Validamycin A is a fungicide and agricultural antibiotic originally extracted from Streptomyces hygroscopicus var. limoneus. Validamycin A can suppress the growth of Aspergillus flavus, and its MIC is 1 μg/mL. Validamycin A has high inhibitory effect against alginase (trehalase) of Rhizoctonia solani, with IC50 of 72 μM. Validamycin A is a reversible tyrosinase inhibitor (antagonist) with a Ki of 5.893 mM.

Physicochemical Properties

Molecular Formula	C20H35NO13
Molecular Weight	497.49
Exact Mass	497.21
CAS #	37248-47-8
PubChem CID	443629
Appearance	White to off-white solid powder
Density	1.7±0.1 g/cm3
Boiling Point	813.7±65.0 °C at 760 mmHg
Melting Point	130-135ºC
Flash Point	445.9±34.3 °C
Vapour Pressure	0.0±6.6 mmHg at 25°C
Index of Refraction	1.689
LogP	-5.43
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	14
Rotatable Bond Count	7
Heavy Atom Count	34
Complexity	697
Defined Atom Stereocenter Count	14
SMILES	C1[C@@H]([C@H]([C@@H]([C@H]([C@H]1N[C@H]2C=C([C@H]([C@@H]([C@H]2O)O)O)CO)O)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)CO
InChi Key	JARYYMUOCXVXNK-CSLFJTBJSA-N
InChi Code	InChI=1S/C20H35NO13/c22-3-6-1-8(12(26)15(29)11(6)25)21-9-2-7(4-23)19(17(31)13(9)27)34-20-18(32)16(30)14(28)10(5-24)33-20/h1,7-32H,2-5H2/t7-,8+,9+,10-,11-,12+,13+,14-,15+,16+,17-,18-,19-,20+/m1/s1
Chemical Name	(2R,3R,4S,5S,6R)-2-[(1R,2R,3S,4S,6R)-2,3-dihydroxy-6-(hydroxymethyl)-4-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-en-1-yl]amino]cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Targets	Antibiotic[1], IC50: 72 μM (trehalase)[2], Ki: 5.893 mM (tyrosinase)[3]
ln Vitro	Validamycin A (0.5–1 μg/mL; 18 hours) stops A from growing. conidial germination and inhibits flavus [1]. For human bronchial epithelial cells, validamycin A is not cytotoxic [1]. HIS85, HIS244, GLU256, HIS259, and ASN260 are among the residues in the tyrosinase active site that Validamycin A directly binds to [1].
Cell Assay	Cell Proliferation Assay[1] Cell Types: Aspergillus flavus ATCC204304 Tested Concentrations: 0.5 μg/mL, 1 μg/mL Incubation Duration: 18 hrs (hours) Experimental Results: Inhibited the growth of Aspergillus flavus.
ADME/Pharmacokinetics	Metabolism / Metabolites In animals, cleavage to glucose and an amine residue. Biological Half-Life Less than or equal to 5 hr
Toxicity/Toxicokinetics	Toxicity Data LC50 (rat) > 5,000 mg/m3 Non-Human Toxicity Values LD50 Rat oral > 20,000 mg/kg LD50 Mice oral > 20,000 mg/kg LD50 Rat percutaneous > 5000 mg/kg
References	[1]. The Inhibitory Effect of Validamycin A on Aspergillus flavus. Int J Microbiol. 2020; 2020: 3972415. [2]. Effect of validamycins on glycohydrolases of Rhizoctonia solani. J Antibiot (Tokyo). 1987 Apr;40(4):526-32. [3]. The effect of validamycin A on tyrosinase: inhibition kinetics and computational simulation. Int J Biol Macromol. 2013 Apr;55:15-23.
Additional Infomation	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 has been reported in Streptomyces anthocyanicus, Streptomyces hygroscopicus, and Streptomyces lividans with data available.

Solubility Data

Solubility (In Vitro)	H2O : 125 mg/mL (251.26 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 100 mg/mL (201.01 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	2.0101 mL	10.0505 mL	20.1009 mL
	5 mM	0.4020 mL	2.0101 mL	4.0202 mL
	10 mM	0.2010 mL	1.0050 mL	2.0101 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.