≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at -20°C Ships Ice chest + Ice pads Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Bicyclomycin benzoate is a polar metabolite first isolated from Streptomyces sapporonensis in 1972 with activity against Gram negative bacteria. The selective Gram negative profile of Bicyclomycin benzoate is rare among Streptomyces metabolites, and in an effort to overcome its poor in vivo absorption, the benzoate ester was prepared by reaction with the more exposed primary alcohol.
| Canonical Smiles | CC(COC(=O)C1=CC=CC=C1)(C(C23C(=O)NC(C(=C)CCO2)(C(=O)N3)O)O)O |
|---|---|
| IUPAC Name | [(2S,3S)-2,3-dihydroxy-3-[(1S,6R)-6-hydroxy-5-methylidene-8,10-dioxo-2-oxa-7,9-diazabicyclo[4.2.2]decan-1-yl]-2-methylpropyl] benzoate |
| InChIKey | YYGLCPHONATYBU-FZDIXFNVSA-N |
| INCHI | 1S/C19H22N2O8/c1-11-8-9-29-19(16(25)20-18(11,27)15(24)21-19)14(23)17(2,26)10-28-13(22)12-6-4-3-5-7-12/h3-7,14,23,26-27H,1,8-10H2,2H3,(H,20,25)(H,21,24)/t14-,17-,18+,19-/m0/s1 |
| Isomeric SMILES | C[C@](COC(=O)C1=CC=CC=C1)([C@@H]([C@@]23C(=O)N[C@@](C(=C)CCO2)(C(=O)N3)O)O)O |
| RTECS | DT7470000 |
| PubChem CID | 91618023 |
| Molecular Weight | 406.39 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Benzoic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Benzoic acid esters |
| Alternative Parents | Alpha amino acids and derivatives Benzoyl derivatives 2,5-dioxopiperazines Tertiary alcohols Secondary carboxylic acid amides Secondary alcohols Lactams Carboxylic acid esters 1,2-diols Oxacyclic compounds Azacyclic compounds Alkanolamines Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Alpha-amino acid or derivatives - Benzoate ester - Dioxopiperazine - Benzoyl - 2,5-dioxopiperazine - 1,4-diazinane - Piperazine - Tertiary alcohol - Carboxylic acid ester - 1,2-diol - Lactam - Carboxamide group - Secondary alcohol - Secondary carboxylic acid amide - Oxacycle - Azacycle - Carboxylic acid derivative - Alkanolamine - Organoheterocyclic compound - Organic nitrogen compound - Organonitrogen compound - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Alcohol - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. |
| External Descriptors | Not available |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO, and water (Partial). |
|---|---|
| Sensitivity | Moisture sensitive. |
| Molecular Weight | 406.400 g/mol |
| XLogP3 | -0.700 |
| Hydrogen Bond Donor Count | 5 |
| Hydrogen Bond Acceptor Count | 8 |
| Rotatable Bond Count | 6 |
| Exact Mass | 406.138 Da |
| Monoisotopic Mass | 406.138 Da |
| Topological Polar Surface Area | 154.000 Ų |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Complexity | 721.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
