Cucurbitoside K



Compound IDCDAMM02019
Common nameCucurbitoside K
IUPAC name[5-[4,5-dihydroxy-6-(hydroxymethyl)-2-[4-(hydroxymethyl)phenoxy]oxan-3-yl]oxy-3,4-dihydroxyoxolan-3-yl]methyl 2-methylbutanoate
Molecular formulaC23H34O12

Experimental data

Retention time28.26
Adduct[M+K]+
Actual mz541.169
Theoretical mz541.168
Error1.56
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.003

Identifiers and class information

Inchi keyPWDKTMDATTYHBL-FVUPORNJNA-N
SmilesO=C(OCC1(O)COC(OC2C(OC3=CC=C(C=C3)CO)OC(CO)C(O)C2O)C1O)C(C)CC
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Pharmacokinetic properties

Number of descriptor values(#stars)2
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)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)502.514
Computed dipole moment(dipole)5.133
Total solvent accessible surface area (SASA)835.168
Hydrophobic component of SASA (FOSA)439.454
Hydrophilic component of SASA (FISA)272.069
Pie component of the SASA (PISA)123.646
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1524.06
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)17.1
Free energy of solvation of dipole (dip^2/V)0.0172851
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0501531
Globularity descriptor (glob)0.766877
Predicted polarizability in cubic angstroms (QPpolrz)45.746
Predicted hexadecane/gas partition coefficient (QPlogPC16)16.751
Predicted octanol/gas partition coefficient (QPlogPoct)33.354
Predicted water/gas partition coefficient (QPlogPw)26.522
Predicted octanol/water partition coefficient (QPlogPo/w)-0.402
Predicted aqueous solubility (QPlogS)-3.089
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.058
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.894
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)26.054
Predicted brain/blood partition coefficient (QPlogBB)-3.485
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)9.596
Predicted skin permeability, log Kp (QPlogKp)-4.562
PM3 calculated ionization potential (IP(ev))9.29
PM3 calculated electron affinity (EA(eV))-0.104
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-1.145
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)11.055
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)185.392
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)1

Compound-target network

Cytoscape Graph

Protein targets associated with phytocompound

Uniprot ID Gene name Target name TTD_ID Prediction source
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SwissTargetPrediction
P17931LGALS3Galectin-3T72038SwissTargetPrediction and SEA
P14679TYRTyrosinaseT97035SEA
P21452TACR2Neurokinin 2 receptorT52790SwissTargetPrediction
P09382LGALS1Galectin-1T09544SwissTargetPrediction
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
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
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
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
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T52790DI0218Irritable bowel syndrome[ICD-11: DD91]P21452TACR2
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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