Methyl 3,4-dihydroxy-5-prenylbenzoate 3-glucoside



Compound IDCDAMM01290
Common nameMethyl 3,4-dihydroxy-5-prenylbenzoate 3-glucoside
IUPAC namemethyl 4-hydroxy-3-(3-methylbut-2-enyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoate
Molecular formulaC19H26O9

Experimental data

Retention time10.41
Adduct[M+H]+
Actual mz399.166
Theoretical mz399.165
Error2.06
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7999

Identifiers and class information

Inchi keyOZKMIACEGRRXQA-UHFFFAOYNA-N
SmilesO=C(OC)C1=CC(OC2OC(CO)C(O)C(O)C2O)=C(O)C(=C1)CC=C(C)C
SuperclassPhenylpropanoids and polyketides
ClassTannins

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)11
Number of reactive functional groups (#rtvFG)2
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)398.409
Computed dipole moment(dipole)5.846
Total solvent accessible surface area (SASA)696.55
Hydrophobic component of SASA (FOSA)410.612
Hydrophilic component of SASA (FISA)234.611
Pie component of the SASA (PISA)51.327
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1244.74
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)12
Free energy of solvation of dipole (dip^2/V)0.0274552
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0385224
Globularity descriptor (glob)0.803401
Predicted polarizability in cubic angstroms (QPpolrz)37.088
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.962
Predicted octanol/gas partition coefficient (QPlogPoct)26.205
Predicted water/gas partition coefficient (QPlogPw)20.057
Predicted octanol/water partition coefficient (QPlogPo/w)0.218
Predicted aqueous solubility (QPlogS)-3.186
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.986
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.958
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)59.031
Predicted brain/blood partition coefficient (QPlogBB)-2.523
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)23.229
Predicted skin permeability, log Kp (QPlogKp)-4.606
PM3 calculated ionization potential (IP(ev))9.083
PM3 calculated electron affinity (EA(eV))0.277
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)-0.699
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)59.918
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)154.742
Number of nitrogen and oxygen atoms (#NandO)9
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
P16278GLB1Beta-galactosidase (by homology)T73134SEA
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
Q9BZP6CHIAAcidic mammalian chitinase (by homology)T51597SEA
P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
Q16831UPP1Uridine phosphorylase 1 (by homology)T97388SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P78536ADAM17ADAM17T82393SwissTargetPrediction
P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
P30556AGTR1Type-1 angiotensin II receptorT74456SwissTargetPrediction
Q02750MAP2K1Dual specificity mitogen-activated protein kinase kinase 1T99057SwissTargetPrediction
P26358DNMT1DNA (cytosine-5)-methyltransferase 1 (by homology)T88304SwissTargetPrediction
P00813ADAAdenosine deaminaseT03661SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SwissTargetPrediction
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
P52789HK2Hexokinase type IIT96685SwissTargetPrediction and SEA
P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P60568IL2Interleukin-2T61698SEA
P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SwissTargetPrediction
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SwissTargetPrediction and SEA
Q9H244P2RY12Purinergic receptor P2Y12 (by homology)T46937SwissTargetPrediction
P17931LGALS3Galectin-3T72038SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P14679TYRTyrosinaseT97035SEA
P11166SLC2A1Glucose transporter (by homology)T89458SwissTargetPrediction
P63316TNNC1Troponin, cardiac muscleT12966SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
P19429TNNI3Cardiac troponin IT20186SEA
P45379TNNT2Cardiac muscle troponin TT05887SEA

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
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
T73134DI0242Lysosomal disease[ICD-11: 5C56]P16278GLB1
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
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
T54156DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P14780MMP9
T54156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P14780MMP9
T54156DI0395Stomach cancer[ICD-11: 2B72]P14780MMP9
T54156DI0419Ulcerative colitis[ICD-11: DD71]P14780MMP9
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T65864DI0102Coronary atherosclerosis[ICD-11: BA52]Q16539MAPK14
T65864DI0287Myocardial infarction[ICD-11: BA41-BA43]Q16539MAPK14
T65864DI0366Rheumatoid arthritis[ICD-11: FA20]Q16539MAPK14
T65864DI0437Vitamin deficiency[ICD-11: 5B55-5B5F]Q16539MAPK14
T97388DI0292Nasopharyngitis[ICD-11: CA00]Q16831UPP1
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
T74456DI0137Essential hypertension[ICD-11: BA00]P30556AGTR1
T74456DI0190Hypertension[ICD-11: BA00-BA04]P30556AGTR1
T74456DI0373Secondary hypertension[ICD-11: BA04]P30556AGTR1
T74456DI0425Urinary system clinical symptom[ICD-11: MF8Y]P30556AGTR1
T99057DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]Q02750MAP2K1
T99057DI0336Phakomatoses/hamartoneoplastic syndrome[ICD-11: LD2D]Q02750MAP2K1
T88304DI0012Acute myeloid leukaemia[ICD-11: 2A60]P26358DNMT1
T88304DI0284Myelodysplastic syndrome[ICD-11: 2A37]P26358DNMT1
T88304DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P26358DNMT1
T03661DI0016Adaptive immunity immunodeficiency[ICD-11: 4A01]P00813ADA
T03661DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00813ADA
T03661DI0249Mature B-cell leukaemia[ICD-11: 2A82]P00813ADA
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
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
T19567DI0025Alzheimer disease[ICD-11: 8A20]O60502OGA
T19567DI0331Parkinsonism[ICD-11: 8A00]O60502OGA
T39321DI0279Muscular atrophy[ICD-11: 8B61]P04406GAPDH
T39321DI0280Muscular dystrophy[ICD-11: 8C70]P04406GAPDH
T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T77594DI0252Melanoma[ICD-11: 2C30]P11021HSPA5
T77594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11021HSPA5
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T07663DI0190Hypertension[ICD-11: BA00-BA04]O76074PDE5A
T07663DI0213Innate/adaptive immunodeficiency[ICD-11: 4A00]O76074PDE5A
T07663DI0378Sexual dysfunction[ICD-11: HA00-HA01]O76074PDE5A
T07663DI0411Tonus and reflex abnormality[ICD-11: MB47]O76074PDE5A
T61698DI0275Multiple sclerosis[ICD-11: 8A40]P60568IL2
T61698DI0361Renal cell carcinoma[ICD-11: 2C90]P60568IL2
T24587DI0369Sarcoma[ICD-11: 2A60-2C35]P16455MGMT
T46937DI0287Myocardial infarction[ICD-11: BA41-BA43]Q9H244P2RY12
T46937DI0405Thrombosis[ICD-11: DB61-GB90]Q9H244P2RY12
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
T89458DI0384Skin disease[ICD-11: EA00-EM0Z]P11166SLC2A1
T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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