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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:24:01 UTC
Update Date2019-07-23 06:28:23 UTC
HMDB IDHMDB0039048
Secondary Accession Numbers
  • HMDB39048
Metabolite Identification
Common Name(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate)
Description(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) has been detected, but not quantified in, a few different foods, such as coffee and coffee products, green vegetables, and herbs and spices. This could make (5a,6a,8a,11a)-8-hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetate) a potential biomarker for the consumption of these foods.
Structure
Data?1563863303
Synonyms
ValueSource
(5a,6a,8a,11a)-8-Hydroxy-2-oxo-1(10),3-guaiadien-12,6-olide-15-al 8-(4-hydroxyphenylacetic acid)Generator
9-Formyl-3,6-dimethyl-2,7-dioxo-2H,3H,3ah,4H,5H,7H,9ah,9BH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetic acidGenerator
Chemical FormulaC23H22O7
Average Molecular Weight410.4166
Monoisotopic Molecular Weight410.136553058
IUPAC Name9-formyl-3,6-dimethyl-2,7-dioxo-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate
Traditional Name9-formyl-3,6-dimethyl-2,7-dioxo-3H,3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-4-yl 2-(4-hydroxyphenyl)acetate
CAS Registry Number374536-44-4
SMILES
CC1C2C(OC1=O)C1C(C=O)=CC(=O)C1=C(C)CC2OC(=O)CC1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C23H22O7/c1-11-7-17(29-18(27)8-13-3-5-15(25)6-4-13)20-12(2)23(28)30-22(20)21-14(10-24)9-16(26)19(11)21/h3-6,9-10,12,17,20-22,25H,7-8H2,1-2H3
InChI KeyCICWEHOIACOOIN-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Substituents
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aldehyde
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.032 g/LALOGPS
logP2.38ALOGPS
logP2.13ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)9.47ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.97 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity106.93 m³·mol⁻¹ChemAxon
Polarizability41.31 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1911000000-f44713eeb340bbd449d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2910100000-5a6df1bda200920832a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03du-0769800000-adb07d2b251d93067dffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0952000000-c1720c337cef5b9db29fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-2920000000-d9d262fbf09b9c54febbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0354900000-a455a0055ad1cf86e657Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a7i-0594200000-0db247652e733d312270Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-1970000000-263b0d2f35564dffd2a1Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDFDB018545
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752526
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH 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.. .