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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:46:24 UTC
Update Date2022-03-07 02:57:13 UTC
HMDB IDHMDB0041892
Secondary Accession Numbers
  • HMDB41892
Metabolite Identification
Common NameFaropenem
DescriptionFaropenem, also known as faropenem sodium, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Based on a literature review a significant number of articles have been published on Faropenem.
Structure
Data?1563863711
Synonyms
ValueSource
(+)-(5R,6S)-6-((1R)-1-Hydroxyethyl)-7-oxo-3-((2R)-tetrahydro-2-furyl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acidChEBI
(5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acidChEBI
FropenemChEBI
(+)-(5R,6S)-6-((1R)-1-Hydroxyethyl)-7-oxo-3-((2R)-tetrahydro-2-furyl)-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylateGenerator
(5R,6S)-6-[(1R)-1-Hydroxyethyl]-7-oxo-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateGenerator
6alpha-[(1R)-1-Hydroxyethyl]-2-[(2R)-tetrahydrofuran-2-yl]-2,3-didehydropenam-3-carboxylic acidHMDB
Faropenem sodiumHMDB
Faropenem sodium hydrateHMDB
Fropenum sodiumHMDB
(5R,6S)-6-(R)-1-Hydroxyethyl-7-oxo-3-(R)-2-tetrahydrofuryl-4-thia-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylateHMDB
6a-[(R)-1-Hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylateHMDB
6a-[(R)-1-Hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acidHMDB
6alpha-[(R)-1-Hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylateHMDB
6Α-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylateHMDB
6Α-[(R)-1-hydroxyethyl]-2-[(R)-tetrahydrofuran-2-yl]pen-2-em-3-carboxylic acidHMDB
FaropenemChEBI
Chemical FormulaC12H15NO5S
Average Molecular Weight285.316
Monoisotopic Molecular Weight285.067093285
IUPAC Name(5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-oxolan-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Traditional Namefaropenem
CAS Registry Number106560-14-9
SMILES
[H][C@]12SC([C@H]3CCCO3)=C(N1C(=O)[C@@H]2[C@@H](C)O)C(O)=O
InChI Identifier
InChI=1S/C12H15NO5S/c1-5(14)7-10(15)13-8(12(16)17)9(19-11(7)13)6-3-2-4-18-6/h5-7,11,14H,2-4H2,1H3,(H,16,17)/t5-,6-,7+,11-/m1/s1
InChI KeyHGGAKXAHAYOLDJ-FHZUQPTBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids and derivatives
Alternative Parents
Substituents
  • Alpha-amino acid or derivatives
  • Penem
  • Thiazolecarboxylic acid or derivatives
  • Vinylogous thioester
  • Beta-lactam
  • Tertiary carboxylic acid amide
  • Tetrahydrofuran
  • Thiazole
  • Meta-thiazoline
  • Thioenolether
  • Azetidine
  • Carboxamide group
  • Secondary alcohol
  • Lactam
  • Hemithioaminal
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility14.7 g/LALOGPS
logP0.24ALOGPS
logP-0.75ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)4.16ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area87.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity69.26 m³·mol⁻¹ChemAxon
Polarizability28.16 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.89631661259
DarkChem[M-H]-160.45531661259
DeepCCS[M-2H]-206.13730932474
DeepCCS[M+Na]+181.38230932474
AllCCS[M+H]+161.732859911
AllCCS[M+H-H2O]+158.432859911
AllCCS[M+NH4]+164.832859911
AllCCS[M+Na]+165.732859911
AllCCS[M-H]-164.332859911
AllCCS[M+Na-2H]-164.032859911
AllCCS[M+HCOO]-163.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Faropenem[H][C@]12SC([C@H]3CCCO3)=C(N1C(=O)[C@@H]2[C@@H](C)O)C(O)=O3938.8Standard polar33892256
Faropenem[H][C@]12SC([C@H]3CCCO3)=C(N1C(=O)[C@@H]2[C@@H](C)O)C(O)=O2264.9Standard non polar33892256
Faropenem[H][C@]12SC([C@H]3CCCO3)=C(N1C(=O)[C@@H]2[C@@H](C)O)C(O)=O2610.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Faropenem,1TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C([C@H]3CCCO3)S[C@H]122389.5Semi standard non polar33892256
Faropenem,1TMS,isomer #2C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C([C@H]3CCCO3)S[C@H]122445.0Semi standard non polar33892256
Faropenem,2TMS,isomer #1C[C@@H](O[Si](C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C)=C([C@H]3CCCO3)S[C@H]122431.0Semi standard non polar33892256
Faropenem,1TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O)=C([C@H]3CCCO3)S[C@H]122601.2Semi standard non polar33892256
Faropenem,1TBDMS,isomer #2C[C@@H](O)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C([C@H]3CCCO3)S[C@H]122639.1Semi standard non polar33892256
Faropenem,2TBDMS,isomer #1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1C(=O)N2C(C(=O)O[Si](C)(C)C(C)(C)C)=C([C@H]3CCCO3)S[C@H]122833.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Faropenem GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9030000000-71dce16fcdf8d65d622c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Faropenem GC-MS (2 TMS) - 70eV, Positivesplash10-01xx-9201200000-ecc5011f4a75acb388b32017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Faropenem GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 10V, Positive-QTOFsplash10-03di-5920000000-17683e7c4ca5e6fd78402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 20V, Positive-QTOFsplash10-0mtc-3290000000-959bda206c6461ff13ac2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 40V, Positive-QTOFsplash10-0005-9200000000-d6c3e2166d7e27814b792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 10V, Negative-QTOFsplash10-000x-0290000000-da4deb529aa98f1ce9832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 20V, Negative-QTOFsplash10-03di-4920000000-bfb6b825adc0ad7e90b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 40V, Negative-QTOFsplash10-000i-9600000000-a9ae5153126eeb43b6702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 10V, Negative-QTOFsplash10-001i-0090000000-a6e647650849a655fb682021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 20V, Negative-QTOFsplash10-001i-1490000000-5705ce2c4bd5ea2bc7d82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 40V, Negative-QTOFsplash10-0002-9760000000-fa8a57062c4b14a9f7102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 10V, Positive-QTOFsplash10-000i-0090000000-1460f441f656badf5b502021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 20V, Positive-QTOFsplash10-000i-0090000000-29dbc58786dff48484152021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Faropenem 40V, Positive-QTOFsplash10-03fr-4920000000-13719c4824cd4281f9672021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12190
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID59303
KEGG Compound IDC13310
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFaropenem
METLIN IDNot Available
PubChem Compound65894
PDB IDNot Available
ChEBI ID51257
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 ReferencesNot Available