NPASS Compound

Natural Product: NPC549847

Natural Product ID	NPC549847
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-7-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-7-yl]oxy-2-(4-hydroxyphenyl)-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-7-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3-[(2~{S},3~{R},4~{S},5~{R},6~{R})-3,4,5-trihydroxy-6-[[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-7-yl]oxy-2-(4-hydroxyphenyl)-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
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 141150 0 0 0 0 0 0 0 0999 V2000 12.5502 4.4094 1.5591 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6035 3.5761 0.9080 C 0 0 2 0 0 0 0 0 0 0 0 0 13.1434 2.5772 0.0916 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5396 1.5264 0.8184 C 0 0 1 0 0 0 0 0 0 0 0 0 11.9856 0.6686 -0.1264 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6114 0.6474 -0.0395 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0437 0.0726 1.2260 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6775 0.0739 1.2834 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9990 -0.8011 0.4884 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2185 -0.1319 -0.5012 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9663 -0.5866 -0.8612 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7461 -1.2780 -2.0091 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7604 -1.6108 -3.0304 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5005 -2.5997 -3.9544 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3996 -2.8366 -4.9675 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5629 -2.1035 -5.0818 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4681 -2.3656 -6.1300 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8356 -1.1168 -4.1707 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9065 -0.8924 -3.1487 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5021 -1.6946 -2.2484 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5063 -1.4611 -1.4380 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2409 -1.9301 -1.7711 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1568 -1.6875 -0.9171 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0278 -2.1829 -1.3370 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2215 -2.1203 -0.7178 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6615 -3.1463 0.0872 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8942 -3.0756 0.7120 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3301 -4.1156 1.5204 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7232 -1.9857 0.5551 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9673 -1.8865 1.1571 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3709 -2.8074 1.8828 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7838 -0.7633 0.9668 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0263 -0.6846 1.5632 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1708 -1.2925 0.9297 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9218 -0.4669 0.1750 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2522 -0.3292 0.3109 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.6370 0.8396 1.2310 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9974 0.9634 1.2422 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.5851 1.3724 0.0591 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.4254 0.3823 -0.4171 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.8171 0.8392 -1.6995 C 0 0 1 0 0 0 0 0 0 0 0 0 -14.4084 -0.3049 -2.4791 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.8766 1.8721 -1.4699 C 0 0 2 0 0 0 0 0 0 0 0 0 -15.0084 2.6712 -2.6345 O 0 0 0 0 0 0 0 0 0 0 0 0 -14.6656 2.7422 -0.2722 C 0 0 1 0 0 0 0 0 0 0 0 0 -15.6517 2.4013 0.6726 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.3224 2.6545 0.3630 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.4583 2.8234 1.7447 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.0454 -1.5559 0.7012 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.9759 -1.1906 1.7153 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1988 -2.6819 1.2286 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.9232 -3.3433 2.2079 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9462 -2.1250 1.9029 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.2733 -3.2129 2.4137 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2779 0.2146 0.1670 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9628 1.4665 -0.1456 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0218 1.9598 0.5278 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6458 3.1535 0.1666 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2004 3.8828 -0.9028 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8193 5.0909 -1.2802 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1265 3.3856 -1.5903 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5099 2.2102 -1.2368 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0661 0.0666 -0.3961 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2909 -0.9574 -0.2445 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0387 -1.0257 -0.8802 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3341 -0.9857 0.2581 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5865 -0.5199 0.5913 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7961 0.1881 1.7665 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6670 -0.7616 -0.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9286 -0.3132 0.0323 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0951 0.3186 1.0833 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7186 -2.0092 0.0156 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8480 -3.1293 -0.0669 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8841 -2.4286 0.8927 C 0 0 1 0 0 0 0 0 0 0 0 0 10.7793 -3.2346 0.1535 O 0 0 0 0 0 0 0 0 0 0 0 0 10.6229 -1.3020 1.5298 C 0 0 2 0 0 0 0 0 0 0 0 0 10.6793 -1.4936 2.9234 O 0 0 0 0 0 0 0 0 0 0 0 0 13.5388 0.8614 1.7246 C 0 0 2 0 0 0 0 0 0 0 0 0 13.1322 0.9478 3.0799 O 0 0 0 0 0 0 0 0 0 0 0 0 14.8698 1.6149 1.6376 C 0 0 2 0 0 0 0 0 0 0 0 0 15.7035 1.0813 2.6224 O 0 0 0 0 0 0 0 0 0 0 0 0 14.5836 3.0650 1.9510 C 0 0 1 0 0 0 0 0 0 0 0 0 15.7841 3.8012 1.9131 O 0 0 0 0 0 0 0 0 0 0 0 0 12.8311 5.4795 1.4716 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5892 4.2551 1.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 12.4520 4.2307 2.6529 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2086 4.2609 0.2374 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7877 2.0380 1.4567 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3075 1.7443 -0.1371 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1996 0.1849 -0.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3873 0.7270 2.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1682 -1.2493 1.1668 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5794 -3.1612 -3.8372 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2035 -3.6142 -5.7023 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7447 -1.5629 -6.6955 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7454 -0.5262 -4.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1935 -0.0859 -2.4780 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1108 -2.4866 -2.7021 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0297 -4.0365 0.2431 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6821 -4.5661 2.1480 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7081 -2.0274 0.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6546 -0.0456 -0.7045 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1134 1.7279 0.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3113 0.6234 2.2658 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7843 1.5529 -0.6809 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.9333 1.2231 -2.2550 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.2237 0.1361 -3.1225 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.6730 -0.7382 -3.2032 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.8467 -1.0951 -1.8312 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.8491 1.3178 -1.4008 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.2667 3.3273 -2.6951 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9073 3.7946 -0.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.6067 2.9088 1.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.6882 3.4891 0.0005 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7671 2.3895 2.2724 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6552 -1.9605 -0.1301 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8196 -1.7372 1.6309 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8909 -3.3934 0.4692 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3329 -3.8787 2.8074 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2833 -1.4931 2.7460 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4338 -3.3710 3.3720 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4224 1.4422 1.4155 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4820 3.4643 0.7711 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3532 5.0962 -2.1290 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7515 3.9487 -2.4540 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6535 1.8244 -1.7973 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7556 -0.1798 -1.5021 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4898 -0.8071 0.9083 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0523 0.8282 2.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0961 -1.8685 -1.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3282 -3.9672 0.0939 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4739 -3.0863 1.6893 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2519 -3.8568 -0.3950 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6536 -1.3237 1.1719 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5781 -2.4789 3.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7061 -0.2040 1.4388 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6020 1.8024 3.1940 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2314 1.4695 0.6171 H 0 0 0 0 0 0 0 0 0 0 0 0 16.0013 0.1780 2.2895 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1164 3.1493 2.9510 H 0 0 0 0 0 0 0 0 0 0 0 0 15.8411 4.2942 1.0366 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 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 2 0 12 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 1 0 27 29 2 0 29 30 1 0 30 31 2 0 30 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 41 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 36 49 1 0 49 50 1 0 49 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 32 55 2 0 55 56 1 0 56 57 2 0 57 58 1 0 58 59 2 0 59 60 1 0 59 61 1 0 61 62 2 0 55 63 1 0 63 64 1 0 64 65 2 0 23 66 2 0 66 67 1 0 67 68 1 0 67 69 2 0 69 70 1 0 70 71 2 0 9 72 1 0 72 73 1 0 72 74 1 0 74 75 1 0 74 76 1 0 76 77 1 0 4 78 1 0 78 79 1 0 78 80 1 0 80 81 1 0 80 82 1 0 82 83 1 0 82 2 1 0 76 7 1 0 70 11 1 0 19 13 1 0 69 21 1 0 65 25 1 0 64 29 1 0 53 34 1 0 62 56 1 0 47 39 1 0 1 84 1 0 1 85 1 0 1 86 1 0 2 87 1 6 4 88 1 1 6 89 1 0 6 90 1 0 7 91 1 1 9 92 1 1 14 93 1 0 15 94 1 0 17 95 1 0 18 96 1 0 19 97 1 0 22 98 1 0 26 99 1 0 28100 1 0 34101 1 6 36102 1 6 37103 1 0 37104 1 0 39105 1 6 41106 1 6 42107 1 0 42108 1 0 42109 1 0 43110 1 1 44111 1 0 45112 1 6 46113 1 0 47114 1 6 48115 1 0 49116 1 6 50117 1 0 51118 1 6 52119 1 0 53120 1 1 54121 1 0 57122 1 0 58123 1 0 60124 1 0 61125 1 0 62126 1 0 65127 1 0 66128 1 0 68129 1 0 72130 1 6 73131 1 0 74132 1 1 75133 1 0 76134 1 6 77135 1 0 78136 1 6 79137 1 0 80138 1 6 81139 1 0 82140 1 1 83141 1 0 M END

Standard InCHIKey	IDEAHSWPVAPDEN-ACACJXAFSA-N
Standard InCHI	InChI=1S/C54H58O29/c1-17-33(59)39(65)43(69)51(75-17)73-15-29-35(61)41(67)45(71)53(80-29)82-49-37(63)31-25(57)11-23(13-27(31)78-47(49)19-3-7-21(55)8-4-19)77-24-12-26(58)32-28(14-24)79-48(20-5-9-22(56)10-6-20)50(38(32)64)83-54-46(72)42(68)36(62)30(81-54)16-74-52-44(70)40(66)34(60)18(2)76-52/h3-14,17-18,29-30,33-36,39-46,51-62,65-72H,15-16H2,1-2H3/t17-,18-,29+,30+,33-,34-,35-,36+,39+,40+,41-,42-,43+,44+,45+,46+,51-,52+,53-,54-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(C4=CC=C(O)C=C4)OC4=CC(OC5=CC(O)=C6C(=O)C(O[C@@H]7O[C@H](CO[C@H]8O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H](O)[C@H]7O)=C(C7=CC=C(O)C=C7)OC6=C5)=CC(O)=C4C3=O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1170.31	Volume:	1069.708 ? Van der Waals volume.
Dense:	1.094	LogP:	1.132 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.219 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.942 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	14.0	Rigid Bonds:	60.0
TPSA:	467.17 ? Topological Polar Surface Area.	H-Bond Acceptor:	29.0
H-Bond Donor:	16.0	Rings:	10.0
Heavy Atoms:	29.0

MedChem Properties

QED Drug-Likeness Score:	0.056	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.331	Fsp³:	0.444
MCE-18:	238.872 ? 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:	0.675	Fluc inhibitor:	0.234 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.741 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.665 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.321	Promiscuous compounds:	0.625

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.906	MDCK Permeability:	-4.689
Pgp-inhibitor:	0.0	Pgp-substrate:	0.997
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):	0.05
20% Bioavailability (F20%):	0.053	30% Bioavailability (F30%):	0.998
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.002
Plasma Protein Binding (PPB):	81.835%	Volume Distribution (VD):	0.164
Fu:	13.503% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.392
BSEP inhibitor:	0.183

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:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.31
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.18 ? 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):

-0.259

Half-life (T1/2):

7.49

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.134
Human Hepatotoxicity (H-HT):	0.526	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.95	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.085	Skin Sensitization:	0.999
Carcinogencity:	0.005	Eye Corrosion:	0.0
Eye Irritation:	0.013	Respiratory Toxicity:	0.001
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.993
Hematotoxicity:	0.02	Drug-induced Nephrotoxicity:	0.637
Genotoxicity:	0.993	RPMI-8226 Immunitoxicity:	0.337
A549 Cytotoxicity:	0.95	Hek293 Cytotoxicity:	0.977
BCF:	0.711 ? 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:	3.47 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.911 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.23 ? 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
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568781]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21341711]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21341711]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3893	Chimarrhis turbinata	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

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 NPC549847 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	21440
0.1-0.2	24855
0.2-0.3	2711
0.3-0.4	401
0.4-0.5	243
0.5-0.6	131
0.6-0.7	43
0.7-0.8	2
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8571	High Similarity	NPC186816
0.7907	Intermediate Similarity	NPC173582
0.7907	Intermediate Similarity	NPC265885
0.7907	Intermediate Similarity	NPC181465
0.7907	Intermediate Similarity	NPC215710
0.7907	Intermediate Similarity	NPC473438
0.7907	Intermediate Similarity	NPC253788
0.7416	Intermediate Similarity	NPC65563
0.7416	Intermediate Similarity	NPC470949
0.7333	Intermediate Similarity	NPC473571
0.7333	Intermediate Similarity	NPC110941
0.7222	Intermediate Similarity	NPC203259
0.7222	Intermediate Similarity	NPC33054
0.7222	Intermediate Similarity	NPC176740
0.7222	Intermediate Similarity	NPC471725
0.7222	Intermediate Similarity	NPC134532
0.7222	Intermediate Similarity	NPC602582
0.7059	Intermediate Similarity	NPC46420
0.7024	Intermediate Similarity	NPC249281
0.7021	Intermediate Similarity	NPC142142
0.6989	Remote Similarity	NPC470443
0.697	Remote Similarity	NPC25523
0.6923	Remote Similarity	NPC44931
0.6854	Remote Similarity	NPC276377
0.6813	Remote Similarity	NPC471079
0.6771	Remote Similarity	NPC476472
0.6771	Remote Similarity	NPC294815
0.6771	Remote Similarity	NPC473073
0.6771	Remote Similarity	NPC16194
0.6739	Remote Similarity	NPC39834
0.6702	Remote Similarity	NPC126784
0.6702	Remote Similarity	NPC241423
0.6562	Remote Similarity	NPC473327
0.6559	Remote Similarity	NPC67105
0.6556	Remote Similarity	NPC116458
0.6556	Remote Similarity	NPC246943
0.6489	Remote Similarity	NPC210073
0.6489	Remote Similarity	NPC150164
0.6458	Remote Similarity	NPC12013
0.6458	Remote Similarity	NPC11432
0.6458	Remote Similarity	NPC477613
0.6436	Remote Similarity	NPC189564
0.6392	Remote Similarity	NPC72016
0.6337	Remote Similarity	NPC203145
0.6322	Remote Similarity	NPC111929
0.6322	Remote Similarity	NPC320283
0.6322	Remote Similarity	NPC41121
0.6316	Remote Similarity	NPC156869
0.6311	Remote Similarity	NPC480441
0.6292	Remote Similarity	NPC271692
0.6224	Remote Similarity	NPC32641
0.6224	Remote Similarity	NPC256188
0.6211	Remote Similarity	NPC67326
0.62	Remote Similarity	NPC470449
0.62	Remote Similarity	NPC221342
0.62	Remote Similarity	NPC476470
0.618	Remote Similarity	NPC297987
0.6176	Remote Similarity	NPC121703
0.6146	Remote Similarity	NPC303913
0.6139	Remote Similarity	NPC602448
0.6061	Remote Similarity	NPC35119
0.6042	Remote Similarity	NPC227508
0.602	Remote Similarity	NPC240306
0.5979	Remote Similarity	NPC22062
0.5979	Remote Similarity	NPC473634
0.5979	Remote Similarity	NPC138811
0.5941	Remote Similarity	NPC470447
0.5905	Remote Similarity	NPC292019
0.5905	Remote Similarity	NPC202908
0.59	Remote Similarity	NPC122467
0.59	Remote Similarity	NPC209296
0.5895	Remote Similarity	NPC116864
0.5895	Remote Similarity	NPC244776
0.5859	Remote Similarity	NPC488073
0.5859	Remote Similarity	NPC488074
0.5851	Remote Similarity	NPC605784
0.5824	Remote Similarity	NPC158674
0.5784	Remote Similarity	NPC89127
0.5758	Remote Similarity	NPC129264
0.5728	Remote Similarity	NPC101636
0.5714	Remote Similarity	NPC127546
0.5714	Remote Similarity	NPC209550
0.5714	Remote Similarity	NPC57625
0.5714	Remote Similarity	NPC173637
0.5714	Remote Similarity	NPC317489
0.5714	Remote Similarity	NPC223424
0.5714	Remote Similarity	NPC600591
0.57	Remote Similarity	NPC470125
0.569	Remote Similarity	NPC483159
0.569	Remote Similarity	NPC483160
0.5673	Remote Similarity	NPC470446
0.5638	Remote Similarity	NPC611303
0.5631	Remote Similarity	NPC85751
0.5631	Remote Similarity	NPC19240
0.5625	Remote Similarity	NPC476215
0.5619	Remote Similarity	NPC470455
0.5619	Remote Similarity	NPC14187
0.5612	Remote Similarity	NPC187379
0.5591	Remote Similarity	NPC27640
0.5588	Remote Similarity	NPC270448
0.5566	Remote Similarity	NPC89052
0.5545	Remote Similarity	NPC64425
0.5545	Remote Similarity	NPC153755
0.5543	Remote Similarity	NPC77672
0.5543	Remote Similarity	NPC108831
0.5543	Remote Similarity	NPC133671
0.5543	Remote Similarity	NPC135391
0.5543	Remote Similarity	NPC78263
0.5543	Remote Similarity	NPC250069
0.5543	Remote Similarity	NPC182634
0.5536	Remote Similarity	NPC474522
0.5534	Remote Similarity	NPC486577
0.5484	Remote Similarity	NPC136042
0.5472	Remote Similarity	NPC214621
0.5472	Remote Similarity	NPC34267
0.5463	Remote Similarity	NPC173837
0.5446	Remote Similarity	NPC204693
0.5439	Remote Similarity	NPC241781
0.5435	Remote Similarity	NPC331652
0.5429	Remote Similarity	NPC292929
0.5429	Remote Similarity	NPC470445
0.5426	Remote Similarity	NPC24043
0.5413	Remote Similarity	NPC303694
0.54	Remote Similarity	NPC163242
0.54	Remote Similarity	NPC272068
0.5391	Remote Similarity	NPC192539
0.5376	Remote Similarity	NPC289667
0.5368	Remote Similarity	NPC59534
0.5364	Remote Similarity	NPC277532
0.5361	Remote Similarity	NPC223747
0.5354	Remote Similarity	NPC251417
0.5347	Remote Similarity	NPC479405
0.5347	Remote Similarity	NPC605592
0.5333	Remote Similarity	NPC471669
0.531	Remote Similarity	NPC480445
0.5306	Remote Similarity	NPC66087
0.5304	Remote Similarity	NPC138990
0.53	Remote Similarity	NPC139320
0.53	Remote Similarity	NPC609888
0.5294	Remote Similarity	NPC473554
0.5294	Remote Similarity	NPC479404
0.5283	Remote Similarity	NPC298171
0.5283	Remote Similarity	NPC36138
0.5275	Remote Similarity	NPC54802
0.5275	Remote Similarity	NPC197304
0.5269	Remote Similarity	NPC135599
0.5269	Remote Similarity	NPC73855
0.5269	Remote Similarity	NPC113968
0.5269	Remote Similarity	NPC328940
0.5269	Remote Similarity	NPC277174
0.5269	Remote Similarity	NPC606877
0.5263	Remote Similarity	NPC156785
0.5263	Remote Similarity	NPC305811
0.5263	Remote Similarity	NPC162394
0.5259	Remote Similarity	NPC175429
0.5253	Remote Similarity	NPC265115
0.5248	Remote Similarity	NPC275454
0.5243	Remote Similarity	NPC64051
0.5234	Remote Similarity	NPC223426
0.5234	Remote Similarity	NPC470450
0.5217	Remote Similarity	NPC288084
0.5213	Remote Similarity	NPC238376
0.5197	Remote Similarity	NPC482520
0.5197	Remote Similarity	NPC482519
0.5192	Remote Similarity	NPC65711
0.5158	Remote Similarity	NPC265530
0.5155	Remote Similarity	NPC159579
0.5155	Remote Similarity	NPC219904
0.5143	Remote Similarity	NPC37668
0.5143	Remote Similarity	NPC606657
0.5104	Remote Similarity	NPC84362
0.5104	Remote Similarity	NPC488080
0.5104	Remote Similarity	NPC169977
0.5102	Remote Similarity	NPC181616
0.51	Remote Similarity	NPC95866
0.51	Remote Similarity	NPC172807
0.51	Remote Similarity	NPC477848
0.5096	Remote Similarity	NPC296018
0.5094	Remote Similarity	NPC488089
0.5091	Remote Similarity	NPC470416
0.5088	Remote Similarity	NPC488734
0.5088	Remote Similarity	NPC488735
0.5088	Remote Similarity	NPC488739
0.5088	Remote Similarity	NPC488732
0.5088	Remote Similarity	NPC488738
0.5053	Remote Similarity	NPC476405
0.5053	Remote Similarity	NPC19709
0.5051	Remote Similarity	NPC99957
0.5049	Remote Similarity	NPC473512
0.5049	Remote Similarity	NPC129827
0.5048	Remote Similarity	NPC483414
0.5048	Remote Similarity	NPC483415
0.5046	Remote Similarity	NPC81042
0.5043	Remote Similarity	NPC298666

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC549847 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5494
0.1-0.2	3604
0.2-0.3	43
0.3-0.4	3
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
0.7-0.8	2
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
0.7312	Intermediate Similarity	NPD7251	Phase 2
0.7222	Intermediate Similarity	NPD6797	Phase 2
0.6667	Remote Similarity	NPD7808	Phase 3
0.59	Remote Similarity	NPD7054	Phase 4

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