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Validamycin
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Name

Validamycin

 EINECS 609-372-4
CAS No. 37248-47-8 Density 1.69 g/cm3
PSA 253.02000 LogP -6.36180
Solubility soluble in water, methanol, dioxane, dimethylformamide Melting Point 130-135 °C
Formula C20H35NO13 Boiling Point 813.7 °C at 760 mmHg
Molecular Weight 497.497 Flash Point 445.9 °C
Transport Information N/A Appearance white powder
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 37248-47-8 (Validamycin) Hazard Symbols N/A
Synonyms

(1S-(1a,4a,5B,6a))-1,5,6-Trideoxy-3-O-B-D-glucopyranosyl-5-;HSDB 6745;Validacin;Validamycin A;Valimon;

Article Data 6

Validamycin Synthetic route

86733-63-3

7,2'',3'',4'',6''-penta-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidamycin A

37248-47-8

validamycin A

Conditions
ConditionsYield
With ammonia; sodium In tetrahydrofuran at -78℃; for 6h;
With ammonium chloride; sodium 1) liq NH3, THF, -70 deg C, 4 h 20 min, 2) room temp., 4.5 h; Multistep reaction;
86733-64-4, 121468-80-2

validamycin A undeca-O-acetate

37248-47-8

validamycin A

Conditions
ConditionsYield
With sodium methylate In methanol for 5h; Ambient temperature;
73482-11-8

validamycin A undecabenzyl ether

37248-47-8

validamycin A

Conditions
ConditionsYield
With ammonium chloride; sodium 1) liq NH3, THF, -70 deg C, 4 h 20 min, 2) room temp., 4.5 h; Multistep reaction;
2280-44-6

D-Glucose

culture medium

culture medium

A

32780-32-8

validamine

B

38231-86-6

valienamine

C

39318-73-5, 81691-72-7, 81739-22-2

validoxylamine A

D

37248-47-8

validamycin A

Conditions
ConditionsYield
With Streptomyces hygroscopicus var. limoneus In water at 28℃; for 168h; Further byproducts.;
...Expand
2280-44-6

D-Glucose

culture medium

culture medium

A

32780-32-8

validamine

B

38231-86-6

valienamine

C

37248-47-8

validamycin A

D

validamycin B

Conditions
ConditionsYield
With Streptomyces hygroscopicus var. limoneus In water at 28℃; for 168h; Further byproducts.;
...Expand
86733-61-1

2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine A

37248-47-8

validamycin A

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 55.7 percent / imidazole / CHCl3 / 40 h / Heating
2: 74.2 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 4.5 h / Ambient temperature
3: 1) sodium, 2) ammonium chloride / 1) liq NH3, THF, -70 deg C, 4 h 20 min, 2) room temp., 4.5 h
View Scheme
Multi-step reaction with 3 steps
1: 61 percent / imidazole / CHCl3 / 48 h / Heating
2: 84 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 10 h / Ambient temperature
3: liquid ammonia, sodium / tetrahydrofuran / 6 h / -78 °C
View Scheme
86733-62-2

7-O-acetyl-2,3,4',5',6',7'-hexa-O-benzylvalidoxylamine A

37248-47-8

validamycin A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 74.2 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 4.5 h / Ambient temperature
2: 1) sodium, 2) ammonium chloride / 1) liq NH3, THF, -70 deg C, 4 h 20 min, 2) room temp., 4.5 h
View Scheme
Multi-step reaction with 2 steps
1: 84 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 10 h / Ambient temperature
2: liquid ammonia, sodium / tetrahydrofuran / 6 h / -78 °C
View Scheme
86756-42-5, 102131-10-2

2,3,4',5',6',7'-hexa-O-benzyl-4,7-O-benzylidenevalidoxylamine A

37248-47-8

validamycin A

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 59 percent / aq acetic acid (80percent) / 20 h / 60 °C
2: 55.7 percent / imidazole / CHCl3 / 40 h / Heating
3: 74.2 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 4.5 h / Ambient temperature
4: 1) sodium, 2) ammonium chloride / 1) liq NH3, THF, -70 deg C, 4 h 20 min, 2) room temp., 4.5 h
View Scheme
Multi-step reaction with 4 steps
1: 86 percent / aq. 80percent acetic acid / 9 h / 50 °C
2: 61 percent / imidazole / CHCl3 / 48 h / Heating
3: 84 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 10 h / Ambient temperature
4: liquid ammonia, sodium / tetrahydrofuran / 6 h / -78 °C
View Scheme
86733-60-0, 102131-09-9

4,7-O-benzylidenevalidoxylamine A hexa-O-acetate

37248-47-8

validamycin A

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1)methanolic sodium methoxyde (1M), 2) sodium hydride / 1) methanol, room temp., 50 min, 2) DMF, room temp., 23 h
2: 59 percent / aq acetic acid (80percent) / 20 h / 60 °C
3: 55.7 percent / imidazole / CHCl3 / 40 h / Heating
4: 74.2 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 4.5 h / Ambient temperature
5: 1) sodium, 2) ammonium chloride / 1) liq NH3, THF, -70 deg C, 4 h 20 min, 2) room temp., 4.5 h
View Scheme
114779-32-7

1D-(1,3,6/2)-6-amino-4-benzyloxymethyl-1,2,3-tri-O-benzyltrihydroxycyclohex-4-ene

37248-47-8

validamycin A

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 75 percent / propan-2-ol / 110 h / 120 °C
2: 89 percent / sodium hydride, di-imidazolyl sulphone / dimethylformamide / 1.5 h / 50 °C
3: 91 percent / propan-2-ol / 4 h / 80 °C
4: 75 percent / H2 / Ranei nickel T-4 / dioxane; ethanol / 6 h / 60 °C
5: 86 percent / aq. 80percent acetic acid / 9 h / 50 °C
6: 61 percent / imidazole / CHCl3 / 48 h / Heating
7: 84 percent / silver trifluoromethanesulphonate, 1,1,3,3-tetramethylurea / CH2Cl2 / 10 h / Ambient temperature
8: liquid ammonia, sodium / tetrahydrofuran / 6 h / -78 °C
View Scheme

Validamycin Specification

The Validamycin with CAS registry number of 37248-47-8 is also known as D-Chiro-Inositol,1,5,6-trideoxy-4-O-b-D-glucopyranosyl-5-(hydroxymethyl)-1-[[4,5,6-trihydroxy-3-(hydroxymethyl)-2-cyclohexen-1-yl]amino]-,[1S-(1a,4a,5b,6a)]-. The IUPAC name is (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. It belongs to product categories of Fungicide. In addition, the formula is C20H35NO13 and the molecular weight is 497.49. This chemcial is a white powder and should be stored at the temperature of 0-6 °C. It is extracted and  made from variant and ferment of water streptomycin.

Physical properties about Validamycin are: (1)# of Rule of 5 Violations: 2; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 14; (7)#H bond donors: 12; (8)#Freely Rotating Bonds: 18; (9)Index of Refraction: 1.689; (10)Molar Refractivity: 111.91 cm3; (11)Molar Volume: 292.9 cm3; (12)Surface Tension: 112.4 dyne/cm; (13)Density: 1.69 g/cm3; (14)Flash Point: 445.9 °C; (15)Enthalpy of Vaporization: 134.65 kJ/mol; (16)Boiling Point: 813.7 °C at 760 mmHg; (17)Vapour Pressure: 1.17E-30 mmHg at 25 °C.

Uses of Validamycin: it is used as microbial fungicide. Besides, it is mainly for control of rice sheath blight, both protection and treatment. This chemical is also used to rid pellet sclerotinia, corn leaf blight, damping-off and root rot of vegetables, blight of cotton, bean, ginseng and so on.

You can still convert the following datas into molecular structure:
1. SMILES: OC/C3=C/[C@H](N[C@H]2C[C@H](CO)[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]3O
2. InChI: InChI=1/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
3. InChIKey: JARYYMUOCXVXNK-IMTORBKUBD
4. Std. InChI: 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
5. Std. InChIKey: JARYYMUOCXVXNK-IMTORBKUSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 13gm/kg (13000mg/kg)   Japan Pesticide Information. Vol. (47), Pg. 17, 1985.
mouse LD50 intravenous > 13gm/kg (13000mg/kg)   Japan Pesticide Information. Vol. (15), Pg. 28, 1973.
mouse LD50 oral 2gm/kg (2000mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 1, Pg. 229, 1980.
mouse LD50 subcutaneous > 15gm/kg (15000mg/kg)   Japan Pesticide Information. Vol. (47), Pg. 17, 1985.
rat LC50 inhalation > 5gm/m3 (5000mg/m3)   Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 17, Pg. S29, 1992.
rat LD50 intraperitoneal 10gm/kg (10000mg/kg)   Japan Pesticide Information. Vol. (47), Pg. 17, 1985.
rat LD50 intravenous 7200mg/kg (7200mg/kg)   Japan Pesticide Information. Vol. (47), Pg. 17, 1985.
rat LD50 oral > 20gm/kg (20000mg/kg)   Japan Pesticide Information. Vol. (15), Pg. 28, 1973.
rat LD50 skin > 5gm/kg (5000mg/kg)   Japan Pesticide Information. Vol. (40), Pg. 32, 1982.
rat LD50 subcutaneous > 15gm/kg (15000mg/kg)   Japan Pesticide Information. Vol. (47), Pg. 17, 1985.

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