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    Cycasin Acetate

    REF. STANDARDS & IMPURITIES

    PharmaCompass
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    2D Structure
    Also known as: Methylazoxymethanol acetate, 592-62-1, Methylazoxy methanol acetate, Dtxsid1025568, Akos006282597
    Molecular Formula
    C4H8N2O3
    Molecular Weight
    132.12  g/mol
    InChI Key
    BELPJCDYWUCHKF-AATRIKPKSA-N
    The aglycone of CYCASIN. It acts as a potent carcinogen and neurotoxin and inhibits hepatic DNA, RNA, and protein synthesis.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (E)-acetyloxymethylimino-methyl-oxidoazanium
    2.1.2 InChI
    InChI=1S/C4H8N2O3/c1-4(7)9-3-5-6(2)8/h3H2,1-2H3/b6-5+
    2.1.3 InChI Key
    BELPJCDYWUCHKF-AATRIKPKSA-N
    2.1.4 Canonical SMILES
    CC(=O)OCN=[N+](C)[O-]
    2.1.5 Isomeric SMILES
    CC(=O)OC/N=[N+](\C)/[O-]
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. (methyl-onn-azoxy)methanol Acetate

    2. Acetate, Methylazoxymethanol

    3. Methylazoxymethanol Acetate

    2.2.2 Depositor-Supplied Synonyms

    1. Methylazoxymethanol Acetate

    2. 592-62-1

    3. Methylazoxy Methanol Acetate

    4. Dtxsid1025568

    5. Akos006282597

    2.3 Create Date
    2005-09-12
    3 Chemical and Physical Properties
    Molecular Weight 132.12 g/mol
    Molecular Formula C4H8N2O3
    XLogP3-0.3
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count3
    Exact Mass132.05349212 g/mol
    Monoisotopic Mass132.05349212 g/mol
    Topological Polar Surface Area67.4 Ų
    Heavy Atom Count9
    Formal Charge0
    Complexity132
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 MeSH Pharmacological Classification

    Neurotoxins

    Toxic substances from microorganisms, plants or animals that interfere with the functions of the nervous system. Most venoms contain neurotoxic substances. Myotoxins are included in this concept. (See all compounds classified as Neurotoxins.)

    Nucleic Acid Synthesis Inhibitors

    Compounds that inhibit cell production of DNA or RNA. (See all compounds classified as Nucleic Acid Synthesis Inhibitors.)

    Protein Synthesis Inhibitors

    Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

    4.2 Absorption, Distribution and Excretion

    IN RATS INJECTED WITH (3)H-METHYLAZOXYMETHANOL ACETATE ON DAY 14 OF PREGNANCY, 4% OF INJECTED RADIOACTIVITY WAS FOUND IN FETUSES; RADIOACTIVITY WAS ALSO FOUND IN LIVER & KIDNEY OF TREATED MOTHERS. DNA & RNA FROM FETAL BRAIN CONTAINED GUANINE METHYLATED IN 7-POSITION.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V10 133 (1976)