NPASS Compound

Natural Product: NPC500919

Natural Product ID	NPC500919
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(25R)-3beta-{O-alpha-L-Rhamnopyranosyl-(1â†’2)-[O-beta-D-glucopyranosyl-(1â†’4)-O-alpha-L-rhamnopyranosyl-(1â†’4)]-beta-D-glucopyranosyl}-22alpha-N-spirosol-5-ene
IUPAC Name	(3~{S},4~{S},5~{S},6~{R})-2-[(3~{R},4~{S},5~{S},6~{R})-5-[(3~{S},4~{R},5~{S},6~{R})-3,4-dihydroxy-6-methyl-5-[(3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-2-(5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-18-ene-6,2'-piperidine]-16-yl)oxy-tetrahydropyran-3-yl]oxy-6-methyl-tetrahydropyran-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 155164 0 0 0 0 0 0 0 0999 V2000 13.5420 -3.2347 1.5305 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7431 -1.9433 1.7600 C 0 0 0 0 0 0 0 0 0 0 0 0 13.4224 -0.8711 0.9792 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5137 0.3444 0.7446 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1042 -0.0638 0.4995 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0310 -1.4714 0.1584 N 0 0 0 0 0 0 0 0 0 0 0 0 11.3291 -2.2222 1.3626 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2700 0.1242 1.6168 O 0 0 0 0 0 0 0 0 0 0 0 0 9.3524 1.0634 1.2945 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9556 0.9437 1.7988 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2814 1.7892 0.7013 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8112 1.7412 0.7226 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3325 2.1858 2.0872 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8606 2.1947 2.0581 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1363 1.4802 1.2259 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6650 1.6208 1.3456 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9402 0.5509 0.6018 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3712 0.3862 1.0684 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3088 0.5919 0.0758 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0057 1.7673 0.4853 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8971 2.1400 -0.5287 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4767 3.4736 -0.1690 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3477 3.9800 -1.1008 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9673 1.0853 -0.5483 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0912 1.3783 -1.2673 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2639 1.1840 -0.5016 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0423 0.2893 -1.1974 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2270 -0.0720 -0.6139 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8578 -1.1345 -1.5262 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1393 1.1279 -0.5141 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.3598 0.8782 0.0523 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.4368 1.2287 -0.7687 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1613 2.2276 -0.1615 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.1517 1.8075 0.7004 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.5316 1.0476 1.8384 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6281 1.8451 2.5547 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.1925 0.9164 0.0382 C 0 0 1 0 0 0 0 0 0 0 0 0 -15.3918 1.6048 -0.1288 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.6996 0.4981 -1.3192 C 0 0 2 0 0 0 0 0 0 0 0 0 -14.4604 -0.5427 -1.8286 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2453 0.0675 -1.2428 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.8692 -0.3044 -2.5582 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3986 2.1587 0.3334 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.1197 3.3384 0.4794 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0389 2.4612 -0.3092 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3124 3.0997 -1.5153 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2547 -0.1639 -1.1351 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1295 -1.1723 -1.4235 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2534 -0.5564 -0.0138 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6374 -1.6879 -0.4620 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8980 -2.8039 0.3332 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7429 -3.6143 -0.4754 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9325 -4.3162 -1.3616 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7301 -4.7379 -2.5836 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4366 -5.5420 -0.5997 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.2141 -5.9883 -1.1263 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2004 -5.0758 0.8218 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4070 -5.0818 1.4842 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7186 -3.6195 0.7035 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1621 -3.3243 1.9385 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6529 -0.7572 0.7252 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0766 -0.7635 0.3064 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7405 0.5905 0.2186 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5097 1.1036 -1.1940 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2252 0.3949 0.4802 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9723 -0.3396 -0.5453 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0087 0.3574 -1.3312 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9138 1.3106 -0.5918 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0710 2.5377 -1.4536 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0927 0.6235 -0.1664 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4526 0.7599 -0.6410 C 0 0 0 0 0 0 0 0 0 0 0 0 11.1185 2.0869 -0.5805 C 0 0 0 0 0 0 0 0 0 0 0 0 13.0760 -4.0565 2.0753 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5884 -3.3673 0.4306 H 0 0 0 0 0 0 0 0 0 0 0 0 14.6066 -3.0535 1.8419 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8405 -1.7342 2.8600 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3268 -0.4965 1.4906 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7184 -1.2213 -0.0422 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5510 0.9265 1.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9956 0.9101 -0.0625 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7499 -1.7018 -0.5687 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1460 -3.2987 1.1508 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6632 -1.8486 2.1766 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6897 2.1063 1.3298 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5924 -0.0816 1.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7753 1.4283 2.7611 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6027 2.8315 0.9322 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4306 2.4440 -0.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6423 1.3667 2.7997 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7680 3.1622 2.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3771 2.8596 2.7993 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3707 1.5888 2.4370 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3313 2.6541 1.0262 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8226 0.7918 -0.4911 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8677 0.7823 -0.9318 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3794 2.2320 -1.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9965 3.4416 0.8127 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6457 4.2086 -0.0351 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3474 4.9569 -1.1675 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2659 0.8361 0.4983 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9692 0.8165 0.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1152 -0.5168 0.3978 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0020 -0.7063 -2.5538 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1694 -1.9935 -1.6508 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7925 -1.5082 -1.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2506 1.5418 -1.5501 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9462 1.6582 -1.6960 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6652 2.7052 1.1299 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.3109 0.7118 2.5756 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9873 0.1422 1.5396 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6516 1.6075 3.5181 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.3425 -0.0092 0.6428 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.4333 1.9563 -1.0550 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8193 1.3645 -2.0039 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9171 -1.3476 -2.0607 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1984 -0.8363 -0.6193 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0817 0.4451 -3.1847 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1751 1.7417 1.3345 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7449 3.5352 -0.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5103 3.1347 0.4095 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3665 4.0753 -1.3500 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6432 0.2078 -1.9759 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0710 -1.4287 -2.3689 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8342 -0.7079 0.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5325 -2.5574 1.2073 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0681 -3.7662 -1.7290 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4578 -5.5141 -2.2794 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0026 -5.0799 -3.3338 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2567 -3.8423 -2.9545 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1860 -6.3516 -0.5813 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4292 -6.1600 -0.3853 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4087 -5.6802 1.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4423 -4.4466 2.2444 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0800 -3.6416 -0.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7995 -3.5615 1.9301 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0928 -1.4829 0.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4912 -1.1563 1.7536 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6314 -1.3761 1.0752 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1880 -1.3394 -0.6386 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4094 1.5612 -1.6251 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0210 0.3416 -1.8293 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7750 1.9589 -1.1306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2861 -0.1453 1.4768 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2608 -0.7739 -1.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3955 -1.2896 -0.0895 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6582 -0.4526 -1.7852 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5808 0.8639 -2.2201 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2039 3.4723 -0.8589 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7538 2.4221 -2.2991 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0527 2.6974 -1.9282 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8765 -0.4837 -0.0465 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7204 0.1973 -1.5593 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9443 2.0785 -1.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5959 2.3029 0.4222 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5294 2.9661 -0.8008 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 5 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 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 34 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 30 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 24 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 53 55 1 0 55 56 1 0 55 57 1 0 57 58 1 0 57 59 1 0 59 60 1 0 17 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 63 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 68 69 1 0 68 70 1 0 70 71 1 0 71 72 1 0 7 2 1 0 70 9 1 0 71 5 1 0 68 11 1 0 65 12 1 0 63 15 1 0 49 19 1 0 59 51 1 0 45 26 1 0 41 32 1 0 1 73 1 0 1 74 1 0 1 75 1 0 2 76 1 0 3 77 1 0 3 78 1 0 4 79 1 0 4 80 1 0 6 81 1 0 7 82 1 0 7 83 1 0 9 84 1 0 10 85 1 0 10 86 1 0 11 87 1 0 12 88 1 0 13 89 1 0 13 90 1 0 14 91 1 0 16 92 1 0 16 93 1 0 17 94 1 0 19 95 1 0 21 96 1 6 22 97 1 0 22 98 1 0 23 99 1 0 24100 1 1 26101 1 0 28102 1 1 29103 1 0 29104 1 0 29105 1 0 30106 1 6 32107 1 0 34108 1 1 35109 1 0 35110 1 0 36111 1 0 37112 1 1 38113 1 0 39114 1 6 40115 1 0 41116 1 1 42117 1 0 43118 1 1 44119 1 0 45120 1 1 46121 1 0 47122 1 6 48123 1 0 49124 1 1 51125 1 0 53126 1 6 54127 1 0 54128 1 0 54129 1 0 55130 1 1 56131 1 0 57132 1 1 58133 1 0 59134 1 6 60135 1 0 61136 1 0 61137 1 0 62138 1 0 62139 1 0 64140 1 0 64141 1 0 64142 1 0 65143 1 0 66144 1 0 66145 1 0 67146 1 0 67147 1 0 69148 1 0 69149 1 0 69150 1 0 70151 1 0 71152 1 0 72153 1 0 72154 1 0 72155 1 0 M END

Standard InCHIKey	MJTVVRUDYJNHJC-SZAVSVHQSA-N
Standard InCHI	InChI=1S/C51H83NO20/c1-20-9-14-51(52-17-20)21(2)32-29(72-51)16-28-26-8-7-24-15-25(10-12-49(24,5)27(26)11-13-50(28,32)6)66-48-44(71-45-38(60)35(57)33(55)22(3)64-45)41(63)43(31(19-54)68-48)70-46-40(62)37(59)42(23(4)65-46)69-47-39(61)36(58)34(56)30(18-53)67-47/h7,20-23,25-48,52-63H,8-19H2,1-6H3/t20?,21?,22-,23-,25?,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?,51?/m1/s1
SMILES	CC1CCC2(NC1)OC1CC3C4CC=C5CC(OC6O[C@H](CO)[C@@H](OC7O[C@H](C)[C@@H](OC8O[C@H](CO)[C@@H](O)[C@H](O)[C@H]8O)[C@H](O)[C@@H]7O)[C@H](O)[C@H]6OC6O[C@H](C)[C@@H](O)[C@H](O)[C@@H]6O)CCC5(C)C4CCC3(C)C1C2C

Calculated Properties

Physi-Chem Properties

MedChem Properties

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

ADMET: Distribution

ADMET: Metabolism

ADMET: Excretion

ADMET: Toxicity

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO24724	Solanum aculeastrum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24724	Solanum aculeastrum	Species	Solanaceae	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

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

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 NPC500919 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	25885
0.1-0.2	20862
0.2-0.3	2408
0.3-0.4	575
0.4-0.5	59
0.5-0.6	38
0.6-0.7	23
0.7-0.8	1
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9072	High Similarity	NPC122819
0.8148	Intermediate Similarity	NPC287885
0.8081	Intermediate Similarity	NPC15249
0.8081	Intermediate Similarity	NPC25455
0.781	Intermediate Similarity	NPC150057
0.781	Intermediate Similarity	NPC147753
0.7168	Intermediate Similarity	NPC23808
0.7168	Intermediate Similarity	NPC87998
0.6887	Remote Similarity	NPC94272
0.6814	Remote Similarity	NPC269297
0.6814	Remote Similarity	NPC222202
0.6752	Remote Similarity	NPC308140
0.6667	Remote Similarity	NPC247037
0.6637	Remote Similarity	NPC73243
0.6637	Remote Similarity	NPC244086
0.6637	Remote Similarity	NPC84956
0.6549	Remote Similarity	NPC480555
0.6549	Remote Similarity	NPC150372
0.6356	Remote Similarity	NPC249265
0.6341	Remote Similarity	NPC224314
0.6283	Remote Similarity	NPC470433
0.6283	Remote Similarity	NPC46190
0.6283	Remote Similarity	NPC171073
0.6271	Remote Similarity	NPC194207
0.6271	Remote Similarity	NPC22779
0.6261	Remote Similarity	NPC475182
0.625	Remote Similarity	NPC480553
0.6228	Remote Similarity	NPC248746
0.6174	Remote Similarity	NPC42171
0.6083	Remote Similarity	NPC480554
0.6016	Remote Similarity	NPC232054
0.5943	Remote Similarity	NPC165439
0.5917	Remote Similarity	NPC475333
0.5917	Remote Similarity	NPC32361
0.5917	Remote Similarity	NPC224098
0.5917	Remote Similarity	NPC208383
0.5763	Remote Similarity	NPC6806
0.5748	Remote Similarity	NPC480556
0.5738	Remote Similarity	NPC254255
0.5702	Remote Similarity	NPC486386
0.5641	Remote Similarity	NPC98696
0.5593	Remote Similarity	NPC265275
0.5565	Remote Similarity	NPC470432
0.5565	Remote Similarity	NPC230507
0.5546	Remote Similarity	NPC477809
0.5537	Remote Similarity	NPC102016
0.5537	Remote Similarity	NPC95051
0.547	Remote Similarity	NPC305423
0.547	Remote Similarity	NPC113044
0.547	Remote Similarity	NPC283829
0.547	Remote Similarity	NPC161676
0.5437	Remote Similarity	NPC485606
0.5413	Remote Similarity	NPC486114
0.5403	Remote Similarity	NPC13193
0.5372	Remote Similarity	NPC300557
0.5323	Remote Similarity	NPC475550
0.5317	Remote Similarity	NPC218571
0.5317	Remote Similarity	NPC487615
0.5246	Remote Similarity	NPC124677
0.5243	Remote Similarity	NPC147835
0.5243	Remote Similarity	NPC253645
0.5243	Remote Similarity	NPC85001
0.5243	Remote Similarity	NPC95920
0.5207	Remote Similarity	NPC602423
0.5188	Remote Similarity	NPC477808
0.5159	Remote Similarity	NPC309278
0.5116	Remote Similarity	NPC477811
0.5083	Remote Similarity	NPC470748
0.5042	Remote Similarity	NPC6295

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC500919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7811
0.1-0.2	1284
0.2-0.3	49
0.3-0.4	3
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9072	High Similarity	NPD8449	Approved
0.781	Intermediate Similarity	NPD8450	Suspended

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