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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:44:51 UTC
Update Date2022-03-07 02:54:36 UTC
HMDB IDHMDB0035732
Secondary Accession Numbers
  • HMDB35732
Metabolite Identification
Common NameDukunolide D
DescriptionDukunolide D 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. Dukunolide D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, dukunolide D has been detected, but not quantified in, fruits. This could make dukunolide D a potential biomarker for the consumption of these foods.
Structure
Data?1563862763
Synonyms
ValueSource
(+)-Dukunolide DHMDB
1,1'-Dimethyl-2,2'-oxydiethyl dibenzoateHMDB
Dipropylene glycol dibenzoateHMDB
Oxydipropane-1,2-diyl dibenzoateHMDB
Propanol, oxybis-, dibenzoateHMDB
Chemical FormulaC26H28O8
Average Molecular Weight468.4957
Monoisotopic Molecular Weight468.178417872
IUPAC Name17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione
Traditional Name17-(furan-3-yl)-2,10-dihydroxy-3,8,8,16-tetramethyl-4,18-dioxapentacyclo[10.7.1.0²,¹⁰.0³,⁷.0¹⁶,²⁰]icosa-1(20),12-diene-5,9,19-trione
CAS Registry Number101560-02-5
SMILES
CC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C1
InChI Identifier
InChI=1S/C26H28O8/c1-22(2)15-10-16(27)34-24(15,4)26(31)18-17-13(11-25(26,30)21(22)29)6-5-8-23(17,3)19(33-20(18)28)14-7-9-32-12-14/h6-7,9,12,15,19,30-31H,5,8,10-11H2,1-4H3
InChI KeyWUQGZJQZKDLECQ-UHFFFAOYSA-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 Parents
Substituents
  • Naphthopyran
  • Naphthofuran
  • Naphthalene
  • Dihydropyranone
  • Dicarboxylic acid or derivatives
  • Gamma butyrolactone
  • Pyran
  • Cyclic alcohol
  • Furan
  • Heteroaromatic compound
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Tetrahydrofuran
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • 1,2-diol
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point295.5 - 298 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP2.34ALOGPS
logP2.2ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)11.38ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area123.27 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity118.16 m³·mol⁻¹ChemAxon
Polarizability47.29 ųChemAxon
Number of Rings6ChemAxon
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]+203.50431661259
DarkChem[M-H]-198.10231661259
DeepCCS[M-2H]-244.37430932474
DeepCCS[M+Na]+220.29130932474
AllCCS[M+H]+206.832859911
AllCCS[M+H-H2O]+204.732859911
AllCCS[M+NH4]+208.732859911
AllCCS[M+Na]+209.232859911
AllCCS[M-H]-214.232859911
AllCCS[M+Na-2H]-215.032859911
AllCCS[M+HCOO]-216.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dukunolide DCC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C15033.1Standard polar33892256
Dukunolide DCC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C13149.5Standard non polar33892256
Dukunolide DCC12OC(=O)CC1C(C)(C)C(=O)C1(O)CC3=CCCC4(C)C(OC(=O)C(=C34)C21O)C1=COC=C13876.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dukunolide D,1TMS,isomer #1CC1(C)C(=O)C2(O[Si](C)(C)C)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O)C2(C)OC(=O)CC123658.7Semi standard non polar33892256
Dukunolide D,1TMS,isomer #2CC1(C)C(=O)C2(O)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O[Si](C)(C)C)C2(C)OC(=O)CC123662.8Semi standard non polar33892256
Dukunolide D,2TMS,isomer #1CC1(C)C(=O)C2(O[Si](C)(C)C)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O[Si](C)(C)C)C2(C)OC(=O)CC123609.3Semi standard non polar33892256
Dukunolide D,1TBDMS,isomer #1CC1(C)C(=O)C2(O[Si](C)(C)C(C)(C)C)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O)C2(C)OC(=O)CC123907.0Semi standard non polar33892256
Dukunolide D,1TBDMS,isomer #2CC1(C)C(=O)C2(O)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O[Si](C)(C)C(C)(C)C)C2(C)OC(=O)CC123904.1Semi standard non polar33892256
Dukunolide D,2TBDMS,isomer #1CC1(C)C(=O)C2(O[Si](C)(C)C(C)(C)C)CC3=CCCC4(C)C3=C(C(=O)OC4C3=COC=C3)C2(O[Si](C)(C)C(C)(C)C)C2(C)OC(=O)CC124101.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide D GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-8265900000-c34c57fb27d3982e37582017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide D GC-MS (2 TMS) - 70eV, Positivesplash10-0gi4-9210080000-5ea1e8a9def7bfc53f752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide D GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide D GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide D GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide D GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dukunolide D GC-MS ("Dukunolide D,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 D 10V, Positive-QTOFsplash10-014i-0000900000-05fe7f8d93d043bf34332016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 20V, Positive-QTOFsplash10-0uxr-0000900000-6fdaa93c85af22bc5e1c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 40V, Positive-QTOFsplash10-00kk-9501000000-2a02a2ad319d0a5f3dd42016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 10V, Negative-QTOFsplash10-01b9-0000900000-8b9d04d5395dfda919812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 20V, Negative-QTOFsplash10-01b9-1001900000-8eeebfd2f38b366c0b462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 40V, Negative-QTOFsplash10-0006-9406200000-9bbd100d16ee7179b3c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 10V, Positive-QTOFsplash10-014i-0000900000-cc33c2bebaeb72d73a582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 20V, Positive-QTOFsplash10-0gdi-0100900000-8a3998899426dbf3542a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 40V, Positive-QTOFsplash10-0007-5491400000-57a12129d86a786ec4522021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 10V, Negative-QTOFsplash10-014i-0000900000-7dccc54e01e7cdbb03b92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 20V, Negative-QTOFsplash10-014i-0000900000-9e5d2ae0d9d409a740392021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dukunolide D 40V, Negative-QTOFsplash10-01dj-7079600000-fbb87fc0e88f252b94852021-09-22Wishart 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 IDFDB014460
KNApSAcK IDC00035090
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13970419
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.. .