(1R,2R,3E,7E,11R,12S)-2, 18-O-diacetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18 -triol



Compound IDCDAMM01940
Common name(1R,2R,3E,7E,11R,12S)-2, 18-O-diacetyl-16-O-(3-hydroxy-3-methylglutaryl)-dolabella-3,7-dien-2,16,18 -triol
IUPAC name5-[[4-acetyloxy-1-(2-acetyloxypropan-2-yl)-3a,10-dimethyl-2,3,4,7,8,11,12,12a-octahydro-1H-cyclopenta[11]annulen-6-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
Molecular formulaC30H46O9

Experimental data

Retention time19.47
Adduct[M+H]+
Actual mz551.318
Theoretical mz551.321
Error5.4
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.3967

Identifiers and class information

Inchi keyATABDKOENHIVSH-OOYBWIPCSA-N
SmilesO=C(OC1C=C(COC(=O)CC(O)(C)CC(=O)O)CCC=C(C)CCC2C(CCC12C)C(OC(=O)C)(C)C)C
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Plant source

  • Curcuma longa L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)2
    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)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)550.688
    Computed dipole moment(dipole)6.605
    Total solvent accessible surface area (SASA)814.623
    Hydrophobic component of SASA (FOSA)619.223
    Hydrophilic component of SASA (FISA)186.604
    Pie component of the SASA (PISA)8.796
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1673.47
    Number of hydrogen bond donors (donorHB)1
    Number of hydrogen bond acceptors (accptHB)7.75
    Free energy of solvation of dipole (dip^2/V)0.0260713
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0095136
    Globularity descriptor (glob)0.836798
    Predicted polarizability in cubic angstroms (QPpolrz)54.481
    Predicted hexadecane/gas partition coefficient (QPlogPC16)15.085
    Predicted octanol/gas partition coefficient (QPlogPoct)24.23
    Predicted water/gas partition coefficient (QPlogPw)9.901
    Predicted octanol/water partition coefficient (QPlogPo/w)5.795
    Predicted aqueous solubility (QPlogS)-6.518
    Conformation-independent predicted aqueous solubility (CIQPlogS)-6.964
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.407
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)42.652
    Predicted brain/blood partition coefficient (QPlogBB)-1.816
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)20.793
    Predicted skin permeability, log Kp (QPlogKp)-3.968
    PM3 calculated ionization potential (IP(ev))9.542
    PM3 calculated electron affinity (EA(eV))-0.526
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)1.045
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)64.133
    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)161.783
    Number of nitrogen and oxygen atoms (#NandO)9
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    Number of violations of Jorgensen’s rule of three (RuleOfThree)2

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P04035HMGCRHMG-CoA reductaseT53585SwissTargetPrediction

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    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

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