Structure Database (LMSD)

Common Name
Chamazulene
Systematic Name
Synonyms
LM ID
LMPR0103410002
Formula
Exact Mass
Calculate m/z
184.1252
Status
Curated



Classification

Biological Context

Chamazulene is a terpene that has been found in chamomile (M. recutita) flowers and has anti-inflammatory and antioxidant activities.1 It reduces increases in matrix metalloproteinase-3 (MMP-3), MMP-9, COX-2, inducible nitric oxide synthase (iNOS), and p65 NF-κB levels in IL-1β-stimulated primary rat chondrocytes when used at a concentration of 10 µg/ml. Chamazulene (10 and 20 µg/ml) reduces IL-1β-induced production of malondialdehyde (MDA) and increases levels of superoxide dismutase (SOD), catalase, and glutathione peroxidase (GPX) in primary rat chondrocytes. In vivo, chamazulene (25 and 50 mg/kg) reduces hind paw volume, serum levels of MDA, TNF-α, and IL-6, and cartilage erosion in a rat model of osteoarthritis induced by complete Freund’s adjuvant (CFA).

This information has been provided by Cayman Chemical

References

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Matricaria chamomilla (#98504)
Magnoliopsida (#3398)
Chamazulene: an antioxidant-type inhibitor of leukotriene B4 formation.,
Planta Med, 1994
Pubmed ID: 7997466

String Representations

InChiKey (Click to copy)
GXGJIOMUZAGVEH-UHFFFAOYSA-N
InChi (Click to copy)
InChI=1S/C14H16/c1-4-12-7-5-10(2)13-8-6-11(3)14(13)9-12/h5-9H,4H2,1-3H3
SMILES (Click to copy)
C12=C(C)C=CC1=C(C)C=CC(CC)=C2

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 14
Rings 2
Aromatic Rings 2
Rotatable Bonds 1
Van der Waals Molecular Volume 191.04
Topological Polar Surface Area 0.00
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 0
logP 4.02
Molar Refractivity 62.80

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Updated at
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