Cucurbitacin K 2-O-beta-D-glucopyranoside



Compound IDCDAMM02752
Common nameCucurbitacin K 2-O-beta-D-glucopyranoside
IUPAC name16-hydroxy-4,4,9,13,14-pentamethyl-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-(2,5,6-trihydroxy-6-methyl-3-oxoheptan-2-yl)-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Molecular formulaC36H54O13

Experimental data

Retention time16.08
Adduct[M+H]+
Actual mz695.356
Theoretical mz695.363
Error10.03
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.0297

Identifiers and class information

Inchi keyXPEAYHKXEWXAKV-DDJGDBTFNA-N
SmilesO=C1C(OC2OC(CO)C(O)C(O)C2O)=CC3C(=CCC4C3(C(=O)CC5(C)C(C(O)CC45C)C(O)(C(=O)CC(O)C(O)(C)C)C)C)C1(C)C
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)7
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)16
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)694.815
Computed dipole moment(dipole)4.237
Total solvent accessible surface area (SASA)950.352
Hydrophobic component of SASA (FOSA)616.22
Hydrophilic component of SASA (FISA)318.603
Pie component of the SASA (PISA)15.528
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1942.76
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)19.15
Free energy of solvation of dipole (dip^2/V)0.0092397
Index of cohesive interaction in solids (ACxDN^.5/SA)0.053313
Globularity descriptor (glob)0.792308
Predicted polarizability in cubic angstroms (QPpolrz)61.47
Predicted hexadecane/gas partition coefficient (QPlogPC16)19.981
Predicted octanol/gas partition coefficient (QPlogPoct)41.697
Predicted water/gas partition coefficient (QPlogPw)29.864
Predicted octanol/water partition coefficient (QPlogPo/w)0.722
Predicted aqueous solubility (QPlogS)-4.113
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.635
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.967
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)9.432
Predicted brain/blood partition coefficient (QPlogBB)-3.784
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)3.2
Predicted skin permeability, log Kp (QPlogKp)-5.801
PM3 calculated ionization potential (IP(ev))9.723
PM3 calculated electron affinity (EA(eV))0.233
Number of likely metabolic reactions (#metab)12
Prediction of binding to human serum albumin (QPlogKhsa)-0.525
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)9.743
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)237.256
Number of nitrogen and oxygen atoms (#NandO)13
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
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P20701ITGALIntercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2T35640SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T35640DI0351Psoriasis[ICD-11: EA90]P20701ITGAL
T35640DI0436Visual system disease[ICD-11: 9E1Z]P20701ITGAL

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