| Record Information |
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| Version | 1.0 |
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| Created at | 2012-09-11 19:04:36 UTC |
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| Updated at | 2024-05-11 00:24:50 UTC |
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| NP-MRD ID | NP0000003 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Psoralen |
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| Description | Psoralen, also known as psoralene, 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 the parent compound in a family of naturally occurring organic compounds known as the linear furanocoumarins. Psoralen is structurally related to coumarin by the addition of a fused furan ring and is considered as a derivative of umbelliferone. Biosynthetically, psoralen originates from coumarins in the shikimate pathway. Psoralen is produced exclusively by plants but can be found in animals that consume these plants. Psoralen can be found in several plant sources with Ficus carica (the common fig) being probably the most abundant source of psoralens. They are also found in small quantities in Ammi visnaga (bisnaga), Pastinaca sativa (parsnip), Petroselinum crispum (parsley), Levisticum officinale (lovage), Foeniculum vulgare (fruit, i.E., Fennel seeds), Daucus carota (carrot), Psoralea corylifolia (babchi), Apium graveolens (celery), and bergamot oil (bergapten, bergamottin). Psoralen is found in all citrus fruits. Psoralen is a well-known mutagen and is used for this purpose in molecular biology research. Psoralen intercalates into DNA and on exposure to ultraviolet (UVA) radiation can form monoadducts and covalent inter-strand cross-links (ICL) with thymines in the DNA molecule. Psoralen also functions as a drug. An important use of psoralen is in the treatment for skin problems such as psoriasis and, to a lesser extent, eczema and vitiligo. This treatment takes advantage of the high UV absorbance of psoralen. In treating these skin conditions psoralen is applied first to sensitise the skin, then UVA light is applied to clean up the skin problem. Psoralen has also been recommended for treating alopecia. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 3-(6-Hydroxy-5-benzofuranyl)-2-propenoic acid delta-lactone | ChEBI | | 6,7-Furanocoumarin | ChEBI | | 6-Hydroxy-5-benzofuranacrylic acid delta-lactone | ChEBI | | 7H-Furo[3,2-g][1]benzopyran-7-one | ChEBI | | Ficusin | ChEBI | | Furo[2',3':7,6]coumarin | ChEBI | | Furo[4',5':6,7]coumarin | ChEBI | | Furocoumarin | ChEBI | | Manaderm | ChEBI | | Psoralene | ChEBI | | 7H-Furo[3,2-g]chromen-7-one | Kegg | | 3-(6-Hydroxy-5-benzofuranyl)-2-propenoate delta-lactone | Generator | | 3-(6-Hydroxy-5-benzofuranyl)-2-propenoate δ-lactone | Generator | | 3-(6-Hydroxy-5-benzofuranyl)-2-propenoic acid δ-lactone | Generator | | 6-Hydroxy-5-benzofuranacrylate delta-lactone | Generator | | 6-Hydroxy-5-benzofuranacrylate δ-lactone | Generator | | 6-Hydroxy-5-benzofuranacrylic acid δ-lactone | Generator | | 2H-Furo[3,2-g]chromen-2-one | HMDB | | 5-Benzofuranacrylic acid, 6-hydroxy-, delta-lactone | HMDB | | 6-Hydroxy-5-benzofuranacrylic acid beta-lactone | HMDB | | 6-Hydroxy-5-benzofuranacrylic acid gamma-lactone | HMDB | | 7H-Furo(3,2-g)(1)benzopyran-7-one | HMDB | | 7H-Furo[3,2-g]benzopyran-7-one | HMDB | | 7H-Furo[3,2-g][1]benzopyran-7-one, 9ci | HMDB | | Furo(2',3',7,6)coumarin | HMDB | | Furo(3,2-g)-coumarin | HMDB | | Furo(4',5',6,7)coumarin | HMDB | | Furo[2'.3':7.6]coumarin | HMDB | | Furo[3,2-g]coumarin | HMDB | | Phytoalexin | HMDB | | Phytoalexin-CMPD | HMDB | | Psorline-p | HMDB |
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| Chemical Formula | C11H6O3 |
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| Average Mass | 186.1660 Da |
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| Monoisotopic Mass | 186.03169 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | 66-97-7 |
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| SMILES | Not Available |
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| InChI Identifier | InChI=1S/C11H6O3/c12-11-2-1-7-5-8-3-4-13-9(8)6-10(7)14-11/h1-6H |
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| InChI Key | ZCCUUQDIBDJBTK-UHFFFAOYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 151 MHz, CDCl3, experimental) | wuhonghua2011@tjutcm.edu.cn | Tianjin University of Traditional Chinese Medicine | Hong-Hua Wu | 2024-05-09 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental) | wuhonghua2011@tjutcm.edu.cn | Tianjin University of Traditional Chinese Medicine | Hong-Hua Wu | 2024-05-09 | View Spectrum |
| | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 1H NMR Spectrum (1D, 600, CDCl3, simulated) | wuhonghua2011@tjutcm.edu.cn | Tianjin University of Traditional Chinese Medicine | Hong-Hua Wu | 2024-05-09 | View Spectrum |
| | Species |
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| Species of Origin | |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Coumarins and derivatives |
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| Sub Class | Furanocoumarins |
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| Direct Parent | Psoralens |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 113 - 115 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.51 g/L | Not Available | | LogP | 4.02 | Not Available |
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| Predicted Properties | Not Available |
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| General References | - Rodighiero P, Guiotto A, Pastorini G, Manzini P, Bordin F, Baccichetti F, Carlassare F, Vedaldi D, Dall'Acqua F: Photochemical and photobiological properties of 4,5'-dimethylpsoralen, a bifunctional contaminant of synthetic 4,5'-dimethylangelicin. Farmaco Sci. 1981 Jul;36(7):648-62. [PubMed:7274446 ]
- Insawang M, Wongpraparut C: Recalcitrant solar urticaria induced by UVA and visible light: a case report. J Med Assoc Thai. 2010 Oct;93(10):1238-41. [PubMed:20973330 ]
- Noedl H, Krudsood S, Chalermratana K, Silachamroon U, Leowattana W, Tangpukdee N, Looareesuwan S, Miller RS, Fukuda M, Jongsakul K, Sriwichai S, Rowan J, Bhattacharyya H, Ohrt C, Knirsch C: Azithromycin combination therapy with artesunate or quinine for the treatment of uncomplicated Plasmodium falciparum malaria in adults: a randomized, phase 2 clinical trial in Thailand. Clin Infect Dis. 2006 Nov 15;43(10):1264-71. Epub 2006 Oct 12. [PubMed:17051490 ]
- Wong RW, Rabie AB: Effect of psoralen on bone formation. J Orthop Res. 2011 Feb;29(2):158-64. doi: 10.1002/jor.21124. [PubMed:20196083 ]
- Lee SJ, Nam KW, Mar W: Effects of psoralen from Psoralea corylifolia on quinone reductase, ornithine decarboxylase, and JB6 cells transformation promotion. Arch Pharm Res. 2011 Jan;34(1):31-6. doi: 10.1007/s12272-011-0103-6. Epub 2011 Apr 6. [PubMed:21468912 ]
- He RS, Li SW, Yang TT, Lai JX, Liu XJ, Xue BX, Zhang LH, Wu HH: Furfural Derivatives and Phenolic Constituents in Stemona tuberosa Lour. Chem Biodivers. 2023 Sep;20(9):e202300693. doi: 10.1002/cbdv.202300693. Epub 2023 Sep 6. [PubMed:37614210 ]
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