Luteolin 7-[E-feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 4\'-glucuronide



Compound IDCDAMM01920
Common nameLuteolin 7-[E-feruloyl-(->2)-glucuronyl-(1->2)-glucuronide] 4\'-glucuronide
IUPAC name6-[4-[7-[6-carboxy-3-[6-carboxy-4,5-dihydroxy-3-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxy]oxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-5-hydroxy-4-oxochromen-2-yl]-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular formulaC43H42O27

Experimental data

Retention time19.44
Adduct[M+2H]2+
Actual mz496.106
Theoretical mz496.103
Error5.89
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.6196

Identifiers and class information

Inchi keySPAFPIYZLSWKDV-XVNBXDOJNA-N
SmilesO=C(O)C1OC(OC=2C=CC(=CC2O)C=3OC4=CC(OC5OC(C(=O)O)C(O)C(O)C5OC6OC(C(=O)O)C(O)C(O)C6OC(=O)C=CC7=CC=C(O)C(OC)=C7)=CC(O)=C4C(=O)C3)C(O)C(O)C1O
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Curcuma longa L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)16
    Number of non-conjugated amine groups (#amine)0
    Number of amidine and guanidine groups (#amidine)0
    Number of carboxylic acid groups (#acid)3
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)24
    Number of reactive functional groups (#rtvFG)4
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)990.789
    Computed dipole moment(dipole)12.118
    Total solvent accessible surface area (SASA)1275.61
    Hydrophobic component of SASA (FOSA)259.475
    Hydrophilic component of SASA (FISA)721.402
    Pie component of the SASA (PISA)294.738
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)2505.41
    Number of hydrogen bond donors (donorHB)9
    Number of hydrogen bond acceptors (accptHB)29.7
    Free energy of solvation of dipole (dip^2/V)0.0586079
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0698486
    Globularity descriptor (glob)0.699355
    Predicted polarizability in cubic angstroms (QPpolrz)81.517
    Predicted hexadecane/gas partition coefficient (QPlogPC16)31.64
    Predicted octanol/gas partition coefficient (QPlogPoct)59.78
    Predicted water/gas partition coefficient (QPlogPw)46.842
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.525
    Predicted aqueous solubility (QPlogS)-4.3
    Conformation-independent predicted aqueous solubility (CIQPlogS)-8.116
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.38
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0
    Predicted brain/blood partition coefficient (QPlogBB)-10.716
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0
    Predicted skin permeability, log Kp (QPlogKp)-11.472
    PM3 calculated ionization potential (IP(ev))9.002
    PM3 calculated electron affinity (EA(eV))0.973
    Number of likely metabolic reactions (#metab)14
    Prediction of binding to human serum albumin (QPlogKhsa)-2.189
    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)474.258
    Number of nitrogen and oxygen atoms (#NandO)27
    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
    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
    P60568IL2Interleukin-2T61698SEA
    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
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
    Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    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
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    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
    T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3

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