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Record Information
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2020-02-26 21:24:05 UTC
Secondary Accession Numbers
  • HMDB02352
Metabolite Identification
Common NameCapsidiol
DescriptionCapsidiol is a phytoalexin, a natural fungicide present in pepper. (PMID: 10335386 ). Capsidiol shows bacteriostatic properties in vitro against Helicobacter pylori with a minimum inhibitory concentration (MIC) of 200 microg/mL. (PMID: 17002415 ). Capsidiol is a bicyclic, dihydroxylated sesquiterpene produced by several solanaceous species in response to a variety of environmental stimuli. It is the primary antimicrobial compound produced by Nicotiana tabacum in response to fungal elicitation, and it is formed via the isoprenoid pathway from 5-epi-aristolochene. (PMID: 11556809 ).
Chemical FormulaC15H24O2
Average Molecular Weight236.355
Monoisotopic Molecular Weight236.177630013
IUPAC Name(1R,3R,4S,4aR,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol
Traditional Namecapsidiol
CAS Registry Number37208-05-2
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
  • Eremophilane sesquiterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors

Route of exposure:

Biological location:



Naturally occurring process:


Industrial application:

Biological role:

Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.85 g/LALOGPS
pKa (Strongest Acidic)14.35ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.52 m³·mol⁻¹ChemAxon
Polarizability27.64 ųChemAxon
Number of Rings2ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-2930000000-c6a7a1a3b2cd45b78729Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-016u-6197000000-8f3e3a1289174fe1cd87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0190000000-4f408854a045f002ce8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gbi-2690000000-f2e94dce44ae9b9ac2dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-9710000000-4e4ebb2003b289f81d11Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-e1fa0089980b18e8a422Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0190000000-5cc78cd709d6e3a58815Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0i09-2960000000-4d5021b41dbcabf76b87Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
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 IDFDB014812
KNApSAcK IDC00003108
Chemspider ID142224
KEGG Compound IDC09627
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCapsidiol
METLIN IDNot Available
PubChem Compound161937
PDB IDNot Available
ChEBI ID28283
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Lozoya-Gloria E: Biochemical and molecular tools for the production of useful terpene products from pepper (Capsicum annuum). Adv Exp Med Biol. 1999;464:63-76. [PubMed:10335386 ]
  2. De Marino S, Borbone N, Gala F, Zollo F, Fico G, Pagiotti R, Iorizzi M: New constituents of sweet Capsicum annuum L. fruits and evaluation of their biological activity. J Agric Food Chem. 2006 Oct 4;54(20):7508-16. [PubMed:17002415 ]
  3. Ralston L, Kwon ST, Schoenbeck M, Ralston J, Schenk DJ, Coates RM, Chappell J: Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum). Arch Biochem Biophys. 2001 Sep 15;393(2):222-35. [PubMed:11556809 ]