6-O-alpha-D-Galactopyranosylharpagoside



Compound IDCDAMM02974
Common name6-O-alpha-D-Galactopyranosylharpagoside
IUPAC name[4a-hydroxy-7-methyl-1,5-bis[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]-1,5,6,7a-tetrahydrocyclopenta[c]pyran-7-yl] 3-phenylprop-2-enoate
Molecular formulaC30H40O16

Experimental data

Retention time4.17
Adduct[M+H]+
Actual mz657.246
Theoretical mz657.239
Error9.77
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.4833

Identifiers and class information

Inchi keyWPZQAEXTOYWVAN-STMODJOINA-N
SmilesO=C(OC1(C)CC(OC2OC(CO)C(O)C(O)C2O)C3(O)C=COC(OC4OC(CO)C(O)C(O)C4O)C31)C=CC=5C=CC=CC5
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

Plant source

  • Clitoria ternatea L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)10
    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)656.636
    Computed dipole moment(dipole)2.193
    Total solvent accessible surface area (SASA)851.191
    Hydrophobic component of SASA (FOSA)264.781
    Hydrophilic component of SASA (FISA)310.361
    Pie component of the SASA (PISA)276.049
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1739.56
    Number of hydrogen bond donors (donorHB)9
    Number of hydrogen bond acceptors (accptHB)24.85
    Free energy of solvation of dipole (dip^2/V)0.0027648
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0875832
    Globularity descriptor (glob)0.821796
    Predicted polarizability in cubic angstroms (QPpolrz)53.899
    Predicted hexadecane/gas partition coefficient (QPlogPC16)20.286
    Predicted octanol/gas partition coefficient (QPlogPoct)45.277
    Predicted water/gas partition coefficient (QPlogPw)39.223
    Predicted octanol/water partition coefficient (QPlogPo/w)-2.097
    Predicted aqueous solubility (QPlogS)-1.383
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.005
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.732
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)11.291
    Predicted brain/blood partition coefficient (QPlogBB)-3.645
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)3.887
    Predicted skin permeability, log Kp (QPlogKp)-4.443
    PM3 calculated ionization potential (IP(ev))9.397
    PM3 calculated electron affinity (EA(eV))0.736
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)-1.65
    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)248.784
    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
    P08183ABCB1P-glycoprotein 1T25258SEA
    P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    P14151SELLLeukocyte adhesion molecule-1T60526SEA
    P60568IL2Interleukin-2T61698SEA
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    P09382LGALS1Galectin-1T09544SEA

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T25258DI0238Lung cancer[ICD-11: 2C25]P08183ABCB1
    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
    T60526DI0037Asthma[ICD-11: CA23]P14151SELL
    T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
    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

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