cromoglicic acid   Click here for help

GtoPdb Ligand ID: 7608

Synonyms: cromoglycate | cromolyn | cromolyn sodium | FPL-670 | Intal® | Opticrom® | sodium cromoglicate
Approved drug Immunopharmacology Ligand
cromoglicic acid is an approved drug (FDA (1984))
Compound class: Synthetic organic
Comment: Cromoglicic acid (cromolyn) is regarded as a mast cell stabilising drug, although its exact mechanism of action appears to be much more complicated.
Recent reports suggest that cromolyn inhibits glycogen synthase kinase 3β and may therefore have potential to treat diabetes and obesity [3] and may prove effective in treating insulin-induced lipoatrophy [4]. It also has reported potential anti-fibrotic action through agonism of GPR35 [1,5].
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: cromoglicic acid

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 173.71
Molecular weight 468.07
XLogP 3.48
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC(COc1cccc2c1c(=O)cc(o2)C(=O)O)COc1cccc2c1c(=O)cc(o2)C(=O)O
Isomeric SMILES OC(COc1cccc2c1c(=O)cc(o2)C(=O)O)COc1cccc2c1c(=O)cc(o2)C(=O)O
InChI 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
References
1. Choi JS, Kim JK, Yang YJ, Kim Y, Kim P, Park SG, Cho EY, Lee DH, Choi JW. (2015)
Identification of cromolyn sodium as an anti-fibrotic agent targeting both hepatocytes and hepatic stellate cells.
Pharmacol Res, 102: 176-83. [PMID:26453959]
2. Meyerhof W, Batram C, Kuhn C, Brockhoff A, Chudoba E, Bufe B, Appendino G, Behrens M. (2010)
The molecular receptive ranges of human TAS2R bitter taste receptors.
Chem Senses, 35 (2): 157-70. [PMID:20022913]
3. Motawi TM, Bustanji Y, El-Maraghy SA, Taha MO, Al Ghussein MA. (2013)
Naproxen and cromolyn as new glycogen synthase kinase 3β inhibitors for amelioration of diabetes and obesity: an investigation by docking simulation and subsequent in vitro/in vivo biochemical evaluation.
J Biochem Mol Toxicol, 27 (9): 425-36. [PMID:23784744]
4. Phua EJ, Lopez X, Ramus J, Goldfine AB. (2013)
Cromolyn sodium for insulin-induced lipoatrophy: old drug, new use.
Diabetes Care, 36 (12): e204-5. [PMID:24265375]
5. Yang Y, Lu JY, Wu X, Summer S, Whoriskey J, Saris C, Reagan JD. (2010)
G-protein-coupled receptor 35 is a target of the asthma drugs cromolyn disodium and nedocromil sodium.
Pharmacology, 86 (1): 1-5. [PMID:20559017]