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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:35:39 UTC
Update Date2020-09-27 18:43:03 UTC
HMDB IDHMDB0036452
Secondary Accession Numbers
  • HMDB36452
Metabolite Identification
Common Namealpha-Cadinol
Descriptionalpha-cadinol, also known as cadin-4-en-10-ol or α-cadinol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-cadinol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1601232183
Synonyms
ValueSource
(-)-alpha-CadinolChEBI
(1R,4S,4AR,8ar)-4-isopropyl-1,6-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-olChEBI
Cadin-4-en-10-olChEBI
(-)-a-CadinolGenerator
(-)-Α-cadinolGenerator
a-CadinolGenerator
Α-cadinolGenerator
CadinolMeSH
l-alpha-CadinolPhytoBank
l-α-CadinolPhytoBank
alpha-CadinolPhytoBank
Chemical FormulaC15H26O
Average Molecular Weight222.372
Monoisotopic Molecular Weight222.198365457
IUPAC Name(1R,4S,4aR,8aR)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol
Traditional Nameα-cadinol
CAS Registry Number481-34-5
SMILES
[H][C@@]12C=C(C)CC[C@@]1([H])[C@](C)(O)CC[C@H]2C(C)C
InChI Identifier
InChI=1S/C15H26O/c1-10(2)12-7-8-15(4,16)14-6-5-11(3)9-13(12)14/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13-,14+,15+/m0/s1
InChI KeyLHYHMMRYTDARSZ-BYNSBNAKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Cadinane sesquiterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point74.5 - 75 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.056 g/LALOGPS
logP3.52ALOGPS
logP3.54ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-0.59ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.43 m³·mol⁻¹ChemAxon
Polarizability27.81 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00020065
Chemspider ID8574094
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlpha-Cadinol
METLIN IDNot Available
PubChem Compound10398656
PDB IDNot Available
ChEBI ID132905
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Chang HT, Cheng YH, Wu CL, Chang ST, Chang TT, Su YC: Antifungal activity of essential oil and its constituents from Calocedrus macrolepis var. formosana Florin leaf against plant pathogenic fungi. Bioresour Technol. 2008 Sep;99(14):6266-70. doi: 10.1016/j.biortech.2007.12.005. Epub 2008 Feb 21. [PubMed:18206367 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.