Cephalothin (CHEM016623)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:38:43 UTC
Update Date2016-11-09 01:15:26 UTC
Accession NumberCHEM016623
Identification
Common NameCephalothin
ClassSmall Molecule
DescriptionCefalotin is a cephalosporin antibiotic.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acidChEBI
7-(2'-Thienylacetamido)cephalosporanic acidChEBI
7-(2-Thienylacetamido)cephalosporanic acidChEBI
7-(Thiophene-2-acetamido)cephalosporinChEBI
CefalothinChEBI
CefalotinaChEBI
CefalotineChEBI
CefalotinumChEBI
CephalothinChEBI
CephalotinChEBI
CETChEBI
Cefalotina fabraKegg
3-Acetoxymethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylateGenerator
7-(2'-Thienylacetamido)cephalosporanateGenerator
7-(2-Thienylacetamido)cephalosporanateGenerator
CephalothinumHMDB
CLSHMDB
CeftinaHMDB
Cephalothin monosodium saltHMDB
Cephalothin, sodiumHMDB
Lilly brand OF cephalothin sodiumHMDB
Sodium cephalothinHMDB
Spaly brand OF cephalothin sodiumHMDB
Cefalotina normonHMDB
Cefalotina sodica spalyHMDB
KeflinHMDB
Monosodium salt, cephalothinHMDB
Galen brand OF cephalothin sodiumHMDB
Normon brand OF cephalothin sodiumHMDB
Salt, cephalothin monosodiumHMDB
SeffinHMDB
Chemical FormulaC16H16N2O6S2
Average Molecular Mass396.438 g/mol
Monoisotopic Mass396.045 g/mol
CAS Registry Number153-61-7
IUPAC Name(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecephalothin
SMILES[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC1=CC=CS1)C(O)=O
InChI IdentifierInChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1
InChI KeyXIURVHNZVLADCM-IUODEOHRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporin 3'-esters
Alternative Parents
Substituents
  • Cephalosporin 3'-ester
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Meta-thiazine
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Thiophene
  • Tertiary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Carboxylic acid ester
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.052 g/LALOGPS
logP0.63ALOGPS
logP0.016ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area113.01 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity93.79 m³·mol⁻¹ChemAxon
Polarizability37.22 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9233000000-c08aaf4337c171abf2daSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0005-9112200000-c01dd68b0d32151deaf5Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-3497000000-39a3be7aed177d83e29cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06di-3592000000-2698fe462f117a84d906Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9450000000-e6bd7e836bf0464a7e99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-2924000000-f38cb8a2317e06bae695Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05is-6972000000-229017165a4e6bbe3d04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9320000000-99d96c92501fa08d35a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000b-0009000000-18bd1b9850bf3f0bc0deSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-2966000000-8c53c8dfe4afef2539ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-8983000000-bb2bc75f48bda3159248Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0019000000-2e169e448b42641dbb9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06r2-5659000000-26ef58de43fbebf7d124Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0537-9110000000-871abeea509049c819edSpectrum
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 IDDB00456
HMDB IDHMDB0014599
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDCLS
Wikipedia LinkCephalothin
Chemspider ID5802
ChEBI ID124991
PubChem Compound ID6024
Kegg Compound IDC07761
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10930630
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12569987
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=12833570
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1384868
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=13963283
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1701026
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=2083978
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23472927
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23680238
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=29017833
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6176550