NPASS Compound

Natural Product: NPC216037

Natural Product ID	NPC216037
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GOTSIHVHBCEBJP-CBBBAJFRSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	56601862
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 141148 0 0 0 0 0 0 0 0999 V2000 9.2756 2.9395 0.8300 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4141 1.5437 0.2584 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9199 1.2314 0.2581 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9983 1.5727 -1.1790 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9806 0.2187 -1.7583 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4501 -0.8916 -0.8971 C 0 0 1 0 0 0 0 0 0 0 0 0 9.7086 -1.6658 -0.5373 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0225 -1.8417 0.6117 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8335 -0.4537 0.4188 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6405 0.5919 1.1107 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3703 -0.3381 0.4909 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7435 0.9568 0.8190 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1816 2.0567 0.7415 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3149 0.8661 1.3352 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5570 0.0996 0.2845 C 0 0 2 0 0 0 0 0 0 0 0 0 2.0522 0.1056 0.5066 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6442 -0.4629 1.8141 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6278 1.5534 0.4938 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3024 1.8951 -0.0175 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6397 0.7810 -0.3743 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0066 -0.4452 -0.8811 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2164 -0.5454 -2.4120 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7256 -1.6703 -0.3558 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4644 -0.5507 -0.6955 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9029 -1.9701 -0.7728 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4040 -2.0160 -1.0594 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1793 -1.2039 -0.0701 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3031 -2.1050 1.1602 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5597 -0.8768 -0.6591 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3362 0.1386 -1.7569 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2071 -2.0492 -1.3047 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6243 -1.8759 -1.6602 C 0 0 1 0 0 0 0 0 0 0 0 0 7.7774 -1.5307 -3.0326 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5066 0.5261 0.6895 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8188 0.8331 0.4588 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7455 -0.1260 1.0980 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7694 0.6325 1.9814 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3310 1.7447 1.1413 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1950 2.6589 0.7473 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9783 2.1025 1.1380 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2600 2.4806 1.8855 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4630 2.4590 1.2118 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6017 1.9139 2.0165 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.8175 1.8744 1.1039 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.0110 3.2644 0.5452 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7616 3.6682 -0.1701 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.9183 5.0284 -0.8258 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7234 5.4190 -1.4271 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7543 3.7724 0.7983 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0842 3.3441 -0.3255 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9006 1.4664 1.8781 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3107 0.6285 2.4479 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0379 1.1619 3.0415 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4066 -0.9788 0.2594 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3044 -2.3307 0.5680 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7230 -2.7604 0.9832 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0160 -4.1838 0.5547 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8989 -4.2512 -0.9436 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7028 -3.4734 -1.4274 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1347 -2.2961 -2.2772 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0180 -2.6907 -3.2821 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8324 -3.1317 -0.4326 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8712 -5.5710 -1.4000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3009 -4.4791 1.0007 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7739 -2.7077 2.3709 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2440 3.4581 0.7219 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4705 3.4828 0.2877 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0138 2.8607 1.9234 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1984 0.5895 1.1110 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2466 0.8128 -0.7175 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5206 2.1732 0.3836 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0248 2.0802 -1.2611 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7381 2.2082 -1.7112 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0287 0.0233 -2.1483 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4076 0.2647 -2.7276 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3254 -2.0605 -1.3252 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0775 -1.3912 1.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4265 0.1717 1.8195 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9808 1.1408 1.8485 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0410 -0.9709 1.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8625 1.8544 1.4290 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3373 0.4221 2.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6387 0.7908 -0.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4127 -0.1526 2.5825 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4331 -1.5285 1.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7296 0.0568 2.1696 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6980 1.9043 1.5690 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4447 2.1682 0.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2719 2.5528 0.6967 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4433 2.5746 -0.9104 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3122 1.1962 -1.1788 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1469 -1.5752 -2.7560 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5744 0.0734 -2.8577 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1821 -0.0566 -2.6781 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0303 -1.5549 0.7035 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2577 -2.6212 -0.6097 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7047 -1.6686 -0.9284 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9708 -0.0326 -1.5692 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6472 -2.5959 0.0929 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4417 -2.4332 -1.6807 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6617 -3.1136 -0.9344 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5694 -1.8131 -2.1108 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4407 -2.8425 1.1968 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2596 -1.5882 2.1087 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1876 -2.7870 1.0897 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0664 -0.0115 -2.6097 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4484 1.1709 -1.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3753 0.0296 -2.2996 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0069 -3.0157 -0.7529 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6455 -2.2158 -2.2772 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0598 -2.9263 -1.6580 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6915 -1.7587 -3.3520 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0609 1.1258 -0.5805 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1930 -0.7331 1.8482 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5469 -0.0057 2.3740 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7881 1.3337 0.2385 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1628 2.7021 -0.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3154 3.6877 1.0928 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4036 1.8683 0.2521 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8030 2.5835 2.8647 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6391 1.1305 0.2849 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1334 3.9409 1.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4719 2.8925 -0.8913 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6799 4.9326 -1.6126 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2052 5.7359 -0.0269 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9893 5.5338 -0.7820 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5019 4.2375 -0.2213 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6728 1.3907 1.2512 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0852 0.2958 2.9734 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1747 0.5868 3.8549 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6638 -2.4807 1.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4814 -2.0456 0.6108 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3157 -4.8535 1.0905 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8055 -3.7772 -1.3703 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1411 -4.1460 -2.1300 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7079 -1.5536 -1.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2687 -1.8180 -2.7634 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9640 -2.5460 -3.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8994 -5.8362 -1.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3207 -4.7505 1.9392 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7263 -2.8339 2.6753 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 1 7 8 2 0 6 9 1 0 9 10 1 0 9 11 1 0 11 12 1 0 12 13 2 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 1 6 29 31 1 0 31 32 1 0 32 33 1 0 20 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 10 2 1 0 29 11 1 0 40 35 1 0 49 42 1 0 62 55 1 0 32 6 1 0 27 15 1 0 24 16 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 0 4 73 1 0 5 74 1 0 5 75 1 0 7 76 1 0 9 77 1 1 10 78 1 0 10 79 1 0 11 80 1 1 14 81 1 0 14 82 1 0 15 83 1 6 17 84 1 0 17 85 1 0 17 86 1 0 18 87 1 0 18 88 1 0 19 89 1 0 19 90 1 0 20 91 1 6 22 92 1 0 22 93 1 0 22 94 1 0 23 95 1 0 23 96 1 0 23 97 1 0 24 98 1 6 25 99 1 0 25100 1 0 26101 1 0 26102 1 0 28103 1 0 28104 1 0 28105 1 0 30106 1 0 30107 1 0 30108 1 0 31109 1 0 31110 1 0 32111 1 6 33112 1 0 35113 1 6 36114 1 1 37115 1 1 38116 1 6 39117 1 0 39118 1 0 42119 1 6 43120 1 1 44121 1 6 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 1 56132 1 6 57133 1 1 58134 1 6 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	GOTSIHVHBCEBJP-CBBBAJFRSA-N
Standard InCHI	InChI=1S/C47H76O18/c1-42(2)12-13-47(20-50)21(15-42)30-22(51)14-27-44(5)10-9-29(43(3,4)26(44)8-11-45(27,6)46(30,7)16-28(47)52)64-41-38(65-40-37(59)35(57)32(54)24(18-49)62-40)33(55)25(19-60-41)63-39-36(58)34(56)31(53)23(17-48)61-39/h20-21,23-41,48-49,52-59H,8-19H2,1-7H3/t21-,23+,24+,25-,26-,27+,28+,29-,30-,31+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41-,44-,45+,46+,47+/m0/s1
SMILES	CC1(C)CC[C@@]2(C=O)[C@@H](C1)[C@H]1C(=O)C[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[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:	905.967 ? Van der Waals volume.
Dense:	1.025	LogP:	0.372 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.349 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.47 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	46.0
TPSA:	291.82 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	8.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.105	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.478	Fsp³:	0.957
MCE-18:	175.304 ? 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:	0.885	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? 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:	0.181	Promiscuous compounds:	0.058

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.266	MDCK Permeability:	-5.149
Pgp-inhibitor:	0.0	Pgp-substrate:	0.06
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):	0.271
20% Bioavailability (F20%):	0.706	30% Bioavailability (F30%):	0.994
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.391	MRP1:	0.031
Plasma Protein Binding (PPB):	66.687%	Volume Distribution (VD):	-0.454
Fu:	26.82% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.007
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.023	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.192	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.33
HLM stability:	0.001 ? 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):

0.131

Half-life (T1/2):

2.757

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.004
Human Hepatotoxicity (H-HT):	0.708	Drug-induced Liver Injury (DILI):	0.923
AMES Toxicity:	0.996	Rat Oral Acute Toxicity:	0.008
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.367	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.003	Ototoxicity:	0.999
Hematotoxicity:	0.965	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.934	RPMI-8226 Immunitoxicity:	0.365
A549 Cytotoxicity:	0.983	Hek293 Cytotoxicity:	0.777
BCF:	0.631 ? 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:	3.348 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.91 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.02 ? 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
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21928797]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21278	Lysimachia clethroides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21278	Lysimachia clethroides	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

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 NPC216037 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	23356
0.1-0.2	22536
0.2-0.3	2931
0.3-0.4	803
0.4-0.5	205
0.5-0.6	26
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	Natural Product ID
0.5962	Remote Similarity	NPC18724
0.5849	Remote Similarity	NPC158051
0.5463	Remote Similarity	NPC224003
0.5398	Remote Similarity	NPC253611
0.5398	Remote Similarity	NPC488782
0.5351	Remote Similarity	NPC77717
0.5315	Remote Similarity	NPC204392
0.531	Remote Similarity	NPC257468
0.5304	Remote Similarity	NPC157571
0.5304	Remote Similarity	NPC40716
0.5259	Remote Similarity	NPC184805
0.5254	Remote Similarity	NPC209798
0.5214	Remote Similarity	NPC138219
0.5214	Remote Similarity	NPC273189
0.5214	Remote Similarity	NPC475234
0.5175	Remote Similarity	NPC123796
0.5169	Remote Similarity	NPC473688
0.5169	Remote Similarity	NPC471375
0.513	Remote Similarity	NPC471435
0.513	Remote Similarity	NPC471434
0.5128	Remote Similarity	NPC488564
0.5086	Remote Similarity	NPC207693
0.5082	Remote Similarity	NPC262567
0.5043	Remote Similarity	NPC323359
0.5043	Remote Similarity	NPC606145
0.5041	Remote Similarity	NPC471425

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC216037 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7134
0.1-0.2	1956
0.2-0.3	56
0.3-0.4	4
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