NPASS Compound

Natural Product: NPC240531

Natural Product ID	NPC240531
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	LEXYZULQYUZKOY-KOCGNUEFSA-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 [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 133141 0 0 0 0 0 0 0 0999 V2000 14.1895 -0.0651 0.6833 C 0 0 0 0 0 0 0 0 0 0 0 0 12.7502 -0.1167 0.2041 C 0 0 2 0 0 0 0 0 0 0 0 0 11.9226 0.9897 0.8033 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7280 0.4651 1.5710 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9973 -0.5923 0.7731 C 0 0 2 0 0 0 0 0 0 0 0 0 9.1800 0.0021 -0.3525 C 0 0 1 0 0 0 0 0 0 0 0 0 9.9683 -0.0939 -1.6673 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0438 -0.9598 -0.4646 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2104 -1.9128 0.7046 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8061 -2.1113 1.2957 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9568 -1.6499 0.1912 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5417 -1.3044 0.4402 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7606 -2.3813 1.1468 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3203 -2.1612 0.9697 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7656 -1.3334 0.0915 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2835 -1.2735 0.0910 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3470 -0.4521 -0.9531 C 0 0 2 0 0 0 0 0 0 0 0 0 0.4915 0.0261 -2.0756 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8769 -0.5097 -2.1679 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6024 -0.5155 -0.8350 C 0 0 1 0 0 0 0 0 0 0 0 0 2.6516 0.8639 -0.2280 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9218 -1.1748 -0.9550 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8802 -0.5804 -1.9322 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0077 0.2187 -1.3661 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6875 -0.3541 -0.1864 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7491 0.5916 0.9727 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0241 0.6740 -0.4415 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3771 0.6392 -0.6707 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1585 0.7137 0.6052 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7775 2.0591 1.2376 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2401 3.1267 0.2777 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5022 2.9106 -1.0309 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9499 3.9338 -2.0673 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7732 1.6520 -1.5661 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9427 4.4078 0.7478 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2956 2.1775 2.5099 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5124 0.7605 0.2961 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2561 -0.2434 0.9304 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.2727 0.3998 1.8380 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3391 1.0150 0.9559 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.0333 -0.1263 0.2259 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.0797 -1.1249 -0.3111 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.1510 -1.1194 -1.8595 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5071 -1.0921 -2.1775 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8183 -1.1569 0.1313 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9203 -0.7055 1.1204 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2355 -0.5722 0.7605 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.9295 -1.8843 0.5893 C 0 0 1 0 0 0 0 0 0 0 0 0 -12.2753 -1.6775 -0.0182 C 0 0 1 0 0 0 0 0 0 0 0 0 -13.0247 -0.5928 0.6858 C 0 0 2 0 0 0 0 0 0 0 0 0 -12.1986 0.5725 1.0959 C 0 0 2 0 0 0 0 0 0 0 0 0 -11.9620 1.4749 -0.0960 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9554 0.2637 1.6240 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.6203 -1.1350 1.8436 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.2121 -1.3642 -1.3780 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.1887 -2.7593 -0.1877 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7166 1.7696 -0.0334 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8797 -0.6644 2.5417 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0673 -1.2657 1.5632 O 0 0 0 0 0 0 0 0 0 0 0 0 10.8494 -1.5230 0.2222 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1603 -1.4257 0.6471 C 0 0 0 0 0 0 0 0 0 0 0 0 14.4688 -0.9913 1.2209 H 0 0 0 0 0 0 0 0 0 0 0 0 14.9028 0.0505 -0.1710 H 0 0 0 0 0 0 0 0 0 0 0 0 14.3315 0.8097 1.3494 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7748 -0.0864 -0.9031 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5638 1.5367 1.5220 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6042 1.7366 0.0430 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0893 -0.0238 2.4961 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0513 1.2953 1.7855 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9301 1.0461 -0.2094 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1960 -0.2189 -2.4748 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6648 -0.9469 -1.6318 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4859 0.8468 -1.8945 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9910 -1.4813 -1.4255 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6125 -2.8584 0.3049 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6897 -1.6216 2.2616 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6709 -3.2148 1.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0396 -2.3372 -0.6681 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3527 -0.3612 0.9508 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9791 -2.2916 2.2429 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1011 -3.3821 0.8441 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6594 -2.7414 1.6290 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0078 -0.8262 1.0941 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1569 -2.3126 0.1614 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1680 -1.0846 -1.4163 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0158 -0.1928 -3.0834 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5564 1.1574 -2.0969 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8512 -1.5852 -2.5014 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4031 0.1029 -2.9279 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7071 1.4248 -0.4352 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4720 1.4937 -0.5526 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6871 0.7986 0.8987 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7192 -2.2461 -1.2602 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3561 -1.4127 -2.5344 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4026 0.0642 -2.7008 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7842 0.2841 -2.1879 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7665 1.2866 -1.1621 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0556 0.3778 1.7876 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5038 1.6375 0.6264 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7603 0.6707 1.4199 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6282 -0.3036 -1.1897 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8822 -0.1181 1.2689 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6472 2.0383 1.2660 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3039 2.9932 0.0655 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4432 3.0888 -0.8531 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0330 4.2035 -1.9058 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3282 4.8548 -2.0124 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8859 3.5561 -3.0995 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7137 4.6256 1.3643 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4358 1.2399 2.8591 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4808 -0.8019 1.5546 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8657 1.1475 2.5243 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0599 1.5715 1.5500 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5780 0.3467 -0.6276 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5313 -2.1465 -0.0702 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6974 -0.1987 -2.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7392 -2.0527 -2.2353 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7813 -1.8221 -2.7606 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2618 -0.0331 -0.2234 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.0889 -2.4004 1.5621 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8892 -2.6204 0.0293 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.9093 -0.2736 0.0544 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8114 1.1735 1.8096 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0882 0.9111 -1.0342 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9395 1.9226 -0.1072 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.7129 2.3043 -0.1487 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.4103 -0.5796 2.1173 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1004 -2.1797 -1.9359 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7011 -3.3123 -0.7998 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1705 1.7000 -0.8988 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6603 -0.3503 3.0691 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7122 -2.2614 0.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2892 -1.5689 1.7318 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 32 34 1 0 31 35 1 0 30 36 1 0 29 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 43 44 1 0 42 45 1 0 41 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 51 53 1 0 50 54 1 0 49 55 1 0 48 56 1 0 40 57 1 0 39 58 1 0 9 59 1 0 5 60 1 6 60 61 1 0 61 2 1 0 59 5 1 0 25 8 1 0 34 28 1 0 45 38 1 0 53 47 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 6 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 1 31104 1 6 32105 1 1 33106 1 0 33107 1 0 33108 1 0 35109 1 0 36110 1 0 38111 1 1 39112 1 1 40113 1 1 41114 1 6 42115 1 1 43116 1 0 43117 1 0 44118 1 0 47119 1 6 48120 1 1 49121 1 6 50122 1 6 51123 1 1 52124 1 0 52125 1 0 52126 1 0 54127 1 0 55128 1 0 56129 1 0 57130 1 0 58131 1 0 61132 1 0 61133 1 0 M END

Standard InCHIKey	LEXYZULQYUZKOY-KOCGNUEFSA-N
Standard InCHI	InChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)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(34(50)32(48)22(4)56-42)60-41-37(53)35(51)38(29(17-46)58-41)59-40-36(52)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,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](C)O3)O)O)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)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	868.48	Volume:	847.875 ? Van der Waals volume.
Dense:	1.024	LogP:	2.762 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.549 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.914 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	48.0
TPSA:	235.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	8.0	Rings:	9.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.168	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.675	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:	0.798	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:	0.236	Promiscuous compounds:	0.015

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.156	MDCK Permeability:	-5.046
Pgp-inhibitor:	0.002	Pgp-substrate:	0.89
PAMPA:	0.995 ? 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%):	0.027	30% Bioavailability (F30%):	0.454
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.009
Plasma Protein Binding (PPB):	67.794%	Volume Distribution (VD):	-0.354
Fu:	25.443% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.339
BSEP inhibitor:	0.566

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:	0.985	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.306 ? 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):

0.306

Half-life (T1/2):

3.554

ADMET: Toxicity

hERG Blockers:	0.066	hERG Blockers (10um):	0.292
Human Hepatotoxicity (H-HT):	0.374	Drug-induced Liver Injury (DILI):	0.982
AMES Toxicity:	0.886	Rat Oral Acute Toxicity:	0.05
Maximum Recommended Daily Dose:	0.059	Skin Sensitization:	1.0
Carcinogencity:	0.037	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.004
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.997
Hematotoxicity:	0.151	Drug-induced Nephrotoxicity:	0.565
Genotoxicity:	0.02	RPMI-8226 Immunitoxicity:	0.368
A549 Cytotoxicity:	0.845	Hek293 Cytotoxicity:	0.875
BCF:	1.984 ? 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:	3.577 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.726 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.153 ? 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
NPO4916	Toxicodendron vernicifluum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4916	Toxicodendron vernicifluum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4916	Toxicodendron vernicifluum	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4916	Toxicodendron vernicifluum	Species	Anacardiaceae	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 NPC240531 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	24154
0.1-0.2	22329
0.2-0.3	2477
0.3-0.4	641
0.4-0.5	104
0.5-0.6	77
0.6-0.7	38
0.7-0.8	0
0.8-0.85	6
0.85-0.9	11
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9101	High Similarity	NPC470432
0.9101	High Similarity	NPC230507
0.8817	High Similarity	NPC470433
0.8817	High Similarity	NPC46190
0.8817	High Similarity	NPC171073
0.8723	High Similarity	NPC477809
0.8696	High Similarity	NPC113044
0.8696	High Similarity	NPC283829
0.8696	High Similarity	NPC161676
0.866	High Similarity	NPC269297
0.866	High Similarity	NPC222202
0.8542	High Similarity	NPC480555
0.8542	High Similarity	NPC150372
0.8218	Intermediate Similarity	NPC480554
0.82	Intermediate Similarity	NPC475333
0.82	Intermediate Similarity	NPC224098
0.82	Intermediate Similarity	NPC208383
0.8144	Intermediate Similarity	NPC248746
0.8058	Intermediate Similarity	NPC480553
0.7879	Intermediate Similarity	NPC6806
0.7857	Intermediate Similarity	NPC602423
0.7778	Intermediate Similarity	NPC224314
0.77	Intermediate Similarity	NPC42171
0.77	Intermediate Similarity	NPC300557
0.7685	Intermediate Similarity	NPC480556
0.7596	Intermediate Similarity	NPC194207
0.7596	Intermediate Similarity	NPC22779
0.7551	Intermediate Similarity	NPC14704
0.75	Intermediate Similarity	NPC32361
0.75	Intermediate Similarity	NPC181845
0.7404	Intermediate Similarity	NPC475550
0.7248	Intermediate Similarity	NPC232054
0.7222	Intermediate Similarity	NPC477811
0.71	Intermediate Similarity	NPC141433
0.703	Intermediate Similarity	NPC305423
0.7009	Intermediate Similarity	NPC13193
0.69	Remote Similarity	NPC107962
0.6869	Remote Similarity	NPC306131
0.6869	Remote Similarity	NPC200802
0.6869	Remote Similarity	NPC19400
0.6852	Remote Similarity	NPC309278
0.6735	Remote Similarity	NPC477451
0.6667	Remote Similarity	NPC485595
0.6667	Remote Similarity	NPC6295
0.6638	Remote Similarity	NPC477808
0.6542	Remote Similarity	NPC124677
0.6531	Remote Similarity	NPC325828
0.6415	Remote Similarity	NPC40440
0.6404	Remote Similarity	NPC31896
0.6364	Remote Similarity	NPC297348
0.6364	Remote Similarity	NPC249204
0.6364	Remote Similarity	NPC48339
0.6364	Remote Similarity	NPC141769
0.6364	Remote Similarity	NPC477547
0.6306	Remote Similarity	NPC247037
0.6273	Remote Similarity	NPC73243
0.6273	Remote Similarity	NPC244086
0.6273	Remote Similarity	NPC84956
0.6262	Remote Similarity	NPC98696
0.6239	Remote Similarity	NPC249553
0.6228	Remote Similarity	NPC23808
0.6228	Remote Similarity	NPC87998
0.619	Remote Similarity	NPC15249
0.619	Remote Similarity	NPC94272
0.619	Remote Similarity	NPC25455
0.6182	Remote Similarity	NPC475182
0.6176	Remote Similarity	NPC250393
0.6167	Remote Similarity	NPC210569
0.6147	Remote Similarity	NPC122819
0.6132	Remote Similarity	NPC70204
0.6058	Remote Similarity	NPC211354
0.6019	Remote Similarity	NPC222731
0.6	Remote Similarity	NPC249265
0.6	Remote Similarity	NPC92890
0.5983	Remote Similarity	NPC308140
0.5981	Remote Similarity	NPC195297
0.5965	Remote Similarity	NPC475625
0.5902	Remote Similarity	NPC15918
0.59	Remote Similarity	NPC486114
0.5887	Remote Similarity	NPC305771
0.5887	Remote Similarity	NPC94072
0.5887	Remote Similarity	NPC169816
0.5868	Remote Similarity	NPC477807
0.5851	Remote Similarity	NPC100451
0.5842	Remote Similarity	NPC485594
0.5841	Remote Similarity	NPC184617
0.5804	Remote Similarity	NPC471464
0.578	Remote Similarity	NPC160426
0.5714	Remote Similarity	NPC287885
0.5702	Remote Similarity	NPC97700
0.5702	Remote Similarity	NPC30856
0.5702	Remote Similarity	NPC102016
0.5702	Remote Similarity	NPC95051
0.5686	Remote Similarity	NPC165439
0.5678	Remote Similarity	NPC83137
0.5673	Remote Similarity	NPC294686
0.5664	Remote Similarity	NPC182900
0.566	Remote Similarity	NPC206003
0.566	Remote Similarity	NPC473610
0.5638	Remote Similarity	NPC235126
0.5638	Remote Similarity	NPC242419
0.5635	Remote Similarity	NPC263359
0.5607	Remote Similarity	NPC107188
0.5565	Remote Similarity	NPC294129
0.5536	Remote Similarity	NPC42482
0.5536	Remote Similarity	NPC486388
0.5508	Remote Similarity	NPC232037
0.55	Remote Similarity	NPC132080
0.5487	Remote Similarity	NPC265275
0.5478	Remote Similarity	NPC128572
0.5462	Remote Similarity	NPC218571
0.5462	Remote Similarity	NPC487615
0.5455	Remote Similarity	NPC306991
0.5405	Remote Similarity	NPC475670
0.54	Remote Similarity	NPC144790
0.54	Remote Similarity	NPC149400
0.5391	Remote Similarity	NPC244431
0.5378	Remote Similarity	NPC254255
0.5377	Remote Similarity	NPC234352
0.5357	Remote Similarity	NPC470748
0.5357	Remote Similarity	NPC600116
0.5345	Remote Similarity	NPC150057
0.5345	Remote Similarity	NPC147753
0.5339	Remote Similarity	NPC486386
0.531	Remote Similarity	NPC475351
0.531	Remote Similarity	NPC112274
0.5289	Remote Similarity	NPC476112
0.5289	Remote Similarity	NPC307534
0.5263	Remote Similarity	NPC197231
0.5254	Remote Similarity	NPC115165
0.525	Remote Similarity	NPC63609
0.5229	Remote Similarity	NPC121453
0.5217	Remote Similarity	NPC475643
0.5207	Remote Similarity	NPC470864
0.5204	Remote Similarity	NPC486119
0.5175	Remote Similarity	NPC19888
0.5167	Remote Similarity	NPC116756
0.5156	Remote Similarity	NPC79900
0.514	Remote Similarity	NPC177834
0.5096	Remote Similarity	NPC481420
0.5096	Remote Similarity	NPC473774
0.5096	Remote Similarity	NPC481419
0.5096	Remote Similarity	NPC481417
0.5096	Remote Similarity	NPC481421
0.5093	Remote Similarity	NPC131693
0.5093	Remote Similarity	NPC475436
0.5049	Remote Similarity	NPC277715
0.5045	Remote Similarity	NPC54619
0.5044	Remote Similarity	NPC125324
0.5043	Remote Similarity	NPC469348
0.5041	Remote Similarity	NPC473518

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC240531 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7624
0.1-0.2	1450
0.2-0.3	65
0.3-0.4	5
0.4-0.5	2
0.5-0.6	2
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
0.6531	Remote Similarity	NPD8171	Phase 2
0.6147	Remote Similarity	NPD8449	Approved
0.5888	Remote Similarity	NPD8170	Phase 2
0.5345	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