NPASS Compound

Natural Product: NPC43587

Natural Product ID	NPC43587
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Eriocitrin
IUPAC Name	(2S)-2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
Synonyms	Eriocitrin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2165586
PubChem CID	83489
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 -4.1915 -2.2292 2.4204 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6467 -2.7994 1.1145 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.1372 -2.6290 0.9168 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.4250 -2.9921 -0.5248 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8946 -1.8716 -1.3916 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.6727 -1.2958 -0.6610 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8009 -0.8064 -1.6199 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5394 0.5292 -1.5734 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8943 1.0278 -0.3085 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8179 2.5604 -0.3142 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4100 2.9525 1.0845 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0997 2.3075 1.3739 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6605 1.3108 0.3192 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0791 1.9660 -0.7573 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2456 1.8934 -1.1236 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6811 2.6092 -2.2549 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9754 2.5956 -2.6903 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9076 1.8502 -1.9980 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3084 1.7912 -2.4112 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6448 2.2342 -3.5277 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3166 1.1904 -1.4658 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6787 -0.0035 -0.8478 C 0 0 1 0 0 0 0 0 0 0 0 0 6.5703 -0.7714 0.0639 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9050 -0.4440 0.1152 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7852 -1.1367 0.9553 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2748 -2.1537 1.7271 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9415 -2.4984 1.6917 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1132 -1.7911 0.8520 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4722 -3.5393 2.4950 O 0 0 0 0 0 0 0 0 0 0 0 0 9.1648 -2.8322 2.5570 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4918 0.3770 -0.1868 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5535 1.1264 -0.8839 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2177 1.1684 -0.4731 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4013 3.3050 -3.8095 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6871 0.4497 -0.0454 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0508 1.6921 2.6241 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3989 4.3312 1.2615 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.0913 3.0679 -0.5630 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9859 -2.2983 0.0217 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8770 -0.8843 -1.4429 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7843 -3.2050 -0.7406 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.8598 -3.4345 1.7973 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3077 -2.7825 2.7985 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9000 -1.1702 2.3139 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0462 -2.3466 3.1445 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4047 -3.9028 1.1493 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3745 -1.5539 1.0492 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8360 -3.9067 -0.8060 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6191 -2.2166 -2.4119 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0123 -0.4771 -0.0204 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4605 1.1205 -1.7573 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8172 0.7506 -2.3999 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5682 0.7901 0.5389 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1683 2.9361 -1.1018 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1730 2.5081 1.7716 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3060 3.0988 1.3928 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0931 0.6771 0.8193 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9555 3.1926 -2.7988 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5815 1.9806 -0.7523 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2095 0.9103 -2.0873 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3813 -0.6923 -1.6792 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3137 0.3690 -0.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 9.8311 -0.8459 0.9650 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0671 -2.0488 0.8136 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0596 -4.2581 2.8527 H 0 0 0 0 0 0 0 0 0 0 0 0 10.0867 -3.1361 2.2421 H 0 0 0 0 0 0 0 0 0 0 0 0 1.9823 0.5921 0.3991 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1462 4.2710 -3.9209 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7651 1.0389 2.7149 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1235 4.7712 0.7719 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0189 3.9788 -0.9874 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5742 -1.1414 -2.0900 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.2450 -2.3541 -0.5740 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.6318 -2.8730 2.1051 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 1 3 47 1 6 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 1 12 56 1 1 13 57 1 1 16 58 1 0 21 59 1 0 21 60 1 0 22 61 1 6 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-MNPJBKLOSA-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)C[C@@H](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:	0.778 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.341 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-2.349 ? 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:	0.577	Fluc inhibitor:	0.499 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.157 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.386 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.127	Promiscuous compounds:	0.317

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.672	MDCK Permeability:	-5.145
Pgp-inhibitor:	0.0	Pgp-substrate:	0.126
PAMPA:	0.998 ? 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):	0.912
20% Bioavailability (F20%):	0.775	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.05
Plasma Protein Binding (PPB):	80.698%	Volume Distribution (VD):	-0.17
Fu:	17.424% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.999
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.672
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.003	CYP1A2-substrate:	0.001
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.999
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.74
HLM stability:	0.58 ? 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):

1.442

Half-life (T1/2):

4.847

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.29
Human Hepatotoxicity (H-HT):	0.72	Drug-induced Liver Injury (DILI):	0.985
AMES Toxicity:	0.916	Rat Oral Acute Toxicity:	0.087
Maximum Recommended Daily Dose:	0.104	Skin Sensitization:	0.997
Carcinogencity:	0.025	Eye Corrosion:	0.0
Eye Irritation:	0.614	Respiratory Toxicity:	0.061
Drug-induced Neurotoxicity:	0.006	Ototoxicity:	0.978
Hematotoxicity:	0.082	Drug-induced Nephrotoxicity:	0.946
Genotoxicity:	0.947	RPMI-8226 Immunitoxicity:	0.221
A549 Cytotoxicity:	0.969	Hek293 Cytotoxicity:	0.334
BCF:	0.474 ? 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:	3.171 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.933 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.997 ? 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]
NPO319	Citrus limon	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]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	fruit	n.a.	PMID[10606547]
NPO25443	Citrus reticulata	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]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[30183289]
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]
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[34771092]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35143705]
NPO319	Citrus limon	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]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36378844]
NPO19632	Terminalia ivorensis	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36964494]
NPO57629	Mentha Ã— piperita	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36985839]
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[37049761]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37893598]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38139796]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38139796]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38159180]
NPO57629	Mentha Ã— piperita	Genus	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38257205]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38308284]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38498554]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38786901]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39147955]
NPO7317	Citrus aurantium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39410132]
NPO12807	Citrus aurantiifolia	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]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5270	Citrus natsudaidai	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5386	Citrus paradisi	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]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Bark	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	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	Fruit	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Fruit Juice	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Leaf Essent. Oil	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Pericarp	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19787	Citrus sinensis	Species	Rutaceae	Eukaryota	Root Bark	n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO17752	Mentha X piperita	Strain	Lamiaceae	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]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
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]
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]
NPO319	Citrus limon	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]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10082	Citrus unshiu	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
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]
NPO27288	Citrus maxima	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21771	Citrus trifoliata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	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]
NPO15730	Citrus medica	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]
NPO5386	Citrus paradisi	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]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15730	Citrus medica	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]
NPO7317	Citrus aurantium	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]
NPO10082	Citrus unshiu	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]
NPO319	Citrus limon	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]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	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]
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]
NPO16308	Citrus wilsonii	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5386	Citrus paradisi	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12807	Citrus aurantiifolia	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25443	Citrus reticulata	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17752	Mentha X piperita	Strain	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28295	Foeniculum vulgare	Species	Apiaceae	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]
NPO1592	Citrullus colocynthis	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO319	Citrus limon	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19632	Terminalia ivorensis	Species	Combretaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21771	Citrus trifoliata	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]

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
NPO12807	Citrus aurantiifolia	Beverage (juice)	n.a.	5.445714406	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO12807	Citrus aurantiifolia	n.a.	n.a.	5.44571	n.a.	n.a.	mg/100mL	Database [Phenol-Explorer]
NPO1592	Citrullus colocynthis	n.a.	n.a.	1.23 Â± 0.08	n.a.	n.a.	mg/100g	PMID[37893598]
NPO17752	Mentha X piperita	Other	Leaf	86	86	86	mg/100g	Database [DUKE]
NPO17752	Mentha X piperita	Dried Or Powder	n.a.	8051.57963	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO17752	Mentha X piperita	n.a.	n.a.	8051.57963	n.a.	n.a.	mg/100g of FW	Database [Phenol-Explorer]
NPO19632	Terminalia ivorensis	Ethyl acetate extract	n.a.	5.8Â±1.4	n.a.	n.a.	ng/mg	PMID[36964494]
NPO19787	Citrus sinensis	Beverage (juice)	n.a.	0.362499996	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO319	Citrus limon	Raw	Fruit	0.1	0.1	0.1	mg/100g	Database [DUKE]
NPO319	Citrus limon	Beverage (juice)	n.a.	13.82096749	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO319	Citrus limon	Beverage (juice)	n.a.	21.29047612	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO319	Citrus limon	n.a.	n.a.	13.82097	n.a.	n.a.	mg/100mL	Database [Phenol-Explorer]
NPO319	Citrus limon	n.a.	n.a.	21.29048	n.a.	n.a.	mg/100mL	Database [Phenol-Explorer]
NPO5386	Citrus paradisi	Beverage (juice)	n.a.	0.157924531	n.a.	n.a.	mg/100g	Database [PHENOL EXPLORER]
NPO5386	Citrus paradisi	n.a.	n.a.	0.15792	n.a.	n.a.	mg/100mL	Database [Phenol-Explorer]
NPO57629	Mentha Ã— piperita	Dried	Leaves	285.37	n.a.	n.a.	mg/g	PMID[36985839]

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

Activity Type	# Activity
Inhibition	2
IC50	1
Activity	13

Activity Type	# Activity
Individual protein	3
Unchecked	6
Organism	6
Cell line	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1592	Individual protein	Dipeptidyl peptidase IV	Homo sapiens	IC50	=	10360.0	nM	PMID[29609120]
NPT67	Individual protein	Cholinesterase	Equus caballus	Inhibition	=	1.98	%	PMID[23062825]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	Inhibition	=	21.54	%	PMID[23062825]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT28438	Unchecked	Unchecked	n.a.	Activity	n.a.	n.a.	n.a.	PMID[34189920]
NPT22036	Cell line	HL	Homo sapiens	Activity	=	75.2	%	PMID[29043803]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	n.a.	n.a.	n.a.	PMID[34189920]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	25.37	g	PMID[34189920]

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 NPC43587 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	0

Similarity Score	Similarity Level	Natural Product ID
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 NPC43587 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