Bergaptol - analytical standard , CAS No.486-60-2

CAS: 486-60-2 Cat. No.: B135841 Molecular Weight: 202.16 Beilstein Registry Number: 190104 EC Number: 803-802-6

GRADE & PURITY Analytical standard

Synonyms

BSPBio_002390 | UNII-KTC8ANI30F | 5-Hydroxyfuranocoumarin | A827582 | 5-hydroxy-2H-furo[3,2-g]chromen-2-one | 7H-Furo[3,2-g][1]benzopyran-7-one, 4-hydroxy- | Psoralin, 5-hydroxy- | 7H-Furo(3,2-g)(1)benzopyran-7-one, 4-hydroxy- | Z1509594645 | NSC341958 |

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

BSPBio_002390 | UNII-KTC8ANI30F | 5-Hydroxyfuranocoumarin | A827582 | 5-hydroxy-2H-furo[3, 2-g]chromen-2-one | 7H-Furo[3, 2-g][1]benzopyran-7-one, 4-hydroxy- | Psoralin, 5-hydroxy- | 7H-Furo(3, 2-g)(1)benzopyran-7-one, 4-hydroxy- | Z1509594645 | NSC341958 |

Specifications & Purity

analytical standard

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Analytical standard

Names and Identifiers

• Canonical Smiles: C1=CC(=O)OC2=CC3=C(C=CO3)C(=C21)O
• IUPAC Name: 4-hydroxyfuro[3,2-g]chromen-7-one
• InChIKey: GIJHDGJRTUSBJR-UHFFFAOYSA-N
• INCHI: 1S/C11H6O4/c12-10-2-1-6-9(15-10)5-8-7(11(6)13)3-4-14-8/h1-5,13H
• Isomeric SMILES: C1=CC(=O)OC2=CC3=C(C=CO3)C(=C21)O
• WGK Germany: 3
• Molecular Weight: 202.16
• Beilstein: 190104
• Reaxy-Rn: 190104
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=190104&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-hydroxypsoralens

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Coumarins and derivatives
• Subclass: Furanocoumarins
• Intermediate Tree Nodes: Linear furanocoumarins - Psoralens
• Direct Parent: 5-hydroxypsoralens
• Alternative Parents: 1-benzopyrans Benzofurans Pyranones and derivatives 1-hydroxy-4-unsubstituted benzenoids Heteroaromatic compounds Furans Lactones Oxacyclic compounds Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 5-hydroxypsoralen - Benzopyran - 1-benzopyran - Benzofuran - 1-hydroxy-4-unsubstituted benzenoid - Pyranone - Pyran - Benzenoid - Furan - Heteroaromatic compound - Lactone - Oxacycle - Organoheterocyclic compound - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 5-hydroxypsoralens. These are psoralens containing a hydroxyl 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)

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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BACE1 Tchem Beta-secretase 1 (15641 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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HT-29 (80576 Activities)

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HepG2 (196354 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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L3MBTL1 Tchem Lethal(3)malignant brain tumor-like protein 1 (14536 Activities)

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ERG Tbio Transcriptional regulator ERG (5589 Activities)

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HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)

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GMNN Tbio Geminin (128009 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

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Associated Targets(non-human)

Abcb1b P-glycoprotein 1 (174 Activities)

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Mycobacterium tuberculosis (203094 Activities)

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3T3-L1 (3664 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

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FTL Ferritin light chain (43324 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 202.160 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 202.027 Da
• Monoisotopic Mass: 202.027 Da
• Topological Polar Surface Area: 59.700 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 312.000
• 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. 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]