NPASS Compound

Natural Product: NPC138668

Natural Product ID	NPC138668
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	WEZNHIWHEVJNDO-DNDSGMOKSA-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:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

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 145145 0 0 0 0 0 0 0 0999 V2000 10.4530 4.6961 1.2173 C 0 0 0 0 0 0 0 0 0 0 0 0 10.3628 4.5966 -0.2972 C 0 0 0 0 0 0 0 0 0 0 0 0 11.7421 4.5630 -0.8802 C 0 0 0 0 0 0 0 0 0 0 0 0 12.5809 3.4155 -0.4202 C 0 0 0 0 0 0 0 0 0 0 0 0 11.9443 2.0771 -0.7745 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8510 0.9960 -0.2870 C 0 0 0 0 0 0 0 0 0 0 0 0 12.2938 -0.3664 -0.5931 C 0 0 0 0 0 0 0 0 0 0 0 0 10.9440 -0.5983 0.0591 C 0 0 0 0 0 0 0 0 0 0 0 0 10.4340 -1.9924 -0.2512 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2449 -2.2727 -1.6938 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2606 -1.4345 -2.4245 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8495 -1.6309 -1.7784 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9238 -0.8148 -2.5898 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5210 -0.7473 -2.1571 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7488 -1.9835 -2.0374 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0510 -2.9613 -0.9663 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8448 -2.3653 0.4229 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4116 -1.9201 0.6527 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4450 -3.0380 0.5773 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0034 -2.6565 0.7906 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5027 -1.6585 -0.2469 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.9368 -1.3572 -0.0357 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6276 -1.9089 0.8828 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.0274 -1.6870 1.1654 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4936 -2.6246 2.2676 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3173 -3.9544 1.9846 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0119 -4.4385 0.8803 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0674 -4.8575 -0.2200 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5479 -6.1425 -0.8267 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0447 -6.1310 -1.0928 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7785 -5.6999 0.1730 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.8160 -6.7084 0.5867 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7148 -6.9254 -0.4431 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8590 -5.4632 1.1929 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4067 -7.4390 -1.4022 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2495 -7.2456 -0.0556 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8215 -5.1446 0.3804 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2898 -0.2551 1.6156 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.7263 0.0694 1.7346 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.0191 1.4845 2.2100 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4310 2.4675 1.2711 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7390 3.9039 1.6552 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.2342 4.1488 1.6119 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5520 5.5812 1.9899 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0357 5.8561 1.9276 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5831 5.6632 0.5384 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0776 5.9410 0.4781 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5917 5.7616 -0.9116 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4412 4.4060 -1.4678 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.1712 3.2810 -0.8569 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9355 2.9185 0.5513 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.6806 3.4641 -1.0605 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4209 -0.1540 0.5175 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6087 -0.0497 2.7970 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5364 -0.4351 -0.8880 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6525 -2.1832 -1.5340 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6949 5.4385 1.5464 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4661 4.9377 1.5438 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1085 3.7013 1.6211 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7635 3.7202 -0.6190 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8739 5.5187 -0.7151 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6808 4.5138 -1.9886 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2650 5.4986 -0.5678 H 0 0 0 0 0 0 0 0 0 0 0 0 12.7718 3.4551 0.6671 H 0 0 0 0 0 0 0 0 0 0 0 0 13.5602 3.4802 -0.9566 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8370 2.0518 -1.8733 H 0 0 0 0 0 0 0 0 0 0 0 0 10.9248 2.0254 -0.3459 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0349 1.0456 0.8069 H 0 0 0 0 0 0 0 0 0 0 0 0 13.8251 1.0740 -0.8325 H 0 0 0 0 0 0 0 0 0 0 0 0 13.0214 -1.1335 -0.2408 H 0 0 0 0 0 0 0 0 0 0 0 0 12.2184 -0.4470 -1.7079 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1960 0.1396 -0.2445 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0870 -0.5623 1.1550 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1567 -2.7445 0.1497 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4953 -2.1444 0.3070 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2453 -2.2544 -2.2092 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9388 -3.3599 -1.7725 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4513 -0.3648 -2.3733 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2012 -1.7853 -3.4718 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6889 -2.7321 -1.9607 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9538 -1.3838 -0.7318 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3494 0.2208 -2.7958 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9230 -1.2609 -3.6527 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4473 -0.1499 -1.1847 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9674 -0.0517 -2.8921 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6320 -1.8046 -2.0522 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8930 -2.5632 -3.0170 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2944 -3.7971 -1.0829 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0035 -3.4473 -0.9743 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0547 -3.1757 1.1514 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4842 -1.5028 0.6035 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3744 -1.4694 1.6534 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1174 -1.1273 -0.0738 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6663 -3.8349 1.3498 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5438 -3.5838 -0.3936 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8559 -2.2750 1.8140 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4051 -3.5797 0.6266 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1387 -0.7730 -0.1817 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6128 -1.8685 0.2556 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8356 -2.3970 3.1456 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5141 -2.3666 2.5711 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6286 -3.5755 0.4947 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9496 -4.0544 -0.9785 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0651 -6.2775 -1.8266 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2897 -5.4877 -1.9559 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2839 -4.7480 -0.0538 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3872 -7.6435 0.9681 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3663 -6.2385 1.4481 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6538 -7.0721 -0.0950 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8707 -7.5328 -2.2475 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0616 -7.5438 0.4046 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.1410 -5.2986 -0.3308 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8232 0.4503 0.8477 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2624 -0.5802 2.4657 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1118 1.6187 2.3651 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5854 1.5994 3.2434 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7962 2.2632 0.2472 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3103 2.3336 1.2956 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3351 4.1480 2.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2396 4.5516 0.8904 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7320 3.4776 2.3444 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6124 3.8795 0.6193 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0357 6.2725 1.3093 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1898 5.7579 3.0203 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6231 5.2168 2.6263 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2217 6.9063 2.2291 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0768 6.3977 -0.1635 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3895 4.6663 0.1404 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6354 5.3435 1.1859 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2091 7.0365 0.7191 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1207 6.5463 -1.5653 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.6918 6.0471 -0.8835 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3573 4.1157 -1.5462 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7949 4.4650 -2.5496 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9282 2.3726 -1.4881 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9264 3.1014 0.9311 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.7208 3.2982 1.2546 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1095 1.7835 0.6185 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.8440 4.2281 -1.8289 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1335 2.4910 -1.3231 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1580 3.7609 -0.0927 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3813 0.0902 0.6789 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8973 0.6387 2.7211 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4792 -0.5650 -1.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5102 -3.1674 -1.5382 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 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 0 21 22 1 0 22 23 2 3 23 24 1 0 24 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 31 32 1 0 32 33 1 0 31 34 1 0 30 35 1 0 29 36 1 0 28 37 1 0 24 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 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 39 53 1 0 38 54 1 0 22 55 1 0 21 56 1 0 34 27 1 0 1 57 1 0 1 58 1 0 1 59 1 0 2 60 1 0 2 61 1 0 3 62 1 0 3 63 1 0 4 64 1 0 4 65 1 0 5 66 1 0 5 67 1 0 6 68 1 0 6 69 1 0 7 70 1 0 7 71 1 0 8 72 1 0 8 73 1 0 9 74 1 0 9 75 1 0 10 76 1 0 10 77 1 0 11 78 1 0 11 79 1 0 12 80 1 0 12 81 1 0 13 82 1 0 13 83 1 0 14 84 1 0 14 85 1 0 15 86 1 0 15 87 1 0 16 88 1 0 16 89 1 0 17 90 1 0 17 91 1 0 18 92 1 0 18 93 1 0 19 94 1 0 19 95 1 0 20 96 1 0 20 97 1 0 21 98 1 6 24 99 1 6 25100 1 0 25101 1 0 27102 1 6 28103 1 6 29104 1 6 30105 1 6 31106 1 6 32107 1 0 32108 1 0 33109 1 0 35110 1 0 36111 1 0 37112 1 0 38113 1 6 39114 1 1 40115 1 0 40116 1 0 41117 1 0 41118 1 0 42119 1 0 42120 1 0 43121 1 0 43122 1 0 44123 1 0 44124 1 0 45125 1 0 45126 1 0 46127 1 0 46128 1 0 47129 1 0 47130 1 0 48131 1 0 48132 1 0 49133 1 0 49134 1 0 50135 1 0 51136 1 0 51137 1 0 51138 1 0 52139 1 0 52140 1 0 52141 1 0 53142 1 0 54143 1 0 55144 1 0 56145 1 0 M END

Standard InCHIKey	WEZNHIWHEVJNDO-DNDSGMOKSA-N
Standard InCHI	InChI=1S/C45H89NO10/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23-26-29-32-38(49)44(54)46-36(34-55-45-43(53)42(52)41(51)39(33-47)56-45)40(50)37(48)31-28-25-22-20-19-21-24-27-30-35(2)3/h35-43,45,47-53H,4-34H2,1-3H3,(H,46,54)/t36-,37+,38+,39+,40-,41-,42-,43-,45+/m0/s1
SMILES	CCCCCCCCCCCCCCCCCCCC[C@H](C(=N[C@@H](CO[C@H]1[C@H]([C@H]([C@H]([C@@H](CO)O1)O)O)O)[C@@H]([C@@H](CCCCCCCCCCC(C)C)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	803.65	Volume:	874.582 ? Van der Waals volume.
Dense:	0.919	LogP:	8.922 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	5.159 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.415 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	38.0	Rigid Bonds:	7.0
TPSA:	192.66 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	8.0	Rings:	1.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.017	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.997	Fsp³:	0.978
MCE-18:	29.573 ? 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:	0.741	Fluc inhibitor:	0.035 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.006 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.006 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.03	Promiscuous compounds:	0.036

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.497	MDCK Permeability:	-4.934
Pgp-inhibitor:	0.0	Pgp-substrate:	0.742
PAMPA:	0.066 ? 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):	1.0
20% Bioavailability (F20%):	1.0	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.983
Plasma Protein Binding (PPB):	100.172%	Volume Distribution (VD):	1.449
Fu:	0.805% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.246
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.12
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.962	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.988
HLM stability:	0.043 ? 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):

2.564

Half-life (T1/2):

3.951

ADMET: Toxicity

hERG Blockers:	0.224	hERG Blockers (10um):	0.412
Human Hepatotoxicity (H-HT):	0.84	Drug-induced Liver Injury (DILI):	0.107
AMES Toxicity:	0.139	Rat Oral Acute Toxicity:	0.012
Maximum Recommended Daily Dose:	0.031	Skin Sensitization:	1.0
Carcinogencity:	0.086	Eye Corrosion:	0.008
Eye Irritation:	0.949	Respiratory Toxicity:	0.968
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.852
Hematotoxicity:	0.501	Drug-induced Nephrotoxicity:	0.507
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.102
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	0.441
BCF:	0.786 ? 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:	5.29 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.704 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.356 ? 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
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15043423]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29182349]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4490	Cephalotaxus sinensis	Species	Taxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10409	Methanothermobacter thermautotrophicus	Species	Methanobacteriaceae	Archaea	n.a.	n.a.	n.a.	Database[UNPD]
NPO10828	Adina racemosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21552	Oreaster nodosus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7956	Discaria chacaye	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5447	Digitalis canariensis	Species	Plantaginaceae	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 NPC138668 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	15928
0.1-0.2	28693
0.2-0.3	4708
0.3-0.4	448
0.4-0.5	34
0.5-0.6	18
0.6-0.7	27
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC61894
0.8333	Intermediate Similarity	NPC297079
0.6716	Remote Similarity	NPC263545
0.6716	Remote Similarity	NPC473950
0.6716	Remote Similarity	NPC111567
0.6716	Remote Similarity	NPC186840
0.6716	Remote Similarity	NPC144916
0.6716	Remote Similarity	NPC486421
0.6716	Remote Similarity	NPC309898
0.6716	Remote Similarity	NPC273493
0.6716	Remote Similarity	NPC475125
0.6716	Remote Similarity	NPC486419
0.6716	Remote Similarity	NPC15851
0.6716	Remote Similarity	NPC115448
0.6716	Remote Similarity	NPC20819
0.6716	Remote Similarity	NPC486418
0.6716	Remote Similarity	NPC473604
0.6716	Remote Similarity	NPC486420
0.6716	Remote Similarity	NPC479188
0.6716	Remote Similarity	NPC81468
0.6522	Remote Similarity	NPC156782
0.6522	Remote Similarity	NPC54961
0.6429	Remote Similarity	NPC158445
0.6429	Remote Similarity	NPC157353
0.6429	Remote Similarity	NPC282088
0.625	Remote Similarity	NPC3568
0.625	Remote Similarity	NPC17290
0.625	Remote Similarity	NPC192066
0.625	Remote Similarity	NPC256570
0.5932	Remote Similarity	NPC195165
0.5921	Remote Similarity	NPC8098
0.5921	Remote Similarity	NPC183449
0.5921	Remote Similarity	NPC197294
0.5775	Remote Similarity	NPC282705
0.5775	Remote Similarity	NPC182632
0.5775	Remote Similarity	NPC476523
0.5714	Remote Similarity	NPC43074
0.5714	Remote Similarity	NPC139782
0.5714	Remote Similarity	NPC74672
0.5714	Remote Similarity	NPC209047
0.5556	Remote Similarity	NPC242503
0.5256	Remote Similarity	NPC23454
0.5256	Remote Similarity	NPC70323
0.5256	Remote Similarity	NPC262312
0.5256	Remote Similarity	NPC35269
0.519	Remote Similarity	NPC45313
0.5085	Remote Similarity	NPC145627

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC138668 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5159
0.1-0.2	3784
0.2-0.3	191
0.3-0.4	15
0.4-0.5	0
0.5-0.6	1
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
0.5714	Remote Similarity	NPD8522	Clinical (unspecified phase)

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