8-Hydroxypinoresinol 4-glucoside



Compound IDCDAMM02652
Common name8-Hydroxypinoresinol 4-glucoside
IUPAC name2-[4-[3a-hydroxy-6-(4-hydroxy-3-methoxyphenyl)-3,4,6,6a-tetrahydro-1H-furo[3,4-c]furan-3-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular formulaC26H32O12

Experimental data

Retention time9.96
Adduct[M+H]+
Actual mz537.199
Theoretical mz537.196
Error5.63
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.2867

Identifiers and class information

Inchi keyORRYWOBRSQRASU-UHFFFAOYNA-N
SmilesOC1=CC=C(C=C1OC)C2OCC3(O)C(OCC23)C4=CC=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)11
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)536.532
Computed dipole moment(dipole)3.927
Total solvent accessible surface area (SASA)799.675
Hydrophobic component of SASA (FOSA)416.88
Hydrophilic component of SASA (FISA)233.707
Pie component of the SASA (PISA)149.088
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1514.81
Number of hydrogen bond donors (donorHB)6
Number of hydrogen bond acceptors (accptHB)15.65
Free energy of solvation of dipole (dip^2/V)0.0101785
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0479376
Globularity descriptor (glob)0.79767
Predicted polarizability in cubic angstroms (QPpolrz)48.829
Predicted hexadecane/gas partition coefficient (QPlogPC16)16.377
Predicted octanol/gas partition coefficient (QPlogPoct)33.728
Predicted water/gas partition coefficient (QPlogPw)26.024
Predicted octanol/water partition coefficient (QPlogPo/w)0.44
Predicted aqueous solubility (QPlogS)-3.768
Conformation-independent predicted aqueous solubility (CIQPlogS)-4.571
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.517
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)60.209
Predicted brain/blood partition coefficient (QPlogBB)-2.548
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)23.731
Predicted skin permeability, log Kp (QPlogKp)-4.245
PM3 calculated ionization potential (IP(ev))8.932
PM3 calculated electron affinity (EA(eV))-0.005
Number of likely metabolic reactions (#metab)12
Prediction of binding to human serum albumin (QPlogKhsa)-0.667
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)22.501
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)170.63
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
Q07820MCL1Induced myeloid leukemia cell differentiation protein Mcl-1T14912SwissTargetPrediction
Q8TDS4HCAR2Hydroxycarboxylic acid receptor 2T88185SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction and SEA
Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
P16109SELPP-selectinT10965SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction and SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SwissTargetPrediction and SEA
O75908SOAT2Acyl coenzyme A:cholesterol acyltransferase 2T14463SwissTargetPrediction
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SwissTargetPrediction and SEA
Q16665HIF1AHypoxia-inducible factor 1 alphaT55610SwissTargetPrediction
O75908SOAT2Acyl coenzyme A:cholesterol acyltransferase 2T14463SwissTargetPrediction
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

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
T14912DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q07820MCL1
T14912DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q07820MCL1
T14912DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q07820MCL1
T14912DI0252Melanoma[ICD-11: 2C30]Q07820MCL1
T14912DI0274Multiple myeloma[ICD-11: 2A83]Q07820MCL1
T14912DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q07820MCL1
T88185DI0203Inborn lipid metabolism error[ICD-11: 5C52]Q8TDS4HCAR2
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T60366DI0020African trypanosomiasis[ICD-11: 1F51]P11926ODC1
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
T22583DI0009Acute diabete complication[ICD-11: 5A2Y]Q9NY91SLC5A4
T22583DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NY91SLC5A4
T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
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
T14463DI0017Adrenal cancer[ICD-11: 2D11]O75908SOAT2
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
T55610DI0241Lymphoma[ICD-11: 2A80-2A86]Q16665HIF1A
T55610DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16665HIF1A
T14463DI0017Adrenal cancer[ICD-11: 2D11]O75908SOAT2
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T82391DI0069Cardiomyopathy[ICD-11: BC43]Q9P0J0NDUFA13
T77195DI0331Parkinsonism[ICD-11: 8A00]P03897MT-ND3
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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