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Methanol, (methyl-ONN-azoxy)-, Acetate (ester)

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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

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 Formula	C₄H₈N₂O₃
Molecular Weight	132.12 g/mol
XLogP3	-0.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	132.05349212 g/mol
Monoisotopic Mass	132.05349212 g/mol
Topological Polar Surface Area	67.4 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	132
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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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