N-Carbamoylsarcosine (CHEM040745)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 00:30:32 UTC
Update Date2016-11-09 01:22:19 UTC
Accession NumberCHEM040745
Identification
Common NameN-Carbamoylsarcosine
ClassSmall Molecule
DescriptionThe N-carbamoyl derivative of sarcosine.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Carbamoyl sarcosineHMDB
Carbamoyl-sarcosineHMDB
CMSHMDB
[Carbamoyl(methyl)amino]acetic acidHMDB
Chemical FormulaC4H8N2O3
Average Molecular Mass132.118 g/mol
Monoisotopic Mass132.053 g/mol
CAS Registry NumberNot Available
IUPAC Name2-[(C-hydroxycarbonimidoyl)(methyl)amino]acetic acid
Traditional Name[C-hydroxycarbonimidoyl(methyl)amino]acetic acid
SMILESCN(CC(O)=O)C(O)=N
InChI IdentifierInChI=1S/C4H8N2O3/c1-6(4(5)9)2-3(7)8/h2H2,1H3,(H2,5,9)(H,7,8)
InChI KeySREKYKXYSQMOIB-UHFFFAOYSA-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
  • Urea
  • Carbonic acid derivative
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • 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 Solubility3.83 g/LALOGPS
logP-1.2ALOGPS
logP-2.1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.64ChemAxon
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area84.62 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.36 m³·mol⁻¹ChemAxon
Polarizability11.78 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-059l-9420000000-26d7547dadb70ab4fc08Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9100000000-f7eef7f30a71b2437a21Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-4900000000-828e01495f55c3ba6112Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-006x-9100000000-d5aaf1e2016e0db5e1efSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9000000000-7b8ae0e68a69def64830Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001c-9300000000-64fe3175ab61247e7c9cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-9100000000-3ef98ae24f347887d27aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-116ba20e6e0fcf01e7dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-df2ca252dc264c27f09eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9000000000-87f7d4792f3b20ebdd54Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9000000000-1e503e67b415a9fae1b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-9100000000-20d310b987c7d3c62e72Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0076-9000000000-7debac7e5b881e478eccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a06e49ac0ea6780c12d1Spectrum
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
1D NMR13C 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 IDNot Available
HMDB IDHMDB0012265
FooDB IDFDB028903
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCARBAMOYL-SARCOSINE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID388495
ChEBI ID15737
PubChem Compound ID439375
Kegg Compound IDC01043
YMDB IDNot Available
ECMDB IDECMDB23800
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Jiang S, Sun X, Zhang S: The ycaC-related protein from the amphioxus Branchiostoma belcheri (BbycaCR) interacts with creatine kinase. FEBS J. 2008 Sep;275(18):4597-605. doi: 10.1111/j.1742-4658.2008.06602.x. Epub 2008 Aug 11.
2. Wang WC, Hsu WH, Chien FT, Chen CY: Crystal structure and site-directed mutagenesis studies of N-carbamoyl-D-amino-acid amidohydrolase from Agrobacterium radiobacter reveals a homotetramer and insight into a catalytic cleft. J Mol Biol. 2001 Feb 16;306(2):251-61.
3. Lemaitre N, Callebaut I, Frenois F, Jarlier V, Sougakoff W: Study of the structure-activity relationships for the pyrazinamidase (PncA) from Mycobacterium tuberculosis. Biochem J. 2001 Feb 1;353(Pt 3):453-8.
4. Kim JM, Shimizu S, Yamada H: Purification and characterization of a novel enzyme, N-carbamoylsarcosine amidohydrolase, from Pseudomonas putida 77. J Biol Chem. 1986 Sep 5;261(25):11832-9.
5. Parsons JF, Calabrese K, Eisenstein E, Ladner JE: Structure and mechanism of Pseudomonas aeruginosa PhzD, an isochorismatase from the phenazine biosynthetic pathway. Biochemistry. 2003 May 20;42(19):5684-93.
6. Zajc A, Romao MJ, Turk B, Huber R: Crystallographic and fluorescence studies of ligand binding to N-carbamoylsarcosine amidohydrolase from Arthrobacter sp. J Mol Biol. 1996 Oct 25;263(2):269-83.
7. Kim JM, Shimizu S, Yamada H: Amidohydrolysis of N-methylhydantoin coupled with ATP hydrolysis. Biochem Biophys Res Commun. 1987 Feb 13;142(3):1006-12.
8. Romao MJ, Turk D, Gomis-Ruth FX, Huber R, Schumacher G, Mollering H, Russmann L: Crystal structure analysis, refinement and enzymatic reaction mechanism of N-carbamoylsarcosine amidohydrolase from Arthrobacter sp. at 2.0 A resolution. J Mol Biol. 1992 Aug 20;226(4):1111-30.
9. Ogawa J, Nirdnoy W, Tabata M, Yamada H, Shimizu S: A new enzymatic method for the measurement of creatinine involving a novel ATP-dependent enzyme, N-methylhydantoin amidohydrolase. Biosci Biotechnol Biochem. 1995 Dec;59(12):2292-4.
10. Hermann M, Knerr HJ, Mai N, Gross A, Kaltwasser H: Creatinine and N-methylhydantoin degradation in two newly isolated Clostridium species. Arch Microbiol. 1992;157(5):395-401.
11. Luo HB, Zheng H, Zimmerman MD, Chruszcz M, Skarina T, Egorova O, Savchenko A, Edwards AM, Minor W: Crystal structure and molecular modeling study of N-carbamoylsarcosine amidase Ta0454 from Thermoplasma acidophilum. J Struct Biol. 2010 Mar;169(3):304-11. doi: 10.1016/j.jsb.2009.11.008. Epub 2009 Nov 20.
12. Ogawa J, Shimizu S, Yamada H: N-carbamoyl-D-amino acid amidohydrolase from Comamonas sp. E222c purification and characterization. Eur J Biochem. 1993 Mar 15;212(3):685-91.
13. Caruthers J, Zucker F, Worthey E, Myler PJ, Buckner F, Van Voorhuis W, Mehlin C, Boni E, Feist T, Luft J, Gulde S, Lauricella A, Kaluzhniy O, Anderson L, Le Trong I, Holmes MA, Earnest T, Soltis M, Hodgson KO, Hol WG, Merritt EA: Crystal structures and proposed structural/functional classification of three protozoan proteins from the isochorismatase superfamily. Protein Sci. 2005 Nov;14(11):2887-94. Epub 2005 Sep 30.
14. Shimizu S, Kim JM, Yamada H: Microbial enzymes for creatinine assay: a review. Clin Chim Acta. 1989 Dec 15;185(3):241-52.