Verbascoside A



Compound IDCDAMM01916
Common nameVerbascoside A
IUPAC name[4,5-dihydroxy-6-[[2-(hydroxymethyl)-10-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-2-methyloxan-3-yl] 3-(4-methoxyphenyl)prop-2-enoate
Molecular formulaC31H40O16

Experimental data

Retention time10.33
Adduct[M+H]+
Actual mz669.237
Theoretical mz669.239
Error3.25
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9856

Identifiers and class information

Inchi keyRTCISXKUWWQSRF-CFOQIUDMNA-N
SmilesO=C(OC1C(O)C(O)C(OC1C)OC2C3OC3(CO)C4C(OC=CC24)OC5OC(CO)C(O)C(O)C5O)C=CC6=CC=C(OC)C=C6
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Plant source

  • Curcuma longa L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)8
    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)18
    Number of reactive functional groups (#rtvFG)5
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)668.647
    Computed dipole moment(dipole)6.401
    Total solvent accessible surface area (SASA)948.903
    Hydrophobic component of SASA (FOSA)426.61
    Hydrophilic component of SASA (FISA)287.118
    Pie component of the SASA (PISA)235.175
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1835.5
    Number of hydrogen bond donors (donorHB)6
    Number of hydrogen bond acceptors (accptHB)24.15
    Free energy of solvation of dipole (dip^2/V)0.0223255
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0623406
    Globularity descriptor (glob)0.764033
    Predicted polarizability in cubic angstroms (QPpolrz)57.991
    Predicted hexadecane/gas partition coefficient (QPlogPC16)20.476
    Predicted octanol/gas partition coefficient (QPlogPoct)41.812
    Predicted water/gas partition coefficient (QPlogPw)34.16
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.237
    Predicted aqueous solubility (QPlogS)-2.446
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.468
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.472
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)18.757
    Predicted brain/blood partition coefficient (QPlogBB)-3.8
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)6.727
    Predicted skin permeability, log Kp (QPlogKp)-4.254
    PM3 calculated ionization potential (IP(ev))9.134
    PM3 calculated electron affinity (EA(eV))0.815
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)-1.682
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)3.615
    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)240.042
    Number of nitrogen and oxygen atoms (#NandO)16
    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
    P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P60568IL2Interleukin-2T61698SEA
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
    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
    T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
    T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
    T20761DI0095Colorectal cancer[ICD-11: 2B91]P15692VEGFA
    T20761DI0365Retinopathy[ICD-11: 9B71]P15692VEGFA
    T20761DI0430Vascular system developmental anomaly[ICD-11: LA90]P15692VEGFA
    T18639DI0081Chronic arterial occlusive disease[ICD-11: BD4Z]P05230FGF1
    T18639DI0102Coronary atherosclerosis[ICD-11: BA52]P05230FGF1
    T31621DI0005Acne vulgaris[ICD-11: ED80]P09038FGF2
    T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
    T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
    T72038DI0190Hypertension[ICD-11: BA00-BA04]P17931LGALS3
    T72038DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P17931LGALS3
    T72038DI0252Melanoma[ICD-11: 2C30]P17931LGALS3
    T72038DI0302Non-alcoholic fatty liver disease[ICD-11: DB92]P17931LGALS3
    T72038DI0351Psoriasis[ICD-11: EA90]P17931LGALS3
    T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
    T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T37298DI0235Liver cancer[ICD-11: 2C12]Q99417MYCBP

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