Cis-zeatin-7-N-glucoside



Compound IDCDAMM00502
Common nameCis-zeatin-7-N-glucoside
IUPAC name2-(hydroxymethyl)-6-[6-[(4-hydroxy-3-methylbut-2-enyl)amino]purin-7-yl]oxane-3,4,5-triol
Molecular formulaC16H23N5O6

Experimental data

Retention time11
Adduct[M+H]+
Actual mz382.173
Theoretical mz382.172
Error1.11
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score8.3178

Identifiers and class information

Inchi keyHTDHRCLVWUEXIS-HNVSNYHQSA-N
SmilesOCC(=CCNC1=NC=NC=2N=CN(C21)C3OC(CO)C(O)C(O)C3O)C
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Piper longum L.

    • 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)10
    Number of reactive functional groups (#rtvFG)0
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)381.388
    Computed dipole moment(dipole)8.139
    Total solvent accessible surface area (SASA)642.89
    Hydrophobic component of SASA (FOSA)266.128
    Hydrophilic component of SASA (FISA)265.537
    Pie component of the SASA (PISA)111.224
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1147.78
    Number of hydrogen bond donors (donorHB)6
    Number of hydrogen bond acceptors (accptHB)14.2
    Free energy of solvation of dipole (dip^2/V)0.0577147
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0541037
    Globularity descriptor (glob)0.824644
    Predicted polarizability in cubic angstroms (QPpolrz)34.421
    Predicted hexadecane/gas partition coefficient (QPlogPC16)12.893
    Predicted octanol/gas partition coefficient (QPlogPoct)28.669
    Predicted water/gas partition coefficient (QPlogPw)24.398
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.239
    Predicted aqueous solubility (QPlogS)-2.335
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.163
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-4.9
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)30.048
    Predicted brain/blood partition coefficient (QPlogBB)-2.642
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)11.195
    Predicted skin permeability, log Kp (QPlogKp)-5.061
    PM3 calculated ionization potential (IP(ev))8.637
    PM3 calculated electron affinity (EA(eV))0.486
    Number of likely metabolic reactions (#metab)9
    Prediction of binding to human serum albumin (QPlogKhsa)-1.035
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)20.223
    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)164.439
    Number of nitrogen and oxygen atoms (#NandO)11
    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
    P29274ADORA2AAdenosine A2a receptorT77365SwissTargetPrediction and SEA
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction and SEA
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction and SEA
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    P10253GAALysosomal alpha-glucosidase (by homology)T31514SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    P08473MMENeprilysinT05409SwissTargetPrediction
    P34913EPHX2Epoxide hydrataseT35734SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
    P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
    P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction and SEA
    P35354PTGS2Cyclooxygenase-2T66665SwissTargetPrediction
    P04183TK1Thymidine kinase, cytosolicT30081SwissTargetPrediction
    P18031PTPN1Protein-tyrosine phosphatase 1BT16347SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P08254MMP3Matrix metalloproteinase 3T86702SwissTargetPrediction
    P14780MMP9Matrix metalloproteinase 9T54156SwissTargetPrediction
    Q13547HDAC1Histone deacetylase 1T68547SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P24941CDK2Cyclin-dependent kinase 2T70176SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P78536ADAM17ADAM17T82393SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    P49841GSK3BGlycogen synthase kinase-3 betaT70977SwissTargetPrediction
    P53779MAPK10c-Jun N-terminal kinase 3T85421SwissTargetPrediction
    P26358DNMT1DNA (cytosine-5)-methyltransferase 1 (by homology)T88304SEA
    P32320CDACytidine deaminase (by homology)T79027SEA
    P00813ADAAdenosine deaminaseT03661SwissTargetPrediction and SEA
    P04062GBABeta-glucocerebrosidaseT84173SwissTargetPrediction
    P55263ADKAdenosine kinaseT91661SwissTargetPrediction and SEA
    O60502OGABifunctional protein NCOATT19567SwissTargetPrediction
    P11142HSPA8Heat shock cognate 71 kDa proteinT12817SwissTargetPrediction
    P06493CDK1Cyclin-dependent kinase 1/cyclin B1T49898SwissTargetPrediction
    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 2T94627SEA
    P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
    P23526AHCYAdenosylhomocysteinaseT68698SwissTargetPrediction and SEA
    Q9NY91SLC5A4Low affinity sodium-glucose cotransporterT22583SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction
    P17931LGALS3Galectin-3T72038SwissTargetPrediction
    P14679TYRTyrosinaseT97035SwissTargetPrediction
    Q8TEK3DOT1LHistone-lysine N-methyltransferase, H3 lysine-79 specificT87686SEA
    P55786NPEPPSPuromycin-sensitive aminopeptidaseT15610SEA
    P47900P2RY1Purinergic receptor P2Y1T67818SEA
    P41231P2RY2Purinergic receptor P2Y2T93515SEA
    Q99873PRMT1Protein-arginine N-methyltransferase 1T16808SEA
    Q96KQ7EHMT2Histone-lysine N-methyltransferase, H3 lysine-9 specific 3T53251SEA
    P16885PLCG2Phospholipase C-gamma-2T93922SEA
    Q9H9B1EHMT1Histone-lysine N-methyltransferase, H3 lysine-9 specific 5T39996SEA
    Q9UBC3DNMT3BDNA (cytosine-5)-methyltransferase 3BT65501SEA
    P51575P2RX1P2X purinoceptor 1T69091SEA
    P17707AMD1S-adenosylmethionine decarboxylase 1T55922SEA
    Q8WTS6SETD7Histone-lysine N-methyltransferase SETD7T73184SwissTargetPrediction and SEA
    Q9NVM4PRMT7Protein arginine N-methyltransferase 7T79501SEA
    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

    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
    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
    T31514DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]P10253GAA
    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
    T06569DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P23280CA6
    T06569DI0372Seborrhoeic dermatitis[ICD-11: EA81]P23280CA6
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T53378DI0046Bacterial infection[ICD-11: 1A00-1C4Z]P22748CA4
    T53378DI0166Glaucoma[ICD-11: 9C61]P22748CA4
    T53378DI0372Seborrhoeic dermatitis[ICD-11: EA81]P22748CA4
    T86679DI0180Herpes simplex infection[ICD-11: 1F00]P29275ADORA2B
    T86679DI0397Supraventricular tachyarrhythmia[ICD-11: BC81]P29275ADORA2B
    T66665DI0087Chronic pain[ICD-11: MG30]P35354PTGS2
    T66665DI0145Female pelvic pain[ICD-11: GA34]P35354PTGS2
    T66665DI0188Hyper-lipoproteinaemia[ICD-11: 5C80]P35354PTGS2
    T66665DI0207Indeterminate colitis[ICD-11: DD72]P35354PTGS2
    T66665DI0227Knee osteoarthritis[ICD-11: FA01]P35354PTGS2
    T66665DI0320Osteoarthritis[ICD-11: FA00-FA05]P35354PTGS2
    T66665DI0324Pain[ICD-11: MG30-MG3Z]P35354PTGS2
    T66665DI0366Rheumatoid arthritis[ICD-11: FA20]P35354PTGS2
    T66665DI0416Tuberculosis[ICD-11: 1B10-1B12]P35354PTGS2
    T30081DI0012Acute myeloid leukaemia[ICD-11: 2A60]P04183TK1
    T30081DI0184Human immunodeficiency virus disease[ICD-11: 1C60-1C62]P04183TK1
    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
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    T86702DI0101Corneal disease[ICD-11: 9A76-9A78]P08254MMP3
    T86702DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P08254MMP3
    T86702DI0199Idiopathic interstitial pneumonitis[ICD-11: CB03]P08254MMP3
    T86702DI0275Multiple sclerosis[ICD-11: 8A40]P08254MMP3
    T86702DI0287Myocardial infarction[ICD-11: BA41-BA43]P08254MMP3
    T86702DI0320Osteoarthritis[ICD-11: FA00-FA05]P08254MMP3
    T86702DI0366Rheumatoid arthritis[ICD-11: FA20]P08254MMP3
    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
    T68547DI0274Multiple myeloma[ICD-11: 2A83]Q13547HDAC1
    T68547DI0283Mycosis fungoides[ICD-11: 2B01]Q13547HDAC1
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T70176DI0060Brain cancer[ICD-11: 2A00]P24941CDK2
    T70176DI0062Breast cancer[ICD-11: 2C60-2C6Y]P24941CDK2
    T70176DI0238Lung cancer[ICD-11: 2C25]P24941CDK2
    T70176DI0241Lymphoma[ICD-11: 2A80-2A86]P24941CDK2
    T70176DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P24941CDK2
    T70176DI0303Non-small-cell lung cancer[ICD-11: 2C25]P24941CDK2
    T70176DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P24941CDK2
    T70176DI0406Thymoma[ICD-11: 2C27]P24941CDK2
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T82393DI0062Breast cancer[ICD-11: 2C60-2C6Y]P78536ADAM17
    T82393DI0366Rheumatoid arthritis[ICD-11: FA20]P78536ADAM17
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    T70977DI0288Myotonic disorder[ICD-11: 8C71]P49841GSK3B
    T85421DI0125Dissociative neurological symptom disorder[ICD-11: 6B60]P53779MAPK10
    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
    T49898DI0062Breast cancer[ICD-11: 2C60-2C6Y]P06493CDK1
    T49898DI0238Lung cancer[ICD-11: 2C25]P06493CDK1
    T49898DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P06493CDK1
    T49898DI0250Mature B-cell lymphoma[ICD-11: 2A85]P06493CDK1
    T49898DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P06493CDK1
    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
    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
    T87686DI0012Acute myeloid leukaemia[ICD-11: 2A60]Q8TEK3DOT1L
    T87686DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]Q8TEK3DOT1L
    T87686DI0250Mature B-cell lymphoma[ICD-11: 2A85]Q8TEK3DOT1L
    T15610DI0012Acute myeloid leukaemia[ICD-11: 2A60]P55786NPEPPS
    T15610DI0284Myelodysplastic syndrome[ICD-11: 2A37]P55786NPEPPS
    T93515DI0436Visual system disease[ICD-11: 9E1Z]P41231P2RY2
    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
    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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