N-Carbamyl-L-glutamic acid (CHEM019192)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:53:56 UTC
Update Date2016-11-09 01:15:56 UTC
Accession NumberCHEM019192
Identification
Common NameN-Carbamyl-L-glutamic acid
ClassSmall Molecule
DescriptionA urea that is the N-carbamoyl derivative of L-glutamic acid. An orphan drug used to treat a deficiency in the enzyme N-acetylglutamate synthase, which leads to acute hyperammonaemia.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(2S)-2-(Carbamoylamino)pentanedioic acidChEBI
Acide carglumiqueChEBI
Acido carglumicoChEBI
Acidum carglumicumChEBI
CarbagluChEBI
Carbamino-L-glutamic acidChEBI
Carbamylglutamic acidChEBI
L-N-Carbamoylglutamic acidChEBI
Ureidoglutaric acidChEBI
(2S)-2-(Carbamoylamino)pentanedioateGenerator
Carbamino-L-glutamateGenerator
CarbamylglutamateGenerator
L-N-CarbamoylglutamateGenerator
UreidoglutarateGenerator
CarglumateGenerator
(S)-2-Ureidopentanedioic acidHMDB
N-Carbamoyl-L-glutamic acidHMDB
N-Carbamyl-L-glutamateHMDB
N-CarbamylglutamateHMDB
N-Carbamoyl-L-glutamateHMDB
N-CarbamoylglutamateHMDB
Chemical FormulaC6H10N2O5
Average Molecular Mass190.154 g/mol
Monoisotopic Mass190.059 g/mol
CAS Registry Number1188-38-1
IUPAC Name(2S)-2-(carbamoylamino)pentanedioic acid
Traditional Namecarglumic acid
SMILESNC(=O)N[C@@H](CCC(O)=O)C(O)=O
InChI IdentifierInChI=1S/C6H10N2O5/c7-6(13)8-3(5(11)12)1-2-4(9)10/h3H,1-2H2,(H,9,10)(H,11,12)(H3,7,8,13)/t3-/m0/s1
InChI KeyLCQLHJZYVOQKHU-VKHMYHEASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamic acid and derivatives. Glutamic acid and derivatives are compounds containing glutamic acid or a derivative thereof resulting from reaction of glutamic acid at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamic acid and derivatives
Alternative Parents
Substituents
  • Glutamic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Fatty acid
  • Isourea
  • Carboximidamide
  • Carboxylic acid
  • Carboximidic acid derivative
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility19.1 g/LALOGPS
logP-1.1ALOGPS
logP-1.4ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)3.36ChemAxon
pKa (Strongest Basic)-2.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area129.72 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39.41 m³·mol⁻¹ChemAxon
Polarizability16.79 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-1941000000-35634903a91e28863b1fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0910000000-e949449c58d3f3cc2c15Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9711000000-60f15bbb265b788ea08aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-0900000000-5d552fa6b00d42d5e114Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4j-1941000000-35634903a91e28863b1fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0udi-0910000000-e949449c58d3f3cc2c15Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9711000000-60f15bbb265b788ea08aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fk9-0900000000-5d552fa6b00d42d5e114Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-5088c507aa70534ff771Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xr-7491000000-9ae118d744c8a4c43184Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000j-0900000000-b40c000081e1b7470cc1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-0900000000-eb1fe6fcbdc6f376370eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-245f4056f629592bd99fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-4900000000-3a5f21eb40fd1821e24fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0pb9-9500000000-67aafe80496b10392ef0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006y-0900000000-764361bc412b5f0ce931Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6t-3900000000-c2540fd23864f2071f9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0w2m-9300000000-11ad8cdea4f07b49e70aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0005-3900000000-1b6012a21fc5e4f08ab1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6w-6900000000-2f0bc6673aa76c508051Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-ad1bb50857e6e68f1810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-d6bc8a160d559706e590Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f89-2900000000-e78d6309a9f45260eafbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-9000000000-d0b7e0dec04859c09147Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-d986898d35880221c670Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ufr-0900000000-0e99b13b20a88bbcd9ecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-4900000000-a30b3ee9c9bc68a482d0Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB06775
HMDB IDHMDB0015673
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDN-CARBAMYL-L-GLUTAMATE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCarglumic_acid
Chemspider ID108351
ChEBI ID71028
PubChem Compound ID121396
Kegg Compound IDC05829
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15055204
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17421020
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18234091
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=18516804
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=18604903
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=20410539
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=21207059
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=21225012
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=21403788
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21941437
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=22858088
12. Elpeleg O, Shaag A, Ben-Shalom E, Schmid T, Bachmann C: N-acetylglutamate synthase deficiency and the treatment of hyperammonemic encephalopathy. Ann Neurol. 2002 Dec;52(6):845-9.
13. Caldovic L, Morizono H, Daikhin Y, Nissim I, McCarter RJ, Yudkoff M, Tuchman M: Restoration of ureagenesis in N-acetylglutamate synthase deficiency by N-carbamylglutamate. J Pediatr. 2004 Oct;145(4):552-4.
14. Thompson CA: Carglumic acid approved to treat genetic hyperammonemia. Am J Health Syst Pharm. 2010 May 1;67(9):690. doi: 10.2146/news100031.
15. Haberle J: Role of carglumic acid in the treatment of acute hyperammonemia due to N-acetylglutamate synthase deficiency. Ther Clin Risk Manag. 2011;7:327-32. doi: 10.2147/TCRM.S12703. Epub 2011 Aug 2.
16. European Medicines Agency: http://www.ema.europa.eu/ema/index.jsp?curl=pages/medicines/human/medicines/000461/human_med_000685.jsp&murl=menus/medicines/medicines.jsp&mid=WC0b01ac058001d124&jsenabled=true