NPASS Compound

Natural Product: NPC564438

Natural Product ID	NPC564438
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	3-[(3~{S},5~{R},8~{R},9~{S},10~{S},13~{R},14~{S},17~{R})-3-[(2~{R},4~{R},5~{R},6~{R})-5-[(2~{R},4~{S},5~{R},6~{S})-5-[(2~{R},4~{S},5~{S},6~{S})-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2~{H}-furan-5-one
IUPAC Name	3-[(3~{S},5~{R},8~{R},9~{S},10~{S},13~{R},14~{S},17~{R})-3-[(2~{R},4~{R},5~{R},6~{R})-5-[(2~{R},4~{S},5~{R},6~{S})-5-[(2~{R},4~{S},5~{S},6~{S})-4,5-dihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-4-hydroxy-6-methyl-tetrahydropyran-2-yl]oxy-14-hydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2~{H}-furan-5-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 118125 0 0 0 0 0 0 0 0999 V2000 13.2205 -0.4663 -0.0324 C 0 0 0 0 0 0 0 0 0 0 0 0 12.1899 0.3774 0.6764 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9176 0.1452 0.1512 O 0 0 0 0 0 0 0 0 0 0 0 0 9.9604 0.9518 0.7368 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7118 0.4640 0.2827 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8959 0.0470 1.3043 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6242 0.8917 1.4315 C 0 0 2 0 0 0 0 0 0 0 0 0 6.7204 1.8685 2.5863 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5959 0.0046 1.7538 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1967 -0.6657 0.5916 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0200 -1.3434 0.8046 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9658 -0.9078 -0.0321 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9337 -0.3197 0.8758 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4574 -0.0234 2.1093 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8227 -1.3396 0.9885 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2331 -1.4409 -0.4030 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8800 -2.2801 -0.3565 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0691 -1.6890 -0.7239 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7003 -2.2587 -1.9501 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9069 -1.3353 -2.2185 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9908 -1.5937 -1.2038 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.9041 -2.6243 -1.8391 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4337 -2.2283 0.0551 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.2609 -1.9836 1.2649 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7000 -1.6756 1.0515 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0137 -0.8335 -0.1336 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7210 -0.3618 -0.7375 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.9139 0.6603 -1.8218 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7798 1.7607 -1.2593 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1615 1.3035 -0.8488 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9595 0.9009 -2.0684 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.7738 2.4548 -0.0970 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.1883 2.7481 -0.4701 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.5565 3.8702 -1.0390 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.9852 3.8637 -1.2747 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7105 4.7646 -1.8050 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.4483 2.6579 -0.8043 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.3820 1.9029 -0.2960 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6259 2.2003 1.3717 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8185 0.9144 1.5075 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0128 0.2391 0.1718 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.2598 -0.4277 0.2837 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0388 -1.7266 0.3797 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1530 -2.0558 -1.2058 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -1.9686 -0.9430 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9046 -3.3190 -0.3539 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3446 -1.5566 0.1785 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5137 -1.4154 1.1655 C 0 0 2 0 0 0 0 0 0 0 0 0 7.1780 -1.9431 2.4140 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0990 2.3519 0.2125 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5064 2.6245 -0.1692 C 0 0 2 0 0 0 0 0 0 0 0 0 11.7300 2.4406 -1.5503 O 0 0 0 0 0 0 0 0 0 0 0 0 12.5294 1.8508 0.6365 C 0 0 2 0 0 0 0 0 0 0 0 0 13.7511 1.9781 -0.0222 O 0 0 0 0 0 0 0 0 0 0 0 0 13.3208 -1.4296 0.5162 H 0 0 0 0 0 0 0 0 0 0 0 0 14.2067 0.0620 0.1059 H 0 0 0 0 0 0 0 0 0 0 0 0 12.9814 -0.6382 -1.0980 H 0 0 0 0 0 0 0 0 0 0 0 0 12.1681 0.0667 1.7364 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0089 0.9056 1.8472 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4189 0.1785 2.2671 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4440 1.3683 0.4618 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9820 2.8559 2.1549 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4663 1.4927 3.3124 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7368 1.9983 3.0986 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0364 0.0695 -0.2441 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3646 -0.0781 -0.6726 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4882 0.6023 0.4131 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8263 0.8816 2.1734 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0670 -1.0643 1.7473 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2675 -2.3023 1.2786 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0476 -0.4221 -0.7776 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8029 -0.6140 -0.9533 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1102 -3.2597 -1.7803 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0701 -2.1897 -2.8586 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1909 -1.5571 -3.2643 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 -0.3238 -2.2042 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4449 -3.2316 -1.1018 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2413 -3.3437 -2.3882 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5540 -2.1815 -2.6207 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3288 -3.3115 -0.1590 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8101 -1.2159 1.9447 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2235 -2.9328 1.8808 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.0581 -1.1443 1.9606 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3031 -2.6346 1.0657 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5312 -1.5177 -0.8775 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1498 0.1325 0.0772 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2917 0.2609 -2.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9048 1.1601 -1.9440 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2776 2.1772 -0.3550 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8956 2.5475 -2.0246 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4302 -0.0686 -1.9226 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6306 1.7415 -2.3147 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2423 0.8012 -2.9110 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1639 3.3942 -0.2929 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9332 4.7234 -1.3205 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5195 1.7065 0.8118 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2995 0.9226 -0.8309 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0527 2.9782 1.8983 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6111 2.1468 1.8742 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3585 0.3411 2.3193 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7642 1.0865 1.7689 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2444 -1.3065 -0.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6089 -2.3661 1.2110 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0907 -0.7104 0.8555 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0618 -1.9121 -1.9210 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0436 -4.0022 -0.2056 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6734 -3.8119 -0.9904 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3867 -3.1867 0.6356 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0754 -2.6313 0.1490 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7391 -1.3067 -0.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3832 -1.9598 0.7893 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4762 -1.2901 3.0990 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7816 3.1161 0.9583 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4404 2.4850 -0.6754 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7251 3.7047 0.0048 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4903 3.2666 -2.0656 H 0 0 0 0 0 0 0 0 0 0 0 0 12.6589 2.2498 1.6591 H 0 0 0 0 0 0 0 0 0 0 0 0 14.5234 2.0670 0.5803 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 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 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 6 21 23 1 0 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 6 30 32 1 0 32 33 1 0 33 34 2 0 34 35 1 0 35 36 2 0 35 37 1 0 37 38 1 0 32 39 1 0 39 40 1 0 40 41 1 0 41 42 1 1 23 43 1 0 16 44 1 0 44 45 1 0 45 46 1 0 10 47 1 0 47 48 1 0 48 49 1 0 4 50 1 0 50 51 1 0 51 52 1 0 51 53 1 0 53 54 1 0 53 2 1 0 48 6 1 0 45 12 1 0 43 18 1 0 27 21 1 0 41 30 1 0 41 26 1 0 38 33 1 0 1 55 1 0 1 56 1 0 1 57 1 0 2 58 1 1 4 59 1 1 6 60 1 1 7 61 1 6 8 62 1 0 8 63 1 0 8 64 1 0 10 65 1 6 12 66 1 6 13 67 1 6 14 68 1 0 15 69 1 0 15 70 1 0 16 71 1 6 18 72 1 6 19 73 1 0 19 74 1 0 20 75 1 0 20 76 1 0 22 77 1 0 22 78 1 0 22 79 1 0 23 80 1 6 24 81 1 0 24 82 1 0 25 83 1 0 25 84 1 0 26 85 1 6 27 86 1 1 28 87 1 0 28 88 1 0 29 89 1 0 29 90 1 0 31 91 1 0 31 92 1 0 31 93 1 0 32 94 1 6 34 95 1 0 38 96 1 0 38 97 1 0 39 98 1 0 39 99 1 0 40100 1 0 40101 1 0 42102 1 0 43103 1 0 43104 1 0 45105 1 6 46106 1 0 46107 1 0 46108 1 0 47109 1 0 47110 1 0 48111 1 6 49112 1 0 50113 1 0 50114 1 0 51115 1 6 52116 1 0 53117 1 1 54118 1 0 M END

Standard InCHIKey	WDJUZGPOPHTGOT-VEBSLOLJSA-N
Standard InCHI	InChI=1S/C41H64O13/c1-20-36(46)29(42)16-34(49-20)53-38-22(3)51-35(18-31(38)44)54-37-21(2)50-33(17-30(37)43)52-25-8-11-39(4)24(15-25)6-7-28-27(39)9-12-40(5)26(10-13-41(28,40)47)23-14-32(45)48-19-23/h14,20-22,24-31,33-38,42-44,46-47H,6-13,15-19H2,1-5H3/t20-,21+,22-,24+,25-,26+,27-,28+,29-,30+,31-,33-,34+,35+,36+,37-,38-,39-,40+,41-/m0/s1
SMILES	C[C@@H]1O[C@H](O[C@H]2[C@H](C)O[C@H](O[C@@H]3[C@H](O)C[C@H](O[C@H]4CC[C@@]5(C)[C@H](CC[C@@H]6[C@@H]5CC[C@]5(C)[C@@H](C7=CC(=O)OC7)CC[C@]65O)C4)O[C@@H]3C)C[C@@H]2O)C[C@H](O)[C@@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	764.43	Volume:	758.24 ? Van der Waals volume.
Dense:	1.008	LogP:	2.484 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.952 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.791 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	44.0
TPSA:	182.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	13.0
H-Bond Donor:	5.0	Rings:	8.0
Heavy Atoms:	13.0

MedChem Properties

QED Drug-Likeness Score:	0.188	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.984	Fsp³:	0.927
MCE-18:	147.443 ? 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:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.882	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.016 ? 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:	0.249	Promiscuous compounds:	0.615

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.776	MDCK Permeability:	-5.332
Pgp-inhibitor:	0.05	Pgp-substrate:	0.849
PAMPA:	0.996 ? 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):	0.039
20% Bioavailability (F20%):	0.678	30% Bioavailability (F30%):	0.526
50% Bioavailability (F50%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.057	MRP1:	0.928
Plasma Protein Binding (PPB):	63.052%	Volume Distribution (VD):	-0.554
Fu:	34.022% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.995
OATP1B3 inhibitor:	0.889	BCRP inhibitor:	0.125
BSEP inhibitor:	0.542

ADMET: Metabolism

CYP1A2-inhibitor:	0.069	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.862	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.998	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.198
HLM stability:	0.382 ? 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):

0.817

Half-life (T1/2):

3.219

ADMET: Toxicity

hERG Blockers:	0.114	hERG Blockers (10um):	0.662
Human Hepatotoxicity (H-HT):	0.661	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.999	Rat Oral Acute Toxicity:	0.999
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	1.0
Carcinogencity:	0.956	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	1.0
Drug-induced Neurotoxicity:	0.115	Ototoxicity:	0.95
Hematotoxicity:	0.99	Drug-induced Nephrotoxicity:	0.998
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.968
A549 Cytotoxicity:	1.0	Hek293 Cytotoxicity:	1.0
BCF:	0.695 ? 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:	3.31 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.812 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.031 ? 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
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s00253-012-4489-y]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1093/oxfordjournals.pcp.a076462]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834166]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4443	Digitalis purpurea	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 NPC564438 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	14364
0.1-0.2	30662
0.2-0.3	4491
0.3-0.4	113
0.4-0.5	81
0.5-0.6	85
0.6-0.7	41
0.7-0.8	4
0.8-0.85	2
0.85-0.9	0
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC72260
0.9054	High Similarity	NPC471633
0.8395	Intermediate Similarity	NPC173555
0.8375	Intermediate Similarity	NPC193893
0.7907	Intermediate Similarity	NPC55532
0.7625	Intermediate Similarity	NPC99620
0.7609	Intermediate Similarity	NPC120390
0.7609	Intermediate Similarity	NPC74259
0.7582	Intermediate Similarity	NPC475590
0.7195	Intermediate Similarity	NPC473852
0.7143	Intermediate Similarity	NPC84949
0.7143	Intermediate Similarity	NPC480562
0.7143	Intermediate Similarity	NPC74945
0.7143	Intermediate Similarity	NPC31354
0.7143	Intermediate Similarity	NPC69576
0.7111	Intermediate Similarity	NPC125077
0.7024	Intermediate Similarity	NPC5311
0.6966	Remote Similarity	NPC236973
0.6923	Remote Similarity	NPC208193
0.6867	Remote Similarity	NPC474418
0.6782	Remote Similarity	NPC93883
0.6744	Remote Similarity	NPC199428
0.6744	Remote Similarity	NPC109448
0.6744	Remote Similarity	NPC310341
0.6739	Remote Similarity	NPC486143
0.6739	Remote Similarity	NPC486142
0.6739	Remote Similarity	NPC486149
0.6632	Remote Similarity	NPC475219
0.6628	Remote Similarity	NPC469750
0.6591	Remote Similarity	NPC484202
0.6552	Remote Similarity	NPC76572
0.6552	Remote Similarity	NPC193382
0.6484	Remote Similarity	NPC30483
0.6484	Remote Similarity	NPC470897
0.6465	Remote Similarity	NPC117445
0.6465	Remote Similarity	NPC474908
0.6465	Remote Similarity	NPC308262
0.6436	Remote Similarity	NPC474423
0.6421	Remote Similarity	NPC486146
0.6413	Remote Similarity	NPC292467
0.6364	Remote Similarity	NPC475419
0.6344	Remote Similarity	NPC475556
0.6344	Remote Similarity	NPC311706
0.6327	Remote Similarity	NPC486144
0.6327	Remote Similarity	NPC486145
0.6327	Remote Similarity	NPC486147
0.6327	Remote Similarity	NPC486148
0.6136	Remote Similarity	NPC196429
0.6067	Remote Similarity	NPC77299
0.6067	Remote Similarity	NPC480906
0.6064	Remote Similarity	NPC32177
0.6064	Remote Similarity	NPC469756
0.6064	Remote Similarity	NPC275901
0.6044	Remote Similarity	NPC483822
0.6	Remote Similarity	NPC188234
0.6	Remote Similarity	NPC240070
0.6	Remote Similarity	NPC480914
0.6	Remote Similarity	NPC608063
0.598	Remote Similarity	NPC486134
0.598	Remote Similarity	NPC486141
0.5955	Remote Similarity	NPC484211
0.5918	Remote Similarity	NPC329986
0.5918	Remote Similarity	NPC140092
0.5889	Remote Similarity	NPC99080
0.5889	Remote Similarity	NPC480915
0.5876	Remote Similarity	NPC486135
0.5876	Remote Similarity	NPC486137
0.5843	Remote Similarity	NPC99728
0.5843	Remote Similarity	NPC87250
0.5843	Remote Similarity	NPC244402
0.5843	Remote Similarity	NPC50305
0.5842	Remote Similarity	NPC329636
0.5816	Remote Similarity	NPC232785
0.5816	Remote Similarity	NPC486139
0.5761	Remote Similarity	NPC250556
0.5745	Remote Similarity	NPC480907
0.5714	Remote Similarity	NPC157376
0.5714	Remote Similarity	NPC17896
0.5714	Remote Similarity	NPC469755
0.5714	Remote Similarity	NPC284406
0.5714	Remote Similarity	NPC197707
0.5714	Remote Similarity	NPC251866
0.5714	Remote Similarity	NPC142066
0.5714	Remote Similarity	NPC603972
0.5699	Remote Similarity	NPC179412
0.5699	Remote Similarity	NPC471356
0.5699	Remote Similarity	NPC471353
0.5699	Remote Similarity	NPC305574
0.5684	Remote Similarity	NPC103534
0.5684	Remote Similarity	NPC44899
0.5684	Remote Similarity	NPC304260
0.5684	Remote Similarity	NPC29639
0.5679	Remote Similarity	NPC268829
0.5679	Remote Similarity	NPC295110
0.5673	Remote Similarity	NPC329675
0.5612	Remote Similarity	NPC231518
0.5612	Remote Similarity	NPC488944
0.5545	Remote Similarity	NPC486138
0.5545	Remote Similarity	NPC276838
0.5543	Remote Similarity	NPC479356
0.5543	Remote Similarity	NPC479355
0.5534	Remote Similarity	NPC486136
0.551	Remote Similarity	NPC480910
0.551	Remote Similarity	NPC480909
0.5437	Remote Similarity	NPC488943
0.5437	Remote Similarity	NPC488942
0.5413	Remote Similarity	NPC286809
0.5376	Remote Similarity	NPC34390
0.5376	Remote Similarity	NPC484210
0.5361	Remote Similarity	NPC488935
0.5361	Remote Similarity	NPC5883
0.5361	Remote Similarity	NPC488936
0.5288	Remote Similarity	NPC479360
0.5288	Remote Similarity	NPC479359
0.5269	Remote Similarity	NPC84987
0.5263	Remote Similarity	NPC180079
0.5253	Remote Similarity	NPC40749
0.5213	Remote Similarity	NPC477580
0.52	Remote Similarity	NPC32793
0.52	Remote Similarity	NPC116075
0.5185	Remote Similarity	NPC486150
0.5158	Remote Similarity	NPC152615
0.5158	Remote Similarity	NPC10823
0.5149	Remote Similarity	NPC475629
0.5146	Remote Similarity	NPC146857
0.5143	Remote Similarity	NPC488938
0.5143	Remote Similarity	NPC488937
0.5138	Remote Similarity	NPC488945
0.5138	Remote Similarity	NPC488946
0.5106	Remote Similarity	NPC309034
0.5104	Remote Similarity	NPC77319
0.5104	Remote Similarity	NPC471351
0.5104	Remote Similarity	NPC471355
0.51	Remote Similarity	NPC27363
0.5059	Remote Similarity	NPC196931
0.5059	Remote Similarity	NPC480913
0.5054	Remote Similarity	NPC158344
0.5053	Remote Similarity	NPC6108
0.5053	Remote Similarity	NPC89514
0.5052	Remote Similarity	NPC277374
0.505	Remote Similarity	NPC479353
0.505	Remote Similarity	NPC479354
0.505	Remote Similarity	NPC486130

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC564438 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6042
0.1-0.2	2979
0.2-0.3	113
0.3-0.4	2
0.4-0.5	4
0.5-0.6	3
0.6-0.7	0
0.7-0.8	4
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD8294	Phase 4
0.8395	Intermediate Similarity	NPD8296	Phase 4
0.8333	Intermediate Similarity	NPD8377	Phase 4
0.7381	Intermediate Similarity	NPD8380	Approved
0.7262	Intermediate Similarity	NPD8335	Phase 4
0.7033	Intermediate Similarity	NPD8378	Pre-clinical
0.7033	Intermediate Similarity	NPD8379	Approved
0.5761	Remote Similarity	NPD7507	Pre-clinical
0.5714	Remote Similarity	NPD7319	Approved
0.5612	Remote Similarity	NPD8033	Approved

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