NPASS Compound

Natural Product: NPC158051

Natural Product ID	NPC158051
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cyclaminorin
IUPAC Name	n.a.
Synonyms	Cyclaminorin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL507039
PubChem CID	44566606
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 141149 0 0 0 0 0 0 0 0999 V2000 -1.5561 1.7567 -1.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8000 0.5842 -0.4608 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1962 0.7954 1.0007 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6617 0.7278 -0.5307 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1395 2.1269 -0.2621 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5493 1.9631 0.3138 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4982 1.3234 -0.7057 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7522 2.3675 -1.7290 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8680 0.0562 -1.1713 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7906 -0.6768 -2.0694 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8375 -1.2780 -1.1116 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6027 -0.0728 -0.6164 C 0 0 1 0 0 0 0 0 0 0 0 0 6.8052 -0.5612 0.0333 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7894 -1.4053 1.2181 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9914 -1.3086 2.1246 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4834 -1.2710 3.5503 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9601 -0.2263 1.8220 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9829 0.2646 0.4029 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6452 0.6764 0.0015 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4704 0.8746 -1.5267 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1688 0.4850 -1.8044 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1011 1.9500 0.5011 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7274 2.2493 -0.0853 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8109 1.0102 -0.0058 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5186 0.9053 1.4706 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2249 2.2469 1.8286 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8010 -2.5913 2.0725 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4696 -3.5015 1.3427 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4381 0.1529 -1.6619 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3589 0.7575 -2.9968 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9258 -1.2701 -1.8027 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5614 -1.2952 -2.0986 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3379 -0.7333 -0.8970 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6716 -0.8271 -1.1308 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3607 -1.8470 -0.5827 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.6412 -1.4926 0.1620 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8086 -1.3774 -0.8030 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4072 -0.9426 -2.1697 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1601 -1.6429 -2.6693 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8383 -2.6055 -1.6947 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3161 0.4422 -2.2036 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1707 1.0530 -3.0829 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2356 1.9119 -2.4199 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6451 2.9837 -1.5622 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3212 3.3816 -2.1792 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2964 3.1186 -3.6645 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.9305 3.5659 -4.1686 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8256 3.3996 -5.5512 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4353 1.7770 -3.9913 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1889 4.7552 -1.9886 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3850 2.5991 -0.2518 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8951 2.5526 -3.4928 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7400 -0.4833 -0.2847 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8644 -2.5343 1.0209 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9866 -2.2730 2.3623 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2915 -2.8911 2.8035 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5261 -2.9046 4.2741 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3077 -3.5825 4.9011 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1124 -2.8076 4.3718 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.8999 -3.2180 5.1741 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1757 -2.9953 6.5212 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9544 -2.9991 3.0110 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3967 -3.3966 6.2574 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6603 -3.7058 4.5035 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3787 -2.3690 2.1072 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2560 1.9374 -2.1421 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2865 2.6602 -0.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6174 1.5555 -0.9303 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1847 1.8669 1.2751 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2498 0.4426 1.1716 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4870 0.1986 1.6082 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0437 0.1230 0.3612 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1112 2.7804 -1.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5599 2.6279 0.5391 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3590 1.2466 1.1517 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8631 2.9620 0.6110 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1044 3.2927 -1.1768 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8310 2.7826 -2.2214 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4086 2.0765 -2.5507 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7501 -0.5585 -0.2194 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3694 -0.0531 -2.7798 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3918 -1.5255 -2.6201 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5380 -1.9422 -1.6149 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3649 -1.7485 -0.2522 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2997 -1.2190 -0.7753 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7482 -2.5162 0.9372 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8186 -1.3976 1.8092 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2039 -0.7645 4.2341 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5322 -0.6942 3.5393 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2736 -2.2849 3.9365 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7627 0.6354 2.4853 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0234 -0.5230 2.0502 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3257 -0.5599 -0.2853 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7053 1.0974 0.3314 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7424 1.8845 -1.8195 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1557 0.1107 -1.9905 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7540 2.7504 0.0072 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8947 2.3772 -1.1735 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2855 3.1231 0.4240 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1256 1.9234 1.7757 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4411 0.8769 2.1096 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8651 0.0815 1.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4078 3.2009 2.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6804 -2.7120 2.6804 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4086 0.8008 -3.4192 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9165 1.7299 -3.1269 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8630 0.1109 -3.7911 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0391 -1.7245 -0.7765 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4042 -1.8556 -2.5835 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8133 -2.3541 -2.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7897 -0.7753 -3.0368 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1076 -1.5111 -0.1366 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7551 -2.5727 -0.0029 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5624 -0.5525 0.7215 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2967 -2.3724 -0.8204 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2077 -1.2254 -2.8834 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3423 -0.9385 -2.8776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3267 -2.1952 -3.6148 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7290 0.2628 -3.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9779 1.2740 -1.9518 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3587 3.8309 -1.5013 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4647 2.9016 -1.6742 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0316 3.7827 -4.1769 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0992 3.0043 -3.7005 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7432 4.6453 -3.9569 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9682 3.8523 -5.8022 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9688 4.9227 -1.0127 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2745 2.4449 0.1762 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8761 2.4821 -3.3963 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4712 -0.1898 0.6127 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9320 -1.2454 2.6885 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2233 -3.9716 2.4865 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6974 -1.8944 4.6446 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2877 -4.6233 4.5786 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3685 -1.7163 4.5212 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0371 -2.6201 4.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7215 -4.2892 4.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8078 -3.7466 7.0438 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2101 -4.2497 6.7034 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7130 -4.4105 3.8136 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2212 -2.8533 2.3302 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 6 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 1 15 17 1 0 17 18 1 0 19 18 1 6 19 20 1 0 20 21 1 0 19 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 22 26 1 0 15 27 1 0 27 28 2 0 9 29 1 0 29 30 1 6 29 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 45 50 1 0 44 51 1 0 43 52 1 0 37 53 1 0 36 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 0 60 61 1 0 59 62 1 0 58 63 1 0 57 64 1 0 56 65 1 0 33 2 1 0 40 35 1 0 49 42 1 0 62 55 1 0 29 4 1 0 24 7 1 0 24 12 1 0 12 21 1 6 19 13 1 0 1 66 1 0 1 67 1 0 1 68 1 0 3 69 1 0 3 70 1 0 3 71 1 0 4 72 1 1 5 73 1 0 5 74 1 0 6 75 1 0 6 76 1 0 8 77 1 0 8 78 1 0 8 79 1 0 9 80 1 1 10 81 1 0 10 82 1 0 11 83 1 0 11 84 1 0 13 85 1 6 14 86 1 0 14 87 1 0 16 88 1 0 16 89 1 0 16 90 1 0 17 91 1 0 17 92 1 0 18 93 1 0 18 94 1 0 20 95 1 0 20 96 1 0 22 97 1 6 23 98 1 0 23 99 1 0 25100 1 0 25101 1 0 25102 1 0 26103 1 0 27104 1 0 30105 1 0 30106 1 0 30107 1 0 31108 1 0 31109 1 0 32110 1 0 32111 1 0 33112 1 1 35113 1 1 36114 1 1 37115 1 6 38116 1 6 39117 1 0 39118 1 0 42119 1 6 43120 1 1 44121 1 1 45122 1 1 46123 1 6 47124 1 0 47125 1 0 48126 1 0 50127 1 0 51128 1 0 52129 1 0 53130 1 0 55131 1 6 56132 1 6 57133 1 1 58134 1 1 59135 1 6 60136 1 0 60137 1 0 61138 1 0 63139 1 0 64140 1 0 65141 1 0 M END

Standard InCHIKey	COSOLZZFQIVEIH-CDLHYRBUSA-N
Standard InCHI	InChI=1S/C47H76O18/c1-41(2)25-7-11-44(5)26(8-12-47-27-15-42(3,20-50)13-14-46(27,21-60-47)28(51)16-45(44,47)6)43(25,4)10-9-29(41)64-40-37(65-39-36(58)34(56)31(53)23(18-49)62-39)32(54)24(19-59-40)63-38-35(57)33(55)30(52)22(17-48)61-38/h20,22-40,48-49,51-58H,7-19,21H2,1-6H3/t22-,23-,24+,25+,26-,27-,28-,29+,30-,31-,32+,33+,34+,35-,36-,37-,38+,39+,40+,42+,43+,44-,45+,46-,47+/m1/s1
SMILES	CC1(C)[C@@H]2CC[C@]3(C)[C@H](CC[C@]45[C@@H]6C[C@](C)(CC[C@]6(CO5)[C@@H](C[C@@]34C)O)C=O)[C@@]2(C)CC[C@@H]1O[C@H]1[C@@H]([C@H]([C@H](CO1)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	928.5	Volume:	900.047 ? Van der Waals volume.
Dense:	1.032	LogP:	0.268 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.092 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.904 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	48.0
TPSA:	283.98 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	9.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.104	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.653	Fsp³:	0.979
MCE-18:	255.753 ? 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:	0.925	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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.206	Promiscuous compounds:	0.019

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.393	MDCK Permeability:	-5.074
Pgp-inhibitor:	0.0	Pgp-substrate:	0.289
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):	0.229
20% Bioavailability (F20%):	0.242	30% Bioavailability (F30%):	0.991
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.225	MRP1:	0.007
Plasma Protein Binding (PPB):	65.046%	Volume Distribution (VD):	-0.378
Fu:	28.329% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.148
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.355
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):

0.111

Half-life (T1/2):

3.219

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.01
Human Hepatotoxicity (H-HT):	0.694	Drug-induced Liver Injury (DILI):	0.846
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.005	Skin Sensitization:	1.0
Carcinogencity:	0.364	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.808	Drug-induced Nephrotoxicity:	0.889
Genotoxicity:	0.957	RPMI-8226 Immunitoxicity:	0.241
A549 Cytotoxicity:	0.886	Hek293 Cytotoxicity:	0.792
BCF:	0.935 ? 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:	3.513 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.211 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.328 ? 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
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9090874]
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23245	Ardisia mamillata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15237	Cyclamen mirabile	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23245	Ardisia mamillata	Species	Primulaceae	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
Activity	1
MIC	11

Activity Type	# Activity
Organism	11
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
NPT188	Organism	Candida parapsilosis	Candida parapsilosis	MIC	=	80.0	ug.mL-1	PMID[9090874]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Activity	=	46.2	10'-6M	PMID[9090874]
NPT20	Organism	Candida albicans	Candida albicans	MIC	=	160.0	ug.mL-1	PMID[9090874]
NPT3153	Organism	Kluyveromyces marxianus	Kluyveromyces marxianus	MIC	=	160.0	ug.mL-1	PMID[9090874]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	MIC	=	80.0	ug.mL-1	PMID[9090874]
NPT187	Organism	Issatchenkia orientalis	Pichia kudriavzevii	MIC	>	320.0	ug.mL-1	PMID[9090874]
NPT18	Organism	Pseudomonas aeruginosa	Pseudomonas aeruginosa	MIC	>	400.0	ug.mL-1	PMID[9090874]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	400.0	ug.mL-1	PMID[9090874]
NPT175	Organism	Enterococcus faecalis	Enterococcus faecalis	MIC	>	400.0	ug.mL-1	PMID[9090874]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	400.0	ug.mL-1	PMID[9090874]
NPT186	Organism	Candida tropicalis	Candida tropicalis	MIC	=	160.0	ug.mL-1	PMID[9090874]

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 NPC158051 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	24280
0.1-0.2	21982
0.2-0.3	2707
0.3-0.4	723
0.4-0.5	115
0.5-0.6	9
0.6-0.7	14
0.7-0.8	0
0.8-0.85	2
0.85-0.9	6
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8936	High Similarity	NPC40716
0.8876	High Similarity	NPC18724
0.8778	High Similarity	NPC224003
0.875	High Similarity	NPC138219
0.875	High Similarity	NPC475234
0.866	High Similarity	NPC473688
0.8235	Intermediate Similarity	NPC262567
0.8	Intermediate Similarity	NPC475630
0.7959	Intermediate Similarity	NPC253611
0.7959	Intermediate Similarity	NPC488782
0.7925	Intermediate Similarity	NPC231566
0.7879	Intermediate Similarity	NPC267238
0.7879	Intermediate Similarity	NPC77717
0.767	Intermediate Similarity	NPC209798
0.7636	Intermediate Similarity	NPC471626
0.76	Intermediate Similarity	NPC158367
0.7477	Intermediate Similarity	NPC471431
0.7327	Intermediate Similarity	NPC119628
0.729	Intermediate Similarity	NPC205129
0.7282	Intermediate Similarity	NPC148593
0.7282	Intermediate Similarity	NPC157571
0.7282	Intermediate Similarity	NPC471373
0.7238	Intermediate Similarity	NPC471375
0.7156	Intermediate Similarity	NPC471425
0.7091	Intermediate Similarity	NPC189575
0.7037	Intermediate Similarity	NPC126753
0.7027	Intermediate Similarity	NPC471429
0.7009	Intermediate Similarity	NPC51579
0.6991	Remote Similarity	NPC471427
0.6903	Remote Similarity	NPC106701
0.6842	Remote Similarity	NPC471424
0.6842	Remote Similarity	NPC471426
0.6796	Remote Similarity	NPC171741
0.6752	Remote Similarity	NPC471428
0.6606	Remote Similarity	NPC471374
0.6542	Remote Similarity	NPC207693
0.6542	Remote Similarity	NPC470623
0.6538	Remote Similarity	NPC323231
0.6422	Remote Similarity	NPC184805
0.6364	Remote Similarity	NPC273189
0.6036	Remote Similarity	NPC87393
0.6034	Remote Similarity	NPC470622
0.5785	Remote Similarity	NPC22709
0.5738	Remote Similarity	NPC471430
0.5439	Remote Similarity	NPC471435
0.5439	Remote Similarity	NPC471434
0.5328	Remote Similarity	NPC66513
0.5229	Remote Similarity	NPC80640
0.5167	Remote Similarity	NPC185466
0.5088	Remote Similarity	NPC204392
0.5086	Remote Similarity	NPC123796

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC158051 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7361
0.1-0.2	1734
0.2-0.3	53
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