NPASS Compound

Natural Product: NPC38295

Natural Product ID	NPC38295
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2S)-1,2-Di-O-Linolenoyl-3-O-Alpha-Galactopyranosyl-(1->6)-O-Beta-Galactopyranosyl Glycerol
IUPAC Name	[(2S)-2-[(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropyl] (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1951711
PubChem CID	57400365
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000175] Glycerolipids [CHEMONTID:0000637] Glycosylglycerols [CHEMONTID:0003344] 3-O-beta-D-digalactosyl-sn-glycerols

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

Chemical Representations

RDKit 2D 150151 0 0 0 0 0 0 0 0999 V2000 -14.2450 6.8829 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.2091 5.7338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -16.1733 4.5847 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.6603 3.1752 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.1831 2.9147 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7059 2.6543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1928 1.2447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.1570 0.0957 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.1212 -1.0534 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.6082 -2.4629 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1310 -2.7234 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6538 -2.9839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1765 -3.2444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6993 -3.5048 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2221 -3.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7449 -4.0258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2677 -4.2863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7905 -4.5467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2775 -5.9563 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8263 -3.3977 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6509 -3.6581 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1281 -3.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6053 -4.1791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1184 -5.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1542 -6.7377 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5956 -5.8491 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0728 -6.1096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5500 -6.3700 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0272 -6.6305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5044 -6.8910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.9816 -7.1514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4588 -7.4119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.9361 -7.6724 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.9002 -6.5233 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.3872 -5.1138 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.8742 -3.7042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.8384 -2.5552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 18.3156 -2.8157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.7928 -3.0761 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.7570 -1.9271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 20.2439 -0.5175 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 19.7309 0.8920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3886 -2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6491 -0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1595 -1.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5691 -2.3251 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7181 -1.3609 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5691 -0.3967 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8296 1.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3296 1.0805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8296 1.0805 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2391 1.5935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3882 0.6293 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1277 -0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6277 -0.8479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1382 1.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4891 2.8925 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 0.9642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.0959 5.9187 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.3940 7.8471 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.2808 8.0319 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.3582 6.6980 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9511 4.9169 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -17.6505 4.8452 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.6245 2.0261 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7445 4.3492 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6217 1.4803 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7417 3.8033 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7156 0.9843 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8990 -0.7213 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.4151 0.9126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.5984 -0.7929 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.5724 -3.6120 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6924 -1.2890 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3914 -4.2006 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9142 -4.4611 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3933 -1.5067 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7379 -1.8099 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4370 -4.7216 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4389 -2.0276 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9598 -4.9820 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9616 -2.2881 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4826 -5.2425 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4844 -2.5486 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0054 -5.5030 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5282 -5.7635 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3724 -2.7899 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3646 -2.1857 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3904 -5.1353 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8676 -5.3958 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3351 -7.3263 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8560 -4.3719 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3333 -4.6323 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8123 -7.5868 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2895 -7.8472 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8105 -4.8928 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2877 -5.1533 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7667 -8.1077 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7649 -5.4138 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2439 -8.3682 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7212 -8.6287 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2421 -5.6742 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5373 -5.9140 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.1984 -8.8891 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.4491 -9.0819 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.3775 -6.7838 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9256 -5.4512 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 17.8488 -4.7764 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3970 -3.4438 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 16.3253 -1.1456 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.3940 -1.3177 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.2371 -4.3136 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 20.3058 -4.4857 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 22.2342 -2.1875 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.6535 -0.0045 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.7824 -0.8549 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 21.1404 1.4050 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 18.3214 0.3790 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 19.2179 2.3016 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8658 -2.7019 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8906 -2.3629 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7580 0.8169 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8547 -2.7954 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6726 -0.4025 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0028 -3.3039 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3042 -2.7417 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5691 2.5577 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6925 -0.3749 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5124 2.5693 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0796 -0.2186 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3882 2.5577 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7977 0.1163 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5663 -2.2823 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2137 -2.2287 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6382 1.9284 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2391 4.1916 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6491 -0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8820 2.2832 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6715 2.7970 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4176 0.9951 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8470 3.4573 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1409 0.8075 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 1 0 9 10 2 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 1 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 1 0 22 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 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 52 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 56 59 1 0 55 60 1 0 47 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 62 65 1 0 61 66 1 0 63 45 1 0 57 50 1 0 1 67 1 0 1 68 1 0 1 69 1 0 2 70 1 0 2 71 1 0 3 72 1 0 4 73 1 0 5 74 1 0 5 75 1 0 6 76 1 0 7 77 1 0 8 78 1 0 8 79 1 0 9 80 1 0 10 81 1 0 11 82 1 0 11 83 1 0 12 84 1 0 12 85 1 0 13 86 1 0 13 87 1 0 14 88 1 0 14 89 1 0 15 90 1 0 15 91 1 0 16 92 1 0 16 93 1 0 17 94 1 0 17 95 1 0 21 96 1 0 21 97 1 0 22 98 1 1 26 99 1 0 26100 1 0 27101 1 0 27102 1 0 28103 1 0 28104 1 0 29105 1 0 29106 1 0 30107 1 0 30108 1 0 31109 1 0 31110 1 0 32111 1 0 32112 1 0 33113 1 0 34114 1 0 35115 1 0 35116 1 0 36117 1 0 37118 1 0 38119 1 0 38120 1 0 39121 1 0 40122 1 0 41123 1 0 41124 1 0 42125 1 0 42126 1 0 42127 1 0 43128 1 0 43129 1 0 45130 1 1 47131 1 1 48132 1 0 48133 1 0 50134 1 1 52135 1 6 53136 1 0 53137 1 0 54138 1 0 55139 1 6 56140 1 6 57141 1 1 58142 1 0 59143 1 0 60144 1 0 61145 1 1 62146 1 1 63147 1 6 64148 1 0 65149 1 0 66150 1 0 M END

Standard InCHIKey	KDYAPQVYJXUQNY-OPHDRXFHSA-N
Standard InCHI	InChI=1S/C51H84O15/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-42(53)61-36-39(64-43(54)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)37-62-50-49(60)47(58)45(56)41(66-50)38-63-51-48(59)46(57)44(55)40(35-52)65-51/h5-8,11-14,17-20,39-41,44-52,55-60H,3-4,9-10,15-16,21-38H2,1-2H3/b7-5-,8-6-,13-11-,14-12-,19-17-,20-18-/t39-,40-,41-,44+,45+,46+,47+,48-,49-,50-,51+/m1/s1
SMILES	CC/C=CC/C=CC/C=CCCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC/C=CC/C=CC/C=CCC)CO[C@@H]1O[C@H](CO[C@H]2O[C@H](CO)[C@@H]([C@@H]([C@H]2O)O)O)[C@@H]([C@@H]([C@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	936.58	Volume:	984.301 ? Van der Waals volume.
Dense:	0.952	LogP:	7.406 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.215 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.343 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	38.0	Rigid Bonds:	20.0
TPSA:	231.13 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	2.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.021	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.641	Fsp³:	0.725
MCE-18:	42.318 ? 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:	0.995	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.582	Promiscuous compounds:	0.079

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.438	MDCK Permeability:	-5.358
Pgp-inhibitor:	0.388	Pgp-substrate:	0.004
PAMPA:	0.001 ? 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):	0.004
20% Bioavailability (F20%):	0.995	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	97.462%	Volume Distribution (VD):	-0.446
Fu:	2.493% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.002	BCRP inhibitor:	0.015
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.633
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.0 ? 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):

0.997

Half-life (T1/2):

1.681

ADMET: Toxicity

hERG Blockers:	0.256	hERG Blockers (10um):	0.27
Human Hepatotoxicity (H-HT):	0.001	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	1.0	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.0	Eye Corrosion:	1.0
Eye Irritation:	1.0	Respiratory Toxicity:	0.922
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.155
Hematotoxicity:	0.0	Drug-induced Nephrotoxicity:	0.995
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.106
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.002
BCF:	1.14 ? 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:	5.496 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.859 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.868 ? 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
NPO5910	Phoma medicaginis	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795903]
NPO9537	Bauhinia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22348826]
NPO15967	Penicillium urticae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[836020]
NPO1611	Talaromyces pinophilus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15967	Penicillium urticae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8155	Lepidonia jonesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14701	Monodora angolensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5910	Phoma medicaginis	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13606	Iris pallasii	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8155	Lepidonia jonesii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1611	Talaromyces pinophilus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11080	Adenia volkensii	Species	Passifloraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9537	Bauhinia racemosa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15967	Penicillium urticae	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14701	Monodora angolensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12222	Baccharis angustifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO908	Euphorbia clarkeana	Species	Euphorbiaceae	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
Activity	2
Inhibition	15
MIC	2
IC50	2
CC50	1

Activity Type	# Activity
Cell line	1
Organism	21

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
NPT189	Cell line	Vero	Chlorocebus aethiops	CC50	>	100.0	ug.mL-1	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Activity	=	0.0	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Activity	=	-58.3	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	43.6	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	52.1	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	61.8	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	75.0	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	MIC	=	3.9	ug.mL-1	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	IC50	=	1.25	ug.mL-1	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	MIC	=	15.6	ug.mL-1	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	IC50	=	1.607	ug.mL-1	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	100.0	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	90.0	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	99.0	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	95.0	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	60.0	%	PMID[22348826]
NPT138	Organism	Brugia malayi	Brugia malayi	Inhibition	=	82.9	%	PMID[22348826]

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 NPC38295 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	20135
0.1-0.2	24443
0.2-0.3	4537
0.3-0.4	611
0.4-0.5	103
0.5-0.6	12
0.6-0.7	4
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9677	High Similarity	NPC470313
0.9677	High Similarity	NPC473500
0.9677	High Similarity	NPC611497
0.9167	High Similarity	NPC236649
0.8871	High Similarity	NPC156089
0.8571	High Similarity	NPC110813
0.8548	High Similarity	NPC21693
0.8281	Intermediate Similarity	NPC133377
0.8065	Intermediate Similarity	NPC488689
0.7887	Intermediate Similarity	NPC22558
0.7097	Intermediate Similarity	NPC488690
0.7067	Intermediate Similarity	NPC476611
0.6575	Remote Similarity	NPC488692
0.64	Remote Similarity	NPC476612
0.64	Remote Similarity	NPC476613
0.6164	Remote Similarity	NPC488694
0.5909	Remote Similarity	NPC285003
0.5758	Remote Similarity	NPC12040
0.5571	Remote Similarity	NPC83839
0.5484	Remote Similarity	NPC54925
0.5417	Remote Similarity	NPC489083
0.5342	Remote Similarity	NPC488693
0.5323	Remote Similarity	NPC271921
0.527	Remote Similarity	NPC331437
0.5161	Remote Similarity	NPC145112
0.5152	Remote Similarity	NPC473559
0.5152	Remote Similarity	NPC324981
0.5068	Remote Similarity	NPC163812

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC38295 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6919
0.1-0.2	2111
0.2-0.3	102
0.3-0.4	15
0.4-0.5	3
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