7-Aminocephalosporanic acid(7-ACA) - 2mM in DMSO , CAS No.957-68-6

CAS: 957-68-6 Cat. No.: A427127 Molecular Weight: 272.28 Beilstein Registry Number: 622637 EC Number: 213-485-0

GRADE & PURITY 2mM in DMSO

Synonyms

(6R,7R)-3-((ACETYLOXY)METHYL)-7-AMINO-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID | 7-amino cephalosporanic acid | 7-Aminocephalosporanic-acid | (6R,7R)-3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic A

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Product Application
7-Aminocephalosporanic acid (7-ACA) can be used as a starting material to synthesize: Cefotaxime by acylation reaction with S-benzothiazol-2-yl(2-amino-4-thiazolyl)(methoxyimino)thioacetate (MAEM) in the presence of triethylamine. Cefpodoxime proxetil, a third-generation antibiotic via cefotaxime intermediate. Sodium 3′-substituted cephalosporanate sulfone derivatives as potential inhibitors of β-lactamase.

Specifications

Synonyms

(6R, 7R)-3-((ACETYLOXY)METHYL)-7-AMINO-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID | 7-amino cephalosporanic acid | 7-Aminocephalosporanic-acid | (6R, 7R)-3-[(Acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic A

Specifications & Purity

2mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CC(=O)OCC1=C(N2C(C(C2=O)N)SC1)C(=O)O
• IUPAC Name: (6R,7R)-3-(acetyloxymethyl)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• InChIKey: HSHGZXNAXBPPDL-HZGVNTEJSA-N
• INCHI: 1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)N)SC1)C(=O)O
• WGK Germany: 3
• Molecular Weight: 272.28
• Beilstein: 622637
• Reaxy-Rn: 622637
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=622637&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Alpha amino acids and derivatives
• Alternative Parents: Cephems 1,3-thiazines Dicarboxylic acids and derivatives Tertiary carboxylic acid amides Amino acids Azetidines Carboxylic acid esters Thiohemiaminal derivatives Azacyclic compounds Dialkylthioethers Carboxylic acids Carbonyl compounds Hydrocarbon derivatives Monoalkylamines Organic oxides Organopnictogen compounds
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Alpha-amino acid or derivatives - Cephem - Meta-thiazine - Dicarboxylic acid or derivatives - Beta-lactam - Tertiary carboxylic acid amide - Azetidine - Amino acid - Carboxamide group - Carboxylic acid ester - Lactam - Azacycle - Carboxylic acid - Organoheterocyclic compound - Dialkylthioether - Hemithioaminal - Thioether - Amine - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organopnictogen compound - Primary aliphatic amine - Organonitrogen compound - Organooxygen compound - Primary amine - Organic oxide - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
• External Descriptors: alpha,beta-unsaturated monocarboxylic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SLC15A1 Tchem Oligopeptide transporter small intestine isoform (922 Activities)

Discover Target: SLC15A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc15a2 Oligopeptide transporter, kidney isoform (114 Activities)

Discover Target: Slc15a2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: 90° (C=0.5,buffer sol. pH7.0 KH2PO4)
• Melt Point(°C): ＞300°C
• Molecular Weight: 272.280 g/mol
• XLogP3: -4.000
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 272.047 Da
• Monoisotopic Mass: 272.047 Da
• Topological Polar Surface Area: 135.000 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 461.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• 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

References

1. Weiwen Huang, Yichen Wang, Lumei Wang, Chaoqiang Pan, Guoqing Shen.  (2020)  Colorimetric detection of ciprofloxacin in aqueous solution based on an unmodified aptamer and the aggregation of gold nanoparticles.  Analytical Methods,  13  (1): (90-98).  [PMID:33300899] [10.1039/D0AY01811B]

2. Yi Haoyang, Yan Zhiyu, Wang Lumei, Zhou Xiaotong, Yan Rui, Zhang Dongwei, Shen Guoqing, Zhou Shanshan.  (2019)  Fluorometric determination for ofloxacin by using an aptamer and SYBR Green I.  MICROCHIMICA ACTA,  186  (10): (1-9).  [PMID:31486902] [10.1007/s00604-019-3788-8]

3. Yanyan Zhao, Yongbo Wang, Xuhua Liang, Huanxian Shi, Cunjin Wang, Jun Fan, Xiaoyun Hu, Enzhou Liu.  (2019)  Enhanced photocatalytic activity of Ag-CsPbBr3/CN composite for broad spectrum photocatalytic degradation of cephalosporin antibiotics 7-ACA.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2019.01.090]

4. Xuan Ni, Bing Xia, Lumei Wang, Jing Ye, Gaoshang Du, Haiwei Feng, Xiaotong Zhou, Tong Zhang, Wenhao Wang.  (2017)  Fluorescent aptasensor for 17β-estradiol determination based on gold nanoparticles quenching the fluorescence of Rhodamine B.  ANALYTICAL BIOCHEMISTRY,      [PMID:28137603] [10.1016/j.ab.2017.01.021]

5. Wei-Chuang Kong, Chen-Chen Li, Ai-Hong Zhang, Xin-Long Li, Qian-Rui Gong, Bing-Tan Jin, Xiao-Juan Jia, Xu-Ying Liu, Yan-Fei Kang.  (2024)  A colorimetric-aptamer-based assay for the determination of enrofloxacin through triggering the aggregation of gold nanoparticles.  Analytical Methods,      [PMID:39311407] [10.1039/D4AY01259C]

6. Wen-Yuan Fan, Xin Zhang, Dong-Hua Xie, Kenneth Mei Yee Leung, Guo-Ping Sheng.  (2024)  Cerium-based nanohydrolase for fast catalytic hydrolysis of β-lactam antibiotics in wastewater effluents.  JOURNAL OF HAZARDOUS MATERIALS,      [PMID:39644848] [10.1016/j.jhazmat.2024.136800]

7. 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]

8. Shuqi Xing, Wei Xie, Guangli Hu, Chaocheng Luo, Hong Zhu, Laping He, Cuiqin Li, Xiao Wang, Xuefeng Zeng.  (2024)  The synthesis of cinnamyl acetate and deacetyl-7-aminocephalosporanic acid by a GDSL-type esterase and its substrate specificity analysis.  ENZYME AND MICROBIAL TECHNOLOGY,      [PMID:39471645] [10.1016/j.enzmictec.2024.110532]

9. Zhiyu Yan, Haoyang Yi, Lumei Wang, Xiaotong Zhou, Rui Yan, Dongwei Zhang, Song Wang, Lantian Su, Shanshan Zhou.  (2019)  Fluorescent aptasensor for ofloxacin detection based on the aggregation of gold nanoparticles and its effect on quenching the fluorescence of Rhodamine B.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:31174139] [10.1016/j.saa.2019.117203]

10. Zhou Xiaotong, Wang Lumei, Shen Guoqing, Zhang Dongwei, Xie Jialun, Mamut Abdureyim, Huang Weiwen, Zhou Shanshan.  (2018)  Colorimetric determination of ofloxacin using unmodified aptamers and the aggregation of gold nanoparticles.  MICROCHIMICA ACTA,  185  (7): (1-9).  [PMID:29971570] [10.1007/s00604-018-2895-2]

11. Wei-Chuang Kong, Chen-Chen Li, Jun-Tao Niu, Xu-Ying Liu, Dong Wei, Yan-Fei Kang.  (2025)  A label-free aptasensor based on a fluorescent probe containing styrylbenzothiazole for detection of enrofloxacin.  Analytical Methods,      [PMID:40211802] [10.1039/D4AY02265C]