Determine the necessary mass, volume, or concentration for preparing a solution.
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Moligand™, ≥98% Moligand™ 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 12 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Oxacillin is an orally active synthetic penicillin with good bactericidal activity against staphylococci and other gram-positive pathogens.
| Canonical Smiles | OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)c1c(C)onc1c1ccccc1 |
|---|---|
| IUPAC Name | (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
| InChIKey | UWYHMGVUTGAWSP-JKIFEVAISA-N |
| INCHI | 1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1 |
| Isomeric SMILES | CC1=C(C(=NO1)C2=CC=CC=C2)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O |
| Molecular Weight | 401.44 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Peptides |
| Direct Parent | Dipeptides |
| Alternative Parents | Penicillins N-acyl-alpha amino acids and derivatives Benzene and substituted derivatives Tertiary carboxylic acid amides Thiazolidines Heteroaromatic compounds Isoxazoles Secondary carboxylic acid amides Azetidines Thiohemiaminal derivatives Oxacyclic compounds Carboxylic acids Dialkylthioethers Monocarboxylic acids and derivatives Azacyclic compounds Organonitrogen compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Carbonyl compounds |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Alpha-dipeptide - Penicillin - N-acyl-alpha amino acid or derivatives - Alpha-amino acid or derivatives - Penam - Benzenoid - Monocyclic benzene moiety - Isoxazole - Tertiary carboxylic acid amide - Azole - Thiazolidine - Heteroaromatic compound - Beta-lactam - Carboxamide group - Lactam - Secondary carboxylic acid amide - Azetidine - Oxacycle - Carboxylic acid - Azacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Dialkylthioether - Hemithioaminal - Thioether - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Carbonyl group - Organic nitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
| External Descriptors | penicillin |
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| Sensitivity | Moisture sensitive |
|---|---|
| Molecular Weight | 401.400 g/mol |
| XLogP3 | 2.400 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 7 |
| Rotatable Bond Count | 4 |
| Exact Mass | 401.105 Da |
| Monoisotopic Mass | 401.105 Da |
| Topological Polar Surface Area | 138.000 Ų |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Complexity | 680.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 3 |
| 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 |
| 1. Meiling Ping, Wenchao Lv, Chen Yang, Qian Chen, Zongwen Wang, Fengfu Fu. (2023) A Paper-Based Multicolor Colorimetric Aptasensor for the Visual Determination of Multiple Sulfonamides Based on Aptamer-Functionalized Magnetic Beads and NADH–Ascorbic Acid-Mediated Gold Nanobipyramids. Chemosensors, 11 (7): (386). [PMID:] [10.3390/chemosensors11070386] |
| 2. Zongwen Wang, Xiating Li, Feng Zhang, Yu Gao, Jintian Cheng, FengFu Fu. (2023) Regulating the Growth Rate of Gold Nanobipyramids via a HCl-NADH-Ascorbic Acid System toward a Dual-Channel Multicolor Colorimetric Immunoassay for Simultaneously Screening and Detecting Multiple Sulfonamides. ANALYTICAL CHEMISTRY, [PMID:37382204] [10.1021/acs.analchem.3c01928] |
| 3. Yexuan Mao, Yichao Fan, Ran Yang, Youyi Wang, Qingyue Li, Meng Dang, Xianqing Huang, Lianjun Song, Pingan Zhang, Miao Song, Liang Liu, Linli Wang, Shun Yu, Qiuyan Zhao, Xiya Zhang. (2023) A highly sensitive electrochemical sensor derived from peptide amphiphilic inspired self-assembled, ordered gold nanoparticles for determination of 22 β-lactams. ELECTROCHIMICA ACTA, [PMID:] [10.1016/j.electacta.2023.142669] |
| 4. Lu Yunfu, Chen Feifei, Zhao Qingmin, Cao Qiao, Chen Rongrong, Pan Huiwen, Wang Yanhui, Huang Haixin, Huang Ruimin, Liu Qian, Li Min, Bae Taeok, Liang Haihua, Lan Lefu. (2023) Modulation of MRSA virulence gene expression by the wall teichoic acid enzyme TarO. Nature Communications, 14 (1): (1-19). [PMID:36949052] [10.1038/s41467-023-37310-5] |
| 5. Xuan Ma, Yue Wang, Wenting Wang, Jake Heinlein, Lisa D. Pfefferle, Xuemeng Tian. (2023) Strategic preparation of porous magnetic molecularly imprinted polymers via a simple and green method for high-performance adsorption and removal of meropenem. TALANTA, [PMID:36893497] [10.1016/j.talanta.2023.124419] |
| 6. Yuanping Fang, Congli Chen, Bin Cui, Dandan Zhou. (2023) Self-rescue of nitrogen-cycling bacteria under β-lactam antibiotics stress during managed aquifer recharge (MAR): Microbial collaboration and anti-resistance. WATER RESEARCH, [PMID:36689880] [10.1016/j.watres.2023.119623] |
| 7. Chong-Fa Lai, Wei-Bin Xiao, Hua-Cheng Yan, Hui Yang, Lu-Xia Wang, Hui Guan, Qiu-ju Peng, Zhi-Rong Deng, Jian-Wen Chen, Lin-Kun An, Lei Shi. (2020) ZTW-41, a Potent Indolizinoquinoline-5,12-Dione Derivative Against Drug-Resistant Staphylococci and Enterococci Bacteria. Microbial Drug Resistance, 26 (2): (100-109). [PMID:31441704] [10.1089/mdr.2019.0008] |
| 8. Zhenbin Chen, Haohan Cai, Feng Huang, Zongping Wang, Yiqun Chen, Zizheng Liu, Pengchao Xie. (2024) Degradation of β-lactam antibiotics by Fe(III)/HSO3− system and their quantitative structure-activity relationship. ENVIRONMENTAL RESEARCH, [PMID:38986801] [10.1016/j.envres.2024.119577] |
| 9. Lin Zhang, Siqi Wu, Junfeng Liu, Meiling Ping, Weijuan Yang, FengFu Fu. (2024) Isolation of aptamers with excellent cross-reactivity and specificity to sulfonamides towards a ratiometric fluorescent aptasensor for the detection of nine sulfonamides in seafood. TALANTA, [PMID:38852344] [10.1016/j.talanta.2024.126380] |
| 10. Aftab Khan, Samreen Sadiq, Iltaf Khan, Muhammad Humayun, Guo Jiyuan, Muhammad Usman, Abbas Khan, Shoaib Khan, Amal Faleh Alanazi, Mohamed Bououdina. (2024) Preparation of visible-light active MOFs-Perovskites (ZIF-67/LaFeO3) nanocatalysts for exceptional CO2 conversion, organic pollutants and antibiotics degradation. Heliyon, [PMID:38486780] [10.1016/j.heliyon.2024.e27378] |
| 11. Yating Tang, Jingming Zhao, Huiqin Suo, Chunjie Hu, Qingjie Li, Guofeng Li, Shaoyu Han, Xin Su, Wu Song, Mengli Jin, Yufen Li, Songyang Li, Lin Wei, Xin Jiang, Shuang Jiang. (2024) Sinigrin reduces the virulence of Staphylococcus aureus by targeting coagulase. MICROBIAL PATHOGENESIS, [PMID:39117013] [10.1016/j.micpath.2024.106841] |
| 12. Huiting Feng, Yuxin Yang, Ruiling Li, Yuting Yang, Zongwen Wang, FengFu Fu, Yue Lin. (2026) Employment of mixed aptamers and gold nanobipyramids toward a paper-based aptasensor for simultaneously visual screening and accurate detection of eight sulfonamides. SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, [PMID:] [10.1016/j.saa.2026.127574] |
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