(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CED0130163)

Record Information
Version1.0
Creation Date2016-06-03 11:03:22 UTC
Update Date2026-05-14 19:33:47 UTC
Accession NumberCHEM043563
Identification
Common Name(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
ClassSmall Molecule
Description
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid belongs to the beta lactams, a subclass of lactams within the organic compounds. With an average molecular weight of 584.66 g/mol, (6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is a heavy molecule. It has the chemical formula C20H20N6O7S4 and is classified as an organoheterocyclic compound. The compound is found in or released from two recorded sources: drinking water and water supply (drinking water), as well as healthcare, pharmaceuticals, and veterinary products (antibiotics). Recorded exposure routes include oral and inhalation. This molecule interacts with seven recorded protein targets, acting as an inhibitor of Penicillin-binding protein 1A (mrcA), Penicillin-binding protein 1B (mrcB), D-alanyl-D-alanine carboxypeptidase DacC (dacC), and Peptidoglycan D,D-transpeptidase MrdA (mrdA), in addition to three other proteins.
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(6R,7R)-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-7-{[(2E)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R)-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulphanyl}methyl)-7-{[(2E)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(6R,7R)-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulphanyl}methyl)-7-{[(2E)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator
Chemical FormulaC20H20N6O7S4
Average Molecular Mass584.660 g/mol
Monoisotopic Mass584.028 g/mol
CAS Registry Number69739-16-8
IUPAC Name(6R,7R)-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-7-{[(2E)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Traditional Name(6R,7R)-3-({[5-(carboxymethyl)-4-methyl-1,3-thiazol-2-yl]sulfanyl}methyl)-7-{[(2E)-1-hydroxy-2-(2-imino-3H-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES[H][C@]12SCC(CSC3=NC(C)=C(CC(O)=O)S3)=C(N1C(=O)[C@@]2([H])N=C(O)C(=N\OC)\C1=CSC(=N)N1)C(O)=O
InChI IdentifierInChI=1S/C20H20N6O7S4/c1-7-10(3-11(27)28)37-20(22-7)36-5-8-4-34-17-13(16(30)26(17)14(8)18(31)32)24-15(29)12(25-33-2)9-6-35-19(21)23-9/h6,13,17H,3-5H2,1-2H3,(H2,21,23)(H,24,29)(H,27,28)(H,31,32)/b25-12+/t13-,17-/m1/s1
InChI KeyXDZKBRJLTGRPSS-ZSKFQXOHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cephalosporins. Cephalosporins are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]Oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Aryl thioether
  • 2,4,5-trisubstituted 1,3-thiazole
  • 2,4-disubstituted 1,3-thiazole
  • Alkylarylthioether
  • Meta-thiazine
  • Dicarboxylic acid or derivatives
  • 1,3-thiazol-2-amine
  • Heteroaromatic compound
  • Azole
  • Tertiary carboxylic acid amide
  • Thiazole
  • Amino acid
  • Amino acid or derivatives
  • Carboxamide group
  • Azetidine
  • Secondary carboxylic acid amide
  • Dialkylthioether
  • Carboxylic acid
  • Azacycle
  • Carboxylic acid derivative
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organosulfur compound
  • Primary amine
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.093 g/LALOGPS
logP1.25ALOGPS
logP1.93ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)3.12ChemAxon
pKa (Strongest Basic)1.32ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area197.86 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity150.24 m³·mol⁻¹ChemAxon
Polarizability57.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00my-2155690000-c5da4cc8fff3aa2106acNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4j-4968240000-53fe3d302ebadeacae42Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-9545200000-06206ff66270c2fdc9abNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000i-0690040000-b53432a61409cc0c91b8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zg0-0920000000-cb8f64af229fa949b099Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfu-7900000000-537ac11308aff0fc99f6Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5065.0Log mg/kg[2800:9000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
115Drinking waterDrinking water & water supplyNot Available
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)2.10193
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)2.80257
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansPredicted (SEA)0.856341
Click to view 3D structureBeta-lactamaseB2ZTR6Acinetobacter baumanniiPredicted (SEA)0.544945
Click to view 3D structureADC-11D6NSM8Acinetobacter baumanniiPredicted (SEA)0.544945
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)922.903
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)22.9655
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)1313.78
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)3272.0
26S proteasome non-ATPase regulatory subunit 14 structureClick to view 3D structure26S proteasome non-ATPase regulatory subunit 14O00487HumansPredicted (SEA)251.219
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)1241.62
Peptidoglycan D,D-transpeptidase FtsI structureClick to view 3D structurePeptidoglycan D,D-transpeptidase FtsIQ51504Pseudomonas aeruginosaPredicted (SEA)5.52729
DNA (cytosine-5)-methyltransferase 1 structureClick to view 3D structureDNA (cytosine-5)-methyltransferase 1P26358HumansPredicted (SEA)2713.12
Small ubiquitin-related modifier 1 structureClick to view 3D structureSmall ubiquitin-related modifier 1P63165HumansPredicted (SEA)2572.76
Click to view 3D structureAmpCQ83TT7Escherichia coliPredicted (SEA)4.35956
D-amino-acid oxidase structureClick to view 3D structureD-amino-acid oxidaseP14920HumansPredicted (SEA)904.841
Click to view 3D structureSHV-5 extended spectrum beta-lactamaseQ6REX6Escherichia coliPredicted (SEA)26.0795
Tyrosine-protein phosphatase non-receptor type 11 structureClick to view 3D structureTyrosine-protein phosphatase non-receptor type 11Q06124HumansPredicted (SEA)3985.1
Excitatory amino acid transporter 2 structureClick to view 3D structureExcitatory amino acid transporter 2P43004HumansPredicted (SEA)1225.81
Penicillin-binding protein 1A structureClick to view 3D structurePenicillin-binding protein 1AQ07806Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Predicted (SEA)8.71911
Dual specificity protein phosphatase 3 structureClick to view 3D structureDual specificity protein phosphatase 3P51452HumansPredicted (SEA)4867.6
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)6.61718
Click to view 3D structureGlutamate receptor ionotropic, kainate 5Q61626Mus musculusPredicted (SEA)62.5129
Click to view 3D structureProbable nicotinate-nucleotide adenylyltransferaseP65502Staphylococcus aureus (strain N315)Predicted (SEA)3178.19
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)48.7336
Concentrations
Not Available
External Links
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 IDNot Available
PubChem Compound ID6321412
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References