NPASS Compound

Natural Product: NPC535451

Natural Product ID	NPC535451
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Kaempferol 3-glucoside-(1->6)-glucoside-7-alpha-L-rhamnoside
IUPAC Name	5-hydroxy-2-(4-hydroxyphenyl)-7-[(2~{S},3~{R},4~{S},5~{R},6~{S})-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-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]

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 93 98 0 0 0 0 0 0 0 0999 V2000 9.1457 -1.1782 0.6425 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5300 0.2512 0.9282 C 0 0 2 0 0 0 0 0 0 0 0 0 8.4569 0.9896 1.3249 O 0 0 0 0 0 0 0 0 0 0 0 0 7.5613 1.3181 0.3262 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5031 2.1048 0.7984 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1578 1.8115 0.7657 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2702 2.7493 1.3034 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9090 2.5441 1.3158 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0256 3.4672 1.8464 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3632 1.3786 0.7850 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0073 1.1520 0.7909 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2134 1.9930 1.2700 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4923 -0.0418 0.2478 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8536 -0.2212 0.2922 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5620 -0.8139 1.3944 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2993 -1.8662 0.9717 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6456 -1.7286 0.9641 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.2067 -0.8581 -0.1574 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5797 -0.8547 0.0370 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.3133 -0.1339 -0.8604 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9229 0.9186 -0.1343 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7122 1.7020 -0.9720 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.1248 2.9196 -0.1759 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0251 3.6594 0.2547 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.9960 0.9704 -1.3508 C 0 0 1 0 0 0 0 0 0 0 0 0 -9.1997 1.1088 -2.7095 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.8122 -0.4653 -0.9754 C 0 0 2 0 0 0 0 0 0 0 0 0 -8.9225 -0.6499 0.4018 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.4520 -0.9155 -1.4712 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.4248 -0.7535 -2.8431 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2395 -1.3108 2.2635 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3573 -2.3732 3.1647 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5536 -0.1566 2.8627 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3509 1.0060 2.8747 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2650 0.1756 2.2494 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.3887 0.5223 3.3161 O 0 0 0 0 0 0 0 0 0 0 0 0 1.3840 -0.9183 -0.2676 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9764 -2.1754 -0.8641 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2612 -2.5200 -1.3171 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5178 -3.8068 -1.8213 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4627 -4.7661 -1.8803 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2245 -6.0522 -2.3794 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7193 -4.4332 -1.4277 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9441 -3.1845 -0.9439 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7108 -0.6475 -0.2465 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2155 0.4408 0.2499 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5943 0.6757 0.2511 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2169 1.9922 -0.8582 C 0 0 2 0 0 0 0 0 0 0 0 0 7.2819 2.1513 -1.9005 O 0 0 0 0 0 0 0 0 0 0 0 0 9.4649 1.3222 -1.3252 C 0 0 1 0 0 0 0 0 0 0 0 0 10.2277 2.2172 -2.1099 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3230 0.8854 -0.1911 C 0 0 1 0 0 0 0 0 0 0 0 0 11.0763 1.9294 0.3369 O 0 0 0 0 0 0 0 0 0 0 0 0 9.8284 -1.9139 1.1488 H 0 0 0 0 0 0 0 0 0 0 0 0 9.1677 -1.4232 -0.4262 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1376 -1.3908 1.1035 H 0 0 0 0 0 0 0 0 0 0 0 0 10.2374 0.2154 1.8088 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1584 0.3678 -0.0710 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6972 3.6493 1.7122 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2242 4.4475 1.9555 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7207 -1.2366 2.0292 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0752 -2.7532 0.7374 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8665 0.1971 0.0059 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8802 -1.1654 -1.1498 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6569 0.3341 -1.6165 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1685 2.0626 -1.8658 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.6857 2.6399 0.7483 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.7968 3.6000 -0.7385 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7020 3.3447 1.1434 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8836 1.3971 -0.8437 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.3059 2.0791 -2.8929 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5577 -1.1024 -1.4671 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.8828 -0.7731 0.6147 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3889 -1.9977 -1.2470 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9395 0.0373 -3.1256 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3167 -1.0319 2.0362 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9081 -3.0696 2.7122 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3755 -0.4206 3.9594 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0254 1.6327 2.1711 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3570 1.1297 1.6733 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3854 -0.2373 3.9436 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0291 -1.7788 -1.3117 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5006 -4.0555 -2.1707 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8481 -6.3718 -3.1125 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5359 -5.1680 -1.4551 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9323 -2.9492 -0.5956 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2235 -0.0889 -0.1776 H 0 0 0 0 0 0 0 0 0 0 0 0 8.4811 3.0224 -0.5334 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9465 1.2495 -2.0991 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2087 0.4897 -2.0280 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6856 2.5859 -2.8507 H 0 0 0 0 0 0 0 0 0 0 0 0 11.0364 0.1150 -0.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5884 2.8003 0.3343 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 2 0 7 8 1 0 8 9 1 0 8 10 2 0 10 11 1 0 11 12 2 0 11 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 22 25 1 0 25 26 1 0 25 27 1 0 27 28 1 0 27 29 1 0 29 30 1 0 17 31 1 0 31 32 1 0 31 33 1 0 33 34 1 0 33 35 1 0 35 36 1 0 13 37 2 0 37 38 1 0 38 39 2 0 39 40 1 0 40 41 2 0 41 42 1 0 41 43 1 0 43 44 2 0 37 45 1 0 45 46 1 0 46 47 2 0 4 48 1 0 48 49 1 0 48 50 1 0 50 51 1 0 50 52 1 0 52 53 1 0 52 2 1 0 47 6 1 0 46 10 1 0 35 15 1 0 44 38 1 0 29 20 1 0 1 54 1 0 1 55 1 0 1 56 1 0 2 57 1 1 4 58 1 6 7 59 1 0 9 60 1 0 15 61 1 1 17 62 1 6 18 63 1 0 18 64 1 0 20 65 1 6 22 66 1 6 23 67 1 0 23 68 1 0 24 69 1 0 25 70 1 1 26 71 1 0 27 72 1 6 28 73 1 0 29 74 1 6 30 75 1 0 31 76 1 6 32 77 1 0 33 78 1 1 34 79 1 0 35 80 1 6 36 81 1 0 39 82 1 0 40 83 1 0 42 84 1 0 43 85 1 0 44 86 1 0 47 87 1 0 48 88 1 1 49 89 1 0 50 90 1 6 51 91 1 0 52 92 1 6 53 93 1 0 M END

Standard InCHIKey	QFSDWLPMRWDFID-NBKJOUBXSA-N
Standard InCHI	InChI=1S/C33H40O20/c1-10-19(37)23(41)27(45)32(48-10)49-13-6-14(36)18-15(7-13)50-29(11-2-4-12(35)5-3-11)30(22(18)40)53-33-28(46)25(43)21(39)17(52-33)9-47-31-26(44)24(42)20(38)16(8-34)51-31/h2-7,10,16-17,19-21,23-28,31-39,41-46H,8-9H2,1H3/t10-,16+,17+,19-,20+,21+,23-,24-,25-,26+,27+,28+,31+,32-,33-/m0/s1
SMILES	C[C@@H]1O[C@@H](OC2=CC(O)=C3C(=O)C(O[C@@H]4O[C@H](CO[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@H]5O)[C@@H](O)[C@H](O)[C@H]4O)=C(C4=CC=C(O)C=C4)OC3=C2)[C@H](O)[C@@H](O)[C@H]1O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	756.21	Volume:	682.698 ? Van der Waals volume.
Dense:	1.108	LogP:	0.242 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.054 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.245 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	36.0
TPSA:	328.35 ? Topological Polar Surface Area.	H-Bond Acceptor:	20.0
H-Bond Donor:	12.0	Rings:	6.0
Heavy Atoms:	20.0

MedChem Properties

QED Drug-Likeness Score:	0.099	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.305	Fsp³:	0.545
MCE-18:	150.706 ? 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:	0.623	Fluc inhibitor:	0.27 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.699 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.578 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.183	Promiscuous compounds:	0.539

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.891	MDCK Permeability:	-4.844
Pgp-inhibitor:	0.0	Pgp-substrate:	0.863
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):	0.876
20% Bioavailability (F20%):	0.035	30% Bioavailability (F30%):	0.999
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.004
Plasma Protein Binding (PPB):	78.933%	Volume Distribution (VD):	-0.064
Fu:	18.91% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.239
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:	0.395
HLM stability:	0.004 ? 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):

0.919

Half-life (T1/2):

6.687

ADMET: Toxicity

hERG Blockers:	0.008	hERG Blockers (10um):	0.035
Human Hepatotoxicity (H-HT):	0.55	Drug-induced Liver Injury (DILI):	0.977
AMES Toxicity:	0.952	Rat Oral Acute Toxicity:	0.001
Maximum Recommended Daily Dose:	0.003	Skin Sensitization:	0.999
Carcinogencity:	0.01	Eye Corrosion:	0.0
Eye Irritation:	0.003	Respiratory Toxicity:	0.0
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.998
Hematotoxicity:	0.043	Drug-induced Nephrotoxicity:	0.623
Genotoxicity:	0.578	RPMI-8226 Immunitoxicity:	0.183
A549 Cytotoxicity:	0.541	Hek293 Cytotoxicity:	0.511
BCF:	0.392 ? 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:	2.865 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.538 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.507 ? 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
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO30517	Paris polyphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22663190]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO49356	Sauropus androgynus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36500671]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30517	Paris polyphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO49356	Sauropus androgynus	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30517	Paris polyphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO30517	Paris polyphylla	Species	Melanthiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	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 NPC535451 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	21758
0.1-0.2	23656
0.2-0.3	3359
0.3-0.4	541
0.4-0.5	244
0.5-0.6	99
0.6-0.7	76
0.7-0.8	2
0.8-0.85	3
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9268	High Similarity	NPC186816
0.8415	Intermediate Similarity	NPC116458
0.8415	Intermediate Similarity	NPC246943
0.828	Intermediate Similarity	NPC25523
0.7901	Intermediate Similarity	NPC249281
0.7805	Intermediate Similarity	NPC297987
0.7711	Intermediate Similarity	NPC46420
0.7692	Intermediate Similarity	NPC35119
0.7674	Intermediate Similarity	NPC276377
0.7558	Intermediate Similarity	NPC605784
0.7528	Intermediate Similarity	NPC173582
0.7528	Intermediate Similarity	NPC265885
0.7528	Intermediate Similarity	NPC181465
0.7528	Intermediate Similarity	NPC215710
0.7528	Intermediate Similarity	NPC473438
0.7528	Intermediate Similarity	NPC253788
0.7526	Intermediate Similarity	NPC480441
0.75	Intermediate Similarity	NPC32641
0.75	Intermediate Similarity	NPC256188
0.7444	Intermediate Similarity	NPC150164
0.7333	Intermediate Similarity	NPC44931
0.7234	Intermediate Similarity	NPC142142
0.7065	Intermediate Similarity	NPC65563
0.7065	Intermediate Similarity	NPC470949
0.7065	Intermediate Similarity	NPC156869
0.6989	Remote Similarity	NPC473571
0.6989	Remote Similarity	NPC110941
0.6977	Remote Similarity	NPC136042
0.697	Remote Similarity	NPC189564
0.6957	Remote Similarity	NPC67105
0.6947	Remote Similarity	NPC72016
0.6923	Remote Similarity	NPC251417
0.6915	Remote Similarity	NPC240306
0.6915	Remote Similarity	NPC64425
0.6897	Remote Similarity	NPC271692
0.6882	Remote Similarity	NPC203259
0.6882	Remote Similarity	NPC33054
0.6882	Remote Similarity	NPC210073
0.6882	Remote Similarity	NPC176740
0.6882	Remote Similarity	NPC471725
0.6882	Remote Similarity	NPC134532
0.6882	Remote Similarity	NPC602582
0.6869	Remote Similarity	NPC203145
0.686	Remote Similarity	NPC289667
0.6768	Remote Similarity	NPC14187
0.67	Remote Similarity	NPC121703
0.6667	Remote Similarity	NPC470443
0.6667	Remote Similarity	NPC471079
0.6667	Remote Similarity	NPC602448
0.6596	Remote Similarity	NPC275454
0.6562	Remote Similarity	NPC488073
0.6526	Remote Similarity	NPC479405
0.6517	Remote Similarity	NPC84362
0.6465	Remote Similarity	NPC476472
0.6465	Remote Similarity	NPC294815
0.6465	Remote Similarity	NPC473073
0.6465	Remote Similarity	NPC16194
0.6458	Remote Similarity	NPC479404
0.6442	Remote Similarity	NPC277532
0.6421	Remote Similarity	NPC39834
0.6421	Remote Similarity	NPC227508
0.6408	Remote Similarity	NPC292019
0.6408	Remote Similarity	NPC202908
0.6404	Remote Similarity	NPC158674
0.6392	Remote Similarity	NPC126784
0.6392	Remote Similarity	NPC241423
0.6374	Remote Similarity	NPC611303
0.6364	Remote Similarity	NPC111929
0.6364	Remote Similarity	NPC320283
0.6364	Remote Similarity	NPC41121
0.6354	Remote Similarity	NPC22062
0.6354	Remote Similarity	NPC473634
0.6354	Remote Similarity	NPC303913
0.6354	Remote Similarity	NPC138811
0.6292	Remote Similarity	NPC77672
0.6292	Remote Similarity	NPC108831
0.6292	Remote Similarity	NPC133671
0.6292	Remote Similarity	NPC135391
0.6292	Remote Similarity	NPC78263
0.6292	Remote Similarity	NPC250069
0.6292	Remote Similarity	NPC182634
0.6263	Remote Similarity	NPC209296
0.6263	Remote Similarity	NPC473327
0.6222	Remote Similarity	NPC323593
0.6222	Remote Similarity	NPC203500
0.618	Remote Similarity	NPC331652
0.6162	Remote Similarity	NPC12013
0.6162	Remote Similarity	NPC479403
0.6162	Remote Similarity	NPC11432
0.6162	Remote Similarity	NPC477613
0.6154	Remote Similarity	NPC24043
0.6111	Remote Similarity	NPC39360
0.6111	Remote Similarity	NPC29763
0.6111	Remote Similarity	NPC210003
0.6082	Remote Similarity	NPC67326
0.6078	Remote Similarity	NPC292929
0.6078	Remote Similarity	NPC101636
0.6055	Remote Similarity	NPC298666
0.6038	Remote Similarity	NPC164704
0.6036	Remote Similarity	NPC209550
0.6019	Remote Similarity	NPC135358
0.5979	Remote Similarity	NPC139320
0.5934	Remote Similarity	NPC238376
0.5922	Remote Similarity	NPC470449
0.5922	Remote Similarity	NPC221342
0.5922	Remote Similarity	NPC476470
0.5893	Remote Similarity	NPC138990
0.5882	Remote Similarity	NPC486577
0.587	Remote Similarity	NPC277205
0.587	Remote Similarity	NPC37919
0.5842	Remote Similarity	NPC65711
0.5841	Remote Similarity	NPC192539
0.5825	Remote Similarity	NPC470447
0.5816	Remote Similarity	NPC480466
0.5806	Remote Similarity	NPC488080
0.5806	Remote Similarity	NPC169977
0.5804	Remote Similarity	NPC470720
0.5784	Remote Similarity	NPC606657
0.578	Remote Similarity	NPC470716
0.5773	Remote Similarity	NPC116864
0.5773	Remote Similarity	NPC244776
0.5769	Remote Similarity	NPC298171
0.5761	Remote Similarity	NPC127546
0.5761	Remote Similarity	NPC57625
0.5761	Remote Similarity	NPC19709
0.5761	Remote Similarity	NPC173637
0.5761	Remote Similarity	NPC317489
0.5761	Remote Similarity	NPC223424
0.5761	Remote Similarity	NPC600591
0.5758	Remote Similarity	NPC163242
0.5758	Remote Similarity	NPC272068
0.5743	Remote Similarity	NPC488074
0.5743	Remote Similarity	NPC64051
0.5741	Remote Similarity	NPC470715
0.5714	Remote Similarity	NPC470717
0.5702	Remote Similarity	NPC175429
0.57	Remote Similarity	NPC65003
0.5699	Remote Similarity	NPC145038
0.5699	Remote Similarity	NPC8573
0.5699	Remote Similarity	NPC56077
0.5699	Remote Similarity	NPC281131
0.5699	Remote Similarity	NPC64305
0.5699	Remote Similarity	NPC253662
0.5699	Remote Similarity	NPC179950
0.5699	Remote Similarity	NPC88789
0.5699	Remote Similarity	NPC189142
0.5699	Remote Similarity	NPC77660
0.5699	Remote Similarity	NPC491374
0.5644	Remote Similarity	NPC129264
0.5638	Remote Similarity	NPC27640
0.5631	Remote Similarity	NPC122467
0.5604	Remote Similarity	NPC288084
0.56	Remote Similarity	NPC470405
0.5588	Remote Similarity	NPC470125
0.5579	Remote Similarity	NPC472459
0.5545	Remote Similarity	NPC311850
0.5524	Remote Similarity	NPC85751
0.5524	Remote Similarity	NPC19240
0.5524	Remote Similarity	NPC89127
0.5521	Remote Similarity	NPC307938
0.5521	Remote Similarity	NPC488071
0.5514	Remote Similarity	NPC470455
0.551	Remote Similarity	NPC170052
0.551	Remote Similarity	NPC135846
0.55	Remote Similarity	NPC187379
0.5487	Remote Similarity	NPC198199
0.5481	Remote Similarity	NPC473623
0.5481	Remote Similarity	NPC270448
0.5462	Remote Similarity	NPC483159
0.5462	Remote Similarity	NPC483160
0.5446	Remote Similarity	NPC471748
0.5437	Remote Similarity	NPC153755
0.5429	Remote Similarity	NPC270675
0.5429	Remote Similarity	NPC488089
0.5429	Remote Similarity	NPC195685
0.5426	Remote Similarity	NPC261866
0.5421	Remote Similarity	NPC470446
0.5417	Remote Similarity	NPC59534
0.5417	Remote Similarity	NPC599850
0.5408	Remote Similarity	NPC223747
0.54	Remote Similarity	NPC473682
0.54	Remote Similarity	NPC480463
0.5398	Remote Similarity	NPC68592
0.5392	Remote Similarity	NPC304741
0.5392	Remote Similarity	NPC605592
0.5377	Remote Similarity	NPC80068
0.5377	Remote Similarity	NPC76831
0.537	Remote Similarity	NPC214621
0.537	Remote Similarity	NPC34267
0.5361	Remote Similarity	NPC285197
0.5354	Remote Similarity	NPC203050
0.5354	Remote Similarity	NPC225434
0.5354	Remote Similarity	NPC476215
0.5354	Remote Similarity	NPC66087
0.5347	Remote Similarity	NPC29958
0.5345	Remote Similarity	NPC120952
0.534	Remote Similarity	NPC204693
0.534	Remote Similarity	NPC115674
0.534	Remote Similarity	NPC470444
0.5333	Remote Similarity	NPC229409

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC535451 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5642
0.1-0.2	3434
0.2-0.3	63
0.3-0.4	4
0.4-0.5	1
0.5-0.6	2
0.6-0.7	2
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7717	Intermediate Similarity	NPD7251	Phase 2
0.7041	Intermediate Similarity	NPD7808	Phase 3
0.6882	Remote Similarity	NPD6797	Phase 2
0.6263	Remote Similarity	NPD7054	Phase 4
0.5283	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.5045	Remote Similarity	NPD7472	Pre-clinical

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