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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N2O5S
Molecular Weight 272.278
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 7-Aminocephalosporanic acid

SMILES

CC(=O)OCC1=C(N2[C@H](SC1)[C@H](N)C2=O)C(O)=O

InChI

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

HIDE SMILES / InChI
Molecular Formula C10H12N2O5S
Molecular Weight 272.278
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

7-aminocephalosporanicacid (7-ACA) is convenient starting material for the industrial production of various kinds of semisynthetic cephalosporin antibiotics. In many cases, chemical modifications at the C-7 position is required. Industrially, 7-ACA is derived by chemical or enzymatic deacylation from cephalosporin C, which is fermentatively produced by Acremonium chrysogenum. 7-ACA is a stable only at neutral pHs, enzymatic manipulations are desirable for chemical modifications in the production of cephalosporin related compounds.

Originator

Pfizer
420
Curator's Comment: # Pfizer & Co C

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Gene expressions changes in bronchial epithelial cells: markers for respiratory sensitizers and exploration of the NRF2 pathway.
2014-03
Occupational asthma in Korea.
2010-12
Environmentally safe production of 7-ACA by recombinant Acremonium chrysogenum.
2010-12
Biosynthesis of cephalosporin-C acylase enzyme: optimal media design, purification, and characterization.
2010-10
Enhancement of glutaryl-7-aminocephalosporanic acid acylase activity of gamma-glutamyltranspeptidase of Bacillus subtilis.
2010-08
Protein engineering of penicillin acylase.
2010-07
Stepwise engineering of a Pichia pastoris D-amino acid oxidase whole cell catalyst.
2010-04-26
A single Phe54Tyr substitution improves the catalytic activity and thermostability of Trigonopsis variabilis D-amino acid oxidase.
2010-02-28
Improved cross-linked enzyme aggregates for the production of desacetyl beta-lactam antibiotics intermediates.
2010-01
Optimization of glutaryl-7-aminocephalosporanic acid acylase expression in E. coli.
2008-10
The stabilizing effects of immobilization in D-amino acid oxidase from Trigonopsis variabilis.
2008-09-17
YesT: a new rhamnogalacturonan acetyl esterase from Bacillus subtilis.
2008-04
Development of the semi-synthetic penicillins and cephalosporins.
2008-03
Properties and applications of microbial D-amino acid oxidases: current state and perspectives.
2008-02
Enzymatic synthesis of cephalosporins. The immobilized acylase from Arthrobacter viscosus: a new useful biocatalyst.
2007-12
A colorimetric assay for the determination of acetyl xylan esterase or cephalosporin C acetyl esterase activities using 7-amino cephalosporanic acid, cephalosporin C, or acetylated xylan as substrate.
2007-10-15
[7-aminocephalosporanic acid induced bronchial asthma in two patients].
2007-10
New active site oriented glyoxyl-agarose derivatives of Escherichia coli penicillin G acylase.
2007-09-10
Site-specific protonation microequilibria of penicillin and cephalosporin beta-lactam core molecules.
2007-09
Construction of recombinant Escherichia coli D11/pMSTO and its use in enzymatic preparation of 7-aminocephalosporanic acid in one pot.
2007-05-01
Reusability of entrapped cells of Pseudomonas diminuta for production of 7-aminocephalosporanic acid.
2007-04
[Microspeciation of amphoteric molecules of unusual acid-base properties].
2007
Microbial production of 7-amino-cephalosporanic acid and new generation cephalosporins (cephalothin) by different processing strategies.
2007
Thermal inactivation of D-amino acid oxidase from Trigonopsis variabilis occurs via three parallel paths of irreversible denaturation.
2006-07-05
Enzymatic modifications of cephalosporins by cephalosporin acylase and other enzymes.
2006-07-01
Spectrophotometric assay for quantitative determination of 7-aminocephalosporanic acid from direct hydrolysis of cephalosporin C.
2006-03-15
Evolution of an acylase active on cephalosporin C.
2005-12
Purification and characterization of a novel aminoacylase from Streptomyces mobaraensis.
2005-10
Single-step conversion of cephalosporin-C to 7-aminocephalosporanic acid by free and immobilized cells of Pseudomonas diminuta.
2005-07
Reactions of pyrazolylborate-zinc-hydroxide complexes related to beta-lactamase activity.
2005-06-13
1H and 13 C spectral assignments of 7beta-(cinnamoyl-substituted)amino-3-acetoxymethyl-cephalosporins.
2005-03
D-Amino acid oxidase: structure, catalytic mechanism, and practical application.
2005-01
Toward the development of a cephalosporin-based dual-release prodrug for use in ADEPT.
2004-11-12
Batch production of deacetyl 7-aminocephalosporanic acid by immobilized cephalosporin-C deacetylase.
2004-08
[Compared D-amino acid oxidase expression in different Pichia pastoris host strains].
2004-07
Modifying the substrate specificity of penicillin G acylase to cephalosporin acylase by mutating active-site residues.
2004-06-25
Construction and application of fusion proteins of D-amino acid oxidase and glutaryl-7-aminocephalosporanic acid acylase for direct bioconversion of cephalosporin C to 7-aminocephalosporanic acid.
2004-06
Catalytic properties of D-amino acid oxidase in cephalosporin C bioconversion: a comparison between proteins from different sources.
2004-04-03
Occupational asthma and IgE sensitization to 7-aminocephalosporanic acid.
2004-04
Affinity labeled glutaryl-7-amino cephalosporanic acid acylase C130 can hydrolyze the inhibitor during crystallization.
2004-01-16
Industrial enzymatic production of cephalosporin-based beta-lactams.
2004
Synthesis and preliminary antimicrobial evaluation of new 7-(N-pyrrolyl) derivatives of cephalosporins.
2004
Deacylation activity of cephalosporin acylase to cephalosporin C is improved by changing the side-chain conformations of active-site residues.
2003-10-10
Multivariate analysis and classification of the chemical quality of 7-aminocephalosporanic acid using near-infrared reflectance spectroscopy.
2003-07-15
A rapid and specific method to screen environmental microorganisms for cephalosporin acylase activity.
2003-07
The kinetic properties of the carboxy terminal domain of the Bacillus licheniformis 749/I BlaR penicillin-receptor shed a new light on the derepression of beta-lactamase synthesis.
2003-06
An alternative procedure for preparation of cefdinir.
2003-06
An improved method for preparation of cefpodoxime proxetil.
2003-05
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.
1992
[Thoughts on explaining cigarette smoking].
1987-02
Patents

Patents

JP1056682A
1
JP1090190A
1
JP2001507688A
27
JP2001525667A
12
JP2002000266A
1
JP2005198655A
1
JP2005348743A
1
JP3903392B2
21
JPH00453499A
1
JPH00568551A
1
JPH00584077A
1
JPH00584078A
1
JPH00898683A
1
JPH00898686A
1
JPH01131182A
1
JPH02160791A
1
JPH022396A
1
JPH0242085A
1
JPH02456A
1
JPH04104792A
1
JPH04198184A
1
JPH04211088A
1
JPH04230689A
1
JPH0453499A
1
JPH05211889A
1
JPH05211890A
1
JPH0568551A
1
JPH0584077A
1
JPH0584078A
1
JPH06141857A
1
JPH06184161A
1
JPH06225794A
1
JPH0646835A
1
JPH0680673A
1
JPH0690746A
1
JPH07145173A
1
JPH07165765A
1
JPH07222587A
1
JPH07303483A
1
JPH07313161A
1
JPH08224089A
1
JPH08242884A
1
JPH08256789A
1
JPH08301874A
1
JPH0898683A
1
JPH0898686A
1
JPH0948784A
1
JPH10291991A
1
JPH10291993A
1
JPH1160583A
1
JPS05238092A
4

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:36:02 GMT 2025
Edited
by admin
on Mon Mar 31 17:36:02 GMT 2025
Record UNII
9XI67897RG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
7-ACA
Preferred Name English
7-Aminocephalosporanic acid
MI  
Common Name English
CEFTRIAXONE SODIUM IMPURITY E [IP]
Common Name English
CEFAZOLIN SODIUM IMPURITY H [EP IMPURITY]
Common Name English
3-(ACETOXYMETHYL)-7-AMINOCEPHEM-4-CARBOXYLIC ACID
Common Name English
CEFOPERAZONE SODIUM IMPURITY E [EP IMPURITY]
Common Name English
(7R)-7-AMINOCEPHALOSPORANIC ACID
Common Name English
7.BETA.-AMINO-3-ACETOXYMETHYLCEPHEMCARBOXYLIC ACID
Common Name English
(6R,7R)-3-((ACETYLOXY)METHYL)-7-AMINO-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
3-ACETOXYMETHYL-7.BETA.-AMINOCEPH-3-EM-4-CARBOXYLIC ACID
Common Name English
7.BETA.-AMINOCEPHALOSPORANIC ACID
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-AMINO-8-OXO-, (6R,7R)-
Systematic Name English
7-AMINOCEPHALOSPORANIC ACID [MI]
Common Name English
7-Aminocephalosporanic acid [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
9XI67897RG
Created by admin on Mon Mar 31 17:36:02 GMT 2025 , Edited by admin on Mon Mar 31 17:36:02 GMT 2025
PRIMARY
ECHA (EC/EINECS)
213-485-0
Created by admin on Mon Mar 31 17:36:02 GMT 2025 , Edited by admin on Mon Mar 31 17:36:02 GMT 2025
PRIMARY
CHEBI
2255
Created by admin on Mon Mar 31 17:36:02 GMT 2025 , Edited by admin on Mon Mar 31 17:36:02 GMT 2025
PRIMARY
MERCK INDEX
m1699
Created by admin on Mon Mar 31 17:36:02 GMT 2025 , Edited by admin on Mon Mar 31 17:36:02 GMT 2025
PRIMARY Merck Index
PUBCHEM
441328
Created by admin on Mon Mar 31 17:36:02 GMT 2025 , Edited by admin on Mon Mar 31 17:36:02 GMT 2025
PRIMARY
CAS
957-68-6
Created by admin on Mon Mar 31 17:36:02 GMT 2025 , Edited by admin on Mon Mar 31 17:36:02 GMT 2025
PRIMARY
MESH
C030735
Created by admin on Mon Mar 31 17:36:02 GMT 2025 , Edited by admin on Mon Mar 31 17:36:02 GMT 2025
PRIMARY
WIKIPEDIA
7-ACA
Created by admin on Mon Mar 31 17:36:02 GMT 2025 , Edited by admin on Mon Mar 31 17:36:02 GMT 2025
PRIMARY
EPA CompTox
DTXSID9045342
Created by admin on Mon Mar 31 17:36:02 GMT 2025 , Edited by admin on Mon Mar 31 17:36:02 GMT 2025
PRIMARY
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NCATS
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