NPASS Compound

Natural Product: NPC471383

Natural Product ID	NPC471383
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3Beta-O-{Alpha-L-Rhamnopyranosyl-(1->2)-[Beta-D-Glucopyranosyl-(1->4)]-Alpha-L-Arabinopyranosyl}Hederagenin
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-5-[(2S,3R,4S,5S,6R)-6-ethyl-3,4,5-trihydroxyoxan-2-yl]oxy-4-hydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2430031
PubChem CID	73352338
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 142149 0 0 0 0 0 0 0 0999 V2000 -10.3151 3.9994 -1.8786 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1203 3.1909 -1.4240 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8745 4.0259 -1.4434 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9734 5.2315 -0.5350 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9495 4.7843 0.8878 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6761 3.9922 1.1244 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6419 2.8496 0.1437 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7550 3.2889 -1.1594 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4214 2.1439 0.2004 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5680 0.8307 0.5743 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8347 0.5438 1.8371 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4748 0.4563 1.7479 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9767 -0.1689 0.6159 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0203 -1.0754 0.0651 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1115 -0.1369 -0.4962 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1337 -0.8355 -1.0863 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5693 -1.9714 0.9559 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6124 -3.2821 0.5220 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8367 -4.1679 1.4324 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5906 -5.4242 1.7238 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0772 -5.9863 0.3985 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9544 -4.9624 -0.3064 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9180 -3.7459 0.3818 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4333 -4.7380 -1.7004 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0457 -6.4133 -0.4157 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6621 -5.1744 2.5479 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6061 -3.4582 2.6340 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7736 -0.7264 0.9408 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.6887 -0.1571 0.2821 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2057 0.5192 1.2919 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3780 1.2104 0.6914 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9212 0.4974 -0.5665 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5462 -0.9538 -0.3699 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0859 -1.2394 -0.3913 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5096 -1.5034 -1.7364 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1360 -2.5249 0.4272 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2917 -2.4130 1.7242 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3915 -1.9337 -1.1124 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8688 -1.6715 -0.8456 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2167 -0.2838 -1.3383 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4102 0.6054 -0.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9240 2.0165 -0.3779 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2616 1.8907 0.2696 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0789 0.9514 -0.1752 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6590 0.0714 -1.2853 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5943 -1.1137 -1.3755 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0619 -1.6662 -0.0851 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6210 -0.6581 0.8736 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4121 0.7628 0.4704 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5615 1.3712 -0.2534 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6946 1.5806 0.7753 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6994 0.4167 1.7065 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1075 -0.8212 1.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0238 1.6291 0.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5168 2.9044 1.4866 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9439 -0.8963 2.1878 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0888 -1.8153 2.3387 O 0 0 0 0 0 0 0 0 0 0 0 0 7.2000 -0.1364 3.3244 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0554 0.8771 -2.5522 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8182 -0.2047 -2.8011 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3185 1.1989 -1.7167 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7644 3.5273 2.4377 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9345 5.8863 1.7588 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0617 6.0066 -0.8658 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0614 4.7716 -2.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8156 4.3953 -0.9844 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0266 3.2958 -2.3592 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3593 2.7517 -0.4535 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9718 2.3842 -2.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7562 4.4275 -2.4752 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0552 5.8467 -0.7092 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7963 4.1056 1.1275 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7816 4.6453 1.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4254 2.1250 0.4299 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6640 0.6621 0.7626 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0378 1.4163 2.5315 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3035 -0.3159 2.4047 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8048 0.6376 -0.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7057 -1.6567 -0.8332 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5967 0.4611 -1.2868 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0174 -0.4111 -0.9975 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1688 -3.3661 -0.5077 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8378 -4.4309 0.9963 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9005 -6.1800 2.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7170 -6.8576 0.6294 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0014 -5.3117 -0.3806 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9413 -5.4192 -2.4312 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5538 -3.6736 -2.0240 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3627 -4.9897 -1.7259 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8300 -7.3560 -0.1384 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4077 -5.7981 2.3469 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5206 -3.3252 3.0327 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0962 0.6257 -0.3849 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4348 1.3107 1.7918 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5126 -0.1451 2.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1188 2.2499 0.4617 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.2540 1.4927 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8509 -1.1311 0.7178 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1869 -1.6963 -2.5439 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1924 -2.4071 -1.7157 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2088 -0.6804 -2.0331 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3169 -3.4073 -0.0659 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2401 -2.7572 0.4446 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2773 -2.8932 2.3778 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2156 -2.9287 -0.5892 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1383 -2.1270 -2.1415 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9521 -1.6342 0.2721 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3938 -2.4937 -1.2984 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6117 0.2119 0.5968 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2861 2.5307 0.4027 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8606 2.6269 -1.2519 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6040 2.5204 1.0804 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1827 -1.9270 -1.9992 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5339 -0.8419 -1.9451 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3115 -2.3393 0.3850 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9227 -2.3620 -0.3278 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3626 1.3366 1.4504 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2742 2.3157 -0.7122 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0455 0.7352 -1.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7755 0.2034 1.9767 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2388 0.7311 2.6655 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6671 -1.0572 0.1871 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2388 -1.6379 1.8687 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7271 0.8724 0.4286 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9093 1.4671 -1.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5251 2.6147 0.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4758 3.0092 1.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2509 2.9419 2.2969 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8002 3.6970 0.7401 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5863 -0.1751 4.1282 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6213 1.8589 -2.5943 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0109 0.2536 -3.4575 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1644 1.0503 -2.4092 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4293 -1.0073 -3.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7897 -0.4433 -3.0244 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0633 0.7450 -3.2701 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7467 0.6212 -2.4349 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1041 1.7447 -2.3241 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6294 2.0538 -1.4298 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1875 2.6117 2.4141 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1258 5.5771 2.6846 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3464 6.4861 -0.0322 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 7 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 22 24 1 0 21 25 1 0 20 26 1 0 19 27 1 0 13 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 33 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 2 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 51 54 1 0 51 55 1 0 48 56 1 0 56 57 2 0 56 58 1 0 45 59 1 0 40 60 1 0 32 61 1 0 6 62 1 0 5 63 1 0 4 64 1 0 8 3 1 0 15 10 1 0 23 18 1 0 34 29 1 0 41 32 1 0 45 40 1 0 49 44 1 0 53 48 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 0 2 69 1 0 3 70 1 0 4 71 1 0 5 72 1 0 6 73 1 0 7 74 1 0 10 75 1 0 11 76 1 0 11 77 1 0 13 78 1 0 14 79 1 0 15 80 1 0 16 81 1 0 18 82 1 0 19 83 1 0 20 84 1 0 21 85 1 0 22 86 1 0 24 87 1 0 24 88 1 0 24 89 1 0 25 90 1 0 26 91 1 0 27 92 1 0 29 93 1 0 30 94 1 0 30 95 1 0 31 96 1 0 31 97 1 0 33 98 1 0 35 99 1 0 35100 1 0 35101 1 0 36102 1 0 36103 1 0 37104 1 0 38105 1 0 38106 1 0 39107 1 0 39108 1 0 41109 1 0 42110 1 0 42111 1 0 43112 1 0 46113 1 0 46114 1 0 47115 1 0 47116 1 0 49117 1 0 50118 1 0 50119 1 0 52120 1 0 52121 1 0 53122 1 0 53123 1 0 54124 1 0 54125 1 0 54126 1 0 55127 1 0 55128 1 0 55129 1 0 58130 1 0 59131 1 0 59132 1 0 59133 1 0 60134 1 0 60135 1 0 60136 1 0 61137 1 0 61138 1 0 61139 1 0 62140 1 0 63141 1 0 64142 1 0 M END

Standard InCHIKey	YVZJSSFXXNLBHY-LNBDOPGKSA-N
Standard InCHI	InChI=1S/C48H78O16/c1-9-26-32(51)35(54)37(56)40(61-26)62-27-21-59-41(38(33(27)52)64-39-36(55)34(53)31(50)23(2)60-39)63-30-13-14-44(5)28(45(30,6)22-49)12-15-47(8)29(44)11-10-24-25-20-43(3,4)16-18-48(25,42(57)58)19-17-46(24,47)7/h10,23,25-41,49-56H,9,11-22H2,1-8H3,(H,57,58)/t23-,25-,26+,27-,28+,29+,30-,31-,32+,33-,34+,35-,36+,37+,38+,39-,40-,41-,44-,45-,46+,47+,48-/m0/s1
SMILES	CCC1C(C(C(C(O1)OC2COC(C(C2O)OC3C(C(C(C(O3)C)O)O)O)OC4CCC5(C(C4(C)CO)CCC6(C5CC=C7C6(CCC8(C7CC(CC8)(C)C)C(=O)O)C)C)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	910.53	Volume:	905.683 ? Van der Waals volume.
Dense:	1.005	LogP:	2.13 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.963 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.255 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	45.0
TPSA:	254.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	8.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.119	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.299	Fsp³:	0.938
MCE-18:	170.667 ? 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:	0.386	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.003 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.305 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.193	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.447	MDCK Permeability:	-4.996
Pgp-inhibitor:	0.0	Pgp-substrate:	0.951
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):	0.797
20% Bioavailability (F20%):	0.017	30% Bioavailability (F30%):	0.336
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	57.721%	Volume Distribution (VD):	-0.466
Fu:	26.811% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.012	BCRP inhibitor:	0.0
BSEP inhibitor:	0.144

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.923	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

-0.063

Half-life (T1/2):

3.719

ADMET: Toxicity

hERG Blockers:	0.013	hERG Blockers (10um):	0.139
Human Hepatotoxicity (H-HT):	0.318	Drug-induced Liver Injury (DILI):	0.133
AMES Toxicity:	0.092	Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.289	Skin Sensitization:	0.012
Carcinogencity:	0.012	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.193	Ototoxicity:	1.0
Hematotoxicity:	0.02	Drug-induced Nephrotoxicity:	0.023
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.016	Hek293 Cytotoxicity:	0.434
BCF:	0.929 ? 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:	4.249 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.26 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.58 ? 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
NPO32682	anemone taipaiensis	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[23992864]
NPO32682	anemone taipaiensis	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	5

Activity Type	# Activity
Cell line	4
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
NPT165	Cell line	HeLa	Homo sapiens	IC50	=	9360.0	nM	PMID[8021914]
NPT81	Cell line	A549	Homo sapiens	IC50	=	11670.0	nM	PMID[24063582]
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	6130.0	nM	DrugMatrix in vivo data: Pathology
NPT65	Cell line	HepG2	Homo sapiens	IC50	=	12230.0	nM	PMID[7119809]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	5870.0	nM	PMID[23992864]

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 NPC471383 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	22285
0.1-0.2	23340
0.2-0.3	2916
0.3-0.4	866
0.4-0.5	331
0.5-0.6	66
0.6-0.7	32
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.914	High Similarity	NPC139044
0.8454	Intermediate Similarity	NPC257468
0.82	Intermediate Similarity	NPC323359
0.8191	Intermediate Similarity	NPC174679
0.8191	Intermediate Similarity	NPC279554
0.783	Intermediate Similarity	NPC323341
0.7708	Intermediate Similarity	NPC12288
0.7449	Intermediate Similarity	NPC56713
0.7449	Intermediate Similarity	NPC59804
0.7429	Intermediate Similarity	NPC488564
0.7281	Intermediate Similarity	NPC471385
0.7273	Intermediate Similarity	NPC166422
0.7238	Intermediate Similarity	NPC276093
0.7172	Intermediate Similarity	NPC136877
0.7143	Intermediate Similarity	NPC54636
0.71	Intermediate Similarity	NPC25605
0.6915	Remote Similarity	NPC204407
0.6863	Remote Similarity	NPC127056
0.6726	Remote Similarity	NPC133818
0.6698	Remote Similarity	NPC104400
0.6698	Remote Similarity	NPC10320
0.6697	Remote Similarity	NPC324875
0.6697	Remote Similarity	NPC292677
0.6667	Remote Similarity	NPC284807
0.6667	Remote Similarity	NPC219180
0.6667	Remote Similarity	NPC28198
0.6667	Remote Similarity	NPC476123
0.6634	Remote Similarity	NPC270667
0.6634	Remote Similarity	NPC164194
0.6555	Remote Similarity	NPC161717
0.6449	Remote Similarity	NPC114304
0.6422	Remote Similarity	NPC481082
0.6422	Remote Similarity	NPC164419
0.6339	Remote Similarity	NPC488209
0.6327	Remote Similarity	NPC606107
0.6321	Remote Similarity	NPC472949
0.6321	Remote Similarity	NPC488561
0.6316	Remote Similarity	NPC476992
0.6239	Remote Similarity	NPC251263
0.6176	Remote Similarity	NPC473538
0.6154	Remote Similarity	NPC471384
0.608	Remote Similarity	NPC488212
0.6075	Remote Similarity	NPC114441
0.6075	Remote Similarity	NPC109079
0.6071	Remote Similarity	NPC119794
0.6055	Remote Similarity	NPC469945
0.6055	Remote Similarity	NPC240734
0.6	Remote Similarity	NPC283849
0.5948	Remote Similarity	NPC280941
0.5948	Remote Similarity	NPC235772
0.5932	Remote Similarity	NPC151543
0.5929	Remote Similarity	NPC79718
0.5841	Remote Similarity	NPC73829
0.5825	Remote Similarity	NPC100383
0.5818	Remote Similarity	NPC80843
0.5818	Remote Similarity	NPC22956
0.5804	Remote Similarity	NPC180550
0.5804	Remote Similarity	NPC35405
0.5726	Remote Similarity	NPC475486
0.5714	Remote Similarity	NPC309714
0.5678	Remote Similarity	NPC62725
0.5664	Remote Similarity	NPC473383
0.5652	Remote Similarity	NPC488515
0.5577	Remote Similarity	NPC286347
0.5575	Remote Similarity	NPC204392
0.5556	Remote Similarity	NPC218954
0.5534	Remote Similarity	NPC57362
0.5512	Remote Similarity	NPC65105
0.5508	Remote Similarity	NPC187618
0.55	Remote Similarity	NPC288205
0.55	Remote Similarity	NPC51465
0.5446	Remote Similarity	NPC488516
0.544	Remote Similarity	NPC488211
0.5431	Remote Similarity	NPC123796
0.5421	Remote Similarity	NPC294112
0.5391	Remote Similarity	NPC293330
0.5385	Remote Similarity	NPC484832
0.537	Remote Similarity	NPC191410
0.5357	Remote Similarity	NPC480424
0.5339	Remote Similarity	NPC37134
0.5333	Remote Similarity	NPC177246
0.5328	Remote Similarity	NPC76972
0.5328	Remote Similarity	NPC313110
0.5328	Remote Similarity	NPC469782
0.5328	Remote Similarity	NPC204414
0.5321	Remote Similarity	NPC475611
0.531	Remote Similarity	NPC6377
0.531	Remote Similarity	NPC208381
0.5299	Remote Similarity	NPC131469
0.5283	Remote Similarity	NPC31839
0.528	Remote Similarity	NPC475140
0.5273	Remote Similarity	NPC127853
0.5268	Remote Similarity	NPC475296
0.5254	Remote Similarity	NPC95437
0.5254	Remote Similarity	NPC486563
0.525	Remote Similarity	NPC120116
0.521	Remote Similarity	NPC114692
0.521	Remote Similarity	NPC236657
0.5203	Remote Similarity	NPC473824
0.5169	Remote Similarity	NPC475504
0.5158	Remote Similarity	NPC480946
0.5158	Remote Similarity	NPC130577
0.5158	Remote Similarity	NPC142415
0.5158	Remote Similarity	NPC102683
0.5155	Remote Similarity	NPC120840
0.5133	Remote Similarity	NPC474589
0.5104	Remote Similarity	NPC270768
0.5104	Remote Similarity	NPC59263
0.5104	Remote Similarity	NPC210106
0.5088	Remote Similarity	NPC482748
0.5085	Remote Similarity	NPC162574
0.5083	Remote Similarity	NPC78034
0.5045	Remote Similarity	NPC475472
0.5038	Remote Similarity	NPC43550

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471383 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6688
0.1-0.2	2411
0.2-0.3	46
0.3-0.4	5
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