Structure Database (LMSD)

Common Name
Sclareol
Systematic Name
(1R,2R,4aS,8aS)-1-[(3R)-3-hydroxy-3-methylpent-4-en-1-yl]-2,5,5,8a-tetramethyldecahydronaphthalen-2-ol labd-14-ene-8,13-diol
Synonyms
  • (13R)-Labd-14-ene-8alpha,13beta-diol
LM ID
LMPR0104030010
Formula
Exact Mass
Calculate m/z
308.27153
Status
Curated


Classification

Biological Context

Sclareol is a diterpene originally isolated from S. sclarea and has diverse biological activities.1,2,3 It is active against A. naeslundii, P. gingivalis, and P. anaerobius bacteria (MICs = 12.5, 6.2, and 3.1 μg/ml, respectively).1 Sclareol (5 and 10 μg/ml) inhibits LPS-induces increases in nitric oxide (NO) production and COX-2 and inducible nitric oxide synthase (iNOS) protein levels in RAW 264.7 macrophages.2 It reduces λ-carrageenan-induced hind paw edema in mice when administered at a dose of 10 mg/kg. It inhibits the growth of HCT116 cells (GI50 = 34 μM), as well as induces apoptosis and halts the cell cycle at the G1 phase in HCT116 cells when used at a concentration of 100 μM.3 Liposome-encapsulated sclareol (275 mg/kg, i.p.) reduces tumor growth in an HCT116 mouse xenograft model.

This information has been provided by Cayman Chemical

References

2. Huang, G.-J., Pan, C.-H., and Wu, C.-H. Sclareol exhibits anti-inflammatory activity in both lipopolysaccharide-stimulated macrophages and the λ-carrageenan-induced paw edema model. J. Nat. Prod. 75(1), 54-59 (2012).
3. Dimas, K., Hatziantgoniou, S., Tseleni, S., et al. Sclareol induces apoptosis in human HCT116 colon cancer cells in vitro and suppression of HCT116 tumor growth in immunodeficient mice. Apoptosis 12(4), 685-694 (2007).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Salvia sclarea (#38869)
Magnoliopsida (#3398)
Höhere Terpenverbindungen L. Zur Kenntnis des Sclareols,
Helv Chim Acta, 1931

String Representations

InChiKey (Click to copy)
XVULBTBTFGYVRC-HHUCQEJWSA-N
InChi (Click to copy)
InChI=1S/C20H36O2/c1-7-18(4,21)13-9-16-19(5)12-8-11-17(2,3)15(19)10-14-20(16,6)22/h7,15-16,21-22H,1,8-14H2,2-6H3/t15-,16+,18-,19-,20+/m0/s1
SMILES (Click to copy)
C1C(C)(C)[C@]2([H])CC[C@@](C)(O)[C@H](CC[C@](O)(C)C=C)[C@@]2(C)CC1

Other Databases

Wikipedia
KEGG ID
CHEBI ID
PubChem CID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 22
Rings 2
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 344.78
Topological Polar Surface Area 40.46
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 2
logP 5.27
Molar Refractivity 93.66

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Created at
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Updated at
21st Feb 2024