NPASS Compound

Natural Product: NPC471964

Natural Product ID	NPC471964
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OBFDSOYVKVRFGY-GKDIEYKBSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3314501
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene 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 126132 0 0 0 0 0 0 0 0999 V2000 -9.9857 2.0422 -2.5122 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3326 1.2340 -1.4435 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7714 0.0688 -1.2308 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3003 1.6646 -0.6865 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6335 0.9990 0.3166 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.7262 1.6521 1.6715 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1270 0.7516 2.7047 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.1603 -0.2982 3.1225 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8704 0.0342 2.1569 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3136 0.8982 1.1057 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1823 0.8375 -0.1258 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8189 2.0874 -0.9495 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9743 -0.3548 -0.9636 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7606 -1.1723 -0.8457 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6204 -0.6486 -0.0058 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9490 0.6448 0.6256 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0617 1.6172 0.7581 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6781 1.4869 0.3164 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9794 2.5295 0.3190 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2405 0.1479 -0.0881 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.3329 -0.5311 -0.8417 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7118 0.1579 -2.1109 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9488 -1.9659 -1.1713 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6510 -1.9202 -1.9538 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3735 -1.3827 -0.9848 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1148 0.0605 -0.7180 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3659 0.9713 -1.8682 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1258 0.4500 0.3591 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5488 0.2049 -0.0371 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8447 -1.1426 -0.5608 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7432 -1.7953 -1.3402 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0312 -1.6772 -2.8455 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8195 -3.2967 -1.0619 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9582 -1.0785 -1.3957 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0474 -1.8153 -0.9256 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3158 -2.8985 -1.7571 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6451 -3.2700 -1.8151 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1614 -3.7725 -0.5194 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3535 -4.1530 -0.4572 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3651 -3.8227 0.5855 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5197 -2.1607 -2.3685 C 0 0 2 0 0 0 0 0 0 0 0 0 6.8522 -0.8098 -2.1839 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2113 -0.8886 -0.7830 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7815 0.3703 -0.3855 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4008 0.8635 0.7358 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5403 1.2017 1.7758 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3415 1.2837 2.9193 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5187 1.0946 4.1319 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3004 0.9080 4.0258 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1074 1.1255 5.3850 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9710 2.6664 2.8779 C 0 0 2 0 0 0 0 0 0 0 0 0 6.9658 3.2039 1.4723 C 0 0 1 0 0 0 0 0 0 0 0 0 7.2184 2.1095 0.4455 C 0 0 1 0 0 0 0 0 0 0 0 0 8.5723 1.8221 0.3259 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6746 3.7234 1.2293 O 0 0 0 0 0 0 0 0 0 0 0 0 8.2458 2.6314 3.4258 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7267 0.2385 -2.2946 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7274 -2.3456 -3.7120 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3723 -1.6862 1.0562 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8075 1.5585 3.9050 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3375 1.2749 5.0026 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.9251 2.6359 3.8506 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.5795 2.8266 -2.0108 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6891 1.4094 -3.1017 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2721 2.4817 -3.2127 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0706 -0.0105 0.4409 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3227 2.6589 1.7356 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8258 1.7044 1.9081 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1755 0.0593 2.8520 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9314 -1.2765 2.6353 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1535 -0.4478 4.2181 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2814 -0.9345 1.7902 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2304 -0.0576 3.0594 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4322 1.9617 1.4808 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0662 1.8165 -2.0161 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7610 2.3239 -0.8716 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5069 2.9012 -0.6856 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1553 -0.0271 -2.0400 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9020 -0.9984 -0.8095 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0774 -2.2164 -0.5157 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3769 -1.3886 -1.8637 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3734 2.5712 1.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1028 -0.4072 0.8886 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1822 1.1225 -2.2649 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7876 0.4694 -2.1587 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5048 -0.4373 -3.0403 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6553 -2.4515 -0.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7218 -2.5277 -1.6829 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3810 -2.9583 -2.2423 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6922 -1.2983 -2.8444 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1521 -1.9039 0.0007 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0646 0.5872 -2.8603 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4766 1.1606 -1.9937 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0375 1.9807 -1.7472 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8864 -0.2019 1.2306 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0525 1.4824 0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9797 1.0239 -0.6492 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1059 0.3156 0.9491 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1560 -1.8191 0.2953 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1865 -2.0042 -3.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4688 -0.7019 -3.1106 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8553 -2.4207 -3.0691 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4779 -3.4518 -0.2089 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8269 -3.7250 -0.7916 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2683 -3.8562 -1.9190 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7507 -2.2389 0.0540 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7144 -4.1162 -2.5304 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7094 -3.8917 1.5334 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4622 -2.1368 -1.7759 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0107 -0.6486 -2.8854 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9778 -1.2084 -0.0433 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1432 0.0908 1.0863 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1587 0.5283 2.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6499 0.7087 6.1686 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3388 3.3262 3.5075 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7384 3.9709 1.3889 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8556 2.5380 -0.5315 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9265 2.1389 -0.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6613 4.6404 1.5825 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4889 3.4767 3.8884 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7126 0.6781 -3.1594 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8788 -2.6213 -4.1205 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3929 -1.6779 1.5377 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1077 -1.7219 1.8668 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5246 -2.6937 0.5373 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7783 3.1583 4.7026 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 1 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 6 11 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 6 26 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 31 33 1 0 30 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 2 0 38 40 1 0 37 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 2 0 48 50 1 0 47 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 52 55 1 0 51 56 1 0 42 57 1 0 41 58 1 0 15 59 1 1 7 60 1 0 60 61 2 0 60 62 1 0 11 5 1 0 21 15 1 0 31 25 1 0 43 35 1 0 53 45 1 0 16 10 1 0 26 20 1 0 1 63 1 0 1 64 1 0 1 65 1 0 5 66 1 1 6 67 1 0 6 68 1 0 8 69 1 0 8 70 1 0 8 71 1 0 9 72 1 0 9 73 1 0 10 74 1 1 12 75 1 0 12 76 1 0 12 77 1 0 13 78 1 0 13 79 1 0 14 80 1 0 14 81 1 0 17 82 1 0 20 83 1 1 22 84 1 0 22 85 1 0 22 86 1 0 23 87 1 0 23 88 1 0 24 89 1 0 24 90 1 0 25 91 1 1 27 92 1 0 27 93 1 0 27 94 1 0 28 95 1 0 28 96 1 0 29 97 1 0 29 98 1 0 30 99 1 1 32100 1 0 32101 1 0 32102 1 0 33103 1 0 33104 1 0 33105 1 0 35106 1 1 37107 1 6 40108 1 0 41109 1 1 42110 1 6 43111 1 1 45112 1 1 47113 1 6 50114 1 0 51115 1 1 52116 1 1 53117 1 6 54118 1 0 55119 1 0 56120 1 0 57121 1 0 58122 1 0 59123 1 0 59124 1 0 59125 1 0 62126 1 0 M END

Standard InCHIKey	OBFDSOYVKVRFGY-GKDIEYKBSA-N
Standard InCHI	InChI=1S/C44H64O18/c1-18(45)58-24-17-40(4,38(56)57)16-20-19-15-21(46)33-42(6)11-10-23(39(2,3)22(42)9-12-44(33,8)43(19,7)14-13-41(20,24)5)59-37-32(28(50)27(49)31(61-37)35(54)55)62-36-29(51)25(47)26(48)30(60-36)34(52)53/h15,20,22-33,36-37,47-51H,9-14,16-17H2,1-8H3,(H,52,53)(H,54,55)(H,56,57)/t20-,22-,23-,24+,25-,26-,27-,28-,29+,30-,31-,32+,33+,36-,37-,40+,41+,42-,43+,44+/m0/s1
SMILES	CC(=O)O[C@@H]1C[C@@](C)(C[C@@H]2[C@@]1(C)CC[C@@]1(C2=CC(=O)[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)CC[C@@H](C1(C)C)O[C@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O[C@@H]1O[C@H](C(=O)O)[C@H]([C@@H]([C@H]1O)O)O)O)O)C)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	880.41	Volume:	852.09 ? Van der Waals volume.
Dense:	1.033	LogP:	1.175 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.659 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.646 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	43.0
TPSA:	293.34 ? Topological Polar Surface Area.	H-Bond Acceptor:	18.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	18.0

MedChem Properties

QED Drug-Likeness Score:	0.127	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.13	Fsp³:	0.841
MCE-18:	162.963 ? 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:	0.771	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.09 ? 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:	0.159	Promiscuous compounds:	0.325

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.03	MDCK Permeability:	-5.151
Pgp-inhibitor:	0.0	Pgp-substrate:	0.006
PAMPA:	1.0 ? 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):	0.005
20% Bioavailability (F20%):	0.019	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.379

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	1.0
Plasma Protein Binding (PPB):	62.703%	Volume Distribution (VD):	-0.615
Fu:	27.978% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	0.287	BCRP inhibitor:	0.0
BSEP inhibitor:	0.011

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:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
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):

0.257

Half-life (T1/2):

3.836

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.0
Human Hepatotoxicity (H-HT):	0.756	Drug-induced Liver Injury (DILI):	0.992
AMES Toxicity:	0.246	Rat Oral Acute Toxicity:	0.042
Maximum Recommended Daily Dose:	0.029	Skin Sensitization:	0.995
Carcinogencity:	0.106	Eye Corrosion:	0.0
Eye Irritation:	0.061	Respiratory Toxicity:	0.127
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.992
Hematotoxicity:	0.667	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.964	RPMI-8226 Immunitoxicity:	0.017
A549 Cytotoxicity:	0.001	Hek293 Cytotoxicity:	0.001
BCF:	0.371 ? 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:	3.36 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.045 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.091 ? 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
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11164-015-2099-x]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1134/S1021443711030101]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	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

Activity Type	# Activity
IC50	2
Inhibition	1

Activity Type	# Activity
Organism	1
Non-molecular	2

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
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	=	49100.0	nM	PMID[24957203]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	47.5	%	PMID[24957203]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	29500.0	nM	DOI[10.6019/CHEMBL1201861]

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 NPC471964 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	20174
0.1-0.2	25700
0.2-0.3	3306
0.3-0.4	545
0.4-0.5	87
0.5-0.6	7
0.6-0.7	7
0.7-0.8	0
0.8-0.85	8
0.85-0.9	2
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC482734
1.0	High Similarity	NPC182342
1.0	High Similarity	NPC482727
0.9053	High Similarity	NPC482755
0.8866	High Similarity	NPC482737
0.8866	High Similarity	NPC482735
0.8269	Intermediate Similarity	NPC482739
0.819	Intermediate Similarity	NPC482736
0.819	Intermediate Similarity	NPC482738
0.8081	Intermediate Similarity	NPC482744
0.8041	Intermediate Similarity	NPC482747
0.8041	Intermediate Similarity	NPC202666
0.8041	Intermediate Similarity	NPC471961
0.8041	Intermediate Similarity	NPC242015
0.7879	Intermediate Similarity	NPC285091
0.7379	Intermediate Similarity	NPC482722
0.7379	Intermediate Similarity	NPC471963
0.7374	Intermediate Similarity	NPC482750
0.7353	Intermediate Similarity	NPC471965
0.7353	Intermediate Similarity	NPC482749
0.7255	Intermediate Similarity	NPC482741
0.7255	Intermediate Similarity	NPC482745
0.7255	Intermediate Similarity	NPC482743
0.7255	Intermediate Similarity	NPC146753
0.7157	Intermediate Similarity	NPC482717
0.7075	Intermediate Similarity	NPC262199
0.7048	Intermediate Similarity	NPC482729
0.7048	Intermediate Similarity	NPC482742
0.7041	Intermediate Similarity	NPC482752
0.6852	Remote Similarity	NPC247315
0.6852	Remote Similarity	NPC482728
0.6792	Remote Similarity	NPC14617
0.6509	Remote Similarity	NPC482746
0.6381	Remote Similarity	NPC309780
0.6261	Remote Similarity	NPC471962
0.625	Remote Similarity	NPC482740
0.5727	Remote Similarity	NPC482748
0.5714	Remote Similarity	NPC471967
0.5596	Remote Similarity	NPC482726
0.5586	Remote Similarity	NPC275343
0.5408	Remote Similarity	NPC74751
0.5263	Remote Similarity	NPC482751
0.5085	Remote Similarity	NPC251768

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471964 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6402
0.1-0.2	2695
0.2-0.3	45
0.3-0.4	2
0.4-0.5	3
0.5-0.6	1
0.6-0.7	0
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8041	Intermediate Similarity	NPD8328	Phase 2
0.5408	Remote Similarity	NPD7748	Pre-clinical

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