NPASS Compound

Natural Product: NPC476781

Natural Product ID	NPC476781
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	caminosides B
IUPAC Name	[(2S,3R,4S,5R,6R)-5-butoxy-2-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-[(10R)-2-oxononadecan-10-yl]oxyoxan-3-yl]oxy-3-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-4-yl] butanoate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	44566240
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003918] Saccharolipids

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 164167 0 0 0 0 0 0 0 0999 V2000 -9.0767 5.1240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1125 3.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1483 2.8258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1842 1.6768 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2200 0.5277 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2558 -0.6214 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2916 -1.7704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3274 -2.9195 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3632 -4.0686 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -6.3667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5293 -7.5158 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4935 -8.6648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4577 -9.8139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4218 -10.9630 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3860 -12.1120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3502 -13.2611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3144 -14.4102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7916 -14.1497 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8014 -15.8197 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 -2.7762 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 -0.3991 -0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8086 -0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0691 -2.3251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9200 -3.2893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4786 -1.8121 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8882 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0691 0.6293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 0.6293 0.0000 O 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 2.4200 -3.2893 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 -2.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -3.7404 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 -5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 -5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -4.7665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -6.6949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0105 -7.6590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -7.1460 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6595 -8.6232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0691 -9.1362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2181 -8.1721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9577 -6.6949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5481 -6.1818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2181 -5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6277 -7.6590 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2181 -10.1004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3991 -10.1004 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -6.6949 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8296 -7.6590 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6805 -8.6232 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5314 -9.5874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3824 -10.5516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -4.2535 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6486 -5.7307 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7670 -6.9442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0582 -6.2437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4677 -6.7567 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8772 -7.2698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9786 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 -2.3251 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6486 -0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0582 -0.3349 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2072 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9468 -2.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5372 -3.2893 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2072 -4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6168 -1.8121 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2072 0.6293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3882 0.6293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0409 6.2730 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2258 4.1598 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9276 6.0881 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9635 4.9391 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2616 3.0107 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9993 3.7900 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2974 1.8616 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3332 0.7126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0351 2.6409 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3690 -0.4365 0.0000 H 0 0 0 0 0 0 0 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0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5351 -11.1479 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2011 -14.2253 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4993 -12.2969 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2883 -17.2293 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2109 -16.3327 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3918 -15.3067 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9450 -3.1392 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1491 0.9642 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2974 -0.6650 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1111 -3.4041 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4628 -2.9441 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9656 -0.4025 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0372 -2.2632 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3126 1.4682 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4895 2.1065 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9646 -3.6522 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0796 -1.4772 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0207 -2.6615 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1736 -5.5806 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8947 -7.1114 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9765 -7.9529 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5021 -5.3466 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5037 -5.9481 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8405 -8.6232 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4830 -10.5170 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1209 -9.3700 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4465 -6.5120 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9908 -3.9320 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7161 -5.2961 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7202 -5.1392 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2379 -6.2888 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6797 -9.7630 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5481 -11.0646 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7325 -6.6361 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9266 -8.6820 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8941 -9.5048 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7163 -7.4742 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3483 -10.8454 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3178 -8.7058 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6406 -11.6486 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3465 -11.7006 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0085 -9.9898 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5451 -7.6532 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3956 -4.7821 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9547 -8.1663 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1487 -5.4202 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2868 -7.7828 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3642 -8.6793 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.3903 -5.8602 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9748 -3.7670 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1486 -0.8479 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4721 1.0459 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1100 -0.1011 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4356 -2.9591 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6458 -5.6879 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7052 -4.1750 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7093 -4.3319 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2270 -3.1824 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6688 0.2919 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4111 1.7264 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 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 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 10 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 26 28 1 0 28 29 1 0 25 30 1 0 24 31 1 0 23 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 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 45 47 1 0 44 48 1 0 43 49 1 0 42 50 1 0 36 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 35 56 1 0 56 57 1 0 57 58 2 0 57 59 1 0 59 60 1 0 60 61 1 0 34 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 65 66 1 0 66 67 1 0 67 68 1 0 67 69 1 0 66 70 1 0 65 71 1 0 64 72 1 0 27 22 1 0 38 33 1 0 46 41 1 0 68 63 1 0 1 73 1 0 1 74 1 0 1 75 1 0 2 76 1 0 2 77 1 0 3 78 1 0 3 79 1 0 4 80 1 0 4 81 1 0 5 82 1 0 5 83 1 0 6 84 1 0 6 85 1 0 7 86 1 0 7 87 1 0 8 88 1 0 8 89 1 0 9 90 1 0 9 91 1 0 10 92 1 6 11 93 1 0 11 94 1 0 12 95 1 0 12 96 1 0 13 97 1 0 13 98 1 0 14 99 1 0 14100 1 0 15101 1 0 15102 1 0 16103 1 0 16104 1 0 17105 1 0 17106 1 0 20107 1 0 20108 1 0 20109 1 0 22110 1 1 23111 1 6 24112 1 1 25113 1 6 26114 1 1 28115 1 0 28116 1 0 29117 1 0 30118 1 0 31119 1 0 33120 1 6 34121 1 1 35122 1 6 36123 1 1 37124 1 6 39125 1 0 39126 1 0 41127 1 6 42128 1 6 43129 1 6 44130 1 6 45131 1 6 47132 1 0 47133 1 0 47134 1 0 48135 1 0 49136 1 0 50137 1 0 52138 1 0 52139 1 0 53140 1 0 53141 1 0 54142 1 0 54143 1 0 55144 1 0 55145 1 0 55146 1 0 59147 1 0 59148 1 0 60149 1 0 60150 1 0 61151 1 0 61152 1 0 61153 1 0 63154 1 6 64155 1 6 65156 1 1 66157 1 6 67158 1 1 69159 1 0 69160 1 0 69161 1 0 70162 1 0 71163 1 0 72164 1 0 M END

Standard InCHIKey	QNFTZMDCINQYDC-QFUKRXFTSA-N
Standard InCHI	InChI=1S/C51H92O21/c1-7-10-12-13-14-17-20-24-32(25-21-18-15-16-19-23-29(4)53)67-50-45(41(60)38(57)33(27-52)68-50)71-51-47(72-49-43(62)40(59)37(56)31(6)66-49)46(70-35(54)22-9-3)44(63-26-11-8-2)34(69-51)28-64-48-42(61)39(58)36(55)30(5)65-48/h30-34,36-52,55-62H,7-28H2,1-6H3/t30-,31+,32-,33-,34-,36+,37+,38-,39+,40-,41+,42+,43+,44-,45-,46+,47-,48-,49+,50-,51+/m1/s1
SMILES	CCCCCCCCC[C@H](CCCCCCCC(=O)C)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO[C@H]3[C@H]([C@H]([C@H]([C@H](O3)C)O)O)O)OCCCC)OC(=O)CCC)O[C@H]4[C@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1040.61	Volume:	1035.748 ? Van der Waals volume.
Dense:	1.005	LogP:	3.367 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.298 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.407 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	34.0	Rigid Bonds:	26.0
TPSA:	308.51 ? Topological Polar Surface Area.	H-Bond Acceptor:	21.0
H-Bond Donor:	9.0	Rings:	4.0
Heavy Atoms:	21.0

MedChem Properties

QED Drug-Likeness Score:	0.034	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.157	Fsp³:	0.961
MCE-18:	84.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.95	Fluc inhibitor:	0.311 ? 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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.428	Promiscuous compounds:	0.185

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.456	MDCK Permeability:	-5.112
Pgp-inhibitor:	0.0	Pgp-substrate:	1.0
PAMPA:	0.999 ? 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):	1.0
20% Bioavailability (F20%):	0.997	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.949
Plasma Protein Binding (PPB):	92.566%	Volume Distribution (VD):	0.142
Fu:	6.268% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.678
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.005
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.004
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.21 ? 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):

1.116

Half-life (T1/2):

1.581

ADMET: Toxicity

hERG Blockers:	0.014	hERG Blockers (10um):	0.081
Human Hepatotoxicity (H-HT):	0.268	Drug-induced Liver Injury (DILI):	0.822
AMES Toxicity:	0.683	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.009	Eye Corrosion:	0.0
Eye Irritation:	0.024	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.813	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.388
A549 Cytotoxicity:	0.997	Hek293 Cytotoxicity:	0.503
BCF:	1.865 ? 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:	5.236 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.238 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.861 ? 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
NPO27310	Caminus sphaeroconia	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12423093]
NPO27310	Caminus sphaeroconia	Species	Geodiidae	Eukaryota	n.a.	at 10 m from Toucari Caves in Dominica, Netherlands	n.a.	PMID[16499312]
NPO27310	Caminus sphaeroconia	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27310	Caminus sphaeroconia	Species	Geodiidae	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
MIC	4
IC50	1

Activity Type	# Activity
Organism	5

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
NPT1605	Organism	Enterococcus	Enterococcus	MIC	=	3.1	ug	PMID[16499312]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	6.3	ug	PMID[16499312]
NPT1521	Organism	Stenotrophomonas maltophilia	Stenotrophomonas maltophilia	MIC	>	25	ug	PMID[16499312]
NPT19	Organism	Escherichia coli	Escherichia coli	IC50	=	20000	nM	PMID[16499312]
NPT2527	Organism	Pythium ultimum	Pythium ultimum	MIC	=	25	ug	PMID[16499312]

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 NPC476781 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	23902
0.1-0.2	22050
0.2-0.3	3433
0.3-0.4	361
0.4-0.5	79
0.5-0.6	25
0.6-0.7	1
0.7-0.8	0
0.8-0.85	1
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8902	High Similarity	NPC476783
0.8831	High Similarity	NPC216883
0.8353	Intermediate Similarity	NPC476782
0.631	Remote Similarity	NPC477350
0.5955	Remote Similarity	NPC22742
0.5955	Remote Similarity	NPC477349
0.5955	Remote Similarity	NPC477346
0.5862	Remote Similarity	NPC475425
0.5376	Remote Similarity	NPC604005
0.5376	Remote Similarity	NPC605014
0.5312	Remote Similarity	NPC478725
0.5263	Remote Similarity	NPC600446
0.5263	Remote Similarity	NPC605013
0.5258	Remote Similarity	NPC478724
0.519	Remote Similarity	NPC206823
0.5169	Remote Similarity	NPC478729
0.5155	Remote Similarity	NPC146992
0.5155	Remote Similarity	NPC85759
0.5109	Remote Similarity	NPC477330
0.5104	Remote Similarity	NPC477344
0.5102	Remote Similarity	NPC173328
0.5102	Remote Similarity	NPC478723
0.5054	Remote Similarity	NPC477329
0.5052	Remote Similarity	NPC109887
0.5051	Remote Similarity	NPC472204
0.5051	Remote Similarity	NPC294748
0.5051	Remote Similarity	NPC186992
0.505	Remote Similarity	NPC184915
0.5049	Remote Similarity	NPC478728

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476781 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7235
0.1-0.2	1842
0.2-0.3	71
0.3-0.4	2
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