2\',6\'-Dihydroxy-3\'-(1-p-menthen-3-yl)-4\'-methoxychalcone



Compound IDCDAMM02921
Common name2\',6\'-Dihydroxy-3\'-(1-p-menthen-3-yl)-4\'-methoxychalcone
IUPAC name1-[2,6-dihydroxy-4-methoxy-3-(3-methyl-6-propan-2-ylcyclohex-2-en-1-yl)phenyl]-3-phenylprop-2-en-1-one
Molecular formulaC26H30O4

Experimental data

Retention time0.57
Adduct[M+H]+
Actual mz407.219
Theoretical mz407.221
Error5.1
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0646

Identifiers and class information

Inchi keyHFZKMAAAZSRYAY-ACCUITESNA-N
SmilesO=C(C=CC=1C=CC=CC1)C2=C(O)C=C(OC)C(=C2O)C3C=C(C)CCC3C(C)C
SuperclassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids

Plant source

  • Clitoria ternatea L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)3
    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)8
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)-1
    Molecular weight (mol_MW)406.521
    Computed dipole moment(dipole)5.644
    Total solvent accessible surface area (SASA)744.864
    Hydrophobic component of SASA (FOSA)378.365
    Hydrophilic component of SASA (FISA)92.588
    Pie component of the SASA (PISA)273.911
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1363.44
    Number of hydrogen bond donors (donorHB)0
    Number of hydrogen bond acceptors (accptHB)2.25
    Free energy of solvation of dipole (dip^2/V)0.0233672
    Index of cohesive interaction in solids (ACxDN^.5/SA)0
    Globularity descriptor (glob)0.798324
    Predicted polarizability in cubic angstroms (QPpolrz)45.89
    Predicted hexadecane/gas partition coefficient (QPlogPC16)13.52
    Predicted octanol/gas partition coefficient (QPlogPoct)16.47
    Predicted water/gas partition coefficient (QPlogPw)4.456
    Predicted octanol/water partition coefficient (QPlogPo/w)6.774
    Predicted aqueous solubility (QPlogS)-7.852
    Conformation-independent predicted aqueous solubility (CIQPlogS)-7.482
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.102
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1311.85
    Predicted brain/blood partition coefficient (QPlogBB)-0.887
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)663.39
    Predicted skin permeability, log Kp (QPlogKp)-1.493
    PM3 calculated ionization potential (IP(ev))9.089
    PM3 calculated electron affinity (EA(eV))0.502
    Number of likely metabolic reactions (#metab)6
    Prediction of binding to human serum albumin (QPlogKhsa)1.635
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    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)66.425
    Number of nitrogen and oxygen atoms (#NandO)4
    Number of violations of Lipinski’s rule of five (RuleOfFive)1
    Number of violations of Jorgensen’s rule of three (RuleOfThree)1

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P35228NOS2Nitric oxide synthase, inducibleT02703SwissTargetPrediction
    P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction and SEA
    P27338MAOBMonoamine oxidase BT83011SEA
    Q15118PDK1Pyruvate dehydrogenase kinase isoform 1T20891SwissTargetPrediction
    P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
    Q5T7T8COX1Prostaglandin G/H synthase 1T60529SwissTargetPrediction
    P11926ODC1Ornithine decarboxylaseT60366SEA
    O14684PTGESProstaglandin E synthaseT02562SwissTargetPrediction
    P09917ALOX5Arachidonate 5-lipoxygenaseT00140SwissTargetPrediction
    P08183ABCB1P-glycoprotein 1T25258SwissTargetPrediction and SEA
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
    P07711CTSLCathepsin LT98691SwissTargetPrediction
    P10276RARARetinoic acid receptor alphaT94085SwissTargetPrediction
    O15111CHUKInhibitor of NF-kappa-B kinase (IKK)T78429SwissTargetPrediction
    P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SwissTargetPrediction and SEA
    P22001KCNA3Voltage-gated potassium channel subunit Kv1.3T76914SwissTargetPrediction and SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    P10636MAPTMicrotubule-associated protein tauT45593SEA
    Q04760GLO1Glyoxalase IT88285SEA
    P19438TNFRSF1ATumor necrosis factor receptor R1T86552SEA
    Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
    Q9H4B7TUBB1Tubulin beta-1 chainT84397SEA
    O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T02703DI0083Chronic kidney disease[ICD-11: GB61]P35228NOS2
    T02703DI0320Osteoarthritis[ICD-11: FA00-FA05]P35228NOS2
    T02703DI0375Sepsis[ICD-11: 1G40-1G41]P35228NOS2
    T02703DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35228NOS2
    T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
    T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
    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
    T20891DI0241Lymphoma[ICD-11: 2A80-2A86]Q15118PDK1
    T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
    T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
    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
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T02562DI0025Alzheimer disease[ICD-11: 8A20]O14684PTGES
    T00140DI0037Asthma[ICD-11: CA23]P09917ALOX5
    T00140DI0147Filariasis[ICD-11: 1F66]P09917ALOX5
    T00140DI0403Thrombocytopenia[ICD-11: 3B64]P09917ALOX5
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
    T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
    T94085DI0025Alzheimer disease[ICD-11: 8A20]P10276RARA
    T94085DI0251Mature T-cell lymphoma[ICD-11: 2A90]P10276RARA
    T78429DI0250Mature B-cell lymphoma[ICD-11: 2A85]O15111CHUK
    T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
    T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
    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
    T84397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H4B7TUBB1

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