Sesaminol glucoside



Compound IDCDAMM00527
Common nameSesaminol glucoside
IUPAC name2-[[6-[3-(1,3-benzodioxol-5-yl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-1,3-benzodioxol-5-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC26H28O12

Experimental data

Retention time12.75
Adduct[M+H]+
Actual mz533.174
Theoretical mz533.165
Error17.3
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.1285

Identifiers and class information

Inchi keyHVDZWQPYIXKSCL-UHFFFAOYNA-N
SmilesOCC1OC(OC2=CC=3OCOC3C=C2C4OCC5C(OCC45)C6=CC=C7OCOC7=C6)C(O)C(O)C1O
SuperclassLignans, neolignans and related compounds
ClassLignan glycosides

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)7
Number of reactive functional groups (#rtvFG)3
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)532.5
Computed dipole moment(dipole)6.328
Total solvent accessible surface area (SASA)644.67
Hydrophobic component of SASA (FOSA)354.984
Hydrophilic component of SASA (FISA)139.217
Pie component of the SASA (PISA)150.47
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1311.84
Number of hydrogen bond donors (donorHB)4
Number of hydrogen bond acceptors (accptHB)15.65
Free energy of solvation of dipole (dip^2/V)0.0305295
Index of cohesive interaction in solids (ACxDN^.5/SA)0.048552
Globularity descriptor (glob)0.898977
Predicted polarizability in cubic angstroms (QPpolrz)43.288
Predicted hexadecane/gas partition coefficient (QPlogPC16)13.362
Predicted octanol/gas partition coefficient (QPlogPoct)29.157
Predicted water/gas partition coefficient (QPlogPw)22.97
Predicted octanol/water partition coefficient (QPlogPo/w)0.399
Predicted aqueous solubility (QPlogS)-2.347
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.816
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.884
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)473.924
Predicted brain/blood partition coefficient (QPlogBB)-1.007
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)220.714
Predicted skin permeability, log Kp (QPlogKp)-2.883
PM3 calculated ionization potential (IP(ev))8.775
PM3 calculated electron affinity (EA(eV))-0.048
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)-0.69
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)51.254
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)151.194
Number of nitrogen and oxygen atoms (#NandO)12
Number of violations of Lipinski’s rule of five (RuleOfFive)2
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
P00533EGFREpidermal growth factor receptor erbB1T59328SwissTargetPrediction
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
P16050ALOX15Arachidonate 15-lipoxygenaseT16042SwissTargetPrediction
P18054ALOX12Arachidonate 12-lipoxygenaseT35527SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P05556ITGB1Integrin alpha2/beta1T01851SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
P25101EDNRAEndothelin receptor ET-AT23499SEA
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SwissTargetPrediction
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
P26010ITGB7Integrin alpha-4/beta-7T07403SwissTargetPrediction
P01111NRASGTPase NRasT35486SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
Q02880TOP2BDNA topoisomerase II betaT85733SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T59328DI0030Angina pectoris[ICD-11: BA40]P00533EGFR
T59328DI0062Breast cancer[ICD-11: 2C60-2C6Y]P00533EGFR
T59328DI0095Colorectal cancer[ICD-11: 2B91]P00533EGFR
T59328DI0121Diabetic foot ulcer[ICD-11: BD54]P00533EGFR
T59328DI0220Ischemia[ICD-11: 8B10-8B11]P00533EGFR
T59328DI0238Lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0303Non-small-cell lung cancer[ICD-11: 2C25]P00533EGFR
T59328DI0361Renal cell carcinoma[ICD-11: 2C90]P00533EGFR
T59328DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00533EGFR
T59328DI0420Unspecific body region injury[ICD-11: ND56]P00533EGFR
T77365DI0319Orthostatic hypotension[ICD-11: BA21]P29274ADORA2A
T77365DI0331Parkinsonism[ICD-11: 8A00]P29274ADORA2A
T77365DI0359Radionuclide imaging[ICD-11: N.A.]P29274ADORA2A
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
T88185DI0203Inborn lipid metabolism error[ICD-11: 5C52]Q8TDS4HCAR2
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
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
T01851DI0060Brain cancer[ICD-11: 2A00]P05556ITGB1
T01851DI0238Lung cancer[ICD-11: 2C25]P05556ITGB1
T01851DI0365Retinopathy[ICD-11: 9B71]P05556ITGB1
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
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
T24587DI0369Sarcoma[ICD-11: 2A60-2C35]P16455MGMT
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
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T07403DI0107Crohn disease[ICD-11: DD70]P26010ITGB7
T35486DI0095Colorectal cancer[ICD-11: 2B91]P01111NRAS
T35486DI0172Head and neck cancer[ICD-11: 2D42]P01111NRAS
T35486DI0238Lung cancer[ICD-11: 2C25]P01111NRAS
T35486DI0326Pancreatic cancer[ICD-11: 2C10]P01111NRAS
T35486DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P01111NRAS
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
T85733DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q02880TOP2B
T85733DI0076Chemoprotection[ICD-11: N.A.]Q02880TOP2B

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