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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2019-01-11 19:35:05 UTC
HMDB IDHMDB0015138
Secondary Accession Numbers
  • HMDB15138
Metabolite Identification
Common NameCromoglicic acid
DescriptionCromoglicic 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 degranulation 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
Data?1547235305
Synonyms
ValueSource
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 FormulaC23H16O11
Average Molecular Weight468.3665
Monoisotopic Molecular Weight468.069261354
IUPAC Name5-{3-[(2-carboxy-4-oxo-4H-chromen-5-yl)oxy]-2-hydroxypropoxy}-4-oxo-4H-chromene-2-carboxylic acid
Traditional Namecromoglicic acid
CAS Registry Number16110-51-3
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 KeyIMZMKUWMOSJXDT-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as chromones. These are compounds containing a benzopyran-4-one moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub Class1-benzopyrans
Direct ParentChromones
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point241 - 242 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.036 g/LNot Available
LogP1.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.036 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity114.11 m³·mol⁻¹ChemAxon
Polarizability44.38 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pba-0596500000-93b57c77aba43e672f0fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00xr-4030029000-8cee526b514f9030027dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0000900000-b29947fd1c55b6bb244eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-06r2-0090000000-14c9cd86f6f2c6066ed8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4j-0090000000-28843e4d8ab22e289734JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0390000000-3f291eddb35619c6f657JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-1970000000-3eb328adfc6464d47d0aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0010900000-333b6bbaebdefd98cb8aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0040900000-549295824b43e7326954JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-0829000000-75589226ac0f3652f3f4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-066r-0040900000-5470e8167deb6420a80dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390200000-ee133f6c3b06c2f3d6dcJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01p9-0920000000-cd6dad6d34c8953cb0f1JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01003 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01003 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01003
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2779
KEGG Compound IDC06928
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCromoglicic acid
METLIN IDNot Available
PubChem Compound2882
PDB IDNot Available
ChEBI ID59773
References
Synthesis ReferenceNot 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 ]