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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:02 UTC
HMDB IDHMDB0015574
Secondary Accession Numbers
  • HMDB15574
Metabolite Identification
Common NameLatamoxef
DescriptionLatamoxef, also known as festamoxin or lamoxactam, belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom. Based on a literature review a significant number of articles have been published on Latamoxef.
Structure
Data?1582753312
Synonyms
ValueSource
FestamoxinChEBI
LamoxactamChEBI
LatamoxefumChEBI
LMOXChEBI
Oxa-cephemChEBI
MoxalactamHMDB
Disodium latamoxefHMDB
Disodium, moxalactamHMDB
Latamoxef, disodiumHMDB
1 OxacephalosporinHMDB
1-OxacephalosporinHMDB
Disodium moxalactamHMDB
Moxalactam disodiumHMDB
Moxalactam, disodiumHMDB
ShiomarinHMDB
LatamoxefChEBI
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
Description Belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. N-acyl-alpha amino acids and derivatives 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

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.75 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+214.79631661259
DarkChem[M-H]-208.42131661259
DeepCCS[M-2H]-237.24330932474
DeepCCS[M+Na]+212.87230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Latamoxef[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)=O5369.6Standard polar33892256
Latamoxef[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)=O3386.7Standard non polar33892256
Latamoxef[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)=O4171.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Latamoxef,1TMS,isomer #1CO[C@@]1(NC(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O)C=C2)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214198.6Semi standard non polar33892256
Latamoxef,1TMS,isomer #2CO[C@@]1(NC(=O)C(C(=O)O)C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214287.1Semi standard non polar33892256
Latamoxef,1TMS,isomer #3CO[C@@]1(NC(=O)C(C(=O)O)C2=CC=C(O)C=C2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214190.3Semi standard non polar33892256
Latamoxef,1TMS,isomer #4CO[C@@]1(N(C(=O)C(C(=O)O)C2=CC=C(O)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214171.2Semi standard non polar33892256
Latamoxef,2TMS,isomer #1CO[C@@]1(NC(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214154.9Semi standard non polar33892256
Latamoxef,2TMS,isomer #2CO[C@@]1(NC(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O)C=C2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214047.0Semi standard non polar33892256
Latamoxef,2TMS,isomer #3CO[C@@]1(N(C(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214008.8Semi standard non polar33892256
Latamoxef,2TMS,isomer #4CO[C@@]1(NC(=O)C(C(=O)O)C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214152.4Semi standard non polar33892256
Latamoxef,2TMS,isomer #5CO[C@@]1(N(C(=O)C(C(=O)O)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214128.7Semi standard non polar33892256
Latamoxef,2TMS,isomer #6CO[C@@]1(N(C(=O)C(C(=O)O)C2=CC=C(O)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]213999.5Semi standard non polar33892256
Latamoxef,3TMS,isomer #1CO[C@@]1(NC(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214074.0Semi standard non polar33892256
Latamoxef,3TMS,isomer #2CO[C@@]1(N(C(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214039.6Semi standard non polar33892256
Latamoxef,3TMS,isomer #3CO[C@@]1(N(C(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]213955.6Semi standard non polar33892256
Latamoxef,3TMS,isomer #4CO[C@@]1(N(C(=O)C(C(=O)O)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214030.3Semi standard non polar33892256
Latamoxef,4TMS,isomer #1CO[C@@]1(N(C(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214010.6Semi standard non polar33892256
Latamoxef,4TMS,isomer #1CO[C@@]1(N(C(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]213729.0Standard non polar33892256
Latamoxef,4TMS,isomer #1CO[C@@]1(N(C(=O)C(C(=O)O[Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C2)[Si](C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]215656.8Standard polar33892256
Latamoxef,1TBDMS,isomer #1CO[C@@]1(NC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214433.2Semi standard non polar33892256
Latamoxef,1TBDMS,isomer #2CO[C@@]1(NC(=O)C(C(=O)O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214506.7Semi standard non polar33892256
Latamoxef,1TBDMS,isomer #3CO[C@@]1(NC(=O)C(C(=O)O)C2=CC=C(O)C=C2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214415.5Semi standard non polar33892256
Latamoxef,1TBDMS,isomer #4CO[C@@]1(N(C(=O)C(C(=O)O)C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214433.2Semi standard non polar33892256
Latamoxef,2TBDMS,isomer #1CO[C@@]1(NC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214610.9Semi standard non polar33892256
Latamoxef,2TBDMS,isomer #2CO[C@@]1(NC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214512.0Semi standard non polar33892256
Latamoxef,2TBDMS,isomer #3CO[C@@]1(N(C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214494.7Semi standard non polar33892256
Latamoxef,2TBDMS,isomer #4CO[C@@]1(NC(=O)C(C(=O)O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214622.8Semi standard non polar33892256
Latamoxef,2TBDMS,isomer #5CO[C@@]1(N(C(=O)C(C(=O)O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214589.8Semi standard non polar33892256
Latamoxef,2TBDMS,isomer #6CO[C@@]1(N(C(=O)C(C(=O)O)C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214501.8Semi standard non polar33892256
Latamoxef,3TBDMS,isomer #1CO[C@@]1(NC(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214741.1Semi standard non polar33892256
Latamoxef,3TBDMS,isomer #2CO[C@@]1(N(C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O)=C(CSC3=NN=NN3C)CO[C@@H]214713.1Semi standard non polar33892256
Latamoxef,3TBDMS,isomer #3CO[C@@]1(N(C(=O)C(C(=O)O[Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214621.7Semi standard non polar33892256
Latamoxef,3TBDMS,isomer #4CO[C@@]1(N(C(=O)C(C(=O)O)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)[Si](C)(C)C(C)(C)C)C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C(CSC3=NN=NN3C)CO[C@@H]214721.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Latamoxef GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufu-2554920000-9ccc16f5a0c811c8cb662017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Latamoxef GC-MS (2 TMS) - 70eV, Positivesplash10-0002-5002069000-fcfc4810dc087dc9855a2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 10V, Positive-QTOFsplash10-0fml-0110950000-57d22894c62264be15e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 20V, Positive-QTOFsplash10-056r-0930200000-7e6509b24b50b053a3632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 40V, Positive-QTOFsplash10-0zfr-0920100000-299f3fd6d8a2eefd712d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 10V, Negative-QTOFsplash10-01b9-1967610000-776d7de6814af49746f22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 20V, Negative-QTOFsplash10-0aor-8910400000-1fe14d5c919b1042fa012016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 40V, Negative-QTOFsplash10-052b-5970000000-1f1d3cbaec8e0aab98482016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 10V, Positive-QTOFsplash10-0udi-0302290000-5de96a5b13c0e07919d42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 20V, Positive-QTOFsplash10-0ufr-0836490000-991b57dd6b18e8d73d352021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 40V, Positive-QTOFsplash10-001i-1901300000-73b3b88db9aeadfe36092021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 10V, Negative-QTOFsplash10-014i-0701390000-e8d5e3d3c75f5a8a82dc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 20V, Negative-QTOFsplash10-014i-2910020000-c32579f60fb91a6747f92021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latamoxef 40V, Negative-QTOFsplash10-066r-6911000000-20efb6f673da8484a9762021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB04570 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]