1-O-(E)-Caffeoyl-4,6-(S)-HHDP-beta-D-glucopyranose



Compound IDCDAMM01934
Common name1-O-(E)-Caffeoyl-4,6-(S)-HHDP-beta-D-glucopyranose
IUPAC name[6-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-4,5-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Molecular formulaC29H26O17

Experimental data

Retention time19.46
Adduct[M+K]+
Actual mz685.084
Theoretical mz685.08
Error5.9
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.6961

Identifiers and class information

Inchi keyYSKBQCUOPDXDNF-IGLHONHCNA-N
SmilesO=C(OC1OC(COC(=O)C2=CC(O)=C(O)C(O)=C2)C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(O)C1O)C=CC4=CC=C(O)C(O)=C4
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Plant source

  • Curcuma longa L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)9
    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)19
    Number of reactive functional groups (#rtvFG)4
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)646.514
    Computed dipole moment(dipole)10.471
    Total solvent accessible surface area (SASA)961.019
    Hydrophobic component of SASA (FOSA)91.219
    Hydrophilic component of SASA (FISA)585.128
    Pie component of the SASA (PISA)284.672
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1763.11
    Number of hydrogen bond donors (donorHB)10
    Number of hydrogen bond acceptors (accptHB)17.1
    Free energy of solvation of dipole (dip^2/V)0.0621859
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0562683
    Globularity descriptor (glob)0.734433
    Predicted polarizability in cubic angstroms (QPpolrz)54.924
    Predicted hexadecane/gas partition coefficient (QPlogPC16)23.548
    Predicted octanol/gas partition coefficient (QPlogPoct)44.605
    Predicted water/gas partition coefficient (QPlogPw)35.247
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.749
    Predicted aqueous solubility (QPlogS)-3.99
    Conformation-independent predicted aqueous solubility (CIQPlogS)-5.977
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-7.187
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.028
    Predicted brain/blood partition coefficient (QPlogBB)-7.814
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.006
    Predicted skin permeability, log Kp (QPlogKp)-9.476
    PM3 calculated ionization potential (IP(ev))9.065
    PM3 calculated electron affinity (EA(eV))0.96
    Number of likely metabolic reactions (#metab)10
    Prediction of binding to human serum albumin (QPlogKhsa)-1.052
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
    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)327.097
    Number of nitrogen and oxygen atoms (#NandO)17
    Number of violations of Lipinski’s rule of five (RuleOfFive)3
    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
    O43570CA12Carbonic anhydrase XIIT16987SEA
    P02766TTRTransthyretinT86462SEA
    P43166CA7Carbonic anhydrase VIIT37541SEA
    P23280CA6Carbonic anhydrase VIT06569SEA
    P15121AKR1B1Aldose reductaseT26623SEA
    P05121SERPINE1Plasminogen activator inhibitor-1T15556SEA
    Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
    P52209PGD6-phosphogluconate dehydrogenaseT76497SEA
    Q04760GLO1Glyoxalase IT88285SEA
    O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
    P10809HSPD1Mitochondrial matrix protein P1T11283SEA
    Q99417MYCBPMYCBP messenger RNAT37298SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T86462DI0026Amyloidosis[ICD-11: 5D00]P02766TTR
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
    T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
    T15556DI0037Asthma[ICD-11: CA23]P05121SERPINE1
    T15556DI0405Thrombosis[ICD-11: DB61-GB90]P05121SERPINE1
    T76497DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P52209PGD
    T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
    T11283DI0120Diabetes mellitus[ICD-11: 5A10]P10809HSPD1
    T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP

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