NPASS Compound

Natural Product: NPC514132

Natural Product ID	NPC514132
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Momordin IIc
IUPAC Name	(2~{S},3~{S},4~{S},5~{R},6~{R})-6-[[(3~{S},4~{a}~{R},6~{a}~{R},6~{b}~{S},8~{a}~{S},12~{a}~{S},14~{a}~{R},14~{b}~{R})-4,4,6~{a},6~{b},11,11,14~{b}-heptamethyl-8~{a}-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxycarbonyl-1,2,3,4~{a},5,6,7,8,9,10,12,12~{a},14,14~{a}-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2~{S},3~{R},4~{S},5~{R})-3,4,5-trihydroxytetrahydropyran-2-yl]oxy-tetrahydropyran-2-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 139146 0 0 0 0 0 0 0 0999 V2000 -5.7075 -1.9008 -4.6413 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8466 -1.6969 -3.1263 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3621 -2.9915 -2.5644 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7824 -0.5320 -2.8835 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0553 0.7809 -2.8093 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1716 0.8618 -1.5455 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0265 1.2363 -0.3799 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7199 2.2537 0.2762 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1249 0.5223 0.0034 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9866 0.7755 1.0717 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1925 -0.3071 1.8903 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9810 0.0502 2.9753 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9179 -0.9956 4.0756 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7336 -0.5563 5.1161 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4015 0.2200 2.4974 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0045 1.3480 3.0559 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4189 0.2307 1.0036 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1178 -1.0616 0.5534 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3432 1.1357 0.4414 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6525 2.4815 0.6342 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2206 1.9762 -1.8132 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0221 2.0272 -0.9378 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2681 0.7261 -0.9092 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5440 0.5981 -2.2383 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1563 -0.4504 -0.8099 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7377 -1.5501 -0.2451 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3898 -1.7819 0.3481 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5028 -0.5935 0.1093 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7942 -0.5932 0.8379 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6460 -0.6239 2.3355 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6149 -1.7930 0.4552 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5021 -1.6069 -0.7207 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5035 -0.4886 -0.5380 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7021 -0.9470 -0.0436 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7682 -0.8164 -0.9331 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1846 -2.0635 -1.2191 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1095 -2.7288 -0.5295 C 0 0 2 0 0 0 0 0 0 0 0 0 6.4642 -3.8746 0.1820 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2360 -4.0591 0.0423 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1700 -4.7465 0.9940 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7048 -1.8461 0.5387 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7445 -2.4617 1.2174 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1269 -0.5779 -0.1565 C 0 0 2 0 0 0 0 0 0 0 0 0 8.9101 0.1637 0.6692 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1508 0.5040 0.1413 C 0 0 2 0 0 0 0 0 0 0 0 0 11.2338 0.0660 0.8440 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2248 0.5899 2.1330 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6184 2.0583 2.0036 C 0 0 1 0 0 0 0 0 0 0 0 0 12.8412 2.3278 2.5685 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5381 2.4872 0.5546 C 0 0 2 0 0 0 0 0 0 0 0 0 11.4833 3.8998 0.5427 O 0 0 0 0 0 0 0 0 0 0 0 0 10.2803 1.9805 -0.1101 C 0 0 1 0 0 0 0 0 0 0 0 0 10.3886 2.2130 -1.4712 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8222 0.1589 -0.5067 C 0 0 1 0 0 0 0 0 0 0 0 0 7.1434 0.9780 -1.5814 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9983 0.6017 0.3883 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5963 0.5387 1.7496 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4356 1.9672 -0.1875 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5167 0.6292 0.3290 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8647 1.8770 0.8414 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5209 1.9378 0.2404 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3003 0.6760 0.2745 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1324 0.6534 1.5396 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5567 -0.4715 -1.3605 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4959 -1.3086 -2.6136 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5437 -2.9739 -4.8778 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8457 -1.3131 -5.0277 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6683 -1.6145 -5.1215 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0831 -2.8439 -1.7366 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8794 -3.6178 -3.3203 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5127 -3.6307 -2.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4482 -0.4628 -3.7735 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4182 -0.7441 -2.0189 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8127 1.5780 -2.6768 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3933 0.8976 -3.6653 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7138 1.6478 1.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6059 0.9977 3.4517 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2032 -1.9996 3.6971 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8915 -1.0885 4.4832 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1916 -1.3041 5.5854 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9919 -0.6558 2.8954 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9875 1.2096 2.9865 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3863 0.5681 0.5784 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4038 -1.1966 -0.3915 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3390 0.9856 -0.6588 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5897 2.6350 0.8979 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9712 2.0241 -2.9134 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7689 2.9541 -1.6482 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2593 2.4356 0.0494 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3203 2.7757 -1.4138 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5440 1.0636 -2.2494 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5314 -0.4520 -2.6026 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1339 1.1616 -3.0215 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4128 -2.4090 -0.1815 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5257 -2.0790 1.3863 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9785 -2.6718 -0.1744 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2405 -0.6440 -0.9914 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0075 -1.4969 2.6632 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1850 0.2520 2.7834 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6094 -0.8106 2.8518 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0017 -2.7006 0.2911 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2932 -2.0853 1.3150 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9531 -1.5454 -1.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1169 -2.5407 -0.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6004 -0.0455 -1.5547 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2859 -0.3844 -1.8653 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9500 -3.1480 -1.1454 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7107 -5.3903 1.6206 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8872 -1.5845 1.2726 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9678 -1.9605 2.0353 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5679 -0.8349 -1.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1644 0.0043 -0.8689 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9728 0.0347 2.7365 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2286 0.4370 2.5449 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8446 2.6358 2.5479 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5902 1.8403 2.1451 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4615 2.1802 0.0565 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3400 4.2247 -0.3851 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4491 2.5622 0.3501 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3999 1.4050 -2.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5335 0.7019 0.4113 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7364 1.8774 -1.5127 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5704 1.0885 1.7273 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9663 1.1120 2.4583 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8651 -0.4768 2.0954 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5133 2.7250 0.5987 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7444 2.2310 -1.0011 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4311 1.7833 -0.6491 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2898 0.6497 -0.7878 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4241 2.7625 0.4666 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8641 1.9604 1.9467 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1081 2.7026 0.8306 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4291 2.4059 -0.7644 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8785 1.5468 2.1857 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1005 -0.2807 2.0963 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1974 0.8173 1.2805 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2190 -1.0403 -0.6424 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9369 -2.2421 -2.3791 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9845 -0.7128 -3.4052 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 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 15 16 1 0 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 6 21 1 0 21 22 1 0 22 23 1 0 23 24 1 6 23 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 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 2 0 38 40 1 0 37 41 1 0 41 42 1 0 41 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 43 54 1 0 54 55 1 0 33 56 1 0 56 57 1 0 56 58 1 0 56 59 1 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 1 25 64 1 0 64 65 1 0 65 2 1 0 64 6 1 0 19 10 1 0 62 23 1 0 62 28 1 0 59 29 1 0 54 35 1 0 52 45 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 10 76 1 1 12 77 1 1 13 78 1 0 13 79 1 0 14 80 1 0 15 81 1 1 16 82 1 0 17 83 1 1 18 84 1 0 19 85 1 6 20 86 1 0 21 87 1 0 21 88 1 0 22 89 1 0 22 90 1 0 24 91 1 0 24 92 1 0 24 93 1 0 26 94 1 0 27 95 1 0 27 96 1 0 28 97 1 6 30 98 1 0 30 99 1 0 30100 1 0 31101 1 0 31102 1 0 32103 1 0 32104 1 0 33105 1 6 35106 1 6 37107 1 6 40108 1 0 41109 1 1 42110 1 0 43111 1 6 45112 1 6 47113 1 0 47114 1 0 48115 1 1 49116 1 0 50117 1 6 51118 1 0 52119 1 1 53120 1 0 54121 1 1 55122 1 0 57123 1 0 57124 1 0 57125 1 0 58126 1 0 58127 1 0 58128 1 0 59129 1 6 60130 1 0 60131 1 0 61132 1 0 61133 1 0 63134 1 0 63135 1 0 63136 1 0 64137 1 1 65138 1 0 65139 1 0 M END

Standard InCHIKey	BAJBCZHVQXVBMJ-BJEVZSKZSA-N
Standard InCHI	InChI=1S/C47H74O18/c1-42(2)14-16-47(41(59)65-39-32(54)30(52)29(51)24(19-48)61-39)17-15-45(6)21(22(47)18-42)8-9-26-44(5)12-11-27(43(3,4)25(44)10-13-46(26,45)7)62-40-34(56)35(33(55)36(64-40)37(57)58)63-38-31(53)28(50)23(49)20-60-38/h8,22-36,38-40,48-56H,9-20H2,1-7H3,(H,57,58)/t22-,23+,24+,25-,26+,27-,28-,29+,30-,31+,32+,33-,34+,35-,36-,38-,39-,40+,44-,45+,46+,47-/m0/s1
SMILES	CC1(C)CC[C@]2(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	926.49	Volume:	903.331 ? Van der Waals volume.
Dense:	1.026	LogP:	1.591 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.401 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.97 ? 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:	0.092	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.259	Fsp³:	0.915
MCE-18:	175.0 ? 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:	0.895	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.008 ? 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:	0.174	Promiscuous compounds:	0.15

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.173	MDCK Permeability:	-5.091
Pgp-inhibitor:	0.0	Pgp-substrate:	0.021
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):	0.025
20% Bioavailability (F20%):	0.049	30% Bioavailability (F30%):	0.765
50% Bioavailability (F50%):	0.977

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.448
Plasma Protein Binding (PPB):	66.986%	Volume Distribution (VD):	-0.503
Fu:	23.347% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.994	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.021
HLM stability:	0.106 ? 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):

-0.097

Half-life (T1/2):

3.811

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.694	Drug-induced Liver Injury (DILI):	0.924
AMES Toxicity:	0.789	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	1.0
Carcinogencity:	0.04	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.422	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.402	RPMI-8226 Immunitoxicity:	0.084
A549 Cytotoxicity:	0.129	Hek293 Cytotoxicity:	0.077
BCF:	0.62 ? 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:	3.508 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.133 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.213 ? 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
NPO19870	Momordica cochinchinensis	Species	Cucurbitaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19711988]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19870	Momordica cochinchinensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54796	Basella rubra L.	Genus	Basellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19870	Momordica cochinchinensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19870	Momordica cochinchinensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19870	Momordica cochinchinensis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12301	Chenopodium quinoa	Species	Chenopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19870	Momordica cochinchinensis	Species	Cucurbitaceae	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 NPC514132 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	21013
0.1-0.2	24521
0.2-0.3	3037
0.3-0.4	687
0.4-0.5	351
0.5-0.6	108
0.6-0.7	68
0.7-0.8	0
0.8-0.85	4
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9158	High Similarity	NPC159309
0.9158	High Similarity	NPC86222
0.8788	High Similarity	NPC114484
0.8447	Intermediate Similarity	NPC11242
0.8173	Intermediate Similarity	NPC187290
0.8155	Intermediate Similarity	NPC301449
0.8155	Intermediate Similarity	NPC601290
0.798	Intermediate Similarity	NPC157868
0.7679	Intermediate Similarity	NPC4749
0.76	Intermediate Similarity	NPC475516
0.7596	Intermediate Similarity	NPC475591
0.7596	Intermediate Similarity	NPC236870
0.75	Intermediate Similarity	NPC251768
0.7383	Intermediate Similarity	NPC281148
0.7379	Intermediate Similarity	NPC469946
0.7374	Intermediate Similarity	NPC90856
0.7339	Intermediate Similarity	NPC481078
0.7333	Intermediate Similarity	NPC40775
0.7308	Intermediate Similarity	NPC192791
0.7282	Intermediate Similarity	NPC473884
0.7155	Intermediate Similarity	NPC21691
0.7143	Intermediate Similarity	NPC242840
0.7059	Intermediate Similarity	NPC48499
0.7037	Intermediate Similarity	NPC297263
0.6981	Remote Similarity	NPC223301
0.6981	Remote Similarity	NPC171544
0.6957	Remote Similarity	NPC123199
0.6952	Remote Similarity	NPC295371
0.6923	Remote Similarity	NPC481080
0.6863	Remote Similarity	NPC214484
0.6792	Remote Similarity	NPC6377
0.6792	Remote Similarity	NPC208381
0.6762	Remote Similarity	NPC235405
0.6757	Remote Similarity	NPC104372
0.6733	Remote Similarity	NPC128925
0.6726	Remote Similarity	NPC31838
0.6721	Remote Similarity	NPC302543
0.6699	Remote Similarity	NPC204458
0.6698	Remote Similarity	NPC249848
0.6698	Remote Similarity	NPC107966
0.6696	Remote Similarity	NPC481079
0.6667	Remote Similarity	NPC75417
0.6667	Remote Similarity	NPC112352
0.6638	Remote Similarity	NPC79643
0.6636	Remote Similarity	NPC63159
0.6636	Remote Similarity	NPC39211
0.661	Remote Similarity	NPC283417
0.661	Remote Similarity	NPC470218
0.661	Remote Similarity	NPC200049
0.6606	Remote Similarity	NPC30735
0.6555	Remote Similarity	NPC488560
0.6504	Remote Similarity	NPC481081
0.6491	Remote Similarity	NPC295823
0.6491	Remote Similarity	NPC174720
0.6491	Remote Similarity	NPC475467
0.6486	Remote Similarity	NPC235438
0.6476	Remote Similarity	NPC1046
0.6476	Remote Similarity	NPC78046
0.6475	Remote Similarity	NPC258617
0.6471	Remote Similarity	NPC475160
0.6471	Remote Similarity	NPC473714
0.6462	Remote Similarity	NPC475368
0.6435	Remote Similarity	NPC477194
0.6372	Remote Similarity	NPC64715
0.6348	Remote Similarity	NPC477193
0.6346	Remote Similarity	NPC209894
0.6333	Remote Similarity	NPC191827
0.6299	Remote Similarity	NPC250247
0.625	Remote Similarity	NPC11551
0.625	Remote Similarity	NPC46665
0.6239	Remote Similarity	NPC58448
0.621	Remote Similarity	NPC41061
0.621	Remote Similarity	NPC227551
0.6207	Remote Similarity	NPC480473
0.6207	Remote Similarity	NPC480474
0.62	Remote Similarity	NPC167383
0.6179	Remote Similarity	NPC476068
0.6142	Remote Similarity	NPC70809
0.614	Remote Similarity	NPC31193
0.614	Remote Similarity	NPC222580
0.6111	Remote Similarity	NPC236638
0.6111	Remote Similarity	NPC294453
0.6111	Remote Similarity	NPC305981
0.6106	Remote Similarity	NPC10607
0.6095	Remote Similarity	NPC256798
0.6078	Remote Similarity	NPC237503
0.6075	Remote Similarity	NPC189884
0.6075	Remote Similarity	NPC138334
0.6063	Remote Similarity	NPC261506
0.6063	Remote Similarity	NPC4328
0.6	Remote Similarity	NPC475287
0.6	Remote Similarity	NPC609763
0.5984	Remote Similarity	NPC135904
0.5982	Remote Similarity	NPC263756
0.5982	Remote Similarity	NPC213674
0.5982	Remote Similarity	NPC475171
0.5965	Remote Similarity	NPC480475
0.5946	Remote Similarity	NPC114441
0.5946	Remote Similarity	NPC150400
0.5932	Remote Similarity	NPC241909
0.5932	Remote Similarity	NPC80986
0.5932	Remote Similarity	NPC477192
0.592	Remote Similarity	NPC57484
0.5906	Remote Similarity	NPC43550
0.5872	Remote Similarity	NPC29069
0.5862	Remote Similarity	NPC475504
0.5856	Remote Similarity	NPC139894
0.5847	Remote Similarity	NPC477191
0.5833	Remote Similarity	NPC480936
0.5826	Remote Similarity	NPC44716
0.5826	Remote Similarity	NPC473459
0.5804	Remote Similarity	NPC173583
0.5785	Remote Similarity	NPC477196
0.5738	Remote Similarity	NPC60557
0.5738	Remote Similarity	NPC67857
0.5714	Remote Similarity	NPC85154
0.5702	Remote Similarity	NPC477195
0.5688	Remote Similarity	NPC161434
0.5664	Remote Similarity	NPC473373
0.5625	Remote Similarity	NPC265841
0.562	Remote Similarity	NPC104137
0.562	Remote Similarity	NPC26626
0.5615	Remote Similarity	NPC202828
0.5615	Remote Similarity	NPC119592
0.5606	Remote Similarity	NPC224381
0.5596	Remote Similarity	NPC480937
0.5574	Remote Similarity	NPC75287
0.5573	Remote Similarity	NPC298034
0.5573	Remote Similarity	NPC71065
0.5566	Remote Similarity	NPC283849
0.5565	Remote Similarity	NPC123522
0.5556	Remote Similarity	NPC164389
0.5556	Remote Similarity	NPC480422
0.5556	Remote Similarity	NPC602995
0.5546	Remote Similarity	NPC302887
0.5538	Remote Similarity	NPC293330
0.5537	Remote Similarity	NPC160452
0.5478	Remote Similarity	NPC488561
0.5476	Remote Similarity	NPC166422
0.5476	Remote Similarity	NPC470476
0.547	Remote Similarity	NPC160415
0.547	Remote Similarity	NPC117714
0.547	Remote Similarity	NPC30289
0.5447	Remote Similarity	NPC477197
0.5433	Remote Similarity	NPC471550
0.5431	Remote Similarity	NPC22956
0.5424	Remote Similarity	NPC180550
0.5424	Remote Similarity	NPC35405
0.5421	Remote Similarity	NPC606107
0.542	Remote Similarity	NPC65105
0.5417	Remote Similarity	NPC79718
0.5413	Remote Similarity	NPC242611
0.5403	Remote Similarity	NPC470475
0.5397	Remote Similarity	NPC475899
0.5385	Remote Similarity	NPC488308
0.5385	Remote Similarity	NPC286457
0.5379	Remote Similarity	NPC136768
0.5378	Remote Similarity	NPC258885
0.536	Remote Similarity	NPC300419
0.5357	Remote Similarity	NPC473481
0.5351	Remote Similarity	NPC603870
0.5349	Remote Similarity	NPC71391
0.5345	Remote Similarity	NPC472949
0.5344	Remote Similarity	NPC271610
0.5344	Remote Similarity	NPC312650
0.5328	Remote Similarity	NPC324875
0.5328	Remote Similarity	NPC292677
0.5315	Remote Similarity	NPC472268
0.5285	Remote Similarity	NPC187618
0.5278	Remote Similarity	NPC306746
0.5278	Remote Similarity	NPC199457
0.5276	Remote Similarity	NPC471384
0.5271	Remote Similarity	NPC47995
0.5267	Remote Similarity	NPC473645
0.5267	Remote Similarity	NPC110633
0.5263	Remote Similarity	NPC179434
0.5259	Remote Similarity	NPC127056
0.5259	Remote Similarity	NPC220160
0.525	Remote Similarity	NPC148417
0.5246	Remote Similarity	NPC247315
0.5246	Remote Similarity	NPC482728
0.5245	Remote Similarity	NPC297950
0.5238	Remote Similarity	NPC76972
0.5238	Remote Similarity	NPC469782
0.5238	Remote Similarity	NPC204414
0.5229	Remote Similarity	NPC68419
0.5227	Remote Similarity	NPC475514
0.521	Remote Similarity	NPC309714
0.521	Remote Similarity	NPC605226
0.5207	Remote Similarity	NPC481082
0.5207	Remote Similarity	NPC164419
0.5197	Remote Similarity	NPC192600
0.5194	Remote Similarity	NPC100639
0.5191	Remote Similarity	NPC484061
0.5191	Remote Similarity	NPC484062
0.5182	Remote Similarity	NPC31839
0.518	Remote Similarity	NPC33012
0.5172	Remote Similarity	NPC108748
0.5169	Remote Similarity	NPC161674
0.5167	Remote Similarity	NPC488526

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC514132 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6472
0.1-0.2	2615
0.2-0.3	59
0.3-0.4	2
0.4-0.5	1
0.5-0.6	1
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
0.5714	Remote Similarity	NPD8295	Clinical (unspecified phase)

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