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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:09 UTC
HMDB IDHMDB0014693
Secondary Accession Numbers
  • HMDB14693
Metabolite Identification
Common NameMethoxsalen
DescriptionMethoxsalen, also known as oxsoralen or 8-methoxypsoralen, belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group. Methoxsalen is a drug which is used for the treatment of psoriasis and vitiligo. Methoxsalen is an extremely weak basic (essentially neutral) compound (based on its pKa). Methoxsalen is a bitter tasting compound. Outside of the human body, Methoxsalen is found, on average, in the highest concentration within a few different foods, such as parsnips, parsley, and celery stalks and in a lower concentration in wild carrots, carrots, and fennels. Methoxsalen has also been detected, but not quantified in, several different foods, such as figs, green vegetables, corianders, dills, and fruits. This could make methoxsalen a potential biomarker for the consumption of these foods. Methoxsalen is a potentially toxic compound.
Structure
Data?1582753209
Synonyms
ValueSource
6-Hydroxy-7-methoxy-5-benzofuranacrylic acid delta-lactoneChEBI
8-Methoxy-2',3',6,7-furocoumarinChEBI
8-Methoxy-4',5':6,7-furocoumarinChEBI
8-Methoxy-[furano-3'.2':6.7-coumarin]ChEBI
8-MethoxyfuranocoumarinChEBI
8-MethoxypsoralenChEBI
8-MOPChEBI
8-MPChEBI
9-Methoxy-7H-furo[3,2-g][1]benzopyran-7-oneChEBI
MeladinineChEBI
MeloxineChEBI
O-MethylxanthotoxolChEBI
OxsoralenChEBI
Ultra mopChEBI
UvadexChEBI
XanthotoxinChEBI
6-Hydroxy-7-methoxy-5-benzofuranacrylate delta-lactoneGenerator
6-Hydroxy-7-methoxy-5-benzofuranacrylate δ-lactoneGenerator
6-Hydroxy-7-methoxy-5-benzofuranacrylic acid δ-lactoneGenerator
MethoxalenHMDB
XanthotoxineHMDB
XanthoxinHMDB
ZanthotoxinHMDB
8 MOPHMDB
Chinoin brand OF methoxsalenHMDB
DermoxHMDB
GeroxalenHMDB
ICN brand 2 OF methoxsalenHMDB
Methoxsalen mex-america brandHMDB
Oxsoralen ultraHMDB
Oxsoralen-ultraHMDB
8 MethoxypsoralenHMDB
AmmoidinHMDB
DB Brand OF methoxsalenHMDB
DeltasoralenHMDB
MeladininaHMDB
Methoxsalen Delta brandHMDB
Mex-america brand OF methoxsalenHMDB
MéladinineHMDB
Sanofi-synthelabo brand OF methoxsalenHMDB
8MOPHMDB
Boehringer ingelheim brand OF methoxsalenHMDB
Galderma brand OF methoxsalenHMDB
Methoxa-domeHMDB
Methoxsalen canderm brandHMDB
Methoxsalen chinoin brandHMDB
Methoxsalen dermatech brandHMDB
Methoxsalen sanofi-synthelabo brandHMDB
PuvalenHMDB
Sanofi synthelabo brand OF methoxsalenHMDB
UltramopHMDB
Canderm brand OF methoxsalenHMDB
Delta Brand OF methoxsalenHMDB
Dermatech brand OF methoxsalenHMDB
ICN brand 1 OF methoxsalenHMDB
ICN brand 3 OF methoxsalenHMDB
Methoxa domeHMDB
Mex america brand OF methoxsalenHMDB
Chemical FormulaC12H8O4
Average Molecular Weight216.192
Monoisotopic Molecular Weight216.042258738
IUPAC Name9-methoxy-7H-furo[3,2-g]chromen-7-one
Traditional Namemethoxsalen
CAS Registry Number298-81-7
SMILES
COC1=C2OC(=O)C=CC2=CC2=C1OC=C2
InChI Identifier
InChI=1S/C12H8O4/c1-14-12-10-8(4-5-15-10)6-7-2-3-9(13)16-11(7)12/h2-6H,1H3
InChI KeyQXKHYNVANLEOEG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 8-methoxypsoralens. These are psoralens containing a methoxy group attached at the C8 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent8-methoxypsoralens
Alternative Parents
Substituents
  • 8-methoxypsoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen 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

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.16 g/LNot Available
LogP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.1ALOGPS
logP1.78ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.85 m³·mol⁻¹ChemAxon
Polarizability20.98 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ri-6940000000-921a3e8adbbde5f7a0c3Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-003b-4950000000-4e2c001531825f6dddcaSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00ri-6940000000-921a3e8adbbde5f7a0c3Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-003b-4950000000-4e2c001531825f6dddcaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1920000000-98f6cfda190045d0762aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-1590000000-f70cf2b0756e8c80c17bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-014i-0890000000-f76d6fb28854a5d7b6cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0fk9-0920000000-c2bd0b76c5aed757e904Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0090000000-cecd035cc60695427f78Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0gb9-0290000000-2e17076c991ea61ced1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0uk9-0970000000-59c3b8004baa44f8d3a5Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0190000000-cc04ec8c7265ba3a7297Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0udi-0970000000-82c4c7eefd54ad509f69Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00xs-0900000000-991b5b7dc028219e593bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0970000000-dc6cd01d5d2e5eeaae30Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0970000000-ee8aa480dca6e72a74fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0890000000-f76d6fb28854a5d7b6cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-1590000000-f70cf2b0756e8c80c17bSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0fk9-0920000000-c2bd0b76c5aed757e904Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0gi0-1960000000-82bc07f73bc5b2044642Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-014i-0690000000-770dc5d0db7e86d8ba07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-4767833559e7bd183ce0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-c471bf567e8a63e00e51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bi-0930000000-72a72a3eb013e045bdb0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0290000000-c9557f276875a3bf1d2bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0390000000-ff927b8db6ef70ef822dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-0910000000-d2e511be224be1b3530eSpectrum
MSMass Spectrum (Electron Ionization)splash10-014i-9670000000-3e0fa2e9c81c3bc1d936Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00553 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00553 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00553
Phenol Explorer Compound ID719
FooDB IDFDB012474
KNApSAcK IDC00000576
Chemspider ID3971
KEGG Compound IDC01864
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethoxsalen
METLIN IDNot Available
PubChem Compound4114
PDB ID8MO
ChEBI ID18358
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular weight:
58164.815
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Possesses phenacetin O-deethylation activity.
Gene Name:
CYP2A13
Uniprot ID:
Q16696
Molecular weight:
56687.095
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]