Dide-O-methylsimmondsin



Compound IDCDAMM02926
Common nameDide-O-methylsimmondsin
IUPAC name2-[2,3,4-trihydroxy-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexylidene]acetonitrile
Molecular formulaC14H21NO9

Experimental data

Retention time22.98
Adduct[M+H]+
Actual mz348.131
Theoretical mz348.129
Error4.66
Ionizaton modePositive
Instrument typeLC-MS/MS-QTOF, spectrum predicted by MS-DIAL v4.9 integrated with MS-FINDER 3.60
Score6.7981

Identifiers and class information

Inchi keyMRQYIJOEUFLPMV-KTAJNNJTNA-N
SmilesN#CC=C1C(O)C(O)C(O)CC1OC2OC(CO)C(O)C(O)C2O
SuperclassOrganic oxygen compounds
ClassOrganooxygen compounds

Plant source

  • Clitoria ternatea L.

    • Pharmacokinetic properties

    Number of descriptor values(#stars)4
    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)11
    Number of reactive functional groups (#rtvFG)1
    Predicted central nervous system activity (CNS)-2
    Molecular weight (mol_MW)347.321
    Computed dipole moment(dipole)5.342
    Total solvent accessible surface area (SASA)568.76
    Hydrophobic component of SASA (FOSA)208.635
    Hydrophilic component of SASA (FISA)344.822
    Pie component of the SASA (PISA)15.303
    Weakly polar component of the SASA (WPSA)0
    Total solvent accesible volume (volume)1010.46
    Number of hydrogen bond donors (donorHB)7
    Number of hydrogen bond acceptors (accptHB)16.8
    Free energy of solvation of dipole (dip^2/V)0.0282462
    Index of cohesive interaction in solids (ACxDN^.5/SA)0.0781501
    Globularity descriptor (glob)0.856213
    Predicted polarizability in cubic angstroms (QPpolrz)27.368
    Predicted hexadecane/gas partition coefficient (QPlogPC16)11.753
    Predicted octanol/gas partition coefficient (QPlogPoct)28.929
    Predicted water/gas partition coefficient (QPlogPw)27.911
    Predicted octanol/water partition coefficient (QPlogPo/w)-3.295
    Predicted aqueous solubility (QPlogS)-2.409
    Conformation-independent predicted aqueous solubility (CIQPlogS)-1.426
    Predicted IC50 value for blockage of HERG K+ channels (QPlogHERG)-3.932
    Predicted apparent Caco-2 cell permeability in nm/sec (QPPCaco)5.32
    Predicted brain/blood partition coefficient (QPlogBB)-3.235
    Predicted apparent MDCK cell permeability in nm/sec (QPPMDCK)1.723
    Predicted skin permeability, log Kp (QPlogKp)-6.765
    PM3 calculated ionization potential (IP(ev))10.472
    PM3 calculated electron affinity (EA(eV))0.556
    Number of likely metabolic reactions (#metab)8
    Prediction of binding to human serum albumin (QPlogKhsa)-1.313
    Predicted qualitative human oral absorption (HumanOralAbsorption)1
    Predicted human oral absorption on 0 to 100% scale (PercentHumanOralAbsorption)7.684
    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)186.074
    Number of nitrogen and oxygen atoms (#NandO)10
    Number of violations of Lipinski’s rule of five (RuleOfFive)1
    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
    P30542ADORA1Adenosine A1 receptorT92072SwissTargetPrediction
    O43570CA12Carbonic anhydrase XIIT16987SwissTargetPrediction
    Q16790CA9Carbonic anhydrase IXT64567SwissTargetPrediction
    P00915CA1Carbonic anhydrase IT13201SwissTargetPrediction
    P00918CA2Carbonic anhydrase IIT20401SwissTargetPrediction
    O43451MGAMMaltase-glucoamylaseT92777SwissTargetPrediction
    Q9ULX7CA14Carbonic anhydrase XIVT31992SEA
    Q9BZP6CHIAAcidic mammalian chitinase (by homology)T51597SEA
    Q04609FOLH1Glutamate carboxypeptidase IIT97071SwissTargetPrediction
    P40763STAT3Signal transducer and activator of transcription 3T29130SwissTargetPrediction
    P15692VEGFAVascular endothelial growth factor AT20761SEA
    P05230FGF1Acidic fibroblast growth factorT18639SEA
    P09038FGF2Basic fibroblast growth factorT31621SEA
    Q15172PPP2R5ASerine/threonine protein phosphatase 2A, 56 kDa regulatory subunit, alpha isoformT57291SwissTargetPrediction
    P67775PPP2CASerine/threonine protein phosphatase 2A, catalytic subunit, alpha isoformT40491SwissTargetPrediction
    P17931LGALS3Galectin-3T72038SEA
    P04746AMY2APancreatic alpha-amylaseT86918SEA
    P14679TYRTyrosinaseT97035SEA
    Q9Y3Q0NAALAD2NAALADase IIT70036SwissTargetPrediction
    Q9NZ08ERAP1Endoplasmic reticulum aminopeptidase 1T72849SEA

    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
    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
    T92777DI0009Acute diabete complication[ICD-11: 5A2Y]O43451MGAM
    T92777DI0201Inborn carbohydrate metabolism error[ICD-11: 5C51]O43451MGAM
    T31992DI0046Bacterial infection[ICD-11: 1A00-1C4Z]Q9ULX7CA14
    T31992DI0204Inborn metabolism deficiency[ICD-11: 5C50-5C59]Q9ULX7CA14
    T97071DI0122Diagnostic imaging[ICD-11: N.A.]Q04609FOLH1
    T97071DI0346Prostate cancer[ICD-11: 2C82]Q04609FOLH1
    T29130DI0351Psoriasis[ICD-11: EA90]P40763STAT3
    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
    T40491DI0268Molluscum contagiosum[ICD-11: 1E76]P67775PPP2CA
    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

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