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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:41:29 UTC
Update Date2022-03-07 02:54:35 UTC
HMDB IDHMDB0035683
Secondary Accession Numbers
  • HMDB35683
Metabolite Identification
Common NameDukunolide A
Description3-Hydroxy-1-phenyl-1-hexadecanone, also known as 1-benzoyl-2-pentadecanol, belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. 3-Hydroxy-1-phenyl-1-hexadecanone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862755
Synonyms
ValueSource
1-Benzoyl-2-pentadecanolHMDB
1,1,1-trifluoro-2-OctanolHMDB
1,1,1-Trifluorooctan-2-olHMDB
Chemical FormulaC26H26O9
Average Molecular Weight482.4792
Monoisotopic Molecular Weight482.15768243
IUPAC Name18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]henicosa-1(21),13-diene-5,10,20-trione
Traditional Name18-(furan-3-yl)-2,11-dihydroxy-3,9,9,17-tetramethyl-4,7,19-trioxahexacyclo[11.7.1.0²,¹¹.0³,⁸.0⁶,⁸.0¹⁷,²¹]henicosa-1(21),13-diene-5,10,20-trione
CAS Registry Number97804-04-1
SMILES
CC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1
InChI Identifier
InChI=1S/C26H26O9/c1-21(2)20(29)24(30)10-12-6-5-8-22(3)14(12)15(18(27)33-16(22)13-7-9-32-11-13)25(24,31)23(4)26(21)17(34-26)19(28)35-23/h6-7,9,11,16-17,30-31H,5,8,10H2,1-4H3
InChI KeyBATTZJIKLZSIAU-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty alcohols. These are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentLong-chain fatty alcohols
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Long chain fatty alcohol
  • Butyrophenone
  • Phenylketone
  • Benzoyl
  • Aryl alkyl ketone
  • Aryl ketone
  • Monocyclic benzene moiety
  • Beta-hydroxy ketone
  • Benzenoid
  • Secondary alcohol
  • Ketone
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point279 - 281 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP2.04ALOGPS
logP1.88ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)11.33ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area135.8 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity117.14 m³·mol⁻¹ChemAxon
Polarizability47.54 ųChemAxon
Number of Rings7ChemAxon
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]+206.75831661259
DarkChem[M-H]-192.82531661259
DeepCCS[M-2H]-244.73130932474
DeepCCS[M+Na]+220.22230932474
AllCCS[M+H]+208.232859911
AllCCS[M+H-H2O]+206.232859911
AllCCS[M+NH4]+210.032859911
AllCCS[M+Na]+210.532859911
AllCCS[M-H]-215.932859911
AllCCS[M+Na-2H]-216.632859911
AllCCS[M+HCOO]-217.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dukunolide ACC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C14973.7Standard polar33892256
Dukunolide ACC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C13176.0Standard non polar33892256
Dukunolide ACC12OC(=O)C3OC13C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C13852.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dukunolide A,1TMS,isomer #1CC12CCC=C3CC4(O[Si](C)(C)C)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O)C(=C31)C(=O)OC2C1=COC=C13626.0Semi standard non polar33892256
Dukunolide A,1TMS,isomer #2CC12CCC=C3CC4(O)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O[Si](C)(C)C)C(=C31)C(=O)OC2C1=COC=C13633.9Semi standard non polar33892256
Dukunolide A,2TMS,isomer #1CC12CCC=C3CC4(O[Si](C)(C)C)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O[Si](C)(C)C)C(=C31)C(=O)OC2C1=COC=C13594.6Semi standard non polar33892256
Dukunolide A,1TBDMS,isomer #1CC12CCC=C3CC4(O[Si](C)(C)C(C)(C)C)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O)C(=C31)C(=O)OC2C1=COC=C13875.7Semi standard non polar33892256
Dukunolide A,1TBDMS,isomer #2CC12CCC=C3CC4(O)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O[Si](C)(C)C(C)(C)C)C(=C31)C(=O)OC2C1=COC=C13882.4Semi standard non polar33892256
Dukunolide A,2TBDMS,isomer #1CC12CCC=C3CC4(O[Si](C)(C)C(C)(C)C)C(=O)C(C)(C)C56OC5C(=O)OC6(C)C4(O[Si](C)(C)C(C)(C)C)C(=C31)C(=O)OC2C1=COC=C14094.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f6w-9187700000-0c2a7c908194de1bc5f32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide A GC-MS (2 TMS) - 70eV, Positivesplash10-002f-9500682000-d4a39e6552e42584c5712017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide A GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide A GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide A GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide A GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide A GC-MS ("Dukunolide A,1TMS,#2" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 10V, Positive-QTOFsplash10-001i-0000900000-da8ac3e0960d9da6301a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 20V, Positive-QTOFsplash10-00lr-1001900000-a7a4ec4957242dee0a6b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 40V, Positive-QTOFsplash10-0002-7709200000-399347021ab16db3424a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 10V, Negative-QTOFsplash10-001r-0000900000-bd77068acce7dc5d8ed72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 20V, Negative-QTOFsplash10-01qi-1100900000-713c9a5813e43e4afe8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 40V, Negative-QTOFsplash10-0aos-9806800000-317daa3f79d0b756a9b62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 10V, Negative-QTOFsplash10-001i-0000900000-e224776f4657f4af7bc62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 20V, Negative-QTOFsplash10-001i-2001900000-7d43705e485ecb09784a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 40V, Negative-QTOFsplash10-000i-2034900000-d50d05351d98039d86e22021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 10V, Positive-QTOFsplash10-001i-0000900000-0b0163d042220f3726112021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 20V, Positive-QTOFsplash10-001i-1009800000-7a79187b060f7832fe212021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide A 40V, Positive-QTOFsplash10-000y-2590500000-7d4e6f2c0654820249762021-09-25Wishart LabView Spectrum
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 IDFDB014393
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751842
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.. .