Mycophenolic acid O-acyl-glucuronide



Compound IDCDAMM00523
Common nameMycophenolic acid O-acyl-glucuronide
IUPAC name3,4,5-trihydroxy-6-[6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoyl]oxyoxane-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
Score7.2127

Identifiers and class information

Inchi keyQBMSTEZXAMABFF-YAWDXNJXNA-N
SmilesO=C1OCC2=C1C(O)=C(C(OC)=C2C)CC=C(C)CCC(=O)OC3OC(C(=O)O)C(O)C(O)C3O
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)1
    Number of non-conjugated amide groups (#amide)0
    Number of rotatable bonds (#rotor)12
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)496.467
    Computed dipole moment(dipole)6.443
    Total solvent accessible surface area (SASA)771.835
    Hydrophobic component of SASA (FOSA)414.471
    Hydrophilic component of SASA (FISA)335.817
    Pie component of the SASA (PISA)21.547
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1430.29
    Number of hydrogen bond donors (donorHB)3
    Number of hydrogen bond acceptors (accptHB)13.3
    Free energy of solvation of dipole (dip^2/V)0.0290222
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0298461
    Globularity descriptor (glob)0.795409
    Predicted polarizability in cubic angstroms (QPpolrz)43.587
    Predicted hexadecane/gas partition coefficient (QPlogPC16)14.763
    Predicted octanol/gas partition coefficient (QPlogPoct)26.743
    Predicted water/gas partition coefficient (QPlogPw)18.854
    Predicted octanol/water partition coefficient (QPlogPo/w)0.79
    Predicted aqueous solubility (QPlogS)-3.705
    Conformation-independent predicted aqueous solubility (CIQPlogS)-4.478
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.138
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)1.64
    Predicted brain/blood partition coefficient (QPlogBB)-3.698
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)0.614
    Predicted skin permeability, log Kp (QPlogKp)-6.481
    PM3 calculated ionization potential (IP(ev))9.432
    PM3 calculated electron affinity (EA(eV))0.848
    Number of likely metabolic reactions (#metab)12
    Prediction of binding to human serum albumin (QPlogKhsa)-0.718
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)22.461
    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)222.459
    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
    P04818TYMSThymidylate synthase (by homology)T98397SwissTargetPrediction
    Q96KS0EIT6HIF-prolyl hydroxylase 1T53904SwissTargetPrediction
    P05067APPBeta amyloid A4 proteinT87024SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P08473MMENeprilysinT05409SwissTargetPrediction
    Q9UHC9NPC1L1Niemann-Pick C1-like protein 1T33901SwissTargetPrediction
    Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
    P11309PIM1Serine/threonine-protein kinase PIM1T50594SwissTargetPrediction
    Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
    P04035HMGCRHMG-CoA reductaseT53585SwissTargetPrediction
    P29466CASP1Caspase-1T98269SwissTargetPrediction
    P06756ITGAVVitronectin receptor alphaT67103SwissTargetPrediction
    P52789HK2Hexokinase type IIT96685SwissTargetPrediction
    Q99558MAP3K14Mitogen-activated protein kinase kinase kinase 14T95736SwissTargetPrediction
    P42574CASP3Caspase-3T57943SwissTargetPrediction
    P55210CASP7Caspase-7T72252SwissTargetPrediction
    P55212CASP6Caspase-6T20600SwissTargetPrediction
    Q9UQ81MCH5Caspase-8T15700SwissTargetPrediction
    O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
    P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction and SEA
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction and SEA
    P53350PLK1Serine/threonine-protein kinase PLK1T40694SwissTargetPrediction
    P68400CSNK2A1Casein kinase II alphaT51565SwissTargetPrediction
    P28074PSMB5Proteasome Macropain subunit MB1T49031SwissTargetPrediction
    P00374DHFRDihydrofolate reductaseT17345SwissTargetPrediction
    P53396ACLYATP-citrate synthaseT52189SwissTargetPrediction
    P22102GARTGAR transformylaseT72042SwissTargetPrediction
    P15328FOLR1Folate receptor alphaT83386SwissTargetPrediction
    Q15393SF3B3Splicing factor 3B subunit 3T96723SwissTargetPrediction
    Q92887CMOATMultidrug resistance-associated protein 2T61792SEA
    Q9GZT9EGLN1Egl nine homolog 1T32880SwissTargetPrediction

    Target associated diseases

    TTD_ID Disease_ID Disease name ICD_11 Uniprot ID Gene names
    T98397DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P04818TYMS
    T98397DI0395Stomach cancer[ICD-11: 2B72]P04818TYMS
    T53904DI0010Acute disease anaemia[ICD-11: 3A90]Q96KS0EIT6
    T87024DI0025Alzheimer disease[ICD-11: 8A20]P05067APP
    T87024DI0122Diagnostic imaging[ICD-11: N.A.]P05067APP
    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
    T33901DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]Q9UHC9NPC1L1
    T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
    T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
    T50594DI0012Acute myeloid leukaemia[ICD-11: 2A60]P11309PIM1
    T50594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11309PIM1
    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
    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
    T67103DI0095Colorectal cancer[ICD-11: 2B91]P06756ITGAV
    T67103DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06756ITGAV
    T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
    T57943DI0060Brain cancer[ICD-11: 2A00]P42574CASP3
    T72252DI0110Cystic fibrosis[ICD-11: CA25]P55210CASP7
    T15700DI0120Diabetes mellitus[ICD-11: 5A10]Q9UQ81MCH5
    T15700DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UQ81MCH5
    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
    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
    T40694DI0012Acute myeloid leukaemia[ICD-11: 2A60]P53350PLK1
    T40694DI0284Myelodysplastic syndrome[ICD-11: 2A37]P53350PLK1
    T40694DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P53350PLK1
    T51565DI0104Coronavirus infection[ICD-11: 1D92]P68400CSNK2A1
    T51565DI0235Liver cancer[ICD-11: 2C12]P68400CSNK2A1
    T51565DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P68400CSNK2A1
    T17345DI0207Indeterminate colitis[ICD-11: DD72]P00374DHFR
    T17345DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P00374DHFR
    T17345DI0416Tuberculosis[ICD-11: 1B10-1B12]P00374DHFR
    T17345DI0427Urinary tract infection[ICD-11: GC08]P00374DHFR
    T52189DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P53396ACLY
    T72042DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P22102GART
    T83386DI0243Malaria[ICD-11: 1F40-1F45]P15328FOLR1
    T83386DI0321Ovarian cancer[ICD-11: 2C73]P15328FOLR1
    T96723DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q15393SF3B3
    T96723DI0085Chronic myelomonocytic leukaemia[ICD-11: 2A40]Q15393SF3B3
    T96723DI0284Myelodysplastic syndrome[ICD-11: 2A37]Q15393SF3B3

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