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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:43:55 UTC
Update Date2022-03-07 02:53:01 UTC
HMDB IDHMDB0031534
Secondary Accession Numbers
  • HMDB31534
Metabolite Identification
Common Name(+)-Galeon
Description(+)-Galeon belongs to the class of organic compounds known as meta,para-diphenylether diarylheptanoids. These are cyclic diarylheptanoids where the two benzene rings are linked to each other by an ether group conjugated to the 3-position of one benzene ring and the 4-position of the other ring (+)-Galeon is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (+)-galeon has been detected, but not quantified in, herbs and spices. This could make (+)-galeon a potential biomarker for the consumption of these foods.
Structure
Data?1563862137
Synonyms
ValueSource
GaleonMeSH
Chemical FormulaC20H22O4
Average Molecular Weight326.3863
Monoisotopic Molecular Weight326.151809192
IUPAC Name4-hydroxy-18-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one
Traditional Name4-hydroxy-18-methoxy-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one
CAS Registry Number191999-64-1
SMILES
COC1=CC2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O
InChI Identifier
InChI=1S/C20H22O4/c1-23-20-13-14-4-2-3-5-16(21)9-6-15-7-10-17(22)19(12-15)24-18(20)11-8-14/h7-8,10-13,22H,2-6,9H2,1H3
InChI KeyQUSSPXNPULRXKG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as meta,para-diphenylether diarylheptanoids. These are cyclic diarylheptanoids where the two benzene rings are linked to each other by an ether group conjugated to the 3-position of one benzene ring and the 4-position of the other ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassCyclic diarylheptanoids
Direct ParentMeta,para-diphenylether diarylheptanoids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178 - 180 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0083 g/LALOGPS
logP4.49ALOGPS
logP4.62ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)8.4ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity92.67 m³·mol⁻¹ChemAxon
Polarizability34.37 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.09131661259
DarkChem[M-H]-178.53231661259
DeepCCS[M+H]+173.29830932474
DeepCCS[M-H]-170.9430932474
DeepCCS[M-2H]-204.63430932474
DeepCCS[M+Na]+179.86130932474
AllCCS[M+H]+180.932859911
AllCCS[M+H-H2O]+177.432859911
AllCCS[M+NH4]+184.132859911
AllCCS[M+Na]+185.132859911
AllCCS[M-H]-186.532859911
AllCCS[M+Na-2H]-186.532859911
AllCCS[M+HCOO]-186.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+)-GaleonCOC1=CC2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O3572.1Standard polar33892256
(+)-GaleonCOC1=CC2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O2705.0Standard non polar33892256
(+)-GaleonCOC1=CC2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O2760.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+)-Galeon,1TMS,isomer #1COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CCC(=O)CCCC22937.4Semi standard non polar33892256
(+)-Galeon,1TMS,isomer #2COC1=CC2=CC=C1OC1=C(O)C=CC(=C1)CCC(O[Si](C)(C)C)=CCCC22887.9Semi standard non polar33892256
(+)-Galeon,1TMS,isomer #3COC1=CC2=CC=C1OC1=C(O)C=CC(=C1)CC=C(O[Si](C)(C)C)CCCC22883.4Semi standard non polar33892256
(+)-Galeon,2TMS,isomer #1COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CCC(O[Si](C)(C)C)=CCCC22910.7Semi standard non polar33892256
(+)-Galeon,2TMS,isomer #1COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CCC(O[Si](C)(C)C)=CCCC22718.3Standard non polar33892256
(+)-Galeon,2TMS,isomer #2COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CC=C(O[Si](C)(C)C)CCCC22931.8Semi standard non polar33892256
(+)-Galeon,2TMS,isomer #2COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C)C=CC(=C1)CC=C(O[Si](C)(C)C)CCCC22715.2Standard non polar33892256
(+)-Galeon,1TBDMS,isomer #1COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CCC(=O)CCCC23154.0Semi standard non polar33892256
(+)-Galeon,1TBDMS,isomer #2COC1=CC2=CC=C1OC1=C(O)C=CC(=C1)CCC(O[Si](C)(C)C(C)(C)C)=CCCC23107.0Semi standard non polar33892256
(+)-Galeon,1TBDMS,isomer #3COC1=CC2=CC=C1OC1=C(O)C=CC(=C1)CC=C(O[Si](C)(C)C(C)(C)C)CCCC23121.2Semi standard non polar33892256
(+)-Galeon,2TBDMS,isomer #1COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CCC(O[Si](C)(C)C(C)(C)C)=CCCC23350.9Semi standard non polar33892256
(+)-Galeon,2TBDMS,isomer #1COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CCC(O[Si](C)(C)C(C)(C)C)=CCCC23098.2Standard non polar33892256
(+)-Galeon,2TBDMS,isomer #2COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CC=C(O[Si](C)(C)C(C)(C)C)CCCC23381.2Semi standard non polar33892256
(+)-Galeon,2TBDMS,isomer #2COC1=CC2=CC=C1OC1=C(O[Si](C)(C)C(C)(C)C)C=CC(=C1)CC=C(O[Si](C)(C)C(C)(C)C)CCCC23080.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Galeon GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-0096000000-adec5086c229b4118c102017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Galeon GC-MS (1 TMS) - 70eV, Positivesplash10-008a-3039000000-56238ad213bbdc49b2f52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+)-Galeon 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 - (+)-Galeon 10V, Positive-QTOFsplash10-004i-0009000000-22562d9b33c1b5ee013b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 20V, Positive-QTOFsplash10-004i-0019000000-9961b7891c3e009857732016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 40V, Positive-QTOFsplash10-0a6u-0094000000-9b3e7c919a6f02b440be2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 10V, Negative-QTOFsplash10-004i-0009000000-659f2d6bb10c91dbc25a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 20V, Negative-QTOFsplash10-004i-0009000000-4936bc3da2815eff2fbe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 40V, Negative-QTOFsplash10-0a4l-2096000000-d6b77a3595f3bf03e1b12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 10V, Positive-QTOFsplash10-004i-0009000000-d133ab50982257e6dd6b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 20V, Positive-QTOFsplash10-0a6r-0009000000-88b108bce63b66e6aba52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 40V, Positive-QTOFsplash10-0059-0090000000-545cc8edd9030b74befd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 10V, Negative-QTOFsplash10-004i-0009000000-976dd6ecdf84064dc4ff2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 20V, Negative-QTOFsplash10-056r-0029000000-e641917637d2faaf1eb82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-Galeon 40V, Negative-QTOFsplash10-0a4i-0090000000-1eb05daf300d5f36d4722021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB008141
KNApSAcK IDNot Available
Chemspider ID17273581
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16116346
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
(+)-Galeon → 3,4,5-trihydroxy-6-({17-methoxy-10-oxo-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3,5,7(20),15,18-hexaen-4-yl}oxy)oxane-2-carboxylic aciddetails