NPASS Compound

Natural Product: NPC521775

Natural Product ID	NPC521775
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	5-hydroxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-[4-[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
IUPAC Name	5-hydroxy-7-[(2~{S},3~{R},4~{S},5~{S},6~{S})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-[4-[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxyphenyl]-3-[(2~{S},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-[[(2~{R},3~{R},4~{S},5~{S},6~{R})-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

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 115121 0 0 0 0 0 0 0 0999 V2000 -0.1687 -3.0918 -1.8802 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9227 -2.1678 -1.4813 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4069 -0.8887 -1.2830 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9054 -0.7093 -1.5101 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9678 -0.7283 -0.5353 C 0 0 2 0 0 0 0 0 0 0 0 0 3.0270 -0.0703 -1.0518 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2095 -0.0500 -0.3990 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3223 -0.7445 -1.1974 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4577 -0.7057 -0.4372 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5395 -1.3555 -1.0736 C 0 0 2 0 0 0 0 0 0 0 0 0 7.7288 -2.5061 -0.3026 O 0 0 0 0 0 0 0 0 0 0 0 0 8.8618 -3.2102 -0.6926 C 0 0 2 0 0 0 0 0 0 0 0 0 8.8900 -4.4689 0.1594 C 0 0 0 0 0 0 0 0 0 0 0 0 8.9535 -4.1826 1.5061 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0464 -2.3608 -0.2871 C 0 0 1 0 0 0 0 0 0 0 0 0 11.2267 -3.0878 -0.3945 O 0 0 0 0 0 0 0 0 0 0 0 0 10.0556 -1.1362 -1.1435 C 0 0 2 0 0 0 0 0 0 0 0 0 10.9632 -0.2393 -0.5396 O 0 0 0 0 0 0 0 0 0 0 0 0 8.7203 -0.4615 -1.1590 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6657 0.2857 -2.3595 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1499 -0.7310 0.9574 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5103 0.0553 1.9116 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5225 -2.0994 0.8040 C 0 0 2 0 0 0 0 0 0 0 0 0 4.4770 -3.0751 0.4711 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3155 -2.1217 -0.0854 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2218 -2.6792 0.6375 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2801 0.0805 -0.8593 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9287 1.4692 -0.6039 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7962 2.2909 0.1261 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5222 3.6227 0.3470 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3870 4.2272 -0.1314 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0676 5.5494 0.0624 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8401 6.4387 0.7682 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1958 7.5395 -0.0362 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2551 8.2366 0.5215 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4411 9.5038 -0.2908 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2569 10.2534 -0.2240 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.1013 8.6039 1.9448 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3642 8.4334 2.5608 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1136 7.8386 2.7352 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.4632 8.6787 3.6673 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0763 7.0887 1.9337 C 0 0 1 0 0 0 0 0 0 0 0 0 0.5325 6.1671 2.7485 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4752 3.4405 -0.8492 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2016 2.0827 -1.0791 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5661 -0.2137 -0.6452 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0923 -1.3857 -0.8112 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4264 -1.6577 -0.5790 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9870 -2.9230 -0.7592 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3072 -3.1668 -0.5197 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.0173 -4.3547 -0.6667 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1825 -4.1395 -1.4040 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.1965 -3.5743 -0.6605 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.2573 -3.0239 -1.5937 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.3135 -2.4312 -0.9035 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8264 -4.6567 0.1884 C 0 0 1 0 0 0 0 0 0 0 0 0 -10.6272 -5.4577 -0.6581 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.7308 -5.5405 0.7141 C 0 0 2 0 0 0 0 0 0 0 0 0 -9.0320 -5.8411 2.0535 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.3774 -4.8499 0.7302 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4368 -5.7896 1.1278 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1438 -3.9218 -1.1892 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7921 -3.6553 -1.4267 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9260 -4.6520 -1.8616 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2675 -2.3986 -1.2397 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4712 -0.2047 0.3508 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5411 0.9907 -0.2306 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4362 -0.2620 -2.1929 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0225 -1.7922 -1.3943 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1779 -1.7248 -2.0702 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9046 -3.4499 -1.7597 H 0 0 0 0 0 0 0 0 0 0 0 0 9.7186 -5.1335 -0.0998 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9549 -5.0234 -0.0887 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2552 -3.5139 1.7796 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9130 -2.0432 0.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7385 -3.0208 0.4425 H 0 0 0 0 0 0 0 0 0 0 0 0 10.3780 -1.3707 -2.1831 H 0 0 0 0 0 0 0 0 0 0 0 0 11.5425 0.2053 -1.2091 H 0 0 0 0 0 0 0 0 0 0 0 0 8.6620 0.2416 -0.2909 H 0 0 0 0 0 0 0 0 0 0 0 0 7.9401 0.9362 -2.3579 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1914 -0.8793 1.2949 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2805 0.9196 1.4442 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1837 -2.3838 1.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8825 -3.5027 1.2717 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5486 -2.7298 -0.9773 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6273 -1.9638 0.9618 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7127 1.8269 0.5212 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2675 4.1638 0.9268 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7599 6.0411 1.2337 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1809 7.6260 0.3286 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2709 10.1212 0.0818 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5650 9.2474 -1.3816 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5156 9.7900 -0.7027 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8883 9.7025 2.0908 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2815 8.1467 3.4980 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6326 7.0540 3.3623 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4085 8.2661 4.5516 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6012 7.8252 1.4633 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3249 5.2266 2.5563 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3870 3.8600 -1.2525 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9018 1.5241 -1.6799 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0722 -0.8782 -0.2461 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3833 -5.1087 -1.1648 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8753 -2.7342 -0.0096 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.6968 -3.8694 -2.1791 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8420 -2.3280 -2.3400 H 0 0 0 0 0 0 0 0 0 0 0 0 -11.2044 -2.4294 0.0665 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.4489 -4.2215 0.9975 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.0515 -5.7340 -1.4384 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6691 -6.5081 0.1378 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3124 -6.4642 2.3717 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3921 -4.0343 1.4549 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2742 -5.8076 2.0997 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4341 -4.9450 -1.3707 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2993 -5.0350 -1.1545 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 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 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 15 17 1 0 17 18 1 0 17 19 1 0 19 20 1 0 7 21 1 0 21 22 1 0 21 23 1 0 23 24 1 0 23 25 1 0 25 26 1 0 3 27 2 0 27 28 1 0 28 29 2 0 29 30 1 0 30 31 2 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 35 36 1 0 36 37 1 0 35 38 1 0 38 39 1 0 38 40 1 0 40 41 1 0 40 42 1 0 42 43 1 0 31 44 1 0 44 45 2 0 27 46 1 0 46 47 1 0 47 48 2 0 48 49 1 0 49 50 1 0 50 51 1 0 51 52 1 0 52 53 1 0 53 54 1 0 54 55 1 0 53 56 1 0 56 57 1 0 56 58 1 0 58 59 1 0 58 60 1 0 60 61 1 0 49 62 2 0 62 63 1 0 63 64 1 0 63 65 2 0 65 2 1 0 25 5 1 0 45 28 1 0 65 47 1 0 19 10 1 0 42 33 1 0 60 51 1 0 5 66 1 1 7 67 1 1 8 68 1 0 8 69 1 0 10 70 1 6 12 71 1 6 13 72 1 0 13 73 1 0 14 74 1 0 15 75 1 1 16 76 1 0 17 77 1 6 18 78 1 0 19 79 1 1 20 80 1 0 21 81 1 1 22 82 1 0 23 83 1 1 24 84 1 0 25 85 1 6 26 86 1 0 29 87 1 0 30 88 1 0 33 89 1 1 35 90 1 1 36 91 1 0 36 92 1 0 37 93 1 0 38 94 1 6 39 95 1 0 40 96 1 1 41 97 1 0 42 98 1 6 43 99 1 0 44100 1 0 45101 1 0 48102 1 0 51103 1 6 53104 1 1 54105 1 0 54106 1 0 55107 1 0 56108 1 1 57109 1 0 58110 1 6 59111 1 0 60112 1 1 61113 1 0 62114 1 0 64115 1 0 M END

Standard InCHIKey	BFSYDSGBPJMJPN-XELWBUQRSA-N
Standard InCHI	InChI=1S/C39H50O26/c40-7-16-21(44)26(49)30(53)36(61-16)57-10-19-24(47)29(52)33(56)39(64-19)65-35-25(48)20-14(43)5-13(59-38-32(55)28(51)23(46)18(9-42)63-38)6-15(20)60-34(35)11-1-3-12(4-2-11)58-37-31(54)27(50)22(45)17(8-41)62-37/h1-6,16-19,21-24,26-33,36-47,49-56H,7-10H2/t16-,17-,18+,19-,21-,22-,23-,24-,26+,27+,28+,29+,30-,31-,32-,33-,36-,37-,38-,39+/m1/s1
SMILES	O=C1C(O[C@@H]2O[C@H](CO[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)=C(C2=CC=C(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C2)OC2=CC(O[C@@H]3O[C@@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=CC(O)=C12

Calculated Properties

Physi-Chem Properties

Molecular Weight:	934.26	Volume:	830.659 ? Van der Waals volume.
Dense:	1.125	LogP:	-1.204 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.079 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.842 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	13.0	Rigid Bonds:	42.0
TPSA:	427.73 ? Topological Polar Surface Area.	H-Bond Acceptor:	26.0
H-Bond Donor:	16.0	Rings:	7.0
Heavy Atoms:	26.0

MedChem Properties

QED Drug-Likeness Score:	0.076	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.805	Fsp³:	0.615
MCE-18:	181.746 ? 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:	0.638	Fluc inhibitor:	0.291 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.658 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.63 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.322	Promiscuous compounds:	0.536

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-7.553	MDCK Permeability:	-4.511
Pgp-inhibitor:	0.0	Pgp-substrate:	0.832
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):	0.999
20% Bioavailability (F20%):	0.011	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.001
Plasma Protein Binding (PPB):	65.08%	Volume Distribution (VD):	-0.245
Fu:	28.858% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.008
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.001
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):

-0.014

Half-life (T1/2):

6.836

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.002
Human Hepatotoxicity (H-HT):	0.865	Drug-induced Liver Injury (DILI):	0.999
AMES Toxicity:	0.997	Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.0	Skin Sensitization:	1.0
Carcinogencity:	0.005	Eye Corrosion:	0.0
Eye Irritation:	0.0	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	1.0
Hematotoxicity:	0.225	Drug-induced Nephrotoxicity:	0.988
Genotoxicity:	0.786	RPMI-8226 Immunitoxicity:	0.255
A549 Cytotoxicity:	0.492	Hek293 Cytotoxicity:	0.105
BCF:	0.311 ? 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:	2.773 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.711 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.4 ? 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
NPO11235	Asplenium nidus	Species	Aspleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11235	Asplenium nidus	Species	Aspleniaceae	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 NPC521775 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	21874
0.1-0.2	23615
0.2-0.3	3176
0.3-0.4	632
0.4-0.5	317
0.5-0.6	131
0.6-0.7	62
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8421	Intermediate Similarity	NPC289667
0.7586	Intermediate Similarity	NPC186816
0.7407	Intermediate Similarity	NPC297987
0.7368	Intermediate Similarity	NPC25523
0.7292	Intermediate Similarity	NPC277532
0.7195	Intermediate Similarity	NPC136042
0.7188	Intermediate Similarity	NPC480441
0.6977	Remote Similarity	NPC116458
0.6977	Remote Similarity	NPC246943
0.6966	Remote Similarity	NPC275454
0.6932	Remote Similarity	NPC251417
0.6889	Remote Similarity	NPC156869
0.6786	Remote Similarity	NPC64305
0.6782	Remote Similarity	NPC605784
0.6739	Remote Similarity	NPC64425
0.6706	Remote Similarity	NPC84362
0.6559	Remote Similarity	NPC488073
0.6522	Remote Similarity	NPC22062
0.6522	Remote Similarity	NPC473634
0.6522	Remote Similarity	NPC138811
0.6495	Remote Similarity	NPC135358
0.6437	Remote Similarity	NPC472459
0.6429	Remote Similarity	NPC14187
0.6421	Remote Similarity	NPC35119
0.6373	Remote Similarity	NPC470716
0.6344	Remote Similarity	NPC479405
0.6337	Remote Similarity	NPC470715
0.6289	Remote Similarity	NPC76831
0.6279	Remote Similarity	NPC249281
0.6277	Remote Similarity	NPC479404
0.625	Remote Similarity	NPC32641
0.625	Remote Similarity	NPC256188
0.625	Remote Similarity	NPC209296
0.6237	Remote Similarity	NPC173582
0.6237	Remote Similarity	NPC265885
0.6237	Remote Similarity	NPC181465
0.6237	Remote Similarity	NPC215710
0.6237	Remote Similarity	NPC67105
0.6237	Remote Similarity	NPC473438
0.6237	Remote Similarity	NPC253788
0.6207	Remote Similarity	NPC95090
0.6207	Remote Similarity	NPC27408
0.62	Remote Similarity	NPC121703
0.6186	Remote Similarity	NPC142142
0.618	Remote Similarity	NPC285197
0.618	Remote Similarity	NPC611303
0.617	Remote Similarity	NPC210073
0.6154	Remote Similarity	NPC276377
0.6146	Remote Similarity	NPC479403
0.6139	Remote Similarity	NPC189564
0.6136	Remote Similarity	NPC46420
0.6129	Remote Similarity	NPC471079
0.6095	Remote Similarity	NPC295625
0.6082	Remote Similarity	NPC473623
0.6082	Remote Similarity	NPC473327
0.6064	Remote Similarity	NPC44931
0.6064	Remote Similarity	NPC227508
0.6023	Remote Similarity	NPC277205
0.6023	Remote Similarity	NPC37919
0.602	Remote Similarity	NPC488089
0.602	Remote Similarity	NPC486577
0.6019	Remote Similarity	NPC164704
0.6	Remote Similarity	NPC203259
0.6	Remote Similarity	NPC33054
0.6	Remote Similarity	NPC176740
0.6	Remote Similarity	NPC471725
0.6	Remote Similarity	NPC134532
0.6	Remote Similarity	NPC150164
0.6	Remote Similarity	NPC602582
0.5979	Remote Similarity	NPC470443
0.5955	Remote Similarity	NPC24043
0.5955	Remote Similarity	NPC271692
0.5934	Remote Similarity	NPC22832
0.5934	Remote Similarity	NPC486578
0.5922	Remote Similarity	NPC292019
0.5922	Remote Similarity	NPC202908
0.5909	Remote Similarity	NPC77672
0.5909	Remote Similarity	NPC133671
0.5909	Remote Similarity	NPC135391
0.5909	Remote Similarity	NPC78263
0.5909	Remote Similarity	NPC250069
0.5895	Remote Similarity	NPC67326
0.5895	Remote Similarity	NPC39834
0.5876	Remote Similarity	NPC240306
0.5843	Remote Similarity	NPC158674
0.5843	Remote Similarity	NPC323593
0.5843	Remote Similarity	NPC203500
0.5843	Remote Similarity	NPC189142
0.5843	Remote Similarity	NPC77660
0.5833	Remote Similarity	NPC65563
0.5833	Remote Similarity	NPC470949
0.5824	Remote Similarity	NPC60735
0.5824	Remote Similarity	NPC26230
0.5824	Remote Similarity	NPC488071
0.5816	Remote Similarity	NPC65711
0.58	Remote Similarity	NPC473073
0.578	Remote Similarity	NPC470720
0.5773	Remote Similarity	NPC473571
0.5773	Remote Similarity	NPC110941
0.5761	Remote Similarity	NPC243930
0.5761	Remote Similarity	NPC120099
0.5761	Remote Similarity	NPC21666
0.5758	Remote Similarity	NPC72016
0.5743	Remote Similarity	NPC292929
0.573	Remote Similarity	NPC261866
0.573	Remote Similarity	NPC39360
0.573	Remote Similarity	NPC29763
0.573	Remote Similarity	NPC210003
0.5728	Remote Similarity	NPC203145
0.5714	Remote Similarity	NPC46202
0.5714	Remote Similarity	NPC126784
0.5714	Remote Similarity	NPC241423
0.5699	Remote Similarity	NPC607707
0.5688	Remote Similarity	NPC470717
0.5686	Remote Similarity	NPC602448
0.5667	Remote Similarity	NPC145038
0.5667	Remote Similarity	NPC56077
0.5667	Remote Similarity	NPC281131
0.5667	Remote Similarity	NPC253662
0.5667	Remote Similarity	NPC179950
0.5667	Remote Similarity	NPC88789
0.5667	Remote Similarity	NPC491374
0.566	Remote Similarity	NPC311850
0.5644	Remote Similarity	NPC476472
0.5644	Remote Similarity	NPC294815
0.5644	Remote Similarity	NPC16194
0.5625	Remote Similarity	NPC187379
0.5612	Remote Similarity	NPC204693
0.5607	Remote Similarity	NPC488083
0.5604	Remote Similarity	NPC73511
0.56	Remote Similarity	NPC606657
0.5591	Remote Similarity	NPC148710
0.5588	Remote Similarity	NPC287889
0.5579	Remote Similarity	NPC116864
0.5579	Remote Similarity	NPC244776
0.5556	Remote Similarity	NPC19388
0.5556	Remote Similarity	NPC240431
0.5556	Remote Similarity	NPC55786
0.5556	Remote Similarity	NPC488074
0.5545	Remote Similarity	NPC470719
0.551	Remote Similarity	NPC102028
0.551	Remote Similarity	NPC303913
0.5505	Remote Similarity	NPC68592
0.5495	Remote Similarity	NPC234739
0.5495	Remote Similarity	NPC488078
0.5484	Remote Similarity	NPC307938
0.5481	Remote Similarity	NPC244875
0.5474	Remote Similarity	NPC488072
0.5455	Remote Similarity	NPC198199
0.5446	Remote Similarity	NPC229409
0.5437	Remote Similarity	NPC101636
0.5437	Remote Similarity	NPC470449
0.5435	Remote Similarity	NPC488080
0.5435	Remote Similarity	NPC169977
0.5426	Remote Similarity	NPC601144
0.5426	Remote Similarity	NPC609478
0.54	Remote Similarity	NPC64051
0.5398	Remote Similarity	NPC192539
0.5392	Remote Similarity	NPC5319
0.5385	Remote Similarity	NPC470446
0.5385	Remote Similarity	NPC58053
0.5376	Remote Similarity	NPC42773
0.5376	Remote Similarity	NPC45522
0.5376	Remote Similarity	NPC325555
0.5376	Remote Similarity	NPC226304
0.5368	Remote Similarity	NPC311830
0.5357	Remote Similarity	NPC488079
0.5351	Remote Similarity	NPC262222
0.5339	Remote Similarity	NPC223860
0.5327	Remote Similarity	NPC48984
0.5326	Remote Similarity	NPC8573
0.5315	Remote Similarity	NPC298666
0.5312	Remote Similarity	NPC203050
0.5312	Remote Similarity	NPC225434
0.5312	Remote Similarity	NPC601586
0.531	Remote Similarity	NPC120952
0.531	Remote Similarity	NPC209550
0.5306	Remote Similarity	NPC139320
0.5306	Remote Similarity	NPC609888
0.53	Remote Similarity	NPC129264
0.5294	Remote Similarity	NPC483707
0.5283	Remote Similarity	NPC11468
0.5278	Remote Similarity	NPC470712
0.5269	Remote Similarity	NPC186807
0.5269	Remote Similarity	NPC181712
0.5269	Remote Similarity	NPC603655
0.5253	Remote Similarity	NPC470405
0.5248	Remote Similarity	NPC153755
0.5244	Remote Similarity	NPC57751
0.5222	Remote Similarity	NPC288084
0.5217	Remote Similarity	NPC143851
0.5213	Remote Similarity	NPC599850
0.5204	Remote Similarity	NPC8856
0.5204	Remote Similarity	NPC473682
0.5196	Remote Similarity	NPC12013
0.5196	Remote Similarity	NPC11432
0.5196	Remote Similarity	NPC477613
0.5192	Remote Similarity	NPC470447
0.5192	Remote Similarity	NPC85751
0.5192	Remote Similarity	NPC475382

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC521775 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5364
0.1-0.2	3705
0.2-0.3	67
0.3-0.4	7
0.4-0.5	1
0.5-0.6	1
0.6-0.7	3
0.7-0.8	1
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
0.7053	Intermediate Similarity	NPD7808	Phase 3
0.6989	Remote Similarity	NPD7251	Phase 2
0.625	Remote Similarity	NPD7054	Phase 4
0.6	Remote Similarity	NPD6797	Phase 2
0.5392	Remote Similarity	NPD7804	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