Phenyl beta-D-glucopyranoside



Compound IDCDAMM00475
Common namePhenyl beta-D-glucopyranoside
IUPAC name2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
Molecular formulaC12H16O6

Experimental data

Retention time11.17
Adduct[M+H]+
Actual mz257.099
Theoretical mz257.102
Error12.74
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.9108

Identifiers and class information

Inchi keyNEZJDVYDSZTRFS-WLEIBRHLNA-N
SmilesOCC1OC(OC=2C=CC=CC2)C(O)C(O)C1O
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • 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)1
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)256.255
    Computed dipole moment(dipole)4.73
    Total solvent accessible surface area (SASA)456.428
    Hydrophobic component of SASA (FOSA)118.408
    Hydrophilic component of SASA (FISA)161.379
    Pie component of the SASA (PISA)176.641
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)793.778
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)9.25
    Free energy of solvation of dipole (dip^2/V)0.0281865
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0405322
    Globularity descriptor (glob)0.908362
    Predicted polarizability in cubic angstroms (QPpolrz)22.805
    Predicted hexadecane/gas partition coefficient (QPlogPC16)9.109
    Predicted octanol/gas partition coefficient (QPlogPoct)18.468
    Predicted water/gas partition coefficient (QPlogPw)16.542
    Predicted octanol/water partition coefficient (QPlogPo/w)-0.343
    Predicted aqueous solubility (QPlogS)-1.329
    Conformation-independent predicted aqueous solubility (CIQPlogS)-1.567
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.857
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)292.106
    Predicted brain/blood partition coefficient (QPlogBB)-1.162
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)130.816
    Predicted skin permeability, log Kp (QPlogKp)-3.199
    PM3 calculated ionization potential (IP(ev))8.98
    PM3 calculated electron affinity (EA(eV))-0.541
    Number of likely metabolic reactions (#metab)4
    Prediction of binding to human serum albumin (QPlogKhsa)-0.83
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)69.067
    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)99.905
    Number of nitrogen and oxygen atoms (#NandO)6
    Number of violations of Lipinski’s rule of five (RuleOfFive)0
    Number of violations of Jorgensen’s rule of three (RuleOfThree)0

    Compound-target network

    Cytoscape Graph

    Protein targets associated with phytocompound

    Uniprot ID Gene name Target name TTD_ID Prediction source
    P29274ADORA2AAdenosine A2a receptorT77365SEA
    P30542ADORA1Adenosine A1 receptorT92072SEA
    O43570CA12Carbonic anhydrase XIIT16987SEA
    Q16790CA9Carbonic anhydrase IXT64567SEA
    P0DMS8ADORA3Adenosine A3 receptorT36059SEA
    P00915CA1Carbonic anhydrase IT13201SEA
    P00918CA2Carbonic anhydrase IIT20401SEA
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    P32320CDACytidine deaminase (by homology)T79027SEA
    P00813ADAAdenosine deaminaseT03661SEA
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    Q9Y251HPSEHeparanaseT47623SEA
    P55263ADKAdenosine kinaseT91661SEA
    O60502OGABifunctional protein NCOATT19567SEA
    P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SEA
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SEA
    P52789HK2Hexokinase type IIT96685SEA
    O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SEA
    P16109SELPP-selectinT10965SEA
    P14151SELLLeukocyte adhesion molecule-1T60526SEA
    P01112HRASTransforming protein p21/H-Ras-1T71081SEA
    P60568IL2Interleukin-2T61698SEA
    P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SEA
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    Q15077P2RY6Pyrimidinergic receptor P2Y6T90782SEA
    P63316TNNC1Troponin, cardiac muscleT12966SEA
    P06865HEXABeta-hexosaminidase subunit alphaT63196SEA
    P07686HEXBBeta-N-acetyl-D-hexosaminidase-A/BT63197SEA
    P09382LGALS1Galectin-1T09544SEA
    P01111NRASGTPase NRasT35486SEA
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
    Q15391P2RY14Purinergic receptor P2Y14T16555SEA
    P05231IL6Interleukin-6T32578SEA
    P11717IGF2RInsulin-like growth factor II receptorT59550SEA
    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
    T92072DI0319Orthostatic hypotension[ICD-11: BA21]P30542ADORA1
    T16987DI0046Bacterial infection[ICD-11: 1A00-1C4Z]O43570CA12
    T16987DI0372Seborrhoeic dermatitis[ICD-11: EA81]O43570CA12
    T64567DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q16790CA9
    T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
    T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
    T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
    T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
    T20401DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P00918CA2
    T20401DI0137Essential hypertension[ICD-11: BA00]P00918CA2
    T20401DI0166Glaucoma[ICD-11: 9C61]P00918CA2
    T20401DI0175Heart failure[ICD-11: BD10-BD1Z]P00918CA2
    T20401DI0214Insomnia[ICD-11: 7A00-7A0Z]P00918CA2
    T20401DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00918CA2
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T79027DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P32320CDA
    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
    T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
    T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
    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
    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
    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
    T90782DI0025Alzheimer disease[ICD-11: 8A20]Q15077P2RY6
    T12966DI0006Acquired cutaneous blood vessel malformation[ICD-11: EF20]P63316TNNC1
    T12966DI0175Heart failure[ICD-11: BD10-BD1Z]P63316TNNC1
    T63196DI0242Lysosomal disease[ICD-11: 5C56]P06865HEXA
    T63197DI0242Lysosomal disease[ICD-11: 5C56]P07686HEXB
    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
    T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6
    T59550DI0146Fibrosis[ICD-11: GA14-GC01]P11717IGF2R
    T59550DI0368Sarcoidosis[ICD-11: 4B20]P11717IGF2R
    T99641DI0396Substance abuse[ICD-11: 6C40]P30837ALDH1B1

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