You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2018-05-20 20:20:36 UTC
HMDB IDHMDB0015574
Secondary Accession Numbers
  • HMDB15574
Metabolite Identification
Common NameLatamoxef
DescriptionBroad- spectrum beta-lactam antibiotic similar in structure to the cephalosporins except for the substitution of an oxaazabicyclo moiety for the thiaazabicyclo moiety of certain cephalosporins. It has been proposed especially for the meningitides because it passes the blood-brain barrier and for anaerobic infections. [PubChem]
Structure
Thumb
Synonyms
ValueSource
FestamoxinChEBI
LamoxactamChEBI
LatamoxefumChEBI
LMOXChEBI
Oxa-cephemChEBI
MoxalactamHMDB
Disodium latamoxefMeSH
Disodium, moxalactamMeSH
Latamoxef, disodiumMeSH
1 OxacephalosporinMeSH
1-OxacephalosporinMeSH
Disodium moxalactamMeSH
Moxalactam disodiumMeSH
Moxalactam, disodiumMeSH
ShiomarinMeSH
Chemical FormulaC20H20N6O9S
Average Molecular Weight520.473
Monoisotopic Molecular Weight520.101246958
IUPAC Name(6R,7R)-7-[2-carboxy-2-(4-hydroxyphenyl)acetamido]-7-methoxy-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Namelatamoxef
CAS Registry Number64952-97-2
SMILES
[H][C@]12OCC(CSC3=NN=NN3C)=C(N1C(=O)[C@]2(NC(=O)C(C(O)=O)C1=CC=C(O)C=C1)OC)C(O)=O
InChI Identifier
InChI=1S/C20H20N6O9S/c1-25-19(22-23-24-25)36-8-10-7-35-18-20(34-2,17(33)26(18)13(10)16(31)32)21-14(28)12(15(29)30)9-3-5-11(27)6-4-9/h3-6,12,18,27H,7-8H2,1-2H3,(H,21,28)(H,29,30)(H,31,32)/t12?,18-,20+/m1/s1
InChI KeyJWCSIUVGFCSJCK-CAVRMKNVSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-alpha amino acids and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha amino acid or derivatives
  • Phenylacetamide
  • Oxacephem
  • Aryl thioether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Alkylarylthioether
  • Monocyclic benzene moiety
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Azole
  • Beta-lactam
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Tetrazole
  • Azetidine
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Oxacycle
  • Carboxylic acid
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • 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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.75 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP0.22ALOGPS
logP0.17ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)2.92ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area206.3 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity133.7 m³·mol⁻¹ChemAxon
Polarizability47.24 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufu-2554920000-9ccc16f5a0c811c8cb66View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0002-5002069000-fcfc4810dc087dc9855aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fml-0110950000-57d22894c62264be15e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-0930200000-7e6509b24b50b053a363View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-0920100000-299f3fd6d8a2eefd712dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-1967610000-776d7de6814af49746f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0aor-8910400000-1fe14d5c919b1042fa01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-5970000000-1f1d3cbaec8e0aab9848View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04570 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB04570 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB04570
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID43215
KEGG Compound IDC07231
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLatamoxef
METLIN IDNot Available
PubChem Compound47499
PDB IDNot Available
ChEBI ID599928
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Brown RB, Klar J, Lemeshow S, Teres D, Pastides H, Sands M: Enhanced bleeding with cefoxitin or moxalactam. Statistical analysis within a defined population of 1493 patients. Arch Intern Med. 1986 Nov;146(11):2159-64. [PubMed:3778044 ]
  2. Weitekamp MR, Aber RC: Prolonged bleeding times and bleeding diathesis associated with moxalactam administration. JAMA. 1983 Jan 7;249(1):69-71. [PubMed:6217353 ]