NPASS Compound

Natural Product: NPC255569

Natural Product ID	NPC255569
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FAGJLZBHFXTNAB-BXXHXKGSSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

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 140148 0 0 0 0 0 0 0 0999 V2000 0.9037 1.8957 -1.4053 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1677 0.8060 -0.6566 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1036 -0.3655 -0.5085 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3662 -1.5825 -1.0433 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9463 -1.7186 -0.2886 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7209 -0.4406 -0.5062 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0251 0.4523 -1.3190 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9989 -0.6992 -0.9258 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9847 -0.2513 -0.0143 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8051 0.7706 -0.7290 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9866 0.2109 -1.4399 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8377 -0.7422 -0.6806 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9153 -2.0205 -1.5646 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2263 -1.1905 0.5925 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.4057 -0.3062 1.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5494 0.6793 1.6541 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6279 -0.0578 0.8888 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.2237 -0.1791 -0.5383 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2816 -0.9858 -1.2473 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6286 -0.2954 -1.0815 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.0619 -0.1338 0.3234 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.2763 -1.4711 1.0059 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1801 0.8122 0.5335 C 0 0 2 0 0 0 0 0 0 0 0 0 -13.4603 0.5545 -0.1040 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.5614 0.2141 0.5892 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.6646 0.0295 -0.3517 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.1668 0.3362 -1.6136 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.8231 0.6403 -1.5137 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.0506 0.9433 -2.4958 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.5740 2.1696 0.2513 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.1033 1.9799 0.6529 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9540 0.5671 1.1070 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.2370 0.5139 2.4798 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2157 3.1042 1.0544 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7441 -1.4505 0.4308 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1227 -2.7261 -0.8422 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5183 -0.5619 0.7989 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9097 -0.5543 0.8955 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3981 0.5182 1.8168 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7585 0.2626 2.3523 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5429 -0.8296 1.7170 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7097 -1.8491 0.9868 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2275 -3.2302 1.1929 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3727 -1.7937 1.3958 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4423 -0.2780 0.8007 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7581 -0.6174 1.1189 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3468 -1.4429 0.0045 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9286 -0.6462 -1.1171 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6565 0.5948 -0.6259 C 0 0 1 0 0 0 0 0 0 0 0 0 8.7604 1.3371 0.3501 C 0 0 1 0 0 0 0 0 0 0 0 0 7.5686 1.9352 -0.3410 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4510 0.5270 1.4165 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7709 0.1686 0.0840 O 0 0 0 0 0 0 0 0 0 0 0 0 11.8996 0.7223 -0.5081 C 0 0 1 0 0 0 0 0 0 0 0 0 12.5594 1.5856 0.5694 C 0 0 1 0 0 0 0 0 0 0 0 0 14.0422 1.6662 0.2914 C 0 0 2 0 0 0 0 0 0 0 0 0 14.3081 1.4406 -1.1826 C 0 0 1 0 0 0 0 0 0 0 0 0 13.8132 0.0824 -1.6237 C 0 0 1 0 0 0 0 0 0 0 0 0 14.8744 -0.9668 -1.5865 C 0 0 0 0 0 0 0 0 0 0 0 0 14.3124 -2.1441 -2.1222 O 0 0 0 0 0 0 0 0 0 0 0 0 12.7284 -0.3432 -0.8594 O 0 0 0 0 0 0 0 0 0 0 0 0 13.7134 2.4371 -1.9507 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7264 0.6873 0.9995 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0192 2.8547 0.4822 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8989 -1.4164 -1.7781 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5199 1.4566 2.4268 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8596 2.8765 -0.8614 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5472 1.9890 -2.4463 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0030 1.6683 -1.4726 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0679 1.2124 0.3585 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0113 -0.2503 -1.1354 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1845 -1.4252 -2.1048 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7049 -1.8753 0.7756 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5517 -2.5612 -0.7004 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7859 0.0770 0.4955 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4235 0.2136 0.8251 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1651 1.5209 0.0156 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1648 1.3982 -1.4245 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6309 -0.1955 -2.4167 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6114 1.1074 -1.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4196 -2.8333 -1.0162 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2833 -1.8045 -2.5634 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8481 -2.3471 -1.7018 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6523 -2.2276 0.7946 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5625 -0.9779 2.6635 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4842 0.2601 1.9797 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9195 0.8871 2.6796 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2678 1.6261 1.1855 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6700 -1.0868 1.3336 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2641 0.8371 -1.0296 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2945 -2.0448 -0.9996 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0574 -0.8720 -2.3481 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3462 -0.9282 -1.6597 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.5292 0.6677 -1.5878 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1609 -1.3267 2.0844 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4678 -2.1385 0.6630 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.2309 -1.9398 0.7133 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3721 0.8447 1.6709 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.6694 0.0828 1.6708 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.0633 -1.0099 -0.2555 H 0 0 0 0 0 0 0 0 0 0 0 0 -16.4942 0.7012 -0.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5707 2.4205 -0.8162 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4105 2.2962 -0.1325 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9375 2.6776 1.5190 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1993 1.4384 2.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3415 3.9750 0.6376 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5208 -2.3594 -0.1640 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3795 -1.7116 1.4693 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0376 -2.6439 -1.1774 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3363 -0.3846 -0.1120 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4226 1.5117 1.2729 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6860 0.7084 2.6621 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6465 -0.0280 3.4424 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1397 -1.4000 2.4804 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7138 -1.5858 -0.0922 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8995 -3.3252 2.0717 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7218 -3.6181 0.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3798 -3.9164 1.3794 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7939 -1.2582 2.0297 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4899 -2.0441 -0.4222 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0747 -2.2058 0.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1672 -0.3628 -1.8512 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8738 1.2461 -1.4704 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3664 2.1838 0.7474 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9745 1.2053 -0.9262 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9732 2.6497 -1.1161 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9842 2.5496 0.3463 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6171 1.3415 -1.3648 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3462 1.1376 1.5628 H 0 0 0 0 0 0 0 0 0 0 0 0 14.4629 2.6668 0.5564 H 0 0 0 0 0 0 0 0 0 0 0 0 15.4015 1.4665 -1.3369 H 0 0 0 0 0 0 0 0 0 0 0 0 13.4479 0.1959 -2.6578 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2257 -1.1990 -0.5788 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7657 -0.6575 -2.1814 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8905 -2.6110 -1.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8899 3.3296 -1.5571 H 0 0 0 0 0 0 0 0 0 0 0 0 15.7033 0.9400 0.9679 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0905 3.3670 1.3426 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4225 -1.9362 -1.1187 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0094 2.1494 1.9284 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 6 12 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 1 21 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 2 0 23 30 1 0 30 31 1 0 31 32 1 0 32 33 1 1 30 34 1 0 14 35 1 0 4 36 1 0 3 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 42 44 1 0 41 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 50 52 1 0 49 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 1 0 59 60 1 0 58 61 1 0 57 62 1 0 56 63 1 0 55 64 1 0 48 65 1 0 40 66 1 0 7 2 1 0 35 9 1 0 44 38 1 0 52 46 1 0 61 54 1 0 18 12 1 0 32 21 1 0 32 17 1 0 28 24 1 0 1 67 1 0 1 68 1 0 1 69 1 0 2 70 1 1 3 71 1 6 4 72 1 6 5 73 1 0 5 74 1 0 6 75 1 1 9 76 1 1 10 77 1 0 10 78 1 0 11 79 1 0 11 80 1 0 13 81 1 0 13 82 1 0 13 83 1 0 14 84 1 1 15 85 1 0 15 86 1 0 16 87 1 0 16 88 1 0 17 89 1 1 18 90 1 6 19 91 1 0 19 92 1 0 20 93 1 0 20 94 1 0 22 95 1 0 22 96 1 0 22 97 1 0 23 98 1 1 25 99 1 0 26100 1 0 26101 1 0 30102 1 6 31103 1 0 31104 1 0 33105 1 0 34106 1 0 35107 1 0 35108 1 0 36109 1 0 38110 1 6 39111 1 0 39112 1 0 40113 1 1 41114 1 1 42115 1 6 43116 1 0 43117 1 0 43118 1 0 46119 1 1 47120 1 0 47121 1 0 48122 1 6 49123 1 6 50124 1 1 51125 1 0 51126 1 0 51127 1 0 54128 1 6 55129 1 1 56130 1 1 57131 1 1 58132 1 6 59133 1 0 59134 1 0 60135 1 0 62136 1 0 63137 1 0 64138 1 0 65139 1 0 66140 1 0 M END

Standard InCHIKey	FAGJLZBHFXTNAB-BXXHXKGSSA-N
Standard InCHI	InChI=1S/C47H74O19/c1-20-40(64-34-16-29(50)41(21(2)60-34)65-35-17-30(51)42(22(3)61-35)66-44-39(55)38(54)37(53)32(19-48)63-44)28(49)15-33(59-20)62-24-8-11-45(4)23(14-24)6-7-27-26(45)9-12-46(5)36(25-10-13-58-43(25)56)31(52)18-47(27,46)57/h10,20-24,26-42,44,48-55,57H,6-9,11-19H2,1-5H3/t20-,21-,22-,23-,24+,26+,27-,28+,29+,30+,31+,32-,33+,34+,35+,36-,37-,38+,39-,40-,41-,42-,44+,45+,46-,47+/m1/s1
SMILES	C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]1CC[C@@]2(C)[C@H](CC[C@@H]3[C@@H]2CC[C@]2(C)[C@H](C4=CCOC4=O)[C@H](C[C@]32O)O)C1)O)O[C@H]1C[C@@H]([C@@H]([C@@H](C)O1)O[C@H]1C[C@@H]([C@@H]([C@@H](C)O1)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:	942.48	Volume:	906.201 ? Van der Waals volume.
Dense:	1.04	LogP:	1.622 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.246 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.053 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	10.0	Rigid Bonds:	50.0
TPSA:	282.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	9.0	Rings:	9.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.103	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.601	Fsp³:	0.936
MCE-18:	172.945 ? 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:	0.678	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? 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:	0.366	Promiscuous compounds:	0.252

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.299	MDCK Permeability:	-4.987
Pgp-inhibitor:	0.011	Pgp-substrate:	0.921
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):	0.0
20% Bioavailability (F20%):	0.007	30% Bioavailability (F30%):	0.097
50% Bioavailability (F50%):	0.689

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.847
Plasma Protein Binding (PPB):	51.767%	Volume Distribution (VD):	-0.469
Fu:	38.272% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.964	BCRP inhibitor:	0.0
BSEP inhibitor:	0.498

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.001	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.373	CYP3A4-substrate:	0.791
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.823
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):

-0.165

Half-life (T1/2):

4.531

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.028
Human Hepatotoxicity (H-HT):	0.543	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.989	Rat Oral Acute Toxicity:	0.541
Maximum Recommended Daily Dose:	0.346	Skin Sensitization:	1.0
Carcinogencity:	0.302	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.067
Drug-induced Neurotoxicity:	0.002	Ototoxicity:	1.0
Hematotoxicity:	0.96	Drug-induced Nephrotoxicity:	0.997
Genotoxicity:	0.93	RPMI-8226 Immunitoxicity:	0.647
A549 Cytotoxicity:	0.998	Hek293 Cytotoxicity:	0.894
BCF:	0.579 ? 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:	3.234 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.623 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.727 ? 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
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	Flowers	n.a.	n.a.	DOI[10.1016/j.lwt.2014.11.023]
NPO12474	Cordyline fruticosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27168	Atropa belladona	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18180	Erysimum repandum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18930	Rubus coreanus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO27168	Atropa belladona	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19093	Streptomyces aburaviensis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19175	Iguana iguana	Species	Iguanidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19441	Strychnos splendens	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12474	Cordyline fruticosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13401	Phoenix canariensis	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19015	Begonia glabra	Species	Begoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18180	Erysimum repandum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17635	Aria arguta	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17774	Hemerocallis fulva	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1551	Luffa aegyptiaca	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18930	Rubus coreanus	Species	Rosaceae	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 NPC255569 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	19330
0.1-0.2	25893
0.2-0.3	3773
0.3-0.4	701
0.4-0.5	88
0.5-0.6	57
0.6-0.7	14
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
0.7158	Intermediate Similarity	NPC475219
0.701	Intermediate Similarity	NPC475590
0.6915	Remote Similarity	NPC208193
0.6889	Remote Similarity	NPC193893
0.6869	Remote Similarity	NPC120390
0.67	Remote Similarity	NPC74259
0.6632	Remote Similarity	NPC231518
0.6632	Remote Similarity	NPC488944
0.6562	Remote Similarity	NPC125077
0.6421	Remote Similarity	NPC236973
0.6264	Remote Similarity	NPC5311
0.6238	Remote Similarity	NPC479360
0.6238	Remote Similarity	NPC479359
0.6154	Remote Similarity	NPC117445
0.6154	Remote Similarity	NPC308262
0.6105	Remote Similarity	NPC72260
0.5918	Remote Similarity	NPC40749
0.59	Remote Similarity	NPC486143
0.59	Remote Similarity	NPC486142
0.59	Remote Similarity	NPC486149
0.5859	Remote Similarity	NPC475556
0.5859	Remote Similarity	NPC311706
0.5816	Remote Similarity	NPC30483
0.5816	Remote Similarity	NPC470897
0.5758	Remote Similarity	NPC292467
0.5755	Remote Similarity	NPC475419
0.5701	Remote Similarity	NPC474908
0.57	Remote Similarity	NPC479353
0.57	Remote Similarity	NPC479354
0.5688	Remote Similarity	NPC474423
0.5631	Remote Similarity	NPC486146
0.5619	Remote Similarity	NPC488943
0.5619	Remote Similarity	NPC488942
0.56	Remote Similarity	NPC32177
0.56	Remote Similarity	NPC469756
0.56	Remote Similarity	NPC275901
0.5588	Remote Similarity	NPC55532
0.5566	Remote Similarity	NPC486144
0.5566	Remote Similarity	NPC486145
0.5566	Remote Similarity	NPC486147
0.5566	Remote Similarity	NPC486148
0.5556	Remote Similarity	NPC173555
0.5545	Remote Similarity	NPC188234
0.5532	Remote Similarity	NPC99620
0.549	Remote Similarity	NPC488941
0.549	Remote Similarity	NPC488940
0.5472	Remote Similarity	NPC488938
0.5472	Remote Similarity	NPC488937
0.5417	Remote Similarity	NPC77299
0.5417	Remote Similarity	NPC480906
0.5417	Remote Similarity	NPC99080
0.5377	Remote Similarity	NPC479357
0.5368	Remote Similarity	NPC471633
0.5361	Remote Similarity	NPC480914
0.5333	Remote Similarity	NPC329986
0.5333	Remote Similarity	NPC140092
0.5333	Remote Similarity	NPC488939
0.5315	Remote Similarity	NPC488945
0.5315	Remote Similarity	NPC488946
0.5273	Remote Similarity	NPC486134
0.5273	Remote Similarity	NPC486141
0.5149	Remote Similarity	NPC480907
0.5143	Remote Similarity	NPC486135
0.5143	Remote Similarity	NPC486137
0.5135	Remote Similarity	NPC329675
0.5133	Remote Similarity	NPC488947
0.5102	Remote Similarity	NPC479356
0.5102	Remote Similarity	NPC479355
0.5096	Remote Similarity	NPC240070
0.5094	Remote Similarity	NPC232785
0.5094	Remote Similarity	NPC486139
0.5051	Remote Similarity	NPC76572
0.5051	Remote Similarity	NPC193382

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC255569 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6977
0.1-0.2	2079
0.2-0.3	74
0.3-0.4	10
0.4-0.5	2
0.5-0.6	6
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6632	Remote Similarity	NPD8033	Approved
0.6105	Remote Similarity	NPD8294	Phase 4
0.5588	Remote Similarity	NPD8377	Phase 4
0.5556	Remote Similarity	NPD8296	Phase 4
0.5464	Remote Similarity	NPD8335	Phase 4
0.5408	Remote Similarity	NPD8380	Approved
0.5094	Remote Similarity	NPD8378	Pre-clinical
0.5094	Remote Similarity	NPD8379	Approved

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