NPASS Compound

Natural Product: NPC140454

Natural Product ID	NPC140454
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	ONQVTPMFYSRRLL-HUJUZFAXSA-O
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	90470732
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 76 80 0 0 0 0 0 0 0 0999 V2000 5.4727 1.4564 -2.8260 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2873 1.5905 -1.3542 C 0 0 1 0 0 0 0 0 0 0 0 0 6.6332 1.8823 -0.7309 C 0 0 1 0 0 0 0 0 0 0 0 0 6.4101 2.9864 0.3021 C 0 0 2 0 0 0 0 0 0 0 0 0 5.2431 2.4761 1.1574 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9676 2.4873 0.3156 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2389 1.3653 0.5576 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9490 1.6094 1.0885 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2392 0.2829 1.2441 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1543 -0.4226 -0.1125 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9638 -1.8829 0.2609 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0554 -1.9902 1.3200 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8402 -0.7010 1.5975 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8806 -0.5818 0.6403 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0299 -1.3086 0.6696 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3095 -2.2336 1.6853 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4877 -2.9232 1.6060 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7895 -3.8425 2.5872 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9761 -4.5282 2.4813 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8643 -4.3490 1.4620 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5251 -3.4074 0.4851 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3577 -2.7054 0.5527 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0361 -1.8258 -0.3572 O 0 0 0 0 0 3 0 0 0 0 0 0 -3.9232 -1.1118 -0.3559 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7182 -0.1746 -1.4433 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4818 -0.3455 -2.5947 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4855 0.4966 -3.6766 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6610 1.5952 -3.5952 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8757 1.8369 -2.4869 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9277 0.9271 -1.4271 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0582 2.9815 -2.4487 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2932 3.1996 -1.2805 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5761 2.5346 -4.6376 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0550 -5.0477 1.3611 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9214 -4.0561 3.6281 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0332 0.3917 1.7209 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4310 -2.4636 2.5243 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7531 -2.6851 -0.8522 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3157 -0.2408 -0.8523 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3620 2.5902 -1.0295 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1003 3.3099 2.2505 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0849 4.1696 -0.3099 O 0 0 0 0 0 0 0 0 0 0 0 0 6.9993 0.7544 0.0135 O 0 0 0 0 0 0 0 0 0 0 0 0 5.6475 2.4407 -3.2979 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4159 0.8634 -2.9824 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6903 0.8576 -3.3400 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9216 0.6333 -0.9444 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4096 2.1162 -1.4559 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2873 3.1302 0.9462 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4581 1.4677 1.5391 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4322 3.4176 0.5823 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0656 2.0787 2.0861 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4038 2.3037 0.4278 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8541 -0.3159 1.9546 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2418 -0.0931 -0.6381 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9436 -2.2166 0.6916 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8195 -2.7378 0.9687 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3204 -0.9132 2.5666 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5990 -2.3751 2.4874 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2358 -5.2611 3.2468 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1982 -3.2328 -0.3466 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1264 -1.2344 -2.6282 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0918 0.3383 -4.5510 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3261 1.1273 -0.5728 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9355 3.0944 -0.3528 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9490 4.2719 -1.2200 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3960 2.5821 -1.2144 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6432 3.5113 -4.3288 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1156 -5.9408 1.8308 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1607 -4.7280 3.5525 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0201 -1.9832 3.2865 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3727 -3.4834 -0.8729 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0703 -0.4613 -1.7915 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1419 3.2866 2.5008 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1977 4.9450 0.2888 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8999 0.4141 -0.2261 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 2 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 1 0 28 33 1 0 20 34 1 0 18 35 1 0 13 36 1 0 12 37 1 0 11 38 1 0 10 39 1 0 6 40 1 0 5 41 1 0 4 42 1 0 3 43 1 0 40 2 1 0 36 9 1 0 24 15 1 0 30 25 1 0 22 17 1 0 1 44 1 0 1 45 1 0 1 46 1 0 2 47 1 1 3 48 1 6 4 49 1 1 5 50 1 1 6 51 1 1 8 52 1 0 8 53 1 0 9 54 1 1 10 55 1 6 11 56 1 1 12 57 1 6 13 58 1 1 16 59 1 0 19 60 1 0 21 61 1 0 26 62 1 0 27 63 1 0 30 64 1 0 32 65 1 0 32 66 1 0 32 67 1 0 33 68 1 0 34 69 1 0 35 70 1 0 37 71 1 0 38 72 1 0 39 73 1 0 41 74 1 0 42 75 1 0 43 76 1 0 M CHG 1 23 1 M END

Standard InCHIKey	ONQVTPMFYSRRLL-HUJUZFAXSA-O
Standard InCHI	InChI=1S/C28H33O15/c1-10-20(32)22(34)24(36)27(40-10)39-9-19-21(33)23(35)25(37)28(43-19)42-18-8-13-15(31)6-12(29)7-16(13)41-26(18)11-3-4-14(30)17(5-11)38-2/h3-8,10,19-25,27-37H,9H2,1-2H3/q+1/t10-,19+,20-,21+,22+,23-,24+,25+,27+,28+/m0/s1
SMILES	C[C@H]1[C@@H]([C@H]([C@H]([C@H](OC[C@@H]2[C@H]([C@@H]([C@H]([C@H](Oc3cc4c(cc(cc4[o+]c3c3ccc(c(c3)OC)O)O)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	609.18	Volume:	562.142 ? Van der Waals volume.
Dense:	1.084	LogP:	0.221 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.851 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.847 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	29.0
TPSA:	239.52 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	9.0	Rings:	5.0
Heavy Atoms:	15.0

MedChem Properties

QED Drug-Likeness Score:	0.154	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.92	Fsp³:	0.464
MCE-18:	118.585 ? 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:	1	PAINS Alert:	0
Colloidal aggregators:	0.688	Fluc inhibitor:	0.279 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.938 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.589 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.301	Promiscuous compounds:	0.437

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.392	MDCK Permeability:	-5.254
Pgp-inhibitor:	0.0	Pgp-substrate:	0.967
PAMPA:	0.984 ? 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):	0.071
20% Bioavailability (F20%):	0.291	30% Bioavailability (F30%):	0.974
50% Bioavailability (F50%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.131
Plasma Protein Binding (PPB):	82.62%	Volume Distribution (VD):	-0.131
Fu:	16.623% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.853
BSEP inhibitor:	0.009

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:	0.068
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.978
HLM stability:	0.031 ? 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):

1.568

Half-life (T1/2):

4.987

ADMET: Toxicity

hERG Blockers:	0.005	hERG Blockers (10um):	0.042
Human Hepatotoxicity (H-HT):	0.944	Drug-induced Liver Injury (DILI):	1.0
AMES Toxicity:	0.998	Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.621	Skin Sensitization:	0.999
Carcinogencity:	1.0	Eye Corrosion:	0.0
Eye Irritation:	0.923	Respiratory Toxicity:	0.207
Drug-induced Neurotoxicity:	0.0	Ototoxicity:	0.06
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.001
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.053	Hek293 Cytotoxicity:	0.883
BCF:	0.492 ? 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:	3.006 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.401 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.532 ? 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
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	DOI[10.1016/j.foodchem.2007.08.004]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	DOI[10.1016/j.phytochem.2007.01.008]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit	n.a.	n.a.	DOI[10.1016/S0963-9969(99)00095-2]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	Aerial parts	n.a.	n.a.	PMID[10395493]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11534769]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	kernel	n.a.	PMID[12232058]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	fruit	n.a.	PMID[16417304]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17328933]
NPO14284	Delphinium shawurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20351801]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21648406]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[36557810]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38279238]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[8988596]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9917288]
NPO3949	Ceramium rubrum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27436	Ribes uva-crispa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12982	Dysidea amblia	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6347	Iryanthera paraensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11912	Peltogyne porphyrocardia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10887	Pseudeurotium zonatum	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28601	Aspergillus falconensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15160	Gutierrezia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14043	Caulerpa serrulata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7713	Euplotes raikovi	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO27436	Ribes uva-crispa	Species	n.a.	n.a.		n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Bulb	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO27436	Ribes uva-crispa	Species	n.a.	n.a.	Fruit	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Leaf	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Seed	n.a.	n.a.	Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Seed Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO27436	Ribes uva-crispa	Species	n.a.	n.a.	Fruits	n.a.		Database[FooDB]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[FooDB]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7546	Prunus domestica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13477	Cyberlindnera jadinii	Species	Phaffomycetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3244	Ascidia ahodori	Species	Ascidiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4512	Fagraea gracilipes	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15160	Gutierrezia lucida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13160	Garcinia xipshuanbannaensis	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6347	Iryanthera paraensis	Species	Myristicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15253	Helichrysum graveolens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11912	Peltogyne porphyrocardia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11128	Ratibida mexicana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13311	Agelas linnaei	Species	Agelasidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10191	Ormosia balansae	Species	Limoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15626	Alternaria japonica	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1751	Ribes nigrum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO7713	Euplotes raikovi	Species	Euplotidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO965	Bleekeria vitiensis	Species	Plesiopidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27436	Ribes uva-crispa	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO2458	Aconitum violaceum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15442	Magnolia sieboldii	Species	Magnoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14043	Caulerpa serrulata	Species	Caulerpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10887	Pseudeurotium zonatum	Species	Pseudeurotiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16741	Codonopsis pilosula	Species	Campanulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12756	Roboastra tigris	Species	Polyceridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14673	Lathyrus nissolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14178	Leonurus persicus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14284	Delphinium shawurense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9860.1	Pinus brutia var. eldarica	Varieties	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28601	Aspergillus falconensis	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12982	Dysidea amblia	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3949	Ceramium rubrum	Species	Ceramiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24693	Prunus cerasus	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15336	Prunus avium	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7546	Prunus domestica	Species	Rosaceae	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
NPO15336	Prunus avium	Raw	n.a.	7.416894957	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO15336	Prunus avium	n.a.	n.a.	1.925499916	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO1751	Ribes nigrum	Raw	n.a.	1.280259152	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO24693	Prunus cerasus	Raw	n.a.	2.700000048	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO27436	Ribes uva-crispa	Raw	n.a.	0.108515117	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO7546	Prunus domestica	Raw	n.a.	4.849999905	n.a.	n.a.	mg/100g	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 NPC140454 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	17008
0.1-0.2	29244
0.2-0.3	3005
0.3-0.4	511
0.4-0.5	76
0.5-0.6	11
0.6-0.7	1
0.7-0.8	0
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
0.8434	Intermediate Similarity	NPC15538
0.7229	Intermediate Similarity	NPC125755
0.6437	Remote Similarity	NPC473480
0.5977	Remote Similarity	NPC277867
0.5955	Remote Similarity	NPC76176
0.5909	Remote Similarity	NPC603591
0.5714	Remote Similarity	NPC161700
0.5682	Remote Similarity	NPC168579
0.5588	Remote Similarity	NPC476472
0.5588	Remote Similarity	NPC294815
0.5588	Remote Similarity	NPC16194
0.53	Remote Similarity	NPC473621
0.5222	Remote Similarity	NPC37793
0.5096	Remote Similarity	NPC473327

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC140454 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6014
0.1-0.2	3094
0.2-0.3	35
0.3-0.4	2
0.4-0.5	5
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