NPASS Compound

Natural Product: NPC531525

Natural Product ID	NPC531525
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Anguivioside A
IUPAC Name	(2~{S},3~{R},4~{R},5~{R},6~{S})-2-[(2~{R},3~{S},4~{S},5~{R},6~{R})-4-hydroxy-2-(hydroxymethyl)-6-[(1~{S},2~{S},4~{S},5'~{R},6~{S},6'~{R},7~{S},8~{R},9~{S},12~{S},13~{R},16~{S})-6'-hydroxy-5',7,9,13-tetramethyl-spiro[5-oxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icos-18-ene-6,2'-tetrahydropyran]-16-yl]oxy-5-[(2~{S},3~{R},4~{R},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl]oxy-6-methyl-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 134142 0 0 0 0 0 0 0 0999 V2000 13.0468 0.4154 -1.8965 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6738 -0.1282 -1.5787 C 0 0 2 0 0 0 0 0 0 0 0 0 11.0336 -0.7808 -2.7769 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6871 -1.3066 -2.3922 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8952 -0.3928 -1.5305 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6050 0.3860 -0.6515 O 0 0 0 0 0 0 0 0 0 0 0 0 10.7225 0.9988 -1.1571 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2750 1.8173 -0.1963 O 0 0 0 0 0 0 0 0 0 0 0 0 7.9474 0.3642 -2.2559 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1002 0.9050 -1.3018 C 0 0 1 0 0 0 0 0 0 0 0 0 5.6648 1.0300 -1.7755 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9394 0.8010 -0.4878 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4694 0.6009 -0.6031 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7770 1.7678 -1.2447 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3480 1.7615 -0.9192 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7231 1.0474 -0.0087 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7271 1.1990 0.1526 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3530 0.7249 1.3940 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4932 -0.0313 1.1497 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6540 0.4476 1.7155 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1959 -0.3621 2.6686 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9135 -1.4281 2.1927 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.0778 -2.2689 1.2949 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9670 -2.7352 1.9977 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1121 -0.9012 1.4042 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.2890 -1.4136 1.8328 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0665 -2.1213 0.9784 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.3775 -1.6793 0.8787 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.0414 -1.7063 2.0953 C 0 0 1 0 0 0 0 0 0 0 0 0 -11.4612 -1.2483 1.8657 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0664 -3.0379 2.7671 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.5295 -2.8089 4.0820 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6215 -3.5353 2.8982 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.6594 -4.7996 3.4460 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0706 -3.5784 1.4894 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.0270 -4.2422 0.7172 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0606 0.6393 1.4014 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.0852 1.1150 0.6285 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6962 0.9330 0.7747 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5607 2.2387 0.3831 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4411 2.4435 -0.9753 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.2421 3.1139 -1.1800 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9757 3.4603 -2.4765 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5454 2.2139 -3.2292 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1441 4.0759 -3.1766 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7270 5.1330 -3.9886 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1471 4.5322 -2.1598 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2488 5.1612 -2.7119 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6201 3.3101 -1.3810 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4171 2.5833 -2.2602 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5035 -0.1087 2.3164 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9577 0.2297 2.2313 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4755 0.1052 0.8173 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2315 -1.3444 0.3945 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9587 0.4007 0.8009 C 0 0 1 0 0 0 0 0 0 0 0 0 3.7160 -0.6007 1.6012 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1934 -0.5687 1.4648 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5979 -0.4530 0.0105 C 0 0 1 0 0 0 0 0 0 0 0 0 5.2269 -1.7017 -0.7049 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0463 -0.0855 -0.1530 C 0 0 1 0 0 0 0 0 0 0 0 0 7.9145 -1.2076 -0.6690 C 0 0 2 0 0 0 0 0 0 0 0 0 8.6510 -1.9099 0.4469 C 0 0 0 0 0 0 0 0 0 0 0 0 13.6355 -0.3605 -2.4147 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0167 1.3451 -2.4986 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5745 0.6534 -0.9511 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7647 -0.8313 -0.7321 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6527 -1.5941 -3.2020 H 0 0 0 0 0 0 0 0 0 0 0 0 10.8978 0.0327 -3.5469 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1082 -1.4384 -3.3536 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7656 -2.3460 -1.9849 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5253 1.6206 -2.0612 H 0 0 0 0 0 0 0 0 0 0 0 0 12.0800 1.4326 0.2481 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4995 1.8417 -0.8798 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5364 2.0477 -2.1805 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4539 0.2490 -2.5348 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1492 1.6210 0.1995 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2355 -0.2990 -1.2448 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2739 2.7368 -1.0125 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9283 1.6320 -2.3591 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6997 2.4488 -1.5161 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1746 0.7082 -0.7779 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9305 2.3146 0.0267 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6919 1.6182 2.0004 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3141 1.3811 2.2785 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2647 -1.9850 3.0967 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7343 -1.7975 0.3637 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6712 -3.1699 0.9343 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0839 -3.7082 2.1980 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9474 -1.1712 0.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6491 -2.1918 -0.0398 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5850 -0.9844 2.8285 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1145 -1.4592 2.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.4717 -0.1237 1.7553 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.8870 -1.6509 0.9331 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7173 -3.7864 2.3130 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1737 -3.4897 4.7038 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0942 -2.7855 3.5246 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.8329 -5.3035 3.2319 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0752 -4.0030 1.3947 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7971 -3.6482 0.4953 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0995 0.9229 2.4685 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9127 0.6123 0.6219 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6640 0.3166 -0.1462 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4625 1.5416 -1.5767 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1172 4.1683 -2.5307 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5101 1.9010 -2.9528 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4716 2.5297 -4.3103 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2691 1.4011 -3.2082 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6488 3.3409 -3.8445 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5392 5.5603 -4.3826 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6829 5.2172 -1.4126 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6988 4.5127 -3.2973 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2673 3.5899 -0.5246 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3864 2.7554 -2.1437 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6410 -1.2031 2.1867 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8266 0.0990 3.3554 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4863 -0.5615 2.8370 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1180 1.2056 2.6866 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1610 -1.4413 0.1027 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8133 -1.6296 -0.4812 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3602 -1.9643 1.2917 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0834 1.3980 1.3167 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5027 -0.3828 2.6903 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3644 -1.6444 1.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6027 -1.5193 1.8640 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5866 0.3214 2.0076 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8280 -2.5292 -0.2236 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1780 -1.9801 -0.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3547 -1.6637 -1.7947 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4925 0.3131 0.7785 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4091 -1.8885 -1.3639 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0683 -1.8853 1.3971 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8080 -2.9853 0.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6339 -1.4538 0.6627 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 7 8 1 0 5 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 2 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 23 24 1 0 22 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 29 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 25 37 1 0 37 38 1 0 37 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 43 45 1 0 45 46 1 0 45 47 1 0 47 48 1 0 47 49 1 0 49 50 1 0 18 51 1 0 51 52 1 0 52 53 1 0 53 54 1 6 53 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 6 58 60 1 0 60 61 1 0 61 62 1 0 7 2 1 0 60 10 1 0 61 5 1 0 58 12 1 0 55 13 1 0 53 16 1 0 39 20 1 0 49 41 1 0 35 27 1 0 1 63 1 0 1 64 1 0 1 65 1 0 2 66 1 1 3 67 1 0 3 68 1 0 4 69 1 0 4 70 1 0 7 71 1 6 8 72 1 0 10 73 1 1 11 74 1 0 11 75 1 0 12 76 1 1 13 77 1 6 14 78 1 0 14 79 1 0 15 80 1 0 17 81 1 0 17 82 1 0 18 83 1 1 20 84 1 1 22 85 1 1 23 86 1 0 23 87 1 0 24 88 1 0 25 89 1 6 27 90 1 6 29 91 1 1 30 92 1 0 30 93 1 0 30 94 1 0 31 95 1 6 32 96 1 0 33 97 1 1 34 98 1 0 35 99 1 1 36100 1 0 37101 1 1 38102 1 0 39103 1 6 41104 1 6 43105 1 1 44106 1 0 44107 1 0 44108 1 0 45109 1 6 46110 1 0 47111 1 1 48112 1 0 49113 1 1 50114 1 0 51115 1 0 51116 1 0 52117 1 0 52118 1 0 54119 1 0 54120 1 0 54121 1 0 55122 1 1 56123 1 0 56124 1 0 57125 1 0 57126 1 0 59127 1 0 59128 1 0 59129 1 0 60130 1 1 61131 1 6 62132 1 0 62133 1 0 62134 1 0 M END

Standard InCHIKey	LPZCNTXUCIGYQK-JAVAWAHBSA-N
Standard InCHI	InChI=1S/C45H72O17/c1-18-9-14-45(62-39(18)54)19(2)29-27(61-45)16-26-24-8-7-22-15-23(10-12-43(22,5)25(24)11-13-44(26,29)6)57-42-38(60-41-35(52)33(50)31(48)21(4)56-41)36(53)37(28(17-46)58-42)59-40-34(51)32(49)30(47)20(3)55-40/h7,18-21,23-42,46-54H,8-17H2,1-6H3/t18-,19+,20+,21+,23+,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(O[C@H]1O)O[C@H]1C[C@H]3[C@@H]4CC=C5C[C@@H](O[C@@H]6O[C@H](CO)[C@@H](O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@H](O)[C@H]6O[C@@H]6O[C@@H](C)[C@H](O)[C@@H](O)[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:	884.48	Volume:	856.665 ? Van der Waals volume.
Dense:	1.032	LogP:	2.101 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.939 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.485 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	48.0
TPSA:	255.91 ? Topological Polar Surface Area.	H-Bond Acceptor:	17.0
H-Bond Donor:	9.0	Rings:	9.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.158	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.81	Fsp³:	0.956
MCE-18:	232.909 ? 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:	0.7	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.299	Promiscuous compounds:	0.013

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.115	MDCK Permeability:	-5.046
Pgp-inhibitor:	0.0	Pgp-substrate:	0.987
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):	0.081
20% Bioavailability (F20%):	0.235	30% Bioavailability (F30%):	0.955
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.016
Plasma Protein Binding (PPB):	58.187%	Volume Distribution (VD):	-0.435
Fu:	33.955% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.169
BSEP inhibitor:	0.089

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:	0.426	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.772
HLM stability:	0.179 ? 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):

0.247

Half-life (T1/2):

3.897

ADMET: Toxicity

hERG Blockers:	0.069	hERG Blockers (10um):	0.309
Human Hepatotoxicity (H-HT):	0.223	Drug-induced Liver Injury (DILI):	0.876
AMES Toxicity:	0.682	Rat Oral Acute Toxicity:	0.009
Maximum Recommended Daily Dose:	0.01	Skin Sensitization:	1.0
Carcinogencity:	0.007	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.088	Drug-induced Nephrotoxicity:	0.263
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.297
A549 Cytotoxicity:	0.277	Hek293 Cytotoxicity:	0.671
BCF:	1.701 ? 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:	3.455 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.696 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.027 ? 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
NPO8266	Solanum anguivi	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8266	Solanum anguivi	Species	Solanaceae	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 NPC531525 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	24554
0.1-0.2	22176
0.2-0.3	2467
0.3-0.4	479
0.4-0.5	103
0.5-0.6	24
0.6-0.7	33
0.7-0.8	0
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8316	Intermediate Similarity	NPC470433
0.8316	Intermediate Similarity	NPC46190
0.8316	Intermediate Similarity	NPC171073
0.8229	Intermediate Similarity	NPC248746
0.8144	Intermediate Similarity	NPC42171
0.8061	Intermediate Similarity	NPC480555
0.8061	Intermediate Similarity	NPC150372
0.7843	Intermediate Similarity	NPC194207
0.7843	Intermediate Similarity	NPC22779
0.7822	Intermediate Similarity	NPC269297
0.7822	Intermediate Similarity	NPC222202
0.7745	Intermediate Similarity	NPC475333
0.7745	Intermediate Similarity	NPC224098
0.7745	Intermediate Similarity	NPC208383
0.7596	Intermediate Similarity	NPC480554
0.7477	Intermediate Similarity	NPC232054
0.7453	Intermediate Similarity	NPC480553
0.7117	Intermediate Similarity	NPC480556
0.7071	Intermediate Similarity	NPC94272
0.7054	Intermediate Similarity	NPC224314
0.6931	Remote Similarity	NPC113044
0.6931	Remote Similarity	NPC283829
0.6931	Remote Similarity	NPC161676
0.69	Remote Similarity	NPC470432
0.69	Remote Similarity	NPC230507
0.6827	Remote Similarity	NPC122819
0.6759	Remote Similarity	NPC32361
0.6737	Remote Similarity	NPC165439
0.6731	Remote Similarity	NPC602423
0.6636	Remote Similarity	NPC73243
0.6636	Remote Similarity	NPC244086
0.6636	Remote Similarity	NPC84956
0.6604	Remote Similarity	NPC300557
0.6514	Remote Similarity	NPC247037
0.6455	Remote Similarity	NPC309278
0.6449	Remote Similarity	NPC6806
0.6436	Remote Similarity	NPC19400
0.6389	Remote Similarity	NPC475182
0.6355	Remote Similarity	NPC477809
0.6339	Remote Similarity	NPC249265
0.6306	Remote Similarity	NPC13193
0.6296	Remote Similarity	NPC124677
0.6286	Remote Similarity	NPC305423
0.6286	Remote Similarity	NPC14704
0.6283	Remote Similarity	NPC23808
0.6283	Remote Similarity	NPC87998
0.6271	Remote Similarity	NPC477808
0.625	Remote Similarity	NPC485595
0.625	Remote Similarity	NPC6295
0.6174	Remote Similarity	NPC287885
0.6162	Remote Similarity	NPC181845
0.6111	Remote Similarity	NPC265275
0.6071	Remote Similarity	NPC475550
0.5897	Remote Similarity	NPC308140
0.5812	Remote Similarity	NPC477811
0.5652	Remote Similarity	NPC486386
0.5648	Remote Similarity	NPC15249
0.5648	Remote Similarity	NPC25455
0.5596	Remote Similarity	NPC141433
0.5596	Remote Similarity	NPC195297
0.5586	Remote Similarity	NPC98696
0.5556	Remote Similarity	NPC254255
0.5478	Remote Similarity	NPC102016
0.5478	Remote Similarity	NPC95051
0.5439	Remote Similarity	NPC471464
0.5391	Remote Similarity	NPC150057
0.5391	Remote Similarity	NPC147753
0.537	Remote Similarity	NPC306131
0.537	Remote Similarity	NPC200802
0.534	Remote Similarity	NPC486114
0.525	Remote Similarity	NPC218571
0.525	Remote Similarity	NPC487615
0.5234	Remote Similarity	NPC477451
0.5175	Remote Similarity	NPC40440
0.5172	Remote Similarity	NPC249553
0.5133	Remote Similarity	NPC160426
0.513	Remote Similarity	NPC475643

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC531525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7780
0.1-0.2	1307
0.2-0.3	51
0.3-0.4	8
0.4-0.5	2
0.5-0.6	1
0.6-0.7	1
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
0.6827	Remote Similarity	NPD8449	Approved
0.5391	Remote 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