4,5',8-Trimethylpsoralen (CHEM016120)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-20 16:15:30 UTC
Update Date2016-11-09 01:15:20 UTC
Accession NumberCHEM016120
Identification
Common Name4,5',8-Trimethylpsoralen
ClassSmall Molecule
Description7H-Furo[3,2-g]chromen-7-one in which positions 2, 5, and 9 are substituted by methyl groups. Like other psoralens, trioxsalen causes photosensitization of the skin. It is administered orally in conjunction with UV-A for phototherapy treatment of vitiligo. After photoactivation it creates interstrand cross-links in DNA, inhibiting DNA synthesis and cell division, and can lead to cell injury; recovery from the cell injury may be followed by increased melanisation of the epidermis.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • IARC Carcinogens Group 3
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2',4,8-TrimethylpsoralenChEBI
4,5',8-TrimethylpsoralenChEBI
4,8,5'-TrimethylpsoralenChEBI
6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactoneChEBI
TrimethylpsoralenChEBI
TrioxisalenoChEBI
TrioxysalenChEBI
TrioxysaleneChEBI
TrioxysalenumChEBI
TrisoralenKegg
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, delta-lactoneGenerator
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, delta-lactoneGenerator
6-Hydroxy-beta,2,7-trimethyl-5-benzofuranacrylate, delta-lactoneGenerator
6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylate, δ-lactoneGenerator
6-Hydroxy-β,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactoneGenerator
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylate, δ-lactoneGenerator, HMDB
6-Hydroxy-b,2,7-trimethyl-5-benzofuranacrylic acid, δ-lactoneGenerator, HMDB
TrioxisalenumMeSH, HMDB
2,5,9-Trimethyl-7H-furo(3,2-g)benzopyran-7-oneMeSH, HMDB
ICN brand OF trioxsalenMeSH, HMDB
Chemical FormulaC14H12O3
Average Molecular Mass228.243 g/mol
Monoisotopic Mass228.079 g/mol
CAS Registry Number3902-71-4
IUPAC Name2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
Traditional Nametrioxsalen
SMILESCC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1
InChI IdentifierInChI=1S/C14H12O3/c1-7-4-12(15)17-14-9(3)13-10(6-11(7)14)5-8(2)16-13/h4-6H,1-3H3
InChI KeyFMHHVULEAZTJMA-UHFFFAOYSA-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
  • Pyranone
  • Benzenoid
  • Pyran
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
logP3.26ALOGPS
logP2.95ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area39.44 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity64.86 m³·mol⁻¹ChemAxon
Polarizability24.77 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0h10-0960000000-966d52d94de4b47d3acdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-dcfc8fb3d1851500be83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fb9-0090000000-9cf76c0cd3483f70877eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ik9-1930000000-364eb5a4711246301410Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-c823a179ff02e7127dc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-e4873a737dacdeebcb1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003f-2920000000-c752e5912988325469f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-c89325e1a7192ec227f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-971e5b85c60e64223aa5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gvk-1930000000-c960ea7d61bacac4f3dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-f0e0fc28215258fdeb31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0190000000-11b09e07d8088345c5cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-0690000000-74d27c4f6ef3bff95576Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB04571
HMDB IDHMDB0015575
FooDB IDFDB001510
Phenol Explorer IDNot Available
KNApSAcK IDC00002502
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTrioxsalen
Chemspider ID5383
ChEBI ID28329
PubChem Compound ID5585
Kegg Compound IDC09314
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. van Coevorden AM, Kamphof WG, van Sonderen E, Bruynzeel DP, Coenraads PJ: Comparison of oral psoralen-UV-A with a portable tanning unit at home vs hospital-administered bath psoralen-UV-A in patients with chronic hand eczema: an open-label randomized controlled trial of efficacy. Arch Dermatol. 2004 Dec;140(12):1463-6.
2. Higuchi M, Yamayoshi A, Kobori A, Yamaoka T, Murakami A: Synthesis and properties of photo-reactive antisense oligonucleotides containing 2'-O-psoralen-conjugated adenosine. Nucleic Acids Symp Ser (Oxf). 2005;(49):331-2.
3. Thazhathveetil AK, Liu ST, Indig FE, Seidman MM: Psoralen conjugates for visualization of genomic interstrand cross-links localized by laser photoactivation. Bioconjug Chem. 2007 Mar-Apr;18(2):431-7.
4. Goldenberg M, Welsh J, Haas R, Rideout DC, Cantor CR: Synthesis and properties of novel psoralen derivatives. Biochemistry. 1988 Sep 6;27(18):6971-6. doi: 10.1021/bi00418a045.
5. Kaidbey KH, Kligman AM: Photopigmentation with trioxsalen. Arch Dermatol. 1974 May;109(5):674-7.
6. Sehgal VN: Editorial: Effectiveness of trioxsalen therapy for vitiligo. Arch Dermatol. 1974 Dec;110(6):957-8. doi: 10.1001/archderm.1974.01630120089029.