NPASS Compound

Natural Product: NPC146414

Natural Product ID	NPC146414
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YFGQJKBUXPKSAW-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	407582
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001125] Steroid lactones [CHEMONTID:0001555] Cardenolides and derivatives [CHEMONTID:0001559] Cardenolide glycosides and derivatives

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 144152 0 0 0 0 0 0 0 0999 V2000 0.2948 -1.2645 2.0150 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4482 0.1498 1.5211 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3640 0.4382 0.2733 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6074 0.8254 -0.7976 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6489 -0.2892 -0.8668 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4661 -0.1910 0.4153 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7670 0.5219 1.3638 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6798 0.4381 0.1531 O 0 0 0 0 0 0 0 0 0 0 0 0 4.7886 -0.3189 0.5247 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6477 0.3853 1.5405 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0133 0.7232 0.9407 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6682 -0.6177 0.6550 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4704 -1.4387 1.9451 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9351 -1.2859 -0.4400 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6103 -1.5835 -1.7341 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1082 -1.6902 -1.6115 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5248 -0.3909 -0.9735 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1220 -0.5215 0.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7913 0.5652 1.2589 C 0 0 0 0 0 0 0 0 0 0 0 0 11.3077 0.3645 1.2662 C 0 0 0 0 0 0 0 0 0 0 0 0 11.8526 -0.2770 0.0402 C 0 0 0 0 0 0 0 0 0 0 0 0 12.0658 -1.7668 0.1998 C 0 0 0 0 0 0 0 0 0 0 0 0 13.1498 0.2808 -0.4847 C 0 0 0 0 0 0 0 0 0 0 0 0 12.8895 0.6668 -1.9481 C 0 0 0 0 0 0 0 0 0 0 0 0 11.6845 -0.2376 -2.3105 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8865 0.0595 -1.0737 C 0 0 0 0 0 0 0 0 0 0 0 0 10.8745 1.4904 -1.0401 O 0 0 0 0 0 0 0 0 0 0 0 0 13.7466 1.3789 0.2715 C 0 0 0 0 0 0 0 0 0 0 0 0 14.0005 2.6310 -0.1540 C 0 0 0 0 0 0 0 0 0 0 0 0 14.5981 3.4144 0.9125 C 0 0 0 0 0 0 0 0 0 0 0 0 14.9688 4.6277 0.8742 O 0 0 0 0 0 0 0 0 0 0 0 0 14.7079 2.6162 2.0144 O 0 0 0 0 0 0 0 0 0 0 0 0 14.2873 1.3188 1.6458 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5519 -0.6884 -0.7105 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0624 1.1209 -2.0186 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1133 -0.6798 -0.0170 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4907 -0.4640 0.0302 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0128 -0.6048 -1.3804 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4719 -0.2102 -1.3374 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0480 -0.5302 0.0259 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3650 -1.7036 0.6339 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3461 -2.9244 -0.2217 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0409 -1.3525 0.9086 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3957 -0.5901 -0.1167 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1565 0.3299 0.5060 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9301 1.1076 -0.5681 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.2754 1.5086 0.0254 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0929 0.2125 0.1395 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1084 -0.8741 0.4917 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7664 -2.0557 1.1903 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1186 -0.3043 1.2896 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.7859 -0.0387 -1.0200 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.1330 -0.0997 -0.7615 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.7930 -1.3945 -1.1583 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.1608 -1.4013 -0.4713 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.9242 -0.1401 -0.7932 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.0299 1.0905 -0.6885 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7965 2.2923 -1.1745 C 0 0 0 0 0 0 0 0 0 0 0 0 -15.1230 2.1057 -2.5365 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.8444 0.9148 -1.4228 O 0 0 0 0 0 0 0 0 0 0 0 0 -15.9314 0.0134 0.1618 O 0 0 0 0 0 0 0 0 0 0 0 0 -13.9204 -1.4886 0.9014 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9474 -1.3647 -2.5489 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0142 1.9310 1.3503 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3681 3.2008 1.7378 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9166 3.9550 0.8993 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1301 3.7280 3.1132 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2121 -0.7857 -2.3605 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2635 -1.5038 2.5421 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1548 -1.9814 1.2057 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4932 -1.3608 2.7973 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0547 0.7977 2.3597 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0190 1.3297 0.4792 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1283 1.7495 -0.4390 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1190 -1.2445 -0.8561 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2576 -0.0870 -1.7647 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6902 -1.1809 0.8601 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4109 -1.2454 0.9849 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1683 1.3944 1.7150 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7267 -0.0915 2.5126 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8185 1.3121 0.0419 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5599 1.2975 1.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2083 -2.2770 1.9611 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6003 -0.7669 2.8082 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4853 -1.8773 1.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6601 -2.3236 -0.0235 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2753 -2.6121 -2.0717 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3205 -0.8641 -2.5455 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5934 -1.8690 -2.5730 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2620 -2.5718 -0.9188 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8409 0.3990 -1.4109 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5696 -1.4996 0.8129 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4948 1.5719 0.9366 H 0 0 0 0 0 0 0 0 0 0 0 0 9.4710 0.4702 2.3359 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6152 -0.2145 2.1578 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7057 1.3978 1.3107 H 0 0 0 0 0 0 0 0 0 0 0 0 13.1687 -2.0158 0.1268 H 0 0 0 0 0 0 0 0 0 0 0 0 11.8216 -2.1350 1.2311 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6112 -2.3752 -0.6048 H 0 0 0 0 0 0 0 0 0 0 0 0 13.9585 -0.5093 -0.5695 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7239 0.4478 -2.6081 H 0 0 0 0 0 0 0 0 0 0 0 0 12.5294 1.6838 -2.0704 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2037 0.1186 -3.2433 H 0 0 0 0 0 0 0 0 0 0 0 0 11.9758 -1.2735 -2.4416 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4664 1.7878 -1.8947 H 0 0 0 0 0 0 0 0 0 0 0 0 13.7833 2.9742 -1.1460 H 0 0 0 0 0 0 0 0 0 0 0 0 15.2093 0.6406 1.5698 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6740 0.8329 2.3979 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7262 0.2271 -1.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9884 -1.3934 -1.3489 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1782 2.0703 -2.1335 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6066 0.6151 0.3129 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8238 -1.5783 -1.8277 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4854 0.1477 -2.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5509 0.8908 -1.4759 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8122 0.3473 0.6838 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8308 -1.8871 1.6409 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9742 -3.7293 0.2636 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8029 -2.7835 -1.2177 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3432 -3.3845 -0.3428 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6586 1.0798 1.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0137 0.5514 -1.5013 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3717 2.0318 -0.7874 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.7556 2.2607 -0.5976 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8088 0.2934 0.9886 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6191 -1.3077 -0.4118 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4283 -1.7606 2.0039 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.2129 -2.7260 0.4342 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9054 -2.6503 1.6196 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.3245 0.0611 0.3271 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.1947 -2.2376 -0.8173 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.7112 -2.2776 -0.8682 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.3372 -0.1918 -1.8151 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.7147 1.2700 0.3572 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.1361 3.1982 -1.0684 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.7094 2.3835 -0.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 -14.9419 2.9709 -2.9917 H 0 0 0 0 0 0 0 0 0 0 0 0 -15.4683 0.1650 1.0335 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.1905 -2.1409 1.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0021 -2.3180 -2.8425 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4420 4.6110 3.0881 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1157 3.9889 3.5488 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6950 2.9213 3.7343 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7159 -0.8823 -3.1915 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 12 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 21 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 23 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 30 32 1 0 32 33 1 0 14 34 1 0 4 35 1 0 3 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 40 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 49 51 1 0 48 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 55 56 1 0 56 57 1 0 57 58 1 0 58 59 1 0 57 60 1 0 56 61 1 0 55 62 1 0 54 63 1 0 47 64 1 0 64 65 1 0 65 66 2 0 65 67 1 0 39 68 1 0 7 2 1 0 34 9 1 0 43 37 1 0 51 45 1 0 60 53 1 0 18 12 1 0 26 21 1 0 33 28 1 0 26 17 1 0 1 69 1 0 1 70 1 0 1 71 1 0 2 72 1 0 3 73 1 0 4 74 1 0 5 75 1 0 5 76 1 0 6 77 1 0 9 78 1 0 10 79 1 0 10 80 1 0 11 81 1 0 11 82 1 0 13 83 1 0 13 84 1 0 13 85 1 0 14 86 1 0 15 87 1 0 15 88 1 0 16 89 1 0 16 90 1 0 17 91 1 0 18 92 1 0 19 93 1 0 19 94 1 0 20 95 1 0 20 96 1 0 22 97 1 0 22 98 1 0 22 99 1 0 23100 1 0 24101 1 0 24102 1 0 25103 1 0 25104 1 0 27105 1 0 29106 1 0 33107 1 0 33108 1 0 34109 1 0 34110 1 0 35111 1 0 37112 1 0 38113 1 0 38114 1 0 39115 1 0 40116 1 0 41117 1 0 42118 1 0 42119 1 0 42120 1 0 45121 1 0 46122 1 0 46123 1 0 47124 1 0 48125 1 0 49126 1 0 50127 1 0 50128 1 0 50129 1 0 53130 1 0 54131 1 0 55132 1 0 56133 1 0 57134 1 0 58135 1 0 58136 1 0 59137 1 0 61138 1 0 62139 1 0 63140 1 0 67141 1 0 67142 1 0 67143 1 0 68144 1 0 M END

Standard InCHIKey	YFGQJKBUXPKSAW-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C49H76O19/c1-22-43(66-38-18-33(53)44(23(2)61-38)67-39-19-34(63-25(4)51)45(24(3)62-39)68-46-42(57)41(56)40(55)35(20-50)65-46)32(52)17-37(60-22)64-28-9-12-47(5)27(16-28)7-8-31-30(47)10-13-48(6)29(11-14-49(31,48)58)26-15-36(54)59-21-26/h15,22-24,27-35,37-46,50,52-53,55-58H,7-14,16-21H2,1-6H3
SMILES	CC1C(C(CC(O1)OC1CCC2(C)C(CCC3C2CCC2(C)C(CCC32O)C2=CC(=O)OC2)C1)O)OC1CC(C(C(C)O1)OC1CC(C(C(C)O1)OC1C(C(C(C(CO)O1)O)O)O)OC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	968.5	Volume:	938.157 ? Van der Waals volume.
Dense:	1.032	LogP:	1.5 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.084 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.131 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	12.0	Rigid Bonds:	51.0
TPSA:	268.05 ? Topological Polar Surface Area.	H-Bond Acceptor:	19.0
H-Bond Donor:	7.0	Rings:	9.0
Heavy Atoms:	19.0

MedChem Properties

QED Drug-Likeness Score:	0.115	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.518	Fsp³:	0.918
MCE-18:	171.319 ? 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:	0.004	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.244 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.384	Promiscuous compounds:	0.029

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.666	MDCK Permeability:	-5.172
Pgp-inhibitor:	0.0	Pgp-substrate:	0.237
PAMPA:	0.987 ? 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):	0.138
20% Bioavailability (F20%):	0.0	30% Bioavailability (F30%):	0.034
50% Bioavailability (F50%):	0.854

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.135	MRP1:	1.0
Plasma Protein Binding (PPB):	38.697%	Volume Distribution (VD):	-0.633
Fu:	45.335% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.026	BCRP inhibitor:	0.0
BSEP inhibitor:	0.873

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.494	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.952	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.01	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):

0.75

Half-life (T1/2):

5.452

ADMET: Toxicity

hERG Blockers:	0.24	hERG Blockers (10um):	0.679
Human Hepatotoxicity (H-HT):	0.799	Drug-induced Liver Injury (DILI):	0.72
AMES Toxicity:	0.888	Rat Oral Acute Toxicity:	0.932
Maximum Recommended Daily Dose:	0.993	Skin Sensitization:	0.106
Carcinogencity:	0.125	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.051
Drug-induced Neurotoxicity:	0.204	Ototoxicity:	1.0
Hematotoxicity:	0.019	Drug-induced Nephrotoxicity:	0.041
Genotoxicity:	0.514	RPMI-8226 Immunitoxicity:	0.634
A549 Cytotoxicity:	0.21	Hek293 Cytotoxicity:	0.983
BCF:	0.261 ? 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:	3.929 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.097 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.301 ? 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]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0176-1617(89)80112-9]
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]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
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]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4443	Digitalis purpurea	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22245	Digitalis lanata	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[TCM_Taiwan]
NPO22245	Digitalis lanata	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[TM-MC]
NPO22245	Digitalis lanata	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
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
-	Mus musculus	LD50	=	4.685351146	mg/kg	TOXRIC

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 NPC146414 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	16988
0.1-0.2	27675
0.2-0.3	4346
0.3-0.4	630
0.4-0.5	78
0.5-0.6	62
0.6-0.7	48
0.7-0.8	2
0.8-0.85	1
0.85-0.9	4
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC74259
0.8632	High Similarity	NPC117445
0.8632	High Similarity	NPC474908
0.8632	High Similarity	NPC308262
0.8526	High Similarity	NPC120390
0.8125	Intermediate Similarity	NPC475590
0.7959	Intermediate Similarity	NPC475419
0.7822	Intermediate Similarity	NPC474423
0.7684	Intermediate Similarity	NPC486143
0.7684	Intermediate Similarity	NPC125077
0.7684	Intermediate Similarity	NPC486142
0.7684	Intermediate Similarity	NPC486149
0.764	Intermediate Similarity	NPC5311
0.7609	Intermediate Similarity	NPC72260
0.7553	Intermediate Similarity	NPC236973
0.7526	Intermediate Similarity	NPC329986
0.7526	Intermediate Similarity	NPC140092
0.7526	Intermediate Similarity	NPC486146
0.75	Intermediate Similarity	NPC208193
0.7374	Intermediate Similarity	NPC475219
0.7228	Intermediate Similarity	NPC486144
0.7228	Intermediate Similarity	NPC486145
0.7228	Intermediate Similarity	NPC486147
0.7228	Intermediate Similarity	NPC486148
0.7184	Intermediate Similarity	NPC329675
0.7083	Intermediate Similarity	NPC30483
0.7083	Intermediate Similarity	NPC470897
0.7019	Intermediate Similarity	NPC486134
0.7019	Intermediate Similarity	NPC486141
0.701	Intermediate Similarity	NPC292467
0.6939	Remote Similarity	NPC475556
0.6939	Remote Similarity	NPC311706
0.6848	Remote Similarity	NPC99620
0.6848	Remote Similarity	NPC471633
0.68	Remote Similarity	NPC55532
0.68	Remote Similarity	NPC486135
0.68	Remote Similarity	NPC486137
0.6733	Remote Similarity	NPC232785
0.6733	Remote Similarity	NPC486139
0.6702	Remote Similarity	NPC77299
0.6702	Remote Similarity	NPC480906
0.6667	Remote Similarity	NPC146857
0.6667	Remote Similarity	NPC32177
0.6667	Remote Similarity	NPC469756
0.6667	Remote Similarity	NPC275901
0.6632	Remote Similarity	NPC480914
0.6602	Remote Similarity	NPC486138
0.6602	Remote Similarity	NPC276838
0.66	Remote Similarity	NPC188234
0.6535	Remote Similarity	NPC231518
0.6535	Remote Similarity	NPC488944
0.6476	Remote Similarity	NPC488943
0.6476	Remote Similarity	NPC488942
0.6465	Remote Similarity	NPC173555
0.6436	Remote Similarity	NPC240070
0.6429	Remote Similarity	NPC193893
0.6415	Remote Similarity	NPC486136
0.6364	Remote Similarity	NPC480907
0.6289	Remote Similarity	NPC84949
0.6289	Remote Similarity	NPC76572
0.6289	Remote Similarity	NPC480562
0.6289	Remote Similarity	NPC74945
0.6289	Remote Similarity	NPC31354
0.6289	Remote Similarity	NPC193382
0.6289	Remote Similarity	NPC69576
0.6275	Remote Similarity	NPC480910
0.6275	Remote Similarity	NPC480909
0.6239	Remote Similarity	NPC194716
0.6182	Remote Similarity	NPC486150
0.6168	Remote Similarity	NPC479360
0.6168	Remote Similarity	NPC479359
0.6168	Remote Similarity	NPC488938
0.6168	Remote Similarity	NPC488937
0.6126	Remote Similarity	NPC488945
0.6126	Remote Similarity	NPC488946
0.6058	Remote Similarity	NPC475629
0.6036	Remote Similarity	NPC329784
0.602	Remote Similarity	NPC469750
0.5962	Remote Similarity	NPC479353
0.5962	Remote Similarity	NPC479354
0.5962	Remote Similarity	NPC486130
0.5918	Remote Similarity	NPC84987
0.5905	Remote Similarity	NPC488941
0.5905	Remote Similarity	NPC488940
0.5905	Remote Similarity	NPC486127
0.5888	Remote Similarity	NPC488939
0.5865	Remote Similarity	NPC40749
0.5842	Remote Similarity	NPC484202
0.5842	Remote Similarity	NPC93883
0.5818	Remote Similarity	NPC329636
0.581	Remote Similarity	NPC32793
0.581	Remote Similarity	NPC116075
0.58	Remote Similarity	NPC199428
0.58	Remote Similarity	NPC109448
0.58	Remote Similarity	NPC310341
0.5789	Remote Similarity	NPC488947
0.5686	Remote Similarity	NPC483822
0.566	Remote Similarity	NPC608063
0.5636	Remote Similarity	NPC479357
0.5636	Remote Similarity	NPC486132
0.5636	Remote Similarity	NPC486131
0.56	Remote Similarity	NPC196429
0.5586	Remote Similarity	NPC486128
0.5534	Remote Similarity	NPC471353
0.55	Remote Similarity	NPC473852
0.5495	Remote Similarity	NPC476221
0.5495	Remote Similarity	NPC477709
0.5463	Remote Similarity	NPC264336
0.5398	Remote Similarity	NPC479358
0.5392	Remote Similarity	NPC157376
0.5392	Remote Similarity	NPC142066
0.5392	Remote Similarity	NPC480915
0.5392	Remote Similarity	NPC603972
0.5391	Remote Similarity	NPC486140
0.5364	Remote Similarity	NPC469749
0.5347	Remote Similarity	NPC99728
0.5347	Remote Similarity	NPC87250
0.5347	Remote Similarity	NPC244402
0.5347	Remote Similarity	NPC50305
0.5345	Remote Similarity	NPC486133
0.5315	Remote Similarity	NPC247190
0.5294	Remote Similarity	NPC286809
0.5273	Remote Similarity	NPC59288
0.5248	Remote Similarity	NPC474418
0.5243	Remote Similarity	NPC17896
0.5243	Remote Similarity	NPC469755
0.5243	Remote Similarity	NPC284406
0.5243	Remote Similarity	NPC99080
0.5243	Remote Similarity	NPC197707
0.5243	Remote Similarity	NPC251866
0.5238	Remote Similarity	NPC179412
0.5238	Remote Similarity	NPC471356
0.5238	Remote Similarity	NPC305574
0.5234	Remote Similarity	NPC103534
0.5234	Remote Similarity	NPC44899
0.5234	Remote Similarity	NPC304260
0.5234	Remote Similarity	NPC29639
0.5192	Remote Similarity	NPC243196
0.5182	Remote Similarity	NPC610296
0.5124	Remote Similarity	NPC486152

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC146414 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6537
0.1-0.2	2511
0.2-0.3	83
0.3-0.4	4
0.4-0.5	5
0.5-0.6	1
0.6-0.7	6
0.7-0.8	2
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
0.7609	Intermediate Similarity	NPD8294	Phase 4
0.75	Intermediate Similarity	NPD8377	Phase 4
0.6535	Remote Similarity	NPD8033	Approved
0.6495	Remote Similarity	NPD8380	Approved
0.6465	Remote Similarity	NPD8296	Phase 4
0.6408	Remote Similarity	NPD8378	Pre-clinical
0.6408	Remote Similarity	NPD8379	Approved
0.6224	Remote Similarity	NPD8335	Phase 4
0.5243	Remote Similarity	NPD7319	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