NPASS Compound

Natural Product: NPC119794

Natural Product ID	NPC119794
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-O-[Beta-D-Glucopyranosyl-(1''->6')-2'-Acetamido-2'-Deoxy-Beta-D-Glucopyranosy;}Olean-12-En-28-Oic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bR)-10-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL451292
PubChem CID	44584414
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 129135 0 0 0 0 0 0 0 0999 V2000 5.3558 -2.5516 3.6409 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1119 -1.8192 3.8973 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5615 -0.9516 3.1451 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0795 -0.5182 1.8631 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1136 0.5892 2.1108 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1312 1.5568 0.9807 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7416 0.9414 -0.3405 C 0 0 1 0 0 0 0 0 0 0 0 0 5.9139 0.1368 -0.8617 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0474 0.9344 -0.8767 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1619 0.2202 -1.3532 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6254 0.8721 -2.6113 C 0 0 1 0 0 0 0 0 0 0 0 0 10.1227 0.7820 -2.8051 C 0 0 2 0 0 0 0 0 0 0 0 0 10.8117 1.3503 -1.5854 C 0 0 1 0 0 0 0 0 0 0 0 0 10.0106 1.1447 -0.3244 C 0 0 1 0 0 0 0 0 0 0 0 0 9.3597 2.4323 0.1426 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3693 3.4223 0.1527 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1305 0.0936 -0.3806 O 0 0 0 0 0 0 0 0 0 0 0 0 12.0822 0.7872 -1.4841 O 0 0 0 0 0 0 0 0 0 0 0 0 10.4543 1.5740 -3.8860 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0359 0.2140 -3.6945 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5782 0.2291 -0.2965 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0227 0.0761 0.9820 C 0 0 1 0 0 0 0 0 0 0 0 0 1.9100 -0.7398 0.7920 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7132 -0.1820 1.1517 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1128 0.1351 -0.1132 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6373 -1.1415 -0.6745 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7138 -1.7076 0.2249 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6029 -3.1986 0.1350 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4778 -1.1495 1.6076 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4110 -1.7582 2.5954 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8335 -1.7798 2.1965 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1829 -1.4989 0.7980 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.9223 -2.7391 0.2564 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0644 -1.2056 -0.1606 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5140 -1.5144 -1.5674 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6867 -0.5877 -1.7808 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4074 -0.0893 -0.7703 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5556 0.8271 -1.0647 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.6615 1.2142 -2.5101 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7593 2.2680 -2.5868 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4388 3.4226 -1.6544 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9293 2.8174 -3.9646 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0374 1.6367 -2.1427 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0155 1.1106 -0.7320 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7904 0.2517 -0.4708 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.5875 0.2567 1.0267 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4266 -0.5816 1.4605 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1660 -0.3515 0.6692 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5386 0.9342 1.2158 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0572 -1.0874 -0.9912 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1779 -2.0747 -0.2122 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1896 -1.3428 -2.3327 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0581 -1.1066 2.0593 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0865 -0.3970 3.4262 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6040 -2.4159 2.2395 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4048 2.7088 1.2746 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3522 0.0339 2.3941 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4491 -2.1004 5.1031 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2765 -3.6133 4.0174 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2000 -2.0726 4.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6501 -2.6242 2.5900 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5507 -1.3853 1.3993 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7799 1.1258 3.0230 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1981 1.9047 0.8522 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6026 1.7841 -1.0578 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1321 -0.7613 -0.2875 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6492 -0.2084 -1.9015 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8066 -0.8231 -1.5889 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2821 1.9433 -2.7111 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3899 -0.2608 -2.9915 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9727 2.4550 -1.6879 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7597 0.8884 0.4823 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0306 2.3561 1.1990 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4950 2.7296 -0.4581 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9823 4.3177 0.3227 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1482 0.1327 -0.7446 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2924 2.0538 -3.7571 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6062 -0.5364 -4.0111 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6540 1.0284 1.3970 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9098 0.8228 1.5747 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8300 0.9329 0.0523 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6525 0.5458 -0.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8890 -1.0703 -1.7252 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2320 -1.8707 -0.6317 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5289 -3.4939 0.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0725 -3.7690 0.9281 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0129 -3.5036 -0.8514 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7833 -0.0592 1.5398 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0185 -2.7900 2.8213 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2584 -1.2011 3.5626 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2496 -2.7754 2.5429 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3852 -1.0597 2.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -3.5399 -0.0500 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5496 -3.2077 1.0464 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5513 -2.5309 -0.6004 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9397 -0.0770 -0.1617 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7731 -1.1873 -2.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7511 -2.5539 -1.7646 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9524 -0.3189 -2.7895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2788 1.7862 -0.5202 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8954 0.3891 -3.1783 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7176 1.7348 -2.7741 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7326 3.2266 -0.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3305 3.6027 -1.6324 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9941 4.3090 -1.9881 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8887 3.3822 -3.9834 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9993 2.0542 -4.7550 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1351 3.5779 -4.1461 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8318 2.4356 -2.1643 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3962 0.8461 -2.8258 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.1206 1.8835 0.0426 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8961 0.4355 -0.6297 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3927 1.3055 1.3289 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4775 -0.0909 1.5731 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2040 -0.2475 2.5182 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6777 -1.6483 1.5275 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3884 1.5996 1.5506 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0163 1.5146 0.4463 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9329 0.7699 2.1167 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8445 -2.0349 -2.6927 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8014 0.4415 3.3089 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9022 0.0818 3.6040 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3517 -1.0667 4.2426 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2034 -2.3982 3.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0835 -3.2729 2.3822 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3440 -2.5736 1.4284 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8419 3.0124 0.5314 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7883 0.4454 3.1778 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6093 -1.6106 5.3515 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 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 1 0 15 16 1 0 14 17 1 0 13 18 1 0 12 19 1 0 11 20 1 0 7 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 1 27 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 6 32 34 1 0 34 35 1 0 35 36 1 0 36 37 2 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 40 42 1 0 40 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 1 1 45 50 1 6 50 51 2 0 50 52 1 0 29 53 1 0 53 54 1 0 53 55 1 0 6 56 1 0 5 57 1 0 2 58 1 0 22 4 1 0 53 24 1 0 17 10 1 0 34 27 1 0 48 37 1 0 48 32 1 0 45 38 1 0 1 59 1 0 1 60 1 0 1 61 1 0 4 62 1 6 5 63 1 1 6 64 1 6 7 65 1 6 8 66 1 0 8 67 1 0 10 68 1 6 11 69 1 1 12 70 1 6 13 71 1 6 14 72 1 1 15 73 1 0 15 74 1 0 16 75 1 0 18 76 1 0 19 77 1 0 20 78 1 0 22 79 1 1 24 80 1 1 25 81 1 0 25 82 1 0 26 83 1 0 26 84 1 0 28 85 1 0 28 86 1 0 28 87 1 0 29 88 1 6 30 89 1 0 30 90 1 0 31 91 1 0 31 92 1 0 33 93 1 0 33 94 1 0 33 95 1 0 34 96 1 6 35 97 1 0 35 98 1 0 36 99 1 0 38100 1 1 39101 1 0 39102 1 0 41103 1 0 41104 1 0 41105 1 0 42106 1 0 42107 1 0 42108 1 0 43109 1 0 43110 1 0 44111 1 0 44112 1 0 46113 1 0 46114 1 0 47115 1 0 47116 1 0 49117 1 0 49118 1 0 49119 1 0 52120 1 0 54121 1 0 54122 1 0 54123 1 0 55124 1 0 55125 1 0 55126 1 0 56127 1 0 57128 1 0 58129 1 0 M END

Standard InCHIKey	DGJYXRGKFXEUEM-QTYUJLANSA-N
Standard InCHI	InChI=1S/C44H71NO13/c1-22(47)45-30-33(50)32(49)26(21-55-37-35(52)34(51)31(48)25(20-46)56-37)57-36(30)58-29-12-13-41(6)27(40(29,4)5)11-14-43(8)28(41)10-9-23-24-19-39(2,3)15-17-44(24,38(53)54)18-16-42(23,43)7/h9,24-37,46,48-52H,10-21H2,1-8H3,(H,45,47)(H,53,54)/t24-,25-,26-,27+,28-,29+,30-,31-,32-,33-,34+,35-,36+,37-,41+,42-,43-,44+/m1/s1
SMILES	CC(=N[C@@H]1[C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)O[C@H]1O[C@H]1CC[C@@]2(C)[C@@H](CC[C@]3(C)[C@@H]2CC=C2[C@H]4CC(C)(C)CC[C@@]4(CC[C@@]32C)C(=O)O)C1(C)C)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	821.49	Volume:	827.045 ? Van der Waals volume.
Dense:	0.993	LogP:	1.564 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.234 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.247 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	40.0
TPSA:	228.19 ? Topological Polar Surface Area.	H-Bond Acceptor:	14.0
H-Bond Donor:	8.0	Rings:	7.0
Heavy Atoms:	14.0

MedChem Properties

QED Drug-Likeness Score:	0.075	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.991	Fsp³:	0.909
MCE-18:	152.0 ? 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:	0.984	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:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.02	Promiscuous compounds:	0.097

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.865	MDCK Permeability:	-5.129
Pgp-inhibitor:	0.0	Pgp-substrate:	0.003
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):	0.232
20% Bioavailability (F20%):	0.121	30% Bioavailability (F30%):	0.907
50% Bioavailability (F50%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033	MRP1:	0.062
Plasma Protein Binding (PPB):	77.51%	Volume Distribution (VD):	-0.431
Fu:	15.806% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.034
BSEP inhibitor:	0.002

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:	0.996	CYP3A4-substrate:	0.83
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
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):

0.215

Half-life (T1/2):

2.68

ADMET: Toxicity

hERG Blockers:	0.007	hERG Blockers (10um):	0.005
Human Hepatotoxicity (H-HT):	0.995	Drug-induced Liver Injury (DILI):	0.994
AMES Toxicity:	0.888	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.008	Skin Sensitization:	1.0
Carcinogencity:	0.427	Eye Corrosion:	0.0
Eye Irritation:	0.004	Respiratory Toxicity:	0.026
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.99
Hematotoxicity:	0.569	Drug-induced Nephrotoxicity:	0.94
Genotoxicity:	0.97	RPMI-8226 Immunitoxicity:	0.028
A549 Cytotoxicity:	0.105	Hek293 Cytotoxicity:	0.156
BCF:	1.221 ? 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:	4.078 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.984 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.044 ? 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
NPO2634	Tetrapleura tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36524784]
NPO2634	Tetrapleura tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8289059]
NPO2634	Tetrapleura tetraptera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2634	Tetrapleura tetraptera	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
Activity	11

Activity Type	# Activity
Organism	11

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
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Activity	=	4.1	n.a.	PMID[26383126]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Activity	=	4.2	n.a.	PMID[18942826]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Activity	=	4.0	n.a.	PMID[18942826]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Activity	=	3.1	n.a.	PMID[19317450]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Activity	=	5.0	n.a.	PMID[18942826]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Activity	=	100.0	%	PMID[18558669]
NPT3469	Organism	Biomphalaria glabrata	Biomphalaria glabrata	Activity	=	100.0	%	PMID[12105963]

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 NPC119794 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	21264
0.1-0.2	23886
0.2-0.3	3282
0.3-0.4	873
0.4-0.5	421
0.5-0.6	58
0.6-0.7	49
0.7-0.8	0
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.866	High Similarity	NPC73829
0.8155	Intermediate Similarity	NPC280941
0.8155	Intermediate Similarity	NPC235772
0.8065	Intermediate Similarity	NPC191410
0.7524	Intermediate Similarity	NPC75318
0.7419	Intermediate Similarity	NPC606107
0.74	Intermediate Similarity	NPC127056
0.7374	Intermediate Similarity	NPC136877
0.7347	Intermediate Similarity	NPC164194
0.7238	Intermediate Similarity	NPC257468
0.7157	Intermediate Similarity	NPC472949
0.7157	Intermediate Similarity	NPC488561
0.6991	Remote Similarity	NPC219180
0.6972	Remote Similarity	NPC488564
0.6961	Remote Similarity	NPC25605
0.6893	Remote Similarity	NPC109079
0.6852	Remote Similarity	NPC79718
0.6832	Remote Similarity	NPC76999
0.6796	Remote Similarity	NPC59804
0.6792	Remote Similarity	NPC114304
0.6771	Remote Similarity	NPC204407
0.6762	Remote Similarity	NPC22956
0.6729	Remote Similarity	NPC104400
0.6729	Remote Similarity	NPC10320
0.6727	Remote Similarity	NPC324875
0.6727	Remote Similarity	NPC292677
0.6701	Remote Similarity	NPC283849
0.6696	Remote Similarity	NPC166422
0.6667	Remote Similarity	NPC139044
0.6636	Remote Similarity	NPC145899
0.6635	Remote Similarity	NPC56713
0.6574	Remote Similarity	NPC180550
0.6574	Remote Similarity	NPC35405
0.6549	Remote Similarity	NPC62725
0.6535	Remote Similarity	NPC284807
0.6491	Remote Similarity	NPC288205
0.6491	Remote Similarity	NPC51465
0.6441	Remote Similarity	NPC54636
0.6429	Remote Similarity	NPC323359
0.6389	Remote Similarity	NPC469945
0.6381	Remote Similarity	NPC12288
0.6346	Remote Similarity	NPC270667
0.6296	Remote Similarity	NPC80843
0.6293	Remote Similarity	NPC200788
0.6271	Remote Similarity	NPC251263
0.6238	Remote Similarity	NPC31839
0.62	Remote Similarity	NPC28198
0.62	Remote Similarity	NPC476123
0.6195	Remote Similarity	NPC276093
0.6186	Remote Similarity	NPC323341
0.6186	Remote Similarity	NPC243680
0.6179	Remote Similarity	NPC161717
0.6168	Remote Similarity	NPC174679
0.6168	Remote Similarity	NPC279554
0.6161	Remote Similarity	NPC481082
0.6161	Remote Similarity	NPC164419
0.6095	Remote Similarity	NPC475472
0.6078	Remote Similarity	NPC286347
0.6071	Remote Similarity	NPC471383
0.6055	Remote Similarity	NPC488516
0.6	Remote Similarity	NPC291903
0.5909	Remote Similarity	NPC6377
0.5909	Remote Similarity	NPC208381
0.5865	Remote Similarity	NPC100383
0.5841	Remote Similarity	NPC473383
0.5826	Remote Similarity	NPC488515
0.5818	Remote Similarity	NPC114441
0.5798	Remote Similarity	NPC475119
0.5794	Remote Similarity	NPC471385
0.5785	Remote Similarity	NPC133818
0.5763	Remote Similarity	NPC475486
0.575	Remote Similarity	NPC473824
0.5714	Remote Similarity	NPC242611
0.5691	Remote Similarity	NPC475140
0.5684	Remote Similarity	NPC120840
0.5667	Remote Similarity	NPC476992
0.5656	Remote Similarity	NPC471384
0.5625	Remote Similarity	NPC470512
0.5607	Remote Similarity	NPC473538
0.5545	Remote Similarity	NPC48499
0.5455	Remote Similarity	NPC480939
0.5455	Remote Similarity	NPC210729
0.5455	Remote Similarity	NPC82931
0.5448	Remote Similarity	NPC120667
0.5448	Remote Similarity	NPC278272
0.5431	Remote Similarity	NPC173859
0.5429	Remote Similarity	NPC57362
0.5417	Remote Similarity	NPC488209
0.541	Remote Similarity	NPC172365
0.5398	Remote Similarity	NPC480424
0.5385	Remote Similarity	NPC63159
0.5364	Remote Similarity	NPC475611
0.5339	Remote Similarity	NPC470514
0.5333	Remote Similarity	NPC481079
0.5328	Remote Similarity	NPC470915
0.5323	Remote Similarity	NPC151543
0.5321	Remote Similarity	NPC294112
0.5321	Remote Similarity	NPC475633
0.5317	Remote Similarity	NPC470218
0.5299	Remote Similarity	NPC251768
0.5267	Remote Similarity	NPC111466
0.5225	Remote Similarity	NPC473481
0.521	Remote Similarity	NPC470513
0.5207	Remote Similarity	NPC301449
0.5207	Remote Similarity	NPC601290
0.5169	Remote Similarity	NPC148603
0.5167	Remote Similarity	NPC484832
0.5128	Remote Similarity	NPC192791
0.5115	Remote Similarity	NPC258617
0.5052	Remote Similarity	NPC480946
0.5052	Remote Similarity	NPC130577
0.5052	Remote Similarity	NPC142415
0.5052	Remote Similarity	NPC102683
0.505	Remote Similarity	NPC296164
0.5043	Remote Similarity	NPC263756
0.5043	Remote Similarity	NPC108748
0.5043	Remote Similarity	NPC213674
0.5043	Remote Similarity	NPC469946
0.5041	Remote Similarity	NPC64715

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC119794 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6195
0.1-0.2	2868
0.2-0.3	77
0.3-0.4	9
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
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
		NPD

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