Fibraurinoside



Compound IDCDAMM00530
Common nameFibraurinoside
IUPAC name5-(furan-3-yl)-3,11-dimethyl-12-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6,14,16-trioxapentacyclo[10.3.2.02,11.03,8.013,15]heptadec-8-ene-7,17-dione
Molecular formulaC26H30O12

Experimental data

Retention time13.31
Adduct[M+H]+
Actual mz535.186
Theoretical mz535.181
Error8.08
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score7.912

Identifiers and class information

Inchi keyPPILOQQTEQXAMT-UHFFFAOYNA-N
SmilesO=C1OC(C2=COC=C2)CC3(C1=CCC4(C)C3C5OC(=O)C4(OC6OC(CO)C(O)C(O)C6O)C7OC57)C
SuperclassLipids and lipid-like molecules
ClassFatty Acyls

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)3
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)534.516
    Computed dipole moment(dipole)6.847
    Total solvent accessible surface area (SASA)648.061
    Hydrophobic component of SASA (FOSA)283.637
    Hydrophilic component of SASA (FISA)211.033
    Pie component of the SASA (PISA)153.392
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1327.32
    Number of hydrogen bond donors (donorHB)4
    Number of hydrogen bond acceptors (accptHB)17.75
    Free energy of solvation of dipole (dip^2/V)0.0353187
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0547788
    Globularity descriptor (glob)0.901292
    Predicted polarizability in cubic angstroms (QPpolrz)43.935
    Predicted hexadecane/gas partition coefficient (QPlogPC16)14.021
    Predicted octanol/gas partition coefficient (QPlogPoct)30.961
    Predicted water/gas partition coefficient (QPlogPw)25.555
    Predicted octanol/water partition coefficient (QPlogPo/w)-0.74
    Predicted aqueous solubility (QPlogS)-1.934
    Conformation-independent predicted aqueous solubility (CIQPlogS)-3.524
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.861
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)98.782
    Predicted brain/blood partition coefficient (QPlogBB)-1.59
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)40.524
    Predicted skin permeability, log Kp (QPlogKp)-4.196
    PM3 calculated ionization potential (IP(ev))9.578
    PM3 calculated electron affinity (EA(eV))0.541
    Number of likely metabolic reactions (#metab)7
    Prediction of binding to human serum albumin (QPlogKhsa)-0.937
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)32.395
    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)187.521
    Number of nitrogen and oxygen atoms (#NandO)12
    Number of violations of Lipinski’s rule of five (RuleOfFive)2
    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
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    P08473MMENeprilysinT05409SwissTargetPrediction
    P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
    P13726F3Coagulation factor VII/tissue factorT72702SwissTargetPrediction
    Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
    P41145OPRK1Kappa Opioid receptorT60693SwissTargetPrediction
    P04626ERBB2Receptor protein-tyrosine kinase erbB-2T14597SwissTargetPrediction
    Q16831UPP1Uridine phosphorylase 1 (by homology)T97388SwissTargetPrediction
    P11387TOP1DNA topoisomerase IT09826SwissTargetPrediction
    Q02750MAP2K1Dual specificity mitogen-activated protein kinase kinase 1T99057SwissTargetPrediction
    P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
    P55263ADKAdenosine kinaseT91661SwissTargetPrediction
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
    O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P06737PYGLLiver glycogen phosphorylaseT19184SwissTargetPrediction
    P25025CXCR2Interleukin-8 receptor BT56923SwissTargetPrediction
    P17936IGFBP3Insulin-like growth factor binding protein 3T33455SwissTargetPrediction
    P17931LGALS3Galectin-3T72038SwissTargetPrediction
    P14679TYRTyrosinaseT97035SwissTargetPrediction
    P09382LGALS1Galectin-1T09544SwissTargetPrediction

    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
    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
    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
    T35734DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P34913EPHX2
    T35734DI0190Hypertension[ICD-11: BA00-BA04]P34913EPHX2
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T72702DI0075Cervical cancer[ICD-11: 2C77]P13726F3
    T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
    T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
    T60693DI0304Non-specific cutaneous vascular symptom[ICD-11: ME64]P41145OPRK1
    T60693DI0324Pain[ICD-11: MG30-MG3Z]P41145OPRK1
    T60693DI0349Pruritus[ICD-11: EC90]P41145OPRK1
    T14597DI0062Breast cancer[ICD-11: 2C60-2C6Y]P04626ERBB2
    T14597DI0238Lung cancer[ICD-11: 2C25]P04626ERBB2
    T14597DI0346Prostate cancer[ICD-11: 2C82]P04626ERBB2
    T97388DI0292Nasopharyngitis[ICD-11: CA00]Q16831UPP1
    T09826DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P11387TOP1
    T09826DI0095Colorectal cancer[ICD-11: 2B91]P11387TOP1
    T09826DI0238Lung cancer[ICD-11: 2C25]P11387TOP1
    T09826DI0321Ovarian cancer[ICD-11: 2C73]P11387TOP1
    T09826DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11387TOP1
    T99057DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]Q02750MAP2K1
    T99057DI0336Phakomatoses/hamartoneoplastic syndrome[ICD-11: LD2D]Q02750MAP2K1
    T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
    T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
    T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
    T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
    T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
    T56923DI0155Fungal infection[ICD-11: 1F29-1F2F]P25025CXCR2
    T56923DI0324Pain[ICD-11: MG30-MG3Z]P25025CXCR2
    T33455DI0115Dementia[ICD-11: 6D80-6D8Z]P17936IGFBP3
    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

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