NPASS Compound

Natural Product: NPC313175

Natural Product ID	NPC313175
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MNXFXXWQAAMVMW-LUOLZRRASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	101941091
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 206216 0 0 0 0 0 0 0 0999 V2000 -0.7391 5.2176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0109 3.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1600 4.8828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 4.3698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 2.8925 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6809 1.9284 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2714 2.4414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 0.9642 0.0000 O 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 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 7.0586 0.4512 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4681 0.9642 0.0000 C 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 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 -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 -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 -3.7500 -6.4952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5000 -7.7942 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 -2.3405 -9.6063 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 -1.5000 -7.7942 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 -5.1962 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 -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 0.7500 -1.2990 0.0000 O 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 -2.9875 -11.6675 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4200 -11.0835 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6595 -9.6063 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9200 -11.0835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3296 -10.5705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4786 -11.5347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2181 -13.0119 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8086 -13.5249 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5586 -14.8239 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3086 -16.1230 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6595 -12.5607 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7181 -13.0119 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2286 -10.2356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5796 -9.2714 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1491 -6.8300 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0586 3.4056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.4681 3.9186 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.4911 2.8215 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7286 5.3958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 10.1382 5.9088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.2872 4.9447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 11.0268 3.4675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1758 2.5033 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.5854 3.0163 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 13.8458 4.4935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6968 5.4577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 15.2554 5.0065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 15.5158 6.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 14.7344 2.0521 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 16.1440 2.5652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 3.4056 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5800 1.5935 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0695 4.3698 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9100 6.1818 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1600 7.4809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 7.9939 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 9.4711 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6809 10.4353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2714 9.9223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0109 8.4450 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 11.3995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 12.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0695 12.8767 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8195 14.1757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0695 15.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5695 15.4748 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 16.9520 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0905 18.4292 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8195 14.1757 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4791 15.9878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9686 13.2115 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8090 11.3995 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2395 8.9581 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.8300 6.5167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3399 6.2597 0.0000 H 0 0 0 0 0 0 0 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H 0 0 0 0 0 0 0 0 0 0 0 0 4.8195 5.6688 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1882 6.8234 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0695 7.9939 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8720 10.5501 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7782 11.6332 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2286 9.9223 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0109 11.3995 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1080 12.5393 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4791 12.3636 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9686 15.1399 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9911 16.9727 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1600 15.9878 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3279 16.8735 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3528 17.2124 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9414 19.3934 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7395 17.4650 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3781 13.7246 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0671 10.5825 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4976 9.7750 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2916 6.1793 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 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 19 17 1 1 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 1 31 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 1 36 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 1 41 43 1 0 43 44 1 0 44 45 1 0 43 46 1 6 46 47 1 0 36 48 1 0 48 49 2 0 48 50 1 0 35 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 56 59 1 0 55 60 1 0 54 61 1 0 53 62 1 0 34 63 1 0 11 64 1 0 64 65 1 0 65 66 2 0 65 67 1 0 67 68 2 0 68 69 1 0 69 70 2 0 70 71 1 0 71 72 2 0 72 73 1 0 73 74 2 0 73 75 1 0 75 76 1 0 72 77 1 0 77 78 1 0 10 79 1 0 5 80 1 0 4 81 1 0 3 82 1 0 82 83 1 0 83 84 1 0 84 85 1 0 85 86 1 0 86 87 1 0 87 88 1 0 86 89 1 0 89 90 1 0 90 91 1 0 91 92 1 0 92 93 1 0 93 94 1 0 94 95 1 0 95 96 1 0 94 97 1 0 93 98 1 0 92 99 1 0 91100 1 0 85101 1 0 84102 1 0 7 2 1 0 15 9 1 0 45 19 1 0 59 52 1 0 74 69 1 0 88 83 1 0 97 90 1 0 26 19 1 0 43 27 1 0 41 30 1 0 38 31 1 0 1103 1 0 1104 1 0 1105 1 0 2106 1 6 3107 1 1 4108 1 6 5109 1 6 6110 1 1 9111 1 1 10112 1 6 11113 1 6 12114 1 6 13115 1 0 13116 1 0 13117 1 0 15118 1 6 20119 1 0 20120 1 0 21121 1 0 21122 1 0 23123 1 0 23124 1 0 23125 1 0 24126 1 0 24127 1 0 24128 1 0 25129 1 0 25130 1 0 26131 1 1 28132 1 0 29133 1 0 29134 1 0 30135 1 6 32136 1 0 32137 1 0 32138 1 0 33139 1 0 33140 1 0 34141 1 6 35142 1 6 37143 1 0 37144 1 0 37145 1 0 38146 1 6 39147 1 0 39148 1 0 40149 1 0 40150 1 0 42151 1 0 42152 1 0 42153 1 0 44154 1 0 44155 1 0 45156 1 0 45157 1 0 46158 1 0 46159 1 0 47160 1 0 50161 1 0 52162 1 1 53163 1 6 54164 1 1 55165 1 6 56166 1 1 57167 1 0 57168 1 0 58169 1 0 60170 1 0 61171 1 0 62172 1 0 63173 1 0 67174 1 0 68175 1 0 70176 1 0 71177 1 0 74178 1 0 76179 1 0 76180 1 0 76181 1 0 78182 1 0 78183 1 0 78184 1 0 79185 1 0 80186 1 0 81187 1 0 83188 1 1 84189 1 6 85190 1 1 86191 1 6 87192 1 0 87193 1 0 90194 1 1 91195 1 6 92196 1 1 93197 1 1 94198 1 1 95199 1 0 95200 1 0 96201 1 0 98202 1 0 99203 1 0 100204 1 0 101205 1 0 102206 1 0 M END

Standard InCHIKey	MNXFXXWQAAMVMW-LUOLZRRASA-N
Standard InCHI	InChI=1S/C70H104O32/c1-29-54(99-58-49(82)45(78)39(27-92-58)97-60-50(83)46(79)43(76)37(25-71)95-60)48(81)52(85)59(93-29)100-56-53(86)55(98-42(75)15-11-31-10-13-35(90-8)36(22-31)91-9)30(2)94-62(56)102-64(89)69-19-18-65(3,4)23-33(69)32-12-14-40-66(5)24-34(74)57(101-61-51(84)47(80)44(77)38(26-72)96-61)68(7,63(87)88)41(66)16-17-67(40,6)70(32,28-73)21-20-69/h10-13,15,22,29-30,33-34,37-41,43-62,71-74,76-86H,14,16-21,23-28H2,1-9H3,(H,87,88)/b15-11-/t29-,30+,33-,34-,37+,38+,39+,40+,41+,43-,44+,45-,46-,47-,48-,49+,50+,51+,52+,53-,54-,55-,56+,57-,58-,59-,60-,61-,62-,66+,67+,68-,69-,70-/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]1[C@H]([C@H]([C@@H](C)O[C@H]1OC(=O)[C@@]12CCC(C)(C)C[C@H]2C2=CC[C@@H]3[C@@]4(C)C[C@@H]([C@@H]([C@](C)([C@@H]4CC[C@@]3(C)[C@@]2(CC1)CO)C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)OC(=O)/C=Cc1ccc(c(c1)OC)OC)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O[C@H]1[C@@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	1456.65	Volume:	1385.35 ? Van der Waals volume.
Dense:	1.051	LogP:	-0.21 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.195 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.019 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	21.0	Rigid Bonds:	66.0
TPSA:	494.88 ? Topological Polar Surface Area.	H-Bond Acceptor:	32.0
H-Bond Donor:	16.0	Rings:	11.0
Heavy Atoms:	32.0

MedChem Properties

QED Drug-Likeness Score:	0.03	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	7.876	Fsp³:	0.814
MCE-18:	322.654 ? 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:	0.804	Fluc inhibitor:	0.421 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.111 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.125 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.114	Promiscuous compounds:	0.176

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.677	MDCK Permeability:	-5.206
Pgp-inhibitor:	0.0	Pgp-substrate:	0.105
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):	0.953
20% Bioavailability (F20%):	0.711	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.038
Plasma Protein Binding (PPB):	71.813%	Volume Distribution (VD):	-0.328
Fu:	16.638% ? 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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.972
HLM stability:	0.007 ? 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):

-0.81

Half-life (T1/2):

4.238

ADMET: Toxicity

hERG Blockers:	0.0	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.751	Drug-induced Liver Injury (DILI):	0.916
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.006	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.888	Drug-induced Nephrotoxicity:	1.0
Genotoxicity:	0.225	RPMI-8226 Immunitoxicity:	0.536
A549 Cytotoxicity:	0.999	Hek293 Cytotoxicity:	0.8
BCF:	0.327 ? 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:	3.537 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.604 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.406 ? 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
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO27808	Cremanthodium discoideum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10579856]
NPO27081	Clavularia inflata	Species	Clavulariidae	Eukaryota	n.a.	Formosan soft coral	n.a.	PMID[11520220]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO28028	Aquilegia atrata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28102	Baccharis tucumanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28491	Astrotrichilia voamatata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28491	Astrotrichilia voamatata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27081	Clavularia inflata	Species	Clavulariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28102	Baccharis tucumanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27622	Ligularia cyathiceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28261	Pyrophorus pellucens	Species	Elateridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28154	Acrodontium salmoneum	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28312	Lentinus squarrosulus	Species	Lentinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28476	Doris tricolor	Species	Dorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28491	Astrotrichilia voamatata	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28081	Actinoplanes arizonaensis	Species	Micromonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO27846	Aeodes ulvoidea	Species	Halymeniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20099	Petalostylis labicheoides	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27934	Mezilaurus synandra	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28521	Delphinium vestitum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28210	Myrmecia gulosa	Species	Formicidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27808	Cremanthodium discoideum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8672	Ophiura ophiura	Species	Ophiuridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17149	Heracleum candicans	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29361	Chondrus yendoi	Species	Gigartinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3513	Fuscoporia senex	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28028	Aquilegia atrata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19588	Piper coruscans	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC313175 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	14363
0.1-0.2	30935
0.2-0.3	3669
0.3-0.4	731
0.4-0.5	142
0.5-0.6	13
0.6-0.7	4
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	Natural Product ID
0.6667	Remote Similarity	NPC478823
0.6667	Remote Similarity	NPC478824
0.6133	Remote Similarity	NPC478825
0.6096	Remote Similarity	NPC484942
0.5935	Remote Similarity	NPC478822
0.5679	Remote Similarity	NPC124828
0.5533	Remote Similarity	NPC484943
0.527	Remote Similarity	NPC300419
0.5163	Remote Similarity	NPC487505
0.514	Remote Similarity	NPC469777
0.5114	Remote Similarity	NPC469774
0.5085	Remote Similarity	NPC469778
0.5084	Remote Similarity	NPC481324
0.5055	Remote Similarity	NPC469772
0.5029	Remote Similarity	NPC469775
0.5028	Remote Similarity	NPC32723
0.5028	Remote Similarity	NPC100925

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC313175 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4952
0.1-0.2	4151
0.2-0.3	46
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