7-Aminocephalosporanic acid (CHEM018255)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:06:02 UTC
Update Date2016-11-09 01:15:45 UTC
Accession NumberCHEM018255
Identification
Common Name7-Aminocephalosporanic acid
ClassSmall Molecule
DescriptionThe alpha,beta-unsaturated monocarboxylic acid that is the active nucleus for the synthesis of cephalosporins and intermediates.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(7R)-7-AminocephalosporanateChEBI
7-ACAChEBI
7-Aminocephalosporanic acidChEBI
7-Aminocephalosporinic acidChEBI
(7R)-7-Aminocephalosporanic acidGenerator
7-AminocephalosporanateGenerator
7-AminocephalosporinateGenerator
7b-AminocephalosporanateGenerator
7b-Aminocephalosporanic acidGenerator
7beta-AminocephalosporanateGenerator
7Β-aminocephalosporanateGenerator
7Β-aminocephalosporanic acidGenerator
7-ACA CPDMeSH
Chemical FormulaC10H12N2O5S
Average Molecular Mass272.278 g/mol
Monoisotopic Mass272.047 g/mol
CAS Registry Number957-68-6
IUPAC Name(6R,7R)-3-[(acetyloxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Name7β-aminocephalosporanic acid
SMILES[H][C@@]1(N)C(=O)N2C(C(O)=O)=C(COC(C)=O)CS[C@]12[H]
InChI IdentifierInChI=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
InChI KeyHSHGZXNAXBPPDL-HZGVNTEJSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
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
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
  • alpha,beta-unsaturated monocarboxylic acid (CHEBI:2255 )
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.72 g/LALOGPS
logP-1ALOGPS
logP-3.8ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.42ChemAxon
pKa (Strongest Basic)7.39ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area109.93 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.74 m³·mol⁻¹ChemAxon
Polarizability25.57 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9080000000-612cfdce5904343c8bc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-044i-1590000000-8d548a0e17acf1826179Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9300000000-d92dbfb13f2f0389d65dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9250000000-cbd7254c13c26c9a7e74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9100000000-d8a588622ea97950e61dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-cceb54c20d73d0aa314bSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID2255
PubChem Compound ID441328
Kegg Compound IDC07756
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1384868