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

1. Ma, D., He, J., and He, D. Chamazulene reverses osteoarthritic inflammation through regulation of matrix metalloproteinases (MMPs) and NF-kβ pathway in in-vitro and in-vivo models. Biosci. Biotechol. Biochem. 84(2), 402-410 (2020).

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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