NPASS Compound

Natural Product: NPC471464

Natural Product ID	NPC471464
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Filiasparoside C
IUPAC Name	n.a.
Synonyms	filiasparoside C
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL251480
PubChem CID	44445742
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides [CHEMONTID:0002364] Steroidal 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 131139 0 0 0 0 0 0 0 0999 V2000 12.9688 -1.0903 -1.5274 C 0 0 0 0 0 0 0 0 0 0 0 0 11.5193 -0.8804 -1.1859 C 0 0 0 0 0 0 0 0 0 0 0 0 10.6065 -1.0337 -2.3835 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3762 -1.8509 -2.0799 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8547 -1.4073 -0.7426 C 0 0 0 0 0 0 0 0 0 0 0 0 8.3230 0.0303 -0.9183 C 0 0 0 0 0 0 0 0 0 0 0 0 6.8923 -0.2844 -0.9668 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9412 -1.2750 0.2287 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7447 -2.1859 -0.3182 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5070 -1.4377 0.4468 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1612 0.0678 0.5258 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8138 0.6402 -0.7414 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8242 0.5025 -1.9116 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4701 1.0736 -1.5830 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8678 0.2249 -0.4847 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7588 0.3811 0.7175 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1911 -0.5160 1.7999 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8963 0.0761 2.2434 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2343 0.9585 1.2348 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4346 0.5066 -0.1963 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6490 -0.7327 -0.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5884 -0.9283 0.3339 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1903 0.3274 0.8541 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1867 1.1894 1.6034 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1972 0.0825 1.7490 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4525 0.6002 1.3880 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4372 -0.4846 1.2907 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7984 -0.0896 1.8957 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0109 1.3240 1.4685 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0193 2.1763 2.2036 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7924 1.6714 2.1787 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5248 2.5815 3.5756 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8091 3.0935 3.4643 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3232 1.7049 1.7021 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0046 2.1081 0.5496 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.1881 1.2615 0.2517 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8452 1.8486 -1.0035 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.2335 3.2712 -0.7982 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5705 3.8692 0.3982 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3469 3.4127 0.7357 O 0 0 0 0 0 0 0 0 0 0 0 0 -10.4959 3.6675 1.5971 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.6250 3.3494 -0.7390 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9433 1.6874 -2.0554 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8305 -0.2873 3.2543 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7575 -0.8967 -0.0022 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7558 -2.2632 -0.1780 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7995 -2.7246 -1.2282 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4331 -3.7523 -2.1551 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1428 -4.8008 -1.3442 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0789 -4.1402 -0.3923 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0547 -2.7483 -0.4227 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2574 -5.6053 -0.6344 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3496 -4.4010 -2.7846 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4670 -1.6346 -2.0283 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8508 1.6152 -1.0737 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1309 2.0879 -0.6227 C 0 0 0 0 0 0 0 0 0 0 0 0 8.8073 0.8180 0.2365 C 0 0 0 0 0 0 0 0 0 0 0 0 9.7920 -1.5184 0.2482 O 0 0 0 0 0 0 0 0 0 0 0 0 11.0375 -1.9194 -0.1634 C 0 0 0 0 0 0 0 0 0 0 0 0 13.2298 -2.1351 -1.2377 H 0 0 0 0 0 0 0 0 0 0 0 0 13.6525 -0.4467 -0.9006 H 0 0 0 0 0 0 0 0 0 0 0 0 13.2227 -0.8429 -2.5689 H 0 0 0 0 0 0 0 0 0 0 0 0 11.4523 0.1468 -0.7375 H 0 0 0 0 0 0 0 0 0 0 0 0 11.2013 -1.6028 -3.1553 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3867 -0.0553 -2.8320 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6372 -1.6180 -2.8748 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6023 -2.9193 -2.1290 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6482 0.4510 -1.8967 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7366 -0.9517 -1.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3927 -0.7758 1.1086 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2284 -1.8354 1.4328 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9506 -1.8999 -0.3884 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7596 0.4571 1.3728 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7227 -0.5664 -2.1989 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2298 1.0370 -2.7736 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8860 1.0175 -2.5289 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6022 2.0847 -1.2079 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0296 -0.8409 -0.8316 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6988 1.4272 1.1403 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9463 -0.5215 2.6246 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1127 -1.5673 1.4670 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1253 0.7189 3.1436 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2462 -0.7343 2.6184 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7442 1.9673 1.2983 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3104 -1.6298 -0.3080 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4323 -0.7569 -1.5942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3359 -1.3858 -0.3467 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4379 -1.6903 1.1552 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6367 0.8835 0.0021 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5328 2.2484 1.4434 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2713 1.0351 2.7112 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2913 1.0449 0.3842 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1864 -1.4060 1.8579 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5805 -0.7200 1.4348 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7271 1.3934 0.3852 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0032 3.1540 1.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8742 3.4058 3.9299 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4735 1.7708 4.3064 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3308 2.7353 4.2354 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.2878 2.0170 -0.3026 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.9152 0.2201 -0.0644 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9298 1.2139 1.0588 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7254 1.2177 -1.2229 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8949 3.8562 -1.6984 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5595 4.9962 0.2614 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.8900 4.6529 1.9753 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9931 3.1503 2.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.3862 3.0727 1.3211 H 0 0 0 0 0 0 0 0 0 0 0 0 -12.0084 2.9582 -1.5449 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3431 1.2033 -2.8274 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5290 -0.8865 3.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4675 -2.7210 0.7913 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8665 -3.1142 -0.7809 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0535 -3.3144 -2.9399 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6512 -5.4826 -2.0628 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1328 -4.4496 -0.6486 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9138 -4.5357 0.6211 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5889 -6.5183 -0.4791 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6163 -5.2269 -3.2462 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3057 -1.3961 -2.5200 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2047 1.1912 -1.8796 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2114 2.3234 -0.4668 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6016 2.2455 -1.5413 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5241 2.7334 -1.3266 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1912 2.3346 -0.9271 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8993 2.5210 0.3891 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5803 0.2845 0.8672 H 0 0 0 0 0 0 0 0 0 0 0 0 9.3780 1.7098 -0.1612 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0388 1.1435 0.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0708 -2.9006 -0.6670 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7094 -1.8964 0.7167 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 0 30 31 1 0 30 32 1 0 32 33 1 0 29 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 37 38 1 0 38 39 1 0 39 40 1 0 39 41 1 0 38 42 1 0 37 43 1 0 28 44 1 0 27 45 1 0 45 46 1 0 46 47 1 0 47 48 1 0 48 49 1 0 49 50 1 0 50 51 1 0 49 52 1 0 48 53 1 0 47 54 1 0 20 55 1 0 12 56 1 0 6 57 1 0 5 58 1 0 58 59 1 0 59 2 1 0 9 5 1 0 12 7 1 0 16 11 1 0 20 15 1 0 24 19 1 0 31 26 1 0 40 35 1 0 51 46 1 0 1 60 1 0 1 61 1 0 1 62 1 0 2 63 1 0 3 64 1 0 3 65 1 0 4 66 1 0 4 67 1 0 6 68 1 0 7 69 1 0 8 70 1 0 10 71 1 0 10 72 1 0 11 73 1 0 13 74 1 0 13 75 1 0 14 76 1 0 14 77 1 0 15 78 1 0 16 79 1 0 17 80 1 0 17 81 1 0 18 82 1 0 18 83 1 0 19 84 1 0 21 85 1 0 21 86 1 0 22 87 1 0 22 88 1 0 23 89 1 0 24 90 1 0 24 91 1 0 26 92 1 0 27 93 1 0 28 94 1 0 29 95 1 0 30 96 1 0 32 97 1 0 32 98 1 0 33 99 1 0 35100 1 0 36101 1 0 36102 1 0 37103 1 0 38104 1 0 39105 1 0 41106 1 0 41107 1 0 41108 1 0 42109 1 0 43110 1 0 44111 1 0 46112 1 0 47113 1 0 48114 1 0 49115 1 0 50116 1 0 50117 1 0 52118 1 0 53119 1 0 54120 1 0 55121 1 0 55122 1 0 55123 1 0 56124 1 0 56125 1 0 56126 1 0 57127 1 0 57128 1 0 57129 1 0 59130 1 0 59131 1 0 M END

Standard InCHIKey	FRNFDPWFRZTRKH-AOXZOSFBSA-N
Standard InCHI	InChI=1S/C44H72O15/c1-20-8-13-44(53-18-20)21(2)33-30(59-44)15-27-25-7-6-23-14-24(9-11-42(23,4)26(25)10-12-43(27,33)5)55-41-39(58-40-36(50)35(49)29(47)19-52-40)37(51)38(31(17-45)56-41)57-32-16-28(46)34(48)22(3)54-32/h20-41,45-51H,6-19H2,1-5H3/t20-,21-,22-,23+,24-,25+,26-,27-,28-,29-,30-,31+,32-,33-,34-,35+,36-,37-,38+,39+,40+,41+,42-,43-,44+/m0/s1
SMILES	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8CC(C(C(O8)C)O)O)O)OC9C(C(C(CO9)O)O)O)C)C)C)OC1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	840.49	Volume:	824.425 ? Van der Waals volume.
Dense:	1.019	LogP:	2.35 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.031 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.516 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	48.0
TPSA:	215.45 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	7.0	Rings:	9.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.183	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	6.636	Fsp³:	1.0
MCE-18:	224.091 ? 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:	0.013	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.056 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.146 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.38	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.869	MDCK Permeability:	-4.993
Pgp-inhibitor:	0.0	Pgp-substrate:	0.136
PAMPA:	0.934 ? 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):	0.009
20% Bioavailability (F20%):	0.001	30% Bioavailability (F30%):	0.043
50% Bioavailability (F50%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.346	MRP1:	1.0
Plasma Protein Binding (PPB):	64.557%	Volume Distribution (VD):	-0.358
Fu:	27.469% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.38	BCRP inhibitor:	0.001
BSEP inhibitor:	0.906

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.999	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.271	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.643	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):

1.45

Half-life (T1/2):

4.135

ADMET: Toxicity

hERG Blockers:	0.184	hERG Blockers (10um):	0.762
Human Hepatotoxicity (H-HT):	0.539	Drug-induced Liver Injury (DILI):	0.325
AMES Toxicity:	0.361	Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.635	Skin Sensitization:	0.013
Carcinogencity:	0.087	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.025
Drug-induced Neurotoxicity:	0.38	Ototoxicity:	1.0
Hematotoxicity:	0.007	Drug-induced Nephrotoxicity:	0.01
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.115
A549 Cytotoxicity:	0.082	Hek293 Cytotoxicity:	0.868
BCF:	1.641 ? 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:	4.334 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.03 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.983 ? 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
NPO4755	Asparagus filicinus	Species	Asparagaceae	Eukaryota	Roots	n.a.	n.a.	PMID[17629328]
NPO4755	Asparagus filicinus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4755	Asparagus filicinus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4755	Asparagus filicinus	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4755	Asparagus filicinus	Species	Asparagaceae	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

Activity Type	# Activity
EC50	2

Activity Type	# Activity
Cell line	2

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
NPT81	Cell line	A549	Homo sapiens	EC50	=	2.3	ug.mL-1	PubChem BioAssay data set
NPT83	Cell line	MCF7	Homo sapiens	EC50	=	3.0	ug.mL-1	PMID[12699389]

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 NPC471464 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	27926
0.1-0.2	19323
0.2-0.3	2097
0.3-0.4	303
0.4-0.5	96
0.5-0.6	61
0.6-0.7	38
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
0.8261	Intermediate Similarity	NPC19400
0.8	Intermediate Similarity	NPC6295
0.7549	Intermediate Similarity	NPC128572
0.7474	Intermediate Similarity	NPC250393
0.7273	Intermediate Similarity	NPC485595
0.7264	Intermediate Similarity	NPC475333
0.7264	Intermediate Similarity	NPC224098
0.7264	Intermediate Similarity	NPC208383
0.7129	Intermediate Similarity	NPC160426
0.7103	Intermediate Similarity	NPC475625
0.7059	Intermediate Similarity	NPC475351
0.701	Intermediate Similarity	NPC477451
0.6822	Remote Similarity	NPC97700
0.6822	Remote Similarity	NPC30856
0.6804	Remote Similarity	NPC297348
0.6804	Remote Similarity	NPC249204
0.6804	Remote Similarity	NPC48339
0.6804	Remote Similarity	NPC141769
0.6804	Remote Similarity	NPC477547
0.68	Remote Similarity	NPC211354
0.6792	Remote Similarity	NPC274200
0.6733	Remote Similarity	NPC264101
0.6699	Remote Similarity	NPC195297
0.6696	Remote Similarity	NPC480556
0.6667	Remote Similarity	NPC107962
0.6633	Remote Similarity	NPC177834
0.6604	Remote Similarity	NPC470433
0.6604	Remote Similarity	NPC46190
0.6604	Remote Similarity	NPC171073
0.6577	Remote Similarity	NPC232037
0.6465	Remote Similarity	NPC325828
0.6449	Remote Similarity	NPC475643
0.6435	Remote Similarity	NPC232054
0.6422	Remote Similarity	NPC480555
0.6422	Remote Similarity	NPC150372
0.6404	Remote Similarity	NPC132080
0.6373	Remote Similarity	NPC206003
0.6373	Remote Similarity	NPC473610
0.625	Remote Similarity	NPC269297
0.625	Remote Similarity	NPC222202
0.6195	Remote Similarity	NPC116756
0.6182	Remote Similarity	NPC51172
0.6182	Remote Similarity	NPC49032
0.6154	Remote Similarity	NPC107188
0.6091	Remote Similarity	NPC248746
0.6087	Remote Similarity	NPC480554
0.6078	Remote Similarity	NPC234352
0.6018	Remote Similarity	NPC475319
0.6	Remote Similarity	NPC194207
0.6	Remote Similarity	NPC22779
0.5983	Remote Similarity	NPC480553
0.595	Remote Similarity	NPC224314
0.5909	Remote Similarity	NPC473601
0.5877	Remote Similarity	NPC115165
0.5847	Remote Similarity	NPC233433
0.5833	Remote Similarity	NPC470866
0.581	Remote Similarity	NPC222731
0.5789	Remote Similarity	NPC184617
0.5776	Remote Similarity	NPC32361
0.5763	Remote Similarity	NPC476112
0.5763	Remote Similarity	NPC307534
0.5752	Remote Similarity	NPC42171
0.5725	Remote Similarity	NPC329807
0.5664	Remote Similarity	NPC92890
0.5656	Remote Similarity	NPC94086
0.5656	Remote Similarity	NPC473817
0.5631	Remote Similarity	NPC485594
0.5625	Remote Similarity	NPC202898
0.5619	Remote Similarity	NPC294686
0.5597	Remote Similarity	NPC481189
0.5596	Remote Similarity	NPC215408
0.5586	Remote Similarity	NPC113044
0.5586	Remote Similarity	NPC283829
0.5586	Remote Similarity	NPC161676
0.5556	Remote Similarity	NPC329727
0.5545	Remote Similarity	NPC125324
0.552	Remote Similarity	NPC220836
0.549	Remote Similarity	NPC481418
0.5417	Remote Similarity	NPC470864
0.5405	Remote Similarity	NPC470432
0.5405	Remote Similarity	NPC230507
0.5378	Remote Similarity	NPC473518
0.5372	Remote Similarity	NPC83137
0.5333	Remote Similarity	NPC232611
0.5304	Remote Similarity	NPC602423
0.5289	Remote Similarity	NPC108072
0.5289	Remote Similarity	NPC249265
0.5276	Remote Similarity	NPC477808
0.5259	Remote Similarity	NPC477809
0.5254	Remote Similarity	NPC294129
0.525	Remote Similarity	NPC13193
0.5221	Remote Similarity	NPC141433
0.5221	Remote Similarity	NPC70204
0.5214	Remote Similarity	NPC300557
0.5196	Remote Similarity	NPC88962
0.5192	Remote Similarity	NPC473774
0.5192	Remote Similarity	NPC481419
0.5192	Remote Similarity	NPC481417
0.5182	Remote Similarity	NPC329820
0.5169	Remote Similarity	NPC151134
0.5161	Remote Similarity	NPC31896
0.5135	Remote Similarity	NPC306131
0.5135	Remote Similarity	NPC200802
0.5126	Remote Similarity	NPC98018
0.5126	Remote Similarity	NPC284104
0.5126	Remote Similarity	NPC103616
0.5048	Remote Similarity	NPC481420
0.5048	Remote Similarity	NPC481421
0.5046	Remote Similarity	NPC291203
0.5046	Remote Similarity	NPC217205
0.5043	Remote Similarity	NPC14704

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC471464 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7894
0.1-0.2	1205
0.2-0.3	36
0.3-0.4	10
0.4-0.5	3
0.5-0.6	1
0.6-0.7	1
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
0.6465	Remote Similarity	NPD8171	Phase 2
0.5545	Remote Similarity	NPD8170	Phase 2

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