NPASS Compound

Natural Product: NPC477350

Natural Product ID	NPC477350
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Tyrianthin 9
IUPAC Name	[(1S,3R,4R,5R,6R,8S,10R,11R,12R,13R,15R,29R,30R,31R,33R)-4,5,11,12-tetrahydroxy-6-(hydroxymethyl)-13,31-dimethyl-27-oxo-17-pentyl-30-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,7,9,14,16,28,32-heptaoxatetracyclo[27.3.1.03,8.010,15]tritriacontan-33-yl] propanoate
Synonyms	Tyrianthin 9
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44579633
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0000198] Oligosaccharides

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 137141 0 0 0 0 0 0 0 0999 V2000 10.0102 -2.4126 2.1174 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7062 -2.1611 1.3472 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5007 -0.6677 1.3573 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2311 -0.2424 0.6230 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0254 -0.8733 1.2822 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7182 -0.5172 0.6351 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6029 -1.2038 1.3870 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6780 -2.7182 1.3168 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5356 -3.2265 2.1612 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3733 -4.7241 2.0973 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2199 -5.1254 3.0251 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0057 -4.3197 2.7014 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4847 -4.4989 1.2710 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5369 -3.4669 1.0530 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7279 -3.5821 1.9578 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6091 -2.3757 1.7361 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7015 -2.3042 2.3273 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2163 -1.3668 0.9005 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9406 -0.1974 0.6361 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3149 -0.1793 -0.8273 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0148 -0.4644 -1.5652 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2510 0.6623 -1.4704 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9047 1.0557 -0.1963 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9899 1.0119 0.8220 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4543 0.7990 2.1151 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7478 1.6029 3.1939 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5320 2.5693 3.0229 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1749 1.3715 4.5469 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7133 2.4299 5.4751 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4669 2.3698 -0.3228 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2338 2.6292 0.2809 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3859 4.1045 0.7328 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7103 4.8336 -0.5854 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5429 4.8387 -1.4391 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4297 3.9568 -0.8738 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9060 2.6684 -0.7123 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9274 1.7553 -0.4516 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1384 2.1944 -0.9657 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0764 2.3332 -2.4922 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3782 1.9159 -3.1477 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5922 2.2259 -2.3130 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4373 2.0016 -0.9742 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2581 1.2755 -0.6718 C 0 0 1 0 0 0 0 0 0 0 0 0 4.4174 0.8376 0.6170 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9820 3.6679 -2.5327 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5375 2.6670 -4.3378 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1047 1.4851 -3.0442 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2096 6.2207 -1.3760 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3994 6.2062 -2.0688 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2526 6.0733 -0.3723 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4763 4.3018 1.5334 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2771 -0.7501 -3.0218 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3075 -1.1011 -1.1217 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4513 -0.5513 -1.6748 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6666 -0.6978 -0.8392 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8789 -0.8393 -1.7299 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.7071 -2.1196 -2.5304 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.2964 -2.2082 -3.0802 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.6290 -0.9974 -2.9479 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4200 -2.5285 -4.5547 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.6799 -2.1784 -3.4960 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0021 -0.8892 -0.9208 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6127 -1.8837 -0.0657 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6709 -1.5595 1.9203 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7666 -2.3976 3.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4582 -3.3892 1.8397 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8782 -2.7138 1.8351 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9168 -2.4996 0.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4003 -0.2197 0.9004 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4852 -0.2790 2.4039 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2209 0.8672 0.7179 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3105 -0.4890 -0.4396 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0286 -0.7634 2.3659 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1544 -1.9815 1.0866 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7324 -0.9110 -0.4244 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5996 -0.8948 1.0369 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6501 -0.9267 2.4594 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6907 -3.1097 0.3019 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6125 -3.0818 1.8249 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5787 -2.7370 1.8576 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7801 -2.9775 3.2247 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2702 -5.2397 2.4794 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1332 -5.1128 1.1039 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9862 -6.1948 2.8566 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4764 -4.9879 4.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8311 -4.7826 3.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0292 -3.2798 3.0268 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8728 -5.5196 1.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3410 -4.3165 0.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1282 -2.4226 1.0889 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9453 -3.5559 0.0013 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4741 -3.6875 3.0148 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3262 -4.4561 1.6301 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7999 -0.0323 1.2988 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5954 0.8585 -1.0852 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5271 -1.3697 -1.1228 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0614 0.4400 0.2108 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6391 1.8827 0.7228 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0768 1.4412 4.5530 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4421 0.3682 4.9398 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7084 3.4223 5.0058 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1189 2.4674 6.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7586 2.1680 5.8174 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0311 2.0059 1.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5618 4.5113 1.1007 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4584 4.1972 -1.1294 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2977 4.5975 -2.4876 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4604 2.3874 -1.6857 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4032 3.2048 -0.5626 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9167 3.3947 -2.7816 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3544 0.8512 -3.4739 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4150 1.5883 -2.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1689 0.3880 -1.3325 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2241 4.2282 -3.1113 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0683 4.1769 -1.5577 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0026 3.7644 -2.9985 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4777 2.7668 -4.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5242 0.5904 -3.1099 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5173 7.0161 -1.7274 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4277 6.4116 -0.3014 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1674 6.4725 -1.4883 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9666 6.2332 -1.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3104 4.5088 1.0391 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6346 -1.7747 -3.2081 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0726 -0.0740 -3.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3866 -0.5541 -3.6559 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2311 0.5582 -1.7438 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8730 0.1766 -0.1842 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9728 0.0051 -2.4243 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8442 -2.9603 -1.8261 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7592 -3.0218 -2.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1673 -3.3383 -4.7326 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4822 -2.8378 -5.0202 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8078 -1.6525 -5.1336 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0650 -1.2766 -3.7089 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7258 -1.4416 -1.3162 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2286 -1.8236 0.7078 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 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 1 0 15 16 1 0 16 17 2 0 16 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 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 23 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 36 37 1 0 37 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 41 45 1 0 40 46 1 0 39 47 1 0 34 48 1 0 48 49 1 0 33 50 1 0 32 51 1 0 21 52 1 0 20 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 58 60 1 0 57 61 1 0 56 62 1 0 55 63 1 0 44 6 1 0 24 19 1 0 36 31 1 0 43 38 1 0 59 54 1 0 1 64 1 0 1 65 1 0 1 66 1 0 2 67 1 0 2 68 1 0 3 69 1 0 3 70 1 0 4 71 1 0 4 72 1 0 5 73 1 0 5 74 1 0 6 75 1 0 7 76 1 0 7 77 1 0 8 78 1 0 8 79 1 0 9 80 1 0 9 81 1 0 10 82 1 0 10 83 1 0 11 84 1 0 11 85 1 0 12 86 1 0 12 87 1 0 13 88 1 0 13 89 1 0 14 90 1 0 14 91 1 0 15 92 1 0 15 93 1 0 19 94 1 1 20 95 1 6 21 96 1 1 23 97 1 1 24 98 1 1 28 99 1 0 28100 1 0 29101 1 0 29102 1 0 29103 1 0 31104 1 1 32105 1 1 33106 1 6 34107 1 6 36108 1 6 38109 1 1 39110 1 1 40111 1 6 41112 1 6 43113 1 6 45114 1 0 45115 1 0 45116 1 0 46117 1 0 47118 1 0 48119 1 0 48120 1 0 49121 1 0 50122 1 0 51123 1 0 52124 1 0 52125 1 0 52126 1 0 54127 1 6 55128 1 1 56129 1 6 57130 1 1 58131 1 1 60132 1 0 60133 1 0 60134 1 0 61135 1 0 62136 1 0 63137 1 0 M END

Standard InCHIKey	PVATZCKYGRERLI-XIZJVXPQSA-N
Standard InCHI	InChI=1S/C43H74O20/c1-6-8-14-17-24-18-15-12-10-9-11-13-16-19-27(46)60-38-35(61-40-34(53)31(50)28(47)21(3)54-40)23(5)56-43(39(38)59-26(45)7-2)63-37-33(52)30(49)25(20-44)58-42(37)62-36-32(51)29(48)22(4)55-41(36)57-24/h21-25,28-44,47-53H,6-20H2,1-5H3/t21-,22-,23-,24?,25-,28+,29+,30+,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41+,42+,43+/m1/s1
SMILES	CCCCCC1CCCCCCCCCC(=O)O[C@@H]2[C@@H]([C@H](O[C@H]([C@@H]2OC(=O)CC)O[C@@H]3[C@@H]([C@H]([C@H](O[C@H]3O[C@@H]4[C@@H]([C@H]([C@H](O[C@H]4O1)C)O)O)CO)O)O)C)O[C@@H]5[C@@H]([C@@H]([C@H]([C@H](O5)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	910.48	Volume:	880.033 ? Van der Waals volume.
Dense:	1.035	LogP:	1.934 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.718 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.456 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	44.0
TPSA:	288.28 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	8.0	Rings:	5.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.114	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.159	Fsp³:	0.953
MCE-18:	103.143 ? 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:	0.791	Fluc inhibitor:	0.325 ? 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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.45	Promiscuous compounds:	0.147

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.757	MDCK Permeability:	-4.933
Pgp-inhibitor:	0.0	Pgp-substrate:	0.976
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):	0.362
20% Bioavailability (F20%):	0.192	30% Bioavailability (F30%):	0.693
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.992
Plasma Protein Binding (PPB):	77.95%	Volume Distribution (VD):	-0.231
Fu:	13.277% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.309
OATP1B3 inhibitor:	0.941	BCRP inhibitor:	0.001
BSEP inhibitor:	0.625

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:	0.006
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.962
HLM stability:	0.993 ? 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):

0.675

Half-life (T1/2):

2.541

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.164
Human Hepatotoxicity (H-HT):	0.78	Drug-induced Liver Injury (DILI):	0.997
AMES Toxicity:	0.976	Rat Oral Acute Toxicity:	0.007
Maximum Recommended Daily Dose:	0.006	Skin Sensitization:	1.0
Carcinogencity:	0.001	Eye Corrosion:	0.0
Eye Irritation:	0.009	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.012	Ototoxicity:	0.999
Hematotoxicity:	0.961	Drug-induced Nephrotoxicity:	0.977
Genotoxicity:	0.001	RPMI-8226 Immunitoxicity:	0.574
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.566
BCF:	0.46 ? 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:	3.215 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.84 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.858 ? 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
NPO4441	Ipomoea tyrianthina	Species	Convolvulaceae	Eukaryota	roots	n.a.	n.a.	PMID[17309299]
NPO4441	Ipomoea tyrianthina	Species	Convolvulaceae	Eukaryota	Roots	states of Puebla, Morelos, and Distrito Federal, Mexico	2000-2005	PMID[18826278]
NPO4441	Ipomoea tyrianthina	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4441	Ipomoea tyrianthina	Species	Convolvulaceae	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
MIC	1
ED50	4
Activity	1

Activity Type	# Activity
Cell line	3
Organism	2
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
NPT91	Cell line	KB	Homo sapiens	ED50	=	2.5	ug/ml	PMID[18826278]
NPT382	Cell line	OVCAR-5	Homo sapiens	ED50	>	5	ug/ml	PMID[18826278]
NPT148	Cell line	HCT-15	Homo sapiens	ED50	>	5	ug/ml	PMID[18826278]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	=	25	ug/ml	PMID[18826278]
NPT2	Others	Unspecified	n.a.	ED50	>	5	ug/ml	PMID[18826278]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	70	%	PMID[18826278]

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 NPC477350 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	23412
0.1-0.2	22113
0.2-0.3	3794
0.3-0.4	384
0.4-0.5	38
0.5-0.6	48
0.6-0.7	43
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8714	High Similarity	NPC22742
0.8714	High Similarity	NPC477349
0.8714	High Similarity	NPC477346
0.8082	Intermediate Similarity	NPC604005
0.8082	Intermediate Similarity	NPC605014
0.7867	Intermediate Similarity	NPC600446
0.7867	Intermediate Similarity	NPC605013
0.7639	Intermediate Similarity	NPC146380
0.7532	Intermediate Similarity	NPC109887
0.7432	Intermediate Similarity	NPC281563
0.7403	Intermediate Similarity	NPC477344
0.7403	Intermediate Similarity	NPC477326
0.7273	Intermediate Similarity	NPC478734
0.725	Intermediate Similarity	NPC472204
0.7237	Intermediate Similarity	NPC113745
0.7237	Intermediate Similarity	NPC477320
0.7237	Intermediate Similarity	NPC477323
0.7237	Intermediate Similarity	NPC477325
0.7237	Intermediate Similarity	NPC609436
0.7222	Intermediate Similarity	NPC606819
0.7215	Intermediate Similarity	NPC146992
0.7215	Intermediate Similarity	NPC85759
0.7089	Intermediate Similarity	NPC478733
0.7051	Intermediate Similarity	NPC89843
0.7037	Intermediate Similarity	NPC294748
0.6988	Remote Similarity	NPC184915
0.6988	Remote Similarity	NPC259294
0.6986	Remote Similarity	NPC478729
0.6974	Remote Similarity	NPC477329
0.6933	Remote Similarity	NPC475425
0.6914	Remote Similarity	NPC297768
0.6914	Remote Similarity	NPC173328
0.6867	Remote Similarity	NPC238056
0.6829	Remote Similarity	NPC186992
0.6824	Remote Similarity	NPC44782
0.679	Remote Similarity	NPC267592
0.6786	Remote Similarity	NPC183888
0.6786	Remote Similarity	NPC224953
0.6769	Remote Similarity	NPC206823
0.6747	Remote Similarity	NPC238264
0.6747	Remote Similarity	NPC483170
0.6747	Remote Similarity	NPC477345
0.6707	Remote Similarity	NPC478724
0.6667	Remote Similarity	NPC169345
0.6627	Remote Similarity	NPC307400
0.6627	Remote Similarity	NPC27289
0.6627	Remote Similarity	NPC119583
0.6623	Remote Similarity	NPC477328
0.6623	Remote Similarity	NPC477330
0.6588	Remote Similarity	NPC126685
0.6543	Remote Similarity	NPC158302
0.6522	Remote Similarity	NPC28069
0.6506	Remote Similarity	NPC477319
0.6471	Remote Similarity	NPC115013
0.6429	Remote Similarity	NPC143421
0.6386	Remote Similarity	NPC478725
0.6364	Remote Similarity	NPC478728
0.6341	Remote Similarity	NPC216883
0.6322	Remote Similarity	NPC123204
0.631	Remote Similarity	NPC478723
0.631	Remote Similarity	NPC476781
0.6292	Remote Similarity	NPC478727
0.6279	Remote Similarity	NPC290012
0.622	Remote Similarity	NPC477331
0.622	Remote Similarity	NPC477332
0.619	Remote Similarity	NPC478722
0.617	Remote Similarity	NPC77651
0.6163	Remote Similarity	NPC478726
0.5979	Remote Similarity	NPC290276
0.5955	Remote Similarity	NPC163409
0.5941	Remote Similarity	NPC472352
0.5909	Remote Similarity	NPC478731
0.5862	Remote Similarity	NPC478730
0.5795	Remote Similarity	NPC476087
0.5795	Remote Similarity	NPC475667
0.5789	Remote Similarity	NPC124878
0.5789	Remote Similarity	NPC231888
0.5778	Remote Similarity	NPC472200
0.5747	Remote Similarity	NPC472205
0.573	Remote Similarity	NPC478732
0.573	Remote Similarity	NPC477317
0.573	Remote Similarity	NPC477318
0.5729	Remote Similarity	NPC35338
0.5729	Remote Similarity	NPC204214
0.5729	Remote Similarity	NPC92283
0.5667	Remote Similarity	NPC475270
0.5667	Remote Similarity	NPC475327
0.5657	Remote Similarity	NPC10883
0.5652	Remote Similarity	NPC476783
0.5638	Remote Similarity	NPC475241
0.5632	Remote Similarity	NPC479061
0.5631	Remote Similarity	NPC471026
0.5604	Remote Similarity	NPC475525
0.5604	Remote Similarity	NPC475540
0.5568	Remote Similarity	NPC44682
0.5568	Remote Similarity	NPC479060
0.5567	Remote Similarity	NPC63404
0.5543	Remote Similarity	NPC476066
0.5543	Remote Similarity	NPC269318
0.5507	Remote Similarity	NPC241265
0.55	Remote Similarity	NPC10121
0.55	Remote Similarity	NPC198918
0.5484	Remote Similarity	NPC475164
0.5426	Remote Similarity	NPC473605
0.5426	Remote Similarity	NPC475375
0.5426	Remote Similarity	NPC476782
0.5392	Remote Similarity	NPC471025
0.5385	Remote Similarity	NPC600940
0.5362	Remote Similarity	NPC76881
0.5227	Remote Similarity	NPC479059
0.5205	Remote Similarity	NPC190418
0.5192	Remote Similarity	NPC600721
0.5192	Remote Similarity	NPC605872
0.5179	Remote Similarity	NPC147032
0.5093	Remote Similarity	NPC471024
0.5049	Remote Similarity	NPC611287

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC477350 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7384
0.1-0.2	1676
0.2-0.3	85
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