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Showing NP-Card for N-Carbamoylsarcosine (NP0092004)

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Record Information
Version1.0
Created at2022-05-11 18:54:29 UTC
Updated at2022-05-11 18:54:29 UTC
NP-MRD IDNP0092004
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Carbamoylsarcosine
DescriptionN-Carbamoylsarcosine, also known as CMS, 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. The N-carbamoyl derivative of sarcosine. N-Carbamoylsarcosine is a very strong basic compound (based on its pKa). It was first documented in 1986 (PMID: 3745168). N-Carbamoylsarcosine exists in all living organisms, ranging from bacteria to humans (PMID: 18699781) (PMID: 11237598) (PMID: 11171040) (PMID: 12741825).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0092004 (N-Carbamoylsarcosine)


  Mrv0541 02241203542D          

  9  8  0  0  0  0            999 V2000
   10.1574   -8.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3948   -7.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2198   -7.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3949   -8.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9781   -9.6691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9824   -8.2426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6323   -8.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6323   -6.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2187   -8.9596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
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3D MOL for NP0092004 (N-Carbamoylsarcosine)

     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -1.6516    1.0532    2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2133    0.3410    1.6508 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982    0.5446    0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1215    1.7497   -0.1781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -0.5033   -0.3169 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1991   -1.5502   -0.8054 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834   -0.6207   -0.6254 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9006    0.4711   -0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1386    0.4731   -0.3062 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3741    1.5229    0.6367 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1102    2.6507    0.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9168   -1.7548    0.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6356   -2.4603   -1.0554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847   -1.1578   -1.6772 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2845   -0.7254   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4473   -1.5769   -0.1623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6088    1.5431    1.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  7  1  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  6 12  1  0
  6 13  1  0
  6 14  1  0
  7 15  1  0
  7 16  1  0
 10 17  1  0
  4 11  1  0
  2  1  1  0
M  END
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3D SDF for NP0092004 (N-Carbamoylsarcosine)


  Mrv0541 02241203542D          

  9  8  0  0  0  0            999 V2000
   10.1574   -8.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3948   -7.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2198   -7.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3949   -8.9571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9781   -9.6691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9824   -8.2426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6323   -8.2426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6323   -6.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2187   -8.9596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  6  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0092004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(CC(O)=O)C(O)=N

> <INCHI_IDENTIFIER>
InChI=1S/C4H8N2O3/c1-6(4(5)9)2-3(7)8/h2H2,1H3,(H2,5,9)(H,7,8)

> <INCHI_KEY>
SREKYKXYSQMOIB-UHFFFAOYSA-N

> <FORMULA>
C4H8N2O3

> <MOLECULAR_WEIGHT>
132.1179

> <EXACT_MASS>
132.053492132

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
11.783793945558111

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(C-hydroxycarbonimidoyl)(methyl)amino]acetic acid

> <ALOGPS_LOGP>
-1.20

> <JCHEM_LOGP>
-2.11564067670224

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.055000728018713

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.641011177271759

> <JCHEM_PKA_STRONGEST_BASIC>
9.380130747777295

> <JCHEM_POLAR_SURFACE_AREA>
84.62000000000002

> <JCHEM_REFRACTIVITY>
40.3552

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[C-hydroxycarbonimidoyl(methyl)amino]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0092004 (N-Carbamoylsarcosine)

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PDB for NP0092004 (N-Carbamoylsarcosine)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      18.960 -15.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.270 -14.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.810 -14.052   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.270 -16.720   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      20.492 -18.049   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      20.500 -15.386   0.000  0.00  0.00           N+0
HETATM    7  O   UNK     0      23.580 -15.386   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      23.580 -12.718   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      22.808 -16.725   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    6    3                                                       
CONECT    3    2    7    8                                                  
CONECT    4    6    5    9                                                  
CONECT    5    4                                                            
CONECT    6    1    2    4                                                  
CONECT    7    3                                                            
CONECT    8    3                                                            
CONECT    9    4                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END

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3D PDB for NP0092004 (N-Carbamoylsarcosine)
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SMILES for NP0092004 (N-Carbamoylsarcosine)
CN(CC(O)=O)C(O)=N
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INCHI for NP0092004 (N-Carbamoylsarcosine)
InChI=1S/C4H8N2O3/c1-6(4(5)9)2-3(7)8/h2H2,1H3,(H2,5,9)(H,7,8)
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Synonyms
ValueSource
Carbamoyl sarcosineHMDB
Carbamoyl-sarcosineHMDB
CMSHMDB
[Carbamoyl(methyl)amino]acetic acidHMDB
Chemical FormulaC4H8N2O3
Average Mass132.1179 Da
Monoisotopic Mass132.05349 Da
IUPAC Name2-[(C-hydroxycarbonimidoyl)(methyl)amino]acetic acid
Traditional Name[C-hydroxycarbonimidoyl(methyl)amino]acetic acid
CAS Registry NumberNot Available
SMILES
CN(CC(O)=O)C(O)=N
InChI Identifier
InChI=1S/C4H8N2O3/c1-6(4(5)9)2-3(7)8/h2H2,1H3,(H2,5,9)(H,7,8)
InChI KeySREKYKXYSQMOIB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012265  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB028903  
KNApSAcK IDNot Available
Chemspider ID388495  
KEGG Compound IDC01043  
BioCyc IDCARBAMOYL-SARCOSINE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439375  
PDB IDCMS  
ChEBI ID15737  
Good Scents IDNot Available
References
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. [PubMed:18699781  ] 
  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. doi: 10.1006/jmbi.2000.4380. [PubMed:11237598  ] 
  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. doi: 10.1042/0264-6021:3530453. [PubMed:11171040  ] 
  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. [PubMed:3745168  ] 
  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. doi: 10.1021/bi027385d. [PubMed:12741825  ]