NPASS Compound

Natural Product: NPC292499

Natural Product ID	NPC292499
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	MBWUSSKCCUMJHO-LLEQCTEASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	53231635
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal 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 3D 134142 0 0 0 0 0 0 0 0999 V2000 12.7812 0.6966 0.8670 C 0 0 0 0 0 0 0 0 0 0 0 0 11.4068 0.5217 0.3035 C 0 0 2 0 0 0 0 0 0 0 0 0 10.4124 0.1672 1.3769 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5407 -0.9913 0.9882 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9626 -0.7101 -0.3635 C 0 0 2 0 0 0 0 0 0 0 0 0 8.0004 0.4923 -0.3097 C 0 0 1 0 0 0 0 0 0 0 0 0 8.4200 1.4946 -1.3944 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7510 -0.1136 -0.7058 C 0 0 1 0 0 0 0 0 0 0 0 0 6.9992 -1.5750 -0.2467 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7644 -2.2113 -0.7243 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7540 -1.1152 -0.6478 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4811 -1.3850 0.0196 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7286 -2.4935 -0.6721 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2575 -2.3740 -0.5486 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6265 -1.4331 0.1199 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8530 -1.4489 0.1504 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4685 -0.1628 0.5489 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6614 0.5631 1.6226 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6767 0.8779 1.0321 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4255 -0.3929 0.8135 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9060 -0.8752 2.1891 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6160 -0.1464 -0.0960 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2906 1.1232 0.2149 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6687 1.2761 -0.3480 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4861 0.0803 -0.0026 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6264 -0.0818 1.4812 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7558 -0.2741 1.1050 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6750 0.5472 0.5119 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8012 -0.2179 -0.0937 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7187 0.8239 -0.7111 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.3400 1.5395 0.4904 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3728 1.7512 1.5986 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7701 1.0036 2.8836 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1144 1.1689 3.1158 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0531 1.6112 1.3221 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9590 2.7079 0.0954 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3326 2.6678 0.3003 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8202 3.7901 1.1727 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.5329 5.1441 0.5870 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.8445 5.2014 -0.8827 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.4054 3.9118 -1.5701 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.8414 3.9999 -3.0184 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9467 2.7923 -0.9422 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1136 6.2412 -1.4647 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3395 6.0799 1.2406 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2014 3.6611 1.3067 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6577 0.2175 -1.4849 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2868 -1.1398 -0.9935 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6503 -2.4548 -0.7099 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1642 -3.1278 -1.9341 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.4473 -4.5963 -1.6321 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1073 -5.2184 -1.3187 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0803 -4.1749 -0.9349 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0417 -4.9201 -0.0864 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5590 -3.1561 -0.1600 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6298 -5.8700 -2.4562 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3386 -4.6864 -0.5592 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2333 -2.5177 -2.5275 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1784 -1.7933 -0.8393 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0095 -0.5180 -1.3174 N 0 0 0 0 0 0 0 0 0 0 0 0 11.3282 -0.5428 -0.7589 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7804 0.4755 1.9655 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5483 0.0475 0.3947 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1462 1.7593 0.7931 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1199 1.5039 -0.1652 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0011 -0.1715 2.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8290 1.0375 1.7125 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1049 -1.9269 0.9468 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7736 -1.1036 1.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0665 1.0187 0.6337 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0175 2.3119 -0.9951 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8512 0.9893 -2.2667 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4586 1.9471 -1.7571 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6340 -0.1855 -1.8054 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0396 -1.6370 0.8540 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8672 -2.6174 -1.7738 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4426 -3.0966 -0.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5394 -0.7685 -1.6988 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6040 -1.7169 1.0764 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0095 -3.4832 -0.2071 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9889 -2.5927 -1.7459 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6792 -3.1356 -1.0611 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2869 -1.7706 -0.8324 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2107 -2.2306 0.8873 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5330 0.5672 -0.2833 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1908 1.5178 1.8192 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6681 -0.0769 2.4994 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5204 1.4319 0.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2745 1.5013 1.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2373 -0.5305 3.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9591 -1.9624 2.2531 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8881 -0.3656 2.4180 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2375 -0.1276 -1.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2469 1.3092 1.3137 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6694 1.9556 -0.2293 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5816 1.3844 -1.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1334 2.1780 0.1058 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0245 0.6631 2.0594 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6846 0.1149 1.8275 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3651 -1.0643 1.8676 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1193 1.0570 -0.3393 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3773 -0.8178 0.6484 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1172 1.5233 -1.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1228 0.8368 0.8764 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4965 2.8436 1.9125 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2471 1.4853 3.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4085 -0.0376 2.8920 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3124 1.8996 3.7525 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6718 1.7102 0.7383 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3899 3.7607 2.1945 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4651 5.3895 0.7678 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9204 5.4177 -1.0621 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2972 3.9175 -1.5715 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1049 3.4658 -3.6364 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7867 5.0725 -3.3093 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8844 3.6593 -3.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8088 6.8566 -0.7356 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5655 5.7258 2.1538 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6607 3.5857 0.4489 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5796 0.4304 -2.4417 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3814 -2.4228 0.1320 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2910 -3.1676 -2.6570 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9173 -5.0181 -2.5455 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2627 -5.9164 -0.4676 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5439 -3.7526 -1.8175 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5126 -4.9827 0.9332 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9833 -5.9525 -0.4789 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0718 -4.4193 -0.0681 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9625 -5.3160 -2.9251 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7818 -3.8213 -0.3567 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0235 -2.5962 -1.9698 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9700 -1.1887 -2.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6409 -1.5097 -0.3526 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0416 -0.3038 -1.5891 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 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 1 17 27 1 0 27 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 32 35 1 0 31 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 40 44 1 0 39 45 1 0 38 46 1 0 30 47 1 0 29 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 53 55 1 0 52 56 1 0 51 57 1 0 50 58 1 0 9 59 1 0 5 60 1 0 60 61 1 0 61 2 1 0 5 59 1 6 25 8 1 0 35 28 1 0 43 37 1 0 55 49 1 0 25 11 1 0 22 12 1 0 20 15 1 0 1 62 1 0 1 63 1 0 1 64 1 0 2 65 1 6 3 66 1 0 3 67 1 0 4 68 1 0 4 69 1 0 6 70 1 1 7 71 1 0 7 72 1 0 7 73 1 0 8 74 1 6 9 75 1 1 10 76 1 0 10 77 1 0 11 78 1 6 12 79 1 1 13 80 1 0 13 81 1 0 14 82 1 0 16 83 1 0 16 84 1 0 17 85 1 6 18 86 1 0 18 87 1 0 19 88 1 0 19 89 1 0 21 90 1 0 21 91 1 0 21 92 1 0 22 93 1 6 23 94 1 0 23 95 1 0 24 96 1 0 24 97 1 0 26 98 1 0 26 99 1 0 26100 1 0 28101 1 6 29102 1 1 30103 1 6 31104 1 1 32105 1 1 33106 1 0 33107 1 0 34108 1 0 37109 1 1 38110 1 1 39111 1 6 40112 1 1 41113 1 6 42114 1 0 42115 1 0 42116 1 0 44117 1 0 45118 1 0 46119 1 0 47120 1 0 49121 1 1 50122 1 6 51123 1 6 52124 1 1 53125 1 6 54126 1 0 54127 1 0 54128 1 0 56129 1 0 57130 1 0 58131 1 0 60132 1 0 61133 1 0 61134 1 0 M END

Standard InCHIKey	MBWUSSKCCUMJHO-LLEQCTEASA-N
Standard InCHI	InChI=1S/C45H73NO15/c1-19-9-14-45(46-17-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(53)34(51)32(49)22(4)56-41)37(54)38(29(18-47)58-42)59-40-35(52)33(50)31(48)21(3)55-40/h7,19-22,24-42,46-54H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28-,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1
SMILES	C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@@H](C[C@H]4[C@@H]5CC=C6C[C@H](CC[C@]6(C)[C@H]5CC[C@]34C)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)O)O[C@H]3[C@@H]([C@@H]([C@H]([C@H](C)O3)O)O)O)O2)NC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	867.5	Volume:	850.081 ? Van der Waals volume.
Dense:	1.02	LogP:	1.848 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.625 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.177 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	48.0
TPSA:	238.48 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	9.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.161	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.751	Fsp³:	0.956
MCE-18:	229.091 ? 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:	0.889	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? 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:	0.012	Promiscuous compounds:	0.022

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.207	MDCK Permeability:	-5.066
Pgp-inhibitor:	0.0	Pgp-substrate:	0.93
PAMPA:	0.996 ? 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%):	0.008	30% Bioavailability (F30%):	0.422
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.035
Plasma Protein Binding (PPB):	63.869%	Volume Distribution (VD):	-0.382
Fu:	28.876% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.161
BSEP inhibitor:	0.011

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:	0.919	CYP3A4-substrate:	0.996
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.465
HLM stability:	0.775 ? 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):

0.269

Half-life (T1/2):

2.933

ADMET: Toxicity

hERG Blockers:	0.055	hERG Blockers (10um):	0.21
Human Hepatotoxicity (H-HT):	0.365	Drug-induced Liver Injury (DILI):	0.814
AMES Toxicity:	0.892	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	1.0
Carcinogencity:	0.023	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.997
Hematotoxicity:	0.159	Drug-induced Nephrotoxicity:	0.561
Genotoxicity:	0.025	RPMI-8226 Immunitoxicity:	0.322
A549 Cytotoxicity:	0.803	Hek293 Cytotoxicity:	0.706
BCF:	1.839 ? 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:	3.447 ? 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:	4.032 ? 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
NPO8353	Nephroma laevigatum	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15246	Eremosparton flaccidum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13157	Watsonia pyramidata	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14666	Ceratopetalum apetalum	Species	Cunoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8353	Nephroma laevigatum	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14758	Andropogon iwarancusa	Species	Poaceae	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 NPC292499 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	24707
0.1-0.2	22143
0.2-0.3	2466
0.3-0.4	424
0.4-0.5	47
0.5-0.6	34
0.6-0.7	29
0.7-0.8	1
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC122819
0.8889	High Similarity	NPC287885
0.8478	Intermediate Similarity	NPC15249
0.8478	Intermediate Similarity	NPC25455
0.798	Intermediate Similarity	NPC150057
0.798	Intermediate Similarity	NPC147753
0.7	Intermediate Similarity	NPC94272
0.6827	Remote Similarity	NPC470433
0.6827	Remote Similarity	NPC46190
0.6827	Remote Similarity	NPC171073
0.6762	Remote Similarity	NPC248746
0.6729	Remote Similarity	NPC73243
0.6729	Remote Similarity	NPC244086
0.6729	Remote Similarity	NPC84956
0.6698	Remote Similarity	NPC42171
0.6636	Remote Similarity	NPC480555
0.6636	Remote Similarity	NPC150372
0.6606	Remote Similarity	NPC247037
0.6495	Remote Similarity	NPC165439
0.6455	Remote Similarity	NPC269297
0.6455	Remote Similarity	NPC222202
0.6429	Remote Similarity	NPC249265
0.6429	Remote Similarity	NPC480554
0.6396	Remote Similarity	NPC475333
0.6396	Remote Similarity	NPC224098
0.6396	Remote Similarity	NPC208383
0.6372	Remote Similarity	NPC23808
0.6372	Remote Similarity	NPC87998
0.6339	Remote Similarity	NPC194207
0.6339	Remote Similarity	NPC22779
0.633	Remote Similarity	NPC475182
0.6316	Remote Similarity	NPC480553
0.6068	Remote Similarity	NPC232054
0.6055	Remote Similarity	NPC265275
0.605	Remote Similarity	NPC480556
0.6	Remote Similarity	NPC224314
0.5983	Remote Similarity	NPC308140
0.5957	Remote Similarity	NPC485606
0.5745	Remote Similarity	NPC147835
0.5745	Remote Similarity	NPC253645
0.5745	Remote Similarity	NPC85001
0.5745	Remote Similarity	NPC95920
0.5741	Remote Similarity	NPC470432
0.5741	Remote Similarity	NPC230507
0.5739	Remote Similarity	NPC486386
0.5676	Remote Similarity	NPC98696
0.5664	Remote Similarity	NPC124677
0.5641	Remote Similarity	NPC254255
0.5636	Remote Similarity	NPC305423
0.5636	Remote Similarity	NPC113044
0.5636	Remote Similarity	NPC283829
0.5636	Remote Similarity	NPC161676
0.5565	Remote Similarity	NPC102016
0.5565	Remote Similarity	NPC95051
0.5556	Remote Similarity	NPC32361
0.5526	Remote Similarity	NPC6806
0.5487	Remote Similarity	NPC602423
0.5437	Remote Similarity	NPC486114
0.5424	Remote Similarity	NPC13193
0.5391	Remote Similarity	NPC300557
0.5333	Remote Similarity	NPC218571
0.5333	Remote Similarity	NPC487615
0.5304	Remote Similarity	NPC477809
0.5221	Remote Similarity	NPC14704
0.5182	Remote Similarity	NPC19400
0.5167	Remote Similarity	NPC309278
0.5083	Remote Similarity	NPC475550
0.5078	Remote Similarity	NPC477808
0.5044	Remote Similarity	NPC485595
0.5044	Remote Similarity	NPC6295

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC292499 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7625
0.1-0.2	1461
0.2-0.3	57
0.3-0.4	5
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8449	Approved
0.798	Intermediate Similarity	NPD8450	Suspended

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