5-Methoxypsoralen - Moligand™, ≥98%(GC) , CAS No.484-20-8

CAS: 484-20-8 Cat. No.: M101153 Molecular Weight: 216.19 Beilstein Registry Number: 19560 EC Number: 207-604-5

GRADE & PURITY Moligand™, ≥98%(GC)

Synonyms

4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-one | Oprea1_562364 | Spectrum3_000663 | MFCD00010272 | NCGC00017357-01 | HSDB 3466 | KBio2_001274 | 5-methoxypsoralene | BERGAPTEN [MI] | Psoraderm | 4FVK84C92X | 5 methoxypsoralen | Bergapten | NSC755877 | NSC-755

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

4-Methoxy-7H-furo(3, 2-g)(1)benzopyran-7-one | Oprea1_562364 | Spectrum3_000663 | MFCD00010272 | NCGC00017357-01 | HSDB 3466 | KBio2_001274 | 5-methoxypsoralene | BERGAPTEN [MI] | Psoraderm | 4FVK84C92X | 5 methoxypsoralen | Bergapten | NSC755877 | NSC-755

Specifications & Purity

Moligand™, ≥98%(GC)

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Purity

≥98%(GC)

Names and Identifiers

• Pubchem Sid: 488179695
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488179695
• Canonical Smiles: COC1=C2C=CC(=O)OC2=CC3=C1C=CO3
• IUPAC Name: 4-methoxyfuro[3,2-g]chromen-7-one
• InChIKey: BGEBZHIAGXMEMV-UHFFFAOYSA-N
• INCHI: 1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
• Isomeric SMILES: COC1=C2C=CC(=O)OC2=CC3=C1C=CO3
• WGK Germany: 2
• RTECS: LV1300000
• Alternate CAS: 484-20-8
• NSC Number: 95437
• UN Number: 1759
• Packing Group: I
• MeSH Entry Terms: 5 Methoxy Psoralen;5 Methoxypsoralen;5-Methoxy Psoralen;5-methoxypsoralen;bergapten;Pentaderm
• Molecular Weight: 216.19
• Beilstein: 19560
• Reaxy-Rn: 19560
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=19560&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Coumarins and derivatives
      • Subclass Furanocoumarins
        • Level5 Linear furanocoumarins
          • Level6 Psoralens
            • Level7 5-methoxypsoralens

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Furanocoumarins
• Intermediate Tree Nodes: Linear furanocoumarins - Psoralens
• Direct Parent: 5-methoxypsoralens
• Alternative Parents: 1-benzopyrans Benzofurans Anisoles Pyranones and derivatives Alkyl aryl ethers Heteroaromatic compounds Furans Lactones Oxacyclic compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 5-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
• Description: This compound belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.
• External Descriptors: a coumarin

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP1A2 Tchem Cytochrome P450 1A2 (2 Activities)

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CYP1A1 Tchem Cytochrome P450 1A1 (2 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

F2 Tclin Thrombin (11687 Activities)

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ESR1 Tclin Estrogen receptor alpha (17718 Activities)

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PGR Tclin Progesterone receptor (8562 Activities)

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CHRM2 Tclin Muscarinic acetylcholine receptor M2 (10671 Activities)

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HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)

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ADRA2A Tclin Alpha-2a adrenergic receptor (9450 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

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TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

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MAOA Tclin Monoamine oxidase A (11911 Activities)

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DRD1 Tclin Dopamine D1 receptor (9720 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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PTGS1 Tclin Cyclooxygenase-1 (9233 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

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SLC6A4 Tclin Serotonin transporter (12625 Activities)

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ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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OPRM1 Tclin Mu opioid receptor (19785 Activities)

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DRD3 Tclin Dopamine D3 receptor (14368 Activities)

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SLC6A3 Tclin Dopamine transporter (10535 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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PDE3A Tclin Phosphodiesterase 3A (3309 Activities)

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HTR2B Tclin Serotonin 2b (5-HT2b) receptor (10323 Activities)

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TBXA2R Tclin Thromboxane A2 receptor (5717 Activities)

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PDE4A Tclin Phosphodiesterase 4A (1943 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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CYP1B1 Tchem Cytochrome P450 1B1 (1148 Activities)

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KCNA5 Tclin Voltage-gated potassium channel subunit Kv1.5 (1353 Activities)

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HRH3 Tclin Histamine H3 receptor (10389 Activities)

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KCNA2 Tclin Voltage-gated potassium channel subunit Kv1.2 (28 Activities)

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KCNA3 Tclin Voltage-gated potassium channel subunit Kv1.3 (1067 Activities)

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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)

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CYP1A1 Tchem Cytochrome P450 1A1 (1169 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

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BACE1 Tchem Beta-secretase 1 (15641 Activities)

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KCNA1 Tclin Voltage-gated potassium channel subunit Kv1.1 (248 Activities)

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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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CYP2A6 Tchem Cytochrome P450 2A6 (2861 Activities)

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CYP2B6 Tchem Cytochrome P450 2B6 (1338 Activities)

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A498 (42825 Activities)

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ACHN (49357 Activities)

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CAKI-1 (44928 Activities)

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CCRF-CEM (65223 Activities)

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COLO 205 (50209 Activities)

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DU-145 (51482 Activities)

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HL-60 (67320 Activities)

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HT-1080 (3966 Activities)

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Associated Targets(non-human)

Abcb1b P-glycoprotein 1 (174 Activities)

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Hdac6 Histone deacetylase 6 (222 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

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Artemia salina (1320 Activities)

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Fusarium solani (1274 Activities)

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Salmonella typhimurium (15756 Activities)

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Cavia porcellus (23802 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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Human immunodeficiency virus (3636 Activities)

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lef Anthrax lethal factor (7585 Activities)

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Lactuca sativa (1092 Activities)

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Dyrk1a Dual specificity tyrosine-phosphorylation-regulated kinase 1A (1629 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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BCHE Cholinesterase (8742 Activities)

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Allium cepa (293 Activities)

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Colletotrichum gloeosporioides (560 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Agrostis stolonifera (91 Activities)

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PA Polymerase acidic protein (806 Activities)

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Slco1a5 Solute carrier organic anion transporter family member 1A5 (48 Activities)

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Bactrocera oleae (43 Activities)

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Colletotrichum acutatum (300 Activities)

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Diaporthe ampelina (88 Activities)

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Phomopsis obscurans (86 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility in water: Practically insoluble; Soluble in Ether; Slightly soluble in Alcohol,Chloroform,Benzene
• Sensitivity: Light Sensitive
• Melt Point(°C): 190-193°C
• Molecular Weight: 216.190 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 216.042 Da
• Monoisotopic Mass: 216.042 Da
• Topological Polar Surface Area: 48.700 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 325.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Liangliang Han, Libo Zhang, Yuedong He, Lijing Liao, Junde Li, Sheng Xu, Yucheng Zhao, Xiaohong Bian, Yuanzheng Xia.  (2023)  Three carbon-/oxygen-prenyltransferases responsible for furanocoumarin synthesis in Angelica dahurica.  INDUSTRIAL CROPS AND PRODUCTS,      [PMID:] [10.1016/j.indcrop.2023.116814]

2. Congyi Zhu, Cheng Peng, Diyang Qiu, Jiwu Zeng.  (2022)  Metabolic Profiling and Transcriptional Analysis of Carotenoid Accumulation in a Red-Fleshed Mutant of Pummelo (Citrus grandis).  MOLECULES,  27  (14): (4595).  [PMID:35889470] [10.3390/molecules27144595]

3. Sun Yujing, Wang Yihua, Zhang Le, Ye Xingqian, Guo Jingtong.  (2024)  Furanocoumarin profiles and inhibitory effects on cytochrome P450 activity of whole citrus fruit.  Food Quality and Safety,      [PMID:] [10.1093/fqsafe/fyae038]

4. Hao-Nan Ding, Xu-Wen Wang, Yu-Xin Qian, Ke Liu, Lei Jin.  (2025)  Effects of bergapten-loaded long-circulating liposomes on osteogenic differentiation of human dental pulp stem cells.  JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH,      [PMID:41160646] [10.1080/10286020.2025.2575989]

5. Kong Chao-Ying, Luo Chu-Wen, Xu Ya-Jun, Shen Na, Tang Zhao-Hui.  (2025)  Ultrasound-induced Activation of Tetravalent Platinum Polyglutamate Nanoprodrug Accelerated by Coumarin Derivatives.  CHINESE JOURNAL OF POLYMER SCIENCE,      [PMID:] [10.1007/s10118-025-3469-5]