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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:02 UTC
HMDB IDHMDB0015575
Secondary Accession Numbers
  • HMDB15575
Metabolite Identification
Common NameTrioxsalen
DescriptionTrioxsalen, also known as trimethylpsoralen, trioxysalen or trisoralen, belongs to the group of drugs called psoralens. It is also known as a furanocoumarin (PMID: 3196695 ). Trioxsalen is a pigmenting photosensitizing agent used to treat vitiligo, a condition characterized by loss of skin color (PMID: 4828534 , 4441118 ). It is administered in conjunction with ultraviolet light A (UVA) to increase the skin's sensitivity to sunlight. Trioxsalen functions through inducing interstrand crosslinks in DNA. It has been reported that use of trioxsalen increases the chance of skin cancer and cataracts. Trioxsalen is only found in individuals that have used or taken this drug.
Structure
Data?1582753312
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 Weight228.2433
Monoisotopic Molecular Weight228.07864425
IUPAC Name2,5,9-trimethyl-7H-furo[3,2-g]chromen-7-one
Traditional Nametrioxsalen
CAS Registry Number3902-71-4
SMILES
CC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O1
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility21.51 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available147.445http://allccs.zhulab.cn/database/detail?ID=AllCCS00001388
Predicted Molecular 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
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]+152.49831661259
DarkChem[M-H]-153.72731661259
DeepCCS[M+H]+155.82230932474
DeepCCS[M-H]-153.46430932474
DeepCCS[M-2H]-186.70230932474
DeepCCS[M+Na]+161.91630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrioxsalenCC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O12948.4Standard polar33892256
TrioxsalenCC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O12166.5Standard non polar33892256
TrioxsalenCC1=CC2=CC3=C(OC(=O)C=C3C)C(C)=C2O12157.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trioxsalen GC-MS (Non-derivatized) - 70eV, Positivesplash10-0h10-0960000000-966d52d94de4b47d3acd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trioxsalen 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 - Trioxsalen 10V, Positive-QTOFsplash10-004i-0090000000-dcfc8fb3d1851500be832016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 20V, Positive-QTOFsplash10-0fb9-0090000000-9cf76c0cd3483f70877e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 40V, Positive-QTOFsplash10-0ik9-1930000000-364eb5a47112463014102016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 10V, Negative-QTOFsplash10-004i-0090000000-c823a179ff02e7127dc92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 20V, Negative-QTOFsplash10-004i-0090000000-e4873a737dacdeebcb1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 40V, Negative-QTOFsplash10-003f-2920000000-c752e5912988325469f02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 10V, Positive-QTOFsplash10-004i-0090000000-c89325e1a7192ec227f42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 20V, Positive-QTOFsplash10-004i-0090000000-971e5b85c60e64223aa52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 40V, Positive-QTOFsplash10-0gvk-1930000000-c960ea7d61bacac4f3df2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 10V, Negative-QTOFsplash10-004i-0090000000-f0e0fc28215258fdeb312021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 20V, Negative-QTOFsplash10-004i-0190000000-11b09e07d8088345c5cb2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trioxsalen 40V, Negative-QTOFsplash10-004i-0690000000-74d27c4f6ef3bff955762021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04571 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04571 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04571
Phenol Explorer Compound IDNot Available
FooDB IDFDB001510
KNApSAcK IDC00002502
Chemspider ID5383
KEGG Compound IDC09314
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrioxsalen
METLIN IDNot Available
PubChem Compound5585
PDB IDNot Available
ChEBI ID28329
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1195461
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:15611423 ]
  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. [PubMed:17150768 ]
  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. [PubMed:17373769 ]
  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. [PubMed:3196695 ]
  5. Kaidbey KH, Kligman AM: Photopigmentation with trioxsalen. Arch Dermatol. 1974 May;109(5):674-7. [PubMed:4828534 ]
  6. Sehgal VN: Editorial: Effectiveness of trioxsalen therapy for vitiligo. Arch Dermatol. 1974 Dec;110(6):957-8. doi: 10.1001/archderm.1974.01630120089029. [PubMed:4441118 ]