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Showing NP-Card for Formiminoglutamic acid (NP0086659)

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Record Information
Version2.0
Created at2022-05-11 16:27:23 UTC
Updated at2022-05-11 16:27:23 UTC
NP-MRD IDNP0086659
Secondary Accession NumbersNone
Natural Product Identification
Common NameFormiminoglutamic acid
DescriptionFormiminoglutamic acid, also known as N-formimino-L-glutamate or formimino-glu, 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. Formiminoglutamic acid is a very strong basic compound (based on its pKa). Formiminoglutamic acid exists in all living organisms, ranging from bacteria to humans. Within humans, formiminoglutamic acid participates in a number of enzymatic reactions. In particular, formiminoglutamic acid can be biosynthesized from 4-imidazolone-5-propionic acid through its interaction with the enzyme probable imidazolonepropionase. In addition, tetrahydrofolic acid and formiminoglutamic acid can be converted into 5-formiminotetrahydrofolic acid and L-glutamic acid through the action of the enzyme formimidoyltransferase-cyclodeaminase. Formiminoglutamic acid (FIGLU) is an intermediate in the catabolism of L-histidine to L-glutamic acid and marker for intracellular levels of folate. In humans, formiminoglutamic acid is involved in histidine metabolism. It is elevated with folate trapping, where it is accompanied by decreased methylmalonic acid, increased folate and a decrease in homocysteine. Formiminoglutamic acid is found in Daphnia pulex. Formiminoglutamic acid was first documented in 1975 (PMID: 235753). The FIGLU test is used to identify deficiencies of vitamin B12 or folate and is also found in liver disease (PMID: 500809) (PMID: 12815595).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0086659 (Formiminoglutamic acid)


  Mrv0541 02231218472D          

 12 11  0  0  1  0            999 V2000
   10.2409   -6.0818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0671   -6.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8885   -6.9686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5551   -5.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4764   -5.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4002   -7.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5475   -4.7175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8161   -5.9871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2986   -5.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0931   -8.3821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7539   -6.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7080   -4.6418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  6  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
M  END
Download

3D MOL for NP0086659 (Formiminoglutamic acid)

     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
   -2.5525   -0.7765   -2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6403   -1.2727   -2.3334 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9130   -1.4554   -1.2925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3150   -1.0027   -0.0126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4347   -0.3529    0.9376 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1444    0.9250    0.4154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9636    0.8173   -0.8180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1567   -0.0525   -0.6934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4134   -0.6060    0.3824 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0210   -0.2812   -1.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2925    0.0524    2.1144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5227   -0.1810    2.1516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6198    0.6978    3.1432 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0239   -1.9671   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3424   -1.1809    0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3465   -1.0473    1.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7919    1.4117    1.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    1.6537    0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3899    1.8523   -0.9993 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3776    0.5758   -1.7425 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4715    0.5097   -2.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7769    1.6804    3.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  5 11  1  0
 11 13  1  0
 11 12  2  0
 10 21  1  0
  7 19  1  0
  7 20  1  0
  6 17  1  0
  6 18  1  0
  5 16  1  1
  4 15  1  0
  3 14  1  0
  2  1  1  0
 13 22  1  0
M  END
Download

3D SDF for NP0086659 (Formiminoglutamic acid)


  Mrv0541 02231218472D          

 12 11  0  0  1  0            999 V2000
   10.2409   -6.0818    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0671   -6.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8885   -6.9686    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5551   -5.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4764   -5.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4002   -7.6165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5475   -4.7175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8161   -5.9871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2986   -5.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0931   -8.3821    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.7539   -6.1164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7080   -4.6418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  6  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC[C@H](NC=N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1

> <INCHI_KEY>
NRXIKWMTVXPVEF-BYPYZUCNSA-N

> <FORMULA>
C6H10N2O4

> <MOLECULAR_WEIGHT>
174.1546

> <EXACT_MASS>
174.064056818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
15.606845304849282

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-methanimidamidopentanedioic acid

> <ALOGPS_LOGP>
-1.33

> <JCHEM_LOGP>
-2.798527987203597

> <ALOGPS_LOGS>
-1.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.2072610324205115

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.4944436183792384

> <JCHEM_PKA_STRONGEST_BASIC>
10.878089693775339

> <JCHEM_POLAR_SURFACE_AREA>
110.48000000000002

> <JCHEM_REFRACTIVITY>
48.713

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-formimino-L-glutamate

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0086659 (Formiminoglutamic acid)

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PDB for NP0086659 (Formiminoglutamic acid)
HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      19.116 -11.353   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.659 -11.346   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      18.459 -13.008   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      17.836 -10.497   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.423 -10.009   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.414 -14.217   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      17.822  -8.806   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      16.457 -11.176   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      22.957 -10.009   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      18.840 -15.647   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      23.807 -11.417   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      23.722  -8.665   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1    7    8                                                  
CONECT    5    2    9                                                       
CONECT    6    3   10                                                       
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9    5   11   12                                                  
CONECT   10    6                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

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3D PDB for NP0086659 (Formiminoglutamic acid)
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SMILES for NP0086659 (Formiminoglutamic acid)
OC(=O)CC[C@H](NC=N)C(O)=O
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INCHI for NP0086659 (Formiminoglutamic acid)
InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1
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View in JSmol
Synonyms
ValueSource
N-Formimidoyl-L-glutamateChEBI
N-Formimino-L-glutamateChEBI
N-Formimidoyl-L-glutamic acidGenerator
N-Formimino-L-glutamic acidGenerator
FormiminoglutamateGenerator
Formimino-gluHMDB
Formimino-L-glutamateHMDB
Formimino-L-glutamic acidHMDB
N-(Iminomethyl)-L-glutamic acidHMDB
N-Formimidoyl-glutamic acidHMDB
N-Formimino-glutamateHMDB
Acid, formiminoglutamicHMDB
FIGLUHMDB
Chemical FormulaC6H10N2O4
Average Mass174.1546 Da
Monoisotopic Mass174.06406 Da
IUPAC Name(2S)-2-methanimidamidopentanedioic acid
Traditional NameN-formimino-L-glutamate
CAS Registry NumberNot Available
SMILES
OC(=O)CC[C@H](NC=N)C(O)=O
InChI Identifier
InChI=1S/C6H10N2O4/c7-3-8-4(6(11)12)1-2-5(9)10/h3-4H,1-2H2,(H2,7,8)(H,9,10)(H,11,12)/t4-/m0/s1
InChI KeyNRXIKWMTVXPVEF-BYPYZUCNSA-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
Daphnia pulexLOTUS Database
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 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
    • 

  • Amidine
    • 

  • Carboxylic acid amidine
    • 

  • Carboxylic acid
    • 

  • Carboximidamide
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic 1,3-dipolar compound
    • 

  • Formamidine
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • 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-1.3ALOGPS
logP-2.8ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)10.88ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area110.48 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity48.71 m³·mol⁻¹ChemAxon
Polarizability15.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000854  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022280  
KNApSAcK IDNot Available
Chemspider ID388370  
KEGG Compound IDC00439  
BioCyc IDN-FORMIMINO-L-GLUTAMATE  
BiGG ID34986  
Wikipedia LinkFormiminoglutamic acid  
METLIN ID5817  
PubChem Compound439233  
PDB IDNot Available
ChEBI ID7274  
Good Scents IDNot Available
References
General References
  1. Haurani FI, Hall CA, Rubin R: Megaloblastic anemia as a result of an abnormal transcobalamin II (Cardeza). J Clin Invest. 1979 Nov;64(5):1253-9. [PubMed:500809  ] 
  2. Perry TL, Applegarth DA, Evans ME, Hansen S, Jellum E: Metabolic studies of a family with massive formiminoglutamic aciduria. Pediatr Res. 1975 Mar;9(3):117-22. doi: 10.1203/00006450-197503000-00001. [PubMed:235753  ] 
  3. Hilton JF, Christensen KE, Watkins D, Raby BA, Renaud Y, de la Luna S, Estivill X, MacKenzie RE, Hudson TJ, Rosenblatt DS: The molecular basis of glutamate formiminotransferase deficiency. Hum Mutat. 2003 Jul;22(1):67-73. doi: 10.1002/humu.10236. [PubMed:12815595  ]