(2S)-2-[[(5R,8S)-8-[[(2S,3R)-1-(2-amino-3-hydroxypropanoyl)-3-hydroxypyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-13-methyl-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-5-carbonyl]amino]propanoic acid
Basic information
- CAS
147214-63-9- Standard SMILES
Cc1c(O)cc(O)c2c1C(=O)OC[C@H](NC(=O)[C@@H]1[C@H](O)CCN1C(=O)C(N)CO)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)O)CSC2- InChIKey
HMHQWJDFNVJCHA-ZPGBQQFCSA-N- Molecular formula
- C26H35N5O12S
- Average molar mass
- 641.6 g/mol
- Monoisotopic mass
- 641.20029256
Overview
Cyclothialidine is a peptide.
Names & identifiers
- Preferred name
- (2S)-2-[[(5R,8S)-8-[[(2S,3R)-1-(2-amino-3-hydroxypropanoyl)-3-hydroxypyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-13-methyl-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-5-carbonyl]amino]propanoic acid
- IUPAC
- (2S)-2-[[(5R,8S)-8-[[(2S,3R)-1-(2-amino-3-hydroxypropanoyl)-3-hydroxypyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-13-methyl-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-5-carbonyl]amino]propanoic acid
- English name
- cyclothialidine
- Molecular formula
- C26H35N5O12S
- Molecular weight
- 641.65
Names & synonyms
C12057(2S)-2-[[(5R,8S)-8-[[(2S,3R)-1-(2-amino-3-hydroxypropanoyl)-3-hydroxypyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-13-methyl-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-5-carbonyl]amino]propanoic acid(2S)-2-[[(5R,8S)-8-[[(2S,3R)-1-(2-amino-3-hydroxy-propanoyl)-3-hydroxy-pyrrolidine-2-carbonyl]amino]-14,16-dihydroxy-13-methyl-7,11-dioxo-10-oxa-3-thia-6-azabicyclo[10.4.0]hexadeca-1(16),12,14-triene-5-carbonyl]amino]propanoic acidAC1L9EWBCHEMBL4286501SCHEMBL29801513CHEBI:29566GTPL10988DTXSID00933066Q27110149N-[Hydroxy(6,12,14-trihydroxy-7-{[hydroxy(3-hydroxy-1-serylpyrrolidin-2-yl)methylidene]amino}-11-methyl-10-oxo-1,3,4,7,8,10-hexahydro-9,2,5-benzoxathiazacyclododecin-4-yl)methylidene]alanineN-{Hydroxy[(4R,7S)-6,12,14-trihydroxy-7-({hydroxy[(2S,3R)-3-hydroxy-1-serylpyrrolidin-2-yl]methylidene}amino)-11-methyl-10-oxo-1,3,4,7,8,10-hexahydro-9,2,5-benzoxathiazacyclododecin-4-yl]methylidene}-L-alanine
Properties
Computed structural properties
- XLogP
- -4.5
- Topological polar surface area
- 303 Ų
- Hydrogen bond donors
- 9
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 7
- Heavy atoms
- 44
- Formal charge
- 0
- Complexity
- 1,110
Physicochemical properties
- Boiling point
- 1253.4 · 1253.4±65.0 °C(Predicted)
- Density
- 1.6 · 1.60±0.1 g/cm3(Predicted)
- pka
- 3.61 · 3.61±0.10(Predicted)
Chemistry & industry
Applications
UsesCyclothialidine ( Ro 09-1437) is a potent DNA gyrase inhibitor isolated from Streptomyces filipinensisNR0484[1].
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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