NPASS Compound

Natural Product: NPC323526

Natural Product ID	NPC323526
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	FIAAVMJLAGNUKW-DAMJSERUSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	69542256
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-glycosides [CHEMONTID:0003535] Flavonoid 8-C-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 72 76 0 0 0 0 0 0 0 0999 V2000 4.7711 -2.2053 -0.9966 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1065 -2.4949 -1.1667 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5226 -3.7944 -1.3595 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5674 -4.7795 -1.3757 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2108 -4.4774 -1.2019 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7858 -3.1902 -1.0097 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3938 -2.7822 -0.8204 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3856 -3.7231 -0.8261 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0841 -3.3297 -0.6478 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8922 -4.1099 -0.6382 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1450 -1.9699 -0.4674 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4451 -1.5153 -0.2821 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6457 -0.1810 -0.1078 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5762 0.6961 -0.1160 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7231 0.2939 -0.2945 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8899 -1.0887 -0.4713 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0908 -1.5074 -0.6423 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8592 1.2220 -0.2864 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7397 1.2548 0.8738 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2979 2.2749 1.8861 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4271 3.6195 1.1973 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0434 3.5504 -0.2562 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3576 2.4517 -0.6306 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1433 4.7668 -0.4995 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7960 4.8659 -1.8430 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8148 4.6367 1.8896 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0427 2.0459 2.4175 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0136 1.7096 0.4314 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8805 2.0335 0.0664 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0366 0.2972 0.0889 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3770 0.2946 1.5570 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8198 0.4638 1.8474 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7053 0.6288 0.6683 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1473 0.2033 -0.6329 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9706 -0.5312 -0.5392 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1544 -0.6494 -1.4051 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.3701 0.0275 -1.5403 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9487 -0.0161 0.8660 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.2835 -0.6508 2.5774 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8933 -0.8971 2.1387 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4782 -2.4566 -0.2850 O 0 0 0 0 0 0 0 0 0 0 0 0 7.8813 -4.0624 -1.5295 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4515 -1.1776 -0.8451 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8808 -1.7261 -1.1571 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8745 -5.7979 -1.5248 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4687 -5.2676 -1.2174 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5575 -4.7838 -0.9660 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4959 0.9074 -1.1772 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9860 0.2781 1.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0645 2.2449 2.7333 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5350 3.8492 1.2127 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9035 3.6973 -0.9452 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2287 4.7270 0.1272 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6691 5.7060 -0.2106 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5875 5.7737 -2.1219 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7118 4.4874 2.8411 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1392 1.3712 3.1348 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1003 1.5924 -0.5461 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3299 2.6057 -0.6303 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1925 1.3301 -0.2845 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7500 1.1063 2.0248 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9268 1.3271 2.5676 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9706 1.7192 0.5970 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9266 1.0683 -1.2965 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7591 -0.9838 -2.3674 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3432 -1.5498 -0.7841 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.3476 0.6826 -2.2562 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7971 -0.9603 1.1227 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1164 -0.5598 3.5407 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8252 -0.7947 3.1185 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7505 -2.7806 -1.2221 H 0 0 0 0 0 0 0 0 0 0 0 0 8.2022 -5.0162 -1.4350 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 2 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 15 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 24 25 1 0 21 26 1 0 20 27 1 0 19 28 1 0 14 29 1 0 13 30 1 0 30 31 1 0 31 32 1 0 32 33 1 0 33 34 1 0 34 35 1 0 34 36 1 0 36 37 1 0 33 38 1 0 32 39 1 0 31 40 1 0 12 41 1 0 3 42 1 0 6 1 1 0 17 7 1 0 16 11 1 0 23 18 1 0 35 30 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 8 47 1 0 18 48 1 0 19 49 1 0 20 50 1 0 21 51 1 0 22 52 1 0 24 53 1 0 24 54 1 0 25 55 1 0 26 56 1 0 27 57 1 0 28 58 1 0 29 59 1 0 30 60 1 0 31 61 1 0 32 62 1 0 33 63 1 0 34 64 1 0 36 65 1 0 36 66 1 0 37 67 1 0 38 68 1 0 39 69 1 0 40 70 1 0 41 71 1 0 42 72 1 0 M END

Standard InCHIKey	FIAAVMJLAGNUKW-DAMJSERUSA-N
Standard InCHI	InChI=1S/C27H30O15/c28-6-12-17(32)21(36)23(38)26(41-12)15-19(34)14-10(31)5-11(8-1-3-9(30)4-2-8)40-25(14)16(20(15)35)27-24(39)22(37)18(33)13(7-29)42-27/h1-5,12-13,17-18,21-24,26-30,32-39H,6-7H2/t12-,13-,17-,18-,21+,22+,23-,24-,26?,27?/m1/s1
SMILES	C1=CC(=CC=C1C2=CC(=O)C3=C(C(=C(C(=C3O2)C4C(C(C(C(O4)CO)O)O)O)O)C5C(C(C(C(O5)CO)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	594.16	Volume:	543.527 ? Van der Waals volume.
Dense:	1.093	LogP:	-1.67 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.068 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.558 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	30.0
TPSA:	271.2 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	11.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.147	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.818	Fsp³:	0.444
MCE-18:	122.949 ? 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:	0.222	Fluc inhibitor:	0.028 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.812 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.918 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.434	Promiscuous compounds:	0.343

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.445	MDCK Permeability:	-4.847
Pgp-inhibitor:	0.0	Pgp-substrate:	0.962
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):	0.994
20% Bioavailability (F20%):	0.929	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.969
Plasma Protein Binding (PPB):	82.321%	Volume Distribution (VD):	0.082
Fu:	15.014% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.0
OATP1B3 inhibitor:	0.255	BCRP inhibitor:	0.007
BSEP inhibitor:	0.005

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.975	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.021	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.976
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):

2.581

Half-life (T1/2):

3.889

ADMET: Toxicity

hERG Blockers:	0.011	hERG Blockers (10um):	0.166
Human Hepatotoxicity (H-HT):	0.65	Drug-induced Liver Injury (DILI):	0.834
AMES Toxicity:	0.699	Rat Oral Acute Toxicity:	0.425
Maximum Recommended Daily Dose:	0.471	Skin Sensitization:	0.253
Carcinogencity:	0.225	Eye Corrosion:	0.0
Eye Irritation:	0.023	Respiratory Toxicity:	0.024
Drug-induced Neurotoxicity:	0.037	Ototoxicity:	0.982
Hematotoxicity:	0.033	Drug-induced Nephrotoxicity:	0.036
Genotoxicity:	0.953	RPMI-8226 Immunitoxicity:	0.121
A549 Cytotoxicity:	0.134	Hek293 Cytotoxicity:	0.802
BCF:	0.252 ? 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:	2.537 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.694 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.472 ? 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
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[ 21030913]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	stem	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1007/s11418-006-0112-9]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.indcrop.2008.08.002]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO30786	Viola yedoensis	Species	Violaceae	Eukaryota	n.a.	leaf	n.a.	PMID[25562805]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	roots	n.a.	n.a.	PMID[26259802]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34771092]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37120447]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38786901]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[6387056]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO30786	Viola yedoensis	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO30786	Viola yedoensis	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO30786	Viola yedoensis	Species	Violaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26589	Artemisia annua L.	Strain	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29401	Bupleurum chinense	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26589	Artemisia annua L.	Strain	Asteraceae	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 NPC323526 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	23876
0.1-0.2	23644
0.2-0.3	1886
0.3-0.4	376
0.4-0.5	47
0.5-0.6	16
0.6-0.7	7
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC112701
0.8732	High Similarity	NPC326592
0.8732	High Similarity	NPC109594
0.7714	Intermediate Similarity	NPC209846
0.7361	Intermediate Similarity	NPC328740
0.7361	Intermediate Similarity	NPC289774
0.6667	Remote Similarity	NPC117418
0.6374	Remote Similarity	NPC482721
0.6364	Remote Similarity	NPC53545
0.6329	Remote Similarity	NPC10807
0.6329	Remote Similarity	NPC161881
0.6104	Remote Similarity	NPC268193
0.6071	Remote Similarity	NPC190393
0.5862	Remote Similarity	NPC47923
0.5833	Remote Similarity	NPC111249
0.5814	Remote Similarity	NPC472607
0.5513	Remote Similarity	NPC477897
0.55	Remote Similarity	NPC289771
0.5393	Remote Similarity	NPC603300
0.5357	Remote Similarity	NPC602537
0.5281	Remote Similarity	NPC44947
0.5185	Remote Similarity	NPC56232
0.5185	Remote Similarity	NPC150123
0.5185	Remote Similarity	NPC608009
0.5181	Remote Similarity	NPC177308
0.5176	Remote Similarity	NPC304745
0.5132	Remote Similarity	NPC10097
0.5109	Remote Similarity	NPC218488
0.506	Remote Similarity	NPC124478

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC323526 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5950
0.1-0.2	3146
0.2-0.3	48
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
0.506	Remote Similarity	NPD4380	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