Apigenin 4\'-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide]



Compound IDCDAMM02020
Common nameApigenin 4\'-[feruloyl-(->2)-glucuronyl-(1->2)-glucuronide]
IUPAC name5-[6-carboxy-4,5-dihydroxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]oxan-2-yl]oxy-6-[4-(5,7-dihydroxy-4-oxochromen-2-yl)phenoxy]-3,4-dihydroxyoxane-2-carboxylic acid
Molecular formulaC37H34O20

Experimental data

Retention time16.26
Adduct[M+H]+
Actual mz799.179
Theoretical mz799.171
Error9.79
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.5601

Identifiers and class information

Inchi keyLNCEICCQWMCNS-YCRREMRBNA-N
SmilesO=C(O)C1OC(OC=2C=CC(=CC2)C=3OC=4C=C(O)C=C(O)C4C(=O)C3)C(OC5OC(C(=O)O)C(O)C(O)C5OC(=O)C=CC6=CC=C(O)C(OC)=C6)C(O)C1O
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Pharmacokinetic properties

Number of descriptor values(#stars)13
Number of non-conjugated amine groups (#amine)0
Number of amidine and guanidine groups (#amidine)0
Number of carboxylic acid groups (#acid)2
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)18
Number of reactive functional groups (#rtvFG)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)798.664
Computed dipole moment(dipole)7.002
Total solvent accessible surface area (SASA)1112.87
Hydrophobic component of SASA (FOSA)198.881
Hydrophilic component of SASA (FISA)556.437
Pie component of the SASA (PISA)357.548
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)2124.65
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)21.15
Free energy of solvation of dipole (dip^2/V)0.0230751
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0465525
Globularity descriptor (glob)0.718202
Predicted polarizability in cubic angstroms (QPpolrz)70.731
Predicted hexadecane/gas partition coefficient (QPlogPC16)26.482
Predicted octanol/gas partition coefficient (QPlogPoct)46.009
Predicted water/gas partition coefficient (QPlogPw)34.264
Predicted octanol/water partition coefficient (QPlogPo/w)0.721
Predicted aqueous solubility (QPlogS)-5.545
Conformation-independent predicted aqueous solubility (CIQPlogS)-7.969
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.182
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.003
Predicted brain/blood partition coefficient (QPlogBB)-7.713
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.001
Predicted skin permeability, log Kp (QPlogKp)-8.787
PM3 calculated ionization potential (IP(ev))8.985
PM3 calculated electron affinity (EA(eV))1.192
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-1.048
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
Solvent-accessible surface area of fluorine atoms (SAFluorine)0
Solvent-accessible surface area of amide oxygen atoms (SAamideO)0
Van der Waals surface area (PSA)348.853
Number of nitrogen and oxygen atoms (#NandO)20
Number of violations of Lipinski’s rule of five (RuleOfFive)3
Number of violations of Jorgensen’s rule of three (RuleOfThree)2

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
O43570CA12Carbonic anhydrase XIIT16987SEA
P02766TTRTransthyretinT86462SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
P22748CA4Carbonic anhydrase IVT53378SEA
P15121AKR1B1Aldose reductaseT26623SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
P08183ABCB1P-glycoprotein 1T25258SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P60568IL2Interleukin-2T61698SEA
P49763PGFPlacenta growth factorT70792SEA
Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
Q9NPH5NOX4NADPH oxidase 4T29741SEA
Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
P47989XDHXanthine dehydrogenaseT40954SEA
Q16678CYP1B1Cytochrome P450 1B1T92521SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
Q99417MYCBPMYCBP messenger RNAT37298SEA
P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
Q15717ELAVL1ELAV-like protein 1T78349SEA
Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
T29741DI0146Fibrosis[ICD-11: GA14-GC01]Q9NPH5NOX4
T40954DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]P47989XDH
T40954DI0266Mineral deficiency[ICD-11: 5B5K]P47989XDH
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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