Smilaside I



Compound IDCDAMM01783
Common nameSmilaside I
IUPAC name[2-[6-(acetyloxymethyl)-3,4,5-trihydroxyoxan-2-yl]oxy-3-hydroxy-5-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyloxymethyl]-4-[3-(4-hydroxyphenyl)prop-2-enoyloxy]oxolan-2-yl]methyl 3-(4-hydroxyphenyl)prop-2-enoate
Molecular formulaC42H44O19

Experimental data

Retention time26.5
Adduct[M+H]+
Actual mz853.261
Theoretical mz853.255
Error6.94
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score5.0751

Identifiers and class information

Inchi keyYWTCWUMCRKCKAD-WWHVMFIUNA-N
SmilesO=C(OCC1OC(OC2OC(COC(=O)C)C(O)C(O)C2O)(COC(=O)C=CC3=CC=C(O)C=C3)C(O)C1OC(=O)C=CC4=CC=C(O)C=C4)C=CC5=CC=C(O)C(OC)=C5
SuperclassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives

Pharmacokinetic properties

Number of descriptor values(#stars)11
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)26
Number of reactive functional groups (#rtvFG)6
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)852.798
Computed dipole moment(dipole)9.011
Total solvent accessible surface area (SASA)1064.09
Hydrophobic component of SASA (FOSA)322.736
Hydrophilic component of SASA (FISA)423.206
Pie component of the SASA (PISA)318.153
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)2243.06
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)21
Free energy of solvation of dipole (dip^2/V)0.0361988
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0522141
Globularity descriptor (glob)0.778774
Predicted polarizability in cubic angstroms (QPpolrz)69.957
Predicted hexadecane/gas partition coefficient (QPlogPC16)25.469
Predicted octanol/gas partition coefficient (QPlogPoct)46.795
Predicted water/gas partition coefficient (QPlogPw)32.524
Predicted octanol/water partition coefficient (QPlogPo/w)1.362
Predicted aqueous solubility (QPlogS)-3.562
Conformation-independent predicted aqueous solubility (CIQPlogS)-8.754
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-6.629
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.961
Predicted brain/blood partition coefficient (QPlogBB)-5.656
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.271
Predicted skin permeability, log Kp (QPlogKp)-5.702
PM3 calculated ionization potential (IP(ev))9.045
PM3 calculated electron affinity (EA(eV))1.042
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)-0.621
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
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)308.118
Number of nitrogen and oxygen atoms (#NandO)19
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
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
P05067APPBeta amyloid A4 proteinT87024SEA
P43166CA7Carbonic anhydrase VIIT37541SEA
P23280CA6Carbonic anhydrase VIT06569SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P15121AKR1B1Aldose reductaseT26623SEA
P11926ODC1Ornithine decarboxylaseT60366SEA
P19838NFKB1Nuclear factor NF-kappa-B p105 subunitT83145SEA
Q09472EP300Histone acetyltransferase p300T25956SEA
P08581METHepatocyte growth factor receptorT40474SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P10636MAPTMicrotubule-associated protein tauT45593SEA
Q04760GLO1Glyoxalase IT88285SEA
Q16236NFE2L2Nuclear factor erythroid 2-related factor 2T88505SEA
O43826SLC37A4Glucose-6-phosphate translocaseT47306SEA

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
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
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
T26623DI0298Neuropathy[ICD-11: 8C0Z]P15121AKR1B1
T26623DI0366Rheumatoid arthritis[ICD-11: FA20]P15121AKR1B1
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
T83145DI0218Irritable bowel syndrome[ICD-11: DD91]P19838NFKB1
T83145DI0366Rheumatoid arthritis[ICD-11: FA20]P19838NFKB1
T25956DI0346Prostate cancer[ICD-11: 2C82]Q09472EP300
T25956DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q09472EP300
T40474DI0238Lung cancer[ICD-11: 2C25]P08581MET
T40474DI0303Non-small-cell lung cancer[ICD-11: 2C25]P08581MET
T40474DI0407Thyroid cancer[ICD-11: 2D10]P08581MET
T45593DI0012Acute myeloid leukaemia[ICD-11: 2A60]P10636MAPT
T45593DI0025Alzheimer disease[ICD-11: 8A20]P10636MAPT
T45593DI0265Mild neurocognitive disorder[ICD-11: 6D71]P10636MAPT
T88285DI0210Influenza[ICD-11: 1E30-1E32]Q04760GLO1
T88505DI0038Ataxic disorder[ICD-11: 8A03]Q16236NFE2L2

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