NPASS Compound

Natural Product: NPC194282

Natural Product ID	NPC194282
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VQQGPFFHGWNIGX-UHFFFAOYSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	343425
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 139146 0 0 0 0 0 0 0 0999 V2000 -12.4251 -1.4353 0.2089 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9580 -1.7056 0.4729 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.8686 -2.0781 1.9541 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4676 -2.6503 2.1297 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5167 -1.5663 1.6967 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8306 -0.9647 0.3634 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.1662 -0.6121 0.2048 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.9782 0.1115 0.1802 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.1030 0.0089 -0.8758 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2596 1.1692 -1.8554 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7773 2.3957 -1.1638 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5717 2.2369 0.3175 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8314 3.4890 0.7978 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5854 3.5377 0.2257 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8317 1.1505 0.6967 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7015 0.1834 -0.3085 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8778 0.7645 -1.2699 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6844 0.0410 -1.4678 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6758 -0.3451 -2.9143 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5427 0.8868 -3.7661 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5198 1.8553 -3.2180 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7858 2.1621 -1.8852 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5422 0.9573 -1.1714 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3216 0.4852 -1.6375 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3377 0.5122 -0.6444 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6790 1.5109 -1.1221 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8601 1.7312 -0.2615 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3686 0.4391 0.4133 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7262 0.5051 1.8109 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8304 -0.6613 -0.4342 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5305 -1.9695 -0.3457 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7703 -1.9878 0.4787 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5981 -0.7696 0.1619 C 0 0 0 0 0 0 0 0 0 0 0 0 5.0362 -0.7029 -1.2801 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8350 0.4368 0.6112 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5694 1.6268 0.0006 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9607 1.5800 0.5941 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5446 0.4698 1.0122 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9153 0.5804 1.5714 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7274 1.7350 1.0785 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2807 1.6192 -0.2985 C 0 0 0 0 0 0 0 0 0 0 0 0 10.5740 2.4538 -0.3224 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4196 2.1908 -1.3906 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6549 0.1995 -0.6653 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9535 -0.5533 0.5976 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7413 -0.6569 1.5161 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0599 -1.9298 1.2126 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8633 -1.8187 0.3169 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8731 -0.8814 0.9698 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6377 -1.4116 2.3566 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3664 -0.8283 2.8852 C 0 0 0 0 0 0 0 0 0 0 0 0 9.1638 -0.0203 3.8195 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1872 -1.9123 3.1096 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3288 -0.8082 -0.4166 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0017 -1.7300 -1.5786 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2463 -1.4385 0.8041 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1176 0.5626 -5.0728 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6976 -1.2815 -3.2502 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7944 3.3679 -1.3145 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.5449 1.2558 -2.3533 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2065 -2.0891 1.6374 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3106 -3.8352 1.4155 O 0 0 0 0 0 0 0 0 0 0 0 0 -11.7855 -3.0560 2.2482 O 0 0 0 0 0 0 0 0 0 0 0 0 -12.9083 -2.2681 -0.3248 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.5032 -0.4635 -0.3487 H 0 0 0 0 0 0 0 0 0 0 0 0 -13.0021 -1.2838 1.1502 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6940 -2.6168 -0.0958 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.9678 -1.2171 2.6136 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3059 -2.8617 3.1963 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4996 -0.8199 2.5189 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5993 -1.7130 -0.4202 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2673 -0.9541 -1.3660 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5913 0.9478 -2.7102 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8772 2.8477 -1.6070 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5713 2.3084 0.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7965 3.4532 1.9208 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4772 4.3604 0.4879 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4439 4.4306 -0.1533 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2920 -0.7265 0.1285 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6764 -0.8644 -0.8073 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6939 -0.7615 -3.1439 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5097 1.4070 -3.7812 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6161 2.7972 -3.7952 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4903 1.5100 -3.3053 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4798 1.2132 -0.0765 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8824 0.8989 0.2704 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9259 1.2662 -2.1746 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1256 2.4950 -1.1886 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6693 2.1091 -0.9572 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6709 2.5204 0.4747 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8554 1.1525 1.8580 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6510 -0.4837 2.2632 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4717 1.0440 2.4814 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0044 -0.3173 -1.5089 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8410 -2.3851 -1.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8718 -2.7950 0.0629 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5110 -1.9825 1.5302 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3114 -2.9345 0.2635 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3386 -0.2366 -1.9685 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9577 -0.0490 -1.3306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2465 -1.7263 -1.6540 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0986 0.5531 1.7122 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0733 2.5429 0.4314 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6371 1.6067 -1.0788 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4615 2.5591 0.6634 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7139 0.8397 2.6653 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3062 2.7320 1.2419 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6474 1.7360 1.7687 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6701 3.0526 -1.2266 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6530 3.1033 0.5696 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4512 1.7711 -0.2828 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0040 3.1708 -1.0784 H 0 0 0 0 0 0 0 0 0 0 0 0 7.6840 1.5115 -1.8133 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1197 2.4370 -2.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 10.6237 0.2191 -1.2380 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9272 -0.2603 -1.3300 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7969 -0.0186 1.1008 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2996 -1.5764 0.3558 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7680 -2.6424 0.7018 H 0 0 0 0 0 0 0 0 0 0 0 0 7.7541 -2.4856 2.1400 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3654 -2.8351 0.3479 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0674 -1.6353 -0.7293 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7316 -1.0251 2.8452 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4933 -1.1442 3.0073 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5598 -2.5174 2.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 10.4442 -2.1974 4.0386 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9643 -2.2706 -1.3930 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8354 -2.4677 -1.6581 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0452 -1.1992 -2.5348 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2087 -1.9507 0.4881 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6240 -0.7045 1.5689 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3413 -2.2204 1.2766 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1409 1.4236 -5.5657 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0443 -2.1724 -3.0670 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6878 2.9388 -1.2761 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0213 0.3827 -2.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1224 -2.6239 2.4805 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6300 -4.5663 2.0026 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5394 -3.8796 1.7406 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 12 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 1 0 40 41 1 0 41 42 1 0 41 43 1 0 41 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 46 51 1 0 51 52 2 0 51 53 1 0 30 54 1 0 54 55 1 0 54 56 1 0 20 57 1 0 19 58 1 0 11 59 1 0 10 60 1 0 5 61 1 0 4 62 1 0 3 63 1 0 7 2 1 0 16 9 1 0 23 18 1 0 54 25 1 0 35 28 1 0 49 38 1 0 49 33 1 0 46 39 1 0 1 64 1 0 1 65 1 0 1 66 1 0 2 67 1 0 3 68 1 0 4 69 1 0 5 70 1 0 6 71 1 0 9 72 1 0 10 73 1 0 11 74 1 0 12 75 1 0 13 76 1 0 13 77 1 0 14 78 1 0 16 79 1 0 18 80 1 0 19 81 1 0 20 82 1 0 21 83 1 0 21 84 1 0 23 85 1 0 25 86 1 0 26 87 1 0 26 88 1 0 27 89 1 0 27 90 1 0 29 91 1 0 29 92 1 0 29 93 1 0 30 94 1 0 31 95 1 0 31 96 1 0 32 97 1 0 32 98 1 0 34 99 1 0 34100 1 0 34101 1 0 35102 1 0 36103 1 0 36104 1 0 37105 1 0 39106 1 0 40107 1 0 40108 1 0 42109 1 0 42110 1 0 42111 1 0 43112 1 0 43113 1 0 43114 1 0 44115 1 0 44116 1 0 45117 1 0 45118 1 0 47119 1 0 47120 1 0 48121 1 0 48122 1 0 50123 1 0 50124 1 0 50125 1 0 53126 1 0 55127 1 0 55128 1 0 55129 1 0 56130 1 0 56131 1 0 56132 1 0 57133 1 0 58134 1 0 59135 1 0 60136 1 0 61137 1 0 62138 1 0 63139 1 0 M END

Standard InCHIKey	VQQGPFFHGWNIGX-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C47H76O16/c1-22-30(50)33(53)35(55)38(59-22)62-37-34(54)32(52)26(20-48)60-40(37)63-36-31(51)25(49)21-58-39(36)61-29-12-13-44(6)27(43(29,4)5)11-14-46(8)28(44)10-9-23-24-19-42(2,3)15-17-47(24,41(56)57)18-16-45(23,46)7/h9,22,24-40,48-55H,10-21H2,1-8H3,(H,56,57)
SMILES	CC1C(C(C(C(O1)OC1C(C(C(CO)OC1OC1C(C(COC1OC1CCC2(C)C(CCC3(C)C2CC=C2C4CC(C)(C)CCC4(CCC32C)C(=O)O)C1(C)C)O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	896.51	Volume:	888.387 ? Van der Waals volume.
Dense:	1.009	LogP:	2.16 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.013 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.544 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	45.0
TPSA:	254.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	16.0
H-Bond Donor:	9.0	Rings:	8.0
Heavy Atoms:	16.0

MedChem Properties

QED Drug-Likeness Score:	0.125	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.175	Fsp³:	0.936
MCE-18:	171.692 ? 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:	0.25	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.323 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.2	Promiscuous compounds:	0.001

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.165	MDCK Permeability:	-5.007
Pgp-inhibitor:	0.0	Pgp-substrate:	0.338
PAMPA:	1.0 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.893
20% Bioavailability (F20%):	0.01	30% Bioavailability (F30%):	0.4
50% Bioavailability (F50%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	1.0
Plasma Protein Binding (PPB):	62.862%	Volume Distribution (VD):	-0.473
Fu:	25.376% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.087	BCRP inhibitor:	0.0
BSEP inhibitor:	0.023

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.904	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.973	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.002	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):

-0.051

Half-life (T1/2):

3.46

ADMET: Toxicity

hERG Blockers:	0.01	hERG Blockers (10um):	0.092
Human Hepatotoxicity (H-HT):	0.399	Drug-induced Liver Injury (DILI):	0.203
AMES Toxicity:	0.114	Rat Oral Acute Toxicity:	0.128
Maximum Recommended Daily Dose:	0.253	Skin Sensitization:	0.033
Carcinogencity:	0.012	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.008
Drug-induced Neurotoxicity:	0.154	Ototoxicity:	1.0
Hematotoxicity:	0.022	Drug-induced Nephrotoxicity:	0.053
Genotoxicity:	0.002	RPMI-8226 Immunitoxicity:	0.048
A549 Cytotoxicity:	0.02	Hek293 Cytotoxicity:	0.468
BCF:	1.147 ? 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:	4.4 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.395 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.816 ? 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
NPO10150	Anemone raddeana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10150	Anemone raddeana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10150	Anemone raddeana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10150	Anemone raddeana	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10150	Anemone raddeana	Species	Ranunculaceae	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 NPC194282 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	23113
0.1-0.2	22372
0.2-0.3	2819
0.3-0.4	865
0.4-0.5	448
0.5-0.6	121
0.6-0.7	45
0.7-0.8	0
0.8-0.85	9
0.85-0.9	1
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9011	High Similarity	NPC25605
0.9011	High Similarity	NPC56713
0.8913	High Similarity	NPC127056
0.8478	Intermediate Similarity	NPC164194
0.8421	Intermediate Similarity	NPC488561
0.8404	Intermediate Similarity	NPC174679
0.8404	Intermediate Similarity	NPC279554
0.84	Intermediate Similarity	NPC324875
0.84	Intermediate Similarity	NPC292677
0.8298	Intermediate Similarity	NPC12288
0.8211	Intermediate Similarity	NPC59804
0.81	Intermediate Similarity	NPC257468
0.798	Intermediate Similarity	NPC114304
0.7778	Intermediate Similarity	NPC219180
0.7778	Intermediate Similarity	NPC251263
0.7767	Intermediate Similarity	NPC276093
0.76	Intermediate Similarity	NPC80843
0.7573	Intermediate Similarity	NPC481082
0.7573	Intermediate Similarity	NPC164419
0.7476	Intermediate Similarity	NPC139044
0.7419	Intermediate Similarity	NPC606107
0.7379	Intermediate Similarity	NPC104400
0.7379	Intermediate Similarity	NPC10320
0.7333	Intermediate Similarity	NPC79718
0.7327	Intermediate Similarity	NPC472949
0.7304	Intermediate Similarity	NPC161717
0.7297	Intermediate Similarity	NPC166422
0.7228	Intermediate Similarity	NPC109079
0.7222	Intermediate Similarity	NPC475486
0.7207	Intermediate Similarity	NPC133818
0.7196	Intermediate Similarity	NPC323359
0.7184	Intermediate Similarity	NPC469945
0.713	Intermediate Similarity	NPC488564
0.7087	Intermediate Similarity	NPC22956
0.6981	Remote Similarity	NPC471383
0.6937	Remote Similarity	NPC288205
0.6937	Remote Similarity	NPC51465
0.6875	Remote Similarity	NPC283849
0.687	Remote Similarity	NPC54636
0.6771	Remote Similarity	NPC204407
0.6754	Remote Similarity	NPC323341
0.6697	Remote Similarity	NPC119794
0.6696	Remote Similarity	NPC280941
0.6696	Remote Similarity	NPC235772
0.6667	Remote Similarity	NPC488209
0.6667	Remote Similarity	NPC488211
0.6634	Remote Similarity	NPC191410
0.6579	Remote Similarity	NPC313110
0.6574	Remote Similarity	NPC180550
0.6574	Remote Similarity	NPC35405
0.6571	Remote Similarity	NPC114441
0.6549	Remote Similarity	NPC480939
0.6549	Remote Similarity	NPC62725
0.6542	Remote Similarity	NPC112352
0.6538	Remote Similarity	NPC136877
0.6476	Remote Similarity	NPC475296
0.6396	Remote Similarity	NPC488515
0.6379	Remote Similarity	NPC151543
0.6364	Remote Similarity	NPC28198
0.6364	Remote Similarity	NPC476123
0.6346	Remote Similarity	NPC270667
0.6311	Remote Similarity	NPC471385
0.6306	Remote Similarity	NPC73829
0.6273	Remote Similarity	NPC480475
0.624	Remote Similarity	NPC488212
0.6238	Remote Similarity	NPC31839
0.6207	Remote Similarity	NPC475119
0.6207	Remote Similarity	NPC476992
0.6186	Remote Similarity	NPC471384
0.6168	Remote Similarity	NPC474589
0.6154	Remote Similarity	NPC473824
0.6087	Remote Similarity	NPC187618
0.6078	Remote Similarity	NPC286347
0.6055	Remote Similarity	NPC6377
0.6055	Remote Similarity	NPC208381
0.6036	Remote Similarity	NPC160415
0.6019	Remote Similarity	NPC100383
0.6	Remote Similarity	NPC291903
0.6	Remote Similarity	NPC111466
0.5982	Remote Similarity	NPC164389
0.5965	Remote Similarity	NPC302887
0.5948	Remote Similarity	NPC480474
0.5943	Remote Similarity	NPC475472
0.5935	Remote Similarity	NPC484061
0.5935	Remote Similarity	NPC484062
0.5909	Remote Similarity	NPC488516
0.5877	Remote Similarity	NPC123796
0.5877	Remote Similarity	NPC131469
0.5865	Remote Similarity	NPC242611
0.5862	Remote Similarity	NPC218954
0.5856	Remote Similarity	NPC469946
0.5841	Remote Similarity	NPC148603
0.5826	Remote Similarity	NPC95437
0.5812	Remote Similarity	NPC480473
0.5812	Remote Similarity	NPC160452
0.5806	Remote Similarity	NPC21691
0.5794	Remote Similarity	NPC484059
0.5794	Remote Similarity	NPC484060
0.5789	Remote Similarity	NPC63159
0.5776	Remote Similarity	NPC114692
0.5776	Remote Similarity	NPC236657
0.5755	Remote Similarity	NPC284807
0.5738	Remote Similarity	NPC135904
0.5736	Remote Similarity	NPC484063
0.5736	Remote Similarity	NPC484064
0.5726	Remote Similarity	NPC23275
0.5693	Remote Similarity	NPC40085
0.5691	Remote Similarity	NPC475140
0.569	Remote Similarity	NPC486563
0.569	Remote Similarity	NPC484832
0.5678	Remote Similarity	NPC120116
0.5645	Remote Similarity	NPC277212
0.5645	Remote Similarity	NPC30279
0.5641	Remote Similarity	NPC37134
0.563	Remote Similarity	NPC469947
0.563	Remote Similarity	NPC480948
0.563	Remote Similarity	NPC481078
0.562	Remote Similarity	NPC60557
0.562	Remote Similarity	NPC475287
0.562	Remote Similarity	NPC67857
0.5612	Remote Similarity	NPC264270
0.5603	Remote Similarity	NPC275668
0.5603	Remote Similarity	NPC475504
0.5596	Remote Similarity	NPC76999
0.5593	Remote Similarity	NPC481079
0.5591	Remote Similarity	NPC225791
0.5586	Remote Similarity	NPC108748
0.5583	Remote Similarity	NPC470915
0.5574	Remote Similarity	NPC79643
0.5565	Remote Similarity	NPC283417
0.5565	Remote Similarity	NPC173859
0.5565	Remote Similarity	NPC471550
0.5565	Remote Similarity	NPC200049
0.5556	Remote Similarity	NPC57484
0.5521	Remote Similarity	NPC120840
0.552	Remote Similarity	NPC46823
0.5517	Remote Similarity	NPC162574
0.5508	Remote Similarity	NPC78034
0.55	Remote Similarity	NPC36831
0.5492	Remote Similarity	NPC268184
0.5463	Remote Similarity	NPC473538
0.5462	Remote Similarity	NPC301449
0.5462	Remote Similarity	NPC486564
0.5462	Remote Similarity	NPC75318
0.5462	Remote Similarity	NPC601290
0.5447	Remote Similarity	NPC123522
0.5439	Remote Similarity	NPC263756
0.5439	Remote Similarity	NPC213674
0.5431	Remote Similarity	NPC251768
0.5431	Remote Similarity	NPC46665
0.5429	Remote Similarity	NPC57362
0.5417	Remote Similarity	NPC470477
0.5398	Remote Similarity	NPC480424
0.5391	Remote Similarity	NPC192791
0.5391	Remote Similarity	NPC265841
0.5391	Remote Similarity	NPC488308
0.5385	Remote Similarity	NPC305981
0.5385	Remote Similarity	NPC118440
0.5366	Remote Similarity	NPC610204
0.536	Remote Similarity	NPC123199
0.5354	Remote Similarity	NPC181066
0.5354	Remote Similarity	NPC4749
0.5349	Remote Similarity	NPC312650
0.5349	Remote Similarity	NPC470876
0.5345	Remote Similarity	NPC480947
0.5345	Remote Similarity	NPC204392
0.5344	Remote Similarity	NPC261506
0.5344	Remote Similarity	NPC4328
0.5339	Remote Similarity	NPC297263
0.5333	Remote Similarity	NPC606145
0.5328	Remote Similarity	NPC480936
0.5321	Remote Similarity	NPC294112
0.5321	Remote Similarity	NPC475633
0.5299	Remote Similarity	NPC473383
0.5263	Remote Similarity	NPC488309
0.5254	Remote Similarity	NPC475591
0.5254	Remote Similarity	NPC236870
0.5246	Remote Similarity	NPC207738
0.5246	Remote Similarity	NPC187290
0.5246	Remote Similarity	NPC609281
0.5242	Remote Similarity	NPC76972
0.5242	Remote Similarity	NPC469782
0.5242	Remote Similarity	NPC204414
0.5234	Remote Similarity	NPC71391
0.5231	Remote Similarity	NPC271610
0.5231	Remote Similarity	NPC41061
0.5231	Remote Similarity	NPC227551
0.5231	Remote Similarity	NPC258617
0.5225	Remote Similarity	NPC473481
0.5217	Remote Similarity	NPC470512
0.521	Remote Similarity	NPC222580
0.5191	Remote Similarity	NPC293330
0.5172	Remote Similarity	NPC161674
0.5169	Remote Similarity	NPC44716
0.5167	Remote Similarity	NPC64715
0.5161	Remote Similarity	NPC471962
0.5159	Remote Similarity	NPC165204
0.5159	Remote Similarity	NPC243680
0.5156	Remote Similarity	NPC47995
0.5154	Remote Similarity	NPC286457

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC194282 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6827
0.1-0.2	2264
0.2-0.3	50
0.3-0.4	8
0.4-0.5	1
0.5-0.6	0
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
		NPD

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