NPASS Compound

Natural Product: NPC328506

Natural Product ID	NPC328506
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	CGORMVKERVDQKF-PHTWDIKASA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5321830
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 138146 0 0 0 0 0 0 0 0999 V2000 14.1005 -1.2859 0.7152 C 0 0 0 0 0 0 0 0 0 0 0 0 12.6660 -1.4970 0.2992 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7630 -1.5417 1.5030 C 0 0 0 0 0 0 0 0 0 0 0 0 10.7317 -0.4054 1.4747 C 0 0 0 0 0 0 0 0 0 0 0 0 10.0043 -0.5262 0.1544 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1111 0.6678 -0.1034 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9566 0.0943 -0.8062 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1875 -1.4002 -0.7208 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1226 -1.5972 0.2736 O 0 0 0 0 0 0 0 0 0 0 0 0 6.8300 -2.0234 -0.3529 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9091 -0.9151 -0.7619 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6020 0.2778 -0.1171 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9360 1.5486 -0.5386 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5234 1.3151 -1.0572 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8935 0.2952 -0.1324 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4794 -1.0649 -0.4903 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0893 -2.1552 0.4474 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7849 -1.7666 1.1137 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9297 -1.1400 0.0379 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4100 0.2784 -0.1880 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8305 0.7202 -1.5026 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5751 0.0193 -1.8913 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2650 -0.4985 -0.7916 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4873 -1.0682 0.3796 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2474 0.4092 -0.3765 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5341 0.0040 -0.6122 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3831 0.9532 -1.3921 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7527 2.1932 -0.5862 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2942 1.6995 0.7334 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1867 0.8669 1.3436 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1052 -0.3013 0.6382 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3769 0.6728 2.8257 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4430 1.9399 3.4410 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3931 0.9006 0.4180 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.5523 1.3151 1.0409 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7038 1.6292 0.1572 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6845 2.4587 1.0220 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.9033 1.6886 2.2783 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2461 0.3524 2.3120 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9387 0.3022 1.9131 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2511 -0.0800 3.7919 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7420 -1.3695 3.9156 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.2967 1.4562 2.3821 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0328 3.6583 1.3398 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.3799 0.4820 -0.2587 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6438 0.4399 -1.6065 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0715 -0.8112 -2.2098 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6024 -1.9869 -1.3784 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0974 -1.8284 -1.1764 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.6513 -0.6941 -2.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0046 0.4954 -1.8896 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.0894 -0.4567 -1.5135 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.8507 -1.6092 -1.5846 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.6788 -3.0008 -1.6510 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2591 -3.1988 -1.9340 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.6807 -0.7936 -2.1473 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.6836 2.9287 -1.3130 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6632 1.3963 -2.4975 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8471 -1.0188 -2.8202 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8698 1.2367 0.8575 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7929 0.1429 1.3442 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8132 1.6729 -1.0184 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8546 -0.6640 -0.9246 O 0 0 0 0 0 0 0 0 0 0 0 0 12.1837 -0.3802 -0.6164 C 0 0 0 0 0 0 0 0 0 0 0 0 14.2511 -0.2114 0.8830 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2606 -1.8918 1.6272 H 0 0 0 0 0 0 0 0 0 0 0 0 14.7612 -1.6765 -0.1015 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6193 -2.4396 -0.3156 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3467 -1.4939 2.4432 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1592 -2.4750 1.5190 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1832 0.5695 1.6503 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0459 -0.6206 2.3073 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9165 1.2157 0.8301 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8182 0.4360 -1.8560 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5302 -1.7883 -1.7132 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6835 -2.9021 -0.9929 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8270 -2.2419 0.7337 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0956 -0.7696 -1.8704 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8434 2.2051 0.3642 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5227 2.1292 -1.2800 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5523 0.9874 -2.1156 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9724 2.2672 -0.9223 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1898 0.6167 0.9054 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9622 -1.3170 -1.4696 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8591 -3.1107 -0.1130 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8600 -2.4479 1.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2508 -2.6136 1.5632 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9719 -1.0076 1.9278 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0406 -1.7636 -0.8619 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5927 0.4889 -2.2939 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7334 1.8346 -1.5061 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0184 0.7441 -2.4872 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8558 -1.3640 -1.2229 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2730 -0.3969 1.2526 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0935 -2.0735 0.6985 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5112 -0.9691 -1.1406 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2939 0.4673 -1.7657 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8034 2.7541 -0.4394 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5817 2.5326 1.4170 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2062 1.3946 1.2277 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2475 0.0455 3.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4862 0.1797 3.2635 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6187 2.4299 3.2132 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3862 2.2086 1.6888 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5170 2.2506 -0.7131 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6089 2.6109 0.4423 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6248 2.2316 3.2074 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8427 -0.4598 1.8103 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2655 -0.0224 4.2142 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5685 0.5969 4.3511 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1933 -1.5891 3.1075 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4958 0.8160 1.6257 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7320 3.6257 2.2812 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2134 1.3450 -2.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4155 -0.9175 -3.2666 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1266 -1.8895 -0.3810 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.3573 -1.7426 -0.1019 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7597 -1.0118 -3.0597 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5405 0.4025 -2.0358 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0050 -0.1887 -0.4283 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.8011 -1.4018 -1.7784 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3546 -3.3017 -1.0185 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5217 -3.2099 -2.8968 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3663 -1.6677 -2.5029 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4577 2.8268 -2.2927 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1876 2.2150 -2.2479 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2653 -1.8147 -2.6000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6411 2.0607 0.9407 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8430 0.7637 1.8410 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9536 1.7547 0.5441 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6370 1.1727 1.7882 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7801 -0.2670 1.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0599 -0.4927 1.8806 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4279 1.0975 -1.7369 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4052 2.3937 -0.4185 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0602 2.2224 -1.6218 H 0 0 0 0 0 0 0 0 0 0 0 0 12.3117 0.5544 -0.0722 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7682 -0.3281 -1.5573 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 7 8 1 0 8 9 1 0 8 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 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 41 42 1 0 38 43 1 0 37 44 1 0 36 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 49 54 1 0 48 55 1 0 47 56 1 0 28 57 1 0 27 58 1 0 22 59 1 0 20 60 1 0 12 61 1 0 6 62 1 0 5 63 1 0 63 64 1 0 64 2 1 0 9 5 1 0 12 7 1 0 16 11 1 0 20 15 1 0 24 19 1 0 31 26 1 0 40 35 1 0 51 46 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 0 3 69 1 0 3 70 1 0 4 71 1 0 4 72 1 0 6 73 1 0 7 74 1 0 8 75 1 0 10 76 1 0 10 77 1 0 11 78 1 0 13 79 1 0 13 80 1 0 14 81 1 0 14 82 1 0 15 83 1 0 16 84 1 0 17 85 1 0 17 86 1 0 18 87 1 0 18 88 1 0 19 89 1 0 21 90 1 0 21 91 1 0 22 92 1 0 23 93 1 0 24 94 1 0 24 95 1 0 26 96 1 0 27 97 1 0 28 98 1 0 29 99 1 0 30100 1 0 32101 1 0 32102 1 0 33103 1 0 35104 1 0 36105 1 0 37106 1 0 38107 1 0 39108 1 0 41109 1 0 41110 1 0 42111 1 0 43112 1 0 44113 1 0 46114 1 0 47115 1 0 48116 1 0 49117 1 0 50118 1 0 52119 1 0 52120 1 0 53121 1 0 54122 1 0 55123 1 0 56124 1 0 57125 1 0 58126 1 0 59127 1 0 60128 1 0 60129 1 0 60130 1 0 61131 1 0 61132 1 0 61133 1 0 62134 1 0 62135 1 0 62136 1 0 64137 1 0 64138 1 0 M END

Standard InCHIKey	CGORMVKERVDQKF-PHTWDIKASA-N
Standard InCHI	InChI=1S/C45H74O19/c1-18-7-10-45(57-17-18)19(2)30-26(64-45)12-23-21-6-5-20-11-25(24(49)13-44(20,4)22(21)8-9-43(23,30)3)58-40-37(56)35(54)38(29(16-48)61-40)62-42-39(34(53)32(51)28(15-47)60-42)63-41-36(55)33(52)31(50)27(14-46)59-41/h18-42,46-56H,5-17H2,1-4H3/t18?,19-,20-,21+,22-,23-,24?,25+,26-,27+,28+,29+,30-,31-,32+,33-,34-,35+,36+,37+,38-,39+,40+,41-,42-,43-,44-,45+/m0/s1
SMILES	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CC(C(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)O)OC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)C)C)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	918.48	Volume:	876.882 ? Van der Waals volume.
Dense:	1.047	LogP:	0.266 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.25 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.709 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	48.0
TPSA:	296.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	11.0	Rings:	9.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.114	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.806	Fsp³:	1.0
MCE-18:	234.511 ? 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:	0.001	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.045 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.235 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.427	Promiscuous compounds:	0.003

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.008	MDCK Permeability:	-4.77
Pgp-inhibitor:	0.0	Pgp-substrate:	0.815
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):	0.99
20% Bioavailability (F20%):	0.166	30% Bioavailability (F30%):	0.996
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.22	MRP1:	1.0
Plasma Protein Binding (PPB):	43.789%	Volume Distribution (VD):	-0.484
Fu:	37.433% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.034	BCRP inhibitor:	0.002
BSEP inhibitor:	0.146

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.434	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.981	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):

-0.172

Half-life (T1/2):

3.712

ADMET: Toxicity

hERG Blockers:	0.041	hERG Blockers (10um):	0.388
Human Hepatotoxicity (H-HT):	0.64	Drug-induced Liver Injury (DILI):	0.357
AMES Toxicity:	0.412	Rat Oral Acute Toxicity:	0.112
Maximum Recommended Daily Dose:	0.225	Skin Sensitization:	0.02
Carcinogencity:	0.061	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.002
Drug-induced Neurotoxicity:	0.487	Ototoxicity:	1.0
Hematotoxicity:	0.007	Drug-induced Nephrotoxicity:	0.014
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.123
A549 Cytotoxicity:	0.035	Hek293 Cytotoxicity:	0.806
BCF:	1.234 ? 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:	3.839 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.818 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.287 ? 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]
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]
NPO7395	Tribulus terrestris	Species	Zygophyllaceae	Eukaryota	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 NPC328506 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	28259
0.1-0.2	18496
0.2-0.3	2525
0.3-0.4	379
0.4-0.5	83
0.5-0.6	71
0.6-0.7	24
0.7-0.8	1
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8916	High Similarity	NPC294686
0.8488	Intermediate Similarity	NPC222731
0.8315	Intermediate Similarity	NPC107962
0.7935	Intermediate Similarity	NPC195297
0.7755	Intermediate Similarity	NPC115165
0.7692	Intermediate Similarity	NPC54619
0.7549	Intermediate Similarity	NPC83137
0.7528	Intermediate Similarity	NPC297348
0.7528	Intermediate Similarity	NPC249204
0.7528	Intermediate Similarity	NPC48339
0.7528	Intermediate Similarity	NPC141769
0.7528	Intermediate Similarity	NPC477547
0.7333	Intermediate Similarity	NPC325828
0.7174	Intermediate Similarity	NPC477451
0.7048	Intermediate Similarity	NPC470862
0.7021	Intermediate Similarity	NPC121453
0.7019	Intermediate Similarity	NPC232611
0.7	Intermediate Similarity	NPC92890
0.7	Intermediate Similarity	NPC477809
0.697	Remote Similarity	NPC473601
0.6923	Remote Similarity	NPC475625
0.6771	Remote Similarity	NPC211354
0.6762	Remote Similarity	NPC473518
0.6735	Remote Similarity	NPC6295
0.6635	Remote Similarity	NPC184617
0.6476	Remote Similarity	NPC97700
0.6476	Remote Similarity	NPC30856
0.6429	Remote Similarity	NPC19400
0.6392	Remote Similarity	NPC250393
0.6339	Remote Similarity	NPC470867
0.6327	Remote Similarity	NPC206003
0.6327	Remote Similarity	NPC473610
0.6275	Remote Similarity	NPC160426
0.6263	Remote Similarity	NPC107188
0.6216	Remote Similarity	NPC132080
0.6186	Remote Similarity	NPC234352
0.6117	Remote Similarity	NPC113044
0.6117	Remote Similarity	NPC283829
0.6117	Remote Similarity	NPC161676
0.6116	Remote Similarity	NPC481190
0.6075	Remote Similarity	NPC151134
0.6018	Remote Similarity	NPC31896
0.6	Remote Similarity	NPC24960
0.5946	Remote Similarity	NPC232037
0.5935	Remote Similarity	NPC330026
0.5926	Remote Similarity	NPC128572
0.5922	Remote Similarity	NPC485595
0.5905	Remote Similarity	NPC475351
0.5893	Remote Similarity	NPC470864
0.5865	Remote Similarity	NPC141433
0.5856	Remote Similarity	NPC470861
0.5856	Remote Similarity	NPC32361
0.5856	Remote Similarity	NPC116756
0.5818	Remote Similarity	NPC51520
0.5818	Remote Similarity	NPC303069
0.5798	Remote Similarity	NPC210569
0.578	Remote Similarity	NPC480555
0.578	Remote Similarity	NPC150372
0.5769	Remote Similarity	NPC470432
0.5769	Remote Similarity	NPC230507
0.5714	Remote Similarity	NPC485594
0.5688	Remote Similarity	NPC471464
0.5684	Remote Similarity	NPC277715
0.5648	Remote Similarity	NPC475643
0.5641	Remote Similarity	NPC470866
0.5625	Remote Similarity	NPC475550
0.5517	Remote Similarity	NPC233433
0.5517	Remote Similarity	NPC480553
0.5517	Remote Similarity	NPC477811
0.5505	Remote Similarity	NPC470433
0.5505	Remote Similarity	NPC46190
0.5505	Remote Similarity	NPC171073
0.55	Remote Similarity	NPC181845
0.5487	Remote Similarity	NPC269297
0.5487	Remote Similarity	NPC222202
0.5481	Remote Similarity	NPC306131
0.5481	Remote Similarity	NPC200802
0.5478	Remote Similarity	NPC92710
0.5472	Remote Similarity	NPC125324
0.5446	Remote Similarity	NPC177834
0.5437	Remote Similarity	NPC474399
0.5431	Remote Similarity	NPC476112
0.5431	Remote Similarity	NPC307534
0.5408	Remote Similarity	NPC473774
0.5408	Remote Similarity	NPC481419
0.5408	Remote Similarity	NPC481417
0.5405	Remote Similarity	NPC6806
0.5345	Remote Similarity	NPC480554
0.5344	Remote Similarity	NPC329820
0.5328	Remote Similarity	NPC220836
0.528	Remote Similarity	NPC263359
0.5268	Remote Similarity	NPC300557
0.5243	Remote Similarity	NPC291203
0.5243	Remote Similarity	NPC217205
0.5172	Remote Similarity	NPC475333
0.5172	Remote Similarity	NPC13193
0.5172	Remote Similarity	NPC224098
0.5172	Remote Similarity	NPC208383
0.5133	Remote Similarity	NPC51172
0.5133	Remote Similarity	NPC49032
0.5128	Remote Similarity	NPC194207
0.5128	Remote Similarity	NPC22779
0.5122	Remote Similarity	NPC477807
0.5102	Remote Similarity	NPC144790
0.5102	Remote Similarity	NPC149400
0.51	Remote Similarity	NPC481420
0.51	Remote Similarity	NPC481421
0.5089	Remote Similarity	NPC602423
0.5082	Remote Similarity	NPC94086
0.5082	Remote Similarity	NPC473817
0.5056	Remote Similarity	NPC227260
0.5044	Remote Similarity	NPC248746
0.5041	Remote Similarity	NPC480556
0.5039	Remote Similarity	NPC244431

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC328506 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7803
0.1-0.2	1265
0.2-0.3	75
0.3-0.4	3
0.4-0.5	2
0.5-0.6	0
0.6-0.7	1
0.7-0.8	1
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
0.7333	Intermediate Similarity	NPD8171	Phase 2
0.64	Remote Similarity	NPD8170	Phase 2

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