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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 03:04:33 UTC
Update Date2022-03-07 02:57:00 UTC
HMDB IDHMDB0041394
Secondary Accession Numbers
  • HMDB41394
Metabolite Identification
Common NameKhelmarin D
DescriptionKhelmarin D belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety. Khelmarin D has been detected, but not quantified in, citrus. This could make khelmarin D a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Khelmarin D.
Structure
Data?1563863658
SynonymsNot Available
Chemical FormulaC28H24O8
Average Molecular Weight488.4854
Monoisotopic Molecular Weight488.147117744
IUPAC Name14-({8,8-dimethyl-2-oxo-2H,8H-pyrano[2,3-f]chromen-5-yl}oxy)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-4-one
Traditional Name14-({8,8-dimethyl-2-oxopyrano[2,3-f]chromen-5-yl}oxy)-13-hydroxy-12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),5,8-tetraen-4-one
CAS Registry Number175923-64-5
SMILES
CC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C(OC1C(O)C(C)(C)OC3=C1C1=C(C=CC(=O)O1)C=C3)=C2
InChI Identifier
InChI=1S/C28H24O8/c1-27(2)12-11-16-19(35-27)13-18(15-7-10-21(30)34-24(15)16)32-25-22-17(36-28(3,4)26(25)31)8-5-14-6-9-20(29)33-23(14)22/h5-13,25-26,31H,1-4H3
InChI KeySVNBKSLEKBMPRA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as angular pyranocoumarins. These are organic compounds containing a pyran (or a hydrogenated derivative) angularly fused to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassPyranocoumarins
Direct ParentAngular pyranocoumarins
Alternative Parents
Substituents
  • Angular pyranocoumarin
  • Pyranochromene
  • 2,2-dimethyl-1-benzopyran
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Secondary alcohol
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.98 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP4.32ALOGPS
logP3.86ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)12.83ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area100.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity131.69 m³·mol⁻¹ChemAxon
Polarizability48.89 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]+208.83431661259
DarkChem[M-H]-207.39931661259
DeepCCS[M+H]+211.50130932474
DeepCCS[M-H]-209.10630932474
DeepCCS[M-2H]-241.9930932474
DeepCCS[M+Na]+217.41430932474
AllCCS[M+H]+214.332859911
AllCCS[M+H-H2O]+212.132859911
AllCCS[M+NH4]+216.332859911
AllCCS[M+Na]+216.832859911
AllCCS[M-H]-214.132859911
AllCCS[M+Na-2H]-214.032859911
AllCCS[M+HCOO]-214.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Khelmarin DCC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C(OC1C(O)C(C)(C)OC3=C1C1=C(C=CC(=O)O1)C=C3)=C25272.8Standard polar33892256
Khelmarin DCC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C(OC1C(O)C(C)(C)OC3=C1C1=C(C=CC(=O)O1)C=C3)=C23908.1Standard non polar33892256
Khelmarin DCC1(C)OC2=C(C=C1)C1=C(C=CC(=O)O1)C(OC1C(O)C(C)(C)OC3=C1C1=C(C=CC(=O)O1)C=C3)=C24287.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Khelmarin D,1TMS,isomer #1CC1(C)C=CC2=C(C=C(OC3C4=C5OC(=O)C=CC5=CC=C4OC(C)(C)C3O[Si](C)(C)C)C3=C2OC(=O)C=C3)O14038.1Semi standard non polar33892256
Khelmarin D,1TBDMS,isomer #1CC1(C)C=CC2=C(C=C(OC3C4=C5OC(=O)C=CC5=CC=C4OC(C)(C)C3O[Si](C)(C)C(C)(C)C)C3=C2OC(=O)C=C3)O14249.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Khelmarin D GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-0090800000-9bfd34ac035ce6f93a4b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Khelmarin D GC-MS (1 TMS) - 70eV, Positivesplash10-00y1-4030090000-0f22503f566a787d2cac2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Khelmarin D 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 - Khelmarin D 10V, Positive-QTOFsplash10-000i-1000900000-07043e2a8fc2b460853d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 20V, Positive-QTOFsplash10-033a-1010900000-d5da1ee8ebaf1e4fcfbe2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 40V, Positive-QTOFsplash10-0109-9631200000-502b851a9707d6e13e942017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 10V, Negative-QTOFsplash10-000i-0000900000-c3632a38464b64275ed52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 20V, Negative-QTOFsplash10-00ko-0021900000-7f885844462aca5336712017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 40V, Negative-QTOFsplash10-002b-3790000000-76246440620628e307782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 10V, Negative-QTOFsplash10-000i-0000900000-56c6c84a86381d76ed8c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 20V, Negative-QTOFsplash10-052s-0000900000-819742f730385e29a6d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 40V, Negative-QTOFsplash10-02t9-2432900000-8bc8f618d458f6ad95d52021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 10V, Positive-QTOFsplash10-000i-0000900000-2e1ff1a35957bc989df22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 20V, Positive-QTOFsplash10-0002-0090700000-0a4d4dfab08a5064e78c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Khelmarin D 40V, Positive-QTOFsplash10-03ka-2580900000-bd6be5ab52124d8c32e72021-09-22Wishart 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 IDFDB021332
KNApSAcK IDNot Available
Chemspider ID8847988
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10672636
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1892001
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.. .