(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid



Compound IDCDAMM01845
Common name(S)-17-Hydroxy-9,11,13,15-octadecatetraynoic acid
IUPAC name17-hydroxyoctadeca-9,11,13,15-tetraynoic acid
Molecular formulaC18H20O3

Experimental data

Retention time14.7
Adduct[M+H]+
Actual mz285.147
Theoretical mz285.148
Error3.07
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.055

Identifiers and class information

Inchi keyMTWGWIOCIREVRF-UHFFFAOYNA-N
SmilesO=C(O)CCCCCCCC#CC#CC#CC#CC(O)C
SuperclassLipids and lipid-like molecules
ClassFatty Acyls

Plant source

  • Curcuma longa 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)1
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)10
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)284.354
    Computed dipole moment(dipole)5.832
    Total solvent accessible surface area (SASA)708.841
    Hydrophobic component of SASA (FOSA)377.924
    Hydrophilic component of SASA (FISA)153.005
    Pie component of the SASA (PISA)177.912
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1135.04
    Number of hydrogen bond donors (donorHB)2
    Number of hydrogen bond acceptors (accptHB)3.7
    Free energy of solvation of dipole (dip^2/V)0.0299699
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0073819
    Globularity descriptor (glob)0.742375
    Predicted polarizability in cubic angstroms (QPpolrz)34.548
    Predicted hexadecane/gas partition coefficient (QPlogPC16)11.685
    Predicted octanol/gas partition coefficient (QPlogPoct)16.043
    Predicted water/gas partition coefficient (QPlogPw)8.044
    Predicted octanol/water partition coefficient (QPlogPo/w)4.291
    Predicted aqueous solubility (QPlogS)-6.019
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.435
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.742
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)88.829
    Predicted brain/blood partition coefficient (QPlogBB)-1.89
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)45.952
    Predicted skin permeability, log Kp (QPlogKp)-2.753
    PM3 calculated ionization potential (IP(ev))9.306
    PM3 calculated electron affinity (EA(eV))0.608
    Number of likely metabolic reactions (#metab)3
    Prediction of binding to human serum albumin (QPlogKhsa)0.288
    Predicted qualitative human oral absorption (HumanOralAbsorption)3
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)86.945
    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)72.454
    Number of nitrogen and oxygen atoms (#NandO)3
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    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
    O75899GABBR2GABA-B receptorT42446SEA
    P48066SLC6A11GABA transporter 3T38200SEA
    O75899GABBR2GABA-B receptorT42446SEA
    Q4U2R8SLC22A6Solute carrier family 22 member 6 (by homology)T70680SEA
    Q07075ENPEPAminopeptidase AT31956SEA
    P04035HMGCRHMG-CoA reductaseT53585SEA
    Q8TDS5OXER1Oxoeicosanoid receptor 1T68834SEA
    Q4U2R8SLC22A6Solute carrier family 22 member 6 (by homology)T70680SEA
    Q9UN88GABRQGABA(A) receptor thetaT15161SEA
    P78329CYP4F2Cytochrome P450 4fT82604SEA
    O60603TLR2Toll-like receptor 2T82078SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T42446DI0117Depression[ICD-11: 6A70-6A7Z]O75899GABBR2
    T42446DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]O75899GABBR2
    T42446DI0275Multiple sclerosis[ICD-11: 8A40]O75899GABBR2
    T42446DI0290Narcolepsy[ICD-11: 7A20]O75899GABBR2
    T38200DI0207Indeterminate colitis[ICD-11: DD72]P48066SLC6A11
    T42446DI0117Depression[ICD-11: 6A70-6A7Z]O75899GABBR2
    T42446DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]O75899GABBR2
    T42446DI0275Multiple sclerosis[ICD-11: 8A40]O75899GABBR2
    T42446DI0290Narcolepsy[ICD-11: 7A20]O75899GABBR2
    T70680DI0167Gout[ICD-11: FA25]Q4U2R8SLC22A6
    T70680DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q4U2R8SLC22A6
    T70680DI0310Ocular disease[ICD-11: N.A.]Q4U2R8SLC22A6
    T31956DI0190Hypertension[ICD-11: BA00-BA04]Q07075ENPEP
    T53585DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P04035HMGCR
    T53585DI0102Coronary atherosclerosis[ICD-11: BA52]P04035HMGCR
    T53585DI0128Dyslipidemia[ICD-11: 5C80-5C81]P04035HMGCR
    T53585DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P04035HMGCR
    T53585DI0275Multiple sclerosis[ICD-11: 8A40]P04035HMGCR
    T53585DI0287Myocardial infarction[ICD-11: BA41-BA43]P04035HMGCR
    T53585DI0324Pain[ICD-11: MG30-MG3Z]P04035HMGCR
    T70680DI0167Gout[ICD-11: FA25]Q4U2R8SLC22A6
    T70680DI0206Inborn purine/pyrimidine/nucleotide metabolism error[ICD-11: 5C55]Q4U2R8SLC22A6
    T70680DI0310Ocular disease[ICD-11: N.A.]Q4U2R8SLC22A6
    T82078DI0346Prostate cancer[ICD-11: 2C82]O60603TLR2

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