3\'-Angeloyloxy-4\',6\'-dihydroxy-2\',5\'-dimethoxychalcone



Compound IDCDAMM02986
Common name3\'-Angeloyloxy-4\',6\'-dihydroxy-2\',5\'-dimethoxychalcone
IUPAC name[2,4-dihydroxy-3,6-dimethoxy-5-(3-phenylprop-2-enoyl)phenyl] 2-methylbut-2-enoate
Molecular formulaC22H22O7

Experimental data

Retention time3.5
Adduct[M+K]+
Actual mz437.096
Theoretical mz437.1
Error8.83
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.488

Identifiers and class information

Inchi keyVAKBZJXPGKSDQT-BDVHTTMESA-N
SmilesO=C(OC=1C(O)=C(OC)C(O)=C(C(=O)C=CC=2C=CC=CC2)C1OC)C(=CC)C
SuperclassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids

Plant source

  • Clitoria ternatea L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)0
    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)10
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)398.412
    Computed dipole moment(dipole)6.372
    Total solvent accessible surface area (SASA)709.754
    Hydrophobic component of SASA (FOSA)333.681
    Hydrophilic component of SASA (FISA)127.695
    Pie component of the SASA (PISA)248.377
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1265.85
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)6.5
    Free energy of solvation of dipole (dip^2/V)0.0320777
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0091581
    Globularity descriptor (glob)0.797342
    Predicted polarizability in cubic angstroms (QPpolrz)40.456
    Predicted hexadecane/gas partition coefficient (QPlogPC16)12.903
    Predicted octanol/gas partition coefficient (QPlogPoct)18.464
    Predicted water/gas partition coefficient (QPlogPw)9.646
    Predicted octanol/water partition coefficient (QPlogPo/w)3.901
    Predicted aqueous solubility (QPlogS)-5.149
    Conformation-independent predicted aqueous solubility (CIQPlogS)-5.433
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.996
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)609.488
    Predicted brain/blood partition coefficient (QPlogBB)-1.378
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)289.683
    Predicted skin permeability, log Kp (QPlogKp)-2.038
    PM3 calculated ionization potential (IP(ev))9.132
    PM3 calculated electron affinity (EA(eV))0.654
    Number of likely metabolic reactions (#metab)6
    Prediction of binding to human serum albumin (QPlogKhsa)0.342
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)100
    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)109.716
    Number of nitrogen and oxygen atoms (#NandO)7
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    Number of violations of Jorgensen’s rule of three (RuleOfThree)0

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P02766TTRTransthyretinT86462SEA
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    P27338MAOBMonoamine oxidase BT83011SEA
    P14780MMP9Matrix metalloproteinase 9T54156SEA
    P13726F3Coagulation factor VII/tissue factorT72702SEA
    P08183ABCB1P-glycoprotein 1T25258SEA
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    P22001KCNA3Voltage-gated potassium channel subunit Kv1.3T76914SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P10636MAPTMicrotubule-associated protein tauT45593SEA
    Q04760GLO1Glyoxalase IT88285SEA
    P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
    Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
    Q9Y271CYSLTR1Cysteinyl leukotriene receptor 1T71192SEA
    O75884RBBP9Putative hydrolase RBBP9T12084SEA
    Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
    O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
    P32249EBI2EBV-induced G-protein coupled receptor 2T59577SEA
    P01100FOSProto-oncogene c-FosT28025SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T83011DI0115Dementia[ICD-11: 6D80-6D8Z]P27338MAOB
    T83011DI0117Depression[ICD-11: 6A70-6A7Z]P27338MAOB
    T83011DI0190Hypertension[ICD-11: BA00-BA04]P27338MAOB
    T83011DI0243Malaria[ICD-11: 1F40-1F45]P27338MAOB
    T83011DI0264Migraine[ICD-11: 8A80]P27338MAOB
    T83011DI0331Parkinsonism[ICD-11: 8A00]P27338MAOB
    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
    T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    T76914DI0198Idiopathic inflammatory myopathy[ICD-11: 4A41]P22001KCNA3
    T76914DI0351Psoriasis[ICD-11: EA90]P22001KCNA3
    T76914DI0352Psoriatic arthritis[ICD-11: FA21]P22001KCNA3
    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
    T86552DI0060Brain cancer[ICD-11: 2A00]P19438TNFRSF1A
    T86552DI0321Ovarian cancer[ICD-11: 2C73]P19438TNFRSF1A
    T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2
    T71192DI0037Asthma[ICD-11: CA23]Q9Y271CYSLTR1
    T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1

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