Cucurbitacin I 2-glucoside



Compound IDCDAMM02771
Common nameCucurbitacin I 2-glucoside
IUPAC name17-(2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl)-16-hydroxy-4,4,9,13,14-pentamethyl-2-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthrene-3,11-dione
Molecular formulaC36H52O12

Experimental data

Retention time10.24
Adduct[M+H]+
Actual mz677.353
Theoretical mz677.353
Error0.18
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8135

Identifiers and class information

Inchi keyLIIOJBIJVPGVGO-VAWYXSNFNA-N
SmilesO=C(C=CC(O)(C)C)C(O)(C)C1C(O)CC2(C)C3CC=C4C(C=C(OC5OC(CO)C(O)C(O)C5O)C(=O)C4(C)C)C3(C(=O)CC12C)C
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)6
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)14
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)676.8
Computed dipole moment(dipole)8.639
Total solvent accessible surface area (SASA)952.362
Hydrophobic component of SASA (FOSA)643.559
Hydrophilic component of SASA (FISA)286.676
Pie component of the SASA (PISA)22.126
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1930
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)18.45
Free energy of solvation of dipole (dip^2/V)0.0386736
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0512559
Globularity descriptor (glob)0.787169
Predicted polarizability in cubic angstroms (QPpolrz)62.307
Predicted hexadecane/gas partition coefficient (QPlogPC16)19.75
Predicted octanol/gas partition coefficient (QPlogPoct)41.897
Predicted water/gas partition coefficient (QPlogPw)29.449
Predicted octanol/water partition coefficient (QPlogPo/w)1.118
Predicted aqueous solubility (QPlogS)-4.637
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.558
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.081
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)18.939
Predicted brain/blood partition coefficient (QPlogBB)-3.365
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)6.798
Predicted skin permeability, log Kp (QPlogKp)-5.381
PM3 calculated ionization potential (IP(ev))9.347
PM3 calculated electron affinity (EA(eV))0.382
Number of likely metabolic reactions (#metab)10
Prediction of binding to human serum albumin (QPlogKhsa)-0.379
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)17.475
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)215.313
Number of nitrogen and oxygen atoms (#NandO)12
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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