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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:07 UTC
Update Date2022-03-07 02:53:29 UTC
HMDB IDHMDB0032834
Secondary Accession Numbers
  • HMDB32834
Metabolite Identification
Common Name7-Acetoxy-6-hydroxylimonin
Description7-Acetoxy-6-hydroxylimonin belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. 7-Acetoxy-6-hydroxylimonin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862314
Synonyms
ValueSource
19-(Furan-3-yl)-11-hydroxy-9,9,13,20-tetramethyl-5,17-dioxo-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosan-12-yl acetic acidGenerator
Chemical FormulaC28H34O10
Average Molecular Weight530.5636
Monoisotopic Molecular Weight530.215197308
IUPAC Name19-(furan-3-yl)-11-hydroxy-9,9,13,20-tetramethyl-5,17-dioxo-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosan-12-yl acetate
Traditional Name19-(furan-3-yl)-11-hydroxy-9,9,13,20-tetramethyl-5,17-dioxo-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosan-12-yl acetate
CAS Registry Number208333-73-7
SMILES
CC(=O)OC1C(O)C2C(C)(C)OC3CC(=O)OCC23C2CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C1
InChI Identifier
InChI=1S/C28H34O10/c1-13(29)35-21-18(31)19-24(2,3)37-16-10-17(30)34-12-27(16,19)15-6-8-25(4)20(14-7-9-33-11-14)36-23(32)22-28(25,38-22)26(15,21)5/h7,9,11,15-16,18-22,31H,6,8,10,12H2,1-5H3
InChI KeyLFAMVZIOUNWBKU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentSteroid lactones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point278 - 280 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP3.09ALOGPS
logP1.3ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)13.79ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area134.03 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity125.96 m³·mol⁻¹ChemAxon
Polarizability52.72 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+214.97631661259
DarkChem[M-H]-211.37731661259
DeepCCS[M-2H]-242.77230932474
DeepCCS[M+Na]+218.38830932474
AllCCS[M+H]+218.432859911
AllCCS[M+H-H2O]+216.932859911
AllCCS[M+NH4]+219.932859911
AllCCS[M+Na]+220.332859911
AllCCS[M-H]-222.032859911
AllCCS[M+Na-2H]-223.632859911
AllCCS[M+HCOO]-225.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7-Acetoxy-6-hydroxylimoninCC(=O)OC1C(O)C2C(C)(C)OC3CC(=O)OCC23C2CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C14461.9Standard polar33892256
7-Acetoxy-6-hydroxylimoninCC(=O)OC1C(O)C2C(C)(C)OC3CC(=O)OCC23C2CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C13234.6Standard non polar33892256
7-Acetoxy-6-hydroxylimoninCC(=O)OC1C(O)C2C(C)(C)OC3CC(=O)OCC23C2CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C14238.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
7-Acetoxy-6-hydroxylimonin,1TMS,isomer #1CC(=O)OC1C(O[Si](C)(C)C)C2C(C)(C)OC3CC(=O)OCC32C2CCC3(C)C(C4=COC=C4)OC(=O)C4OC43C12C3806.0Semi standard non polar33892256
7-Acetoxy-6-hydroxylimonin,1TBDMS,isomer #1CC(=O)OC1C(O[Si](C)(C)C(C)(C)C)C2C(C)(C)OC3CC(=O)OCC32C2CCC3(C)C(C4=COC=C4)OC(=O)C4OC43C12C4051.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7-Acetoxy-6-hydroxylimonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-059f-6034910000-9c48e17daab6e45d64062017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Acetoxy-6-hydroxylimonin GC-MS (1 TMS) - 70eV, Positivesplash10-000l-6012390000-e64f53322d787bc19b2a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Acetoxy-6-hydroxylimonin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-13Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7-Acetoxy-6-hydroxylimonin GC-MS ("7-Acetoxy-6-hydroxylimonin,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 10V, Positive-QTOFsplash10-01x0-0000980000-da19c57a977f4dde49c72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 20V, Positive-QTOFsplash10-0230-0001930000-f70ab07707f2228173632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 40V, Positive-QTOFsplash10-0znm-9311710000-b3f0dc5c37e0946e0b7d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 10V, Negative-QTOFsplash10-002r-2000930000-ac4868b15d50eeb01c912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 20V, Negative-QTOFsplash10-052u-3000930000-805bcc8ab9ce036eb3ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 40V, Negative-QTOFsplash10-0a4l-9000600000-671b8cc1660c2acc82f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 10V, Negative-QTOFsplash10-004i-0000390000-bf11d723c2b2a9b752c92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 20V, Negative-QTOFsplash10-0a6r-9000460000-7cdaae4a4948080c98fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 40V, Negative-QTOFsplash10-0a6r-9300860000-0414b9b86cb64faafb632021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 10V, Positive-QTOFsplash10-001i-0000190000-759ea4679f1890ff540c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 20V, Positive-QTOFsplash10-008i-0000940000-097fb980b23b0abce4c72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7-Acetoxy-6-hydroxylimonin 40V, Positive-QTOFsplash10-0006-7392220000-5c6655a344f0badf7f782021-09-22Wishart 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 IDFDB010811
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751327
PDB IDNot Available
ChEBI IDNot Available
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  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. [PubMed:16902246 ]
  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. [PubMed:17374880 ]
  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. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.