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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:09 UTC
HMDB IDHMDB0014405
Secondary Accession Numbers
  • HMDB14405
Metabolite Identification
Common NameCycloserine
DescriptionCycloserine is only found in individuals that have used or taken this drug. It is an antibiotic substance produced by Streptomyces garyphalus. [PubChem]Cycloserine is an analog of the amino acid D-alanine. It interferes with an early step in bacterial cell wall synthesis in the cytoplasm by competitive inhibition of two enzymes, L-alanine racemase, which forms D-alanine from L-alanine, and D-alanylalanine synthetase, which incorporates D-alanine into the pentapeptide necessary for peptidoglycan formation and bacterial cell wall synthesis.
Structure
Data?1676999889
Synonyms
ValueSource
(+)-4-Amino-3-isoxazolidinoneChEBI
(+)-CycloserineChEBI
(R)-4-AMINO-isoxazolidin-3-oneChEBI
alpha-CycloserineChEBI
CicloserinaChEBI
Cyclo-D-serineChEBI
CycloserinumChEBI
D-(+)-CycloserineChEBI
D-4-Amino-3-isoxazolidinoneChEBI
D-4-Amino-3-isoxazolidoneChEBI
DCSChEBI
OrientomycinChEBI
PA 94ChEBI
PA-94ChEBI
Ro-1-9213ChEBI
SeromycinChEBI
D-CycloserineKegg
ABBR DCSKegg
a-CycloserineGenerator
Α-cycloserineGenerator
D-CSHMDB
D-Cycloserine synth. BP 88HMDB
D-Cycloserine, syntheticHMDB
D-OxamicinaHMDB
D-OxamycinHMDB
DL-CycloserineHMDB
L-CycloserineHMDB
R-4-Amino-3-isoxazolidinoneHMDB
Chemical FormulaC3H6N2O2
Average Molecular Weight102.0919
Monoisotopic Molecular Weight102.042927446
IUPAC Name(4R)-4-amino-1,2-oxazolidin-3-one
Traditional Namecycloserine
CAS Registry Number68-41-7
SMILES
[H][C@@]1(N)CON=C1O
InChI Identifier
InChI=1S/C3H6N2O2/c4-2-1-7-5-3(2)6/h2H,1,4H2,(H,5,6)/t2-/m1/s1
InChI KeyDYDCUQKUCUHJBH-UWTATZPHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoxazolines. Isoxazolines are compounds containing a five-member unsaturated aliphatic ring, with an oxygen atom adjacent to a nitrogen atoms, and three carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolines
Sub ClassIsoxazolines
Direct ParentIsoxazolines
Alternative Parents
Substituents
  • Isoxazoline
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point147 °CNot Available
Boiling Point189.27 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility877 g/LNot Available
LogP-0.9Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility877 g/LALOGPS
logP-1.3ALOGPS
logP-2.4ChemAxon
logS-0.15ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area64.35 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity21.85 m³·mol⁻¹ChemAxon
Polarizability8.87 ųChemAxon
Number of Rings1ChemAxon
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]+118.7331661259
DarkChem[M-H]-113.62831661259
DeepCCS[M+H]+122.19530932474
DeepCCS[M-H]-119.95530932474
DeepCCS[M-2H]-155.830932474
DeepCCS[M+Na]+130.27430932474
AllCCS[M+H]+122.332859911
AllCCS[M+H-H2O]+117.332859911
AllCCS[M+NH4]+126.932859911
AllCCS[M+Na]+128.332859911
AllCCS[M-H]-114.232859911
AllCCS[M+Na-2H]-117.332859911
AllCCS[M+HCOO]-120.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Cycloserine[H][C@@]1(N)CON=C1O2209.5Standard polar33892256
Cycloserine[H][C@@]1(N)CON=C1O1038.6Standard non polar33892256
Cycloserine[H][C@@]1(N)CON=C1O1276.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cycloserine,1TMS,isomer #1C[Si](C)(C)OC1=NOC[C@H]1N1287.6Semi standard non polar33892256
Cycloserine,1TMS,isomer #2C[Si](C)(C)N[C@@H]1CON=C1O1351.4Semi standard non polar33892256
Cycloserine,2TMS,isomer #1C[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C1434.8Semi standard non polar33892256
Cycloserine,2TMS,isomer #1C[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C1535.5Standard non polar33892256
Cycloserine,2TMS,isomer #1C[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C2443.8Standard polar33892256
Cycloserine,2TMS,isomer #2C[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C1455.5Semi standard non polar33892256
Cycloserine,2TMS,isomer #2C[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C1523.8Standard non polar33892256
Cycloserine,2TMS,isomer #2C[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C2303.8Standard polar33892256
Cycloserine,3TMS,isomer #1C[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C)[Si](C)(C)C1550.8Semi standard non polar33892256
Cycloserine,3TMS,isomer #1C[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C)[Si](C)(C)C1622.8Standard non polar33892256
Cycloserine,3TMS,isomer #1C[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C)[Si](C)(C)C2080.6Standard polar33892256
Cycloserine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NOC[C@H]1N1497.3Semi standard non polar33892256
Cycloserine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H]1CON=C1O1560.4Semi standard non polar33892256
Cycloserine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C(C)(C)C1861.8Semi standard non polar33892256
Cycloserine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C(C)(C)C1895.5Standard non polar33892256
Cycloserine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N[C@@H]1CON=C1O[Si](C)(C)C(C)(C)C2493.0Standard polar33892256
Cycloserine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C(C)(C)C1815.4Semi standard non polar33892256
Cycloserine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C(C)(C)C1986.7Standard non polar33892256
Cycloserine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N([C@@H]1CON=C1O)[Si](C)(C)C(C)(C)C2285.2Standard polar33892256
Cycloserine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2122.0Semi standard non polar33892256
Cycloserine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2185.4Standard non polar33892256
Cycloserine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=NOC[C@H]1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2215.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Cycloserine GC-MS (2 TMS)splash10-0uy0-5900000000-06bce0b228f324fe49b42014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Cycloserine GC-MS (Non-derivatized)splash10-0uy0-5900000000-06bce0b228f324fe49b42017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloserine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-0e7a5a8b0f7ce48e45092017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cycloserine 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 - Cycloserine 10V, Positive-QTOFsplash10-0udi-4900000000-f1c1692f9e6318f523772016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 20V, Positive-QTOFsplash10-0f79-9300000000-45585d9e68724372ca942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 40V, Positive-QTOFsplash10-059f-9000000000-bac95a810bc34e20e6902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 10V, Negative-QTOFsplash10-0udi-5900000000-5babaf58090cc358ab6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 20V, Negative-QTOFsplash10-0f6x-9300000000-0ff851b2ef4ce71985ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 40V, Negative-QTOFsplash10-0596-9000000000-8a39f19e4a34080991d12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 10V, Negative-QTOFsplash10-0udl-9800000000-28ac2fbbebd31cc6100b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 20V, Negative-QTOFsplash10-0006-9200000000-739f88bc4c62ad6e99a62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 40V, Negative-QTOFsplash10-0006-9000000000-90726b17dc36e29c52992021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 10V, Positive-QTOFsplash10-0udi-0900000000-940c87bcfe09a2af1fc92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 20V, Positive-QTOFsplash10-0w2c-9400000000-13b86532b272b0b5785d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cycloserine 40V, Positive-QTOFsplash10-0006-9000000000-a3d694a542f40615fe9e2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00260 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00260 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00260
Phenol Explorer Compound IDNot Available
FooDB IDFDB098104
KNApSAcK IDNot Available
Chemspider ID5998
KEGG Compound IDC08057
BioCyc IDCPD-2482
BiGG IDNot Available
Wikipedia LinkCycloserine
METLIN IDNot Available
PubChem Compound6234
PDB ID4AX
ChEBI ID40009
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1125331
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in carboxy-lyase activity
Specific function:
Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:
DDC
Uniprot ID:
P20711
Molecular weight:
53893.755
References
  1. DENGLER HJ, RAUCHS E, RUMMEL W: [On the inhibition of L-glutamic acid and L-DOPA decarboxylase by D-cycloserine and other isoxazolidones]. Naunyn Schmiedebergs Arch Exp Pathol Pharmakol. 1962;243:366-81. [PubMed:13885421 ]