3-Dehydronobilin (CHEM030351)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:50:20 UTC
Update Date2016-11-09 01:19:03 UTC
Accession NumberCHEM030351
Identification
Common Name3-Dehydronobilin
ClassSmall Molecule
Description3-Dehydronobilin is found in herbs and spices. 3-Dehydronobilin is isolated from Anthemis nobilis (Roman chamomile).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6,10-Dimethyl-3-methylidene-2,9-dioxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoic acidHMDB
Chemical FormulaC20H24O5
Average Molecular Mass344.402 g/mol
Monoisotopic Mass344.162 g/mol
CAS Registry Number63529-14-6
IUPAC Name6,10-dimethyl-3-methylidene-2,9-dioxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate
Traditional Name6,10-dimethyl-3-methylidene-2,9-dioxo-3aH,4H,5H,8H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate
SMILESC\C=C(\C)C(=O)OC1C\C(C)=C\CC(=O)\C(C)=C\C2OC(=O)C(=C)C12
InChI IdentifierInChI=1S/C20H24O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6-7,10,16-18H,5,8-9H2,1-4H3/b11-7+,12-6-,13-10+
InChI KeyFKDIIXZIKCNXAT-QLDBJWRKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative Parents
Substituents
  • Germacranolide
  • Germacrane sesquiterpenoid
  • Sesquiterpenoid
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Fatty acyl
  • Alpha,beta-unsaturated carboxylic ester
  • Tetrahydrofuran
  • Enoate ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP3.19ALOGPS
logP4.02ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)-5.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.04 m³·mol⁻¹ChemAxon
Polarizability35.76 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-9032000000-275d5fb73e9f5ca7a0f0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3059000000-ddaab2f0dd2ef979b913Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0032-9152000000-2501bf40adf2334fad3aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsi-9210000000-16b49fceac282eb89e4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1049000000-3c3fa14a3682f1071475Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-6096000000-a1b30547b95e9219cb08Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001a-9430000000-9abec1ed0dd653fa3720Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-7bd2870eed539375aefaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-1190000000-bc266add0e756f89201aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00os-3190000000-7392f9be87fed855c018Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-9065000000-b15016ab15342df11cafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-9040000000-dc0ad5f590e8391f04fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-9050000000-ec0e5a17ba1a1ad5ff39Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0036691
FooDB IDFDB015623
Phenol Explorer IDNot Available
KNApSAcK IDC00011800
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35014203
ChEBI ID174642
PubChem Compound ID131752038
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
2. 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.
3. 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.
4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
5. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
6. The lipid handbook with CD-ROM