Volkensiflavone



Compound IDCDAMM00635
Common nameVolkensiflavone
IUPAC name8-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
Molecular formulaC30H20O10

Experimental data

Retention time3.92
Adduct[M+H]+
Actual mz541.116
Theoretical mz541.113
Error4.85
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8868

Identifiers and class information

Inchi keyYOGANETYFUQWIM-WJVWOHFINA-N
SmilesO=C1C=C(OC=2C1=C(O)C=C(O)C2C3C(=O)C=4C(O)=CC(O)=CC4OC3C5=CC=C(O)C=C5)C=6C=CC(O)=CC6
SuperclassPhenylpropanoids and polyketides
ClassFlavonoids

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)2
    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)6
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)540.482
    Computed dipole moment(dipole)7.403
    Total solvent accessible surface area (SASA)730.18
    Hydrophobic component of SASA (FOSA)11.805
    Hydrophilic component of SASA (FISA)351.662
    Pie component of the SASA (PISA)366.713
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1406.29
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)7.75
    Free energy of solvation of dipole (dip^2/V)0.0389715
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0212276
    Globularity descriptor (glob)0.83135
    Predicted polarizability in cubic angstroms (QPpolrz)49.775
    Predicted hexadecane/gas partition coefficient (QPlogPC16)17.199
    Predicted octanol/gas partition coefficient (QPlogPoct)28.498
    Predicted water/gas partition coefficient (QPlogPw)18.531
    Predicted octanol/water partition coefficient (QPlogPo/w)2.433
    Predicted aqueous solubility (QPlogS)-5.535
    Conformation-independent predicted aqueous solubility (CIQPlogS)-8.624
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.01
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)4.582
    Predicted brain/blood partition coefficient (QPlogBB)-3.19
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.466
    Predicted skin permeability, log Kp (QPlogKp)-6.133
    PM3 calculated ionization potential (IP(ev))9.078
    PM3 calculated electron affinity (EA(eV))0.682
    Number of likely metabolic reactions (#metab)8
    Prediction of binding to human serum albumin (QPlogKhsa)0.554
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)27.107
    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)187.395
    Number of nitrogen and oxygen atoms (#NandO)10
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    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
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P22748CA4Carbonic anhydrase IVT53378SEA
    P24864CCNE1Cyclin-dependent kinase 2/cyclin E1T10052SEA
    P05164MPOMyeloperoxidaseT23471SEA
    Q92731ESR2Estrogen receptor betaT80896SEA
    P03372ESR1Estrogen receptor alphaT02506SEA
    P33527ABCC1Multidrug resistance-associated protein 1T11288SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    O95271TNKSTankyrase-1T83059SEA
    P24941CDK2Cyclin-dependent kinase 2T70176SEA
    Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SEA
    P24385CCND1Cyclin-dependent kinase 4/cyclin D1T12355SEA
    P20151KLK2Kallikrein 2T01908SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    Q07002CDK18Serine/threonine-protein kinase PCTAIRE-3T27577SEA
    P60568IL2Interleukin-2T61698SEA
    P49763PGFPlacenta growth factorT70792SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    Q9NPH5NOX4NADPH oxidase 4T29741SEA
    P47989XDHXanthine dehydrogenaseT40954SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    Q04760GLO1Glyoxalase IT88285SEA
    P20248CCNA2CDK2/Cyclin AT58470SEA
    Q14004CDK13Cyclin-dependent kinase 13T74839SEA
    Q16512PKN1Protein kinase N1T60003SEA
    Q9HC98NEK6Serine/threonine-protein kinase NEK6T78992SEA
    P16152CBR1Carbonyl reductase [NADPH] 1T70518SEA
    Q13564NAE1NEDD8-activating enzyme E1 regulatory subunitT01447SEA
    Q13332PTPRSReceptor-type tyrosine-protein phosphatase ST10147SEA
    Q8N5S9CAMKK1CaM-kinase kinase alphaT38134SEA
    Q09013DMPKMyotonin-protein kinaseT68766SEA
    P21860ERBB3Receptor tyrosine-protein kinase erbB-3T86350SEA
    Q13705ACVR2BActivin receptor type-2BT80338SEA
    Q99417MYCBPMYCBP messenger RNAT37298SEA
    P16220CREB1Cyclic AMP-responsive element-binding proteinT92098SEA
    Q15717ELAVL1ELAV-like protein 1T78349SEA
    Q96HK3CALMCalmodulinT39610SEA
    Q9UK17KCND3Voltage-gated potassium channel Kv4.3T74500SEA
    P27037ACVR2AActivin receptor type IIAT47366SEA
    P14635CCNB1G2/mitotic-specific cyclin B1T98459SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T23471DI0229Left ventricular failure[ICD-11: BD11]P05164MPO
    T23471DI0339Postoperative inflammation[ICD-11: 1A00-CA43]P05164MPO
    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
    T02506DI0106COVID-19[ICD-11: 1D6Y]P03372ESR1
    T11288DI0167Gout[ICD-11: FA25]P33527ABCC1
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    T83059DI0060Brain cancer[ICD-11: 2A00]O95271TNKS
    T83059DI0062Breast cancer[ICD-11: 2C60-2C6Y]O95271TNKS
    T83059DI0321Ovarian cancer[ICD-11: 2C73]O95271TNKS
    T83059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]O95271TNKS
    T70176DI0060Brain cancer[ICD-11: 2A00]P24941CDK2
    T70176DI0062Breast cancer[ICD-11: 2C60-2C6Y]P24941CDK2
    T70176DI0238Lung cancer[ICD-11: 2C25]P24941CDK2
    T70176DI0241Lymphoma[ICD-11: 2A80-2A86]P24941CDK2
    T70176DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P24941CDK2
    T70176DI0303Non-small-cell lung cancer[ICD-11: 2C25]P24941CDK2
    T70176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P24941CDK2
    T70176DI0406Thymoma[ICD-11: 2C27]P24941CDK2
    T12355DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P24385CCND1
    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
    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
    T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
    T58470DI0363Retina cancer[ICD-11: 2D02]P20248CCNA2
    T74839DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q14004CDK13
    T70518DI0037Asthma[ICD-11: CA23]P16152CBR1
    T01447DI0284Myelodysplastic syndrome[ICD-11: 2A37]Q13564NAE1
    T10147DI0057Bone paget disease[ICD-11: FB85]Q13332PTPRS
    T68766DI0288Myotonic disorder[ICD-11: 8C71]Q09013DMPK
    T86350DI0062Breast cancer[ICD-11: 2C60-2C6Y]P21860ERBB3
    T86350DI0095Colorectal cancer[ICD-11: 2B91]P21860ERBB3
    T86350DI0172Head and neck cancer[ICD-11: 2D42]P21860ERBB3
    T86350DI0238Lung cancer[ICD-11: 2C25]P21860ERBB3
    T86350DI0246Malignant mesenchymal neoplasm[ICD-11: 2B5D-2B5Y]P21860ERBB3
    T86350DI0259Metastatic lymph node neoplasm[ICD-11: 2D60]P21860ERBB3
    T86350DI0326Pancreatic cancer[ICD-11: 2C10]P21860ERBB3
    T86350DI0351Psoriasis[ICD-11: EA90]P21860ERBB3
    T86350DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P21860ERBB3
    T86350DI0393Squamous cell carcinoma[ICD-11: 2B60-2D01]P21860ERBB3
    T80338DI0295Nervous system paraneoplastic/autoimmune disorder[ICD-11: 8E4A]Q13705ACVR2B
    T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP
    T39610DI0068Cardiac arrhythmia[ICD-11: BC9Z]Q96HK3CALM
    T39610DI0243Malaria[ICD-11: 1F40-1F45]Q96HK3CALM
    T39610DI0370Schizophrenia[ICD-11: 6A20]Q96HK3CALM
    T74500DI0004Acidosis[ICD-11: 5C73]Q9UK17KCND3
    T47366DI0012Acute myeloid leukaemia[ICD-11: 2A60]P27037ACVR2A
    T47366DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P27037ACVR2A

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