NPASS Compound

Natural Product: NPC253702

Natural Product ID	NPC253702
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OOILDDLOYMBZCS-KBBPZTQESA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	6325783
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides [CHEMONTID:0001580] Triterpene glycosides [CHEMONTID:0002358] Triterpene saponins

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

Chemical Representations

RDKit 3D 139146 0 0 0 0 0 0 0 0999 V2000 3.6097 -1.7469 -3.1262 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7636 -0.9635 -2.1280 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8935 -1.5680 -0.7696 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0401 -0.9663 -0.0377 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8094 0.5328 0.0675 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7993 1.0207 -0.9058 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1402 0.3416 -2.1441 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5477 0.7088 -0.7103 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5207 1.5529 -0.8848 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3130 1.3667 -2.1216 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7570 1.1007 -1.9034 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0433 0.1345 -0.7675 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4799 -1.1998 -1.3100 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3628 0.5385 0.4671 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1801 0.8323 1.6652 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6372 0.5997 1.5850 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0401 -0.5046 0.6321 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.3263 -1.7542 1.1096 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5337 -0.0547 -0.7162 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2847 1.1453 -1.1816 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7445 1.0805 -0.9000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3094 0.2354 -0.1028 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7688 0.1695 0.1821 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.6190 0.8202 -0.8332 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.0675 0.6302 -0.4520 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.4575 -0.8253 -0.7480 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.9856 1.4759 -1.3153 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3988 0.9008 0.9695 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3884 0.3783 1.9559 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9708 0.7466 1.5356 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9771 0.1354 2.4743 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1539 -0.9815 1.9405 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4990 -0.7870 0.6280 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6882 -2.0737 -0.1960 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8277 2.2193 1.4983 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8602 2.7515 2.1441 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6393 3.1040 0.8318 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3336 1.6718 0.3073 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9796 3.0290 0.4484 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5366 1.5225 1.5640 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6238 0.9377 1.3700 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2641 -1.2182 -0.5859 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0914 -1.8374 0.3078 C 0 0 2 0 0 0 0 0 0 0 0 0 7.3531 -1.0618 0.6058 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3091 -2.2237 0.9163 C 0 0 2 0 0 0 0 0 0 0 0 0 7.8220 -3.2275 -0.1091 C 0 0 1 0 0 0 0 0 0 0 0 0 8.2906 -4.6288 0.2255 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6079 -5.5814 -0.7310 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2209 -5.3807 -0.6416 O 0 0 0 0 0 0 0 0 0 0 0 0 9.6542 -4.7802 0.1805 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4629 -3.1225 -0.0624 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0950 -2.7422 2.1828 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8540 -0.3640 -0.4765 O 0 0 0 0 0 0 0 0 0 0 0 0 8.1247 0.9471 -0.0832 C 0 0 1 0 0 0 0 0 0 0 0 0 9.6051 1.2529 -0.1667 C 0 0 1 0 0 0 0 0 0 0 0 0 9.8618 2.7178 -0.0664 C 0 0 2 0 0 0 0 0 0 0 0 0 8.7532 3.6031 -0.5251 C 0 0 1 0 0 0 0 0 0 0 0 0 7.3773 3.0384 -0.3139 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3616 1.7774 -0.9080 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8110 4.8220 0.1908 O 0 0 0 0 0 0 0 0 0 0 0 0 10.9744 2.9998 -0.8927 O 0 0 0 0 0 0 0 0 0 0 0 0 10.1886 0.6692 0.9827 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1231 -2.9538 -0.9899 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2487 -2.7864 -3.1556 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6500 -1.7610 -2.7530 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6435 -1.2588 -4.1154 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6659 -1.0954 -2.4092 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9262 -1.4754 -0.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0199 -1.3589 1.0056 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8220 0.9913 -0.2130 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0618 2.0628 -1.1935 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0308 2.5589 -1.0459 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2784 2.3226 -2.7359 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0892 0.6321 -2.8471 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3116 2.0320 -1.8689 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1581 0.5630 -2.8189 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7002 -1.0490 -2.0596 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2658 -1.8036 -1.7986 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9877 -1.7735 -0.4839 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6789 -0.3294 0.7452 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8035 0.2669 2.5728 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0513 1.9039 1.9995 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0525 0.3180 2.5784 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1686 1.5278 1.2888 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1092 -2.4808 0.3205 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4647 -1.5182 1.7776 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0387 -2.2850 1.8033 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8331 -0.8803 -1.4317 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2008 1.1693 -2.3086 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9629 2.1106 -0.7407 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3675 1.8213 -1.4241 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0799 -0.9037 0.2422 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.5322 0.3100 -1.8490 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.4291 1.8801 -1.0466 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9714 -1.1905 -1.6510 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.5800 -0.9106 -0.7922 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.1471 -1.4589 0.1090 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.1559 2.4974 -0.8660 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.9894 0.9874 -1.2622 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6909 1.5101 -2.3712 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6576 1.9748 1.1503 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3595 0.3480 1.1946 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.4483 -0.7075 2.0049 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6402 0.7930 2.9523 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3853 0.9585 2.9268 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5500 -0.2934 3.3502 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8534 -1.8731 1.8966 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4576 -1.2720 2.7794 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0859 -2.9063 0.1732 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5909 -1.8985 -1.2686 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7575 -2.4064 -0.0426 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8982 4.0180 1.1742 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8271 3.4686 1.4546 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0688 2.9895 0.3024 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4938 3.7618 -0.2612 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3062 2.2914 1.5843 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9858 0.5195 1.5911 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1116 1.5839 2.4815 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7868 1.9022 1.4466 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5478 -1.9582 1.2722 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2754 -0.4691 1.5280 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3610 -1.9423 0.7614 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2528 -2.9964 -1.1263 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9407 -4.9058 1.2495 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8123 -6.6315 -0.5210 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8806 -5.3605 -1.8004 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7358 -5.8674 -1.3570 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1172 -4.0387 -0.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0480 -2.0080 2.8590 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8580 1.0939 1.0050 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0935 0.7665 -1.0356 H 0 0 0 0 0 0 0 0 0 0 0 0 10.1668 3.0425 0.9493 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8638 3.9185 -1.6021 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0957 3.0348 0.7443 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6712 3.6707 -0.9313 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5197 5.4166 -0.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 11.6366 2.2860 -0.8866 H 0 0 0 0 0 0 0 0 0 0 0 0 11.1950 0.7224 0.9018 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0228 -3.1357 -1.3088 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 6 12 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 1 17 19 1 0 19 20 1 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 25 27 1 0 25 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 30 35 1 0 35 36 2 0 35 37 1 0 14 38 1 0 38 39 1 0 38 40 1 0 5 41 1 0 4 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 47 50 1 0 46 51 1 0 45 52 1 0 44 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 3 63 1 0 7 2 1 0 38 9 1 0 51 43 1 0 59 54 1 0 19 12 1 0 33 22 1 0 33 17 1 0 30 23 1 0 1 64 1 0 1 65 1 0 1 66 1 0 2 67 1 6 3 68 1 1 4 69 1 1 5 70 1 6 6 71 1 6 9 72 1 6 10 73 1 0 10 74 1 0 11 75 1 0 11 76 1 0 13 77 1 0 13 78 1 0 13 79 1 0 14 80 1 0 15 81 1 0 15 82 1 0 16 83 1 0 16 84 1 0 18 85 1 0 18 86 1 0 18 87 1 0 19 88 1 0 20 89 1 0 20 90 1 0 21 91 1 0 23 92 1 1 24 93 1 0 24 94 1 0 26 95 1 0 26 96 1 0 26 97 1 0 27 98 1 0 27 99 1 0 27100 1 0 28101 1 0 28102 1 0 29103 1 0 29104 1 0 31105 1 0 31106 1 0 32107 1 0 32108 1 0 34109 1 0 34110 1 0 34111 1 0 37112 1 0 39113 1 0 39114 1 0 39115 1 0 40116 1 0 40117 1 0 40118 1 0 41119 1 0 43120 1 1 44121 1 1 45122 1 6 46123 1 6 47124 1 0 48125 1 0 48126 1 0 49127 1 0 50128 1 0 52129 1 0 54130 1 1 55131 1 6 56132 1 1 57133 1 6 58134 1 0 58135 1 0 60136 1 0 61137 1 0 62138 1 0 63139 1 0 M END

Standard InCHIKey	OOILDDLOYMBZCS-KBBPZTQESA-N
Standard InCHI	InChI=1S/C47H76O16/c1-22-30(51)36(62-40-37(33(54)35(61-40)25(49)20-48)63-38-32(53)31(52)26(50)21-58-38)34(55)39(59-22)60-29-12-13-44(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)/t22-,24-,25?,26+,27?,28?,29-,30+,31-,32+,33-,34-,35+,36+,37+,38-,39-,40+,44-,45?,46+,47?/m0/s1
SMILES	C[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)O[C@H]1CC[C@@]2(C)C(CC[C@]3(C)C2CC=C2[C@@H]4CC(C)(C)CCC4(CCC32C)C(=O)O)C1(C)C)O)O[C@@H]1[C@@H]([C@H]([C@@H](C(CO)O)O1)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	896.51	Volume:	888.387 ? Van der Waals volume.
Dense:	1.009	LogP:	2.437 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.07 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.87 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	44.0
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:	0.119	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.268	Fsp³:	0.936
MCE-18:	170.33 ? 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:	0.919	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.001 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.005 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.142	Promiscuous compounds:	0.053

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.987	MDCK Permeability:	-5.207
Pgp-inhibitor:	0.0	Pgp-substrate:	0.098
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):	0.002
20% Bioavailability (F20%):	0.008	30% Bioavailability (F30%):	0.01
50% Bioavailability (F50%):	0.927

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.814
Plasma Protein Binding (PPB):	76.159%	Volume Distribution (VD):	-0.504
Fu:	13.634% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.989	BCRP inhibitor:	0.0
BSEP inhibitor:	0.104

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.012	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.006	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.236
HLM stability:	0.302 ? 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):

0.052

Half-life (T1/2):

2.8

ADMET: Toxicity

hERG Blockers:	0.006	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.453	Drug-induced Liver Injury (DILI):	0.282
AMES Toxicity:	0.36	Rat Oral Acute Toxicity:	0.03
Maximum Recommended Daily Dose:	0.075	Skin Sensitization:	0.989
Carcinogencity:	0.015	Eye Corrosion:	0.0
Eye Irritation:	0.001	Respiratory Toxicity:	0.022
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.999
Hematotoxicity:	0.307	Drug-induced Nephrotoxicity:	0.82
Genotoxicity:	0.015	RPMI-8226 Immunitoxicity:	0.118
A549 Cytotoxicity:	0.153	Hek293 Cytotoxicity:	0.24
BCF:	1.024 ? 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:	4.075 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.917 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.704 ? 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
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20930	Patrinia scabiosifolia	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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 NPC253702 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	22660
0.1-0.2	23545
0.2-0.3	2396
0.3-0.4	810
0.4-0.5	330
0.5-0.6	59
0.6-0.7	33
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
0.8469	Intermediate Similarity	NPC481082
0.8469	Intermediate Similarity	NPC164419
0.7944	Intermediate Similarity	NPC166422
0.7802	Intermediate Similarity	NPC283849
0.7692	Intermediate Similarity	NPC324875
0.7692	Intermediate Similarity	NPC292677
0.7677	Intermediate Similarity	NPC488561
0.7364	Intermediate Similarity	NPC323341
0.7353	Intermediate Similarity	NPC469945
0.7327	Intermediate Similarity	NPC6377
0.7327	Intermediate Similarity	NPC208381
0.7297	Intermediate Similarity	NPC219180
0.7234	Intermediate Similarity	NPC28198
0.7234	Intermediate Similarity	NPC476123
0.7212	Intermediate Similarity	NPC104400
0.7212	Intermediate Similarity	NPC10320
0.7143	Intermediate Similarity	NPC251263
0.7129	Intermediate Similarity	NPC56713
0.7115	Intermediate Similarity	NPC114304
0.7103	Intermediate Similarity	NPC276093
0.6893	Remote Similarity	NPC127056
0.687	Remote Similarity	NPC54636
0.6864	Remote Similarity	NPC471385
0.6864	Remote Similarity	NPC161717
0.6837	Remote Similarity	NPC100383
0.6796	Remote Similarity	NPC25605
0.6759	Remote Similarity	NPC257468
0.6754	Remote Similarity	NPC471384
0.6697	Remote Similarity	NPC79718
0.6667	Remote Similarity	NPC488209
0.6667	Remote Similarity	NPC164194
0.6635	Remote Similarity	NPC174679
0.6635	Remote Similarity	NPC279554
0.6609	Remote Similarity	NPC133818
0.6607	Remote Similarity	NPC475486
0.6574	Remote Similarity	NPC180550
0.6574	Remote Similarity	NPC35405
0.6549	Remote Similarity	NPC280941
0.6549	Remote Similarity	NPC235772
0.6531	Remote Similarity	NPC606107
0.65	Remote Similarity	NPC242611
0.6455	Remote Similarity	NPC73829
0.6415	Remote Similarity	NPC114441
0.6355	Remote Similarity	NPC472949
0.6346	Remote Similarity	NPC270667
0.6321	Remote Similarity	NPC59804
0.6238	Remote Similarity	NPC286347
0.6228	Remote Similarity	NPC488564
0.6226	Remote Similarity	NPC12288
0.6216	Remote Similarity	NPC139044
0.6216	Remote Similarity	NPC471383
0.6106	Remote Similarity	NPC488515
0.6	Remote Similarity	NPC323359
0.5965	Remote Similarity	NPC119794
0.5963	Remote Similarity	NPC109079
0.5941	Remote Similarity	NPC204407
0.5932	Remote Similarity	NPC288205
0.5932	Remote Similarity	NPC51465
0.5926	Remote Similarity	NPC136877
0.5909	Remote Similarity	NPC488516
0.5905	Remote Similarity	NPC284807
0.5856	Remote Similarity	NPC80843
0.5856	Remote Similarity	NPC22956
0.5825	Remote Similarity	NPC177246
0.5763	Remote Similarity	NPC481078
0.5693	Remote Similarity	NPC40085
0.5684	Remote Similarity	NPC120840
0.5596	Remote Similarity	NPC127853
0.5583	Remote Similarity	NPC62725
0.5556	Remote Similarity	NPC191410
0.5556	Remote Similarity	NPC484832
0.5537	Remote Similarity	NPC476992
0.5508	Remote Similarity	NPC37134
0.55	Remote Similarity	NPC264270
0.5484	Remote Similarity	NPC123199
0.5472	Remote Similarity	NPC31839
0.5463	Remote Similarity	NPC294112
0.5462	Remote Similarity	NPC75318
0.5385	Remote Similarity	NPC258885
0.5385	Remote Similarity	NPC111466
0.5366	Remote Similarity	NPC473824
0.5364	Remote Similarity	NPC475472
0.5333	Remote Similarity	NPC291903
0.5321	Remote Similarity	NPC473538
0.5317	Remote Similarity	NPC475140
0.5285	Remote Similarity	NPC475119
0.5263	Remote Similarity	NPC480424
0.5234	Remote Similarity	NPC4749
0.5234	Remote Similarity	NPC488211
0.5207	Remote Similarity	NPC301449
0.5207	Remote Similarity	NPC601290
0.52	Remote Similarity	NPC79643
0.5172	Remote Similarity	NPC469946
0.5152	Remote Similarity	NPC236638
0.5152	Remote Similarity	NPC294453
0.5149	Remote Similarity	NPC488212
0.5122	Remote Similarity	NPC477194
0.512	Remote Similarity	NPC475287
0.5116	Remote Similarity	NPC481080
0.5111	Remote Similarity	NPC250247
0.5109	Remote Similarity	NPC488210
0.5089	Remote Similarity	NPC480938
0.5083	Remote Similarity	NPC275668
0.5083	Remote Similarity	NPC475504
0.5082	Remote Similarity	NPC481079
0.5081	Remote Similarity	NPC480939
0.5052	Remote Similarity	NPC480946
0.5052	Remote Similarity	NPC130577
0.5052	Remote Similarity	NPC142415
0.5052	Remote Similarity	NPC102683
0.5043	Remote Similarity	NPC475296
0.5039	Remote Similarity	NPC243680

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC253702 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6750
0.1-0.2	2355
0.2-0.3	39
0.3-0.4	5
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
0.5175	Remote Similarity	NPD8295	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