NPASS Compound

Natural Product: NPC511216

Natural Product ID	NPC511216
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Asparagoside D
IUPAC Name	(2~{R},3~{S},4~{R},5~{R},6~{S})-2-[(2~{R},3~{R},4~{R},5~{R},6~{R})-5-hydroxy-2-(hydroxymethyl)-6-[(1~{R},2~{S},4~{S},5'~{S},6~{R},7~{S},8~{R},9~{S},12~{S},13~{S},16~{S},18~{R})-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane-6,2'-tetrahydropyran]-16-yl]oxy-4-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 137145 0 0 0 0 0 0 0 0999 V2000 12.3708 -0.4409 0.7090 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6243 0.7923 1.1951 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2779 1.7409 0.0900 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8598 2.2125 0.2494 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8641 1.1182 0.4807 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3328 0.0584 1.2248 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4177 0.4007 2.0273 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7323 1.7138 1.0937 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7128 0.8018 0.9456 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3412 1.4670 0.7421 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7384 0.5083 -0.2047 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4493 0.8347 -0.8411 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3565 1.1408 0.1606 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1857 1.6278 -0.6581 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8232 0.7744 -1.8105 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6419 0.3773 -1.6647 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8506 -0.4809 -0.4127 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1443 -0.9357 -0.4051 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9116 -0.4032 0.6302 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3783 -1.4289 1.4359 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2575 -0.9890 2.4147 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5708 -2.0693 3.4223 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3532 -2.4352 4.0098 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5132 -0.3840 1.8034 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6951 0.8576 2.3245 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8041 1.0414 3.1209 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.5718 1.3143 4.4337 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1889 2.5902 4.7232 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7020 2.8562 4.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1876 2.6185 3.4249 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9914 3.6724 4.0890 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1200 4.0199 4.8297 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3913 3.3840 2.6856 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2787 3.5811 1.8693 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8521 1.9244 2.5331 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0221 1.8159 3.2779 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4045 -0.3726 0.2889 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3129 -1.6010 -0.2679 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1368 -1.9433 -1.3004 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.8753 -3.0475 -0.8690 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9362 -3.3566 -1.6697 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0723 -4.8868 -1.6432 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3000 -5.3491 -0.3446 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8066 -2.9499 -3.0933 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5299 -1.7385 -3.2283 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4349 -2.6939 -3.5956 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.0139 -3.8058 -4.3426 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3976 -2.4302 -2.5300 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4966 -1.5245 -3.0255 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0543 0.3196 0.0095 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0738 1.6240 0.5002 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1461 -1.6007 -0.3548 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9643 -1.7370 -1.5962 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6331 -0.4493 -2.0571 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6703 -0.6122 -3.5986 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0367 -0.4318 -1.5636 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0439 -0.8114 -2.6261 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4538 -0.7231 -2.1946 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8157 0.3875 -1.2627 C 0 0 1 0 0 0 0 0 0 0 0 0 6.1249 1.6754 -1.9423 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9810 0.0364 -0.3597 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3059 0.5320 -0.8173 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1285 -0.6883 -1.2522 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5119 -0.3645 -0.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 13.3709 -0.5449 1.1773 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7665 -1.3691 0.8785 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3297 1.3168 1.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9168 2.6700 0.1407 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4615 1.3352 -0.9266 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5045 2.8301 -0.6057 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8509 2.8478 1.1790 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1721 1.1937 2.7658 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6942 -0.4911 2.6124 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6583 0.0559 1.7696 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4598 2.4669 0.3296 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8352 1.4466 1.7430 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6491 -0.5037 0.2537 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4418 1.6399 -1.5763 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1067 0.3047 0.8089 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6820 1.9952 0.8206 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3551 1.9197 0.0172 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5380 2.6289 -1.0648 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8289 1.3864 -2.7672 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0296 -0.1289 -2.5670 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2003 1.3314 -1.5677 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6292 0.2142 0.4294 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2535 0.2955 1.1733 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7421 -0.1760 2.9604 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0228 -2.9657 2.9554 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2410 -1.6172 4.1869 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4953 -2.9084 4.8535 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3371 -1.0379 2.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2907 -0.0003 3.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4239 2.6961 5.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5865 3.9481 4.9331 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1735 2.3252 5.4962 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6627 3.3822 3.1346 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3545 4.6035 4.0662 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3878 4.9268 4.4913 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1982 4.0396 2.3335 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2680 4.4659 1.4442 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0157 1.7928 1.4589 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9357 1.3598 4.1274 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1578 0.3192 -0.1286 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8482 -1.1906 -1.6336 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9189 -3.0024 -1.2352 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8350 -5.2314 -2.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0923 -5.2826 -1.9867 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4117 -5.4663 0.0776 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3514 -3.6542 -3.7899 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4212 -1.8772 -2.7806 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4359 -1.8505 -4.3527 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5857 -4.5807 -4.2154 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9085 -3.4023 -2.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8684 -1.0752 -3.8187 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9199 0.4280 -1.0947 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7843 2.2982 -0.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4597 -2.5590 -0.2988 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7534 -1.6331 0.5698 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7492 -2.4982 -1.3985 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3073 -2.1843 -2.3820 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1481 -1.5357 -3.9103 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5772 -0.7285 -3.8653 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9874 0.3074 -4.0943 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1628 -1.2362 -0.7728 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8764 -0.1523 -3.4947 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8438 -1.8999 -2.8559 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7810 -1.6856 -1.6990 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1001 -0.6415 -3.0921 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6882 2.3731 -1.2907 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7061 1.4298 -2.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2440 2.2392 -2.3044 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9706 -1.0612 -0.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3216 1.2201 -1.6547 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2563 -1.3815 -0.4123 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0422 -0.3978 -1.7799 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4781 -1.2172 -2.0040 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 1 6 7 1 0 5 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 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 28 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 24 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 41 44 1 0 44 45 1 0 44 46 1 0 46 47 1 0 46 48 1 0 48 49 1 0 37 50 1 0 50 51 1 0 17 52 1 0 52 53 1 0 53 54 1 0 54 55 1 6 54 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 59 60 1 6 59 61 1 0 61 62 1 0 62 63 1 0 7 2 1 0 61 9 1 0 62 5 1 0 59 11 1 0 56 12 1 0 54 15 1 0 50 19 1 0 35 26 1 0 48 39 1 0 1 64 1 0 1 65 1 0 1 66 1 0 2 67 1 1 3 68 1 0 3 69 1 0 4 70 1 0 4 71 1 0 7 72 1 0 7 73 1 0 9 74 1 1 10 75 1 0 10 76 1 0 11 77 1 1 12 78 1 6 13 79 1 0 13 80 1 0 14 81 1 0 14 82 1 0 15 83 1 6 16 84 1 0 16 85 1 0 17 86 1 1 19 87 1 1 21 88 1 1 22 89 1 0 22 90 1 0 23 91 1 0 24 92 1 6 26 93 1 1 28 94 1 1 29 95 1 0 29 96 1 0 30 97 1 0 31 98 1 6 32 99 1 0 33100 1 6 34101 1 0 35102 1 6 36103 1 0 37104 1 6 39105 1 6 41106 1 1 42107 1 0 42108 1 0 43109 1 0 44110 1 6 45111 1 0 46112 1 6 47113 1 0 48114 1 1 49115 1 0 50116 1 6 51117 1 0 52118 1 0 52119 1 0 53120 1 0 53121 1 0 55122 1 0 55123 1 0 55124 1 0 56125 1 1 57126 1 0 57127 1 0 58128 1 0 58129 1 0 60130 1 0 60131 1 0 60132 1 0 61133 1 1 62134 1 6 63135 1 0 63136 1 0 63137 1 0 M END

Standard InCHIKey	DEXBUPZUMRUNGB-RWWRVRGXSA-N
Standard InCHI	InChI=1S/C45H74O18/c1-19-7-12-45(56-18-19)20(2)30-26(63-45)14-25-23-6-5-21-13-22(8-10-43(21,3)24(23)9-11-44(25,30)4)57-42-37(55)39(62-41-36(54)34(52)32(50)28(16-47)59-41)38(29(17-48)60-42)61-40-35(53)33(51)31(49)27(15-46)58-40/h19-42,46-55H,5-18H2,1-4H3/t19-,20-,21+,22-,23+,24-,25-,26-,27-,28+,29+,30-,31-,32+,33+,34-,35-,36+,37+,38+,39+,40+,41-,42+,43-,44-,45+/m0/s1
SMILES	C[C@H]1CC[C@@]2(OC1)O[C@H]1C[C@H]3[C@@H]4CC[C@@H]5C[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O[C@H]7O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]7O)[C@H](O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O)[C@H]6O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	902.49	Volume:	868.092 ? Van der Waals volume.
Dense:	1.04	LogP:	1.549 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.446 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.463 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	48.0
TPSA:	276.14 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	10.0	Rings:	9.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.128	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.689	Fsp³:	1.0
MCE-18:	230.667 ? 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:	0.775	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.018 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.305	Promiscuous compounds:	0.01

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.834	MDCK Permeability:	-4.813
Pgp-inhibitor:	0.0	Pgp-substrate:	0.328
PAMPA:	0.993 ? 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):	0.002
20% Bioavailability (F20%):	0.02	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013	MRP1:	0.003
Plasma Protein Binding (PPB):	58.703%	Volume Distribution (VD):	-0.376
Fu:	31.533% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.119
BSEP inhibitor:	0.027

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.002	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.999	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.528
HLM stability:	0.021 ? 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):

-0.024

Half-life (T1/2):

3.157

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.031
Human Hepatotoxicity (H-HT):	0.589	Drug-induced Liver Injury (DILI):	0.974
AMES Toxicity:	0.876	Rat Oral Acute Toxicity:	0.002
Maximum Recommended Daily Dose:	0.002	Skin Sensitization:	1.0
Carcinogencity:	0.082	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.999
Hematotoxicity:	0.148	Drug-induced Nephrotoxicity:	0.918
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.208
A549 Cytotoxicity:	0.637	Hek293 Cytotoxicity:	0.628
BCF:	1.61 ? 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:	3.427 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.603 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.958 ? 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
NPO47249	Asparagus officinalis L.	Genus	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO54874	Asparagus tenuifolius Lam.	Genus	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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 NPC511216 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	25885
0.1-0.2	20557
0.2-0.3	2762
0.3-0.4	361
0.4-0.5	157
0.5-0.6	86
0.6-0.7	29
0.7-0.8	1
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
0.8537	High Similarity	NPC325828
0.8	Intermediate Similarity	NPC234352
0.7865	Intermediate Similarity	NPC107962
0.7674	Intermediate Similarity	NPC297348
0.7674	Intermediate Similarity	NPC249204
0.7674	Intermediate Similarity	NPC48339
0.7674	Intermediate Similarity	NPC141769
0.7674	Intermediate Similarity	NPC477547
0.764	Intermediate Similarity	NPC107188
0.7528	Intermediate Similarity	NPC206003
0.7528	Intermediate Similarity	NPC473610
0.7423	Intermediate Similarity	NPC184617
0.7416	Intermediate Similarity	NPC250393
0.7391	Intermediate Similarity	NPC6295
0.7303	Intermediate Similarity	NPC477451
0.7253	Intermediate Similarity	NPC211354
0.7071	Intermediate Similarity	NPC97700
0.7071	Intermediate Similarity	NPC30856
0.7065	Intermediate Similarity	NPC19400
0.7053	Intermediate Similarity	NPC160426
0.6979	Remote Similarity	NPC475351
0.6923	Remote Similarity	NPC132080
0.6889	Remote Similarity	NPC177834
0.6854	Remote Similarity	NPC485594
0.6699	Remote Similarity	NPC475625
0.6667	Remote Similarity	NPC125324
0.6635	Remote Similarity	NPC232037
0.6634	Remote Similarity	NPC128572
0.66	Remote Similarity	NPC92890
0.6593	Remote Similarity	NPC181845
0.6571	Remote Similarity	NPC470864
0.6452	Remote Similarity	NPC294686
0.6381	Remote Similarity	NPC116756
0.6337	Remote Similarity	NPC475643
0.6327	Remote Similarity	NPC470432
0.6327	Remote Similarity	NPC230507
0.6275	Remote Similarity	NPC477809
0.6273	Remote Similarity	NPC470866
0.6264	Remote Similarity	NPC24960
0.6263	Remote Similarity	NPC195297
0.6214	Remote Similarity	NPC51172
0.6214	Remote Similarity	NPC49032
0.6162	Remote Similarity	NPC485595
0.6146	Remote Similarity	NPC222731
0.6058	Remote Similarity	NPC471464
0.604	Remote Similarity	NPC14704
0.6	Remote Similarity	NPC480555
0.6	Remote Similarity	NPC233433
0.6	Remote Similarity	NPC150372
0.596	Remote Similarity	NPC264101
0.5934	Remote Similarity	NPC277715
0.5922	Remote Similarity	NPC473601
0.5913	Remote Similarity	NPC220836
0.5909	Remote Similarity	NPC83137
0.5905	Remote Similarity	NPC300557
0.5905	Remote Similarity	NPC6806
0.5888	Remote Similarity	NPC115165
0.5888	Remote Similarity	NPC475319
0.5882	Remote Similarity	NPC113044
0.5882	Remote Similarity	NPC283829
0.5882	Remote Similarity	NPC161676
0.5856	Remote Similarity	NPC480553
0.5856	Remote Similarity	NPC477811
0.5766	Remote Similarity	NPC476112
0.5766	Remote Similarity	NPC307534
0.5758	Remote Similarity	NPC121453
0.5743	Remote Similarity	NPC215408
0.5714	Remote Similarity	NPC470433
0.5714	Remote Similarity	NPC46190
0.5714	Remote Similarity	NPC171073
0.5714	Remote Similarity	NPC602423
0.57	Remote Similarity	NPC54619
0.5676	Remote Similarity	NPC480554
0.5652	Remote Similarity	NPC94086
0.5652	Remote Similarity	NPC473817
0.5638	Remote Similarity	NPC473774
0.5638	Remote Similarity	NPC481419
0.5638	Remote Similarity	NPC481417
0.5591	Remote Similarity	NPC481189
0.55	Remote Similarity	NPC474399
0.5487	Remote Similarity	NPC470862
0.5481	Remote Similarity	NPC141433
0.5476	Remote Similarity	NPC329807
0.5472	Remote Similarity	NPC202898
0.5405	Remote Similarity	NPC269297
0.5405	Remote Similarity	NPC222202
0.5405	Remote Similarity	NPC475550
0.5403	Remote Similarity	NPC481190
0.5357	Remote Similarity	NPC475333
0.5357	Remote Similarity	NPC473518
0.5357	Remote Similarity	NPC224098
0.5357	Remote Similarity	NPC208383
0.5339	Remote Similarity	NPC480556
0.5319	Remote Similarity	NPC144790
0.5319	Remote Similarity	NPC149400
0.5312	Remote Similarity	NPC481420
0.5312	Remote Similarity	NPC481421
0.531	Remote Similarity	NPC194207
0.531	Remote Similarity	NPC22779
0.531	Remote Similarity	NPC232611
0.5308	Remote Similarity	NPC329727
0.53	Remote Similarity	NPC291203
0.53	Remote Similarity	NPC217205
0.5294	Remote Similarity	NPC479353
0.5294	Remote Similarity	NPC248944
0.5294	Remote Similarity	NPC7479
0.5294	Remote Similarity	NPC257296
0.5294	Remote Similarity	NPC479354
0.5294	Remote Similarity	NPC477807
0.5273	Remote Similarity	NPC151134
0.5268	Remote Similarity	NPC470863
0.5263	Remote Similarity	NPC108072
0.5259	Remote Similarity	NPC31896
0.525	Remote Similarity	NPC477808
0.5243	Remote Similarity	NPC306131
0.5243	Remote Similarity	NPC200802
0.5238	Remote Similarity	NPC330026
0.5229	Remote Similarity	NPC248746
0.5221	Remote Similarity	NPC309278
0.5207	Remote Similarity	NPC210569
0.5149	Remote Similarity	NPC131693
0.5149	Remote Similarity	NPC475436
0.5146	Remote Similarity	NPC128123
0.5089	Remote Similarity	NPC98018
0.5089	Remote Similarity	NPC284104
0.5089	Remote Similarity	NPC103616
0.5088	Remote Similarity	NPC32361
0.5085	Remote Similarity	NPC232054
0.5047	Remote Similarity	NPC70204
0.5045	Remote Similarity	NPC249553
0.5043	Remote Similarity	NPC84111
0.5043	Remote Similarity	NPC287483
0.5043	Remote Similarity	NPC470865
0.5042	Remote Similarity	NPC470867
0.5041	Remote Similarity	NPC224314

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC511216 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7724
0.1-0.2	1326
0.2-0.3	82
0.3-0.4	13
0.4-0.5	1
0.5-0.6	2
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8537	High Similarity	NPD8171	Phase 2
0.7391	Intermediate Similarity	NPD8170	Phase 2
0.5294	Remote Similarity	NPD6928	Phase 2
0.5208	Remote Similarity	NPD7991	Discontinued

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