Pikuroside



Compound IDCDAMM01197
Common namePikuroside
IUPAC name[4,5-dihydroxy-9-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,10-dioxatricyclo[5.3.1.04,8]undecan-6-yl] 4-hydroxy-3-methoxybenzoate
Molecular formulaC23H30O14

Experimental data

Retention time0.36
Adduct[M+K]+
Actual mz569.126
Theoretical mz569.127
Error2.03
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.9011

Identifiers and class information

Inchi keyDTNNYXMHYVWWHO-YSGOKWCFNA-N
SmilesO=C(OC1C(O)C2(O)COC3OC(OC4OC(CO)C(O)C(O)C4O)C2C1C3)C5=CC=C(O)C(OC)=C5
SuperclassPhenylpropanoids and polyketides
ClassTannins

Pharmacokinetic properties

Number of descriptor values(#stars)5
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)13
Number of reactive functional groups (#rtvFG)4
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)530.482
Computed dipole moment(dipole)5.528
Total solvent accessible surface area (SASA)761.903
Hydrophobic component of SASA (FOSA)334.733
Hydrophilic component of SASA (FISA)323.797
Pie component of the SASA (PISA)103.374
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1430.77
Number of hydrogen bond donors (donorHB)7
Number of hydrogen bond acceptors (accptHB)19.55
Free energy of solvation of dipole (dip^2/V)0.0213603
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0678885
Globularity descriptor (glob)0.805955
Predicted polarizability in cubic angstroms (QPpolrz)43.745
Predicted hexadecane/gas partition coefficient (QPlogPC16)16.123
Predicted octanol/gas partition coefficient (QPlogPoct)35.973
Predicted water/gas partition coefficient (QPlogPw)31.099
Predicted octanol/water partition coefficient (QPlogPo/w)-2.099
Predicted aqueous solubility (QPlogS)-2.277
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.573
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.165
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)8.42
Predicted brain/blood partition coefficient (QPlogBB)-3.543
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)2.831
Predicted skin permeability, log Kp (QPlogKp)-5.875
PM3 calculated ionization potential (IP(ev))8.835
PM3 calculated electron affinity (EA(eV))1.275
Number of likely metabolic reactions (#metab)8
Prediction of binding to human serum albumin (QPlogKhsa)-1.359
Predicted qualitative human oral absorption (HumanOralAbsorption)1
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)0
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)212.688
Number of nitrogen and oxygen atoms (#NandO)14
Number of violations of Lipinski’s rule of five (RuleOfFive)3
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
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
P17706PTPN2T-cell protein-tyrosine phosphataseT49156SwissTargetPrediction
Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
Q14534SQLESqualene monooxygenase (by homology)T93344SwissTargetPrediction
P05121SERPINE1Plasminogen activator inhibitor-1T15556SwissTargetPrediction
P56817BACE1Beta-secretase 1T79031SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
P00742F10Thrombin and coagulation factor XT84631SwissTargetPrediction
P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
P01375TNFTNF-alphaT20178SwissTargetPrediction
P15692VEGFAVascular endothelial growth factor AT20761SEA
P05230FGF1Acidic fibroblast growth factorT18639SEA
P09038FGF2Basic fibroblast growth factorT31621SEA
P52789HK2Hexokinase type IIT96685SwissTargetPrediction
P16109SELPP-selectinT10965SEA
P14151SELLLeukocyte adhesion molecule-1T60526SEA
P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction
P60568IL2Interleukin-2T61698SwissTargetPrediction and SEA
Q9NUW8TDP1Tyrosyl-DNA phosphodiesterase 1T33492SwissTargetPrediction and SEA
P17931LGALS3Galectin-3T72038SwissTargetPrediction and SEA
P04746AMY2APancreatic alpha-amylaseT86918SwissTargetPrediction and SEA
P14679TYRTyrosinaseT97035SEA
P09382LGALS1Galectin-1T09544SEA
Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA
P05231IL6Interleukin-6T32578SEA

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
T36059DI0351Psoriasis[ICD-11: EA90]P0DMS8ADORA3
T36059DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P0DMS8ADORA3
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
T16347DI0009Acute diabete complication[ICD-11: 5A2Y]P18031PTPN1
T16347DI0062Breast cancer[ICD-11: 2C60-2C6Y]P18031PTPN1
T16347DI0308Obesity[ICD-11: 5B80-5B81]P18031PTPN1
T16347DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P18031PTPN1
T49156DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P17706PTPN2
T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T93344DI0118Dermatophytosis[ICD-11: 1F28]Q14534SQLE
T93344DI0385Skin fungal infection disorder[ICD-11: EA60]Q14534SQLE
T15556DI0037Asthma[ICD-11: CA23]P05121SERPINE1
T15556DI0405Thrombosis[ICD-11: DB61-GB90]P05121SERPINE1
T79031DI0025Alzheimer disease[ICD-11: 8A20]P56817BACE1
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
T84631DI0053Blood-forming organ disease[ICD-11: 3C0Z]P00742F10
T84631DI0080Christmas disease[ICD-11: 3B11]P00742F10
T84631DI0091Coagulation defect[ICD-11: 3B10]P00742F10
T84631DI0103Coronary thrombosis[ICD-11: BA43]P00742F10
T84631DI0114Deep vein thrombosis[ICD-11: BD71]P00742F10
T84631DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P00742F10
T84631DI0405Thrombosis[ICD-11: DB61-GB90]P00742F10
T84631DI0433Venous thromboembolism[ICD-11: BD72]P00742F10
T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
T20178DI0035Arterial occlusive disease[ICD-11: BD40]P01375TNF
T20178DI0274Multiple myeloma[ICD-11: 2A83]P01375TNF
T20178DI0351Psoriasis[ICD-11: EA90]P01375TNF
T20178DI0366Rheumatoid arthritis[ICD-11: FA20]P01375TNF
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
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
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
T32578DI0028Anemia[ICD-11: 3A00-3A9Z]P05231IL6

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