Cucurbitacin C



Compound IDCDAMM01983
Common nameCucurbitacin C
IUPAC name[6-[3,16-dihydroxy-9-(hydroxymethyl)-4,4,13,14-tetramethyl-11-oxo-1,2,3,7,8,10,12,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxohept-3-en-2-yl] acetate
Molecular formulaC32H48O8

Experimental data

Retention time11.6
Adduct[M+H]+
Actual mz561.349
Theoretical mz561.342
Error11.8
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7835

Identifiers and class information

Inchi keyDGIGXLXLGBAJJN-BUHFOSPRNA-N
SmilesO=C(OC(C=CC(=O)C(O)(C)C1C(O)CC2(C)C3CC=C4C(CCC(O)C4(C)C)C3(C(=O)CC12C)CO)(C)C)C
SuperclassLipids and lipid-like molecules
ClassSteroids and steroid derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)0
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)10
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)560.726
Computed dipole moment(dipole)7.176
Total solvent accessible surface area (SASA)753.874
Hydrophobic component of SASA (FOSA)564.775
Hydrophilic component of SASA (FISA)174.489
Pie component of the SASA (PISA)14.61
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1602.46
Number of hydrogen bond donors (donorHB)3
Number of hydrogen bond acceptors (accptHB)10.85
Free energy of solvation of dipole (dip^2/V)0.0321341
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0249283
Globularity descriptor (glob)0.878464
Predicted polarizability in cubic angstroms (QPpolrz)51.695
Predicted hexadecane/gas partition coefficient (QPlogPC16)14.788
Predicted octanol/gas partition coefficient (QPlogPoct)28.017
Predicted water/gas partition coefficient (QPlogPw)15.695
Predicted octanol/water partition coefficient (QPlogPo/w)3.481
Predicted aqueous solubility (QPlogS)-4.481
Conformation-independent predicted aqueous solubility (CIQPlogS)-6.264
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.568
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)219.392
Predicted brain/blood partition coefficient (QPlogBB)-1.547
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)96.003
Predicted skin permeability, log Kp (QPlogKp)-3.724
PM3 calculated ionization potential (IP(ev))9.424
PM3 calculated electron affinity (EA(eV))0.195
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)0.47
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)76.273
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)145.889
Number of nitrogen and oxygen atoms (#NandO)8
Number of violations of Lipinski’s rule of five (RuleOfFive)1
Number of violations of Jorgensen’s rule of three (RuleOfThree)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P20701ITGALIntercellular adhesion molecule (ICAM-1), Integrin alpha-L/beta-2T35640SwissTargetPrediction and SEA
P40763STAT3Signal transducer and activator of transcription 3T29130SwissTargetPrediction

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T35640DI0351Psoriasis[ICD-11: EA90]P20701ITGAL
T35640DI0436Visual system disease[ICD-11: 9E1Z]P20701ITGAL
T29130DI0351Psoriasis[ICD-11: EA90]P40763STAT3

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