Isopentenyladenine-9-glucoside



Compound IDCDAMM01115
Common nameIsopentenyladenine-9-glucoside
IUPAC name2-(hydroxymethyl)-6-[6-(3-methylbut-2-enylamino)purin-9-yl]oxane-3,4,5-triol
Molecular formulaC16H23N5O5

Experimental data

Retention time11.41
Adduct[M+H]+
Actual mz366.177
Theoretical mz366.177
Error0.21
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.8978

Identifiers and class information

Inchi keyXEHLLUQVSRLWMH-RSCVUNFINA-N
SmilesOCC1OC(N2C=NC=3C(=NC=NC32)NCC=C(C)C)C(O)C(O)C1O
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Pharmacokinetic properties

Number of descriptor values(#stars)1
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)8
Number of reactive functional groups (#rtvFG)0
Predicted central nervous system activity (CNS)-2
Molecular weight (mol_MW)365.388
Computed dipole moment(dipole)2.408
Total solvent accessible surface area (SASA)656.499
Hydrophobic component of SASA (FOSA)314.484
Hydrophilic component of SASA (FISA)226.417
Pie component of the SASA (PISA)115.597
Weakly polar component of the SASA (WPSA)0
Total solvent accesible volume (volume)1140.9
Number of hydrogen bond donors (donorHB)5
Number of hydrogen bond acceptors (accptHB)12.5
Free energy of solvation of dipole (dip^2/V)0.0050819
Index of cohesive interaction in solids (ACxDN^.5/SA)0.0425756
Globularity descriptor (glob)0.804322
Predicted polarizability in cubic angstroms (QPpolrz)35.472
Predicted hexadecane/gas partition coefficient (QPlogPC16)12.358
Predicted octanol/gas partition coefficient (QPlogPoct)25.741
Predicted water/gas partition coefficient (QPlogPw)21.496
Predicted octanol/water partition coefficient (QPlogPo/w)-0.392
Predicted aqueous solubility (QPlogS)-3.058
Conformation-independent predicted aqueous solubility (CIQPlogS)-2.457
Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.25
Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)70.598
Predicted brain/blood partition coefficient (QPlogBB)-2.252
Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)28.186
Predicted skin permeability, log Kp (QPlogKp)-4.517
PM3 calculated ionization potential (IP(ev))8.352
PM3 calculated electron affinity (EA(eV))0.235
Number of likely metabolic reactions (#metab)9
Prediction of binding to human serum albumin (QPlogKhsa)-0.831
Predicted qualitative human oral absorption (HumanOralAbsorption)2
Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)57.742
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)144.378
Number of nitrogen and oxygen atoms (#NandO)10
Number of violations of Lipinski’s rule of five (RuleOfFive)0
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
Q86X55CARM1Histone-arginine methyltransferase CARM1T12837SwissTargetPrediction
P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction and SEA
P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction and SEA
P07327ADH1AAlcohol dehydrogenase alpha chainT65570SEA
O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction and SEA
P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
P27487DPP4Dipeptidyl peptidase IVT31391SwissTargetPrediction
P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
P08473MMENeprilysinT05409SwissTargetPrediction
Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
P15121AKR1B1Aldose reductaseT26623SwissTargetPrediction
P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction and SEA
P43235CTSKCathepsin KT11388SwissTargetPrediction
P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
Q16831UPP1Uridine phosphorylase 1 (by homology)T97388SwissTargetPrediction
P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
P07711CTSLCathepsin LT98691SwissTargetPrediction
P23946CMA1ChymaseT05114SwissTargetPrediction
P30556AGTR1Type-1 angiotensin II receptorT74456SwissTargetPrediction
Q02750MAP2K1Dual specificity mitogen-activated protein kinase kinase 1T99057SwissTargetPrediction
Q15078CDK5R1Cyclin-dependent kinase 5/CDK5 activator 1T09513SEA
P25774CTSSCathepsin ST68290SwissTargetPrediction
P26358DNMT1DNA (cytosine-5)-methyltransferase 1 (by homology)T88304SEA
P32320CDACytidine deaminase (by homology)T79027SEA
P00813ADAAdenosine deaminaseT03661SEA
P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
P42892ECE1Endothelin-converting enzyme 1T50970SwissTargetPrediction
P55263ADKAdenosine kinaseT91661SwissTargetPrediction and SEA
O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
P04406GAPDHGlyceraldehyde-3-phosphate dehydrogenase liverT39321SwissTargetPrediction and SEA
Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction and SEA
P25101EDNRAEndothelin receptor ET-AT23499SwissTargetPrediction
P52789HK2Hexokinase type IIT96685SwissTargetPrediction
P11021HSPA578 kDa glucose-regulated proteinT77594SwissTargetPrediction
O43868SLC28A2Sodium/nucleoside cotransporter 2T94627SwissTargetPrediction and SEA
P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
P23526AHCYAdenosylhomocysteinaseT68698SEA
Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
O76074PDE5APhosphodiesterase 5AT07663SwissTargetPrediction
P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SwissTargetPrediction and SEA
P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SEA
P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SEA
Q9H244P2RY12Purinergic receptor P2Y12 (by homology)T46937SEA
P17931LGALS3Galectin-3T72038SwissTargetPrediction
P19971TYMPThymidine phosphorylaseT59929SEA
P04746AMY2APancreatic alpha-amylaseT86918SEA
P11166SLC2A1Glucose transporter (by homology)T89458SwissTargetPrediction
Q8TEK3DOT1LHistone-lysine N-methyltransferase, H3 lysine-79 specificT87686SEA
P17612PRKACAcAMP-dependent protein kinase alpha-catalytic subunitT12808SEA
P55786NPEPPSPuromycin-sensitive aminopeptidaseT15610SEA
P47900P2RY1Purinergic receptor P2Y1T67818SEA
P41231P2RY2Purinergic receptor P2Y2T93515SEA
Q15077P2RY6Pyrimidinergic receptor P2Y6T90782SEA
P63000RAC1Ras-related C3 botulinum toxin substrate 1T88752SEA
Q15910EZH2EZH2/SUZ12/EED/RBBP7/RBBP4T25265SEA
Q99873PRMT1Protein-arginine N-methyltransferase 1T16808SwissTargetPrediction and SEA
Q96KQ7EHMT2Histone-lysine N-methyltransferase, H3 lysine-9 specific 3T53251SEA
P20248CCNA2CDK2/Cyclin AT58470SEA
P16885PLCG2Phospholipase C-gamma-2T93922SEA
P23919DTYMKThymidylate kinaseT94400SEA
Q9H9B1EHMT1Histone-lysine N-methyltransferase, H3 lysine-9 specific 5T39996SEA
Q9UBC3DNMT3BDNA (cytosine-5)-methyltransferase 3BT65501SEA
Q15391P2RY14Purinergic receptor P2Y14T16555SEA
Q05823RNASELRNase LT25200SEA
P51575P2RX1P2X purinoceptor 1T69091SEA
P17707AMD1S-adenosylmethionine decarboxylase 1T55922SwissTargetPrediction and SEA
Q8WTS6SETD7Histone-lysine N-methyltransferase SETD7T73184SwissTargetPrediction and SEA
Q9NVM4PRMT7Protein arginine N-methyltransferase 7T79501SEA
Q9BYW2SETD2Histone-lysine N-methyltransferase SETD2T73551SwissTargetPrediction
O43463SUV39H1Histone-lysine N-methyltransferase SUV39H1T39519SEA
Q92800EZH1Histone-lysine N-methyltransferase EZH1T17986SEA
Q99571P2RX4P2X purinoceptor 4T60330SEA
Q13304GPR17Uracil nucleotide/cysteinyl leukotriene receptorT33902SEA
Q86Y97KMT5CHistone-lysine N-methyltransferase KMT5CT68490SEA
Q9NZ70TAK1TGF-beta-activated kinase 1T04361SEA
Q9Y4W7PARGPoly(ADP-ribose) glycohydrolaseT66935SEA
Q07108CD69Early activation antigen CD69T48780SEA

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
T65570DI0139Exposure to noxious substances harmful effect[ICD-11: NE61]P07327ADH1A
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
T31391DI0009Acute diabete complication[ICD-11: 5A2Y]P27487DPP4
T31391DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P27487DPP4
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
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
T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
T11388DI0237Low bone mass disorder[ICD-11: FB83]P43235CTSK
T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
T97388DI0292Nasopharyngitis[ICD-11: CA00]Q16831UPP1
T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
T98691DI0263Middle East Respiratory Syndrome[ICD-11: 1D64]P07711CTSL
T98691DI0376Severe acute respiratory syndrome[ICD-11: 1D65]P07711CTSL
T05114DI0039Atopic eczema[ICD-11: EA80]P23946CMA1
T05114DI0086Chronic obstructive pulmonary disease[ICD-11: CA22]P23946CMA1
T05114DI0169Gram-positive bacterial infection[ICD-11: 1B74-1F40]P23946CMA1
T05114DI0175Heart failure[ICD-11: BD10-BD1Z]P23946CMA1
T05114DI0229Left ventricular failure[ICD-11: BD11]P23946CMA1
T05114DI0287Myocardial infarction[ICD-11: BA41-BA43]P23946CMA1
T74456DI0137Essential hypertension[ICD-11: BA00]P30556AGTR1
T74456DI0190Hypertension[ICD-11: BA00-BA04]P30556AGTR1
T74456DI0373Secondary hypertension[ICD-11: BA04]P30556AGTR1
T74456DI0425Urinary system clinical symptom[ICD-11: MF8Y]P30556AGTR1
T99057DI0262Metastatic tumour[ICD-11: 2D50-2E2Z]Q02750MAP2K1
T99057DI0336Phakomatoses/hamartoneoplastic syndrome[ICD-11: LD2D]Q02750MAP2K1
T68290DI0042Autoimmune disease[ICD-11: 4A40-4A45]P25774CTSS
T68290DI0092Coeliac disease[ICD-11: DA95]P25774CTSS
T68290DI0107Crohn disease[ICD-11: DD70]P25774CTSS
T68290DI0120Diabetes mellitus[ICD-11: 5A10]P25774CTSS
T68290DI0163General pain disorder[ICD-11: 8E43]P25774CTSS
T68290DI0324Pain[ICD-11: MG30-MG3Z]P25774CTSS
T68290DI0382Sjogren syndrome[ICD-11: 4A43]P25774CTSS
T88304DI0012Acute myeloid leukaemia[ICD-11: 2A60]P26358DNMT1
T88304DI0284Myelodysplastic syndrome[ICD-11: 2A37]P26358DNMT1
T88304DI0286Myeloproliferative neoplasm[ICD-11: 2A20]P26358DNMT1
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
T84173DI0257Metabolic disorder[ICD-11: 5C50-5D2Z]P04062GBA
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
T23499DI0070Cardiovascular disease[ICD-11: BA00-BE2Z]P25101EDNRA
T23499DI0356Pulmonary hypertension[ICD-11: BB01]P25101EDNRA
T23499DI0425Urinary system clinical symptom[ICD-11: MF8Y]P25101EDNRA
T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
T77594DI0252Melanoma[ICD-11: 2C30]P11021HSPA5
T77594DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P11021HSPA5
T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
T22583DI0009Acute diabete complication[ICD-11: 5A2Y]Q9NY91SLC5A4
T22583DI0417Type 2 diabetes mellitus[ICD-11: 5A11]Q9NY91SLC5A4
T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
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
T24587DI0369Sarcoma[ICD-11: 2A60-2C35]P16455MGMT
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
T46937DI0287Myocardial infarction[ICD-11: BA41-BA43]Q9H244P2RY12
T46937DI0405Thrombosis[ICD-11: DB61-GB90]Q9H244P2RY12
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
T59929DI0117Depression[ICD-11: 6A70-6A7Z]P19971TYMP
T86918DI0110Cystic fibrosis[ICD-11: CA25]P04746AMY2A
T86918DI0328Pancreatic malfunction[ICD-11: DC30-DC3Z]P04746AMY2A
T89458DI0384Skin disease[ICD-11: EA00-EM0Z]P11166SLC2A1
T87686DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q8TEK3DOT1L
T87686DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q8TEK3DOT1L
T87686DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q8TEK3DOT1L
T12808DI0279Muscular atrophy[ICD-11: 8B61]P17612PRKACA
T15610DI0012Acute myeloid leukaemia[ICD-11: 2A60]P55786NPEPPS
T15610DI0284Myelodysplastic syndrome[ICD-11: 2A37]P55786NPEPPS
T93515DI0436Visual system disease[ICD-11: 9E1Z]P41231P2RY2
T90782DI0025Alzheimer disease[ICD-11: 8A20]Q15077P2RY6
T88752DI0025Alzheimer disease[ICD-11: 8A20]P63000RAC1
T25265DI0151Follicular lymphoma[ICD-11: 2A80]Q15910EZH2
T16808DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q99873PRMT1
T53251DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q96KQ7EHMT2
T53251DI0339Postoperative inflammation[ICD-11: 1A00-CA43]Q96KQ7EHMT2
T53251DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q96KQ7EHMT2
T58470DI0363Retina cancer[ICD-11: 2D02]P20248CCNA2
T39996DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q9H9B1EHMT1
T39996DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9H9B1EHMT1
T65501DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q9UBC3DNMT3B
T55922DI0004Acidosis[ICD-11: 5C73]P17707AMD1
T73184DI0062Breast cancer[ICD-11: 2C60-2C6Y]Q8WTS6SETD7
T17986DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q92800EZH1
T17986DI0238Lung cancer[ICD-11: 2C25]Q92800EZH1
T17986DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q92800EZH1
T17986DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q92800EZH1
T17986DI0251Mature T-cell lymphoma[ICD-11: 2A90]Q92800EZH1
T17986DI0361Renal cell carcinoma[ICD-11: 2C90]Q92800EZH1
T17986DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]Q92800EZH1
T17986DI0423Ureteral cancer[ICD-11: 2C92]Q92800EZH1
T04361DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q9NZ70TAK1

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