Mandelonitrile rutinoside



Compound IDCDAMM03015
Common nameMandelonitrile rutinoside
IUPAC name2-phenyl-2-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxyacetonitrile
Molecular formulaC20H27NO10

Experimental data

Retention time22.99
Adduct[M+H]+
Actual mz442.167
Theoretical mz442.17
Error7.64
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.3456

Identifiers and class information

Inchi keyQSPJUYWAUZTHLP-UHFFFAOYNA-N
SmilesN#CC(OC1OC(COC2OC(C)C(O)C(O)C2O)C(O)C(O)C1O)C=3C=CC=CC3
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Clitoria ternatea 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)13
    Number of reactive functional groups (#rtvFG)2
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)441.434
    Computed dipole moment(dipole)7.607
    Total solvent accessible surface area (SASA)720.381
    Hydrophobic component of SASA (FOSA)255.535
    Hydrophilic component of SASA (FISA)271.32
    Pie component of the SASA (PISA)193.526
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1306.67
    Number of hydrogen bond donors (donorHB)6
    Number of hydrogen bond acceptors (accptHB)18.5
    Free energy of solvation of dipole (dip^2/V)0.0442824
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.062905
    Globularity descriptor (glob)0.802378
    Predicted polarizability in cubic angstroms (QPpolrz)39.64
    Predicted hexadecane/gas partition coefficient (QPlogPC16)15.035
    Predicted octanol/gas partition coefficient (QPlogPoct)32.653
    Predicted water/gas partition coefficient (QPlogPw)28.757
    Predicted octanol/water partition coefficient (QPlogPo/w)-1.85
    Predicted aqueous solubility (QPlogS)-2.944
    Conformation-independent predicted aqueous solubility (CIQPlogS)-2.58
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-5.653
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)26.483
    Predicted brain/blood partition coefficient (QPlogBB)-3.03
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)9.767
    Predicted skin permeability, log Kp (QPlogKp)-4.59
    PM3 calculated ionization potential (IP(ev))9.896
    PM3 calculated electron affinity (EA(eV))0.032
    Number of likely metabolic reactions (#metab)8
    Prediction of binding to human serum albumin (QPlogKhsa)-1.469
    Predicted qualitative human oral absorption (HumanOralAbsorption)2
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)15.666
    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)181.539
    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
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P0DMS8ADORA3Adenosine A3 receptorT36059SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    O00754MAN2B1Lysosomal alpha-mannosidaseT63156SEA
    O43451MGAMMaltase-glucoamylaseT92777SwissTargetPrediction
    P13866SLC5A1Sodium/glucose cotransporter 1T54771SwissTargetPrediction
    P43166CA7Carbonic anhydrase VIIT37541SwissTargetPrediction
    P23280CA6Carbonic anhydrase VIT06569SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SwissTargetPrediction
    P22748CA4Carbonic anhydrase IVT53378SwissTargetPrediction
    P29275ADORA2BAdenosine A2b receptorT86679SwissTargetPrediction
    P00491PNPPurine nucleoside phosphorylaseT78198SwissTargetPrediction
    Q9BZP6CHIAAcidic mammalian chitinase (by homology)T51597SwissTargetPrediction
    Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
    P08253MMP2Matrix metalloproteinase 2T68251SwissTargetPrediction
    P22894MMP8Matrix metalloproteinase 8T08856SwissTargetPrediction
    P03956MMP1Matrix metalloproteinase 1T52450SwissTargetPrediction
    P23975SLC6A2Norepinephrine transporterT21945SwissTargetPrediction
    Q16539MAPK14MAP kinase p38 alphaT65864SwissTargetPrediction
    P45452MMP13Matrix metalloproteinase 13T34296SwissTargetPrediction
    P09237MMP7Matrix metalloproteinase 7T73475SwissTargetPrediction
    P07900HSP90AA1Heat shock protein HSP 90-alphaT18477SwissTargetPrediction
    P32320CDACytidine deaminase (by homology)T79027SwissTargetPrediction
    P00813ADAAdenosine deaminaseT03661SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SwissTargetPrediction and SEA
    P05230FGF1Acidic fibroblast growth factorT18639SwissTargetPrediction and SEA
    P09038FGF2Basic fibroblast growth factorT31621SwissTargetPrediction and SEA
    Q9Y251HPSEHeparanaseT47623SwissTargetPrediction
    P55263ADKAdenosine kinaseT91661SwissTargetPrediction
    Q99808SLC29A1Equilibrative nucleoside transporter 1T13491SwissTargetPrediction
    P52789HK2Hexokinase type IIT96685SwissTargetPrediction
    P39900MMP12Matrix metalloproteinase 12T03500SwissTargetPrediction
    P31639SLC5A2Sodium/glucose cotransporter 2T30085SwissTargetPrediction
    P35346SSTR5Somatostatin receptor 5T64830SwissTargetPrediction
    P30874SSTR2Somatostatin receptor 2T53024SwissTargetPrediction
    P31391SSTR4Somatostatin receptor 4T62974SwissTargetPrediction
    P30872SSTR1Somatostatin receptor 1T16633SwissTargetPrediction
    P32745SSTR3Somatostatin receptor 3T13644SwissTargetPrediction
    P16109SELPP-selectinT10965SEA
    P01112HRASTransforming protein p21/H-Ras-1T71081SwissTargetPrediction
    P16455MGMT6-O-methylguanine-DNA methyltransferaseT24587SwissTargetPrediction
    P20839IMPDH1Inosine-5'-monophosphate dehydrogenase 1T40111SwissTargetPrediction
    P12268IMPDH2Inosine-5'-monophosphate dehydrogenase 2T89360SwissTargetPrediction
    P17931LGALS3Galectin-3T72038SwissTargetPrediction
    P19971TYMPThymidine phosphorylaseT59929SwissTargetPrediction
    P04746AMY2APancreatic alpha-amylaseT86918SwissTargetPrediction and SEA
    P14679TYRTyrosinaseT97035SEA
    Q9GZQ4NMUR2Neuromedin-U receptor 2T04210SEA
    P11717IGF2RInsulin-like growth factor II receptorT59550SEA

    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
    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
    T63156DI0242Lysosomal disease[ICD-11: 5C56]O00754MAN2B1
    T92777DI0009Acute diabete complication[ICD-11: 5A2Y]O43451MGAM
    T92777DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]O43451MGAM
    T54771DI0120Diabetes mellitus[ICD-11: 5A10]P13866SLC5A1
    T54771DI0175Heart failure[ICD-11: BD10-BD1Z]P13866SLC5A1
    T54771DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P13866SLC5A1
    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
    T78198DI0120Diabetes mellitus[ICD-11: 5A10]P00491PNP
    T78198DI0167Gout[ICD-11: FA25]P00491PNP
    T78198DI0245Malignant haematopoietic neoplasm[ICD-11: 2B33]P00491PNP
    T78198DI0283Mycosis fungoides[ICD-11: 2B01]P00491PNP
    T78198DI0351Psoriasis[ICD-11: EA90]P00491PNP
    T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
    T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
    T68251DI0238Lung cancer[ICD-11: 2C25]P08253MMP2
    T08856DI0366Rheumatoid arthritis[ICD-11: FA20]P22894MMP8
    T52450DI0238Lung cancer[ICD-11: 2C25]P03956MMP1
    T21945DI0013Acute pain[ICD-11: MG31]P23975SLC6A2
    T21945DI0040Attention deficit hyperactivity disorder[ICD-11: 6A05]P23975SLC6A2
    T21945DI0087Chronic pain[ICD-11: MG30]P23975SLC6A2
    T21945DI0101Corneal disease[ICD-11: 9A76-9A78]P23975SLC6A2
    T21945DI0117Depression[ICD-11: 6A70-6A7Z]P23975SLC6A2
    T21945DI0166Glaucoma[ICD-11: 9C61]P23975SLC6A2
    T21945DI0264Migraine[ICD-11: 8A80]P23975SLC6A2
    T21945DI0301Nicotine use disorder[ICD-11: 6C4A]P23975SLC6A2
    T21945DI0308Obesity[ICD-11: 5B80-5B81]P23975SLC6A2
    T21945DI0324Pain[ICD-11: MG30-MG3Z]P23975SLC6A2
    T21945DI0395Stomach cancer[ICD-11: 2B72]P23975SLC6A2
    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
    T34296DI0391Solid tumour/cancer[ICD-11: 2A00-2F9Z]P45452MMP13
    T73475DI0238Lung cancer[ICD-11: 2C25]P09237MMP7
    T18477DI0015Acute upper respiratory infection[ICD-11: CA07]P07900HSP90AA1
    T18477DI0037Asthma[ICD-11: CA23]P07900HSP90AA1
    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
    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
    T47623DI0020African trypanosomiasis[ICD-11: 1F51]Q9Y251HPSE
    T47623DI0310Ocular disease[ICD-11: N.A.]Q9Y251HPSE
    T91661DI0134Epilepsy/seizure[ICD-11: 8A61-8A6Z]P55263ADK
    T13491DI0030Angina pectoris[ICD-11: BA40]Q99808SLC29A1
    T96685DI0133Epidermal dysplasias[ICD-11: EK90]P52789HK2
    T03500DI0037Asthma[ICD-11: CA23]P39900MMP12
    T03500DI0238Lung cancer[ICD-11: 2C25]P39900MMP12
    T03500DI0361Renal cell carcinoma[ICD-11: 2C90]P39900MMP12
    T30085DI0120Diabetes mellitus[ICD-11: 5A10]P31639SLC5A2
    T30085DI0175Heart failure[ICD-11: BD10-BD1Z]P31639SLC5A2
    T30085DI0417Type 2 diabetes mellitus[ICD-11: 5A11]P31639SLC5A2
    T64830DI0108Cushing syndrome[ICD-11: 5A70]P35346SSTR5
    T53024DI0108Cushing syndrome[ICD-11: 5A70]P30874SSTR2
    T53024DI0122Diagnostic imaging[ICD-11: N.A.]P30874SSTR2
    T53024DI0337Pituitary gland disorder[ICD-11: 5A60-5A61]P30874SSTR2
    T62974DI0087Chronic pain[ICD-11: MG30]P31391SSTR4
    T62974DI0179Hepatitis virus infection[ICD-11: 1E50-1E51]P31391SSTR4
    T16633DI0108Cushing syndrome[ICD-11: 5A70]P30872SSTR1
    T16633DI0395Stomach cancer[ICD-11: 2B72]P30872SSTR1
    T13644DI0108Cushing syndrome[ICD-11: 5A70]P32745SSTR3
    T10965DI0088Circulatory system disease[ICD-11: BE2Z]P16109SELP
    T10965DI0381Sickle-cell disorder[ICD-11: 3A51]P16109SELP
    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
    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
    T97035DI0007Acquired hypermelanosis[ICD-11: ED60]P14679TYR
    T97035DI0008Acquired hypomelanotic disorder[ICD-11: ED63]P14679TYR
    T59550DI0146Fibrosis[ICD-11: GA14-GC01]P11717IGF2R
    T59550DI0368Sarcoidosis[ICD-11: 4B20]P11717IGF2R

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