Structure Database (LMSD)

Common Name
cedrol
Systematic Name
(8R)-cedran-8-ol
Synonyms
  • (+)-cedrol
  • 8betaH-cedran-8-ol
  • Cedrol
  • [3R-(3alpha,3abeta,6alpha,7beta,8aalpha)]-octahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazulen-6-ol
  • alpha-cedrol
LM ID
LMPR0103690007
Formula
Exact Mass
Calculate m/z
222.198365
Status
Curated



Classification

Biological Context

(+)-Cedrol is a sesquiterpene alcohol that has been used in Cannabis testing and has diverse biological activities.1 It inhibits the growth of L. sulphureus, G. trabeum, L. betulina, and T. versicolor wood decay fungi when used at a concentration of 100 μg/ml.2 (+)-Cedrol inhibits the cytochrome P450 (CYP) isoforms CYP2B6 and CYP3A4 (Kis = 0.9 and 3.4 μM, respectively).3 In vivo, (+)-cedrol (200 mg/kg) prevents hair follicle dystrophy and reduces hair loss in a mouse model of alopecia induced by cyclophosphamide .4 (+)-Cedrol-loaded nanostructured lipid particles reduce peritoneal mast cell degranulation, a component of the type I anaphylactic response, induced by compound 48/80 in mice.5

This information has been provided by Cayman Chemical

References

1. Fischedick, J.T. Identification of terpenoid chemotypes among high (–)-trans-Δ9-tetrahydrocannabinol-producing Cannabis sativa L. cultivars. Cannabis Cannabinoid Res. 2(1), 34-47 (2017).
4. Jeong, H.U., Kwon, S.S., Kong, T.Y., et al. Inhibitory effects of cedrol, β-cedrene, and thujopsene on cytochrome P450 enzyme activities in human liver microsomes. J. Toxicol. Environ. Health A 77(22-24), 1522-1532 (2014).

String Representations

InChiKey (Click to copy)
SVURIXNDRWRAFU-OGMFBOKVSA-N
InChi (Click to copy)
InChI=1S/C15H26O/c1-10-5-6-11-13(2,3)12-9-15(10,11)8-7-14(12,4)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14-,15+/m1/s1
SMILES (Click to copy)
[C@H]1(C)[C@@]23[C@]([H])(C(C)(C)[C@@H](C2)[C@](C)(O)CC3)CC1

Other Databases

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 16
Rings 3
Aromatic Rings 0
Rotatable Bonds 0
Van der Waals Molecular Volume 239.77
Topological Polar Surface Area 20.23
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 1
logP 3.90
Molar Refractivity 66.58

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Created at
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Updated at
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