NPASS Compound

Natural Product: NPC54341

Natural Product ID	NPC54341
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	OMQADRGFMLGFJF-GDRLQRQZSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	13872461
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-glycosides

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 74 78 0 0 0 0 0 0 0 0999 V2000 -6.2483 -2.4352 1.4199 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1147 -1.7167 0.4155 C 0 0 1 0 0 0 0 0 0 0 0 0 -8.0857 -0.8714 1.2034 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7296 0.5895 1.1378 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.2673 0.8718 1.1624 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.4600 -0.1241 0.4220 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6018 0.5959 -0.4351 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.2629 0.1838 -0.2075 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2821 1.0188 -0.9336 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5096 1.2503 -2.4082 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6826 2.4854 -2.7363 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7087 2.9005 -1.6783 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2307 1.8828 -0.7327 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0997 1.5481 -0.7587 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8285 0.4318 -0.5104 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3411 -0.8491 -0.3291 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1817 -1.9031 -0.0872 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5353 -1.7687 -0.0040 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4272 -2.8901 0.2408 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9914 -4.0168 0.5905 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9037 -2.6377 0.0570 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1636 -1.3061 0.7110 C 0 0 0 0 0 0 0 0 0 0 0 0 7.5534 -0.8900 0.7860 C 0 0 0 0 0 0 0 0 0 0 0 0 8.6036 -1.7726 0.5196 C 0 0 0 0 0 0 0 0 0 0 0 0 9.9050 -1.3591 0.6188 C 0 0 0 0 0 0 0 0 0 0 0 0 10.2315 -0.0557 0.9886 C 0 0 0 0 0 0 0 0 0 0 0 0 9.2182 0.8194 1.2534 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9101 0.4093 1.1529 C 0 0 0 0 0 0 0 0 0 0 0 0 9.5451 2.1329 1.6260 O 0 0 0 0 0 0 0 0 0 0 0 0 11.5500 0.3540 1.0891 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4431 -0.3367 -0.0889 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0454 -0.4839 -0.1796 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2260 0.5953 -0.4279 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6612 -3.2133 0.0931 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9668 0.6619 -0.8227 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2891 3.9703 -0.9536 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0425 2.2132 -3.9621 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8185 1.4430 -2.7704 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2791 -0.9150 -0.3721 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8224 1.0936 2.4689 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.2811 1.2318 2.2708 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.3438 -1.0385 0.6324 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3249 -2.8575 0.9644 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0306 -1.7769 2.3112 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7869 -3.3152 1.8764 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5953 -2.4566 -0.2305 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1511 -1.2126 2.2548 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2432 1.0634 0.2800 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1471 1.8745 0.6613 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8055 -0.7460 1.0695 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1016 0.3303 0.9040 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1236 -0.8924 -0.4562 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4034 2.0836 -0.4843 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0365 0.3612 -2.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4238 3.3111 -2.9714 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1313 3.4216 -2.2386 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4690 2.1448 0.3547 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2775 -1.0399 -0.3764 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0278 -2.4437 -1.0573 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5219 -3.4661 0.3883 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7349 -1.3244 1.7408 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3944 -2.8012 0.2215 H 0 0 0 0 0 0 0 0 0 0 0 0 10.7174 -2.0529 0.4016 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0969 1.0950 1.3680 H 0 0 0 0 0 0 0 0 0 0 0 0 9.2121 2.9370 1.0766 H 0 0 0 0 0 0 0 0 0 0 0 0 11.7828 1.3211 0.9686 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6800 1.5817 -0.5639 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0535 -3.4307 0.8766 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8303 4.5008 -1.6069 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4800 1.4618 -4.4298 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2290 0.6081 -3.1708 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0286 1.7194 2.4990 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1303 2.2215 2.2294 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.6270 -0.3202 0.0280 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 19 21 1 0 21 22 1 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 27 29 1 0 26 30 1 0 22 31 1 0 31 32 1 0 32 33 2 0 17 34 1 0 13 35 1 0 12 36 1 0 11 37 1 0 10 38 1 0 6 39 1 0 5 40 1 0 4 41 1 0 3 42 1 0 39 2 1 0 35 9 1 0 33 15 1 0 32 18 1 0 28 23 1 0 1 43 1 0 1 44 1 0 1 45 1 0 2 46 1 6 3 47 1 1 4 48 1 6 5 49 1 6 6 50 1 1 8 51 1 0 8 52 1 0 9 53 1 1 10 54 1 6 11 55 1 6 12 56 1 6 13 57 1 1 16 58 1 0 21 59 1 0 21 60 1 0 22 61 1 0 24 62 1 0 25 63 1 0 28 64 1 0 29 65 1 0 30 66 1 0 33 67 1 0 34 68 1 0 36 69 1 0 37 70 1 0 38 71 1 0 40 72 1 0 41 73 1 0 42 74 1 0 M END

Standard InCHIKey	OMQADRGFMLGFJF-GDRLQRQZSA-N
Standard InCHI	InChI=1S/C27H32O15/c1-9-20(32)22(34)24(36)26(39-9)38-8-18-21(33)23(35)25(37)27(42-18)40-11-5-14(30)19-15(31)7-16(41-17(19)6-11)10-2-3-12(28)13(29)4-10/h2-6,9,16,18,20-30,32-37H,7-8H2,1H3/t9-,16?,18+,20-,21+,22+,23-,24+,25+,26+,27+/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](Oc3cc(c4C(=O)CC(c5ccc(c(c5)O)O)Oc4c3)O)O2)O)O)O)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	596.17	Volume:	546.164 ? Van der Waals volume.
Dense:	1.092	LogP:	0.469 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.018 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.324 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	30.0
TPSA:	245.29 ? 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:	0.173	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.845	Fsp³:	0.519
MCE-18:	121.902 ? 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:	1
Colloidal aggregators:	0.607	Fluc inhibitor:	0.415 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.258 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.411 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.131	Promiscuous compounds:	0.182

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.616	MDCK Permeability:	-5.108
Pgp-inhibitor:	0.0	Pgp-substrate:	0.156
PAMPA:	0.999 ? 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):	0.981
20% Bioavailability (F20%):	0.546	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.081
Plasma Protein Binding (PPB):	80.534%	Volume Distribution (VD):	-0.176
Fu:	17.608% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.906
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.064	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:	0.037
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.938
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.816
HLM stability:	0.765 ? 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):

1.418

Half-life (T1/2):

4.811

ADMET: Toxicity

hERG Blockers:	0.027	hERG Blockers (10um):	0.367
Human Hepatotoxicity (H-HT):	0.58	Drug-induced Liver Injury (DILI):	0.964
AMES Toxicity:	0.893	Rat Oral Acute Toxicity:	0.046
Maximum Recommended Daily Dose:	0.051	Skin Sensitization:	0.993
Carcinogencity:	0.044	Eye Corrosion:	0.0
Eye Irritation:	0.456	Respiratory Toxicity:	0.017
Drug-induced Neurotoxicity:	0.001	Ototoxicity:	0.981
Hematotoxicity:	0.094	Drug-induced Nephrotoxicity:	0.87
Genotoxicity:	0.812	RPMI-8226 Immunitoxicity:	0.171
A549 Cytotoxicity:	0.919	Hek293 Cytotoxicity:	0.393
BCF:	0.453 ? 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:	3.14 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.868 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.956 ? 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
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(00)94055-X]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(99)00119-3]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	flower	n.a.	DOI[10.3390/70200245]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10606602]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17689080]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[23872723]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24617303]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32996318]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[33937995]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34771092]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34771092]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35143705]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35268681]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37049761]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37049761]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38159180]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38308284]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38786901]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39410132]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28295	Foeniculum vulgare	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]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7317	Citrus aurantium	Species	Rutaceae	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]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	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[TM-MC]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28295	Foeniculum vulgare	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15730	Citrus medica	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21771	Citrus trifoliata	Species	Rutaceae	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 NPC54341 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	12318
0.1-0.2	31974
0.2-0.3	4590
0.3-0.4	805
0.4-0.5	139
0.5-0.6	20
0.6-0.7	5
0.7-0.8	0
0.8-0.85	2
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC43587
0.8718	High Similarity	NPC271270
0.8395	Intermediate Similarity	NPC44328
0.8395	Intermediate Similarity	NPC79056
0.7857	Intermediate Similarity	NPC293629
0.7191	Intermediate Similarity	NPC67134
0.7125	Intermediate Similarity	NPC29830
0.6932	Remote Similarity	NPC291124
0.6932	Remote Similarity	NPC131157
0.6292	Remote Similarity	NPC105283
0.6087	Remote Similarity	NPC241016
0.6071	Remote Similarity	NPC39351
0.5978	Remote Similarity	NPC142860
0.5978	Remote Similarity	NPC152538
0.5978	Remote Similarity	NPC246469
0.5978	Remote Similarity	NPC89088
0.5789	Remote Similarity	NPC105095
0.5789	Remote Similarity	NPC177731
0.5789	Remote Similarity	NPC725
0.5765	Remote Similarity	NPC97052
0.573	Remote Similarity	NPC236934
0.5698	Remote Similarity	NPC219163
0.5638	Remote Similarity	NPC97285
0.5581	Remote Similarity	NPC163191
0.5488	Remote Similarity	NPC469622
0.5301	Remote Similarity	NPC480158
0.52	Remote Similarity	NPC47140
0.5192	Remote Similarity	NPC318119
0.5116	Remote Similarity	NPC479450
0.5111	Remote Similarity	NPC40664
0.5111	Remote Similarity	NPC197723
0.5051	Remote Similarity	NPC190450

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC54341 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3868
0.1-0.2	5180
0.2-0.3	87
0.3-0.4	11
0.4-0.5	3
0.5-0.6	0
0.6-0.7	0
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	Drug ID	Developmental Stage
0.8395	Intermediate Similarity	NPD7074	Phase 3

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