(+)-7-epi-Syringaresinol 4\'-glucoside



Compound IDCDAMM02589
Common name(+)-7-epi-Syringaresinol 4\'-glucoside
IUPAC name2-[4-[3-(4-hydroxy-3,5-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC28H36O13

Experimental data

Retention time17.37
Adduct[M+H]+
Actual mz581.227
Theoretical mz581.223
Error5.72
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.4037

Identifiers and class information

Inchi keyWEKCEGQSIIQPAQ-UHFFFAOYNA-N
SmilesOC1=C(OC)C=C(C=C1OC)C2OCC3C(OCC23)C4=CC(OC)=C(OC5OC(CO)C(O)C(O)C5O)C(OC)=C4
SuperclassLignans, neolignans and related compounds
ClassLignan glycosides

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)12
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)580.585
Computed dipole moment(dipole)10.619
Total solvent accessible surface area (SASA)805.925
Hydrophobic component of SASA (FOSA)527.315
Hydrophilic component of SASA (FISA)206.474
Pie component of the SASA (PISA)72.136
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1583.41
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)16.4
Free energy of solvation of dipole (dip^2/V)0.0712212
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0455024
Globularity descriptor (glob)0.815203
Predicted polarizability in cubic angstroms (QPpolrz)50.198
Predicted hexadecane/gas partition coefficient (QPlogPC16)15.926
Predicted octanol/gas partition coefficient (QPlogPoct)33.818
Predicted water/gas partition coefficient (QPlogPw)24.384
Predicted octanol/water partition coefficient (QPlogPo/w)0.813
Predicted aqueous solubility (QPlogS)-3.489
Conformation-independent predicted aqueous solubility (CIQPlogS)-5.161
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.866
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)109.12
Predicted brain/blood partition coefficient (QPlogBB)-2.231
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)45.127
Predicted skin permeability, log Kp (QPlogKp)-3.919
PM3 calculated ionization potential (IP(ev))8.792
PM3 calculated electron affinity (EA(eV))0.005
Number of likely metabolic reactions (#metab)13
Prediction of binding to human serum albumin (QPlogKhsa)-0.632
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)42.263
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)165.601
Number of nitrogen and oxygen atoms (#NandO)13
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
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA
Q8N183NDUFAF2HUMAN NADH:ubiquinone oxidoreductase complex assembly factor 2T01453SEA
Q9P0J0NDUFA13Mitochondrial complex IT82391SEA
Q9Y6M9NDUFB9HUMAN NADH:ubiquinone oxidoreductase subunit B9T01465SEA
Q8N183NDUFAF2HUMAN NADH:ubiquinone oxidoreductase complex assembly factor 2T01453SEA
P03897MT-ND3NADH dehydrogenaseT77195SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
Q02880TOP2BDNA topoisomerase II betaT85733SEA

Target associated diseases

TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
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
T60526DI0037Asthma[ICD-11: CA23]P14151SELL
T60526DI0088Circulatory system disease[ICD-11: BE2Z]P14151SELL
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
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
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T82391DI0069Cardiomyopathy[ICD-11: BC43]Q9P0J0NDUFA13
T77195DI0331Parkinsonism[ICD-11: 8A00]P03897MT-ND3
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1
T85733DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q02880TOP2B
T85733DI0076Chemoprotection[ICD-11: N.A.]Q02880TOP2B

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