Mycophenolic acid glucuronide



Compound IDCDAMM00617
Common nameMycophenolic acid glucuronide
IUPAC name6-[[5-(5-carboxy-3-methylpent-2-enyl)-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-4-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Molecular formulaC23H28O12

Experimental data

Retention time0.35
Adduct[M+H]+
Actual mz497.163
Theoretical mz497.165
Error4.18
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9708

Identifiers and class information

Inchi keyBYFGTSAYQQIUCN-WTKPLQERNA-N
SmilesO=C(O)CCC(=CCC1=C(OC)C(=C2C(C(=O)OC2)=C1OC3OC(C(=O)O)C(O)C(O)C3O)C)C
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)4
    Number of non-conjugated amine groups (#amine)0
    Number of amidine and guanidine groups (#amidine)0
    Number of carboxylic acid groups (#acid)2
    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)496.467
    Computed dipole moment(dipole)8.642
    Total solvent accessible surface area (SASA)728.335
    Hydrophobic component of SASA (FOSA)350.736
    Hydrophilic component of SASA (FISA)354.607
    Pie component of the SASA (PISA)22.993
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1383.14
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)14.3
    Free energy of solvation of dipole (dip^2/V)0.05399
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0392676
    Globularity descriptor (glob)0.824287
    Predicted polarizability in cubic angstroms (QPpolrz)41.714
    Predicted hexadecane/gas partition coefficient (QPlogPC16)14.608
    Predicted octanol/gas partition coefficient (QPlogPoct)28.633
    Predicted water/gas partition coefficient (QPlogPw)21.337
    Predicted octanol/water partition coefficient (QPlogPo/w)0.501
    Predicted aqueous solubility (QPlogS)-2.897
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.083
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-0.87
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)0.276
    Predicted brain/blood partition coefficient (QPlogBB)-3.639
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.114
    Predicted skin permeability, log Kp (QPlogKp)-6.822
    PM3 calculated ionization potential (IP(ev))10.043
    PM3 calculated electron affinity (EA(eV))1.046
    Number of likely metabolic reactions (#metab)11
    Prediction of binding to human serum albumin (QPlogKhsa)-1.059
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)6.903
    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)222.735
    Number of nitrogen and oxygen atoms (#NandO)12
    Number of violations of Lipinski’s rule of five (RuleOfFive)1
    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 XIIT16987SwissTargetPrediction
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P12821ACEAngiotensin-converting enzymeT98311SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction
    P42336PIK3CAPI3-kinase p110-alpha subunitT80276SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P08473MMENeprilysinT05409SwissTargetPrediction
    P39086GRIK1Glutamate receptor ionotropic kainate 1T73495SwissTargetPrediction
    Q13002GRIK2Glutamate receptor ionotropic kainate 2T58178SwissTargetPrediction
    Q13003GRIK3Glutamate receptor ionotropic kainate 3T68876SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P42575CASP2Caspase-2T09128SwissTargetPrediction
    P04035HMGCRHMG-CoA reductaseT53585SwissTargetPrediction
    P29466CASP1Caspase-1T98269SwissTargetPrediction
    P26358DNMT1DNA (cytosine-5)-methyltransferase 1 (by homology)T88304SwissTargetPrediction
    P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
    P42574CASP3Caspase-3T57943SwissTargetPrediction
    P55210CASP7Caspase-7T72252SwissTargetPrediction
    P50281MMP14Matrix metalloproteinase 14T65019SwissTargetPrediction
    P16109SELPP-selectinT10965SwissTargetPrediction
    P14151SELLLeukocyte adhesion molecule-1T60526SwissTargetPrediction
    P55212CASP6Caspase-6T20600SwissTargetPrediction
    Q9UQ81MCH5Caspase-8T15700SwissTargetPrediction
    P48736PIK3CGPI3-kinase p110-gamma subunitT95913SwissTargetPrediction
    P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SEA
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction and SEA
    P17931LGALS3Galectin-3T72038SwissTargetPrediction
    Q9Y3Q0NAALAD2NAALADase IIT70036SwissTargetPrediction
    P22102GARTGAR transformylaseT72042SwissTargetPrediction
    P51512MMP16Matrix metalloproteinase 16T35824SwissTargetPrediction
    Q9UBC3DNMT3BDNA (cytosine-5)-methyltransferase 3BT65501SwissTargetPrediction
    Q92887CMOATMultidrug resistance-associated protein 2T61792SEA

    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
    T98311DI0175Heart failure[ICD-11: BD10-BD1Z]P12821ACE
    T98311DI0190Hypertension[ICD-11: BA00-BA04]P12821ACE
    T13201DI0166Glaucoma[ICD-11: 9C61]P00915CA1
    T13201DI0372Seborrhoeic dermatitis[ICD-11: EA81]P00915CA1
    T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
    T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
    T80276DI0062Breast cancer[ICD-11: 2C60-2C6Y]P42336PIK3CA
    T80276DI0151Follicular lymphoma[ICD-11: 2A80]P42336PIK3CA
    T80276DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P42336PIK3CA
    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
    T05409DI0175Heart failure[ICD-11: BD10-BD1Z]P08473MME
    T73495DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P39086GRIK1
    T73495DI0396Substance abuse[ICD-11: 6C40]P39086GRIK1
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    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
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T53585DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P04035HMGCR
    T53585DI0102Coronary atherosclerosis[ICD-11: BA52]P04035HMGCR
    T53585DI0128Dyslipidemia[ICD-11: 5C80-5C81]P04035HMGCR
    T53585DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P04035HMGCR
    T53585DI0275Multiple sclerosis[ICD-11: 8A40]P04035HMGCR
    T53585DI0287Myocardial infarction[ICD-11: BA41-BA43]P04035HMGCR
    T53585DI0324Pain[ICD-11: MG30-MG3Z]P04035HMGCR
    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
    T88304DI0012Acute myeloid leukaemia[ICD-11: 2A60]P26358DNMT1
    T88304DI0284Myelodysplastic syndrome[ICD-11: 2A37]P26358DNMT1
    T88304DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P26358DNMT1
    T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
    T72252DI0110Cystic fibrosis[ICD-11: CA25]P55210CASP7
    T65019DI0178Hepatic fibrosis/cirrhosis[ICD-11: DB93]P50281MMP14
    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
    T40111DI0062Breast cancer[ICD-11: 2C60-2C6Y]P20839IMPDH1
    T40111DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P20839IMPDH1
    T40111DI0250Mature B-cell lymphoma[ICD-11: 2A85]P20839IMPDH1
    T40111DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P20839IMPDH1
    T40111DI0413Transplant rejection[ICD-11: NE84]P20839IMPDH1
    T89360DI0413Transplant rejection[ICD-11: NE84]P12268IMPDH2
    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
    T72042DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P22102GART
    T65501DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UBC3DNMT3B

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