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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:49 UTC
Update Date2022-03-07 02:49:15 UTC
HMDB IDHMDB0002352
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 ).
Structure
Data?1582752245
Synonyms
ValueSource
(1R,3R,4S,4AR,6R)-6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diolChEBI
(1R,3R,4S,4AR,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene-1,3-diolHMDB
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
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
Substituents
  • Eremophilane sesquiterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.85 g/LALOGPS
logP2.7ALOGPS
logP1.91ChemAxon
logS-2.4ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.16331661259
DarkChem[M-H]-154.33231661259
DeepCCS[M-2H]-196.57730932474
DeepCCS[M+Na]+171.51830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CapsidiolC[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C2801.0Standard polar33892256
CapsidiolC[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C1847.8Standard non polar33892256
CapsidiolC[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C1909.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Capsidiol,1TMS,isomer #1C=C(C)[C@@H]1CC=C2[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@H](C)[C@@]2(C)C11925.7Semi standard non polar33892256
Capsidiol,1TMS,isomer #2C=C(C)[C@@H]1CC=C2[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@H](C)[C@@]2(C)C11936.6Semi standard non polar33892256
Capsidiol,2TMS,isomer #1C=C(C)[C@@H]1CC=C2[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H](C)[C@@]2(C)C11937.1Semi standard non polar33892256
Capsidiol,1TBDMS,isomer #1C=C(C)[C@@H]1CC=C2[C@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@]2(C)C12207.6Semi standard non polar33892256
Capsidiol,1TBDMS,isomer #2C=C(C)[C@@H]1CC=C2[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](C)[C@@]2(C)C12206.2Semi standard non polar33892256
Capsidiol,2TBDMS,isomer #1C=C(C)[C@@H]1CC=C2[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@]2(C)C12413.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Capsidiol GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-2930000000-c6a7a1a3b2cd45b787292017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capsidiol GC-MS (2 TMS) - 70eV, Positivesplash10-016u-6197000000-8f3e3a1289174fe1cd872017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capsidiol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 10V, Positive-QTOFsplash10-014r-0190000000-4f408854a045f002ce8c2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 20V, Positive-QTOFsplash10-0gbi-2690000000-f2e94dce44ae9b9ac2df2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 40V, Positive-QTOFsplash10-0uxr-9710000000-4e4ebb2003b289f81d112017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 10V, Negative-QTOFsplash10-000i-0090000000-e1fa0089980b18e8a4222017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 20V, Negative-QTOFsplash10-00kr-0190000000-5cc78cd709d6e3a588152017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 40V, Negative-QTOFsplash10-0i09-2960000000-4d5021b41dbcabf76b872017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 10V, Negative-QTOFsplash10-000i-0090000000-c0031dc201eac6b6350a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 20V, Negative-QTOFsplash10-000i-0190000000-c5d1ce0d6817df353cab2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 40V, Negative-QTOFsplash10-001i-0940000000-b0c4585c354b5421c7d12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 10V, Positive-QTOFsplash10-002r-0970000000-ddcf71bbc9544a6146752021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 20V, Positive-QTOFsplash10-00n0-3940000000-fdbebf5ba44e69f055052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsidiol 40V, Positive-QTOFsplash10-015c-9310000000-1b969f3a620273af3ea82021-09-24Wishart LabView Spectrum
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 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 IDNot Available
Good Scents IDNot Available
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 ]