 -0.1032 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4630 -0.5674 -3.0682 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4543 0.8354 -2.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8272 -0.9586 -3.0431 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1467 -2.0331 -1.7127 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2376 0.8386 -1.6507 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1177 -1.9141 0.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4886 -0.8169 2.1716 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0848 -0.6068 1.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4525 2.2806 0.4572 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3069 1.4491 1.7739 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3279 2.3993 -0.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0578 2.3790 0.6793 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7097 -1.5377 -0.3743 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8083 -1.6913 -2.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3022 -1.1010 -2.0639 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2331 0.1010 -2.8557 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1202 2.7867 0.0144 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1480 3.3971 1.3065 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8650 1.6454 1.2840 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6774 4.2651 -1.1420 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3808 3.6897 -1.4657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9985 4.3253 0.1560 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 6 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 14 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 22 25 1 0 21 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 31 34 1 0 30 35 1 0 13 36 1 0 5 37 1 0 3 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 43 46 1 0 42 47 1 0 40 48 1 0 48 49 1 0 49 50 2 0 51 49 1 1 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 2 0 58 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 62 66 1 6 61 67 1 1 61 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 71 72 1 1 71 73 1 0 73 74 1 0 74 75 1 0 75 76 2 0 75 77 1 0 77 78 1 0 54 79 1 0 54 80 1 0 7 2 1 0 15 10 1 0 23 18 1 0 32 27 1 0 44 39 1 0 64 51 1 0 77 70 1 0 56 51 1 0 62 57 1 0 71 60 1 0 1 81 1 0 2 82 1 6 3 83 1 1 5 84 1 6 6 85 1 1 7 86 1 6 8 87 1 0 10 88 1 1 12 89 1 0 12 90 1 0 13 91 1 1 14 92 1 1 15 93 1 6 16 94 1 0 18 95 1 1 20 96 1 0 20 97 1 0 21 98 1 1 22 99 1 1 23100 1 6 24101 1 0 25102 1 0 27103 1 1 29104 1 0 29105 1 0 30106 1 6 31107 1 1 32108 1 6 33109 1 0 34110 1 0 35111 1 0 36112 1 0 37113 1 0 37114 1 0 37115 1 0 39116 1 1 40117 1 6 42118 1 6 43119 1 1 44120 1 6 45121 1 0 46122 1 0 47123 1 0 47124 1 0 47125 1 0 52126 1 0 52127 1 0 53128 1 0 53129 1 0 55130 1 0 55131 1 0 56132 1 1 58133 1 0 59134 1 0 59135 1 0 60136 1 0 63137 1 0 63138 1 0 64139 1 1 65140 1 0 66141 1 0 66142 1 0 66143 1 0 67144 1 0 67145 1 0 67146 1 0 68147 1 0 68148 1 0 69149 1 0 69150 1 0 70151 1 6 72152 1 0 72153 1 0 72154 1 0 73155 1 0 73156 1 0 74157 1 0 74158 1 0 77159 1 1 78160 1 0 78161 1 0 78162 1 0 79163 1 0 79164 1 0 79165 1 0 80166 1 0 80167 1 0 80168 1 0 M END

Standard InCHIKey	JQDDJPUBPHMFHX-PJJISFTGSA-N
Standard InCHI	InChI=1S/C56H88O24/c1-22-25-11-14-54(7)32(53(25,6)13-12-28(22)57)10-9-26-27-17-52(4,5)15-16-56(27,33(60)18-55(26,54)8)51(70)80-50-45(37(64)34(61)23(2)74-50)79-49-41(68)38(65)43(24(3)75-49)77-48-42(69)44(30(59)20-72-48)78-47-40(67)36(63)31(21-73-47)76-46-39(66)35(62)29(58)19-71-46/h9,22-25,27,29-50,58-69H,10-21H2,1-8H3/t22-,23+,24-,25-,27-,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+/m0/s1
SMILES	O[C@H]1[C@@H](O[C@H]([C@@H]([C@H]1O)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)C)O[C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1O)O)C)OC(=O)[C@@]12CCC(C[C@H]2C2=CCC3[C@@]([C@@]2(C[C@H]1O)C)(C)CC[C@@H]1[C@]3(C)CCC(=O)[C@H]1C)(C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1144.57	Volume:	1094.623 ? Van der Waals volume.
Dense:	1.046	LogP:	1.233 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.836 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.123 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	58.0
TPSA:	369.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	24.0
H-Bond Donor:	12.0	Rings:	10.0
Heavy Atoms:	24.0

MedChem Properties

QED Drug-Likeness Score:	0.088	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.172	Fsp³:	0.929
MCE-18:	211.111 ? 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:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.224	Promiscuous compounds:	0.151

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.419	MDCK Permeability:	-5.078
Pgp-inhibitor:	0.0	Pgp-substrate:	0.941
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):	0.47
20% Bioavailability (F20%):	0.766	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.066
Plasma Protein Binding (PPB):	68.56%	Volume Distribution (VD):	-0.338
Fu:	20.985% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
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:	0.796
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.094
HLM stability:	0.622 ? 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):

-0.301

Half-life (T1/2):

3.204

ADMET: Toxicity

hERG Blockers:	0.004	hERG Blockers (10um):	0.008
Human Hepatotoxicity (H-HT):	0.853	Drug-induced Liver Injury (DILI):	0.963
AMES Toxicity:	0.973	Rat Oral Acute Toxicity:	0.005
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.066	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.999
Hematotoxicity:	0.777	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.813	RPMI-8226 Immunitoxicity:	0.548
A549 Cytotoxicity:	0.996	Hek293 Cytotoxicity:	0.889
BCF:	0.786 ? 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:	3.417 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.069 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.932 ? 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	=	65500.0	nM	PMID[26100440]

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 NPC471580 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	24098
0.1-0.2	22249
0.2-0.3	2771
0.3-0.4	508
0.4-0.5	166
0.5-0.6	43
0.6-0.7	12
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8261	Intermediate Similarity	NPC471577
0.812	Intermediate Similarity	NPC473386
0.75	Intermediate Similarity	NPC309223
0.7266	Intermediate Similarity	NPC102505
0.7266	Intermediate Similarity	NPC488514
0.7177	Intermediate Similarity	NPC13998
0.6614	Remote Similarity	NPC85154
0.6277	Remote Similarity	NPC8524
0.6232	Remote Similarity	NPC33012
0.6222	Remote Similarity	NPC224381
0.6194	Remote Similarity	NPC144644
0.6194	Remote Similarity	NPC170407
0.6187	Remote Similarity	NPC480421
0.6074	Remote Similarity	NPC37860
0.6061	Remote Similarity	NPC237191
0.6053	Remote Similarity	NPC472270
0.6053	Remote Similarity	NPC112492
0.6014	Remote Similarity	NPC68767
0.5954	Remote Similarity	NPC480423
0.5933	Remote Similarity	NPC485563
0.5912	Remote Similarity	NPC70809
0.5906	Remote Similarity	NPC104137
0.5906	Remote Similarity	NPC26626
0.5899	Remote Similarity	NPC293031
0.5896	Remote Similarity	NPC473452
0.5859	Remote Similarity	NPC815
0.5852	Remote Similarity	NPC470876
0.5839	Remote Similarity	NPC33068
0.5778	Remote Similarity	NPC286457
0.5735	Remote Similarity	NPC475514
0.5643	Remote Similarity	NPC220160
0.5606	Remote Similarity	NPC123522
0.5574	Remote Similarity	NPC480420
0.5548	Remote Similarity	NPC23020
0.5532	Remote Similarity	NPC142151
0.5524	Remote Similarity	NPC153673
0.5503	Remote Similarity	NPC297950
0.5467	Remote Similarity	NPC472268
0.5441	Remote Similarity	NPC488560
0.5423	Remote Similarity	NPC267694
0.5417	Remote Similarity	NPC110385
0.5417	Remote Similarity	NPC51099
0.5411	Remote Similarity	NPC275225
0.5354	Remote Similarity	NPC488526
0.5301	Remote Similarity	NPC488513
0.5274	Remote Similarity	NPC480422
0.5227	Remote Similarity	NPC69811
0.52	Remote Similarity	NPC489208
0.5194	Remote Similarity	NPC105800
0.5182	Remote Similarity	NPC257211
0.5116	Remote Similarity	NPC164389
0.5116	Remote Similarity	NPC305267
0.5105	Remote Similarity	NPC202828
0.5105	Remote Similarity	NPC119592
0.5074	Remote Similarity	NPC300419
0.5072	Remote Similarity	NPC480419
0.5065	Remote Similarity	NPC329893
0.5036	Remote Similarity	NPC475160
0.5036	Remote Similarity	NPC473714
0.5034	Remote Similarity	NPC478825
0.5031	Remote Similarity	NPC472269

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471580 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7713
0.1-0.2	1405
0.2-0.3	32
0.3-0.4	0
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