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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:42:16 UTC
Update Date2022-03-07 02:53:54 UTC
HMDB IDHMDB0033930
Secondary Accession Numbers
  • HMDB33930
Metabolite Identification
Common NameAngelicin
DescriptionAngelicin, also known as isopsoralen, belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Angelicin is found, on average, in the highest concentration within parsnips (Pastinaca sativa). Angelicin has also been detected, but not quantified in, several different foods, such as figs (Ficus carica), green vegetables, wild celeries (Apium graveolens), corianders (Coriandrum sativum), and herbs and spices. This could make angelicin a potential biomarker for the consumption of these foods. Angelicin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Angelicin.
Structure
Data?1563862483
Synonyms
ValueSource
IsopsoralenChEBI
2H-furo[2,3-H]-1-Benzopyran-2-oneHMDB
2H-furo[2,3-H]Chromen-2-oneHMDB
3-(4-Hydroxy-5-benzofuranyl)-2-propenoic acid gamma-lactoneHMDB
4-Hydroxy-5-benzofuranacrylic acid gamma-lactoneHMDB
AngecinHMDB
AngelecinHMDB
BakuchicinHMDB
furo[2,3-H]CoumarinHMDB
furo[5',4':7,8]CoumarinHMDB
IsopsoralinHMDB
Chemical FormulaC11H6O3
Average Molecular Weight186.166
Monoisotopic Molecular Weight186.031694053
IUPAC Name2H-furo[2,3-h]chromen-2-one
Traditional Nameangelicin
CAS Registry Number523-50-2
SMILES
[H]C1=C([H])C2=C(O1)C([H])=C([H])C1=C2OC(=O)C([H])=C1[H]
InChI Identifier
InChI=1S/C11H6O3/c12-10-4-2-7-1-3-9-8(5-6-13-9)11(7)14-10/h1-6H
InChI KeyXDROKJSWHURZGO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentAngular furanocoumarins
Alternative Parents
Substituents
  • Angular furanocoumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point138 - 139.5 °CNot Available
Boiling Point360.00 to 362.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility859.6 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.08Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.03ALOGPS
logP1.94ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.44 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity50.39 m³·mol⁻¹ChemAxon
Polarizability17.93 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.60331661259
DarkChem[M-H]-137.83631661259
DeepCCS[M+H]+155.89230932474
DeepCCS[M-H]-153.49630932474
DeepCCS[M-2H]-187.20230932474
DeepCCS[M+Na]+162.20530932474
AllCCS[M+H]+137.332859911
AllCCS[M+H-H2O]+132.732859911
AllCCS[M+NH4]+141.632859911
AllCCS[M+Na]+142.932859911
AllCCS[M-H]-137.232859911
AllCCS[M+Na-2H]-136.832859911
AllCCS[M+HCOO]-136.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Angelicin[H]C1=C([H])C2=C(O1)C([H])=C([H])C1=C2OC(=O)C([H])=C1[H]3057.9Standard polar33892256
Angelicin[H]C1=C([H])C2=C(O1)C([H])=C([H])C1=C2OC(=O)C([H])=C1[H]1826.2Standard non polar33892256
Angelicin[H]C1=C([H])C2=C(O1)C([H])=C([H])C1=C2OC(=O)C([H])=C1[H]1848.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Angelicin GC-MS (Non-derivatized) - 70eV, Positivesplash10-052o-1900000000-e433073a06547646bc692017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Angelicin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-000i-2900000000-b75bda2977a6c5f4a8252014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 10V, Positive-QTOFsplash10-000i-0900000000-aa1adff2459dc4ba52de2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 20V, Positive-QTOFsplash10-000i-0900000000-e3913fd1e50c49b503cc2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 40V, Positive-QTOFsplash10-00kb-0900000000-1a7322ca712708e858912015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 10V, Negative-QTOFsplash10-000i-0900000000-0fb3e93d63c26fc514f32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 20V, Negative-QTOFsplash10-000i-0900000000-9305ce66dc73cd6363e72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 40V, Negative-QTOFsplash10-00ko-1900000000-d860e98711eaf835ef5d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 10V, Positive-QTOFsplash10-000i-0900000000-f3f07adc83a68e9e76ff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 20V, Positive-QTOFsplash10-0a4r-0900000000-5d2c49a45303742805c02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 40V, Positive-QTOFsplash10-0a59-0900000000-a5ec76b52b95bb267d302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 10V, Negative-QTOFsplash10-000i-0900000000-89e4df10d3690e5a6d152021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 20V, Negative-QTOFsplash10-000i-0900000000-89e4df10d3690e5a6d152021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Angelicin 40V, Negative-QTOFsplash10-0a4r-0900000000-97a40f647a23cfa5279b2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 ID721
FooDB IDFDB012132
KNApSAcK IDC00002450
Chemspider ID10208
KEGG Compound IDC09060
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAngelicin
METLIN IDNot Available
PubChem Compound10658
PDB IDNot Available
ChEBI ID28928
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1010821
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.. .