Calabaxanthone



Compound IDCDAMM02920
Common nameCalabaxanthone
IUPAC name5-hydroxy-8-methoxy-2,2-dimethyl-7-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one
Molecular formulaC24H24O5

Experimental data

Retention time10.62
Adduct[M+H]+
Actual mz393.17
Theoretical mz393.169
Error0.82
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2857

Identifiers and class information

Inchi keyPLKQPRRVFTZBAE-UHFFFAOYSA-N
SmilesO=C1C2=C(OC3=CC=C(OC)C(=C31)CC=C(C)C)C=C4OC(C=CC4=C2O)(C)C
SuperclassOrganoheterocyclic compounds
ClassBenzopyrans

Plant source

  • Clitoria ternatea L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)1
    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)4
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)0
    Molecular weight (mol_MW)392.451
    Computed dipole moment(dipole)3.291
    Total solvent accessible surface area (SASA)681.874
    Hydrophobic component of SASA (FOSA)421.415
    Hydrophilic component of SASA (FISA)43.347
    Pie component of the SASA (PISA)217.112
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1238.86
    Number of hydrogen bond donors (donorHB)0
    Number of hydrogen bond acceptors (accptHB)3.75
    Free energy of solvation of dipole (dip^2/V)0.0087407
    Index of cohesive interaction in solids (ACxDN^.5/SA)0
    Globularity descriptor (glob)0.818103
    Predicted polarizability in cubic angstroms (QPpolrz)42.93
    Predicted hexadecane/gas partition coefficient (QPlogPC16)11.569
    Predicted octanol/gas partition coefficient (QPlogPoct)15.884
    Predicted water/gas partition coefficient (QPlogPw)5.943
    Predicted octanol/water partition coefficient (QPlogPo/w)5.505
    Predicted aqueous solubility (QPlogS)-6.524
    Conformation-independent predicted aqueous solubility (CIQPlogS)-6.682
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.511
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)3844.53
    Predicted brain/blood partition coefficient (QPlogBB)-0.109
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2120.78
    Predicted skin permeability, log Kp (QPlogKp)-1.17
    PM3 calculated ionization potential (IP(ev))8.778
    PM3 calculated electron affinity (EA(eV))0.624
    Number of likely metabolic reactions (#metab)5
    Prediction of binding to human serum albumin (QPlogKhsa)1.041
    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)63.767
    Number of nitrogen and oxygen atoms (#NandO)5
    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
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P11926ODC1Ornithine decarboxylaseT60366SEA
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SEA
    P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
    P10276RARARetinoic acid receptor alphaT94085SwissTargetPrediction and SEA
    O14980XPO1Exportin-1T51407SEA
    Q9UNQ0ABCG2ATP-binding cassette sub-family G member 2T56556SEA
    Q16678CYP1B1Cytochrome P450 1B1T92521SEA
    O60911CTSVCathepsin (V and K)T93653SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
    T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
    T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
    T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
    T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
    T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
    T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
    T94085DI0025Alzheimer disease[ICD-11: 8A20]P10276RARA
    T94085DI0251Mature T-cell lymphoma[ICD-11: 2A90]P10276RARA
    T51407DI0234Liposarcoma[ICD-11: 2B59]O14980XPO1
    T51407DI0274Multiple myeloma[ICD-11: 2A83]O14980XPO1
    T51407DI0395Stomach cancer[ICD-11: 2B72]O14980XPO1
    T56556DI0218Irritable bowel syndrome[ICD-11: DD91]Q9UNQ0ABCG2
    T56556DI0366Rheumatoid arthritis[ICD-11: FA20]Q9UNQ0ABCG2
    T93653DI0055Bone cancer[ICD-11: 2B5Z]O60911CTSV
    T93653DI0087Chronic pain[ICD-11: MG30]O60911CTSV

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