NPASS Compound

Natural Product: NPC115872

Natural Product ID	NPC115872
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	HASVPNDDKSXPGU-WGNLCONDSA-O
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	23724704
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0001361] Anthocyanins [CHEMONTID:0002996] Anthocyanidin-3-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 73 77 0 0 0 0 0 0 0 0999 V2000 2.4989 -3.4923 -0.0190 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1999 -4.7203 -0.4988 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5231 -4.7894 -1.7012 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1784 -3.6363 -2.3672 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4884 -2.3776 -1.8716 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1613 -2.2910 -0.6720 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6288 -1.0676 -0.0510 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9873 0.1351 -0.2133 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6002 1.2295 0.4769 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7165 1.0236 1.2144 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3426 2.0763 1.9068 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4677 1.8387 2.6454 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0490 0.5952 2.7608 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4345 -0.4318 2.0828 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3000 -0.2210 1.3311 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7188 -1.1905 0.6900 O 0 0 0 0 0 3 0 0 0 0 0 0 7.1826 0.3520 3.5041 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7779 3.3460 1.8092 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9025 0.3608 -0.9077 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1755 0.5791 -1.5988 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.2621 1.3208 -0.8181 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5327 2.6949 -1.3953 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2084 3.2492 -1.8318 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2667 2.4379 -3.0049 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7871 2.6916 -3.0840 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0810 4.0185 -3.2574 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0888 1.1314 -2.8344 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2975 4.6078 -2.1624 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.0979 3.4932 -0.3850 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4578 0.6472 -0.8794 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9826 0.2164 0.3303 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2901 0.8454 0.6869 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1733 -0.0229 1.5502 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.0822 -1.4749 1.2216 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5873 -1.8250 1.2902 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5202 -3.3122 0.9763 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1229 -4.0318 2.0149 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9898 -1.1652 0.2575 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7037 -2.1857 2.2603 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.4746 0.4732 1.5475 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1158 2.0338 1.4386 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1906 -6.0261 -2.2380 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0373 -3.4376 0.9408 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4598 -5.6376 0.0034 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6468 -3.6874 -3.3122 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2660 -1.4892 -2.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1412 2.1797 0.3800 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9647 2.6553 3.1903 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8337 -1.4361 2.1270 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8309 1.1332 3.6187 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0648 3.6399 2.4658 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6879 -0.4583 -1.8061 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8648 1.4607 0.1855 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1819 2.6556 -2.2955 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4930 3.0841 -0.9921 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2100 2.8583 -3.9359 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1805 2.1366 -3.9832 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2812 2.2431 -2.2055 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9286 4.2869 -4.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4853 5.1298 -1.3515 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0401 3.6481 -0.6452 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2444 0.5397 1.1136 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8492 1.0678 -0.2442 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7985 0.0866 2.6119 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4879 -1.7430 0.2368 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2281 -1.5945 2.2932 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4929 -3.6548 0.7685 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1269 -3.5438 0.0674 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5665 -4.0730 2.8142 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2681 -1.8532 3.0965 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6209 1.1584 2.2424 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2343 2.0324 1.9082 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7612 -6.5238 -2.9006 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 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 2 0 15 16 1 0 13 17 1 0 11 18 1 0 8 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 24 27 1 0 23 28 1 0 22 29 1 0 21 30 1 0 30 31 1 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 34 39 1 0 33 40 1 0 32 41 1 0 3 42 1 0 6 1 1 0 16 7 2 0 27 20 1 0 38 31 1 0 15 10 1 0 1 43 1 0 2 44 1 0 4 45 1 0 5 46 1 0 9 47 1 0 12 48 1 0 14 49 1 0 17 50 1 0 18 51 1 0 20 52 1 6 21 53 1 1 22 54 1 6 23 55 1 1 24 56 1 6 25 57 1 0 25 58 1 0 26 59 1 0 28 60 1 0 29 61 1 0 31 62 1 1 32 63 1 6 33 64 1 1 34 65 1 6 35 66 1 1 36 67 1 0 36 68 1 0 37 69 1 0 39 70 1 0 40 71 1 0 41 72 1 0 42 73 1 0 M CHG 1 16 1 M END

Standard InCHIKey	HASVPNDDKSXPGU-WGNLCONDSA-O
Standard InCHI	InChI=1S/C27H30O15/c28-8-17-19(33)21(35)23(37)26(40-17)42-25-22(36)20(34)18(9-29)41-27(25)39-16-7-13-14(32)5-12(31)6-15(13)38-24(16)10-1-3-11(30)4-2-10/h1-7,17-23,25-29,33-37H,8-9H2,(H2-,30,31,32)/p+1/t17-,18-,19-,20-,21+,22+,23-,25-,26+,27-/m1/s1
SMILES	c1cc(ccc1c1c(cc2c(cc(cc2[o+]1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	595.17	Volume:	544.846 ? Van der Waals volume.
Dense:	1.092	LogP:	-0.722 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.382 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.315 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	29.0
TPSA:	250.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	10.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.14	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.864	Fsp³:	0.444
MCE-18:	115.923 ? 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:	0.716	Fluc inhibitor:	0.261 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.896 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.619 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.584	Promiscuous compounds:	0.541

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.875	MDCK Permeability:	-4.828
Pgp-inhibitor:	0.0	Pgp-substrate:	0.844
PAMPA:	0.997 ? 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):	0.928
20% Bioavailability (F20%):	0.796	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.007
Plasma Protein Binding (PPB):	84.227%	Volume Distribution (VD):	-0.031
Fu:	15.958% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.24
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.235	CYP2D6-substrate:	0.001
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.944
HLM stability:	0.033 ? 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):

1.329

Half-life (T1/2):

4.174

ADMET: Toxicity

hERG Blockers:	0.001	hERG Blockers (10um):	0.008
Human Hepatotoxicity (H-HT):	0.99	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.999	Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.222	Skin Sensitization:	1.0
Carcinogencity:	1.0	Eye Corrosion:	0.0
Eye Irritation:	0.975	Respiratory Toxicity:	0.07
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.141
Hematotoxicity:	0.003	Drug-induced Nephrotoxicity:	0.007
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.024
A549 Cytotoxicity:	0.037	Hek293 Cytotoxicity:	0.821
BCF:	0.332 ? 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:	2.585 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.136 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.499 ? 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
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[ 10835233]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.1016/j.foodchem.2008.09.013]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10388717]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10820136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11695850]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1282214]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15102880]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15123652]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[15239850]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15466478]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16538977]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17499416]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18039809]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1814736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1928373]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19572262]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19662622]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20951405]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[21381697]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2188748]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23384552]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23723388]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24085302]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24096206]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24343604]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24503197]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24814225]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25070706]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25727742]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26041992]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26485038]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26608498]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26654758]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26676627]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466123]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3025936]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	Flowers	SÃƒÂ£o Paulo, Brazil.		PMID[32156350]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[37570937]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4002232]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[518564]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6273168]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6572072]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6806263]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6825837]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6833497]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7311739]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[7645303]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8069858]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8452569]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9179722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9435160]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9606952]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9629662]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9660093]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9694933]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	Fruits	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.		Database[Phenol-Explorer]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10300	Tropaeolum majus	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19774	Rubus idaeus	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO17164	Rattus norvegicus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20338	Mus musculus	Species	Muridae	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
NPO19774	Rubus idaeus	n.a.	Fruits	3.46097	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]

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 NPC115872 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	22418
0.1-0.2	23338
0.2-0.3	3605
0.3-0.4	451
0.4-0.5	34
0.5-0.6	7
0.6-0.7	5
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	Natural Product ID
0.7108	Intermediate Similarity	NPC473621
0.6711	Remote Similarity	NPC168579
0.6375	Remote Similarity	NPC76176
0.6296	Remote Similarity	NPC125755
0.6154	Remote Similarity	NPC37793
0.6	Remote Similarity	NPC277867
0.5926	Remote Similarity	NPC603591
0.5714	Remote Similarity	NPC473480
0.5714	Remote Similarity	NPC161700
0.5222	Remote Similarity	NPC170052
0.5222	Remote Similarity	NPC135846
0.5106	Remote Similarity	NPC15538
0.506	Remote Similarity	NPC138227

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC115872 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6912
0.1-0.2	2181
0.2-0.3	53
0.3-0.4	4
0.4-0.5	0
0.5-0.6	0
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
		NPD

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