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Cromoglicic acid

July 24, 2017
Common Name

Cromoglicic acid Description

Cromoglicic acid is only found in individuals that have used or taken this drug. It is a chromone complex that acts by inhibiting the release of chemical mediators from sensitized mast cells. It is used in the prophylactic treatment of both allergic and exercise-induced asthma, but does not affect an established asthmatic attack. [PubChem]Cromoglicate inhibits degranliation of mast cells, subsequently preventing the release of histamine and slow-reacting substance of anaphylaxis (SRS-A), mediators of type I allergic reactions. Cromoglicate also may reduce the release of inflammatory leukotrienes. Cromoglicate may act by inhibiting calcium influx. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 5-[3-(2-Carboxy-4-oxo-4H-5-chromenyloxy)-2-hydroxypropoxy]-4-oxo-4H-2-chromenecarboxylic acidChEBI Acide cromogliciqueChEBI acido CromoglicicoChEBI Acidum cromoglicicumChEBI CromolynChEBI 5-[3-(2-Carboxy-4-oxo-4H-5-chromenyloxy)-2-hydroxypropoxy]-4-oxo-4H-2-chromenecarboxylateGenerator CromoglicateGenerator CromoglycateHMDB AaraneMeSH Bicromat sprayMeSH Cromoglycate, sodiumMeSH Disodium cromoglycateMeSH IntalMeSH OpticromMeSH VicromMeSH Cromolyn sodiumMeSH FPL 670MeSH LomudalMeSH NalcromMeSH Sodium cromoglycateMeSH Cromoglycate, disodiumMeSH Cromoglycic acidMeSH FPL-670MeSH Acid, cromoglicicMeSH Acid, cromoglycicMeSH NasalcromMeSH

Chemical Formlia

C23H16O11 Average Molecliar Weight

468.3665 Monoisotopic Molecliar Weight

468.069261354 IUPAC Name

5-{3-[(2-carboxy-4-oxo-4H-chromen-5-yl)oxy]-2-hydroxypropoxy}-4-oxo-4H-chromene-2-carboxylic acid Traditional Name

cromoglicic acid CAS Registry Number

16110-51-3 SMILES

OC(COC1=CC=CC2=C1C(=O)C=C(O2)C(O)=O)COC1=CC=CC2=C1C(=O)C=C(O2)C(O)=O

InChI Identifier

InChI=1S/C23H16O11/c24-11(9-31-14-3-1-5-16-20(14)12(25)7-18(33-16)22(27)28)10-32-15-4-2-6-17-21(15)13(26)8-19(34-17)23(29)30/h1-8,11,24H,9-10H2,(H,27,28)(H,29,30)

InChI Key

IMZMKUWMOSJXDT-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as chromones. These are compounds containing a benzopyran-4-one moiety. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Benzopyrans Direct Parent

Chromones Alternative Parents

  • Pyranones and derivatives
  • Alkyl aryl ethers
  • Dicarboxylic acids and derivatives
  • Benzenoids
  • Vinylogous esters
  • Heteroaromatic compounds
  • Secondary alcohols
  • Oxacyclic compounds
  • Carboxylic acids
  • Organic oxides
  • Hydrocarbon derivatives

    • Substituents

  • Chromone
  • Alkyl aryl ether
  • Pyranone
  • Dicarboxylic acid or derivatives
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous ester
  • Secondary alcohol
  • Oxacycle
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • dicarboxylic acid (CHEBI:59773 )
  • chromones (CHEBI:59773 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Anti-Asthmatic Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point241 – 242 °CNot Available Boiling PointNot AvailableNot Available Water Solubility3.58e-02 g/LNot Available LogP1.6Not Available

    Predicted Properties

    Property Value Source Water Solubility0.036 mg/mLALOGPS logP1.84ALOGPS logP1.48ChemAxon logS-4.1ALOGPS pKa (Strongest Acidic)1.77ChemAxon pKa (Strongest Basic)-3.4ChemAxon Physiological Charge-2ChemAxon Hydrogen Acceptor Count11ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area165.89 Å2ChemAxon Rotatable Bond Count8ChemAxon Refractivity114.11 m3·mol-1ChemAxon Polarizability44.38 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-014i-0000900000-b29947fd1c55b6bb244eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-06r2-0090000000-14c9cd86f6f2c6066ed8View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4j-0090000000-28843e4d8ab22e289734View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-0390000000-3f291eddb35619c6f657View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QTOF , positivesplash10-0a4i-1970000000-3eb328adfc6464d47d0aView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01003

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01003

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01003 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2779 KEGG Compound ID

    C06928 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Cromoglicate NuGOwiki Link

    HMDB15138 Metagene Link

    HMDB15138 METLIN ID

    Not Available PubChem Compound

    2882 PDB ID

    Not Available ChEBI ID

    59773

    Product: Tolazoline

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Heinke S, Szucs G, Norris A, Droogmans G, Nilius B: Inhibition of volume-activated chloride currents in endothelial cells by chromones. Br J Pharmacol. 1995 Aug;115(8):1393-8. [PubMed:8564197 ]

    Enzymes

    General function:
    Involved in ion channel activity
    Specific function:
    Potassium channel activated by both membrane depolarization or increase in cytosolic Ca(2+) that mediates export of K(+). It is also activated by the concentration of cytosolic Mg(2+). Its activation dampens the excitatory events that elevate the cytosolic Ca(2+) concentration and/or depolarize the cell membrane. It therefore contributes to repolarization of the membrane potential. Plays a key role in controlling excitability in a number of systems, such as regulation of the contraction of smooth muscle, the tuning of hair cells in the cochlea, regulation of transmitter release, and innate immunity. In smooth muscles, its activation by high level of Ca(2+), caused by ryanodine receptors in the sarcoplasmic reticulum, regulates the membrane potential. In cochlea cells, its number and kinetic properties partly determine the characteristic frequency of each hair cell and thereby helps to establish a tonotopic map. Kinetics of KCNMA1 channels are determined by alternative splicing, phosphorylation status and its combination with modulating beta subunits. Highly sensitive to both iberiotoxin (IbTx) and charybdotoxin (CTX)
    Gene Name:
    KCNMA1
    Uniprot ID:
    Q12791
    Molecular weight:
    137558.1
    References
    1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
    2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
    General function:
    Involved in calcium ion binding
    Specific function:
    Not Available
    Gene Name:
    S100P
    Uniprot ID:
    P25815
    Molecular weight:
    10399.8
    References
    1. Arumugam T, Ramachandran V, Logsdon CD: Effect of cromolyn on S100P interactions with RAGE and pancreatic cancer growth and invasion in mouse models. J Natl Cancer Inst. 2006 Dec 20;98(24):1806-18. [PubMed:17179482 ]

    PMID: 17704298

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