Eurostoside



Compound IDCDAMM01801
Common nameEurostoside
IUPAC name[4a,5-dihydroxy-1-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,7a-dihydro-1H-cyclopenta[c]pyran-7-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
Molecular formulaC24H28O12

Experimental data

Retention time8.72
Adduct[M+H]+
Actual mz509.162
Theoretical mz509.165
Error7.22
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.0649

Identifiers and class information

Inchi keySSFSGTBTPVWUPA-UJBYXYFXNA-N
SmilesO=C(OCC1=CC(O)C2(O)C=COC(OC3OC(CO)C(O)C(O)C3O)C12)C=CC4=CC=C(O)C=C4
SuperclassLipids and lipid-like molecules
ClassPrenol lipids

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)15
Number of reactive functional groups (#rtvFG)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)508.478
Computed dipole moment(dipole)1.51
Total solvent accessible surface area (SASA)686.281
Hydrophobic component of SASA (FOSA)174.878
Hydrophilic component of SASA (FISA)263.426
Pie component of the SASA (PISA)247.976
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1347.47
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)17.1
Free energy of solvation of dipole (dip^2/V)0.0016923
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0659239
Globularity descriptor (glob)0.859694
Predicted polarizability in cubic angstroms (QPpolrz)40.509
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.875
Predicted octanol/gas partition coefficient (QPlogPoct)33.311
Predicted water/gas partition coefficient (QPlogPw)28.636
Predicted octanol/water partition coefficient (QPlogPo/w)-0.949
Predicted aqueous solubility (QPlogS)-1.605
Conformation-independent predicted aqueous solubility (CIQPlogS)-3.356
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.985
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)31.465
Predicted brain/blood partition coefficient (QPlogBB)-2.717
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)11.767
Predicted skin permeability, log Kp (QPlogKp)-4.061
PM3 calculated ionization potential (IP(ev))9.057
PM3 calculated electron affinity (EA(eV))0.653
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)-1.115
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)9.32
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)194.592
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
O43570CA12Carbonic anhydrase XIIT16987SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P11511CYP19A1Cytochrome P450 19A1T13260SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P01375TNFTNF-alphaT20178SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P60568IL2Interleukin-2T61698SEA
P14679TYRTyrosinaseT97035SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T13260DI0062Breast cancer[ICD-11: 2C60-2C6Y]P11511CYP19A1
T13260DI0108Cushing syndrome[ICD-11: 5A70]P11511CYP19A1
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
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
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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