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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:45:55 UTC
Update Date2022-03-07 02:54:14 UTC
HMDB IDHMDB0034837
Secondary Accession Numbers
  • HMDB34837
Metabolite Identification
Common NameLansiumarin A
DescriptionLansiumarin A belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one. Lansiumarin A has been detected, but not quantified in, fruits. This could make lansiumarin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Lansiumarin A.
Structure
Data?1563862622
SynonymsNot Available
Chemical FormulaC21H20O5
Average Molecular Weight352.3805
Monoisotopic Molecular Weight352.13107375
IUPAC Name9-{[(2E)-3,7-dimethyl-6-oxoocta-2,7-dien-1-yl]oxy}-7H-furo[3,2-g]chromen-7-one
Traditional Name9-{[(2E)-3,7-dimethyl-6-oxoocta-2,7-dien-1-yl]oxy}furo[3,2-g]chromen-7-one
CAS Registry Number205115-73-7
SMILES
C\C(CCC(=O)C(C)=C)=C/COC1=C2OC(=O)C=CC2=CC2=C1OC=C2
InChI Identifier
InChI=1S/C21H20O5/c1-13(2)17(22)6-4-14(3)8-10-25-21-19-16(9-11-24-19)12-15-5-7-18(23)26-20(15)21/h5,7-9,11-12H,1,4,6,10H2,2-3H3/b14-8+
InChI KeyXWVDCVZOOVTJKF-RIYZIHGNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
Alternative Parents
Substituents
  • Psoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Alpha-branched alpha,beta-unsaturated-ketone
  • Acryloyl-group
  • Heteroaromatic compound
  • Furan
  • Enone
  • Alpha,beta-unsaturated ketone
  • Lactone
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen 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 Solubility0.77 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.91ALOGPS
logP4.2ChemAxon
logS-4.4ALOGPS
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area65.74 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.39 m³·mol⁻¹ChemAxon
Polarizability37.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+184.17131661259
DarkChem[M-H]-181.72731661259
DeepCCS[M+H]+190.30830932474
DeepCCS[M-H]-187.74530932474
DeepCCS[M-2H]-222.24130932474
DeepCCS[M+Na]+198.19430932474
AllCCS[M+H]+183.332859911
AllCCS[M+H-H2O]+180.432859911
AllCCS[M+NH4]+186.032859911
AllCCS[M+Na]+186.832859911
AllCCS[M-H]-187.232859911
AllCCS[M+Na-2H]-186.632859911
AllCCS[M+HCOO]-186.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lansiumarin AC\C(CCC(=O)C(C)=C)=C/COC1=C2OC(=O)C=CC2=CC2=C1OC=C23822.4Standard polar33892256
Lansiumarin AC\C(CCC(=O)C(C)=C)=C/COC1=C2OC(=O)C=CC2=CC2=C1OC=C22907.0Standard non polar33892256
Lansiumarin AC\C(CCC(=O)C(C)=C)=C/COC1=C2OC(=O)C=CC2=CC2=C1OC=C23028.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lansiumarin A,1TMS,isomer #1C=C(C)C(=CC/C(C)=C/COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C3070.2Semi standard non polar33892256
Lansiumarin A,1TMS,isomer #1C=C(C)C(=CC/C(C)=C/COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C2963.7Standard non polar33892256
Lansiumarin A,1TBDMS,isomer #1C=C(C)C(=CC/C(C)=C/COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C(C)(C)C3278.2Semi standard non polar33892256
Lansiumarin A,1TBDMS,isomer #1C=C(C)C(=CC/C(C)=C/COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C(C)(C)C3154.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lansiumarin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9265000000-4ef43dc2d9eaf2c262792017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lansiumarin A 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 - Lansiumarin A 10V, Positive-QTOFsplash10-0udi-0319000000-f4e8ee3e119a4574ba5f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 20V, Positive-QTOFsplash10-0udi-5975000000-d4da7b21aeb6838801252016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 40V, Positive-QTOFsplash10-0udi-9530000000-e97913dc90690bf0cdf02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 10V, Negative-QTOFsplash10-0udi-0029000000-2a26d39398849818aac82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 20V, Negative-QTOFsplash10-0udi-2495000000-a3bb96261201c0f096112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 40V, Negative-QTOFsplash10-0a4i-1920000000-1e5bb835f561756a65dc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 10V, Negative-QTOFsplash10-0udi-0097000000-9babbd03e2eebf16773a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 20V, Negative-QTOFsplash10-0udi-2259000000-f01a094d82cc7525ba9a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 40V, Negative-QTOFsplash10-0udi-2690000000-5042d46e4619ae6496572021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 10V, Positive-QTOFsplash10-0udi-0092000000-890301eb498ad215f41c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 20V, Positive-QTOFsplash10-0udi-7491000000-16a2fc177da9cb9e34af2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lansiumarin A 40V, Positive-QTOFsplash10-0fur-8591000000-7d2fbc2b5717301669c52021-09-23Wishart 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 IDFDB013403
KNApSAcK IDC00058567
Chemspider ID9966973
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11792299
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1845831
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.. .