NPASS Compound

Natural Product: NPC124296

Natural Product ID	NPC124296
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(1S,2R,4As,6Ar,6Ar,6Br,8Ar,10S,12Ar,14Bs)-10-[(2R,3R,4S,5S,6R)-3,5-Dihydroxy-6-Methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxyoxan-2-Yl]Oxy-1,2,6B,9,9,12A-Hexamethyl-4A-[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxycarbonyl-2,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydro-1H-Picene-6A-Carboxylic Acid
IUPAC Name	(1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-1,2,6b,9,9,12a-hexamethyl-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-6a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL448499
PubChem CID	44593499
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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 143150 0 0 0 0 0 0 0 0999 V2000 -14.3094 0.0646 -1.2436 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9923 0.0984 -1.6569 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.0562 0.6991 -0.6397 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.7663 0.6653 -1.2079 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8023 0.6998 -0.1816 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5599 0.6028 -0.5309 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5984 -0.2366 -0.4644 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3037 0.2456 0.2111 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6549 0.9790 1.3476 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5135 -0.9538 0.5676 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.8056 -2.1084 -0.1019 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2616 -2.0429 -1.3694 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0684 -0.8581 -1.7521 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2227 0.0782 -2.3419 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0687 -2.1254 -2.3062 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1560 -0.7902 0.5896 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4447 -0.8911 1.7060 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4526 -2.0280 1.5800 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5601 -1.8904 0.3787 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9567 -0.4860 0.2357 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.1960 0.2386 1.5239 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5793 0.3254 2.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3171 1.6094 1.7423 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4916 0.3196 3.5792 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4997 1.5838 1.4627 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9858 1.2942 1.5287 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3994 0.4561 0.3288 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5505 -0.7131 0.1322 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9135 -1.4915 -1.0992 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3806 -1.5830 -1.2403 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2672 -0.9332 -0.4886 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8317 -0.0255 0.5940 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7893 1.1301 0.6009 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1555 0.6318 0.9665 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6571 -0.5295 0.1890 C 0 0 2 0 0 0 0 0 0 0 0 0 4.7410 -1.1599 -0.7761 C 0 0 1 0 0 0 0 0 0 0 0 0 4.9271 -2.5894 -1.0943 C 0 0 1 0 0 0 0 0 0 0 0 0 5.0250 -2.7515 -2.6254 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0732 -3.3265 -0.5405 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5769 -4.4928 0.3324 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9855 -2.5281 0.3519 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1617 -1.5611 1.1809 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8942 -0.0221 -0.5469 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0323 -0.1208 -1.7802 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9182 0.5779 0.1683 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0570 1.0395 -0.5298 C 0 0 2 0 0 0 0 0 0 0 0 0 10.2333 0.5410 -0.0453 O 0 0 0 0 0 0 0 0 0 0 0 0 11.2820 0.9902 -0.8323 C 0 0 2 0 0 0 0 0 0 0 0 0 12.5917 0.3138 -0.4556 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9184 0.5798 0.8746 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5264 2.4769 -0.7009 C 0 0 2 0 0 0 0 0 0 0 0 0 10.3937 3.0993 0.0500 C 0 0 1 0 0 0 0 0 0 0 0 0 9.0586 2.5664 -0.3513 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5905 3.1036 -1.5517 O 0 0 0 0 0 0 0 0 0 0 0 0 10.5776 2.8410 1.4221 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6982 3.0525 -1.9616 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9220 -0.7460 1.8790 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4012 -0.2011 2.9384 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5141 -2.0660 2.0871 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4419 1.4462 -0.8116 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5570 0.1321 -0.9705 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1988 1.8487 0.7182 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.0492 2.8422 -0.0777 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.3908 2.1549 -0.3778 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.2145 2.3405 0.7032 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4617 3.0458 -1.3228 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.9674 1.4407 1.8036 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.5148 0.8937 -0.7582 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6143 -0.9385 -1.9007 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9546 0.6415 -2.6262 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0925 0.1280 0.2966 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0882 -0.2367 0.4049 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9012 -1.1577 0.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8360 0.9018 -0.5472 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5779 0.4024 2.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7844 -1.1702 1.6291 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8434 -2.9799 -1.5722 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8965 -1.1822 -2.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6912 0.6354 -3.0149 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3359 -2.8998 -1.9806 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3546 -2.4124 -3.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4950 -1.1569 -2.3003 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0687 -1.1522 2.6087 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0058 -2.9742 1.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8001 -1.9977 2.4759 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1396 -2.1802 -0.5224 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7794 -2.6750 0.5037 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5915 -0.3533 2.2837 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1183 1.7183 2.5174 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6504 2.4800 1.8865 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7235 1.6535 0.7192 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7520 1.0421 3.9276 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5048 0.5814 3.9951 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2919 -0.7010 3.9564 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7120 2.1958 2.3910 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8023 2.1704 0.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1709 0.7780 2.4802 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5327 2.2426 1.5040 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7306 -1.4297 0.9820 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4234 -1.1635 -2.0290 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5675 -2.5592 -0.9736 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7292 -2.2346 -2.0305 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5362 1.9405 1.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9399 1.5572 -0.4329 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3166 0.4923 2.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8252 1.5515 0.7852 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8690 -0.5537 -1.7398 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9981 -3.1809 -0.8297 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7980 -1.7969 -3.1457 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4473 -3.6142 -2.9879 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0907 -2.9726 -2.9235 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6969 -3.8191 -1.3143 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4429 -5.0059 0.7507 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9766 -4.0739 1.1812 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8807 -5.1372 -0.2413 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6869 -1.9227 -0.2568 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5982 -3.1558 1.0252 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3806 -2.1401 1.6675 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8582 -1.1151 1.9252 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9856 0.8115 -1.6235 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0637 0.7401 -1.8818 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3851 0.7738 -1.0638 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5510 -0.7522 -0.6950 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1292 0.5935 1.4529 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4731 2.6983 -0.1223 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3503 4.2064 -0.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3172 2.8856 0.4310 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1795 2.8140 -2.3168 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0038 3.6299 1.8609 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0278 3.9885 -1.8894 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6008 -2.5205 2.9986 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1233 2.2968 -0.4973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4786 1.9897 -0.9421 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8613 1.0543 -1.7300 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8756 0.2953 -1.8318 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3529 -0.5255 -1.4445 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9874 1.1497 -0.7932 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3180 2.3962 1.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1918 3.7618 0.4869 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8026 2.6131 -1.2815 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2763 1.5289 1.2458 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8684 3.8263 -1.3325 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4281 0.8780 2.4351 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 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 12 15 1 0 10 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 21 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 2 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 37 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 35 43 1 6 43 44 2 0 43 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 48 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 52 55 1 0 51 56 1 0 32 57 1 1 57 58 2 0 57 59 1 0 27 60 1 6 20 61 1 6 5 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 63 66 1 0 62 67 1 0 64 3 1 0 13 7 1 0 22 17 1 0 32 27 1 0 42 35 1 0 53 46 1 0 28 20 1 0 36 31 1 0 1 68 1 0 2 69 1 0 2 70 1 0 3 71 1 1 5 72 1 1 7 73 1 1 8 74 1 6 9 75 1 0 10 76 1 1 12 77 1 6 13 78 1 6 14 79 1 0 15 80 1 0 15 81 1 0 15 82 1 0 17 83 1 1 18 84 1 0 18 85 1 0 19 86 1 0 19 87 1 0 21 88 1 1 23 89 1 0 23 90 1 0 23 91 1 0 24 92 1 0 24 93 1 0 24 94 1 0 25 95 1 0 25 96 1 0 26 97 1 0 26 98 1 0 28 99 1 1 29100 1 0 29101 1 0 30102 1 0 33103 1 0 33104 1 0 34105 1 0 34106 1 0 36107 1 6 37108 1 1 38109 1 0 38110 1 0 38111 1 0 39112 1 6 40113 1 0 40114 1 0 40115 1 0 41116 1 0 41117 1 0 42118 1 0 42119 1 0 46120 1 6 48121 1 6 49122 1 0 49123 1 0 50124 1 0 51125 1 1 52126 1 1 53127 1 1 54128 1 0 55129 1 0 56130 1 0 59131 1 0 60132 1 0 60133 1 0 60134 1 0 61135 1 0 61136 1 0 61137 1 0 62138 1 1 63139 1 1 64140 1 6 65141 1 0 66142 1 0 67143 1 0 M END

Standard InCHIKey	AYUPCUGXBHAUAL-NCYGRLIXSA-N
Standard InCHI	InChI=1S/C48H76O19/c1-20-10-15-47(43(61)67-40-36(57)34(55)32(53)25(19-50)64-40)16-17-48(42(59)60)23(29(47)21(20)2)8-9-27-45(6)13-12-28(44(4,5)26(45)11-14-46(27,48)7)65-41-37(58)38(30(51)22(3)62-41)66-39-35(56)33(54)31(52)24(18-49)63-39/h8,20-22,24-41,49-58H,9-19H2,1-7H3,(H,59,60)/t20-,21+,22-,24-,25-,26+,27-,28+,29+,30+,31-,32-,33+,34+,35-,36-,37-,38+,39+,40+,41+,45+,46-,47+,48-/m1/s1
SMILES	OC[C@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@@H](O[C@@H]([C@@H]2O)C)O[C@H]2CC[C@]3([C@H](C2(C)C)CC[C@@]2([C@@H]3CC=C3[C@]2(CC[C@@]2([C@H]3[C@@H](C)[C@H](C)CC2)C(=O)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)C(=O)O)C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	956.5	Volume:	929.417 ? Van der Waals volume.
Dense:	1.029	LogP:	0.565 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.878 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.211 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	46.0
TPSA:	312.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	8.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.083	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.409	Fsp³:	0.917
MCE-18:	173.935 ? 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:	0.772	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.031 ? 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:	0.174	Promiscuous compounds:	0.233

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.332	MDCK Permeability:	-4.993
Pgp-inhibitor:	0.0	Pgp-substrate:	0.185
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):	0.907
20% Bioavailability (F20%):	0.256	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.301
Plasma Protein Binding (PPB):	61.646%	Volume Distribution (VD):	-0.519
Fu:	31.748% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.719	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.007
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):

-0.098

Half-life (T1/2):

3.616

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.001
Human Hepatotoxicity (H-HT):	0.826	Drug-induced Liver Injury (DILI):	0.991
AMES Toxicity:	0.988	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.001	Skin Sensitization:	1.0
Carcinogencity:	0.216	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.808	Drug-induced Nephrotoxicity:	0.996
Genotoxicity:	0.856	RPMI-8226 Immunitoxicity:	0.089
A549 Cytotoxicity:	0.724	Hek293 Cytotoxicity:	0.266
BCF:	0.587 ? 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:	3.287 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.67 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.758 ? 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
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1919590]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2553871]
NPO25311	Guettarda platypoda	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26547	Uncaria tomentosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25311	Guettarda platypoda	Species	Rubiaceae	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
MIC50	1

Activity Type	# Activity
Organism	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
NPT2516	Organism	Vesicular stomatitis Indiana virus	Vesicular stomatitis Indiana virus	MIC50	=	42000.0	nM	PubChem BioAssay data set

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 NPC124296 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	18407
0.1-0.2	26450
0.2-0.3	3799
0.3-0.4	953
0.4-0.5	213
0.5-0.6	28
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8966	High Similarity	NPC30397
0.8764	High Similarity	NPC235841
0.8764	High Similarity	NPC297208
0.7527	Intermediate Similarity	NPC607754
0.7474	Intermediate Similarity	NPC211798
0.6923	Remote Similarity	NPC258885
0.6526	Remote Similarity	NPC274507
0.5943	Remote Similarity	NPC108748
0.5865	Remote Similarity	NPC473481
0.5431	Remote Similarity	NPC114484
0.5385	Remote Similarity	NPC324875
0.5385	Remote Similarity	NPC292677
0.5351	Remote Similarity	NPC159309
0.5351	Remote Similarity	NPC180550
0.5351	Remote Similarity	NPC35405
0.5351	Remote Similarity	NPC86222
0.5319	Remote Similarity	NPC60755
0.5319	Remote Similarity	NPC77099
0.531	Remote Similarity	NPC223301
0.531	Remote Similarity	NPC171544
0.5294	Remote Similarity	NPC475486
0.5221	Remote Similarity	NPC475171
0.5203	Remote Similarity	NPC471384
0.5167	Remote Similarity	NPC481078
0.5161	Remote Similarity	NPC166422
0.5128	Remote Similarity	NPC275668
0.5122	Remote Similarity	NPC79643
0.5089	Remote Similarity	NPC475516
0.5079	Remote Similarity	NPC54636
0.5049	Remote Similarity	NPC484195
0.5044	Remote Similarity	NPC58448
0.5042	Remote Similarity	NPC104372
0.504	Remote Similarity	NPC219180
0.504	Remote Similarity	NPC251263
0.5039	Remote Similarity	NPC481080

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC124296 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5935
0.1-0.2	3133
0.2-0.3	73
0.3-0.4	9
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