NPASS Compound

Natural Product: NPC141744

Natural Product ID	NPC141744
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	TVXISIJXIXGTQS-PNVPXRELSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	441918
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 133140 0 0 0 0 0 0 0 0999 V2000 9.1697 -1.2794 3.1091 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8520 -0.3285 1.9382 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3299 1.0293 2.4128 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7073 -0.8258 0.8108 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3931 -0.1627 -0.5184 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9405 -0.2211 -0.8572 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0899 -0.7489 0.2741 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3833 -0.2945 1.6414 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7039 -0.6043 -0.2097 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9976 -1.7088 -0.2157 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5908 -1.8453 -0.6510 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9867 -0.5015 -0.3026 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5098 -0.5908 -0.2344 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8716 -1.3526 -1.3659 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1671 -1.4062 1.0258 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1817 -0.7464 1.9138 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0067 -0.1152 1.2593 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5118 0.8645 0.2353 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3481 0.8671 -0.9946 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7033 2.2678 0.8554 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9532 0.7526 0.0024 C 0 0 2 0 0 0 0 0 0 0 0 0 1.4013 1.6215 -1.1376 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9042 1.8294 -0.9147 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6584 0.5157 -1.1379 C 0 0 2 0 0 0 0 0 0 0 0 0 3.5681 0.2687 -2.6230 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0958 0.6416 -0.6707 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1543 1.8005 0.2814 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0076 1.1220 -1.8160 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4627 1.0451 -1.4866 C 0 0 1 0 0 0 0 0 0 0 0 0 8.0017 2.2182 -0.9680 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9401 -1.0284 0.7823 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1291 -1.0021 1.4486 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2683 -0.8437 0.4234 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8070 -2.1966 0.0359 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5870 -3.1031 -0.2000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8505 -3.1962 1.1133 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3226 -2.2701 2.0394 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8294 -2.5819 -1.2262 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4383 -2.0796 -1.2017 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2436 -0.0001 0.9954 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3742 1.1797 0.2438 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7800 1.4104 -0.2295 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.7423 2.6109 -1.1380 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.1663 3.7740 -0.3752 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.6907 3.3078 0.9726 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8259 2.2425 0.9450 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2150 4.6668 -0.1410 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9858 2.9325 -1.6855 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2862 0.2990 -0.9052 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.4034 -0.2253 -0.2467 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.6388 -0.2892 -1.0764 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6112 -1.2339 -0.3649 C 0 0 2 0 0 0 0 0 0 0 0 0 -10.3340 -1.1981 1.1325 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9634 -1.8207 1.3218 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1055 -1.4919 0.2773 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2577 -2.0206 1.7743 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.3967 -2.5029 -0.8854 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2524 0.9572 -1.1164 O 0 0 0 0 0 0 0 0 0 0 0 0 7.7981 -1.2659 -1.9437 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8249 -1.8490 -2.3651 O 0 0 0 0 0 0 0 0 0 0 0 0 6.6043 -1.6151 -2.4985 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7144 -2.2860 2.8917 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6345 -0.8921 3.9987 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2521 -1.3373 3.2331 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1385 1.3669 1.7124 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4993 1.7885 2.3185 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7551 1.0168 3.4136 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7569 -0.6513 1.0644 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5311 -1.9201 0.7072 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0213 -0.7696 -1.2505 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8685 0.8341 -0.6147 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4040 -1.8472 0.3124 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9870 0.6440 2.0024 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9116 -1.0519 2.3506 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4296 -2.6748 0.1248 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0536 -2.6804 -0.1823 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5953 -2.0508 -1.7396 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3093 -0.2715 0.7635 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4756 -0.7449 -2.1760 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0252 -1.9378 -0.9929 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5805 -2.1488 -1.6722 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8062 -2.4191 0.7862 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0919 -1.5826 1.6509 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6712 0.0517 2.5440 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1534 -1.5096 2.6550 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5446 0.4134 2.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3005 1.4270 -0.7534 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8831 1.4703 -1.8032 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6754 -0.1072 -1.3582 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7283 3.0513 0.1012 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6686 2.2602 1.4144 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0906 2.3961 1.6325 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4577 1.1617 0.9253 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9541 2.6326 -0.9722 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1237 1.3041 -2.1275 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1470 2.6115 -1.6249 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9058 2.1360 0.1641 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8909 1.1701 -3.2178 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1429 -0.5647 -3.0075 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5278 0.1209 -2.9716 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1791 2.2133 0.4470 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7390 2.6710 -0.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5690 1.7188 1.1802 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8377 2.2058 -2.0044 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7838 0.5957 -2.7619 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9670 1.0447 -2.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4651 2.1648 -0.1315 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2029 -0.2473 2.2540 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8950 -0.3463 -0.4882 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4698 -2.6418 0.7942 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9200 -4.1119 -0.5082 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8482 -4.2307 1.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7685 -2.9782 0.8669 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2993 -1.8680 -1.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0351 -2.8825 -1.3246 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7171 1.0880 -0.6728 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4183 1.6161 0.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0142 2.3387 -1.9639 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3218 4.2648 -0.9027 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5415 3.0448 1.6676 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1049 4.1442 1.4825 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8820 5.6147 -0.1184 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.9880 3.8663 -1.9691 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5888 0.4135 0.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4748 -0.6826 -2.0917 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6632 -0.9732 -0.5675 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4016 -0.1903 1.5408 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0832 -2.9012 1.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5290 -1.3738 2.2468 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1875 -1.8055 1.5159 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4925 -2.6143 -1.2206 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1736 1.2911 -2.0526 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4370 -2.5362 -2.9039 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 7 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 6 13 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 18 20 1 0 18 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 6 24 26 1 0 26 27 1 1 26 28 1 0 28 29 1 0 29 30 1 0 17 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 35 38 1 0 34 39 1 0 33 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 45 46 1 0 44 47 1 0 43 48 1 0 42 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 52 57 1 0 51 58 1 0 6 59 1 6 59 60 2 0 59 61 1 0 8 2 1 0 26 9 1 0 37 32 1 0 46 41 1 0 55 50 1 0 29 6 1 0 24 12 1 0 21 13 1 0 1 62 1 0 1 63 1 0 1 64 1 0 3 65 1 0 3 66 1 0 3 67 1 0 4 68 1 0 4 69 1 0 5 70 1 0 5 71 1 0 7 72 1 1 8 73 1 0 8 74 1 0 10 75 1 0 11 76 1 0 11 77 1 0 12 78 1 1 14 79 1 0 14 80 1 0 14 81 1 0 15 82 1 0 15 83 1 0 16 84 1 0 16 85 1 0 17 86 1 1 19 87 1 0 19 88 1 0 19 89 1 0 20 90 1 0 20 91 1 0 20 92 1 0 21 93 1 1 22 94 1 0 22 95 1 0 23 96 1 0 23 97 1 0 25 98 1 0 25 99 1 0 25100 1 0 27101 1 0 27102 1 0 27103 1 0 28104 1 0 28105 1 0 29106 1 6 30107 1 0 32108 1 1 33109 1 6 34110 1 1 35111 1 6 36112 1 0 36113 1 0 38114 1 0 39115 1 0 41116 1 6 42117 1 1 43118 1 6 44119 1 6 45120 1 0 45121 1 0 47122 1 0 48123 1 0 50124 1 1 51125 1 6 52126 1 1 53127 1 1 54128 1 0 54129 1 0 56130 1 0 57131 1 0 58132 1 0 61133 1 0 M END

Standard InCHIKey	TVXISIJXIXGTQS-PNVPXRELSA-N
Standard InCHI	InChI=1S/C45H72O16/c1-40(2)14-15-45(39(54)55)22(16-40)21-8-9-27-42(5)12-11-29(41(3,4)26(42)10-13-43(27,6)44(21,7)17-28(45)49)59-37-34(31(51)24(47)19-57-37)61-38-35(32(52)25(48)20-58-38)60-36-33(53)30(50)23(46)18-56-36/h8,22-38,46-53H,9-20H2,1-7H3,(H,54,55)/t22-,23-,24-,25-,26-,27+,28+,29-,30-,31-,32-,33+,34+,35+,36-,37-,38-,42-,43+,44+,45+/m0/s1
SMILES	CC1(C)CC[C@]2([C@@H](C1)C1=CC[C@@H]3[C@@]4(C)CC[C@@H](C(C)(C)[C@@H]4CC[C@@]3(C)[C@]1(C)C[C@H]2O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O[C@H]1[C@@H]([C@H]([C@H](CO1)O)O)O)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	868.48	Volume:	853.795 ? Van der Waals volume.
Dense:	1.017	LogP:	2.107 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.76 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.662 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	45.0
TPSA:	254.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	8.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.13	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.227	Fsp³:	0.933
MCE-18:	171.08 ? 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:	0.792	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.014 ? 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:	0.19	Promiscuous compounds:	0.105

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.02	MDCK Permeability:	-5.084
Pgp-inhibitor:	0.0	Pgp-substrate:	0.189
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):	0.042
20% Bioavailability (F20%):	0.688	30% Bioavailability (F30%):	0.73
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.014	MRP1:	0.703
Plasma Protein Binding (PPB):	71.666%	Volume Distribution (VD):	-0.516
Fu:	20.075% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.991	BCRP inhibitor:	0.005
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.008
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.59
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.006
HLM stability:	0.014 ? 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):

0.329

Half-life (T1/2):

2.039

ADMET: Toxicity

hERG Blockers:	0.002	hERG Blockers (10um):	0.006
Human Hepatotoxicity (H-HT):	0.838	Drug-induced Liver Injury (DILI):	0.974
AMES Toxicity:	0.947	Rat Oral Acute Toxicity:	0.044
Maximum Recommended Daily Dose:	0.012	Skin Sensitization:	1.0
Carcinogencity:	0.57	Eye Corrosion:	0.0
Eye Irritation:	0.057	Respiratory Toxicity:	0.271
Drug-induced Neurotoxicity:	0.005	Ototoxicity:	0.984
Hematotoxicity:	0.923	Drug-induced Nephrotoxicity:	0.999
Genotoxicity:	0.652	RPMI-8226 Immunitoxicity:	0.177
A549 Cytotoxicity:	0.962	Hek293 Cytotoxicity:	0.524
BCF:	1.112 ? 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:	3.657 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.29 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.327 ? 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
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[11141122]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28769	Albizzia anthelmintica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28769	Albizzia anthelmintica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28769	Albizzia anthelmintica	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	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 NPC141744 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	22174
0.1-0.2	23378
0.2-0.3	3000
0.3-0.4	795
0.4-0.5	344
0.5-0.6	104
0.6-0.7	33
0.7-0.8	0
0.8-0.85	2
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8778	High Similarity	NPC80843
0.8617	High Similarity	NPC488515
0.8588	High Similarity	NPC242611
0.8283	Intermediate Similarity	NPC288205
0.8283	Intermediate Similarity	NPC51465
0.79	Intermediate Similarity	NPC475486
0.7872	Intermediate Similarity	NPC488516
0.7525	Intermediate Similarity	NPC75318
0.74	Intermediate Similarity	NPC481082
0.74	Intermediate Similarity	NPC164419
0.7396	Intermediate Similarity	NPC127056
0.732	Intermediate Similarity	NPC488561
0.7292	Intermediate Similarity	NPC56713
0.7253	Intermediate Similarity	NPC31839
0.7238	Intermediate Similarity	NPC475119
0.7216	Intermediate Similarity	NPC480424
0.72	Intermediate Similarity	NPC104400
0.72	Intermediate Similarity	NPC10320
0.7033	Intermediate Similarity	NPC283849
0.7009	Intermediate Similarity	NPC200788
0.7	Intermediate Similarity	NPC469945
0.6923	Remote Similarity	NPC37134
0.6857	Remote Similarity	NPC291903
0.6852	Remote Similarity	NPC473824
0.6822	Remote Similarity	NPC280941
0.6822	Remote Similarity	NPC235772
0.6768	Remote Similarity	NPC59804
0.6698	Remote Similarity	NPC324875
0.6698	Remote Similarity	NPC292677
0.66	Remote Similarity	NPC174679
0.66	Remote Similarity	NPC279554
0.6577	Remote Similarity	NPC243680
0.6509	Remote Similarity	NPC79718
0.6465	Remote Similarity	NPC76999
0.6449	Remote Similarity	NPC145899
0.6372	Remote Similarity	NPC166422
0.6372	Remote Similarity	NPC219180
0.6316	Remote Similarity	NPC28198
0.6316	Remote Similarity	NPC476123
0.63	Remote Similarity	NPC164194
0.6264	Remote Similarity	NPC601365
0.6262	Remote Similarity	NPC73829
0.6228	Remote Similarity	NPC251263
0.6154	Remote Similarity	NPC472949
0.6154	Remote Similarity	NPC6377
0.6154	Remote Similarity	NPC208381
0.6147	Remote Similarity	NPC276093
0.6122	Remote Similarity	NPC100383
0.6117	Remote Similarity	NPC25605
0.6111	Remote Similarity	NPC257468
0.6034	Remote Similarity	NPC283417
0.6034	Remote Similarity	NPC200049
0.6	Remote Similarity	NPC120667
0.6	Remote Similarity	NPC278272
0.5979	Remote Similarity	NPC606107
0.5909	Remote Similarity	NPC484832
0.5893	Remote Similarity	NPC488564
0.5893	Remote Similarity	NPC488209
0.5868	Remote Similarity	NPC161717
0.5862	Remote Similarity	NPC323341
0.5833	Remote Similarity	NPC114304
0.5798	Remote Similarity	NPC4749
0.5794	Remote Similarity	NPC22956
0.578	Remote Similarity	NPC488526
0.5778	Remote Similarity	NPC228784
0.5778	Remote Similarity	NPC324341
0.5778	Remote Similarity	NPC601810
0.5766	Remote Similarity	NPC119794
0.5763	Remote Similarity	NPC475140
0.5755	Remote Similarity	NPC109079
0.5726	Remote Similarity	NPC133818
0.5702	Remote Similarity	NPC265841
0.5702	Remote Similarity	NPC488308
0.5664	Remote Similarity	NPC301449
0.5664	Remote Similarity	NPC601290
0.5656	Remote Similarity	NPC312650
0.5652	Remote Similarity	NPC480939
0.5593	Remote Similarity	NPC471384
0.5586	Remote Similarity	NPC139044
0.5566	Remote Similarity	NPC12288
0.5565	Remote Similarity	NPC104137
0.5565	Remote Similarity	NPC26626
0.5565	Remote Similarity	NPC481078
0.5556	Remote Similarity	NPC488309
0.5545	Remote Similarity	NPC286347
0.5545	Remote Similarity	NPC117714
0.5537	Remote Similarity	NPC488211
0.5528	Remote Similarity	NPC271610
0.5517	Remote Similarity	NPC62725
0.5505	Remote Similarity	NPC469946
0.5495	Remote Similarity	NPC164389
0.5495	Remote Similarity	NPC232237
0.5484	Remote Similarity	NPC471385
0.5455	Remote Similarity	NPC54636
0.5455	Remote Similarity	NPC112352
0.5446	Remote Similarity	NPC63159
0.5446	Remote Similarity	NPC471383
0.5426	Remote Similarity	NPC222047
0.5421	Remote Similarity	NPC136877
0.5405	Remote Similarity	NPC30289
0.54	Remote Similarity	NPC204407
0.5391	Remote Similarity	NPC323359
0.5385	Remote Similarity	NPC210729
0.5385	Remote Similarity	NPC82931
0.5377	Remote Similarity	NPC127853
0.5366	Remote Similarity	NPC21691
0.5364	Remote Similarity	NPC263756
0.5357	Remote Similarity	NPC180550
0.5357	Remote Similarity	NPC35405
0.5351	Remote Similarity	NPC64715
0.5333	Remote Similarity	NPC284449
0.5333	Remote Similarity	NPC191410
0.5299	Remote Similarity	NPC187290
0.5294	Remote Similarity	NPC177246
0.5289	Remote Similarity	NPC123199
0.5285	Remote Similarity	NPC71391
0.5283	Remote Similarity	NPC480938
0.5263	Remote Similarity	NPC297263
0.5259	Remote Similarity	NPC218954
0.5259	Remote Similarity	NPC23275
0.5238	Remote Similarity	NPC284807
0.5234	Remote Similarity	NPC1046
0.5229	Remote Similarity	NPC475296
0.5229	Remote Similarity	NPC309780
0.5229	Remote Similarity	NPC474589
0.5225	Remote Similarity	NPC213674
0.5221	Remote Similarity	NPC480475
0.5217	Remote Similarity	NPC302887
0.5214	Remote Similarity	NPC480473
0.5214	Remote Similarity	NPC160452
0.5214	Remote Similarity	NPC480474
0.5213	Remote Similarity	NPC201657
0.5194	Remote Similarity	NPC488212
0.5182	Remote Similarity	NPC114441
0.5175	Remote Similarity	NPC105800
0.5169	Remote Similarity	NPC207738
0.5169	Remote Similarity	NPC31838
0.5161	Remote Similarity	NPC85154
0.5161	Remote Similarity	NPC192765
0.514	Remote Similarity	NPC475472
0.5126	Remote Similarity	NPC11242
0.5124	Remote Similarity	NPC151543
0.512	Remote Similarity	NPC178264
0.5118	Remote Similarity	NPC476779
0.5093	Remote Similarity	NPC270667
0.5088	Remote Similarity	NPC44716
0.5088	Remote Similarity	NPC251768
0.5085	Remote Similarity	NPC187618
0.5083	Remote Similarity	NPC172365
0.5083	Remote Similarity	NPC185466
0.5079	Remote Similarity	NPC286457
0.5079	Remote Similarity	NPC476774
0.5079	Remote Similarity	NPC476780
0.5078	Remote Similarity	NPC110700
0.5076	Remote Similarity	NPC489209
0.5041	Remote Similarity	NPC313110
0.5041	Remote Similarity	NPC610204
0.5039	Remote Similarity	NPC302543

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC141744 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6667
0.1-0.2	2432
0.2-0.3	44
0.3-0.4	5
0.4-0.5	2
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