3-Hydroxy-beta-ionone



Compound IDCDAMM00258
Common name3-Hydroxy-beta-ionone
IUPAC name(E)-4-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one
Molecular formulaC13H20O2

Experimental data

Retention time61.007
Adduct[M+H]+
Actual mz209.154
Theoretical mz209.154
Error1.88
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7

Identifiers and class information

Inchi keyCJDRUOGAGYHKKD-RQBLFBSQSA-N
SmilesCC1=C(C(CC(C1)O)(C)C)C=CC(=O)C
SuperclassAlkaloids and derivatives
ClassAjmaline-sarpagine alkaloids

Plant source

  • Tribulus terrestris 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)4
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)0
    Molecular weight (mol_MW)208.3
    Computed dipole moment(dipole)4.132
    Total solvent accessible surface area (SASA)472.807
    Hydrophobic component of SASA (FOSA)369.838
    Hydrophilic component of SASA (FISA)98.445
    Pie component of the SASA (PISA)4.523
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)805.221
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)3.7
    Free energy of solvation of dipole (dip^2/V)0.0211998
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0078256
    Globularity descriptor (glob)0.885303
    Predicted polarizability in cubic angstroms (QPpolrz)23.546
    Predicted hexadecane/gas partition coefficient (QPlogPC16)6.724
    Predicted octanol/gas partition coefficient (QPlogPoct)10.726
    Predicted water/gas partition coefficient (QPlogPw)5.784
    Predicted octanol/water partition coefficient (QPlogPo/w)2.118
    Predicted aqueous solubility (QPlogS)-2.969
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.111
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.409
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1154.36
    Predicted brain/blood partition coefficient (QPlogBB)-0.515
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)577.744
    Predicted skin permeability, log Kp (QPlogKp)-2.934
    PM3 calculated ionization potential (IP(ev))9.519
    PM3 calculated electron affinity (EA(eV))0.409
    Number of likely metabolic reactions (#metab)3
    Prediction of binding to human serum albumin (QPlogKhsa)-0.049
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)94.155
    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)51.595
    Number of nitrogen and oxygen atoms (#NandO)2
    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
    P10276RARARetinoic acid receptor alphaT94085SEA
    P19793RXRARetinoid X receptor alpha (by homology)T13726SEA
    P02753RBP4Plasma retinol-binding proteinT55703SEA
    P28702RXRBRetinoid X receptor betaT60077SEA
    P13631RARGRetinoic acid receptor gammaT82146SEA
    P48443RXRGRetinoid X receptor gammaT46456SEA
    P10826RARBRetinoic acid receptor betaT61657SEA
    Q9UJM8HAO1Hydroxyacid oxidase 1T63170SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T94085DI0025Alzheimer disease[ICD-11: 8A20]P10276RARA
    T94085DI0251Mature T-cell lymphoma[ICD-11: 2A90]P10276RARA
    T13726DI0225Kaposi sarcoma[ICD-11: 2B57]P19793RXRA
    T13726DI0283Mycosis fungoides[ICD-11: 2B01]P19793RXRA
    T55703DI0212Inherited retinal dystrophy[ICD-11: 9B70]P02753RBP4
    T60077DI0225Kaposi sarcoma[ICD-11: 2B57]P28702RXRB
    T82146DI0005Acne vulgaris[ICD-11: ED80]P13631RARG
    T82146DI0012Acute myeloid leukaemia[ICD-11: 2A60]P13631RARG
    T82146DI0225Kaposi sarcoma[ICD-11: 2B57]P13631RARG
    T82146DI0277Muscle calcification/ossification[ICD-11: FB31]P13631RARG
    T82146DI0351Psoriasis[ICD-11: EA90]P13631RARG
    T46456DI0225Kaposi sarcoma[ICD-11: 2B57]P48443RXRG
    T46456DI0232Light sensitivity impairment[ICD-11: 9D45]P48443RXRG
    T61657DI0225Kaposi sarcoma[ICD-11: 2B57]P10826RARB
    T63170DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]Q9UJM8HAO1

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