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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:05:59 UTC
Update Date2022-03-07 02:54:45 UTC
HMDB IDHMDB0036033
Secondary Accession Numbers
  • HMDB36033
Metabolite Identification
Common Name7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene
Description7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 7alpha-1(10->19)-abeo-7-acetoxyobacun-9(11)-ene has been detected, but not quantified in, citrus. This could make 7alpha-1(10->19)-abeo-7-acetoxyobacun-9(11)-ene a potential biomarker for the consumption of these foods.
Structure
Data?1563862811
Synonyms
ValueSource
7a-1(10->19)-abeo-7-acetoxyobacun-9(11)-eneGenerator
7Α-1(10->19)-abeo-7-acetoxyobacun-9(11)-eneGenerator
(4Z)-18-(Furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetic acidGenerator
Chemical FormulaC28H32O8
Average Molecular Weight496.5489
Monoisotopic Molecular Weight496.209718
IUPAC Name(4Z)-18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate
Traditional Name(4Z)-18-(furan-3-yl)-8,8,12,19-tetramethyl-6,16-dioxo-7,14,17-trioxapentacyclo[10.9.0.0²,⁹.0¹³,¹⁵.0¹³,¹⁹]henicosa-1(21),4-dien-11-yl acetate
CAS Registry Number85643-97-6
SMILES
CC(=O)OC1CC2C(C\C=C/C(=O)OC2(C)C)C2=CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C1
InChI Identifier
InChI=1S/C28H32O8/c1-15(29)33-20-13-19-17(7-6-8-21(30)35-25(19,2)3)18-9-11-26(4)22(16-10-12-32-14-16)34-24(31)23-28(26,36-23)27(18,20)5/h6,8-10,12,14,17,19-20,22-23H,7,11,13H2,1-5H3/b8-6-
InChI KeyVIZDPIMTQWFZEF-VURMDHGXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNot Available
Direct ParentNaphthopyrans
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
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 Solubility0.016 g/LALOGPS
logP4.16ALOGPS
logP3.5ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area104.57 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity127.14 m³·mol⁻¹ChemAxon
Polarizability51.04 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+214.04731661259
DarkChem[M-H]-203.17431661259
DeepCCS[M-2H]-240.74630932474
DeepCCS[M+Na]+216.17130932474
AllCCS[M+H]+216.232859911
AllCCS[M+H-H2O]+214.332859911
AllCCS[M+NH4]+218.032859911
AllCCS[M+Na]+218.532859911
AllCCS[M-H]-220.432859911
AllCCS[M+Na-2H]-221.832859911
AllCCS[M+HCOO]-223.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-eneCC(=O)OC1CC2C(C\C=C/C(=O)OC2(C)C)C2=CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C14837.7Standard polar33892256
7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-eneCC(=O)OC1CC2C(C\C=C/C(=O)OC2(C)C)C2=CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C13284.3Standard non polar33892256
7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-eneCC(=O)OC1CC2C(C\C=C/C(=O)OC2(C)C)C2=CCC3(C)C(OC(=O)C4OC34C12C)C1=COC=C13921.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w3c-3022900000-80825eae52c841b8d31d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 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 - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 10V, Positive-QTOFsplash10-002k-0000900000-2d06e5728c5b1ef095152016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 20V, Positive-QTOFsplash10-0570-0021900000-7eb66ccc2cf673de4d832016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 40V, Positive-QTOFsplash10-001d-9127200000-cbce69d9b40773bef7342016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 10V, Negative-QTOFsplash10-0udj-0000900000-9b6b574592048176d0cf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 20V, Negative-QTOFsplash10-0zfr-2000900000-7d269d7578e413a6c8ce2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 40V, Negative-QTOFsplash10-0a4i-9002600000-13686c7e43b4a858f2822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 10V, Positive-QTOFsplash10-0002-0000900000-1a381b4ae37add237a322021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 20V, Positive-QTOFsplash10-0udr-0210900000-c62a46c38b53d8f9d3042021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 40V, Positive-QTOFsplash10-0a6r-0790400000-6ba854eba09e92fbde362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 10V, Negative-QTOFsplash10-0002-0000900000-b13e75a9e37a1aad48b92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 20V, Negative-QTOFsplash10-0a4i-9000000000-323328ab38901ec47a982021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 7alpha-1(10->19)-Abeo-7-acetoxyobacun-9(11)-ene 40V, Negative-QTOFsplash10-0a4l-8000900000-e92a79e43bdfc495bad72021-09-24Wishart 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 IDFDB014852
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751902
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .