NPASS Compound

Natural Product: NPC110602

Natural Product ID	NPC110602
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Cyclolinopeptide G
IUPAC Name	(3S,6S,9S,12S,15S,18S,21S,24S)-18,21-dibenzyl-12-[(2S)-butan-2-yl]-15-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-3,9-bis(2-methylsulfinylethyl)-1,4,7,10,13,16,19,22-octazabicyclo[22.3.0]heptacosane-2,5,8,11,14,17,20,23-octone
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3787164
PubChem CID	10724885
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

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 152157 0 0 0 0 0 0 0 0999 V2000 0.0878 -6.8644 0.2674 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2229 -6.1336 0.0624 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0240 -4.8185 -0.6358 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.3298 -4.9135 -1.9588 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7438 -3.6217 0.1835 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4305 -3.6840 1.0827 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5791 -3.2594 0.7504 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6887 -3.3315 1.6350 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1626 -4.7639 1.7942 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5740 -5.3535 0.4593 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2048 -7.0122 0.6267 S 0 0 0 0 0 0 0 0 0 0 0 0 4.5599 -7.5276 -0.7867 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0368 -8.1659 1.3419 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8563 -2.4752 1.1652 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6757 -1.9274 0.0307 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4631 -1.0829 -0.7613 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0457 -0.9363 -2.1921 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0563 -2.2039 -2.9870 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6003 -1.8938 -4.4044 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4078 -2.8503 -3.0802 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6253 0.3148 -0.2036 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2461 0.6583 0.9314 N 0 0 0 0 0 0 0 0 0 0 0 0 4.2605 1.8408 1.6932 C 0 0 1 0 0 0 0 0 0 0 0 0 5.4812 2.6482 1.8122 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6528 1.8616 2.4195 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0938 2.9544 2.5429 S 0 0 0 0 0 0 0 0 0 0 0 0 8.2871 3.5452 1.1285 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7284 4.3737 3.6052 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0588 2.6236 1.4158 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9841 1.8997 1.3293 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7703 3.9615 1.2076 N 0 0 0 0 0 0 0 0 0 0 0 0 3.5526 5.0979 1.0013 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7046 6.2484 1.5842 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3396 5.8098 1.0420 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3666 4.3265 1.0929 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8526 3.6862 -0.1807 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3115 3.4901 -0.3236 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6398 3.2936 -0.4265 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2493 3.1923 -1.8121 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9712 4.4586 -2.5241 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7674 5.5714 -2.3971 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5046 6.7528 -3.0622 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4073 6.8682 -3.9036 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6179 5.7588 -4.0296 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8681 4.6007 -3.3803 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1564 2.1278 0.4176 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3132 2.1072 0.7920 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1704 1.2875 1.5376 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6640 1.6277 1.3328 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9398 3.0110 1.7501 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3603 3.3317 3.0211 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6248 4.5926 3.4490 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4631 5.6769 2.5616 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0455 5.3776 1.2931 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7836 4.0687 0.8741 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9777 -0.1322 1.0529 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2810 -0.3468 0.0389 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9619 -1.6054 -0.6019 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.7295 -1.6913 -1.9365 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1814 -1.5106 -1.5694 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8947 -0.3683 -1.8446 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1185 -0.5511 -1.3619 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.2519 -1.7443 -0.7877 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2691 -2.3725 -0.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0961 -3.6596 0.3758 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8877 -4.2355 0.2347 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8282 -3.6358 -0.3967 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9844 -2.3842 -0.9184 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5118 -1.6120 -1.0101 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6469 -2.4522 -0.6680 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0626 -0.5770 -1.8635 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5918 -1.1817 1.7483 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2507 1.0998 0.7309 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7453 3.3142 -1.2042 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2333 1.2128 -1.0497 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9602 -2.3543 1.9382 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2436 -4.2402 2.3507 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7437 -6.7538 -0.6396 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6199 -6.5136 1.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0571 -7.9765 0.3710 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6767 -5.9325 1.0759 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9058 -6.8221 -0.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1616 -4.6463 -1.0198 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5171 -5.9064 -2.4226 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7715 -4.1630 -2.6646 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7606 -4.6815 -1.9213 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6934 -3.4310 0.7880 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5002 -2.9450 2.6705 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0679 -4.7712 2.4332 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4115 -5.3892 2.2819 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2868 -4.7193 -0.0736 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6594 -5.4034 -0.1598 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4457 -7.6986 2.1644 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3504 -8.6001 0.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5980 -9.0065 1.8478 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5306 -1.4988 -0.7518 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5975 -0.1595 -2.7494 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9760 -0.5859 -2.1975 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3522 -2.9597 -2.5681 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3266 -1.2174 -4.8578 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5588 -1.5425 -4.4516 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6589 -2.8404 -4.9752 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5465 -3.6419 -2.3173 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4563 -3.3846 -4.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2580 -2.1551 -3.0670 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0408 1.4918 2.8282 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8495 3.2383 1.0033 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2853 3.4130 2.6608 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4026 1.4654 3.4012 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9676 1.0300 1.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1463 4.1586 4.5940 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6475 4.5369 3.6101 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2179 5.2925 3.1770 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6477 5.3691 -0.0944 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5706 5.1487 1.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0189 7.2036 1.1910 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6892 6.1833 2.6844 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5465 6.1619 1.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2151 6.1665 0.0207 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7846 3.9216 1.9625 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1991 4.1722 0.0452 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3317 3.0677 -1.7216 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7816 2.3615 -2.3867 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6416 5.5563 -1.7542 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1348 7.6177 -2.9516 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1926 7.7809 -4.4259 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2724 5.7931 -4.6826 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2419 3.7445 -3.5142 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0283 1.2925 2.6497 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9475 1.5207 0.2642 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2286 0.9350 1.9794 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5059 2.5295 3.7654 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9545 4.8506 4.4405 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6566 6.6835 2.8774 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9024 6.1419 0.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4562 3.8678 -0.1419 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 -2.4345 0.0102 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5696 -2.6804 -2.3646 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3946 -0.9273 -2.6450 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4939 0.5069 -2.3647 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8853 0.1678 -1.4210 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2265 -1.9264 -0.0355 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9215 -4.1398 0.8722 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7205 -5.2369 0.6345 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8616 -4.1352 -0.4938 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1501 -0.1549 -1.7130 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1975 -2.1008 1.7862 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3513 0.7310 1.6946 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6442 3.6682 -2.1647 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9153 1.8668 -0.7960 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7884 -1.8450 1.5840 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7620 -3.9087 3.1591 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 3 5 1 0 5 6 1 0 6 7 2 3 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 2 0 11 13 1 0 8 14 1 0 14 15 2 3 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 16 21 1 0 21 22 2 3 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 23 29 1 0 29 30 2 0 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 2 3 37 38 1 0 38 39 1 0 39 40 1 0 40 41 2 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 38 46 1 0 46 47 2 3 47 48 1 0 48 49 1 0 49 50 1 0 50 51 2 0 51 52 1 0 52 53 2 0 53 54 1 0 54 55 2 0 48 56 1 0 56 57 2 3 57 58 1 0 58 59 1 0 59 60 1 0 60 61 2 0 61 62 1 0 62 63 1 0 63 64 2 0 64 65 1 0 65 66 2 0 66 67 1 0 67 68 2 0 58 69 1 0 69 70 2 3 69 71 1 0 56 72 1 0 46 73 1 0 36 74 1 0 21 75 1 0 14 76 1 0 6 77 1 0 70 5 1 0 35 31 1 0 45 40 1 0 55 50 1 0 68 60 1 0 68 63 1 0 1 78 1 0 1 79 1 0 1 80 1 0 2 81 1 0 2 82 1 0 3 83 1 6 4 84 1 0 4 85 1 0 4 86 1 0 5 87 1 1 8 88 1 1 9 89 1 0 9 90 1 0 10 91 1 0 10 92 1 0 13 93 1 0 13 94 1 0 13 95 1 0 16 96 1 6 17 97 1 0 17 98 1 0 18 99 1 0 19100 1 0 19101 1 0 19102 1 0 20103 1 0 20104 1 0 20105 1 0 23106 1 1 24107 1 0 24108 1 0 25109 1 0 25110 1 0 28111 1 0 28112 1 0 28113 1 0 32114 1 0 32115 1 0 33116 1 0 33117 1 0 34118 1 0 34119 1 0 35120 1 1 38121 1 1 39122 1 0 39123 1 0 41124 1 0 42125 1 0 43126 1 0 44127 1 0 45128 1 0 48129 1 1 49130 1 0 49131 1 0 51132 1 0 52133 1 0 53134 1 0 54135 1 0 55136 1 0 58137 1 1 59138 1 0 59139 1 0 61140 1 0 62141 1 0 64142 1 0 65143 1 0 66144 1 0 67145 1 0 71146 1 0 72147 1 0 73148 1 0 74149 1 0 75150 1 0 76151 1 0 77152 1 0 M END

Standard InCHIKey	MGTCVHJATWUGDT-JVXUKOSASA-N
Standard InCHI	InChI=1S/C56H75N9O10S2/c1-7-35(4)48-55(72)58-41(24-27-76(5)74)49(66)60-43(29-34(2)3)50(67)59-42(25-28-77(6)75)56(73)65-26-16-23-47(65)54(71)63-45(31-37-19-12-9-13-20-37)52(69)61-44(30-36-17-10-8-11-18-36)51(68)62-46(53(70)64-48)32-38-33-57-40-22-15-14-21-39(38)40/h8-15,17-22,33-35,41-48,57H,7,16,23-32H2,1-6H3,(H,58,72)(H,59,67)(H,60,66)(H,61,69)(H,62,68)(H,63,71)(H,64,70)/t35-,41-,42-,43-,44-,45-,46-,47-,48-,76?,77?/m0/s1
SMILES	CC[C@H](C)[C@H]1C(=N[C@@H](CCS(=O)C)C(=N[C@@H](CC(C)C)C(=N[C@@H](CCS(=O)C)C(=O)N2CCC[C@H]2C(=N[C@@H](Cc2ccccc2)C(=N[C@@H](Cc2ccccc2)C(=N[C@@H](Cc2c[nH]c3ccccc23)C(=N1)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1097.51	Volume:	1102.228 ? Van der Waals volume.
Dense:	0.996	LogP:	-0.17 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.907 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.46 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	16.0	Rigid Bonds:	51.0
TPSA:	310.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	8.0	Rings:	6.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.05	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.258	Fsp³:	0.5
MCE-18:	143.524 ? 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:	0.734	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.47 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.187	Promiscuous compounds:	0.156

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.455	MDCK Permeability:	-5.011
Pgp-inhibitor:	0.965	Pgp-substrate:	1.0
PAMPA:	0.184 ? 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):	0.875
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.53
Plasma Protein Binding (PPB):	74.072%	Volume Distribution (VD):	-0.495
Fu:	22.897% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.962
OATP1B3 inhibitor:	0.065	BCRP inhibitor:	0.075
BSEP inhibitor:	0.975

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.005
CYP2C9-inhibitor:	0.444	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.092 ? 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):

0.703

Half-life (T1/2):

2.121

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	1.0	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.199	Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.999	Skin Sensitization:	1.0
Carcinogencity:	0.619	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.972
Drug-induced Neurotoxicity:	0.017	Ototoxicity:	0.999
Hematotoxicity:	0.315	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.0
A549 Cytotoxicity:	0.0	Hek293 Cytotoxicity:	0.0
BCF:	0.395 ? 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:	3.478 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.047 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.206 ? 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
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24417583]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26923696]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25114	Linum usitatissimum	Species	Linaceae	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
IC50	1

Activity Type	# Activity
Cell line	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
NPT21723	Cell line	Bone marrow cell	n.a.	IC50	=	4040.0	nM	PMID[26923696]

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 NPC110602 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	29494
0.1-0.2	18504
0.2-0.3	1330
0.3-0.4	358
0.4-0.5	117
0.5-0.6	33
0.6-0.7	13
0.7-0.8	0
0.8-0.85	3
0.85-0.9	2
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9773	High Similarity	NPC479071
0.9326	High Similarity	NPC31385
0.8958	High Similarity	NPC75726
0.8854	High Similarity	NPC479066
0.8367	Intermediate Similarity	NPC479076
0.8265	Intermediate Similarity	NPC479073
0.8163	Intermediate Similarity	NPC479065
0.76	Intermediate Similarity	NPC479075
0.6609	Remote Similarity	NPC325976
0.6609	Remote Similarity	NPC326363
0.6602	Remote Similarity	NPC223791
0.6571	Remote Similarity	NPC54420
0.6489	Remote Similarity	NPC479072
0.6471	Remote Similarity	NPC107077
0.6449	Remote Similarity	NPC162860
0.641	Remote Similarity	NPC479574
0.6373	Remote Similarity	NPC293917
0.6354	Remote Similarity	NPC487314
0.6162	Remote Similarity	NPC479070
0.6139	Remote Similarity	NPC489625
0.6134	Remote Similarity	NPC489555
0.5909	Remote Similarity	NPC75634
0.5865	Remote Similarity	NPC484874
0.5747	Remote Similarity	NPC49954
0.5678	Remote Similarity	NPC100321
0.567	Remote Similarity	NPC479068
0.5664	Remote Similarity	NPC482001
0.5575	Remote Similarity	NPC155143
0.5556	Remote Similarity	NPC483341
0.5543	Remote Similarity	NPC17059
0.5524	Remote Similarity	NPC213629
0.5446	Remote Similarity	NPC34779
0.5437	Remote Similarity	NPC479074
0.5402	Remote Similarity	NPC63751
0.5366	Remote Similarity	NPC483985
0.5354	Remote Similarity	NPC489557
0.5294	Remote Similarity	NPC489822
0.5234	Remote Similarity	NPC487596
0.5217	Remote Similarity	NPC479572
0.5217	Remote Similarity	NPC479568
0.5217	Remote Similarity	NPC479573
0.5217	Remote Similarity	NPC479566
0.5217	Remote Similarity	NPC479567
0.5217	Remote Similarity	NPC479569
0.5217	Remote Similarity	NPC479571
0.5182	Remote Similarity	NPC171317
0.5172	Remote Similarity	NPC479570
0.5143	Remote Similarity	NPC322878
0.5093	Remote Similarity	NPC479069
0.5078	Remote Similarity	NPC486282
0.5051	Remote Similarity	NPC489593
0.5047	Remote Similarity	NPC261934
0.5043	Remote Similarity	NPC489590
0.5034	Remote Similarity	NPC320968

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC110602 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3675
0.1-0.2	5129
0.2-0.3	293
0.3-0.4	36
0.4-0.5	12
0.5-0.6	3
0.6-0.7	2
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
0.6373	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD8405	Pre-clinical
0.521	Remote Similarity	NPD7711	Discontinued
0.5138	Remote Similarity	NPD8110	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