NPASS Compound

Natural Product: NPC56325

Natural Product ID	NPC56325
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VGWBUQPQZOSEEG-UROMMIOCSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal saponins

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 136144 0 0 0 0 0 0 0 0999 V2000 12.7751 -0.6104 -2.3810 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8987 -0.4717 -1.1553 C 0 0 2 0 0 0 0 0 0 0 0 0 11.1117 -1.7539 -1.0037 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7195 -1.5160 -1.5126 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0271 -0.3355 -0.8827 C 0 0 2 0 0 0 0 0 0 0 0 0 8.2784 -0.7619 0.3773 C 0 0 1 0 0 0 0 0 0 0 0 0 9.1762 -0.7484 1.5723 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2262 0.3175 0.4332 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0253 0.6400 -1.0302 C 0 0 2 0 0 0 0 0 0 0 0 0 5.6714 0.0230 -1.3234 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9653 0.3397 -0.0718 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6286 -0.2211 0.1778 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6158 0.1678 -0.8967 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3459 -0.5699 -0.5750 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0340 -0.7244 0.8643 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4730 -0.7978 1.0597 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0817 0.5710 1.0266 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4581 1.3971 2.1685 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0052 1.4893 1.9156 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7395 0.1772 1.8159 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7212 -0.4500 3.2214 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1439 0.4840 1.4527 C 0 0 1 0 0 0 0 0 0 0 0 0 4.0615 0.2831 2.5998 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 0.3344 2.2368 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2800 0.8363 3.0018 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9264 -0.2262 0.9613 C 0 0 2 0 0 0 0 0 0 0 0 0 5.8915 -1.7114 1.0518 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4451 0.6180 1.2449 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1291 1.2530 0.2432 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2768 0.4289 -0.2551 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3428 1.3588 -0.8772 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.5220 2.5431 -1.4103 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9703 3.3276 -0.2673 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8611 4.4451 0.1961 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1535 5.2994 -0.8598 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6598 2.4513 0.7784 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2698 3.3201 -2.2811 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1818 1.7500 0.1334 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5473 1.5038 -0.1343 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0763 0.5863 0.9138 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5403 0.7111 1.1913 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.9415 2.1761 1.2247 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.5078 2.7588 -0.1116 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.9509 4.2247 -0.1479 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3174 4.3644 -0.1366 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.1382 2.7678 -0.1274 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.2899 2.3449 1.4537 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8397 0.0940 2.4061 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.8787 -0.7354 0.4517 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9285 -0.5133 -1.2142 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2789 -1.7945 -0.7975 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.3674 -2.3507 -1.7193 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7539 -3.3847 -2.6539 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2582 -4.5028 -1.7486 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4954 -3.9302 -0.5825 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2001 -4.6955 -0.4099 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4874 -6.0520 -0.1655 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1543 -2.5909 -0.8216 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3815 -5.1707 -1.2692 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7032 -2.8737 -3.3920 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3669 -2.9965 -1.0120 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0415 0.0854 -1.7656 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8892 0.6858 -0.5239 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0075 0.7342 -1.3600 C 0 0 0 0 0 0 0 0 0 0 0 0 12.4427 -1.3810 -3.0775 H 0 0 0 0 0 0 0 0 0 0 0 0 12.8028 0.3561 -2.9647 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8235 -0.8173 -2.0859 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5246 -0.3682 -0.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5461 -2.5664 -1.6263 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1259 -2.1462 0.0377 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8099 -1.2829 -2.6061 H 0 0 0 0 0 0 0 0 0 0 0 0 9.0639 -2.4096 -1.3877 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8763 -1.7624 0.1358 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7485 -0.1830 2.4134 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1227 -0.2168 1.3005 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4538 -1.7786 1.9074 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6014 1.1806 1.0087 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9660 1.7424 -1.1095 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7702 -1.0522 -1.5369 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2580 0.5920 -2.1861 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9169 1.4436 0.0425 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5337 -1.2874 0.3468 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9795 -0.2053 -1.8997 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4767 1.2626 -0.9436 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4161 -1.5695 -1.0728 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4575 -0.0881 -1.0548 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3804 -1.7741 1.1432 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6022 -1.1619 2.1241 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9406 -1.5345 0.4094 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7990 1.0528 0.0624 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8602 2.4437 2.0812 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6570 0.9715 3.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1123 1.9566 0.8879 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5245 2.2052 2.5922 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6624 -0.4935 3.5500 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0907 -1.5008 3.1947 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2315 0.1900 3.9617 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2154 1.5789 1.1799 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8824 1.1431 3.3113 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9147 -0.6362 3.1892 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8902 -2.2516 0.1088 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9507 -1.9975 1.6083 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7024 -2.0112 1.7630 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3734 1.5204 -0.5416 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7293 -0.0937 0.6274 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8777 0.9026 -1.7003 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6788 2.1140 -1.9882 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0016 3.8202 -0.5707 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3986 5.0213 1.0142 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8271 4.0581 0.6093 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7766 5.9979 -0.5717 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5452 2.7780 -3.0524 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6340 1.0227 -1.1289 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5271 0.6414 1.8818 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1370 0.2382 0.3770 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2955 2.6578 1.9944 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9534 2.2024 -0.9609 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4488 4.7243 0.7077 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5239 4.6538 -1.0752 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6446 4.3945 -1.0660 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3917 3.2346 1.9099 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2917 0.7558 2.9819 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6060 -1.3279 0.7521 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7477 -1.7160 0.2087 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8057 -1.5204 -2.2778 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5468 -3.7254 -3.3350 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6211 -5.2099 -2.2993 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0728 -3.9901 0.3679 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6193 -4.5653 -1.3267 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6820 -4.3194 0.5007 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0416 -6.1485 0.6347 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0785 -5.2457 -1.9550 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0783 -2.4529 -4.2060 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2567 -2.9459 -0.0322 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5893 1.6288 -1.0665 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7293 0.8482 -2.4187 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 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 1 20 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 26 27 1 1 17 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 1 0 32 37 1 0 31 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 42 43 1 0 43 44 1 0 44 45 1 0 43 46 1 0 42 47 1 0 41 48 1 0 40 49 1 0 30 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 55 58 1 0 54 59 1 0 53 60 1 0 52 61 1 0 9 62 1 0 5 63 1 1 63 64 1 0 64 2 1 0 62 5 1 0 26 8 1 0 36 29 1 0 46 39 1 0 58 51 1 0 26 11 1 0 22 12 1 0 20 15 1 0 1 65 1 0 1 66 1 0 1 67 1 0 2 68 1 1 3 69 1 0 3 70 1 0 4 71 1 0 4 72 1 0 6 73 1 6 7 74 1 0 7 75 1 0 7 76 1 0 8 77 1 1 9 78 1 1 10 79 1 0 10 80 1 0 11 81 1 1 12 82 1 1 13 83 1 0 13 84 1 0 14 85 1 0 14 86 1 0 15 87 1 1 16 88 1 0 16 89 1 0 17 90 1 6 18 91 1 0 18 92 1 0 19 93 1 0 19 94 1 0 21 95 1 0 21 96 1 0 21 97 1 0 22 98 1 6 23 99 1 0 23100 1 0 27101 1 0 27102 1 0 27103 1 0 29104 1 6 30105 1 1 31106 1 6 32107 1 6 33108 1 6 34109 1 0 34110 1 0 35111 1 0 37112 1 0 39113 1 6 40114 1 1 41115 1 6 42116 1 1 43117 1 6 44118 1 0 44119 1 0 45120 1 0 47121 1 0 48122 1 0 49123 1 0 51124 1 1 52125 1 6 53126 1 6 54127 1 6 55128 1 1 56129 1 0 56130 1 0 57131 1 0 59132 1 0 60133 1 0 61134 1 0 64135 1 0 64136 1 0 M END

Standard InCHIKey	VGWBUQPQZOSEEG-UROMMIOCSA-N
Standard InCHI	InChI=1S/C45H72O19/c1-18-7-10-45(57-17-18)19(2)30-25(64-45)12-24-22-6-5-20-11-21(8-9-43(20,3)23(22)13-29(49)44(24,30)4)58-42-39(63-41-37(56)35(54)32(51)27(15-47)60-41)38(33(52)28(16-48)61-42)62-40-36(55)34(53)31(50)26(14-46)59-40/h18-28,30-42,46-48,50-56H,5-17H2,1-4H3/t18-,19+,20-,21+,22-,23+,24+,25+,26-,27-,28-,30+,31-,32-,33+,34+,35+,36-,37-,38+,39-,40+,41+,42-,43+,44-,45-/m1/s1
SMILES	C[C@@H]1CC[C@@]2([C@@H](C)[C@H]3[C@H](C[C@H]4[C@@H]5CC[C@@H]6C[C@H](CC[C@]6(C)[C@H]5CC(=O)[C@]34C)O[C@H]3[C@@H]([C@H]([C@H]([C@@H](CO)O3)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@@H](CO)O3)O)O)O)O2)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	916.47	Volume:	874.246 ? Van der Waals volume.
Dense:	1.048	LogP:	0.568 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.538 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.735 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	49.0
TPSA:	293.21 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	10.0	Rings:	9.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.117	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.796	Fsp³:	0.978
MCE-18:	233.719 ? 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:	0.699	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.007 ? 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:	0.259	Promiscuous compounds:	0.172

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.288	MDCK Permeability:	-5.193
Pgp-inhibitor:	0.001	Pgp-substrate:	0.248
PAMPA:	0.991 ? 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):	0.068
20% Bioavailability (F20%):	0.07	30% Bioavailability (F30%):	0.997
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.025
Plasma Protein Binding (PPB):	50.632%	Volume Distribution (VD):	-0.441
Fu:	43.19% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.106
BSEP inhibitor:	0.053

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:	0.531	CYP3A4-substrate:	0.893
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.049
HLM stability:	0.012 ? 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):

0.292

Half-life (T1/2):

2.925

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.013
Human Hepatotoxicity (H-HT):	0.716	Drug-induced Liver Injury (DILI):	0.996
AMES Toxicity:	0.987	Rat Oral Acute Toxicity:	0.004
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	1.0
Carcinogencity:	0.126	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	1.0
Hematotoxicity:	0.467	Drug-induced Nephrotoxicity:	0.919
Genotoxicity:	0.008	RPMI-8226 Immunitoxicity:	0.338
A549 Cytotoxicity:	0.981	Hek293 Cytotoxicity:	0.915
BCF:	0.997 ? 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:	3.242 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.406 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.617 ? 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
NPO19920	Yucca gloriosa	Species	Asparagaceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1016/0031-9422(89)80212-2]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[11045899]
NPO21106	Isatis costata	Species	Brassicaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17846565]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	bark	n.a.	PMID[19555186]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21718054]
NPO22631	Actinopolyspora erythraea	Species	Actinopolysporaceae	Bacteria	n.a.	mycelium	n.a.	PMID[21870828]
NPO21735	Clausena anisum-olens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368606]
NPO21635	Pandalus borealis	Species	Pandalidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3349210]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	Latex	n.a.	n.a.	PMID[6481361]
NPO20358	Streptomyces maritimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21106	Isatis costata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22631	Actinopolyspora erythraea	Species	Actinopolysporaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22938	Genista hystrix	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19380	Styela plicata	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23056	Isaria japonica	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20677	Fraxinus angustifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18197	Cadlina luteomarginata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7217	Plakobranchus ocellatus	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14364	Alisma plantago-aquatica	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20182	Euonymus pendulus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22246	Aplidium longithorax	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20042	Ambrosia cumanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25227	Senecio roseus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20952	Dioscorea cirrhosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20952	Dioscorea cirrhosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21635	Pandalus borealis	Species	Pandalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21874	Cercospora melonis	Species	Mycosphaerellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5927	Cortinarius venetus	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14364	Alisma plantago-aquatica	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22060	Hippomane mancinella	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15934	Rhododendron ponticum	Species	Ericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22453	Befaria racemosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12005	Amomum zambesiacum	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22631	Actinopolyspora erythraea	Species	Actinopolysporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14211	Acinetobacter junii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21106	Isatis costata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17898	Buckiella undulata	Species	Hypnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22697	Licaria mahuba	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22119	Echinops bannaticus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20358	Streptomyces maritimus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO22321	Euphorbia lamprocarpa	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19108	Arthrinium sacchari	Species	Apiosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18197	Cadlina luteomarginata	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23094	Pectinophora gossypiella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22938	Genista hystrix	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22993	Veronica hederifolia	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22187	Ostrea virginica	Species	Ostreidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23133	Gypsophila patrini	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23056	Isaria japonica	Species	Cordycipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19693	Lobaria oregana	Species	Lobariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21246	Helichrysum anomalum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19380	Styela plicata	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27833	Xerotus discolor	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7217	Plakobranchus ocellatus	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9972	Angostura granulosa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20032	Prunus sibirica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21997	Benzoin trilobum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10574	Machilus thunbergii	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20952	Dioscorea cirrhosa	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22246	Aplidium longithorax	Species	Polyclinidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20677	Fraxinus angustifolia	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19070	Cassia dentata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17092	Viguiera dentata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20506	Batatas edulis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO25227	Senecio roseus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22881	Cryptotermes brevis	Species	Termitoidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19920	Yucca gloriosa	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23176	Schefflera bodinieri	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22578	Speranskia tuberculata	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17819	Ferula transiliensis	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23475	Psoralea acaulis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20042	Ambrosia cumanensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21735	Clausena anisum-olens	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18568	Artemisia aucheri	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20182	Euonymus pendulus	Species	Celastraceae	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 NPC56325 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	25868
0.1-0.2	21077
0.2-0.3	2461
0.3-0.4	266
0.4-0.5	84
0.5-0.6	52
0.6-0.7	33
0.7-0.8	0
0.8-0.85	4
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9239	High Similarity	NPC475319
0.8485	Intermediate Similarity	NPC233433
0.8315	Intermediate Similarity	NPC206003
0.8315	Intermediate Similarity	NPC473610
0.81	Intermediate Similarity	NPC108072
0.7925	Intermediate Similarity	NPC220836
0.7708	Intermediate Similarity	NPC475351
0.7653	Intermediate Similarity	NPC92890
0.7642	Intermediate Similarity	NPC94086
0.7642	Intermediate Similarity	NPC473817
0.7216	Intermediate Similarity	NPC125324
0.7087	Intermediate Similarity	NPC97700
0.7087	Intermediate Similarity	NPC184617
0.7087	Intermediate Similarity	NPC30856
0.6768	Remote Similarity	NPC215408
0.6737	Remote Similarity	NPC297348
0.6737	Remote Similarity	NPC249204
0.6737	Remote Similarity	NPC48339
0.6737	Remote Similarity	NPC141769
0.6737	Remote Similarity	NPC477547
0.6731	Remote Similarity	NPC51172
0.6731	Remote Similarity	NPC49032
0.6636	Remote Similarity	NPC132080
0.6602	Remote Similarity	NPC202898
0.6571	Remote Similarity	NPC300557
0.6562	Remote Similarity	NPC325828
0.6535	Remote Similarity	NPC6295
0.6495	Remote Similarity	NPC234352
0.6442	Remote Similarity	NPC473601
0.6429	Remote Similarity	NPC477451
0.6422	Remote Similarity	NPC116756
0.6408	Remote Similarity	NPC160426
0.6381	Remote Similarity	NPC602423
0.6364	Remote Similarity	NPC232037
0.6339	Remote Similarity	NPC92297
0.6306	Remote Similarity	NPC470864
0.6303	Remote Similarity	NPC305771
0.6303	Remote Similarity	NPC94072
0.6303	Remote Similarity	NPC169816
0.6275	Remote Similarity	NPC107962
0.6238	Remote Similarity	NPC211354
0.6238	Remote Similarity	NPC107188
0.6238	Remote Similarity	NPC19400
0.6091	Remote Similarity	NPC115165
0.6055	Remote Similarity	NPC128572
0.605	Remote Similarity	NPC15918
0.6034	Remote Similarity	NPC470866
0.5966	Remote Similarity	NPC273002
0.5965	Remote Similarity	NPC83137
0.5913	Remote Similarity	NPC477811
0.5841	Remote Similarity	NPC309278
0.5833	Remote Similarity	NPC477808
0.578	Remote Similarity	NPC475643
0.5728	Remote Similarity	NPC250393
0.5652	Remote Similarity	NPC161035
0.5652	Remote Similarity	NPC170438
0.5625	Remote Similarity	NPC151134
0.562	Remote Similarity	NPC473505
0.5565	Remote Similarity	NPC475625
0.5565	Remote Similarity	NPC473518
0.5556	Remote Similarity	NPC476112
0.5556	Remote Similarity	NPC307534
0.5545	Remote Similarity	NPC485594
0.5536	Remote Similarity	NPC249553
0.5536	Remote Similarity	NPC182900
0.5534	Remote Similarity	NPC294686
0.553	Remote Similarity	NPC481189
0.5517	Remote Similarity	NPC232611
0.5463	Remote Similarity	NPC485595
0.5462	Remote Similarity	NPC31896
0.5437	Remote Similarity	NPC177834
0.5429	Remote Similarity	NPC474399
0.5424	Remote Similarity	NPC470862
0.542	Remote Similarity	NPC329807
0.5413	Remote Similarity	NPC195297
0.5398	Remote Similarity	NPC471464
0.5366	Remote Similarity	NPC477807
0.5351	Remote Similarity	NPC480555
0.5351	Remote Similarity	NPC150372
0.5349	Remote Similarity	NPC481190
0.534	Remote Similarity	NPC181845
0.5304	Remote Similarity	NPC98018
0.5304	Remote Similarity	NPC284104
0.5304	Remote Similarity	NPC103616
0.5283	Remote Similarity	NPC222731
0.5259	Remote Similarity	NPC329727
0.5225	Remote Similarity	NPC113044
0.5225	Remote Similarity	NPC283829
0.5225	Remote Similarity	NPC161676
0.5214	Remote Similarity	NPC470863
0.5196	Remote Similarity	NPC24960
0.5191	Remote Similarity	NPC330026
0.5159	Remote Similarity	NPC210569
0.5138	Remote Similarity	NPC264101
0.5124	Remote Similarity	NPC480553
0.5088	Remote Similarity	NPC470433
0.5088	Remote Similarity	NPC46190
0.5088	Remote Similarity	NPC171073
0.5043	Remote Similarity	NPC477809

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC56325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7570
0.1-0.2	1504
0.2-0.3	68
0.3-0.4	3
0.4-0.5	3
0.5-0.6	0
0.6-0.7	2
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.6562	Remote Similarity	NPD8171	Phase 2
0.6214	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