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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2019-07-23 06:00:37 UTC
HMDB IDHMDB0014827
Secondary Accession Numbers
  • HMDB14827
Metabolite Identification
Common NameCephaloglycin
DescriptionCephaloglycin is only found in individuals that have used or taken this drug. It is a cephalorsporin antibiotic.The bactericidal activity of cephaloglycin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Structure
Data?1563861637
Synonyms
ValueSource
7-(2-D-alpha-aminophenylacetamido)Cephalosporanic acidChEBI
7-(D-alpha-Aminophenyl-acetamido)cephalosporanic acidChEBI
CefaloglicinaChEBI
CefaloglycineChEBI
CefaloglycinumChEBI
CEGChEBI
CephaloglycineChEBI
Cephaoglycin acidChEBI
D-(-)-CephaloglycinChEBI
D-CephaloglycineChEBI
7-(2-D-a-aminophenylacetamido)CephalosporanateGenerator
7-(2-D-a-aminophenylacetamido)Cephalosporanic acidGenerator
7-(2-D-alpha-aminophenylacetamido)CephalosporanateGenerator
7-(2-D-α-aminophenylacetamido)cephalosporanateGenerator
7-(2-D-α-aminophenylacetamido)cephalosporanic acidGenerator
7-(D-a-Aminophenyl-acetamido)cephalosporanateGenerator
7-(D-a-Aminophenyl-acetamido)cephalosporanic acidGenerator
7-(D-alpha-Aminophenyl-acetamido)cephalosporanateGenerator
7-(D-α-aminophenyl-acetamido)cephalosporanateGenerator
7-(D-α-aminophenyl-acetamido)cephalosporanic acidGenerator
Cephaloglycin dihydrateMeSH
Dihydrate, cephaloglycinMeSH
Chemical FormulaC18H19N3O6S
Average Molecular Weight405.425
Monoisotopic Molecular Weight405.099456045
IUPAC Name(6R,7R)-3-[(acetyloxy)methyl]-7-[(2R)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namecephaloglycin
CAS Registry Number3577-01-3
SMILES
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1S/C18H19N3O6S/c1-9(22)27-7-11-8-28-17-13(16(24)21(17)14(11)18(25)26)20-15(23)12(19)10-5-3-2-4-6-10/h2-6,12-13,17H,7-8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1
InChI KeyFUBBGQLTSCSAON-PBFPGSCMSA-N
Chemical Taxonomy
DescriptionThis compound 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 amide
  • Alpha-amino acid or derivatives
  • Phenylacetamide
  • Aralkylamine
  • Meta-thiazine
  • Dicarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Amino acid
  • Carboxamide group
  • Azetidine
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Thioether
  • Hemithioaminal
  • Dialkylthioether
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point237 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.15 g/LNot Available
LogP-0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP0.54ALOGPS
logP-3ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area139.03 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.9 m³·mol⁻¹ChemAxon
Polarizability37.64 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1900000000-1eeacfc36b9f04a35c7cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2900100000-bf904d469f6a64516ca7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-2964100000-336b895ce35617e52a13JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2961000000-497ca6fb1f0eb94d6ac0JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-6910000000-8c2acee21fe03a2d11a6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1924100000-ffc083742bea5a17b893JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-7982000000-5b30a169999deff2a54cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9310000000-3ce8e6b000720967a74cJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00689 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00689 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00689
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID18069
KEGG Compound IDC13440
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCephaloglycin
METLIN IDNot Available
PubChem Compound19150
PDB IDNot Available
ChEBI ID34613
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tune BM, Hsu CY: The renal mitochondrial toxicity of beta-lactam antibiotics: in vitro effects of cephaloglycin and imipenem. J Am Soc Nephrol. 1990 Nov;1(5):815-21. [PubMed:2133431 ]
  2. Tune BM, Fravert D, Hsu CY: Oxidative and mitochondrial toxic effects of cephalosporin antibiotics in the kidney. A comparative study of cephaloridine and cephaloglycin. Biochem Pharmacol. 1989 Mar 1;38(5):795-802. [PubMed:2930580 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:
SLC22A5
Uniprot ID:
O76082
Molecular weight:
62751.1
References
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100 ]