Deacetylnomilin (CHEM029577)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 01:15:26 UTC
Update Date2016-11-09 01:18:54 UTC
Accession NumberCHEM029577
Identification
Common NameDeacetylnomilin
ClassSmall Molecule
DescriptionIsolated from orange (Citrus sinensis) and finger lime (Microcitrus australasica). Deacetylnomilin is found in lemon, sweet orange, and citrus.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
IsolimoninHMDB
Chemical FormulaC26H32O8
Average Molecular Mass472.528 g/mol
Monoisotopic Mass472.210 g/mol
CAS Registry Number3264-90-2
IUPAC Name7-(furan-3-yl)-13-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione
Traditional Name7-(furan-3-yl)-13-hydroxy-1,8,12,17,17-pentamethyl-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosane-5,15,20-trione
SMILESCC12CCC3C4(C)C(CC(=O)C3(C)C11OC1C(=O)OC2C1=COC=C1)C(C)(C)OC(=O)CC4O
InChI IdentifierInChI=1S/C26H32O8/c1-22(2)15-10-17(28)25(5)14(24(15,4)16(27)11-18(29)33-22)6-8-23(3)19(13-7-9-31-12-13)32-21(30)20-26(23,25)34-20/h7,9,12,14-16,19-20,27H,6,8,10-11H2,1-5H3
InChI KeyHWAJASVMTDEFJN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid skeleton
  • Naphthopyran
  • Naphthalene
  • Caprolactone
  • 1,4-dioxepane
  • Delta valerolactone
  • Dioxepane
  • Delta_valerolactone
  • Oxepane
  • Oxane
  • Pyran
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Furan
  • Secondary alcohol
  • Carboxylic acid ester
  • Lactone
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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 Solubility0.084 g/LALOGPS
logP2.7ALOGPS
logP2.58ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)14.42ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area115.57 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity116.45 m³·mol⁻¹ChemAxon
Polarizability48.38 ųChemAxon
Number of Rings6ChemAxon
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, Positivesplash10-01si-2259800000-a4d140cdff7bea3a3998Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-003r-7064490000-0939502d59b9f57a162dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0001900000-ac2fd55de38221c65f6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4u-0025900000-3428d6398664c9707925Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-9416000000-5b63ee7c0bd320d2261eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00b9-0001900000-7c933e17bd71d8b72217Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0umj-1006900000-28026242e599d86106f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4m-9107200000-389a14bbe7886e74cb64Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000900000-6e029cb28edf4d9b8aa3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0141900000-968227572d16a11da18fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2921200000-cd914e3f6b6a42b6f420Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-6092626f870c8a12f250Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0000900000-c9163d595834a7b09573Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-4013900000-8418108a5da482d487ccSpectrum
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 IDHMDB0035684
FooDB IDFDB014401
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID13857953
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