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Validamycin A

CAT: 0926-AV59477-01Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0926-AV59477-01Size:100 mg
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CAS Number
37248-47-8
MDL Number
MFCD09028089
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
Molecular Formula
C20H35NO13
Molecular Weight
497.49 g/mol
Controlled
No

Chemical Information

Validamycin A

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 polyol, a secondary amino compound, a member of validamycins and an antibiotic fungicide. It is a conjugate base of a validamycin A(1+).

CAS Number37248-47-8
PubChem CID443629
IUPAC 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
Molecular FormulaC20H35NO13
Molecular Weight497.5
XLogP-6.3
Topological Polar Surface Area253
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count14
Rotatable Bond Count7
Heavy Atom Count34
Formal Charge0
Complexity697
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
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
InChIKey
JARYYMUOCXVXNK-CSLFJTBJSA-N
Chemical Structure
2D Structure
2D structure of Validamycin A
CAS: 37248-47-8
CID: 443629
Formula: C20H35NO13
MW: 497.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight497.5
XLogP3-6.3
Hydrogen Bond Donor Count12
Hydrogen Bond Acceptor Count14
Rotatable Bond Count7
Exact Mass497.21084017
Monoisotopic Mass497.21084017
Topological Polar Surface Area253 Ų
Heavy Atom Count34
Formal Charge0
Complexity697
Isotope Atom Count0
Defined Atom Stereocenter Count14
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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