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Chemistry

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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

Cycasin Acetate
The aglycone of CYCASIN. It acts as a potent carcinogen and neurotoxin and inhibits hepatic DNA, RNA, and protein synthesis.
1 2D Structure

Cycasin Acetate

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)


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