Guibourtinidol-(4alpha->6)-fisetinidol



Compound IDCDAMM00627
Common nameGuibourtinidol-(4alpha->6)-fisetinidol
IUPAC name6-[3,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-4-yl]-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,7-diol
Molecular formulaC30H26O9

Experimental data

Retention time12.75
Adduct[M+H]+
Actual mz531.164
Theoretical mz531.165
Error1.65
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8554

Identifiers and class information

Inchi keyFPHINTVIWMLKSF-QRHJZVIPNA-N
SmilesOC1=CC=C(C=C1)C2OC3=CC(O)=CC=C3C(C=4C=C5C(OC(C6=CC=C(O)C(O)=C6)C(O)C5)=CC4O)C2O
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)4
    Number of non-conjugated amine groups (#amine)0
    Number of amidine and guanidine groups (#amidine)0
    Number of carboxylic acid groups (#acid)0
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)7
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)530.53
    Computed dipole moment(dipole)1.24
    Total solvent accessible surface area (SASA)824.407
    Hydrophobic component of SASA (FOSA)97.481
    Hydrophilic component of SASA (FISA)314.725
    Pie component of the SASA (PISA)412.202
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1522.55
    Number of hydrogen bond donors (donorHB)7
    Number of hydrogen bond acceptors (accptHB)8.65
    Free energy of solvation of dipole (dip^2/V)0.0010096
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0277602
    Globularity descriptor (glob)0.776374
    Predicted polarizability in cubic angstroms (QPpolrz)54.22
    Predicted hexadecane/gas partition coefficient (QPlogPC16)19.231
    Predicted octanol/gas partition coefficient (QPlogPoct)34.022
    Predicted water/gas partition coefficient (QPlogPw)23.876
    Predicted octanol/water partition coefficient (QPlogPo/w)2.452
    Predicted aqueous solubility (QPlogS)-6.135
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.473
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.116
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)10.265
    Predicted brain/blood partition coefficient (QPlogBB)-3.339
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)3.506
    Predicted skin permeability, log Kp (QPlogKp)-5.196
    PM3 calculated ionization potential (IP(ev))8.809
    PM3 calculated electron affinity (EA(eV))-0.076
    Number of likely metabolic reactions (#metab)11
    Prediction of binding to human serum albumin (QPlogKhsa)0.337
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)33.488
    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)164.023
    Number of nitrogen and oxygen atoms (#NandO)9
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    Number of violations of Jorgensen’s rule of three (RuleOfThree)3

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
    P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction
    P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
    Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
    Q92731ESR2Estrogen receptor betaT80896SEA
    P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
    P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
    P03372ESR1Estrogen receptor alphaT02506SEA
    P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
    P20151KLK2Kallikrein 2T01908SEA
    P15692VEGFAVascular endothelial growth factor AT20761SwissTargetPrediction and SEA
    P49763PGFPlacenta growth factorT70792SwissTargetPrediction and SEA
    P52209PGD6-phosphogluconate dehydrogenaseT76497SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA

    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
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
    T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
    T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
    T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
    T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
    T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
    T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
    T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
    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
    T60529DI0141Eye anterior segment structural developmental anomaly[ICD-11: LA11]Q5T7T8COX1
    T60529DI0145Female pelvic pain[ICD-11: GA34]Q5T7T8COX1
    T60529DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q5T7T8COX1
    T60529DI0207Indeterminate colitis[ICD-11: DD72]Q5T7T8COX1
    T60529DI0306Nutritional deficiency[ICD-11: 5B50-5B71]Q5T7T8COX1
    T60529DI0320Osteoarthritis[ICD-11: FA00-FA05]Q5T7T8COX1
    T60529DI0324Pain[ICD-11: MG30-MG3Z]Q5T7T8COX1
    T60529DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q5T7T8COX1
    T60529DI0366Rheumatoid arthritis[ICD-11: FA20]Q5T7T8COX1
    T60529DI0372Seborrhoeic dermatitis[ICD-11: EA81]Q5T7T8COX1
    T60529DI0416Tuberculosis[ICD-11: 1B10-1B12]Q5T7T8COX1
    T60529DI0419Ulcerative colitis[ICD-11: DD71]Q5T7T8COX1
    T80896DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q92731ESR2
    T80896DI0108Cushing syndrome[ICD-11: 5A70]Q92731ESR2
    T80896DI0254Menopausal disorder[ICD-11: GA30]Q92731ESR2
    T80896DI0432Vasomotor/allergic rhinitis[ICD-11: CA08]Q92731ESR2
    T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
    T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
    T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
    T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
    T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
    T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
    T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
    T01908DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]P20151KLK2
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T70792DI0095Colorectal cancer[ICD-11: 2B91]P49763PGF
    T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1

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