Back to Compounds

Showing Compound Psoralen (FDB012605)

Record Information
Version1.0
Creation date2010-04-08 22:10:16 UTC
Update date2019-11-26 03:07:11 UTC
Primary IDFDB012605
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePsoralen
DescriptionPsoralen, also known as ficusin or manaderm, 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. Psoralen is found, on average, in the highest concentration within a few different foods, such as figs (Ficus carica), parsleys (Petroselinum crispum), and parsnips (Pastinaca sativa) and in a lower concentration in fennels (Foeniculum vulgare), lovages (Levisticum officinale), and wild carrots (Daucus carota). Psoralen has also been detected, but not quantified in, several different foods, such as kales (Brassica napus var. pabularia), persian limes (Citrus latifolia), cereals and cereal products, japanese pumpkins (Cucurbita maxima), and climbing beans (Vigna umbellata). This could make psoralen a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Psoralen.
CAS Number66-97-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
3-(6-Hydroxy-5-benzofuranyl)-2-propenoic acid delta-lactoneChEBI
6,7-FuranocoumarinChEBI
6-Hydroxy-5-benzofuranacrylic acid delta-lactoneChEBI
7H-Furo[3,2-g][1]benzopyran-7-oneChEBI
FicusinChEBI
Furo[2',3':7,6]coumarinChEBI
Furo[4',5':6,7]coumarinChEBI
FurocoumarinChEBI
ManadermChEBI
PsoraleneChEBI
7H-Furo[3,2-g]chromen-7-oneKegg
3-(6-Hydroxy-5-benzofuranyl)-2-propenoate delta-lactoneGenerator
3-(6-Hydroxy-5-benzofuranyl)-2-propenoate δ-lactoneGenerator
3-(6-Hydroxy-5-benzofuranyl)-2-propenoic acid δ-lactoneGenerator
6-Hydroxy-5-benzofuranacrylate delta-lactoneGenerator
6-Hydroxy-5-benzofuranacrylate δ-lactoneGenerator
6-Hydroxy-5-benzofuranacrylic acid δ-lactoneGenerator
2H-furo[3,2-g]Chromen-2-oneHMDB
5-Benzofuranacrylic acid, 6-hydroxy-, delta-lactoneHMDB
6-Hydroxy-5-benzofuranacrylic acid beta-lactoneHMDB
6-Hydroxy-5-benzofuranacrylic acid gamma-lactoneHMDB
7H-furo(3,2-g)(1)Benzopyran-7-oneHMDB
7H-furo[3,2-g]Benzopyran-7-oneHMDB
7H-furo[3,2-g][1]Benzopyran-7-one, 9ciHMDB
furo(2',3',7,6)CoumarinHMDB
furo(3,2-g)-CoumarinHMDB
furo(4',5',6,7)CoumarinHMDB
furo[2'.3':7.6]CoumarinHMDB
furo[3,2-g]CoumarinHMDB
PhytoalexinHMDB
Phytoalexin-CMPDHMDB
Psorline-PHMDB
2H-Furo[3,2-g]chromen-2-onedb_source
3-(6-hydroxy-5-benzofuranyl)-2-propenoic acid delta-lactonebiospider
6-hydroxy-5-benzofuranacrylic acid delta-lactonebiospider
6-hydroxy-5-benzofuranacrylic acid gamma-lactonebiospider
7H-Furo(3,2-g)(1)benzopyran-7-onebiospider
7H-Furo[3,2-g][1]benzopyran-7-one, 9CIdb_source
7H-Furo[3,2-g]benzopyran-7-onebiospider
Furo(2',3',7,6)coumarinbiospider
Furo(3,2-g)-coumarinbiospider
Furo(4',5',6,7)coumarinbiospider
Furo[2'.3':7.6]coumarinbiospider
Furo[3,2-g]coumarinbiospider
Psorline-pbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.15ALOGPS
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
Polarizability18.1 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC11H6O3
IUPAC name7H-furo[3,2-g]chromen-7-one
InChI IdentifierInChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H
InChI KeyZCCUUQDIBDJBTK-UHFFFAOYSA-N
Isomeric SMILESO=C1OC2=CC3=C(C=CO3)C=C2C=C1
Average Molecular Weight186.166
Monoisotopic Molecular Weight186.031694053
Classification
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.97%; H 3.25%; O 25.78%DFC
Melting PointMp 171° (161-162°, 165°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP1.67(IN PRESS)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data310 (e 8000) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-052r-3900000000-eff7b2146482de5c77402014-09-20View Spectrum
GC-MSPsoralen, non-derivatized, GC-MS Spectrumsplash10-0pbi-0900000000-f4158c6b7c0ecf20d9feSpectrum
GC-MSPsoralen, non-derivatized, GC-MS Spectrumsplash10-0r2i-6900000000-276c6db470fc13777449Spectrum
GC-MSPsoralen, non-derivatized, GC-MS Spectrumsplash10-0pbi-0900000000-f4158c6b7c0ecf20d9feSpectrum
GC-MSPsoralen, non-derivatized, GC-MS Spectrumsplash10-0r2i-6900000000-276c6db470fc13777449Spectrum
Predicted GC-MSPsoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052u-1900000000-900e13490ddfba7e89efSpectrum
Predicted GC-MSPsoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPsoralen, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00lr-1900000000-ac91ad62c36a29665a712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-75211365e04f082732882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00lr-0900000000-fa9d08e8d5421ebeaa772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0f89-0900000000-bacd49139ec536fb55e72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-1900000000-ac91ad62c36a29665a712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-001r-0900000000-195d9e7e3b29cf95c3272017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-75211365e04f082732882021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00lr-0900000000-fa9d08e8d5421ebeaa772021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0f89-0900000000-bacd49139ec536fb55e72021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-287480067e742345fcb92015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-2bf4a5ffe9d6883b015e2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-1900000000-519db61c8cb6a8a315492015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-559cba64d14574cb00412015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-503a6a3d5ba551e5c0f52015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-857f114f045cf9aa2b392015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-f3f07adc83a68e9e76ff2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f3f07adc83a68e9e76ff2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0900000000-a2c2c14d0cf6b23ada922021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-89e4df10d3690e5a6d152021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-89e4df10d3690e5a6d152021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-0900000000-89e4df10d3690e5a6d152021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, experimental)Spectrum
ChemSpider ID5964
ChEMBL IDCHEMBL164660
KEGG Compound IDC09305
Pubchem Compound ID6199
Pubchem Substance IDNot Available
ChEBI ID27616
Phenol-Explorer ID718
DrugBank IDNot Available
HMDB IDHMDB34272
CRC / DFC (Dictionary of Food Compounds) IDHJG27-Y:HJG27-Y
EAFUS IDNot Available
Dr. Duke IDFICUSIN|PSORALEN
BIGG IDNot Available
KNApSAcK IDC00000297
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPsoralen
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti depressant52217 An agent that regulates mood, reducing symptoms of depression and anxiety by altering neurotransmitter levels in the brain, commonly used in managing depression, anxiety disorders, and other mood disorders.DUKE
Anti leukodermicAn agent that treats leucoderma (vitiligo), characterized by white skin patches or total loss of pigmentation, promoting skin repigmentation and reducing disease progression, commonly used in dermatology to manage vitiligo and other skin pigmentation disorders.DUKE
Anti mitoticAn agent that inhibits mitosis, or cell division, playing a crucial role in regulating cell growth. Therapeutically, it is used to treat cancer by blocking tumor cell proliferation. Key medical uses include chemotherapy for various cancers, such as breast, lung, and colon cancer, to prevent cancer cell division and growth.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti-psoriac52217 An agent that reduces psoriasis symptoms, commonly used in managing plaque psoriasis, scalp psoriasis, and other inflammatory skin conditions, by inhibiting cell growth, reducing inflammation, and modulating the immune system.DUKE
Anti-spasmodic52217 An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.DUKE
Anti-tubercular33282 An agent that combats tuberculosis, playing a biological role in inhibiting the growth of Mycobacterium tuberculosis. Therapeutically, it is used to treat and prevent tuberculosis, with key medical applications including the treatment of active TB, latent TB, and TB meningitis, as well as preventing the spread of TB in high-risk populations.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Antitumor promoter35610 An agent that inhibits tumor growth and progression, reducing cancer cell proliferation. Therapeutically, it prevents tumor development and spread, with key medical uses in cancer prevention and treatment, particularly in combating carcinogenesis and metastasis.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
ArtemicideAn herbicidal agent that targets and eliminates weeds of the Artemisia genus, with potential therapeutic applications in allergy management and anti-inflammatory uses, particularly for conditions exacerbated by Artemisia allergens.DUKE
Bacteriophagicide33282 An agent that kills bacteriophages, reducing their ability to infect bacteria. Its biological role is to regulate phage populations, and it has therapeutic applications in phage therapy, where it can be used to prevent phage-mediated bacterial lysis, and key medical uses include treating phage-borne bacterial infections.DUKE
Calcium antagonist48706 A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Contraceptive52217 An agent that prevents pregnancy by inhibiting ovulation, fertilization, or implantation, used to control birth rates, manage menstrual disorders, and reduce the risk of sexually transmitted infections, commonly applied in various forms such as pills, injections, and barrier methods.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
Fungicide24127 An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.DUKE
Genotoxic50902 An agent that damages genetic material, disrupting DNA structure and function. It has a biological role in inducing mutations and cancer. Therapeutically, genotoxic agents are used in chemotherapy to target rapidly dividing cancer cells. Key medical uses include cancer treatment, with applications in oncology for killing malignant cells and inhibiting tumor growth.DUKE
HypotensiveAn agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.DUKE
Insecticide24852 An agent that kills or repels insects, used to control pests and prevent disease transmission. Therapeutically, insecticides have applications in public health and veterinary medicine, key medical uses include controlling insect-borne diseases such as malaria, typhus, and Lyme disease.DUKE
Monoamine-oxidase-A inhibitor23924 An agent that blocks monoamine oxidase A, an enzyme breaking down neurotransmitters like serotonin and norepinephrine. Therapeutically, it increases their levels, commonly used in managing depression, anxiety disorders, and certain neurodegenerative diseases.DUKE
Monoamine-oxidase-B inhibitor23924 An agent that blocks monoamine oxidase B enzyme, reducing dopamine breakdown. Therapeutically, it increases dopamine levels, used to manage Parkinson's disease symptoms, and has neuroprotective effects, potentially slowing disease progression.DUKE
MutagenicAn agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Photocarcinogenic50903 An agent that increases the risk of skin cancer upon exposure to light, particularly UV radiation. It plays a biological role in damaging skin cells' DNA, leading to tumor formation. Therapeutically, understanding photocarcinogenic effects is crucial in developing sunscreens and protective measures. Key medical uses include warning labels on photosensitizing medications and educating patients on sun protection to prevent skin cancer.DUKE
PhototoxicAn agent that causes skin damage, such as sunburn or blisters, upon exposure to light, especially ultraviolet light, with no therapeutic applications but key medical uses in diagnosing photosensitivity disorders.DUKE
Phytoalexin26115 A plant-derived compound that plays a biological role in defense against pathogens. It has therapeutic applications as an antimicrobial, antioxidant, and anti-inflammatory agent, with key medical uses in managing infections, cancer, and neurodegenerative diseases.DUKE
Topoisomerase-II inhibitor50750 An agent that blocks the activity of topoisomerase-II, an enzyme involved in DNA replication. It prevents cancer cell growth by disrupting DNA structure, commonly used in chemotherapy to treat various types of cancer, including leukemia and lymphoma.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.