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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:42:16 UTC
Update Date2019-07-23 06:14:43 UTC
HMDB IDHMDB0033930
Secondary Accession Numbers
  • HMDB33930
Metabolite Identification
Common NameAngelicin
DescriptionAngelicin, also known as isopsoralen or bakuchicin, 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. Furocoumarin photochemotherapy is known to induce a number of side-effects including erythema, edema, hyperpigmentation, and premature aging of skin. Furocoumarins can cause photosensitization dermatitis especially if these compounds come into contact with the skin. If inhaled, remove to fresh air. Angelicin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Angelicin is found, on average, in the highest concentration within parsnips. Angelicin has also been detected, but not quantified in, several different foods, such as fats and oils, figs, wild celeries, corianders, and herbs and spices. This could make angelicin a potential biomarker for the consumption of these foods. Angelicin is a potentially toxic compound. All photobiological effects of furocoumarins result from their photochemical reactions. The mechanism of action many furocoumarins is based on their ability to form photoadducts with DNA and other cellular components such as RNA, proteins, and several proteins found in the membrane such as phospholipases A2 and C, Ca-dependent and cAMPdependent protein-kinase and epidermal growth factor. Furocoumarins intercalate between base pairs of DNA and after ultraviolet-A irradiation, giving cycloadducts.
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

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point138 - 139.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.08Not Available
Predicted 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
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052o-1900000000-e433073a06547646bc69Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-aa1adff2459dc4ba52deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-e3913fd1e50c49b503ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-0900000000-1a7322ca712708e85891Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-0fb3e93d63c26fc514f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-9305ce66dc73cd6363e7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ko-1900000000-d860e98711eaf835ef5dSpectrum
MSMass Spectrum (Electron Ionization)splash10-000i-2900000000-b75bda2977a6c5f4a825Spectrum
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
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.. .