4-Hydroxy-3-prenylbenzoic acid glucoside



Compound IDCDAMM01498
Common name4-Hydroxy-3-prenylbenzoic acid glucoside
IUPAC name3-(3-methylbut-2-enyl)-4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzoic acid
Molecular formulaC18H24O8

Experimental data

Retention time11.63
Adduct[M+K]+
Actual mz407.107
Theoretical mz407.11
Error7.27
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.94

Identifiers and class information

Inchi keyZTHSABILDCCHJR-UHFFFAOYNA-N
SmilesO=C(O)C1=CC=C(OC2OC(CO)C(O)C(O)C2O)C(=C1)CC=C(C)C
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

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)1
Number of non-conjugated amide groups (#amide)0
Number of rotatable bonds (#rotor)10
Number of reactive functional groups (#rtvFG)1
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)368.383
Computed dipole moment(dipole)7.005
Total solvent accessible surface area (SASA)624.232
Hydrophobic component of SASA (FOSA)288.977
Hydrophilic component of SASA (FISA)252.89
Pie component of the SASA (PISA)82.366
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1125.01
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)11.25
Free energy of solvation of dipole (dip^2/V)0.0436169
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0402987
Globularity descriptor (glob)0.838022
Predicted polarizability in cubic angstroms (QPpolrz)33.234
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.167
Predicted octanol/gas partition coefficient (QPlogPoct)24.947
Predicted water/gas partition coefficient (QPlogPw)19.7
Predicted octanol/water partition coefficient (QPlogPo/w)0.306
Predicted aqueous solubility (QPlogS)-2.548
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.719
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-2.738
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)10.031
Predicted brain/blood partition coefficient (QPlogBB)-2.44
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)4.35
Predicted skin permeability, log Kp (QPlogKp)-4.93
PM3 calculated ionization potential (IP(ev))9.479
PM3 calculated electron affinity (EA(eV))0.423
Number of likely metabolic reactions (#metab)7
Prediction of binding to human serum albumin (QPlogKhsa)-0.887
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)46.659
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)146.996
Number of nitrogen and oxygen atoms (#NandO)8
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction
O43570CA12Carbonic anhydrase XIIT16987SEA
Q16790CA9Carbonic anhydrase IXT64567SEA
P00915CA1Carbonic anhydrase IT13201SEA
P42336PIK3CAPI3-kinase p110-alpha subunitT80276SwissTargetPrediction
P16278GLB1Beta-galactosidase (by homology)T73134SEA
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P11926ODC1Ornithine decarboxylaseT60366SEA
P35968KDRVascular endothelial growth factor receptor 2T80975SwissTargetPrediction
Q9BZP6CHIAAcidic mammalian chitinase (by homology)T51597SEA
Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
P42575CASP2Caspase-2T09128SwissTargetPrediction
P10276RARARetinoic acid receptor alphaT94085SEA
P29466CASP1Caspase-1T98269SwissTargetPrediction
P32320CDACytidine deaminase (by homology)T79027SEA
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
Q9Y251HPSEHeparanaseT47623SEA
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
P52789HK2Hexokinase type IIT96685SwissTargetPrediction and SEA
Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
P42574CASP3Caspase-3T57943SwissTargetPrediction
P55210CASP7Caspase-7T72252SwissTargetPrediction
P16109SELPP-selectinT10965SwissTargetPrediction and SEA
P14151SELLLeukocyte adhesion molecule-1T60526SwissTargetPrediction and SEA
P55212CASP6Caspase-6T20600SwissTargetPrediction
Q9UQ81MCH5Caspase-8T15700SwissTargetPrediction
P48736PIK3CGPI3-kinase p110-gamma subunitT95913SwissTargetPrediction
P01112HRASTransforming protein p21/H-Ras-1T71081SEA
P60568IL2Interleukin-2T61698SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SEA
P17931LGALS3Galectin-3T72038SEA
P14679TYRTyrosinaseT97035SEA
P20916MAGMyelin-associated glycoprotein (by homology)T95286SEA
P63316TNNC1Troponin, cardiac muscleT12966SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
Q07108CD69Early activation antigen CD69T48780SEA
P30837ALDH1B1Acetaldehyde dehydrogenaseT99641SEA
P19429TNNI3Cardiac troponin IT20186SEA
P45379TNNT2Cardiac muscle troponin TT05887SEA

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
T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
T80276DI0062Breast cancer[ICD-11: 2C60-2C6Y]P42336PIK3CA
T80276DI0151Follicular lymphoma[ICD-11: 2A80]P42336PIK3CA
T80276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P42336PIK3CA
T73134DI0242Lysosomal disease[ICD-11: 5C56]P16278GLB1
T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
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
T80975DI0062Breast cancer[ICD-11: 2C60-2C6Y]P35968KDR
T80975DI0095Colorectal cancer[ICD-11: 2B91]P35968KDR
T80975DI0160Gastrointestinal stromal tumour[ICD-11: 2B5B]P35968KDR
T80975DI0244Malignant digestive organ neoplasm[ICD-11: 2C11]P35968KDR
T80975DI0361Renal cell carcinoma[ICD-11: 2C90]P35968KDR
T80975DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P35968KDR
T80975DI0395Stomach cancer[ICD-11: 2B72]P35968KDR
T80975DI0403Thrombocytopenia[ICD-11: 3B64]P35968KDR
T80975DI0407Thyroid cancer[ICD-11: 2D10]P35968KDR
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T94085DI0025Alzheimer disease[ICD-11: 8A20]P10276RARA
T94085DI0251Mature T-cell lymphoma[ICD-11: 2A90]P10276RARA
T98269DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P29466CASP1
T98269DI0146Fibrosis[ICD-11: GA14-GC01]P29466CASP1
T98269DI0366Rheumatoid arthritis[ICD-11: FA20]P29466CASP1
T98269DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P29466CASP1
T79027DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P32320CDA
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
T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T22583DI0009Acute diabete complication[ICD-11: 5A2Y]Q9NY91SLC5A4
T22583DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NY91SLC5A4
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
T72252DI0110Cystic fibrosis[ICD-11: CA25]P55210CASP7
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
T15700DI0120Diabetes mellitus[ICD-11: 5A10]Q9UQ81MCH5
T15700DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UQ81MCH5
T95913DI0151Follicular lymphoma[ICD-11: 2A80]P48736PIK3CG
T95913DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P48736PIK3CG
T95913DI0249Mature B-cell leukaemia[ICD-11: 2A82]P48736PIK3CG
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
T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
T95286DI0219Ischaemic/haemorrhagic stroke[ICD-11: 8B20]P20916MAG
T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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