NPASS Compound

Natural Product: NPC135849

Natural Product ID	NPC135849
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Dianversicoside D
IUPAC Name	(3S,4S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4S,5R,6R)-6-[[(2R,3R,4S,5S,6R)-6-[[(3S)-4-carboxy-3-hydroxy-3-methylbutanoyl]oxymethyl]-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxycarbonyl-3-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
Synonyms	Dianversicoside D
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL559335
PubChem CID	42640125
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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

Chemical Representations

RDKit 2D 183191 0 0 0 0 0 0 0 0999 V2000 8.5586 9.6278 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 8.3287 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 7.0297 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7981 5.5525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3886 5.0395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1386 3.7404 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3886 2.4414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7981 1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2981 1.9284 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8086 -0.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5586 -2.1469 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0586 -2.1469 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7981 -3.6241 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9472 -4.5883 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6972 -5.8874 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4472 -7.1864 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6972 -8.4854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1972 -8.4854 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 12.4472 -9.7845 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1972 -11.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.9472 -12.3825 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.6972 -13.6816 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 16.1972 -13.6816 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.9472 -14.9806 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8982 -11.8335 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 14.4962 -10.3335 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3567 -4.0753 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6172 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4681 -1.6339 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7181 -0.3349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.4681 0.9642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0586 1.4772 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 9.7981 2.9544 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0481 4.2535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2981 5.5525 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9472 3.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.3567 3.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6172 1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.3672 0.6293 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8567 3.4056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 11.6972 5.2176 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3672 -1.2990 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 13.8567 -4.0753 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9095 -0.5130 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 1.4772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4895 2.7762 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 -1.2990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -2.5981 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 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 -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 -1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7500 -3.8971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -5.1962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0000 -7.7942 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -9.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0105 -10.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3405 -9.6063 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9019 -11.0407 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1914 -8.6421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9895 -10.5705 0.0000 O 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 -0.4895 2.7762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 6.0037 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 7.4809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9095 7.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1595 9.2929 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 7.4809 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4895 4.7046 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0586 9.6278 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1076 7.5787 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6107 9.2315 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4681 6.5167 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4057 4.5602 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 3.4056 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8617 3.1417 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1422 1.0544 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2425 0.7244 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5096 -1.5979 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1076 -0.0979 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9951 -0.9336 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7981 -5.5525 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3982 -6.6374 0.0000 H 0 0 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 12.9538 -0.8126 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7595 2.2076 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9472 6.5167 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.8672 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7595 -2.8774 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 -1.4772 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7780 1.1398 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9029 4.2182 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5230 1.0971 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9183 -0.4882 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 2.1595 1.8121 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 -2.7580 0.8169 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2388 -1.4819 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7500 -1.2990 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0982 -4.5546 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8991 -2.9329 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -5.1962 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1595 -4.4101 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 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0 0 0 0 0 0 0 0 0 -6.6595 -9.6063 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2709 -12.0477 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5068 -10.6752 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5760 -11.0091 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1451 -9.3231 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1386 -11.5347 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5691 2.3251 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8222 3.2736 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8406 0.4756 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2291 4.2535 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9240 3.2148 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0084 2.6978 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 6.5167 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 8.9581 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9325 9.0910 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9095 10.5920 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2500 8.7799 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9895 4.7046 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 8 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 20 21 1 0 21 22 1 0 22 23 1 0 23 24 2 0 23 25 1 0 21 26 1 1 21 27 1 0 15 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 1 0 34 35 1 0 35 36 1 0 34 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 38 41 1 0 37 42 1 0 29 43 1 0 28 44 1 0 10 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 46 49 1 0 49 50 1 0 50 51 2 0 52 50 1 1 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 2 0 59 60 1 0 60 61 1 0 61 62 1 0 62 63 1 0 63 64 1 0 64 65 1 0 63 66 1 6 62 67 1 1 62 68 1 0 68 69 1 0 69 70 1 0 70 71 1 0 71 72 1 1 71 73 1 0 73 74 1 0 74 75 1 0 75 76 1 0 76 77 1 1 76 78 1 0 78 79 2 0 78 80 1 0 75 81 1 0 55 82 1 0 55 83 1 0 5 84 1 0 84 85 1 0 85 86 1 0 86 87 1 0 85 88 1 0 84 89 1 0 86 3 1 0 47 7 1 0 65 52 1 0 76 70 1 0 30 13 1 0 39 32 1 0 57 52 1 0 63 58 1 0 71 61 1 0 1 90 1 0 2 91 1 0 2 92 1 0 3 93 1 6 5 94 1 6 7 95 1 6 8 96 1 1 9 97 1 0 10 98 1 6 11 99 1 0 11100 1 0 13101 1 6 15102 1 6 16103 1 0 16104 1 0 20105 1 0 20106 1 0 22107 1 0 22108 1 0 25109 1 0 26110 1 0 27111 1 0 27112 1 0 27113 1 0 28114 1 1 29115 1 6 30116 1 1 32117 1 1 34118 1 1 35119 1 0 35120 1 0 36121 1 0 37122 1 6 38123 1 1 39124 1 6 40125 1 0 41126 1 0 42127 1 0 43128 1 0 44129 1 0 46130 1 6 47131 1 1 48132 1 0 53133 1 0 53134 1 0 54135 1 0 54136 1 0 56137 1 0 56138 1 0 57139 1 1 59140 1 0 60141 1 0 60142 1 0 61143 1 6 64144 1 0 64145 1 0 65146 1 0 65147 1 0 66148 1 0 66149 1 0 66150 1 0 67151 1 0 67152 1 0 67153 1 0 68154 1 0 68155 1 0 69156 1 0 69157 1 0 70158 1 6 72159 1 0 72160 1 0 72161 1 0 73162 1 0 73163 1 0 74164 1 0 74165 1 0 75166 1 6 77167 1 0 77168 1 0 77169 1 0 80170 1 0 81171 1 0 82172 1 0 82173 1 0 82174 1 0 83175 1 0 83176 1 0 83177 1 0 84178 1 1 85179 1 6 86180 1 1 87181 1 0 88182 1 0 89183 1 0 M END

Standard InCHIKey	NMZXWJLQTSMVIG-YDKKYBOASA-N
Standard InCHI	InChI=1S/C60H94O29/c1-54(2)14-16-60(17-15-57(5)25(26(60)18-54)8-9-31-56(4)12-11-33(63)59(7,52(77)78)32(56)10-13-58(31,57)6)53(79)89-50-45(76)46(87-48-43(74)40(71)36(67)27(21-61)83-48)39(70)30(85-50)24-82-51-47(88-49-44(75)41(72)37(68)28(22-62)84-49)42(73)38(69)29(86-51)23-81-35(66)20-55(3,80)19-34(64)65/h8,26-33,36-51,61-63,67-76,80H,9-24H2,1-7H3,(H,64,65)(H,77,78)/t26-,27+,28+,29+,30+,31+,32+,33-,36+,37+,38+,39+,40-,41-,42-,43+,44+,45+,46-,47+,48-,49-,50-,51+,55-,56+,57+,58+,59-,60-/m0/s1
SMILES	OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](CO[C@@H]3O[C@H](COC(=O)C[C@](CC(=O)O)(O)C)[C@H]([C@@H]([C@H]3O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)O)O)O[C@H]([C@@H]2O)OC(=O)[C@@]23CCC(C[C@H]3C3=CC[C@H]4[C@@]([C@@]3(CC2)C)(C)CC[C@@H]2[C@]4(C)CC[C@@H]([C@@]2(C)C(=O)O)O)(C)C)[C@@H]([C@H]([C@@H]1O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1278.59	Volume:	1211.042 ? Van der Waals volume.
Dense:	1.056	LogP:	-0.772 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.055 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.78 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	20.0	Rigid Bonds:	54.0
TPSA:	475.03 ? Topological Polar Surface Area.	H-Bond Acceptor:	29.0
H-Bond Donor:	16.0	Rings:	9.0
Heavy Atoms:	29.0

MedChem Properties

QED Drug-Likeness Score:	0.049	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.302	Fsp³:	0.9
MCE-18:	208.035 ? 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:	0.673	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? 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:	0.182	Promiscuous compounds:	0.567

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.658	MDCK Permeability:	-5.065
Pgp-inhibitor:	0.0	Pgp-substrate:	0.002
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):	0.884
20% Bioavailability (F20%):	0.951	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.003
Plasma Protein Binding (PPB):	66.373%	Volume Distribution (VD):	-0.535
Fu:	27.657% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.022	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

-0.797

Half-life (T1/2):

4.801

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.952	Drug-induced Liver Injury (DILI):	0.76
AMES Toxicity:	0.707	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.057	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.743	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.903	RPMI-8226 Immunitoxicity:	0.16
A549 Cytotoxicity:	0.162	Hek293 Cytotoxicity:	0.028
BCF:	0.423 ? 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:	3.256 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.951 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.715 ? 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
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[19290648]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	aerial parts	Changqing, Shangdong Province, China	2004-JUN	PMID[19290648]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27907	Dianthus versicolor	Species	Caryophyllaceae	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	4

Activity Type	# Activity
Cell line	3
Non-molecular	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
NPT1855	Cell line	HFL1	Homo sapiens	IC50	=	3400.0	nM	PMID[19290648]
NPT83	Cell line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[19290648]
NPT65	Cell line	HepG2	Homo sapiens	IC50	>	10000.0	nM	PMID[19290648]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	2900.0	nM	PMID[19290648]

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 NPC135849 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	23212
0.1-0.2	22794
0.2-0.3	2887
0.3-0.4	625
0.4-0.5	264
0.5-0.6	61
0.6-0.7	3
0.7-0.8	0
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8729	High Similarity	NPC51564
0.8468	Intermediate Similarity	NPC75287
0.7928	Intermediate Similarity	NPC609763
0.7244	Intermediate Similarity	NPC476991
0.7016	Intermediate Similarity	NPC191827
0.6562	Remote Similarity	NPC25663
0.6148	Remote Similarity	NPC473459
0.6094	Remote Similarity	NPC476992
0.5868	Remote Similarity	NPC150400
0.5812	Remote Similarity	NPC209894
0.5758	Remote Similarity	NPC79643
0.5736	Remote Similarity	NPC69811
0.5612	Remote Similarity	NPC65105
0.5612	Remote Similarity	NPC43550
0.5563	Remote Similarity	NPC478824
0.5556	Remote Similarity	NPC123199
0.5515	Remote Similarity	NPC470218
0.55	Remote Similarity	NPC293330
0.5469	Remote Similarity	NPC63159
0.5448	Remote Similarity	NPC300419
0.5429	Remote Similarity	NPC41061
0.5429	Remote Similarity	NPC227551
0.5417	Remote Similarity	NPC250247
0.541	Remote Similarity	NPC29069
0.5391	Remote Similarity	NPC251768
0.5391	Remote Similarity	NPC159309
0.5391	Remote Similarity	NPC86222
0.5366	Remote Similarity	NPC48499
0.5352	Remote Similarity	NPC305981
0.5338	Remote Similarity	NPC481078
0.5315	Remote Similarity	NPC261506
0.5315	Remote Similarity	NPC298034
0.5315	Remote Similarity	NPC71065
0.5315	Remote Similarity	NPC4328
0.5312	Remote Similarity	NPC309714
0.5308	Remote Similarity	NPC475504
0.5303	Remote Similarity	NPC481079
0.5248	Remote Similarity	NPC473645
0.5234	Remote Similarity	NPC192791
0.5234	Remote Similarity	NPC223301
0.5234	Remote Similarity	NPC171544
0.5227	Remote Similarity	NPC104372
0.5227	Remote Similarity	NPC114484
0.5211	Remote Similarity	NPC258617
0.5188	Remote Similarity	NPC301449
0.5188	Remote Similarity	NPC601290
0.517	Remote Similarity	NPC478825
0.5159	Remote Similarity	NPC475516
0.5154	Remote Similarity	NPC305267
0.5149	Remote Similarity	NPC96641
0.5149	Remote Similarity	NPC163183
0.5145	Remote Similarity	NPC323341
0.5128	Remote Similarity	NPC167383
0.5116	Remote Similarity	NPC112352
0.5108	Remote Similarity	NPC166422
0.5106	Remote Similarity	NPC481080
0.5078	Remote Similarity	NPC295371
0.5076	Remote Similarity	NPC222580
0.507	Remote Similarity	NPC476068
0.5042	Remote Similarity	NPC237503
0.5039	Remote Similarity	NPC473343
0.5039	Remote Similarity	NPC469946
0.5035	Remote Similarity	NPC54636
0.5034	Remote Similarity	NPC202828
0.5034	Remote Similarity	NPC119592
0.5034	Remote Similarity	NPC236638
0.5034	Remote Similarity	NPC294453
0.5034	Remote Similarity	NPC478823
0.5034	Remote Similarity	NPC481081

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC135849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6845
0.1-0.2	2264
0.2-0.3	40
0.3-0.4	1
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