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Record Information
Version3.6
Creation Date2006-05-22 14:17:49 UTC
Update Date2017-03-02 21:27:00 UTC
HMDB IDHMDB02352
Secondary Accession NumbersNone
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 ).
Structure
Thumb
Synonyms
ValueSource
(1R,3R,4S,4AR,6R)-6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diolChEBI
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
SMILES
C[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C
InChI Identifier
InChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3/t10-,11-,13-,14-,15-/m1/s1
InChI KeyBXXSHQYDJWZXPB-OKNSCYNVSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
StatusExpected but not Quantified
Origin
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Plant fungicide
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.85 mg/mLALOGPS
logP2.7ALOGPS
logP1.91ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)14.35ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.52 m3·mol-1ChemAxon
Polarizability27.64 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB014812
KNApSAcK IDC00003108
Chemspider ID142224
KEGG Compound IDC09627
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB02352
Metagene LinkHMDB02352
METLIN IDNot Available
PubChem Compound161937
PDB IDNot Available
ChEBI ID28283
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  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 ]