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Validamycin A

Validamycin A structure

CAS No:
37248-47-8
Formula:
C20H35NO13
Chemical Name:
Validamycin A
Synonyms:
D-chiro-Inositol,1,5,6-trideoxy-4-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-;D-chiro-Inositol,1,5,6-trideoxy-4-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-[[4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-,[1S-(1α,4α,5β,6α)]-;1,5,6-Trideoxy-4-O-β-D-glucopyranosyl-5-(hydroxymethyl)-1-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-D-chiro-inositol;Validamycin A;Validacin;Cepex 10SL;Jinggangmycin A;Jinggangmycin;Validamycin;Jinggang;Jinganmycin A;58194-43-7;75661-94-8
Categories:
Agrochemicals > Biopesticides

Description

ChEBI: A member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its beta-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cycloh x-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus.

Validamycin A is a member of the class of validamycins that is (1R,2S,3S,4S,6R)-4-amino-6-(hydroxymethyl)cyclohexane-1,2,3-triol in which the hydroxy group at position 1 has been converted to its beta-D-glucoside and in which one of the hydrogens attached to the nitrogen is replaced by a (1R,4R,5R,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl group. It is the major validamycin produced by Streptomyces hygroscopicus. It has a role as an EC 2.4.1.231 [alpha,alpha-trehalose phosphorylase (configuration-retaining)] inhibitor, an EC 2.4.1.64 (alpha,alpha-trehalose phosphorylase) inhibitor, an EC 3.2.1.28 (alpha,alpha-trehalase) inhibitor and an antifungal agrochemical. It is a member of validamycins, a secondary amino compound, a polyol and an antibiotic fungicide. It is a conjugate base of a validamycin A(1+).

Validamycin A Basic Attributes

Molecular Weight：

497.49100

Exact Mass：

497.49

EC Number：

609-372-4

UNII：

313E9620QS

DSSTox ID：

DTXSID4058073

Color/Form：

Colorless powder|White powder

Characteristics

PSA：

253.02000

XLogP3：

-6.36180

Appearance：

white powder

Density：

1.69g/cm3

Melting Point：

130-135 °C (decomp)

Boiling Point：

813.7ºC at 760mmHg

Flash Point：

445.9ºC

Refractive Index：

1.689

Water Solubility：

Readily soluble

Storage Conditions：

0-6ºC

Vapor Pressure：

Neglible at room temperature

Odor：

Odorless

Experimental Properties：

Stable at room temperature, in neutral and alkaline solution, but slightly unstable under acidic conditions.|Decomposes over a wide temp range about 130 °C.|Hygroscopic|Compatible with most common pesticides.

Corrosivity：

Non-corrosive to metals

Safety Information

Stability/Shelf Life：

Stable at room temperature and in neutral or alkaline media, slightly unstable in acidic media.

Personal Protective Equipment：

No special clothing required.

Toxicity

Non-Human Toxicity Values：

LD50 Rat oral > 20,000 mg/kg|LD50 Mice oral > 20,000 mg/kg|LD50 Rat percutaneous > 5000 mg/kg

Drug Information

Metabolism/Metabolites：

In animals, cleavage to glucose and an amine residue.

Biological Half-Life：

Less than or equal to 5 hr

Antidote：

No specific antidote known. Symptomatic treatment.

MeSH Entry Terms：

jinggangmycin

Validamycin A Use and Manufacturing

Methods of Manufacturing

Produced by Streptomyces variable limoneus.

Uses

Validamycin A is the major analogue of a family of cyclitol disaccharides isolated from Streptomyces hygroscopicus var. limoneus by researchers at Takeda in 1970. Although commonly regarded as an aminoglycoside, validamycin shares little in common with conventional aminoglycosides such as streptomycin and gentamicin. Validamycin A is a potent antifungal agent and is used to control fungi in crop production. Validamycin A acts as a potent inhibitor of trehalase, an important enzyme in carbohydrate storage and ultilisation in fungi.

Formulations：

Soluble concentrate (30 g ai/l); dustable powder (3 g/kg).|3%, 5% liquid, 0.3% dust|Solution; dustable powder; seed treatment

Analytic Methods：

Product and residue analysis is by gas liquid chromatography of a derivative with flame ionization detector.

Use Classification：

Agrochemicals -> Fungicides

Computed Properties

Molecular Weight:497.5
XLogP3:-6.3
Hydrogen Bond Donor Count:12
Hydrogen Bond Acceptor Count:14
Rotatable Bond Count:7
Exact Mass:497.21084017
Monoisotopic Mass:497.21084017
Topological Polar Surface Area:253
Heavy Atom Count:34
Complexity:697
Defined Atom Stereocenter Count:14
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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